Aglaia andamanica
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Leaves |
Limonoid 24-epi-mellanodiol, the tirucallane aglaidiol and the two cyclopenta tetra hydrobenzo pyran derivatives pyramidaglan A and B |
Puripattanavong et al., 2000Puripattanavong, J., Weber, S., Brecht, V., Frahm, A.W., 2000. Phytochemical Investigation of Aglaia andamanica. Planta Med. 66, 740–745.
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Aglaia argentea
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Leaves |
Cycloartanes, argenteanones C-E and genteanols B-E |
Mohammad et al., 1997Mohammad, K., Martin, M.T., Leroy, E., Sevenet, T., Awang, K., Pais, M., 1997. Argenteanone C-E and argenteanols B-E, cytotoxic cycloartane from Aglaia argentea. J. Nat. Prod. 60, 81–85
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Cycloartanes: argenteanones A and B, and argenteanol |
Omobuwajo et al., 1996Omobuwajo, O.R., Martin, M.T., Perroma, G., Sevenet, T., Awang, K., Pais, M., 1996. Cytotoxic cycloartanes from Aglaia argentea. Phytochemistry 41, 1325–1328.
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Bark |
3,4-Seco apo tirucallanes, argentinic acids A-I |
Mohamad et al., 1999aMohamad, K., Sevenet, T., Dumontet, V., Pais, M., Tri, M.V., Hadi, H., Awang, K., Martin,M., 1999a. Dammarane triterpenes and pregnane steroids from Aglaia lawii and A. tomentosa. Phytochemistry 51, 1031–1037.
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Seeds |
Apotirucallane triterpenes-gentinones A-D and gentinin |
Omobuwajo et al., 1996Omobuwajo, O.R., Martin, M.T., Perroma, G., Sevenet, T., Awang, K., Pais, M., 1996. Cytotoxic cycloartanes from Aglaia argentea. Phytochemistry 41, 1325–1328.
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Aglaia cordata
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Stem bark |
Aglacins I-K three highly methoxylated lignans |
Wang et al., 2004aWang, B.G., Ebel, R., Wang, C.Y., Edrada, R.A., Wray, V., Proksh, P., 2004a. Aglacins I-K, three highly methoxylated lignans from Aglaia cordata. J. Nat. Prod. 67, 682–684.
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Aglaia crassinervia
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Bark |
Glabretal-type triterpenoids, aglaiaglabretols A-C, nine known compounds, 3-epi-cabraleahydroxylactone, cabraleahydroxylactone, rocaglaol, 2β,3β-dihydroxy-5α-pregn-17(20)-(E)-16-one, scopoletin, mixtures of cabraleadiol, epicotillol, β-sitosterol and stigmasterol |
Su et al., 2006Su, B.N., Chai, H., Mi, Q., Riswan, S., Kardono, L.B.S., Afriastini, J.J., Santarsiero, B.D., Mesecar, A.D., Farnsworth, N.R., Cordell, G.A., Swansona, S.M., Kinghorn, A.D., 2006. Activity-guided isolation of cytotoxic constituents from the bark of Aglaia crassinervia collected in Indonesia. Bioorg. Med. Chem. 14, 960–972.
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Aglaia dasyclada
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Leaves |
Rocaglamides, glycosides and putrescine bisamides |
Chaidir et al., 2001Chaidir, H.J., Lin, W.H., Ebel, R., Edrada, R., Wray, V., Nimtz, M., Sumaryono, W.,Proksch, P., 2001. Rocaglamides, glycosides, and putrescine bisamides from Aglaia dasyclada. J. Nat. Prod. 64, 1216–1220.
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Aglaia duperreana
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Twigs and leaves |
Rocaglamide derivatives and rocaglamides |
Nugroho et al., 1997aNugroho, B.W., Edrada, R.A., Güssregen, B., Wray, V., Witte, L., Proksch, P., 1997a. Insecticidal rocaglamide derivatives from Aglaia duppereana. Phytochemistry 44, 1455–1461.
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Flowers |
Insecticidal cyclopenta tetra hydro benzofuran derivatives of rocaglamide |
Chaidir et al., 1999Chaidir, H.J., Nugroho, B.W., Bohnenstengel, F.I., Wray, V., Witte, L., Hung, P.D., Kiet,L.C., Sumaryono, W., Proksch, P., 1999. New insecticidal rocaglamide derivativesfrom flowers of Aglaia duperreana(Meliaceae). Phytochemistry 52, 837–842.
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Aglaia edulis
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Leaves |
A bisamide, aglaiduline, and sulfur-containing bisamides, aglaithioduline and aglaidithioduline |
Saifah et al., 1999Saifah, E., Suttisri, R., Shamsub, S., Pengsuparp, T., Lipipun, V., 1999. Bisamides from Aglaia edulis. Phytochemistry 52, 1085–1088.
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Bark |
Benzo[b]oxepine derivatives, edulisones A and B |
Kim et al., 2005Kim, S., Su, B.N., Leonardus, S.R., Kardono, B.S., Afriastini, J.J., Gallucci, J.C., Chai, H.Y., Farnsworth, N.R., Cordell, G.A., Swanson, S.M., Kinghorn, A.D., 2005. Edulisones Aand B, two epimeric benzo[β]oxepine derivatives from the bark of Aglaia edulis. Tetrahedron Lett. 46, 4902–9021.
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Cyclopenta[b]benzofurans, aglaroxin A 1-O-acetate and 3′-methoxyaglaroxin A 1-O-acetate, benzo[b]oxepine, 19,20-dehydroedulisone A, and cyclopenta[bc]benzopyrans, edulirin A, edulirin A 10-O-acetate, 19,20-dehydroedulirin A, isoedulirin A, and isoedulirin B, cyclopenta[b]benzofuran, aglaroxin A |
Kim et al., 2006Kim, S., Chin, Y.W., Riswan, S., Su, B.N., Kardono, L.B.S., Afriastini, J.J., Chai, H., Farnsworth, N.R., Cordell, G.A., Swanson, S.M., Kinghorn, A.D., 2006. Cytotoxic flavaglines and bisamides from Aglaia edulis. J. Nat. Prod. 69, 1769–1775.
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Roots |
Favaglines, cyclopenta[bc]benzopyrans (thapsakins) and benzo[b]oxepines (thapoxepines), together with two known cyclopenta[b]benzofurans, aglaroxin A and pannellin |
Bacher et al., 1999Bacher, M., Hofer, O., Brader, G., Vajrodaya, S., Greger, H., 1999. Thapsakins: possibleb iogenetic intermediates towards insecticidal cyclopenta[β]benzofurans from Aglaia edulis. Phytochemistry 52, 253–263.
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Aglaia elaeagnoidea
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Bark |
Lignans trans-2,3-bis(3,4,5-trimethoxybenzyl)-1,4-butanediol diacetate and 20S,24S-epoxy-25-hydroxymethyldammarane-3-one, one 1H-cyclopentatetrahydro[b]benzofuran, two dammarane triterpenoids and one limonoid |
Fuzzati et al., 1996Fuzzati, N., Dyatmiko, W., Rahman, A., Achmad, F., Hostettmann, K., 1996. Triterpenoid, lignans and a benzofuran derivative from the bark of Aglaia elaeagnoidea. Phytochemistry 42, 1395–1398.
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Aglaia elliptica
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Fruits |
Rocaglamide derivatives along with rocaglamide and didesmethylrocaglamide |
Nugroho et al., 1997bNugroho, B.W., Güssregen, B., Wray, V., Witte, L., Bringmann, G., Proksch, P., 1997b. Insecticidal rocaglamide derivatives from Aglaia elliptica and A. harmsiana. Phytochemistry 45, 1579–1585.
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Aglaia exima
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Leaves |
Cycloartane; 24(E)-cycloart-24-ene-26-ol-3-one, cycloartane-type triterpenoids 24(E)-cycloart-24-ene-26-ol-3-one, cycloart-24-ene-3β,26-diol, schizandronic acid, 24(E)-3β-hydroxycycloart-24-ene-26-al, vaticinone, one dammarane-type triterpenoids cabraleahydroxylactone, and two steroids; β-sitosterol and stigmast-5-ene-28-one |
Awang et al., 2012Awang, K., Loong, X., Leong, K.H., Supratman, U., Litaudon, M., Mukhtar, M.R., Mohamad, K., 2012. Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae). Fitoterapia 83, 1391–1395.
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Stem bark |
Stigmastane steroid, 3,4-epoxy-(22R,25)-tetrahydrofuran-stigmast-5-en, triterpenoids dammara-20,25-diene-3b,24-diol, dammara-20S, 5a,24-en,3b,20-diol and steroids stigmasterol 3-O-β-d-glucoside and stigmast-5-ene-3b,4b-diol |
Harneti et al., 2014Harneti, D., Supriadin, A., Ulfah, M., Safari, A., Supratman, U., Awang, K., Hayashi,H., 2014. Cytotoxic constituents from the bark of Aglaia eximia (Meliaceae).Phytochem. Lett. 8, 28–31.
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Aglaia foveolata
|
Leaves |
Flavagline derivatives: foveoglin A, foveoglin B, isofoveoglin, cyclofoveoglin, secofoveoglin and silvestrol, pyramidatine |
Salim et al., 2007aSalim, A.A., Chai, H.B., Rachman, I., Riswan, S., Kardono, L.B.S., Farnsworth, N.R., Carcache-Blancoa, E.J., Kinghorn, A.D., 2007a. Constituents of the leaves and stem bark of Aglaia foveolata. Tetrahedron 63, 7926–7934.
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Stem bark |
Baccharane-type triterpenoid and silvestrol,17,24-epoxy-25-hydroxy-3-oxobaccharan-21-oic acid |
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Dammarane triterpenes, foveolins A and B, together with three known, 3-epi-ocotillol, eichlerianic acid and shoreic acid |
Roux et al., 1998Roux, D., Martin, Mt., Adeline, Mt., Sevenet, T., Hadi, A.H.A., Pais, M., 1998. Foveolins A and B, dammarane triterpenes from Aglaia foveolata. Phytochemistry 49, 1745–1748.
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Aglaia gracilis
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Leaf |
Secopiriferine and secoodorine and known compounds flavonol, flavagline, odorine, piriferine, pyramidatine, norsesquiterpene, desacetylaglain A, aglaistatin, |
Grege et al., 2001Grege, H., Pache, T., Brem, B., Bacher, M., Hofer, O., 2001. Insectisidal flavagalines and other compounds from Fijian Aglaia species. Phytochemistry 57, 57–64.
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Root bark |
Marikarin and 3′-hydroxy-marikarin along with known algafoline, aglaiastatin, dehydroalgastatin, shoreic acid |
Grege et al., 2001Grege, H., Pache, T., Brem, B., Bacher, M., Hofer, O., 2001. Insectisidal flavagalines and other compounds from Fijian Aglaia species. Phytochemistry 57, 57–64.
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Aglaia grandis
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Leaves |
Pregnanes and cycloartane type triterpenoid hydroperoxides |
Inada et al., 1997Inada, A., Muryta, H., Inatomi, Y., Nakanishi, T., Darnaedi, D., 1997. Pregnanes andtriterpenoid hydroperoxides from the leaves of Aglaia grandis. Phytochemistry 45, 1225–1228.
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Putrescine bisamides grandiamides A-C and aromadendrane-type sesquiterpene 4b,10a-dihydroxyaroma- Dendrane |
Inada et al., 2000Inada, A., Shono, K., Murata, H., Inatomi, Y., Darnaedi, D., Nakanishi, T., 2000. Three putrescine bisamides from the leaves of Aglaia grandis. Phytochemistry 53, 1091–1095.
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Aglaia harmsiana
|
Leaves |
Cycloartane type triterpene-Cycloartane-3β,29-diol-24-one, (24R)-cycloartane-24,25-diol-3-one |
Inada et al., 1995Inada, A., Muryta, H., Inatomi, Y., Nakanishi, T., Darnaedi, D., 1995. Cycloartane triterpenes from the leaves of Aglaia harmsiana. J. Nat. Prod. 58, 1143–1146.
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Rocaglamide compound |
Nugroho et al., 1997bNugroho, B.W., Güssregen, B., Wray, V., Witte, L., Bringmann, G., Proksch, P., 1997b. Insecticidal rocaglamide derivatives from Aglaia elliptica and A. harmsiana. Phytochemistry 45, 1579–1585.
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Aglaia ignea
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Bark |
Dammarenolic acid |
Esimone et al., 2010Esimone, C.O., Eck, G., Nworu, C.S., Hoffmann, D., Uberla, K., Proksch, P., 2010. Dammarenolic acid, a secodammarane triterpenoid from Aglaia sp. shows potentanti-retroviral activity in vitro. Phytomedicine 17, 540–547.
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Aglaia lawii
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Leaves |
Dammaranes, aglinins A and B together with cabraleone, eichlerianic acid and shoreic acid |
Mohamad et al., 1999aMohamad, K., Sevenet, T., Dumontet, V., Pais, M., Tri, M.V., Hadi, H., Awang, K., Martin,M., 1999a. Dammarane triterpenes and pregnane steroids from Aglaia lawii and A. tomentosa. Phytochemistry 51, 1031–1037.
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Bark |
A pregnane steroid, namely (E)-aglawone 20S, 24S-epoxy-dammarane-3α,25-diol acetate |
Qiu et al., 2001Qiu, S.X., Nguyen, V.H., Le, T.X., Gu, J.Q., Lobkovsky, E., Khanh, T.C., Soejarto, D.D.,Clardy, J., Pezzuto, J.M., Dong, Y., Mai, V.T., Le, M.H., Fong, H.H., 2001. A pregnane steroid from Aglaia lawii and structure confirmation of cabraleadiol monoacetate by X-ray crystallography. Phytochemistry 56, 775–780.
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Aglaia leucophylla
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Stem bark |
(+)-ocillatone, (+)-ocotillol, (+)-cabraleone, (+)-eichlerianic acid, (+)-caryophyllene oxide, (24Z)-3,4-secotirucalla-4 (28) 7,24-triene-3,26-dioic acid and 3-monomethyl ester. |
Benosman et al., 1994Benosman, A., Richomme, P., Sevenet, T., Hadi, A.H.A., Bruneton, J., 1994. Secotirucallane triterpenes from the stem bark of Aglaia leucophylla. Phytochemistry 37,1143–1145.
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Tirucallane triterpene, (−)-leucophyllonealong with (−)-caryophyllene oxide, (−)-niloticin, (−)-bourjotinolone and (−)-piscidinol. |
Benosman et al., 1995Benosman, A., Richomme, P., Sevenet, T., Hadi, A.H.A., Bruneton, J., 1995. Tirucallane triterpenes from the stem bark of Aglaia leucophylla. Phytochemistry 40, 1485–1487.
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Aglaia loheri
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Leaves |
Spinasterol, trilinolein, phytyl fatty acid ester |
Ragasa et al., 2012Ragasa, C.Y., Torres, O.B., Bernardo, L.B., Mandia, E.H., Don, M.J., Shen, C.C., 2013. Glabretal-type triterpenoids from Dysoxylum mollissimum. Phytochem. Lett. 6, 514–518.
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Aglaia odorata
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Leaves |
Cyclopenta tetra hydro benzo furans along with desmethyl rocaglamide, methyl rocaglate, rocaglaol |
Ishibashi et al., 1993Ishibashi, F., Satasook, C., Isman, M.B., Towers, G.H.N., 1993. Indecticidal 1H-cyclopentate-trahydro[b]benzofurans from Aglaia odorata (Lour) (Meliaceae). Phytochemistry 32, 307–310.
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Odorine, odorinol and dehydrodorin |
Duh et al., 1993Duh, C.Y., Wang, S.K., Hou, R.S., Wu, Y.C., Wang, Y., Cheng, M.C., Chang, T.T., 1993.Dehydroodorin, a cytotoxic diamide from Aglaia formosana. Phytochemistry 34,857–858.
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Rocaglamide congeners, aglain derivatives, two aminopyrrolidines odorine and odorinol, three flavonoid derivatives and syringaresinol |
Nugroho et al., 1999Nugroho, B.W., Edrada, R.A., Wray, V., Witte, L., Bringmann, G., Gehling, M., Proksch, P., 1999. An insecticidal rocaglamide derivatives and related compounds from Aglaia odorata (Meliaceae). Phytochemistry 51, 367–376.
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Dolabellane diterpenoids (1R,3E,7E,10S,11S,12R)-dolabella-3,7-dien-10,18-diol, (1R,3S,7E,11S,12R)-dolabella-4(16),7-dien-3,18-diol, (1R,7E,11S,12R)-18-hydroxydolabella-4(16),7-dien-3-one, (1R,3S,4S,7E,11S,12R)-3,4epoxydolabella-7-en-18-ol, and (1R,3R,7E,11S,12R)-dolabella-4(16),7,18-trien-3-ol. |
Cai et al., 2010Cai, X.H., Wang, Y.Y., Zhao, P.J., Li, Y., Luo, X.D., 2010. Dolabellane diterpenoids from Aglaia odorata. Phytochemistry 71, 1020–1024.
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Dolabellane diterpenoids, two dammarane triterpenoids and a protostane triterpenoid |
Yodsaoue et al., 2012Yodsaoue, O., Sonprasit, J., Karalai, C., Ponglimanont, C., Tewtrakul, S., Chantrapromma, S., 2012. Diterpenoids and triterpenoids with potential anti-inflammatory activity from the leaves of Aglaia odorata. Phytochemistry 76, 83–91.
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Leaves twigs |
Coumarinolignoid, 8-(70,80,90-propanetriol-40-methoxy-30-O-phenylpropanoid)-7-hydroxy-6-methoxycoumarin. |
Zhang et al., 2012aZhang, H., Song, Z., Chen, W., Wu, X., Xu, H., 2012a. Chemical constituents from Aglaia odorata Lour. Biochem. Syst. Ecol. 41, 35–40.
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Twigs |
Insecticidal rocaglamide compounds |
Nugroho et al., 1999Nugroho, B.W., Edrada, R.A., Wray, V., Witte, L., Bringmann, G., Gehling, M., Proksch, P., 1999. An insecticidal rocaglamide derivatives and related compounds from Aglaia odorata (Meliaceae). Phytochemistry 51, 367–376.
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Norsesquiterpene 4α, 10β-dihydroxy-1βH,5αH-guai-6(7)-en-11-one and four new sesquiterpenes 1β,4α,7β-trihydroxy-14β-methyl-eudesman-11(12)-ene, 1α,6β,12-trihydroxy-1βH,5αH,11H-guai-6(7)-ene, 4α7β,11-trihydroxy-1βH,5αH-guai-10(14)-ene, and 4α,10α,11-trihydroxy-1βH,5βH-guai-7(8)-ene along with four known guaianediol, orientalol A, orientalol B and 1β,6α-dihydroxy-10β-methyl-5αH,7αH-eudesm-4-one |
Liu et al., 2014Liu, S., Liu, S.B., Zuo, W.J., Guo, Z.K., Mei, W.L., Dai, H.F., 2014. New sesquiterpenoids from Aglaia odorata var. microphyllina and their cytotoxic activity. Fitoterapia 92, 93–99.
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Dried twigs |
Dammarane triterpenes and aminopyrolidine bis-amides such as odorinol |
Janprasert et al., 1993Janprasert, J., Satasook, C., Sukumalan, P., Champagne, D.E., Isman, M.B., Wiriyachitra, P., Towers, G.H.N., 1993. Rocaglamide, a new natural insecticide from Aglaia odorata (Lour.) (Family Meliaceae). Phytochemistry 32, 67–69.
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Flower essential oil |
Cadinane derivatives murrola-4,10 (14)-dien-1β-ol accompanied by 1α-alchol, methyl jasmonate |
Weyerstahl et al., 1999Wu, H.F., Zhang, X.P., Wang, Y., Zhang, J.Y., Ma, G.X., Tian, Y., Wu, L.Z., Chen, S.H., Yang, J.S., Xu, X.D., 2013. Four new diterpenes from Aphanamixis polystachya. Fitoterapia 90, 126–131.
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Aglaia oligophylla
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Leaves |
Dipterocarpol, ocotillone, cabraleone, ocotillol, 20(S),24(S)-dihydroxydammar-25-en-3-one, 20S,25-epoxy-24R-hydroxy-3-dammaranone, 20S,25-epoxy-24R-hydroxydammarane-3a-ol, flavagaline rocaglaol, bisamides odorine and 20-epi-odorine |
Joycharat et al., 2008Joycharat, N., Greger, H., Hofer, O., Saifah, E., 2008. Flavaglines and triterpenes as chemical markers of Aglaia oligophylla. Biochem. Syst. Ecol. 36, 584–587.
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Aglaia ponapensis
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Leaves and stems |
Cyclopenta[bc]benzopyran, ponapensin, and an aglaialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone, cyclopenta[b]benzofuran(methyl rocaglate) four cyclopenta[bc]benzopyrans 4-epi-aglain A, aglain B, 10-O-acetylaglain B, and aglain C, and four pregnane steroids (E)-volkendousin, (Z)-volkendousin, 2β,3β-dihydroxy-5-pregn-17(20)-(E)-en-16-one, 20 and 2β,3β-dihydroxy-5-pregn-17(20)-(Z)-en-16-one |
Salim et al., 2007bSalim, A.A., Pawlus, A.D., Chai, H.B., Farnsworth, N.R., Kinghorn, A.D., Carcache-Blanco, E.J., 2007b. Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kBinhibitory activity from Aglaia ponapensis. Bioorg. Med. Chem. Lett. 17, 109–112.
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Aglaia rubiginosa
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Leaves |
Androstane derivatives. 17-octanor-cycloartane-ring-A-seco acid Four cyclo artane-type triterpenes and three unusual cholesterol derivatives |
Weber et al., 2000Weber, S., Puripattanavong, J., Brecht, V., Frahm, A.W., 2000. Phytochemical investigation of Aglaia rubiginosa. J. Nat. Prod. 63, 636–642.
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Twigs |
Cyclopenta{b}benzofuran, 1-O-acetyl rocaglaol |
Rivero-Cruz et al., 2004Rivero-Cruz, J.F., Chai, H.B., Kardono, L.B.S., Setyowati, F.M., Afriastini, J.J., Riswan, S., Farnsworth, N.R., Cordell, G.A., Pezzuto, J.M., Swanson, S.M., Kinghorn, A.D., 2004. Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa. J. Nat. Prod. 67, 343–347.
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Aglaia silvestris
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Leaves, twigs and roots |
Triterpenoids silvaglin A, B, methylisofoveolate B, methylfoveolate B, isosilvaglin A, B, desoxysilvaglin B, aglasilvinic acid, isoeichlerianic acid, methylfoveolate B, aglasilvinic acid, one pregnane steroid pregnacetal, two sesquiterpenes viridiflorol, α-muurolene |
Pointinger et al., 2008Pointinger, S., Promdang, S., Vajrodaya, S., Pannell, C.M., Hofer, O., Mereiter, K., Greger, H., 2008. Silvaglins and related 2,3-secodammarane derivatives – unusual types of triterpenes from Aglaia silvestris. Phytochemistry 69, 2696–2703.
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Roots |
Silvaglenamin-unusual dimeric triterpene structure with two dammarane units linked with an enaminic NH group |
Hofer et al., 2009Hofer, O., Pointinger, S., Brecker, L., Peter, K., Greger, H., 2009. Silvaglenamin – a novel dimeric triterpene alkaloid from Aglaia silvestris. Tetrahedron Lett. 50, 467–468.
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Aglaia smithii
|
Bark |
Dammarane triterpenoids, aglinone and aglinin E (20S,24S-epoxy-25-hydroxy-1-endammarene) along with three known compounds, 3-epiocotillol, aglinin A and eichlerianic acid |
Harneti et al., 2012Harneti, D., Tjokronegoro, R., Safari, A., Supratman, U., Loong, X., Mukhtar, M.R.,Mohamad, K., Awang, K., Hayashi, H., 2012. Cytotoxic triterpenoids from thebark of Aglaia smithii (Meliaceae). Phytochem. Lett. 5, 496–499.
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Aglaia spectabilis
|
Bark |
Rocaglamide derivatives |
Schneider et al., 2000Schneider, C., Bohnenstengel, F.I., Nugroho, B.W., Wray, V., Witte, L., Hung, P.D., Kiet,L.C., Proksch, P., 2000. Insecticidal rocaglamide derivatives from Aglaia spectabilis (Meliaceae). Phytochemistry 54, 731–736.
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Leaves |
Two bisamides secoisopiriferinol and secoisoodorinol |
Greger et al., 2008Greger, H., Hofer, M., Teichmann, K., Schinnerl, J., Pannell, C.M., Vajrodaya, S., Hofer, O., 2008. Amide-esters from Aglaia tenuicaulis – first representatives of a class of compounds structurally related to bisamides and flavaglines. Phytochemistry 69, 928–938.
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Aglaia tenuicaulis
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Leaves, stem and root bark |
Six amide-esters tenucaulin A, B, isotenucaulin A, aglatenin, tenaglin, caulitenin and two sulphur-containing bisamides pyrrolotenin, secopyrrolotenin |
Greger et al., 2008Greger, H., Hofer, M., Teichmann, K., Schinnerl, J., Pannell, C.M., Vajrodaya, S., Hofer, O., 2008. Amide-esters from Aglaia tenuicaulis – first representatives of a class of compounds structurally related to bisamides and flavaglines. Phytochemistry 69, 928–938.
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Aglaia testicularis
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Leaves |
Rocaglamide derivatives 1 and 2, one aglain derivative aglaxiflorin D, two cinnamic acid-derived bisamides, piriferine and odorinol and a diarylbutane lignan, secoisolariciresinol dimethyl ether |
Wang et al., 2004bWang, J.S., Zhang, Y., Wang, X.B., Wei, D.D., Luo, J., Luo, J.G., Yang, M.H., Yao, H.Q., Sun, H.B., Kong, L.Y., 2012a. A pair of tirucallane C27-triterpenoid cyclopentenoneepimers from the stem barks of Aphanamixis grandifolia. Tetrahedron Lett. 53, 1705–1709.
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Aglaia tomentosa
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Bark |
Dammaranes, aglinins C and D two pregnane steroids, aglatomins A and B and cyclopentate-trahydrobenzofuran, rocaglaol |
Mohamad et al., 1999bMohamad, K., Martin, M.A., Litaudon, M., Gaspard, C., Sevenet, T., Pais, M., 1999b. Tirucallane triterpenes from Dysoxylum macranthum. Phytochemistry 52, 1461–1468.
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Amoora rohituka
|
Bark |
Amoorinin |
Agnihotri et al., 1987Agnihotri, V.K., Srivastava, S.D., Srivastava, S.K., 1987. A new limonoid, amoorinin,from the stem bark of Amoora rohituka. Planta Med. 53, 298–299.
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|
Stem bark |
Guaiane-derived sesquiterpenoids,6β,7β-epoxyguai-4-en-3-one and 6β,7β-epoxy-4β,5-dihydroxyguaiane. |
Chowdhury et al., 2003bChowdhury, R., Hasan, C.M., Rashid, M.A., 2003b. Guaiane sesquiterpenes from Amoora rohituka. Phytochemistry 62, 1213–1216.
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|
Seeds |
7-Keto-octadec-cis-11-enoic acid |
Daulatabad and Jamkhandi, 1997Daulatabad, C.D., Jamkhandi, S.A.M., 1997. A keto fatty acid from Amoora rohituka seed oil. Phytochemistry 46, 155–156.
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Aphanamixis grandifolia
|
Leaves and twigs |
Tirucallane triterpenoids, 2α-ethoxy-2,3-secotirucalla-2,29-epoxy-7-ene-23-oxo-3-oic acid (1) and (23E)-2α-hydroxytirucalla-7,23,25-triene-3-one and a tirucallane triterpenoid 2,3-secotirucalla-2,3; 2,29-diepoxy-7-ene-3,23-dione |
Wang et al., 2012aWang, J.S., Zhang, Y., Wang, X.B., Wei, D.D., Luo, J., Luo, J.G., Yang, M.H., Yao, H.Q., Sun, H.B., Kong, L.Y., 2012a. A pair of tirucallane C27-triterpenoid cyclopentenoneepimers from the stem barks of Aphanamixis grandifolia. Tetrahedron Lett. 53, 1705–1709.
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|
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Cycloartane triterpenoids, aphagrandinoids A-C and aphagrandinoid D, and (20R)-3β-hydroxy-24,25,26,27-tetranor-5α-cycloartan-23,21-olide |
Wang et al., 2013Wang, X.Y., Tang, G.H., Yuan, C.M., Zhang, Y., Zou, T., Yu, C., Zhao, Q., Hao, X.J., He, H.P., 2013. Aphagrandinoids A-D, cycloartane triterpenoids with antibacterial activities from Aphanamixis grandifolia. Fitoterapia 85, 64–68.
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|
Leaves and stem |
Terpenoids, nemoralisins D-G, diterpenoids, nemoralisin C and nemoralisin |
Zhang et al., 2014Zhang, R., He, H.P., Di, Y.T., Li, S.L., Zuo, G.Y., Zhang, Y., Hao, X.J., 2014. Chemical constituents from Aphanamixis grandifolia. Fitoterapia 92, 100–104.
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|
Stem barks |
Tirucallane type C26 triterpenoids, 3a-hydroxyl-21a-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3a-hydroxy-21b-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21a-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21b-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, and 3-oxo-21a-ethoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone |
Zhang et al., 2010Zhang, Y., Wang, J., Wei, D., Wang, X., Luo, J., Luo, J., Kong, L., 2010. Cytotoxic tirucallane C26 triterpenoids from the stem barks of Aphanamixis grandifolia. Phytochemistry 71, 2199–2204.
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|
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Tirucallane C27-triterpenoid epimers, aphagranins A and B |
Wang et al., 2012bWang, J.S., Zhang, Y., Wang, X.B., Kong, L.Y., 2012b. Aphanalides A-H, ring Aseco limonoids from the fruits of Aphanamixis polystachya. Tetrahedron 68, 3963–3971.
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|
Stem |
2,3-Seco-tirucallane triterpenoid derivatives aphanamgrandins A-F, three 3,4-seco-29-nor-tirucallane triterpenoid derivatives aphanamgrandins G–I, one 3,4-seco-tirucallane triterpenoid aphanamgrandin J, two tirucallane triterpenoids aphanamgrandin K and (23Z)-25-hydroxy-tirucalla-7,23-diene-3-one and three known triterpenoids (23S)-21,23-epoxy-5a-cycloart-24-en-3b-ol, 3b,25-dihydroxy-tirucalla-7,23-diene, and (−)-leucophyllone. |
Zeng et al., 2012Zeng, Q., Guan, B., Qin, J.J., Wang, C.H., Cheng, X.R., Ren, J., Yan, S.K., Jin, H.Z., Zhang, W.D., 2012. 2,3-Seco- and 3,4-seco-tirucallane triterpenoid derivatives from the stems of Aphanamixis grandifolia Blume. Phytochemistry 80, 148–155.
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|
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Triterpenoid Aphanamgrandiol A |
Zeng et al., 2013Zeng, Q., Guan, B., Ren, J., Wang, C.H., Cheng, X., Qin, J.J., Yan, S.K., Jin, H.Z., Zhang, W.D., 2013. Aphanamgrandiol A, a new triterpenoid with a unique carbon skeleton from Aphanamixis grandifolia. Fitoterapia 86, 217–221.
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|
Fruits |
Limonoids aphanamolides C and D, aphanamolide A and aphapolynin A |
Zhang et al., 2013aZhang, Y., Wang, J.S., Gu, Y.C., Kong, L.Y., 2013a. Ring A rearranged limonoids from the fruits of Aphanamixis grandifoliaand their cytotoxicity evaluation. Phytochem.Lett. 6, 539–543.
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Aphanamixis polystachya
|
Stem bark |
Diterpenes possessing rare five-membered peroxide ring, aphanaperoxides E-H |
Wu et al., 2013Wu, H.F., Zhang, X.P., Wang, Y., Zhang, J.Y., Ma, G.X., Tian, Y., Wu, L.Z., Chen, S.H., Yang, J.S., Xu, X.D., 2013. Four new diterpenes from Aphanamixis polystachya. Fitoterapia 90, 126–131.
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|
Bark |
Dihydroamoorinin |
Agarwal et al., 2001Agarwal, S.K., Verma, S., Singh, S.S., Sushil, K., 2001. A new limonoid from Aphanamixis polystachya. Ind. J. Chem. 40, 536–538.
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|
Roots |
Limonoids and flavonoids Amoorinin-3-O-α-l-rhamnopyranosyl-(1 to 6)-β-d-gluco pyranoside, 8-methyl-7,2′,4′-tri-O-methyl flavonone-5-O-α-l-rhamnopyranosyl-(1 to 4)-β-d-glucopyranosyl-(1 to 6)-β-d-glucopyranoside and 8-C-methyl-5,7,3′,4′-tetrahydroxy flavone-3-O-α-l-arabino pyranoside |
Srivastava et al., 2003Srivastava, S.K., Srivastava, S.D., Srivastava, S., 2003. New biologically activelimonoids and flavonoids from Aphanamixis polystachya. Ind. J. Chem. 42, 3155–3158.
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|
Fruits |
Ring A-seco limonoids, aphanalides A-H |
Wang et al., 2012cWang, X.Y., Tang, G.H., Yuan, C.M., Zhang, Y., Hou, L., Zhao, Q., Hao, X.J., He, H.P., 2012c. Two new tirucallane triterpenoids from Aphanamixis grandifolia. Nat. Prod. Bioprospect. 2, 222–226.
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Highly oxidized A,B-seco limonoids, aphapolynins A and B |
Zhang et al., 2011Zhang, Y., Wang, J.S., Wang, X.B., Wei, D.D., Luo, J.G., Luo, J., Yang, M.H., Kong, L.Y.,2011. Aphapolynins A and B, two new limonoids from the fruits of Aphanamixis polystachya. Tetrahedron Lett. 52, 2590–2593.
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|
Seed |
Limonoids rohituka-12, rohituka-13 and rohituka-14 and kihadalactone A and known compounds polystachin, rohituka-7 and rohituka-9. |
Mulholland and Naidoo, 1999Mulholland, D.A., Naidoo, N., 1999. Limonoids from Aphanamixis polystacha. Phytochemistry 51, 927–930.
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Astrotrichilia asterotricha
|
Bark |
Astrotrichilin |
Mulholland et al., 1996Mulholland, D.A., Nair, J.J., Taylor, D.A.H., 1996. Astrotrichilin, alimonoid from Astrotrichilia asterotricha. Phytochemistry 42, 1239–1241.
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Astrotrichilia voamatata
|
Stem bark |
Voamatins A and B |
Mulholland et al., 1999aMulholland, D.A., Schwikkard, S.L., Randrianarivelojosia, M., 1999a. Limonoids from Astrotrichilia voamatata. Phytochemistry 52, 705–707.
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|
Stem bark |
Voamatins C and D |
Mulholland et al., 2000aMulholland, D.A., Randrianarivelojosia, M., Lavaud, C., Nuzillard, J.M., Schwikkar, S.L., 2000a. Limonoid derivatives from Astrotrichilia voamatata. Phytochemistry 53, 115–118.
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Azadirachta indica
|
Leaves |
Nimbolide, 28-deoxonimbolide |
Kigodi et al., 1989Kigodi, P.G.K., Blaskó, G., Thebtaranonth, Y., Pezzuto, J.M., Cordell, G.A., 1989. A new limonoid from Azdirachtaindica. Spectroscopic and biological investigation of nimbolide and 28-deoxynimbolide. J. Nat. Prod. 52, 1246–1251.
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|
|
Nimbinene and 6-deacetyl nimbinene, nimbadiol, hyperoside, quercetin, rutin, meldenindiol, 4α,6α-dihydroxy-A-homoazadirone |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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|
Tetracyclic triterpenoids zafaral 24,25,26,27-tetranorapotirucalla-(apoeupha)-6α-acetoxy-1,14-dien-3,16-dione-21-al(1) and meliacinanhydride 24,25,26,27-tetranorapotirucalla-(apoeupha)-6α-hydroxy, 11α-methoxy-7α,12α diacetoxy,1,14,20(22)-trien-3-one (2) |
Siddiqui et al., 2004Siddiqui, B.S., Afshan, F., Gulzar, T., Hanif, M., 2004. Tetracyclic triterpenoids from the leaves of Azadirachta indica. Phytochemistry 65, 2363–2367.
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Teetranortriterpenoids 24,25,26,27 tetranorapotirucalla-(apoeupha)-6α-O-methyl, 7α-S enecioy (7-deacetyl)-1α,12α,21,23-tetrahydroxy-21,23-epoxy-2,14,20 (22)-trien-1,16-dione (1) |
Siddiqui et al., 2003Siddiqui, B.S., Afshan, F., Gulzar, T., Sultana, R., Naqvi, S.N.H., Tariq, R.M., 2003. Tetracyclic triterpenoids from the leaves of Azadirachta indica and their insecticidal activities. Chem. Pharm. Bull. 51, 415–417.
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Triterpenoids 22,23-dihydronimocinol and des furano-6-α-hydroxyazadiradione |
Siddiqui et al., 2002Siddiqui, B.S., Afsjam, F., Naqvi, S.N.H., Tariq, R.M., 2002. Two new triterpenoids from Azadirachta indica and their insecticidal activity. J. Nat. Prod. 65, 1216–1218.
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|
Seeds |
1α-Methoxy-1,2-dihydroepoxyazadiradione, 1β,2β,14β,15β-diepoxyazadiradione, 7-acetylneotrichilenone, three C-7 benzoates of tetranortriterpenoids (I, II, III), nimbin and β-sitosterol, nimbinene and 6-deacetyl nimbinene, nimbandiol |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.. |
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|
Tetranortriterpenoids 1α,2α-epoxy-17β-hydroxyazadiradione,1α,2α-epoxynimolicinol, 7-deacetyl nimolicinol |
Hallur et al., 2002Hallur, G., Sivaramakrishnan, A., Bhat, S.V., 2002. Three new tetranortriterpenoids from neem seed oil. J. Nat. Prod. 65, 1177–1179.
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|
|
Margocin, margocinin and margocilin |
Ara et al., 1990Ara, I., Faizi, S., Siddiqui, S., 1990. Tricyclic diterpenoids from root bark of Azadirachta indica. Phytochemistry 29, 911–914.
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|
|
Limocinol, limonone, limocin A and B, limocinin. |
Siddiqui et al., 1991Siddiqui, S., Siddiqui, B., Ghiasuddin, S., Faizi, S., Siddiqui, S., Faizi, S., 1991. Terpenoids from the fruit coatings of Azadirachta indica. Phytochemistry 30, 1615–1619.
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|
Root bark |
7α-acetoxy-4,4,8-trimethyl-5α-(13α Me)-androsta-1,14-dien-3,16-dione,7α-acetoxy-4,4,8-trimethyl-5α-(13α Me)-17-oxa-androsta-1,14-dien-3,16-dione and 7α-acetoxy-4,4,8-trimethyl-5α-17-oxa-androsta-1,14-dien-3,16-dione |
Siddiqui et al., 1992Siddiqui, B., Ghiasuddin, S., Faizi, S., Siddiqui, S., 1992. Triterpenoids from the fresh fruit coats of Azadirachta indica. Phytochemistry 31, 4275–4278.
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|
Fruits |
Nimolicinol |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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|
Nodal callus |
Azadirachtin |
Babu and Nair, 2004Babu, V.S., Nair, G.M., 2004. Bioproduction of azadirachtin from callus cultures of neem (Azadirachta indica A. Juss.). In: IUPAC: International Conference on Biodiversity and Natural Products Chemistry and Medical Applications, New Delhi ,p. 52.
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Azadirachta indica
|
Seed kernels |
Azadirachtin derivatives, 29-oxymethylene azadirachtin analogue,29-oxymethylene-11-demethoxy-carbonyl-11-α-hydroxy azadirachtin (azadirachtin M), 22,23-dihydro-23α hydroxy-3-tigloyl-11-deoxyazadirachtin (azadirachtin N) |
Luo et al., 1999Luo, X.D., Ma, Y.B., Wu, S.H., Wu, D.G., 1999. Two novel azadirachtin derivatives from Azadirachta indica. J. Nat. Prod. 62, 1022–1024.
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|
|
Apo-tirucallols, 1a,7a-diacetoxyl-17a-20S-21,24-epoxy-apotirucall-14-ene-3a,23R,24S,25-tetraol |
Luo et al., 2002Luo, X.D., Wu, S.H., Wu, D.G., Ma, Y.B., Qi, S.H., 2002. Three new apotirucallols with six-membered hemiacetal from Meliaceae. Tetrahedron 58, 6691–6695.
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|
Seeds |
11-Hydroxyazadirachtin-B, 1-tigloyl-3-acetylazadirachtinin, 1,2-diacetyl-7-tigloyl-12-hydroxy vilasinin and 23-desmethyl limocin-B |
Kumar et al., 1996Kumar, C.S .S.R., Srinivas, M., Yakkundi, R., 1996. Limonoids from the seeds of Azadirachta indica. Phytochemistry 43, 451–455.
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|
Fruit coats |
Azadironolide, iso azadironolide, azadiradionolide |
Siddiqui et al., 1999Siddiqui, B.S., Ghiasuddin, F.S., Rasheed, M., 1999. Triterpenoids of the fruit coats of Azadirachta indica. J. Nat. Prod. 62, 1006–1009.
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|
|
Tetracyclic triterpenoids, salimuzzalin, azadirolic acid, azadiradionol, azadironol |
Siddiqui et al., 1998Siddiqui, B.S., Ghiasuddin, S., Faizi, S., 1998. Tetracyclic triterpenoids of the fruit coats of Azadirachta indica. Phytochemistry 47, 1631–1636.
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|
|
Tetranortriterpenoid, 11-epi-azadirachtin H |
Ramji et al., 1996Ramji, N., Venkatakrishnan, K., Madyastha, K.M., 1996. 11-Epiazadirachtin H from Azadirachta indica. Phytochemistry 42, 561–562.
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|
Dried cells and seed kernel |
Azadirachtin |
Jarvis et al., 1997Jarvis, A.P., Morgan, E.D., van der Esch, S.A., Vitali, F., Ley, S.V., Pape, A., 1997. Identification of azadirachtin in tissue-cultured cells of neem (Azadirachta indica). Nat. Prod. Lett. 10, 95–98.
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|
|
Triterpenoid, 1α,7α-diacetoxy apo tirucall-14-ene-3α,21,22,24,25-pentaol. |
Luo et al., 2000eLuo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G., 2000e. A new triterpenoid from Azadirachta indica A. Juss. Fitoterapia 71, 668–672.
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|
Flowers |
Neeflone, a new tetranortriterpenoid-15-acetoxy-7-deacetoxydihydro azadione |
Nanduri and Banstola, 1995Nanduri, S., Banstola, P., 1995. Neeflone, a new tetranortriterpenoid from the flowers of Azadirachta indica A. Juss (Meliaceae). Ind. J. Chem. 34, 1019–1021.
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|
Essential oil of flowers |
Sesquiterpenes α-cubebene, copaene, humulene, Δ-cadinene, 3,4-dimethylthiophene, dipropyl disulphide, nonanal, propyl propenyl disulphide, Δ-elemene, α-gurjunene, linalool, caryophyllene, aromadendrene, allo-aromadendrene, viridiflorene, α-muurolene, Δ-cadinene, bicyclogermacrene, cis-3,5-diethyl-1,2-4-trithiolane, cadina-1,4-diene, trans-3,5-diethyl-1,2,4-trithiolane, 2-tridecanone, calamene, α-calacorene, palustrol, ledol, nerolidol, ethyl laurate, cubenol, epicubenol, globulol, viridiflorol, τ-cadinol, τ-muurolol, phytol |
Aromdee and Sriubolmas, 2006Aromdee, C., Sriubolmas, N., 2006. Essential oil of the flowers of Azadirachta indica(Meliaceae). Songklanakarin J. Sci. Technol. 28, 115–119.
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Azadirachta excelsa
|
Stem |
4 Meliacin type limonoids, two novel namely and 2,3-dihydronimbolide and 3-deoxy methyl nimbidate |
Cui et al., 1998Cui, B., Chai, H., Constant, H.L., Santisuk, T., Reutrakul, V., Beecher, C.W.W., Farnsworth, N.R., Cordell, G.A., Pezzuto, J.M., Kinghorn, A.D., 1998. Limonoids from Azadirachta excelsa. Phytochemistry 47, 1283–1287.
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Cabralea canjerana
|
Stem |
Dammarane triterpenes 20S,24S-epoxy-7b,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid, 20S,24S-epoxy-7b,15a,25-trihydroxy-3,4-secodammar-4(28)-en-3-oic acid and 20S,24R-epoxy-7b,22x,25-trihydroxy-3,4-secodammar-4(28)-en-3-oic acid, known dammarane triterpenes ocotillone, eichlerianic acid, shoreic acid and the sterols sitosterol, campesterol, sitostenone stigmasterol, and stigmast-5-en-3-one |
Campos Braga et al., 2006Campos Braga, P.D., Soares, M.S., Silva, M.F.G.F., Vieira, P.C., Fernandes, J.B., Pinheiro, A.L., 2006. Dammarane triterpenes from Cabralea canjerana (Vell.) Mart. (Meliaceae): their chemosystematic significance. Biochem. Syst. Ecol. 34, 282–290.
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|
Branches |
Ocotillone, eichlerianic acid, shoreic acid and eichlerialactone |
Campos Braga et al., 2006Campos Braga, P.D., Soares, M.S., Silva, M.F.G.F., Vieira, P.C., Fernandes, J.B., Pinheiro, A.L., 2006. Dammarane triterpenes from Cabralea canjerana (Vell.) Mart. (Meliaceae): their chemosystematic significance. Biochem. Syst. Ecol. 34, 282–290.
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Capuronianthus mahafalensis
|
Stem barks |
Protolimonoid, capulin |
Fossen et al., 2012Fossen, T., Rasoanaivo, P., Manjovelo, C.S., Raharinjato, F.H., Yahorava, S., Yahorau, A., Wikberg, J.E.S., 2012. A new protolimonoid from Capuronianthus mahafalensis. Fitoterapia 83, 901–906.
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Carapa guianensis
|
Twig |
1,3-Di-benzene carbon amine-2-octadecylic acid-glyceride (new), hexacosanoic acid-2,3-dihydroxy-glyceride (first time from natural source), ursolic acid, naringenin, scopoletin, 3,4-dihydroxymethylbenzoate, 2,6-dihydroxymethylbenzoate, tetratriacontanoic acid, triacontanoic acid. |
Qi et al., 2004Qiu, S.X., Nguyen, V.H., Le, T.X., Gu, J.Q., Lobkovsky, E., Khanh, T.C., Soejarto, D.D.,Clardy, J., Pezzuto, J.M., Dong, Y., Mai, V.T., Le, M.H., Fong, H.H., 2001. A pregnane steroid from Aglaia lawii and structure confirmation of cabraleadiol monoacetate by X-ray crystallography. Phytochemistry 56, 775–780.
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|
Flower oil |
Mexicanolides and phragmalin-type limonoids named Andirolides A, B, C, D, E, F and G, with the known 7-deacetoxy-7-oxogedunin and 6a-acetoxygedunin |
Tanaka et al., 2011Tanaka, Y., Yamada, T., In, Y., Muraoka, O., Kajimoto, T., Tanaka, R., 2011. Absolute stereostructure of Andirolides A-G from the flower of Carapa guianensis (Meliaceae). Tetrahedron 67, 782–792.
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|
Flower oil |
Gedunins andirobin, three mexicanolides, and two phragmalin-type limonoids andirolides H, I, J, K, L, M, N, O, and P |
Tanaka et al., 2012Tanaka, Y., Sakamoto, A., Inoue, T., Yamada, T., Kikuchi, T., Kajimoto, T., Muraoka, O., Sato, A., Wataya, Y., Kim, H.S., Tanaka, R., 2012. Andirolides H-P from the flower of andiroba (Carapa guianensis, Meliaceae). Tetrahedron 68, 3669–3677.
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|
Flower oil |
Gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named andirolides Q, R, S, T, U and V |
Sakamoto et al., 2013Sakamoto, A., Tanaka, Y., Inoue, T., Kikuchi, T., Kajimoto, T., Muraoka, O., Yamada, T., Tanaka, R., 2013. Andirolides Q-V from the flower of andiroba (Carapa guianensis, Meliaceae). Fitoterapia 90, 20–29.
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|
Seeds |
Limonoids, carapanolides A and B |
Inoue et al., 2012Inoue, T., Nagai, Y., Mitooka, A., Ujike, R., Muraoka, O., Yamada, T., Tanaka, R., 2012. Carapanolides A and B: unusual 9,10-seco-mexicanolides having a 2R,9S-oxygen bridge from the seeds of Carapa guianensis. Tetrahedron Lett. 53, 6685–6688.
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Cedrela odorata
|
Leaves |
Tetranor tri tetraterrpenoids, 3-deoxo-3β, 8β epoxy-6,14α, dihydroxy-8,14α-dihydromxi canolide, cedrodorin: 3-deoxo-3β, 8β epoxy-6-14α hydroxy-8,14-dihydro mexicanolide, 6-acetoxy cedrodorin: 3-deoxo-3β, 8β epoxy-6-14α hydroxy-8, 14-dihydromexicanolide, 6-deoxy-9α-hydroxy cedrodorin and 3-deoxo-3β,8β-epoxy-6,9α, 14α-di hydroxy-mexicanolide (9α-hydroxy cedrodorin) |
Veitch et al., 1999Veitch, N.C., Wright, G.A., Stevenson, P.C., 1999. Four new tetranortriterpenoids from Cedrela odorata associated with leaf rejection by Exopthalmus jekelianus. J. Nat.Prod. 62, 1260–1263.
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|
Leaf essential oil |
Sesquiterpenoids: α-santalene, β-acoradiene, β-elemene caryophylleneoxide, Z-α-bergamotene |
Asekun and Ekundayo, 1999Asekun, O.T., Ekundayo, O., 1999. Constituents of the leaf essential oil of Cedrela odorata L. from Nigeria. Flav. Fragr. J. 14, 390–392.
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Stems |
Sesuiterpenes, triterpenes, limonoids and flavonoids |
De Paula et al., 1997De Paula, J.R., Vieira, I.J.C., Das, M.F., Da Silva, M.F., Fo, E.R., Fernandes, J.B., Vieira, P.C., Pinheiro, A., Vilela, E.F., 1997. Sesquiterpenes, triterpenoids, limonoids and flavonoids of Cedrela odoratagraft and speculations on the induced resistanceagainst Hypsipyla grandella. Phytochemistry 44, 1449–1454.
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Stem bark |
Nomilin/obacunol derivatives 11β-acetoxyobacunyl acetate, 11β,19-diacetoxy-l-deacetyi-l-epidihydronomilin, 11β-acetoxyobacunol and odoralide and swietenolide derivative 8β,14α-dihydroswietenolide, and seven known limonoids of two nomilin derivatives, 7-acetyldihydronomilin, and 7-acetyl-11b-acetoxydihydronomilin, five mexicanolides, swietenolide, 3b,6-dihydroxydihydrocarapin, xyloccensin K, 3b-hydroxydihydrocarapin and cedrodorin |
Kipassa et al., 2008Kipassa, N.T., Iwagawa, T., Okamura, H., Doe, M., Morimoto, Y., Nakatani, M.,2008. Limonoids from the stem bark of Cedrela odorata. Phytochemistry 69,1782–1787.
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Bark oil |
Sesquiterpene hydrocarbons and oxygenated sesquiterpenes 43.9%, 42.4% respectively. α-copaene (14.4%), α-cadinol (11.2%), β-eudesmol (9.4%), delta-cadinene (9.2%). |
Martin et al., 2003Martin, A.P., Salgueiro, L.R., Da Cunha, A.P., Vila, R., Canigueral, S., Omi, F., Casanova, J., 2003. Essential oil composition of Eryngium foetidum from S. Tome e Principe. J. Essent. Oil Res. 15, 422–424.
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Heart wood |
3-oxo-threo-23,24,25-tri hydroxy tirucall-7-ene and 3β-O-Δ-glucopyranosyl-24-methylene cholesterol |
Campos et al., 1991Campos, A.M., Oliveira, F.S., Machado, M.I.L., Braz Filho, R., Matos, F.J.A., 1991. Triterpenes from Cedrela odorata. Phytochemistry 30, 1225–1229.
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Cedrela mexicana
|
Leaves and stem bark oil |
Sesquiterpenes α-terpinyl actate spathulenol, elemol, alismol |
Ogunwande et al., 2005Ogunwande, I.A., Ekundayo, O., Olawore, N.O., Adeleke, K.A., 2005. Constituents of the essential oils of the leaves and stem bark of Cedrela mexicana L. grown in Nigeria. J. Essent. Oil Res. 17, 289–291.
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Cedrela salvadorensis
|
Leaves |
Flavonol rhamnosides-(−)-epicatechin, a fzelin and quercitrin |
Barrios-Chica and Castro-Castillo, 1995Barrios-Chica, M., Castro-Castillo, O., 1995. Flavonol rhamnosides from Cedrela salvadorensis leaves. Fitoterapia 66, 92–95.
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Cedrela sinensis
|
Leaves |
Cedrellin and 2,6,10,15-phytatetraene-14-01- |
Luo et al., 2000aLuo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G., 2000a. Limonoids and phytol derivatives from Cedrela sinensis. Fitoterapia 71, 492–496.
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Five limonoids:11β-hydroxy-7α-obacunyl acetate,11-oxo-7α-obacunyl acetate, 11-oxo-7α-obacunol, 11β-hydroxyceneorin G,11-oxocneorin G |
Mitsui et al., 2004Mitsui, K., Maejima, M., Fukaya, H., Hitotsuyanagi, Y., Takeya, K., 2004. Limonoids from Cedrela sinensis. Phytochemistry 65, 3075–3081.
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|
Seeds, leaves, and stems |
Apotirucallane triterpenoids |
Mitsui et al., 2005Mitsui, K., Maejima, M., Saito, H., Fukaya, H., Hitotsuyanagi, Y., Takeya, K., 2005.Triterpenoids from Cedrela sinensis. Tetrahedron 61, 10569–10582.
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Rachis |
Methyl gallate, quercitrin, bis-(p-hydroxy pheny)-ether adenosine, isoquercitrin, rutin, (+)-catechin and (−)-epicatechin |
Park et al., 1996Park, J.C., Yu, Y.B., Lee, J.H., Choi, J.S., Ok, K.D., 1996. Phenolic compounds from therachis of Cedrela sinensis. Korean J. Pharmacogn. 27, 219–223.
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Cedrela tonduzii
|
Leaves |
Quercetin-3-glucoside 2 and robinine |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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Cedrela tubiflora
|
Leaves |
Water-soluble polysaccharide |
Benencia et al., 1999Benencia, F., Rodriguez, M.C., Matulewicz, M.C., Coulombie, F.C., 1999. Neutral polysaccharide from Cedrela tubiflora with anticomplementary activity. Phytochemistry 50, 57–62.
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Cedrelopsis grevei
|
Trunk bark |
Coumarins, 7-methoxy-5-prenyl coumarin (iso cedrelopsin) and 3,′4′-dihydrobraylin, along with five known coumarins (6,7-dimethoxy-5-prenyl coumarin obliquin, 8-methoxy obliquin aesculetin, cedrelopsin and scoparone) |
Um et al., 2003 |
Chisocheton ceramicus
|
Barks |
Limnoid ceramicine A |
Mohamad et al., 2008Mohamad, K., Hirasawa, Y., Lim, C.S., Awang, K., Hadi, A.H.A., Takeya, K., Morita,H., 2008. Ceramicine A and walsogyne A, novel limonoids from two species of Meliaceae. Tetrahedron Lett. 49, 4276–4278.
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Chisocheton erythrocarpus
|
Barks |
Limonoids, erythrocarpines A-E |
Awang et al., 2007Awang, K., Lim, C.S., Mohamad, K., Morita, H., Hirasawa, Y., Takeya, K., Thoison, O., Hadi, A.H.A., 2007. Erythrocarpines A-E, new cytotoxic limonoids from Chisocheton erythrocarpus. Bioorg. Med. Chem. Lett. 15, 5997–6002.
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Limonoids, malayanine A and malayanine B |
Chong et al., 2012Chong, S.L., Awang, K., Martin, M.T., Mokhtar, M.R., Chan, G., Litaudon, M., Gueritte, F., Mohamad, K., 2012. Malayanines A and B, two novel limonoids from Chisocheton erythrocarpus Hiern. Tetrahedron Lett. 53, 5355–5359.
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Chisocheton paniculata
|
Fruit |
Meliacin 1,2-dihydro-6-acetoxy azadirone |
Bordoloi et al., 1993Bordoloi, M., Saikia, B., Mathur, R.K., Goswami, B.N., 1993. A meliacin from Chisocheton paniculatus. Phytochemistry 34, 583–584.
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Whole plant |
Protolimonoids and limonoids arunachalin |
Yadav et al., 1999Yadav, R.D., Kataky, J.C.S., Mathur, R.K., 1999. New protolimonoids and limonoids: Part III-Arunachalin, a new tetranortriterpenoid from Chisocheton paniculatus Hiern (Meliaceae). Ind. J. Chem. 38, 243–245.
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Chisocheton polyandrus
|
Leaves |
Dammarane triterpenoids, dammara-20,24-dien-3-one and 24-hydroxydammara-20,25-dien-3-one |
Chan et al., 2012Chan, K.Y., Mohamad, K., Ooi, A.J.A., Imiyabir, Z., Chung, L.Y., 2012. Bioactivity-guided fractionation of the lipoxygenase and cyclooxygenase inhibiting constituents from Chisocheton polyandrus Merr. Fitoterapia 83, 961–967.
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Chisocheton tomentosus
|
Bark |
7α-Hydroxy-β-sitosterol (new), stigmasta-4,6-diene-3-one, stigmasterol and β-sitosterol |
Najmuldeen et al., 2011Najmuldeen, I.A., Hadi, A.H.A., Mohamad, K., Awang, K., Nasab, M.F., Ketuly, K.A., Mukhtar, M.R., Morita, H., 2011. Steroids from Chisocheton tomentosus. Malaysian J. Sci. 30, 144–153.
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Chukrasia tabularis
|
Leaves |
Sitosterol, melianone, scopoletin, 6-7-dimethoxy coumarin, quercetin and its 3-galactoside and tannic acid |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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Wood |
Meliacins, chukrasin A, B, C, D and E |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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Stem bark |
Phragmalin-type limonoids, tabulalin F |
Jun et al., 2011Jun, L., Jun-Song, W., Wen-Jun, C., Ling-Yi, K., 2011. A New phragmalin-type limonoid from Chukrasia tabularis var. velutina. Chin. J. Nat. Med. 9, 98–100.
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19-nor limonoid incorporating a unique 7,10-c-lactone tabulvelutin A, tabulvelutin B |
Yin et al., 2011Yin, J.L., Di, Y.T., Fang, X., Liu, E.D., Liu, H.Y., He, H.P., Li, S.L., Li, S.F., Hao, X.J., 2011. Tabulvelutin A, the first 19-nor limonoid with unprecedented ring system from Chukrasia tabularis var. velutina. Tetrahedron Lett. 52, 3083–3085.
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|
Root bark |
Phragmalin limonoids tabulalin and tabulalides A-E |
Nakatani et al., 2004Nakatani, M., Abdelgaeil, S.A.M., Saad, M.M.G., Huang, R.C., Doe, M., Iwagawa, T., 2004. Phragmalin limonoids from Chukrasia tabularis. Phytochemistry 65, 2833–2841.
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Seeds |
3,30-Isobutyrate, 3-isobutyrate, 30-propionate of phragmalin, 12-acetoxy phragmalin |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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|
|
Linoleic, linolenic acid |
Goel, 1998Goel, C.L., 1998. Characteristics and fatty acid composition of potential Chukrasia tabularis seed oil. Van. Vigyan. 36, 8–11.
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Cipadessa baccifera
|
Leaves |
Cipadessi n-type limonoids, cipaferens A-D, and asmelianodiol, spicatin |
Siva et al., 2013aSiva, B., Suresh, G., Poornima, B., Venkanna, A., Babu, K.S., Prasad, K.R., Reddy, L.P.A., Sreedhar, A.S., Rao, C.V., 2013a. Cipadessin-type limonoids from the leaves of Cipadessa baccifera. Tetrahedron Lett. 54, 2934–2937.
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Seeds |
Cipadesin, 17α, 20R-dihydroxy pregnan-3,16-dione, 1,4-epoxy-16-hydroxy heneicos-1,3,12,14,18-pentaene and 1,4-epoxy-16-hydroxy heneicos-1,3,12,14-tetraene |
Luo et al., 2000b |
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Cipadesin and febrifugin |
Marpaung et al., 2001Marpaung, L., Nakamura, N., Kakula, H., Hattori, M., 2001. Absolute configuration of cipadesin and febrifugin from the seeds of Cipadessa baccifera. Nat. Med. 55,220–226.
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Methyl angolensate type cipaferen E-J and three new mexicanolide-typelimonoids cipaferen K-M |
Siva et al., 2013bSiva, B., Poornima, B., Venkanna, A., Prasad, K.R., Sridhar, B., Nayak, V.L., Ramakrishna, S., Babu, K.S., 2013b. Methyl angolensate and mexicanolide-type limonoids from the seeds of Cipadessa baccifera. Phytochemistry 98, 174–182.
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Cipadessa boivinina
|
Stem bark |
Sesquiterpenoid; boivinianin A (11,12,13-trisnorbisabola-1,3,5-trien-10,7-olide); boivinianin B (7,10-epoxy-1,3,5-bisabolatrien-11-ol); 4-hydroxy-4,7-dimethyl-1-tetralone |
Mulholland et al., 2006Mulholland, D.A., McFarland, K., Randrianarivelojosia, M., 2006. Sesquiterpenoid derivatives from Cipadessa boiviniana(Meliaceae). Biochem. Syst. Ecol. 34,365–369.
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Dysoxylum beddomei
|
Leaves |
Beddomeilactone, beddomeilactone together with six known triterpenoids (3-oxo tirucalla-7,24-dien-23-ol, dipterocarpol, niloticin, melianone, melianodiol and 24-epi-melianodiol) |
Hisham et al., 2004Hisham, A., Jayakumar, G., Bai, M.D.A.S., Fujimoto, Y., 2004. A new triterpenoids from Dysoxylum beddomei. Nat. Prod. Res. 18, 329–334.
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Dysoxylum binectariferum
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Stem bark |
Rohitukine |
Mohanakumara et al., 2010Mootoo, B.S., Ali, A., Motilal, R., Pingal, R., Ramlal, A., Khan, A., Reynolds, W.F., McLean, S., 1999. Limonoids from Swietenia macrophylla and S. aubrevilleana. J. Nat. Prod. 62, 1514–1517.
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Dysoline, a regioisomer of rohitukine and rohitukine-N-oxide |
Jain et al., 2013Jain, S.K., Meena, S., Qazi, A.K., Hussain, A., Bhola, S.K., Kshirsagar, R., Pari, K., Khajuria, A., Hamid, A., Shaanker, R.U., Bharate, S.B., Vishwakarma, R.A., 2013. Isolation and biological evaluation of chromone alkaloid dysoline, a new regioisomer of rohitukine from Dysoxylum binectariferum. Tetrahedron Lett. 54, 7140–7143.
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Dysoxylum cumingianum
|
Leaves |
Triterpenes cumingianol A-E and a triterpene glucoside Cumingianoside R and hispidol B, 21-O-methyltoosendanpentol andagladupol A |
Kurimoto et al., 2011Kurimoto, S., Kashiwada, Y., Lee, K.H., Takaishi, Y., 2011. Triterpenes and a triterpene glucoside from Dysoxylum cumingianum. Phytochemistry 72, 2205–2211.
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Dysoxylum densiflorum
|
Twigs leaves |
Three degraded limonoids, dysodensiols A-C, and three sesquiterpenoids, dysodensiols D-F, along with seventeen known compounds |
Xie et al., 2008Xie, B.J., Yang, S.P., Yue, J.M., 2008. Terpenoids from Dysoxylum densiflorum. Phytochemistry 69, 2993–2997.
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Dysoxylum grande
|
Leaves |
23-Oxo-cholestane derivatives grandol A-G along with a new 3, 4-secodammar-4(28)-en-3-oic acid derivative |
Wah et al., 2013Wah, L.K., Abas, F., Cordell, G.A., Ito, H., Ismail, I.S., 2013. Steroids from Dysoxylum grande (Meliaceae) leaves. Steroids 78, 210–219.
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Dysoxylum hainanense
|
Bark |
Tirucallane derivatives. 3β, 22S-dihydroxy tirucalla-7,24-dien-23-one, 22,23-epoxy-tirucalla-7-ene-3β, 24,25-triol, 3β,25-dihydroxy-tirucalla-7,23-diene, 23,26-dihydroxy-tirucalla-7,24-diene-3 |
Luo et al., 2000cLuo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G., 2000c. Tirucallane triterpenoids from Dysoxylum hainanensis. Phytochemistry 54, 801–805.
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Ent-pimarene diterpenoids, ent-18-acetoxy-8(14)-pimarene-15S, 16-diol, ent-18-acetoxy-16-hydroxy-8(14)-pimarene-15-one, ent-16, 18-hydroxy-8(14)-pimarene-15-one, ent-19-nor-4,16, 18-trihydroxy-8(14)-pimarene-15-one together with three known damarane triterpenoids, richenoic acid, eichlerianic acid and shoreic acid. |
Luo et al., 2001Luo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G., 2001. Ent-Pimarane derivatives from Dysoxylum hainanense. Phytochemistry 57, 131–134.
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Apo-tirucallols 7α-acetoxyl-17α-20S-21,24-epoxy-apotirucall-14-ene-3α,23R,24S,25-tetraol (2), 7α-acetoxyl-17α-20S-21,24-epoxy-apotirucall-14-en-3-one-23R,24S,25-triol |
Luo et al., 2002Luo, X.D., Wu, S.H., Wu, D.G., Ma, Y.B., Qi, S.H., 2002. Three new apotirucallols with six-membered hemiacetal from Meliaceae. Tetrahedron 58, 6691–6695.
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Nor-dammarane triterpenoids, 12β-O-acetyl-15α, 28-dihydoxy-17β-methoxy-3-oxo-20,21,22–23,24,25,26,27-octanordammanran, 12β-O-acetyl-15α,17β,28-trihydoxy-3-oxo-20,21,22–23,24,25,26,27-octanordammanran, 12β-O-acetyl-15α,28-dihydoxy-3-oxo-17-en-20,21,22–23,24,25,26,27-ctanordammanran, and 12β,15α,17β,28-tetrahydoxy-3-oxo-20,21,22–23,24,25,26,27-octanordammanran |
Wang and Guan, 2012Wang, F., Guan, Y., 2012. Cytotoxic nor-dammarane triterpenoids from Dysoxylum hainanense. Fitoterapia 83, 13–17.
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Dysoxylum kuskusense
|
Fruits |
Prenyleu desmane diterpenes, dysokusone I and dysokusone E |
Duh et al., 2000Duh, C.Y., Wang, S.K., Chen, I.S., 2000. Cytotoxic prenyleudesmane diterpenes fromthe fruits of Dysoxylum kuskusense. J. Nat. Prod. 63, 1546–1547.
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Dysoxylum lenticellare
|
Stem |
2α-methoxycomosivine, 2α-methoxy lenticellarine and 2α-hydroxylenticellarine |
Aladesanmi and Hoffmann, 1994Aladesanmi, A.J., Hoffmann, J.J., 1994. Additional alkaloids from the stem of Dysoxylum lenticellare. Phytochemistry 35, 1361–1362.
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|
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Biflavonoid, robusta flavone 4′,7″-dimethyl ether, Isoginkgetin, bilobetin |
He et al., 1996He, K., Timmerman, B.N., Aladesanmi, A.J., Zeng, L., 1996. A biflavonoid from Disoxylum lenticellare Gillespie. Phytochemistry 42, 1199–1201.
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Dysoxylum macranthum
|
Bark |
Triterpenes, dymacrins, A-Ktetracyclic terpenes and pregnane steroids |
Mohammad et al., 1999Mohammad, K., Martin, M.T., Najdar, H., Gaspard, C., Sevenet, T., Awang, K., Pais, M.,1999. Cytotoxic 3,4-secoapotirucallanes from Aglaia argentea Bark. J. Nat. Prod.62, 868–872.b |
Dysoxylum malabaricum
|
Leaves |
Dammarane triterpenoid dymalol (20S,24R)-epoxy-4-hydroxy-3,4-secodammaran-3-oic acid methyl ester (along with two known dammarane triterpenoids) |
Govindachari et al., 1994Govindachari, T.R., Suresh, G., Krishna kumara, G.N., 1994. Triterpenoids from Dysoxylum malabaricum. Phytochemistry 37, 1127–1129.
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Ergostane, ergosta 5,24 (24′)-diene-3β,4β, 20s-triol, (24R)-cycloartane-3β-24,25-triol and ergosta-5,24 (24′)-diene-3β, 7β-diol |
Govindachari et al., 1997Govindachari, T.R., Krishna Kumari, G.N., Suresh, G., 1997. Ergosta-5,24(24')-diene-3β,4β,20S-triol, an ergostane steroid from Dysoxylum malabaricum. Phytochemistry 44, 153–155.
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Terpenes, 21R,23R-epoxy-21α-ethoxy-24S-25-dihydroxyapotirucall-7-en-3one 24R-acetoxy-3β,25-dihydroxy cycloartane |
Hisham et al., 2001Hallur, G., Sivaramakrishnan, A., Bhat, S.V., 2002. Three new tetranortriterpenoids from neem seed oil. J. Nat. Prod. 65, 1177–1179.
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Dysoxylum mollissimum
|
Leaves |
Glabretal-type triterpenoids dysoxylumglabretol A (1a-1b), dysoxylumglabretol B (2a-2b) along with the known compounds, 24,25-epoxy-3b,23-dihydroxy-7-tirucallene (3), squalene, polyprenol, linoleic acid and lutein |
Ragasa et al., 2013Ragasa, C.Y., Torres, O.B., Shen, C., Gayle, M.M.R., Joyce, F.R., Jacinto, S.D., 2012. Chemical constituents of Aglaia loheri. Phcog. J. 4, 29–31.
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Dysoxylum muelleri
|
Wood |
Glabretal triterpenoids: Three dysoxins and also 6α-acetoxy-obacunone acetate (limonoid) |
Mulholland et al., 1996Mulholland, D.A., Nair, J.J., Taylor, D.A.H., 1996. Astrotrichilin, alimonoid from Astrotrichilia asterotricha. Phytochemistry 42, 1239–1241.
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Dammarane triterpenoids cabraleone, and richenone |
Mulholland and Naidoo, 2000Mulholland, D.A., Naidoo, N., 2000. Dammarane triterpenoids from Dysoxylum muellerii. Biochem. Syst. Ecol. 28, 295–297
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Dysoxylum richii
|
Leaves |
Dammarane triterpenoids |
Aalbersberg and Singh, 1991Aalbersberg, W., Singh, Y., 1991. Dammarane triterpenoids from Discoxylum richii. Phytochemistry 30, 921–926.
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Dysoxylum schiffneri
|
Wood |
Sesquiterpenoids (+)-8-hydroxy calamene, schiffnerone A (1,5-dihydroxy-1,3,5-bisabolatrien-10-one), trisa oresquiterpenoid, schiffnerone B (2-hydroxy-11,12,13-trinor-7-calamenone) |
Mulholland et al., 1998aMulholland, D.A., Iourine, S., Taylor, D.A.H., 1998a. Sesquiterpenoids from Dysoxylum schiffneri. Phytochemistry 47, 1421–1422.
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Dysoxylum spectabile
|
Bark |
Pimaradiene compounds, 6α-acetoxyobacunol acetate, methyl ivorensate, isopimara-8(14),15-diene, and 7α-hydroxyisopimara-8(14),15-diene |
Mulholland et al., 1999bMulholland, D.A., Monkhe, T.V., Pegel, K.H., Taylor, D.A.H., 1999b. Limonoids and diterpenoids from Dysoxylum spectabile(Meliaceae). Biochem. Syst. Ecol. 27, 313–315.
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Ekbergia benuguelensis
|
Root bark |
4-Methoxy-5-hydroxy methyl coumarin, together with poly hydroxy squalenes. 2,3,22,23-tetrahydroxy-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetra cosa tetraene and 2-hydroxymethyl-2,3,22,23-tetrahydroxyl-6,10,15,19,23-penta methyl-6,10,14,18-tetracosatetraene |
Jonker et al., 1997Jonker, S.A., Nkunya, M.H.H., Mwamtobe, L., Geenevasen, J., Koomen, G.J., 1997. A new coumarin and polyhydroxysqualenes from Ekebergia benguelensis. Nat. Prod. Lett. 10, 245–248.
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Ekbergia capensis
|
Dried bark |
Triterpenoids, 2,3,22,23-tetra hydroxy 2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraene and 2-hydroxy, methyl-23,22,23-tetrahydroxy 6,10,15,19,23-penta methyl-6,10,14,18-tetra cosa tetraene |
Nishiyama et al., 1996Nishiyama, Y., Moriyasu, M., Ichimaru, M., Tachibana, Y., Kato, A., Mathenge, S.G., Nganga, J.N., Juma, F.D., 1996. Acyclic triterpenoids from Ekebergia capensis. Phytochemistry 42, 803–807.
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|
Seed |
Capensolactones 1-3 and methyl 3α-hydroxy-3-deoxy angolensate |
Mulholland and Iourine, 1998Mulholland, D.A., Iourine, S.E., 1998. Limonoids from Ekebergia capensis. Phytochem-istry 47, 1357–1361.
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Ekebergia pterophylla
|
Leaves |
Lupeol |
Mulholland et al., 1998bMulholland, D.A., Iourine, S.E., Taylor, D.A.H., Dean, F.M., 1998b. Coumarins from Ekebergia pterophylla. Phytochemistry 47, 1641–1644.
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|
Bark |
Pterophyllins 1 and 2 and known atraric acid, β-amyrin, β-amyrone, oleanonic acid, β-sitosterol, β-sitosteryl acetate and the |
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Wood |
Pterophyllins 3-5 |
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Entandrophragma angolense
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Leaves |
Tirucallane triterpenoidal compounds 3,23-dioxotirucalla-7,24-dien-21-al, 3,4-secotirucalla-23-oxo-4(28),7,24-trien-21-al-3-oic acid and 3,4-secotirucalla-23-oxo-4(28),7,24-trien-3,21-dioic acid (21-methyl ester) |
Orisadipe et al., 2005Orishadipe, A.T., Ibekwe, N.N., Adesomoju, A.A., Okogun, J.I., 2012. Chemical composition and antimicrobial activity of the seed oil of Entandrophragma angolense (Welw) C.DC. Afr. J. Pure Appl. Chem. 6, 184–187.
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Root bark |
Two gedunin type limonoids 5-hydroxy-7-deacetoxy-7-oxogedunin and 5,6-dehydro-7-deacetoxy-7-oxogedunin, and three methyl angolensate derivatives, 6-deacetoxydomesticulide D, 6-deacetoxydomesticulide D 21-methylether, and entangosin, together with known compounds, methyl angolensate, 6-acetoxymethyl angolensate and secomahoganin |
Nsiama et al., 2011Nsiama, T.K., Okamura, H., Hamada, T., Morimoto, Y., Doe, M., Iwagawa, T., Nakatani,M., 2011. Rings D-seco and B,D-seco tetranortriterpenoids from root bark of Entandrophragma angolense. Phytochemistry 72, 1854–1858.
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Entandrophragma cylindricum
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Bark |
Sesquiterpenes 3-hydroxy-copa-2-en (oil) and 2α-hydroxy-copa-3-en |
Daniewski et al., 1996Daniewski, W.M., Anczewski, W., Gumulka, M., Danikiewicz, W., Jacobson, U., Norin, T., 1996. Sesquiterpenoid constituents of Entandrophragma cylindricum. Phytochemistry 43, 811–814.
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Acyclic triterpene derivatives named sapelenins G-J, along with eight known compounds, sapelenins A-D, ekeberin D2, (+)-catechin and epicatechin and anderolide G |
Kouam et al., 2012Kouam, S.F., Kusari, S., Lamshöft, M., Tatuedom, O.K., Spiteller, M., 2012. Sapelenins G-J, acyclic triterpenoids with strong anti-inflammatory activities from the barkof the Cameroonian medicinal plant Entandrophragma cylindricum. Phytochem-istry 83, 79–86.
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Entandrophragma delevoyi
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Stem bark |
Delevoyin A (3,4-secotirucallane 4 (28),3-oic acid) and delevoyin B (6α-acetoxykinadealactone) |
Mulholland et al., 1994Mulholland, D.A., Osborne, R., Roberts, S.L., Taylor, D.A.H., 1994. Limonoids and triterpenoid acids from the bark of Entandrophragma delevoyi. Phytochemistry 37, 1417–1420.
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Bark |
Acyclic triterpenoid, sapelenin D |
Ngnokam et al., 1995Ngnokam, D., Massiot, G., Bilard, C., Tsamo, E., 1995. Sapelenin D, a new acyclic triterpenoid from the stem bark of Entandrophragma cylindricum. Nat. Prod. Lett. 5, 289–293.
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A novel tetranortriterpenoid, delevoyin C. |
Mulholland et al., 2000bMulholland, D.A., Schwikkard, S.L., Sandor, P., Nuzillard, J.M., 2000b. Delevoyin C, a tetranortriterpenoid from Entandrophragma delevoyi. Phytochemistry 53, 465–468.
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Wood |
Gedunin and 11β-acetoxygedunin |
Mulholland et al., 2000bMulholland, D.A., Schwikkard, S.L., Sandor, P., Nuzillard, J.M., 2000b. Delevoyin C, a tetranortriterpenoid from Entandrophragma delevoyi. Phytochemistry 53, 465–468.
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Entandrophragma utile
|
Bark |
A new heptanortriterpenoid, entilin D |
Daniewski et al., 1995Daniewski, W.M., Gumulka, M., Danikiewicz, W., Sitkowski, J., Jacobsson, U., Norin, T., 1995. Entilin D, a heptanortriterpenoid from the bark of Entandrophragma utile. Phytochemistry 40, 903–905.
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New sterol, 7α,20(S)-dihyroxy-4,24 (28)-er-gostadien-3-one |
Tchouankeu et al., 1996Tchouankeu, J.C., Nyasse, B., Tsamo, E., Connolly, J.D., 1996. 7-Alpha, 20(S)-dihydroxy-4,24(28)-ergostadien-3-one from Entandrophragma utile. J. Nat. Prod.59, 958–959.
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Guarea macrophylla
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Leaves |
Terpenes guai-6-en-10β-ol, isopimara-7,15-dien-2α-ol and cycloarta-23,25-dien-3-one. |
Lago et al., 2000Lago, J.H.G., Brochini, C.B., Roque, N.F., 2000. Terpenes from leaves of Guarea macro-phylla (Meliaceae). Phytochemistry 55, 727–731.
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Cycloartane triterpenoids including two new derivatives 22,25-dihydroxy-cycloart-23E-en-3-one and 24-methylenecycloartane-3b,22-diol |
Lago et al., 2002aLago, J.H.G., Brochini, C.B., Roque, N.F., 2002a. Terpenoids from Guarea guidonia Phytochemistry 60, 333–338.
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|
Leaves essential oil |
Terpenes: one monoterpene, 16 sesquiterpenes and 6 diterpenes |
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Leaves oil |
Sesquiterpenes identified including hydrocarbon and oxygenated derivatives |
Lago et al., 2005Lago, J.H.G., Cornello, M.L., Moreno, P.R.H., Apel, M.A., Limberger, R.P., Henriques,A.T., Roque, N.F., 2005. Sesquiterpenes from essential oil from fruits of Guarea macrophylla Vahl ssp. tuberculata (Meliaceae). J. Essent. Oil Res. 17, 84–85.
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Stem bark |
Caryophyllene oxide, guai-6-en-10 β-ol, sphathulenol, aromadendrane-4α,10β-diol, aromadendrane-4α,10α-diol, alloaromadendrane-4α,10β diol, steroids: sitosterol and stigmasterol |
Lago et al., 2002aLago, J.H.G., Brochini, C.B., Roque, N.F., 2002a. Terpenoids from Guarea guidonia Phytochemistry 60, 333–338.
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|
Bark volatile oil |
17 Sesquiterpenes, one diterpene and four fatty acids |
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Guarea guidonia
|
Volatile oil |
Sesquiterpene (2S*)-eudesma-5,7-dien-2-ol |
Lago et al., 2002bLago, J.H.G., Reis, A.A., Roque, N.F., 2002b. Chemical composition from volatile oil ofthe stem bark of Guarea macrophylla Vahl. ssp. tuberculata Vellozo (Meliaceae).Flavour Frag J. 17, 255–259.
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|
Leaves |
Triterpenes (23S*)-cycloart-24-ene-3b,23-diol and (23R*)-cycloart-24-ene-3b,23-diol |
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Wood bark |
Limonoid (mombasol) acoumari (scopoletin) and sesquiterpenes |
Garcez et al., 1998Garcez, F.R., Nunez, C.V., Garcez, W.S., Roque, N.F., 1998. Sesquiterpenes, limonoid and coumarin from the wood bark of Guarea guidonia. Planta Med. 64, 79–80.
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Stem bark oil |
Sesquiterpenes, β-caryophyllene, germacrene |
Nunez and Roque, 1999Nunez, C.V., Roque, N.F., 1999. Sesquiterpenes from the stem bark of Guarea guidonia (L.) Sleumer (Meliaceae). J. Essent. Oil Res. 11, 439–440.
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Guarea rhophalocarpa
|
Leaves |
Terpenes including two sandara copimaradiene diterpenoids, ent-8-(14), 15-sandaracopimaradiene-2α,18-dioland ent-8-(14),15-sandaracopimaradiene-2β 18-dioland two lanostane triterpenoids,23-hydroxy-5α-lanosta 7,9(11),24-triene-3-one and 5α-lanosta-7,9(11),24-triene-3α,23-diol |
Del Rayo et al., 2001Del Rayo, C.M., Phillipson, J.D., Croft, S.L., Kirby, G.C., Warhurst, D.C., Solis, P.N., 2001. Terpenoids from Guarea rhophalocarpa. Phytochemistry 56, 203–210.
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Guarea trichilioides
|
Dried leaves |
Cycloartane derivatives-cycloart-24-en-3,23-dione, 23-hydroxycycloart-24-en-3-one (epimers), 3β-hydroxycycloart-24-ene-23-one, 25-hydroxycycloart-23-en-3-one, 3β-21-dihydroxycycloartane, 3β-21,22,23-tetra hydroxycycloartane-24 (31)25-diene |
Furlan et al., 1993Furlan, M., Roque, N.F., Wolter-Filho, W., 1993. Cycloartane derivatives from Guarea trichilioides. Phytochemistry 32, 1519–1522.
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Leaves |
Diterpenoids including four labdane and two clerodane derivatives |
Furlan et al., 1996Furlan, M., Lopes, M.N., Fernandes, J.B., Pirani, J.R., 1996. Diterpenes from Guarea trichilioides. Phytochemistry 41, 1159–1161.
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Fruits |
Diterpenoids including four labdane and two clerodane derivatives |
Wolter et al., 1993Wolter, E.L.A., da Rocha, A.F.L., Wolter Filho, W., Peureira Junior, O.L., Siqueira, J.B.G., Zoghbi, M., Das, G.B., 1993. Chemical study of fruits and steam bark of Guarea trichilioides, Meliaceae. Acta Amaz. 23, 177–180.
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Khaya anthotheca
|
Stems |
Acyl peroxylated and seco-mexicanolides 1α,8α-oxido-3β-acetoxy-2α, 14α-dihydroxy-{3,3.110,2}-bicyclo meliac-7,19-olide and 3-acetoxy 8,14-dien-8,30-sec-khayalactone, methyl 1 α, 2β 3α, 6,8α, 14β-hexahydroxy {4.2.110.30. 11,4}-tricyc lomeliac-7-oate scopoletin and 3-β-d-gluco pyranosyl sitosterol |
Ferreira et al., 2005Ferreira, I.C.P., Cortez, D.A.G., Da Silva, M.F.G.F., Fo, E.R., Vieira, P.C., Fernandes, J.B., 2005. Acylperoxylated and seco-mexicanolides from stems of Khaya anthotheca. J. Nat. Prod. 67, 413–416.
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|
Stem bark |
Anthothecanolide, 3-O-acetyl anthothecanolide, 2,3-di-O-acetyl anthothecanolide, 6R, 8α-dihydroxycarpin, 3β-acetoxy-3-deoxo-6Rhydroxycarpin, methyl angolensate, methyl 6-hydro angolensate, khayalactone |
Tchimene et al., 2005Tchimene, M.K., Tane, P., Ngamga, D., Connolly, J.D., Farrugia, L.J., 2005. Four triterpenoids from stem bark of Khaya anthotheca. Phytochemistry 66, 1088–1093.
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Khaya grandifoliola
|
Trunk bark |
A,B,D-Secolimonoid, khaya lactone (C27H34O9) |
Tchuendem et al., 1998Tchuendem, M.H.K., Ayafor, J., Connolly, F., Sterner, O., 1998. Khayalactone, a novel limonoid from Khaya grandifoliola. Tetrahedron Lett. 39, 719–722.
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|
Stem bark |
Deacetylkhayanolide E, 6S-hydroxykhayalactone, and grandifolide A and khayanolide A, anthothecanolide, 3-O-acetylanthothecanolide |
Zhang et al., 2008Zhang, H., Odeku, O.A., Wang, X.N., Yue, J.M., 2008. Limonoids from the stem bark of Khaya grandifoliola. Phytochemistry 69, 271–275.
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Khaya ivorensis
|
Seeds |
Limonoid |
Vanucci et al., 1992Vanucci, C., Lange, C., Lhommet, G., Dupont, B., Davoust, D., Vauchot, B., Clement, J.L., Brunk, F., 1992. An insect antifeedant limonoid from seed of Khaya ivorensis. Phytochemistry 31, 3003–3004.
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|
Stems |
1-O-Deacetyl-6-deoxykhayanolide E, 1-O-deacetyl-2a-hydroxykhayanolide E, 3-acetyl-khayalactone, 11a-acetoxy-2a-hydroxy-6-deoxy-destigloylswietenine acetate, |
Zhang et al., 2009Zhang, B., Yang, S.P., Yin, S., Zhang, C.R., Wu, Y., Yue, J.M., 2009. Limonoids from Khaya ivorensis. Phytochemistry 70, 1305–1308.
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Khaya senegalensis
|
Stem bark |
Rings B and D opened limonoids, rings B and D opened limonoids, khayanone and 2-hydroxy seneganolide and phragmalin limonoid 1-O-acetyl khayanolide |
Nakatani et al., 2001Nakatani, M., Abdelgaeil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., Doe, M.,2001. Antifeedant rings B and D opened limonoids from Khaya senegalensis. J. Nat. Prod. 65, 1261–1265.
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Phragmalin-type limonoids, khayanolides A, B and C, four B,D-seco compounds, seneganolide, methyl angolensate and its 6-hydroxy and 6-acetoxy derivatives |
Abdelgaleil et al., 2001Abdelgaleil, S.A., Okamura, H., Iwagawa, T., Sato, A., Miyahara, I., Doe, M., Nakatani,M., 2001. Khayanolides rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron 57, 119–126.
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B/D opened limonoids, phragmalin limonoids khayanolides D and E and one limonoid glucoside, khayanoside |
Nakatani et al., 2002Nakatani, M., Abdelgaeil, S.A.M., Kassem, S.M.I., Takezaki, K., Okamura, H., Iwagawa, T., Doe, M., 2002. Three new modified limonoids from Khaya senegalensis. J. Nat. Prod. 65, 1219–1221.
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|
Bark |
2,6-Dihydroxy fissionolide |
Khalid et al., 1998Khalid, S.A., Friendrichsen, G.M., Kharazmi, A., Theander, T.G., Olsen, C.E., Christensen, S.B., 1998. Limonoids from Khaya senegalensis. Phytochemistry 49, 1769–1772.
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|
|
Tetranottriterpenoids of mexicanolide type: 2-hydroxymexicanolide, 6-deoxy destigloylswietenine, 2,3-dihydroxy-3-deoxymexicanolide |
Govindachari et al., 1998Govindachari, T.R., Krishna Kumari, G.N., 1998. Tetranortriterpenoids from Khaya senegalensis. Phytochemistry 47, 1423–1425.
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|
Leaves |
Methyl-1α-acetoxy-3β,6,8α-trihydroxy-2α-methoxy-2β,14β-epoxy-tricyclomeliac-7-oateand methyl 1α-acetoxy-6,8α, 14β,30β-tetrahydroxy-3-oxo-tricyclomelin-C-7-oate |
Olmo et al., 1997Olmo, L.R.V., Da Silva, M.F.D.G.F., Fo, E.R., Vieira, P.C., Fernandes, J.B., Pinheiro, A.L., Vilela, E.F., 1997. Limonoids from leaves of Khaya senegalensis. Phytochemistry 44, 1157–1161.
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|
Seeds |
Mexicanolide tetranortriterpenoids 2-hydroxymexicanolide, 6-deoxydestigloylswietenine and 2,3-dihydroxy-3-deoxymexicanolide. In addition, mexicanolide, 3β-hydroxy-3-deoxymexicanolide, 3β-hydroxy-3-deoxycarapin, 6-hydroxy methyl angolensate, 3-acetyl-7-keto khivorin, 3-deacetyl khivorin and 3,7-dideacetyl khivorin |
Govindachari and Krishna Kumari, 1998Govindachari, T.R., Suresh, G., Gopalakrishnan, G., Banumathy, B., Masilamani, S.,1998. Identification of antifungal compounds from the seed oil of Azadirachta indica. Phytoparasitica 26, 106–109.
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Malleastrum antsingyense
|
Stem bark |
Vilasinin limonoids 1,3-diacetylvilasinin, 1,3-diacetyl-12a-hydroxy-7-tigloylvilasinin |
Coombes et al., 2008Coombes, P.H., Mulholland, D.A., Randrianarivelojosia, M., 2008. Vilasinin limonoidsfrom Malleastrum antsingyense J.F. Leroy (Meliodeae: Meliaceae). Biochem. Syst.Ecol. 36, 74–76.
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Melia azedarach
|
Leaves |
Meliacarpin derivatives (C-seco limonoids) 1,3-dicinnamoyl-11-hydroxymeliacarpin,1-cinnamoyl-3-methacrylyl-11-hydroxy-meliacarpin and 1-cinnamoyl-3-acetyl-11-hydroxymeliacarpin. |
Bohnenstengel et al., 1999Bohnenstengel, F.I., Wray, V., Witte, L., Srivastava, R.P., Proksch, P., 1999. Insecticidal meliacarpins (C-seco limonoids) from Melia azadarach. Phytochemistry 50, 977–982.
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|
|
Dipenta decylketone, glycerol 1,3-bis-undec-9-enoate 2-do-dec-9-enoateand glycerol tris-tri dec-9-enoate |
Suhag et al., 2003Siva, B., Poornima, B., Venkanna, A., Prasad, K.R., Sridhar, B., Nayak, V.L., Ramakrishna, S., Babu, K.S., 2013b. Methyl angolensate and mexicanolide-type limonoids from the seeds of Cipadessa baccifera. Phytochemistry 98, 174–182.
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|
Steroids (20S)-5,24(28)-ergostadiene-3α,7α,16β,20-tetrol (1), (20S)-5-ergostene-3β,7α,16β,20-tetrol (2), and 2α,3β-dihydro-5-pregnen-16-one and 5-stigmastene-3β,7α, 20-triol, 5-stigmastene-3β,7α-diol, and 2α,3α,16β-trihydroxy-5α-pregnane 20R-methacrylate |
Wu et al., 2009Wu, S.B., Ji, Y.P., Zhu, J.J., Zhao, Y., Xia, G., Hu, Y.H., Hu, J.F., 2009. Steroids from the leaves of Chinese Melia azedarachand their cytotoxic effects on human cancer cell lines. Steroids 74, 761–765.
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|
Stem |
12-hydroxy amoora statone, 12-hydroxy amoora statin, 12-acetooxy amoora statin |
Ahn et al., 1994Ahn, J.W., Choi, S.U., Lee, C.O., 1994. Cytotoxic limonoids from Melia azedarachvar japonica. Phytochemistry 36, 1493–1496.
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|
Roots |
Teracrylmelazolide A, melazolide A and teracrylmelazolide B |
Ambrosio and Guerriero, 2002Ambrosio, D., Guerriero, A., 2002. Degraded limonoids from Melia azedarach and biogenetic implications. Phytochemistry 60, 419–424.
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|
|
Limonoids, azecins 1, 2, 3 and 4 |
Srivastava and Gupta, 1985Srivastava, S.K., Gupta, H.O., 1985. New limnoids from the roots of Melia azedarah Linn. Indian J. Chem. Sect. B 24, 166–170.
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|
Root bark |
Azadararide 12α-acetoxy fraxinellone, fraxinellone, fraxinellonone |
Nakatani et al., 1998Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., Huang, R.C., 1998. Degraded limonoids from Melia azedarach. Phytochemistry 49, 1773–1776.
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Salannai, meliacarpinin E, salannin, nimbolinin B, nimbolidin B |
Ruo Chun et al., 1996Ruo Chun, H., Tadera, K., Yagi, F., Minami, Y., Okamura, H., Iwagawa, T., Nakatani, M., 1996. Limonoids from Melia azedarach. Phytochemistry 43, 581–583.
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Azadarachin C |
Huang et al., 1995Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., Nakatani, N., 1995. Azedarachin C, a limonoid antifeedant from Melia azedarach. Phytochemistry 38, 593–594.
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|
|
Azadirachtin type limonoids: 1-tigloyl-3,20-diacetyl-11-methoxy meliacarpinin, 3-tigloyl-1,20-diacetyl-11-methoxy meliacarpinin, 1-cinnamoyl-3-hydroxy-11-methoxy melia carpinin, 1-deoxy-3-methacrylyl-11-methoxy meliacarpinin, 1-cinnamoyl-3-acetyl-11-methoxy melia carpinin |
Takeya et al., 1996Takeya, K., Qiao, Z., Hirobe, C., Itokawa, H., 1996. Cytotoxic azadirachtin-type limonoids from Melia azedarach. Phytochemistry 42, 709–712.
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|
Azadirachtin type limonoids, 1-tigloyl-3-acetyl-11-methoxymeliacarpinin and 1-acetyl-3-tigloyl-11-methoxy meliacarpinin, sendanin type limonoids, 29-iso butyl sendanin, 12-hydroxy amoorastin, 29-deacetyl sendanin |
Itokawa et al., 1995Itokawa, H., Qiao, Z.S., Hirobe, C., Takeya, K., 1995. Cytotoxic limonoids and tetra-nortriterpenoids from Melia azedarach. Chem. Pharm. Bull. 43, 1171–1175.
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|
Trichilin H, 12-acetyltrichilin B, 7,12 diacetyl trichilin B, trichilin B and D, meliatoxin A2 |
Nakatani et al., 1994Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., Iwagawa, T., 1994. Limonoidantifeedants from Chinese Melia azedarach. Phytochemistry 36, 39–41.
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|
Fruit |
Meliarttenin |
Carpinella et al., 2002Carpinella, C., Ferrayoli, C., Valladares, G., Defago, M., Palacios, S., 2002. Potentlimonoid insect antifeedant from Melia azedarach. Biosci. Biotechnol. Biochem. 66, 1731–1736.
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|
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Limonoids and one tirucallane-triterpenoid |
Akihisa et al., 2013Akihisa, T., Pan, X., Nakamura, Y., Kikuchi, T., Takahashi, N., Matsumoto, M., Ogihara,E., Fukatsu, M., Koike, K., Tokuda, H., 2013. Limonoids from the fruits of Melia azedarach and their cytotoxic activities. Phytochemistry 89, 59–70.
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|
Ripe fruits |
C-Seco limonoids and new tetracyclic limonoids |
Zhou et al., 2005Zhou, H., Hamazaki, A., Fontana, J.D., Takahashi, H., Wandscheer, C.B., Fukuyama, Y., 2005. Cytotoxic limonoids from Brazilian Melia azedarach. Biol. Pharm. Bull. 28, 1362–1365.
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|
|
New ring C-seco limonoids |
Zhou et al., 2004Zhou, H., Hamazaki, A., Fontana, J.D., Takahashi, H., Esumi, T., Wandscheer, C.B., Tsujimoto, H., Fukuyama, Y., 2004. New ring C-seco limonoids from Brazilian Melia azedarach and their cytotoxic activity. J. Nat. Prod. 67, 1544–1547.
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Melia dubia
|
Bark |
Meliastatins 1-5 |
Pettit et al., 2002Pettit, G.R., Numata, A., Iwamoto, C., Morito, H., Yamada, T., Goswami, A., Clewlow, P.J., Cragg, G.M., Schmidt, J.M., 2002. Antineoplastic agents. 489. Isolation and structures of meliastatins 1–5 and related euphane triterpenes from the tree Melia dubia. J. Nat. Prod. 65, 1886–1891.
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|
Roots |
Tetranortriterpenoids |
Puroshothaman et al., 1984Puroshothaman, K.K., Duraiswamy, K., Connolly, J.D., 1984. Tetranortriterpenoids from Melia dubia. Phytochemistry 23, 135–137.
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Melia composita
|
Roots |
Anthroquinones and glycosyl derivative of ellagic acid |
Srivastava and Srivastava, 1996Srivastava, S.D., Srivastava, S.K., 1996. New constituents of Melia composita. Fitoterapia 67, 113–116.
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Melia toosendan
|
Stem bark |
Trichilins K and L, along with five known limonoids, trichilins H, I and J, azedarachin A and 12-O-acetyl-azedarachin B. |
Zhou et al., 1996Zhou, J.B., Okamura, H., Iwagawa, T., Nakatan, M., 1996. Limonoid Antifeedants from Melia toosendan. Phytochemistry 41, 117–120.
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|
Root bark |
Ring C-seco limonoids, 3-O-acetylohchinolal, ohchinolide C and nimbolidin F, salannin, azadirone and acetyl trichilenone |
Zhou et al., 1997Zhou, J., Minami, Y., Yagi, F., Tadera, K., Nakatani, M., 1997. Ring C-seco limonoids from Melia toosendan. Phytochemistry 46, 911–914.
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|
|
Limonoids with a C-19/C-29 bridged acetyl trichilin H 29-O-substituted amoorastatone derivatives neoazedarachins A, B and D |
Zhou et al., 1998Zhou, J.B., Tadera, K., Minami, Y., Yagi, F., Kukawaki, J., Takezaki, K., Nakatani, M.,1998. New limonoids from Melia toosendan. Biosci. Biotechnol. Biochem. 62, 496–500.
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|
|
Limonoids spirosendan, trichilinin D-E, and 1-deacetylnimbolinin A, nimbolinin B and its 1-deacetyl derivative |
Nakatani et al., 1999Nakatani, M., Shimokoro, M., Zhou, J.B., Okamura, H., Iwagawa, T., Tadera, K., Nakayama, N., Naoki, H., 1999. Limonoids from Melia toosendan. Phytochemistry 52, 709–714.
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|
Fruits |
Toosendanal and 12-O-methylvolkensin, meliatoxin B, trichilin H and toosendanin |
Tada et al., 1999Tada, K., Takido, M., Kitanaka, S., 1999. Limonoids from fruit of Melia toosendan and their cytotoxic activity. Phytochemistry 51, 787–791.
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12-O-methyl-1-O-deacetylnimbolinin B, 12-O-methy-1-O-tigloyl-1-O-deacetylnimbolinin B, 12-O-ethylnimbolinin B, and 1-O-cinnamoyl-1-O-debenzoylohchinal and tirucallane-type triterpenoids, meliasenins S and T |
Hu et al., 2011Hu, J.F., Fan, H., Wang, L.J., Wu, S.B., Zhao, Y., 2011. Limonoids from the fruits of Melia toosendan. Phytochem. Lett. 4, 292–297.
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Meliatoosenins E-S |
Zhang et al., 2012bZhang, Y., Tang, C.P., Ke, C.Q., Li, X.Q., Xie, H., Ye, Y., 2012b. Limonoids from the fruits of Melia toosendan. Phytochemistry 73, 106–113.
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Nimbolinin-type limonoids, 12a/b-1-O-tigloyl-1-O-deacetyl-nimbolinin B, 1-deacetylnimbolininB, nimbolinin B and nimbolinin A |
Su et al., 2013Su, S., Shen, L., Zhang, Y., Liu, J., Cai, J., Hao, L., Feng, Y., Yang, S., 2013. Characterizationof tautomeric limonoids from the fruits of Melia toosendan. Phytochem. Lett. 6, 418–424.
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|
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Limonoids |
Zhang et al., 2013bZhang, Q., Li, J.K., Ge, R., Liang, J.Y., Li, Q.S., Min, Z.D., 2013b. Novel NGF-potentiating limonoids from the fruits of Melia toosendan. Fitoterapia 90, 192–198.
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Melia volkensi
|
Root bark |
Apotirucallane triterpenes meliavolkensins A and B, toosendanin and meliavolen, melianinone, 3-episapelin A, nimbolin B |
Zeng et al., 1995aZeng, L., Gu, Z., Chang, C.J., Smith, D.L., McLaughlin, J.L., 1995a. A pair of new apotirucallane triterpenes, meliavolkensins A and B, from Melia volkensii (Meliaceae). Bioorg. Med. Chem. Lett. 5, 181–184.
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Meliavolin, apotirucallane triterpene, and meliavolkin, tetranortriterpene, together with melianin A, |
Zeng et al., 1995bZeng, L., Gu, Z.M., Chang, C.J., Wood, K.V., Mc Laughin, J.L., 1995b. Meliavolkenin, a new bioactive triterpenoid from Melia volkensii (Meliaceae). Bioorg. Med. Chem. Lett. 3, 383–390.
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Ring C-seco limonoids, nimbolidins C-E along with known Seco-limonoids, nimbolidin B and salannin |
Nakatani et al., 1996Nakatani, M., Zhou, J.B., Nakayama, N., Okamura, H., Iwagawa, T., 1996. Nimbolidins C-E, limonoid antifeedants from Melia toosendan. Phytochemistry 41, 733–739.
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Volkensinin (C32H42O11) |
Rogers et al., 1998Rogers, L.L., Zeng, L., Mc Laughlin, J.L., 1998. Volkensinin – a new limonoid from Melia volkensii. Tetrahedron Lett. 39, 4623–4626.
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Seeds |
Antimyco bacterial triterpenes, 12β-hydroxykulactone(1)6β-hydroxykulactone (2) |
Cantrell et al., 1999Cantrell, C.L., Rajab, M.S., Franzblau, S.G., Fisher, N.H., 1999. Antimycobacterial triterpenes from Melia volkensii. J. Nat. Prod. 62, 546–548.
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Melicope semecarpifolia
|
Leaves |
Furoquinoline alkaloids and cytotoxic constituents. Meliacarpine, semecarpine and (+/−)-8-methoxyplatydesmine, together with flavone ayanin |
Chen et al., 2003Chen, J.J., Duh, C.Y., Huang, H.Y., Chen, I.S., 2003. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia. Planta Med. 69, 542–546.
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Munronia delavayi
|
Whole plants |
Limonoids, mulavanins A-E, along with four known compounds 2α,3α,15β-trihydroxy-20(S)-tigloyl-pregnane, mombasol, 14,15β-epoxyprieurianin and nymania 3 |
Lin et al., 2010Lin, B.D., Chen, H.D., Liu, J., Zhang, S., Wu, Y., Dong, L., Yue, J.M., 2010. Mulavanins A-E: limonoids from Munronia delavayi. Phytochemistry 71, 1596–1601.
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Munronia henryi
|
Whole plant |
A,B-seco-tetranortriterpenoid lactam, munroniamide |
Qi et al., 2003Qi, S.H., Wu, D.G., Chen, L., Ma, Y.B., Luo, X.D., 2003. Insect antifeedants from Munronia henryi: structure of munroniamide. J. Agric. Food Chem. 51, 6949–6952.
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Limonoids munronolide, munronolide 21-O-β-d-glucopyranoside |
Zhang et al., 2004Zhang, H.P., Bao, G.H., Wang, H.B., Qin, G.W., 2004. Two new limonoids from Munronia henryi. Nat. Prod. Res. 18, 415–419.
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Munronia unifoliolata
|
Whole plant |
Limonoids, named munronoids A-J |
Ge et al., 2012Ge, Y.H., Zhang, J.X., Mu, S.Z., Chen, Y., Yang, F.M., Lu, Y., Hao, X.J., 2012. Munronoids A-J, ten new limonoids from Munronia unifoliolata Oliv. Tetrahedron 68, 566–572.
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Neobeguea leandreana
|
Stem bark |
Phragmalin limonoids leandreanins A, B and C |
Coombes et al., 2003Coombes, P.H., Mulholland, D.A., Randrianarivelojosia, M., 2003. Phragmalin limonoids from the Madagascan Meliaceae Neobeguea leandreana. J. Nat. Prod.66, 735–738.
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Neobegueae mahafalensis
|
Bark |
Limonoid, neobeguin, and β-amyrin and stigmasterol |
Randrianarivelojosia et al., 1999Randrianarivelojosia, M., Kotsos, M.P., Mulholland, D.A., 1999. A limonoid from Neobeguea mahafalensis. Phytochemistry 52, 1141–1143.
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|
Seed shells |
Three triterpenoids, sapelin C, sapelin E acetate and grandifoliolenone |
Naidoo et al., 2003Naidoo, D., Mulholland, D.A., Randrianarivelojosia, M., Coombes, P.H., 2003. Limonoids and triterpenoids from the seed of Neobeguea mahafalensis. Biochem.Syst. Ecol. 31, 1047–1050.
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|
Seed |
Methyl angolensate, mexicanolide and khayasin |
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Owenia cepiodora
|
Leaves and bark |
Limonoid, 28-deoxonimbolide, and three protolimonoids, 24S,25-dihydroxytirucall-7-en-3-one, 3-oxo-tirucalla-7, 24-dien-21-al and 21,24R-epoxy-25-hydroxytirucall-7-en-3-one |
Mulholland et al., 1998cMulholland, D.A., Kotsos, M., Mahomed, H.A., Taylor, D.A.H., 1998c. Triterpenoids from Owenia cepiodora. Phytochemistry 49, 2457–2460.
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Quivisia papinae
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Seeds |
Limonoid quivisianthone, and 6a-hydroxyazadiradione and 7-deacetyl-7-angeloyl-6ahydroxyazadiradione, azadiradione |
Coombes et al., 2004Coombes, P.H., Mulholland, D.A., Randrianarivelojosia, M., 2004. Quivisianthone, ane vodulone limonoid from the Madagascan Meliaceae Quivisia papinae. Phytochemistry 65, 377–380.. |
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Mexacanolide limonoids, quivisianolideA, quivisianolideB and quivisianone |
Coombes et al., 2005Coombes, P.H., Mulholland, D.A., Randrianarivelojosia, M., 2005. Mexicanolidelimonoids from the Madagascan Meliaceae Quivisia papinae. Phytochemistry 66,1100–1107.. |
Sandoricum indicum
|
Stem bark |
Multiflorane-triterpenoid acids 12β-hydroxy multiflorane triterpenoid acids, sandorinic acids A-C |
Tanaka et al., 2001Tanaka, T., Koyano, T., Kowithayakorn, T., Fujimoto, H., Okuyama, E., Hayashi, M.,Komiyama, K., Ishibashi, M., 2001. New multiflorane-type triterpenoid acids from Sandoricum indicum. J. Nat. Prod. 64, 1243–1245.
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Sandoricum koetjape
|
Leaves |
Trijugin type limonoids, sandrapins A, B and C |
Ismail et al., 2003Ismail, I.S., Ito, H., Hatano, T., Taniguchi, S., Yoshida, T., 2003. Modified limonoids from the leaves of Sandoricum koetjape. Phytochemistry 64, 1345–1349.
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Analogues of trijugin type limonoids sandrapins D and E |
Ismail et al., 2004Ismail, I.S., Ito, H., Hatano, T., Taniguchi, S., Yoshida, T., 2004. Two new analogues of trijugin-type limonoids from the leaves of Sandoricum koetjape. Chem. Pharm. Bull. 52, 1145–1147.
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Andirobin-type limonoids, named sandoripin A and sandoripin B |
Pancharoen et al., 2009Pancharoen, O., Pipatanapatikarn, A., Taylor, W.C., Bansiddhi, J., 2009. Two new limonoids from the leaves of Sandoricum koetjape. Nat. Prod. Res. 23, 10–16.
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|
Stem bark |
Secomultiflorane type triterpenoid acids, bryonic acid and two new ring-A seco triterpenoids |
Kosela et al., 1995Kosela, S., Yulizar, Y., Tori, M., Asakawa, Y., 1995. Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum koetjape. Phytochemistry 38, 691–694.
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Soymida febrifuga
|
Root callus |
Methyl angolensate and luteolin-7-O-glucoside |
Chiruvella et al., 2007Chiruvella, K.K., Mohammed, A., Dampuri, G., Ghanta, R.G., Raghavan, S.C., 2007. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. IJBS 3, 269–278.
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|
Bark |
Phragmalin type limonoids soymidin A and B. |
Ashok Yadav et al., 2012Ashok Yadav, P., Suresh, G., Prasad, K.R., Rao, M.S.A., Babu, K.S., 2012. Newphragmalin-type limonoids from Soymida febrifuga. Tetrahedron Lett. 53,773–777.
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Swietenia macrophylla
|
Leaves |
Phragmalin ortho esters, named swietephragmin H-J, and polyhydroxylated phragmalin, swietemacrophine |
Tan et al., 2009Tan, S.K., Osman, H., Wong, K.C., Boey, P.L., 2009. New phragmalin-type limonoids from Swietenia macrophylla King. Food Chem. 115, 1279–1285.Tan et al., 2009
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|
Fruits |
Phragmalin-type limonoid, 6-O-acetyl-3′-demethylswietephragmin E |
Chen et al., 2010Chen, J.J., Huang, S.S., Liao, C.H., Wei, D.C., Sung, P.J., Wang, T.C., Cheng, M.J., 2010. A new phragmalin-type limonoid and anti-inflammatory constituents from thefruits of Swietenia macrophylla. Food Chem. 120, 379–384.
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|
Seeds |
Tetranortriterpenoids |
Kojima et al., 1998 |
|
|
Limonoids; augustineolide, 3β-6 dihydroxy dihydrocarpin from S. macrophylla and 6-acetoxy humilinolide from aubrevillena |
Mootoo et al., 1999Mootoo, B.S., Ali, A., Motilal, R., Pingal, R., Ramlal, A., Khan, A., Reynolds, W.F., McLean, S., 1999. Limonoids from Swietenia macrophylla and S. aubrevilleana. J. Nat. Prod. 62, 1514–1517.
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Swietenia mahagoni
|
Leaves |
Scopoletin, melianone, cyclo mehogenol, swietenin, stigmasterol glucose |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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|
|
Phragmalin limonoids swietephragmins A-G, and two other different types of 2-hydroxy-3-O-tigloylswietenolide and deacetylsecomahoganin, methyl 6-hydroxyangolensate, swietemahonin G and 7-deacetoxy-7-oxogedunin |
Abdelgaleil et al., 2006Abdelgaleil, S.A.M., Doe, M., Morimoto, Y., Nakatani, M., 2006. Rings B,D-secolimonoids from the leaves of Swietenia mahogani. Phytochemistry 67, 452–458.
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|
|
Phragmalin-type limonoids, swietephragmin H, swietephragmin I and 11-hydroxyswietephragmin B, and a mexicanolide-type limonoid 2-hydroxy-6-deacetoxyswietenine 6-O-acetyl-2-hydroxyswietenin, 2-hydroxyswietenine, swietemahonin G, methyl 6-hydroxyangolensate and 7-deacetoxy-7-oxogedunin |
Abdelgaleil et al., 2013Abdelgaleil, S.A.M., Doe, M., Nakatani, M., 2013. Rings B,D-seco limonoidantifeedants from Swietenia mahogani. Phytochemistry 96, 312–317.
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|
Twigs and leaves |
Limonoids, swiemahogins A and B |
Chen et al., 2007Chen, Y.Y., Wang, X.N., Fan, C.Q., Yin, S., Yue, J.M., 2007. Swiemahogins A and B, two novel limonoids from Swietenia mahogani. Tetrahedron Lett. 48, 7480–7484.
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|
Stem bark |
Phragmalin 8,9,14-orthoacetate with the addition of methyl 2,30-orthoacetate or a propionate, swietenialides A, B, and C and two ring-D opened phragmalin-type 1,8,9-orthoacetates, swietenialides D and E, mexicanolide, 2-hydroxyswietenin |
Saad et al., 2003Saad, M.M.G., Iwagawa, T., Doe, M., Nakatani, M., 2003. Swietenialides, novel ring Dopened phragmalin limonoid orthoesters from Swietenia mahogani Jacq. Tetrahedron 59, 8027–8033.
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|
Heart wood |
Cyclo swietenol, lupleol, benzoate hedergenin, cycloartenol, β-sitosterol |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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|
Seeds |
6-Desoxyswietenine |
Govindachari et al., 1999aGovindachari, T.R., Banumathy, B., Gopalakrishnan, G., Suresh, G., 1999a. 6-Desoxyswietenine, a tetranortriterpenoids from Swietenia mahogani. Fitoterapia70, 106–108.
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Toona ciliata
|
Leaves |
Limonoids, toonayunnanins A-L |
Liu et al., 2012Liu, J.Q., Wang, C.F., Li, Y., Chen, J.C., Zhou, L., Qiu, M.H., 2012. Limonoids from the leaves of Toona ciliata var. yunnanensis. Phytochemistry 76, 141–149.
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|
Leaves and stems |
Siderin, 4,6,7-trimethoxy-5-methylcoumarin, isoscopoletin, scopoletin, 6,7-dimethoxycoumarin, 7-hydroxy-6,8-dime-thoxycoumarin, dehydrodiconiferyl alcohol, (−)-lariciresinol, thero-2,3-bis-(4-hydroxy-3-methoxypheyl)-3-methoxy-propa-nol, cycloeucalenol, 8(14), 15-isopimaradiene-2,3,19-triol, 3S,5R-dihydroxy-6R, 7-megstigmadien-9-one, (−)-loliolide, (+)-catechin, dimethyl malate, diisobutyl phthalate, dibutyl phthalate, 1,3,5-trimethoxybenzene, syringic acid, syringaldehyde, vanillic acid, vanillin, and 3,3′,5,5′-tetra-tert-butyl-2,2′-dihydroxybiphenyl |
Liu et al., 2011aLiu, Y.B., Cheng, X.R., Qin, J.J., Yan, S.K., Jin, H.Z., Zhang, W.D., 2011a. Chemical constituents of Toona ciliata var. pubescens. Chin. J. Nat. Med. 9, 115–119.
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|
Stem |
Toonacilianins A-J, and two norlimonoids, toonacilianins K and L |
Liu et al., 2011bLiu, J.Q., Yang, S.P., Su, Z.S., Lin, B.D., Wu, Y., Yue, J.M., 2011b. Limonoids from the stems of Toona ciliata var. henryi (Meliaceae). Phytochemistry 72, 2189–2196.
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|
Stem bark |
Five new pregnane steroids, toonasterones A, B, (Z)-aglawone, (Z)-toonasterone C, and (E)-toonasterone C |
Wang et al., 2011Wang, J.R., Shen, Q., Fang, L., Peng, S.Y., Yang, Y.M., Li, J., Liu, H.L., Guo, Y.W., 2011. Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var. pubescens. Steroids 76, 571–576.
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Toona microcarpa
|
Stem and bark |
A flavanone, (+)-catechin, two lignans, (6R,7S,8S)-7a-[(β-d-glucopyranosyl)oxy]lyoniresinol and (6R,7R,8R)-7a-[(β-d-glucopryanosyl) oxy]lyoniresinol and a steroid 20-hydroxyecdysone |
Fang et al., 2010Fang, X., Di, Y.T., He, H.P., Hua, G.W., Li, S.L., Hao, X.J., 2010. Chemical constituentsof Toona microcarpa (C. DC.) Harms in Engl. (Meliaceae). Biochem. Syst. Ecol. 38,128–130.
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Trichilia americana
|
Stem |
Steroid 2-hydroxyandrost-1,4-dien-3,16-dione (trichiliasterone B) |
Hantos et al., 2001Hantos, S.M., Tripathy, S., Alibhai, N., Durst, T., 2001. Synthesis of trichiliasterones Aand B-16-ketosteroids isolated from Trichilia hirta and Trichilia americana. Can.J. Chem. 79, 1747–1753.
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Trichilia casaretti
|
Leaves |
β-sitosterol, stigmasterol |
Figueiredo, 2010Figueiredo, E.R., (Thesis) 2010. Estudo Fitoquímico de Trichilia casarettii e Trichilia silvatica. State University of North Fluminense, Campos dos Goytacazes.
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Trichilia catigua
|
Bark |
Gamma lactones and its precursors omega-phenylalkanes, three omega phenyl alkanoic acids. Five omega-phenyl-gamma lactones, two alkyl-gammalactones, one alkenyl-gamma lactone and mixture of fatty acids ranging from C-14 to C-26 |
Pizzolatti et al., 2004Pizzolatti, M.G., Verdi, L.G., Brighente, I.M., Madurreira, L.A.D.S., Filho, R.B., 2004. Two epimeric flavalignans from Trichilia catigua (Meliaceae) with antimicrobialactivity. Nat. Prod. Res. 18, 433–438.
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|
Whole plant |
7-Hydroxy-1-oxo-14-norcalamenene, 7,14-dihydroxy calamenene, sitosteryl-β-Δ-glucopyranoside |
Garcez et al., 1997aGarcez, F.R., Garcez, W.S., Tsutsumi, M.T., Roque, N.F., 1997a. Limonoids from Trichilia elegans ssp. elegans. Phytochemistry 45, 141–148.
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|
Fruits |
Meliacin-type limonoids fotogedunin A, B |
Matos et al., 2009Matos, A.P., Nebo, L., Vieira, P.C., Fernandes, J.B., Silva, M.F.G.F., 2009. Constituintes químicos e atividade inseticida dos extratos de frutos de Trichilia elegans e T. catigua(Meliaceae). Quim. Nova 32, 1553–1556.
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|
Seeds |
Methyl angolensate, 11β-methoxycedrelone |
Matos et al., 2007Matos, A.P., Nebo, L., Vieira, P.C., Souza, P.R., Fernandes, J.B., Silva, M.F.G.F., Rodrigues, R.R., 2007. Atividade biológica dos extratos de fungos e sementes de Trichilia spp. sobre Spodoptera frugiperda: limonóides de T. catigua. In: 30th Annual Conven-tion of Brazilian Society of Chemistry, Águas de Lindóia City, São Paulo State, 31June to 3 July (CD Data).
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Trichilia claussenii
|
Leaves |
24-Methylene-26-hydroxycycloartan-3-one, 24-methylene cycloartanol fatty acids derivatives, caryophyllene epoxide, a mixture of Ω-phenyl alkanoic and alkenoic acids, plastocromenol,α-tocopherol, squalene and a mixture of sitosterol and stigmasterol |
Pupo et al., 1996Pupo, M.T., Vieira, P.C., Fernandes, J.B., Silva, M.F.G.F., 1996. A cycloartane triterpenoid and ω-phenyl alkanoic and alkenoic acids Trichilia claussenii. Phytochemistry 42, 795–798.
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|
|
3-O-β-glycopyranoside sitosterol, 3-O-β-glycopyranoside stigmasterol |
Pupo et al., 1997Pupo, M.T., Vieira, P.C., Fernandes, B., Fatima Das, M., Da Silva, G.F., Rodrigues,E., 1997. Androstane e pregnane 2-beta, 19-hemiketal steroids from Trichilia claussenii. Phytochemistry 45, 1495–1500.
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|
|
β-Sitosterol etherified, stigmasterol etherified |
Pupo et al., 2002Pupo, M.T., Adorno, M.A.T., Vieira, P.C., Fernandes, J.B., Silva, M.F.G., Pirani, J.R., 2002. Terpenoids and steroids from Trichilia species. J. Braz. Chem. Soc. 13, 382–388.
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|
Fruits |
γ-Lactones (2R,3S,4S)-3-hydroxy-4-methyl-2-(13′-phenyl-1′-n-tride cyl)-butanolide. (2R,3S,4S)-3-hydroxy-4-methyl-2-(11′-phenyl-1′-n-undecyl)-butanolide. (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′n-hexa dec-7′(z)-enyl)-butanolide and (2R,3S,4S)-3-hydroxy-4methyl-2-(1′-n-tetra decyl)-butanolide |
Pupo et al., 1998Pupo, M.T., Vieira, P.C., Fernandes, J.B., Fatima Das, M., Da Silva, G.F., 1998. γ-Lactones from Trichilia claussenii. Phytochemistry 48, 307–310.
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|
Wood |
2α,3α-dihydroxyandrostan-16-one-2β,19-hemiketal,2α,3β-dihydroxypregnan-16-one-2β,19-hemiketal,2β,3β,4β-trihydroxypregnan-16-one,2α,3α,4β-trihydroxypregnan-16-one, 2β,3β-dihydroxypregnan-16-one |
Pupo et al., 1997Pupo, M.T., Vieira, P.C., Fernandes, B., Fatima Das, M., Da Silva, G.F., Rodrigues,E., 1997. Androstane e pregnane 2-beta, 19-hemiketal steroids from Trichilia claussenii. Phytochemistry 45, 1495–1500.
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Trichilia connaroides
|
Leaves |
Heynic acid and 24-methylene cycloartane-3β, 21-diol |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
|
|
Leaves |
Methyl 11′,13′-dioxo-12′-aza-[4,4,3]-pro, 4a,8a-(methaniminomethano)naphthalene-9,11, naphthalene, bicyclo[3.1.1],2,6,6-trimethyl heptan-3-one, isotridecanol, 7-tetradecene, octane, 1-bromo-2-chloro-1,1-difluro-2-tridecan (hexacosane), tetrahydroxy myrcenol, dodecyl acrylate (oleic acid), 1-(1,5-dimethyl)-4-hexyl-4-methyl benzene, 17-pentatriacontane, 2,4-bis(1,1-dimethylethyl) phenol, silane-trichlorodocosyl, -undecanethiol,2-methyl, pentadecane, undecane, decane, hydroxylamine, o-decyl, dodecanoic acid, 2-hexyl-1-octanol, germacrane-B, erucic acid, phthalic acid, cyclobetyl octyl ester, nonadecane, hexadecanoic acid methyl ester (palmitic acid), serverogenin acetate, dotriacontane, isochiapin B, phytol, oleic acid, ethyl linoleate, ethyl oleate, 2-(3-innoxyl)3-5-aminopyridol (2,3-dipyrimidine), 4,4′,6,6′-tetra-butyl O,O′-biphenol, eicosane, phthalic acid octyl tridec-2-yn-1-yl ester, 6,10,14,18,22-tetra cosa pentane 2-ol, 3-bromo,2,6,10,15, lycopersen, solanesol |
Senthilkumar et al., 2012Senthilkumar, N., Murugesan, S., Vijayalakshmi, K.B., 2012. GC–MS–MS analysis of Trichilia connaroides (Wight & Arn.) Bentv (Meliaceae): a tree of ethnobotanical records. Asian J. Plant Sci. Res. 2, 207–211.
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|
Twigs and leaves |
Trijugins D-H and methyl 8a-hydroxy-8,30-dihydroangolensate, two degraded limonoids, trichiconnarins A and B, and a pregnane steroid, 3b,4a-dihydroxypregnan-21-one, along with the known trijugin C and 3b,4a-dihydroxypregnan-16-one |
Wang et al., 2008Wang, X.N., Fan, C.Q., Yin, S., Gan, L.S., Yue, J.M., 2008. Structural elucidation of limonoids and steroids from Trichilia connaroides. Phytochemistry 69, 1319–1327.
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|
Pericarp |
Mexicanolide type limonoid, 2-hydroxy-3-O-tigloyl-6-O-acetyl swietenolide and tirucallane type triterpenoid derivative, lipo-3-epi sapelin A |
Inada et al., 1994Inada, A., Konishi, M., Murata, H., Nakanishi, T., 1994. Structures of a new limonoid and a new triterpenoid derivative from pericarps of Trichilia connaroides. J. Nat. Prod. 57, 1446–1449.
|
Trichilia cuneata
|
Stem and leaves |
13-acetoxy-14-nordehydrocacalohastine, maturinone |
Doe et al., 2005Doe, M., Shibue, T., Haraguchi, H., Morimoto, Y., 2005. Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata. Org. Lett. 7, 1765–1768.
|
Trichilia dregeana
|
Stem |
Limonoids with furan-ringdregeana-5, dregeanin, 12-(2′-deacetyl)-dregeanin |
Connolly et al., 1976Connolly, J.D., Okorie, D.A., De Wit, L.D., Taylor, D.A.H., 1976. Structure of dregeaninand rohitukin, limonoids from the subfamily Melioideae of the family Meliaceae. An unusual high absorption frequency for a six-membered lactone ring. J. Chem. Soc. Chem. Commun. 22, 909–910.
|
|
Seeds |
Limonoids with furan-ring, dregeana 1-4, hispidin C |
Mulholland and Taylor, 1980Mulholland, D.A., Taylor, D.A.H., 1980. Limonoids from the seed of the natal Mahogany, Trichilia dregeana. Phytochemistry 19, 2421–2425.
|
Trichilia elegans
|
Seed and bark |
seco-A ring protolimonoids |
Garcez et al., 1996Garcez, F.R., Garcez, W.S., Rodrigues, E.D., Roque, N.F., 1996. Seco-protolimonoids from Trichilia elegans ssp. elegans. Phytochemistry 42, 1399–1403.
|
|
Seeds |
Limonoids seco-A, B and D carbocyclic rings, kihadanin A and B, 3-O-β-d-glucopyranosyl-sitosterol |
Garcez et al., 1997bGarcez, W.S., Garcez, F.R., Ramos, L., Camargo, M.J., Damasceno Jr., G.A., 1997b. Sesquiterpenes from Trichilia catigua. Fitoterapia 68, 87–88.
|
|
Seeds |
7-Deoxo-7β-acetoxykihadanin A, B, 7-deoxo-7β-hidroxykihadanin A, B, 7-deoxo-7α-hidroxykihadanin A, 7-deoxo-7α-acetoxykihadanin A, B |
Garcez et al., 2000Garcez, F.R., Garcez, W.S., Roque, N.F., Castellano, E.E., Zukerman-Schpector, J., 2000. β-Oxygenated limonoids from Trichilia elegans ssp. Elegans. Phytochemistry 55,733–740.
|
Trichilia emetica
|
Stem bark |
Nymanial, drageane 4, trichilin A, rohituka 3, trichilin B and a protolimonoid |
Gunatilaka et al., 1998Luo, X.D., Wu, S.H., Wu, D.G., Ma, Y.B., Qi, S.H., 2002. Three new apotirucallols with six-membered hemiacetal from Meliaceae. Tetrahedron 58, 6691–6695.
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|
Roots |
Four pregnanes: 1-methoxy-pregnan-17(R)-1,4-dien-3,16-dione, 1-methoxy-pregnan-17(S)-1,4-dien-3,16-dione, 2,3-seco-pregnan-17(S)-2,3-dioic acid-16-oxo-dimethyl ester, 2α,3α,16α-trihydroxy-5α-pregnan-17(R)-20-yl acetate, three androstanes: 1-methoxy-androstan-1,4-dien-3,16-dione,2,3-seco-androstan-2,3-dioic acid-16-oxo-dimethyl ester, 3-methoxycarbonyl-2,3-seco-androstan-3-oic acid-16-oxo-2,19-lactone, pregnane derivatives 2α,3α,16α,20-tetrahydroxy-5α-pregnane, 2β,3β-dihydroxypregnan-16-one, 2β,3α-dihydroxypregnan-16-one |
Malafronte et al., 2013Malafronte, N., Sanogo, R., Vassallo, A., Tommasi, N.D., Bifulco, G., Piaz, F.D., 2013. Androstanes and pregnanes from Trichilia emetica ssp. suberosa J.J. de Wilde. Phytochemistry 96, 437–442.
|
Trichilia estipulate
|
Leaves |
7-oxo-24α-sitosterol, β-sitosterol, sitosterone |
Cortez et al., 1998aCortez, D.A.G., Fernandes, J.B., Vieira, P.C., Da Silva, M.F.G.F., Ferreira, G.A., Cass, Q.Z.B., Pirani, J.R., 1998a. Meliacin butenolides from Trichilia estipulata. Phytochemistry 49, 2493–2496.
|
|
Bark |
Lignan glycosides. (−)-isolariciresinol-3α-O-β-d-xylopuranoside, (−)-lyoniresinol-3α-O-β-d-xylopyranoside and the new lignans (+)-4′-O-methyl-9′-deoxy isolari ciresinol-3α-O-β-d-glucopyranosi de, (−)-lyoniresinol-3α-l-rhamnopyranoside |
Cortez et al., 1998bCortez, D.A.G., Fernandes, J.B., Vieira, P.C., Cass, Q.Z.B., Da Silva, M.F.G.F., Ferreira, G.A., Pirani, J.R., 1998b. Lignan glycosides from Trichilia estipulata bark. Nat. Prod. Lett. 11, 255–262.
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|
|
Meliacin butenolides, 7a-23-dihydroxy-3-oxo-24,25,26,27-tetranorapotirucall-1,14,20(22)-trien-21,23-olide, 7-deacetyl-23-hydroxyneotrichilenonelide and 7-deacetyl-21-hydroxyneotrichilenonelide, together with scopoletin, isofraxidin, 7-oxo-24β-, 7-oxo-24α-sitosterols and 3β-O-β-d-glucopyranosylsitosterol |
Cortez et al., 1998aCortez, D.A.G., Fernandes, J.B., Vieira, P.C., Da Silva, M.F.G.F., Ferreira, G.A., Cass, Q.Z.B., Pirani, J.R., 1998a. Meliacin butenolides from Trichilia estipulata. Phytochemistry 49, 2493–2496.
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|
|
Limonoid 21,24,25,26,27-pentanor-15,22-oxo-7a,23-dihydroxy-apotirucalla(eupha)-1-en-3-one |
Cortez et al., 2000Cortez, D.A.G., Fernandes, J.B., Vieira, P.C., Da Silva, M.F.G.F., Ferreira, G.A., 2000. A limonoid from Thichilia estipulata. Phytochemistry 55, 711–713.
|
|
Stem bark |
21,24,25,26,27-pentanor-15,22-oxo-7α,23-dihydroxy-apotirucalla-1-en-3-oen |
Cortez et al., 2000Cortez, D.A.G., Fernandes, J.B., Vieira, P.C., Da Silva, M.F.G.F., Ferreira, G.A., 2000. A limonoid from Thichilia estipulata. Phytochemistry 55, 711–713.
|
Trichilia havanensis
|
Seeds |
Tetranortriterpenoid 1β,2β: 21,23 diepoxy 7α-hydroxy-24,25,26,27 tetranor-apotirucalla-14,20,22-trien-3-one |
Rodriguez et al., 2003Rodriguez, B., Caballero, C., Ortego, F., Castanera, P., 2003. A new tetranortriterpenoid from Trichilia havanensis. J. Nat. Prod. 66, 452–454.
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|
|
Trichavensin |
Rodriguez-Hahn et al., 1996Rodriguez-Hahn, L., Cardenas, J., Arenas, C., 1996. Trichavensin, a prieurianin deriva-tive from Trichilia havanensis. Phytochemistry 43, 457–459.
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|
|
Hydroxybutenolide |
Arenas and Rodrigues-Hahn, 1990Arenas, C., Rodrigues-Hahn, L., 1990. Limonoids from Trichilia havanensis. Phytochemistry 29, 2953–2956.
|
|
Stem |
Limonoid neo-havanensin |
Chan et al., 1967Chan, W.R., Gibbs, J.A., Taylor, D.R., 1967. The Limonoids of Trichilia havanensis Jacq.:an epoxide rearrangement. Chem. Commun. 14, 720–721.
|
|
Stem and fruit |
Limonoid triacetyl-havanensin, trichilenone acetate |
Chan et al., 1967Chan, W.R., Gibbs, J.A., Taylor, D.R., 1967. The Limonoids of Trichilia havanensis Jacq.:an epoxide rearrangement. Chem. Commun. 14, 720–721.
|
|
Fruits |
Carda-14,20(22)-dienolide-1,3,7-tris(acetyloxy)-21-hydroxy-4,4,8-trimethyl-α,3α,5α,7α,13α,17α,21R
|
Arenas and Rodrigues-Hahn, 1990Arenas, C., Rodrigues-Hahn, L., 1990. Limonoids from Trichilia havanensis. Phytochemistry 29, 2953–2956.
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|
|
Limonoid 3,7-diacetyl-havanensin, havanensin |
Chan et al., 1967Chan, W.R., Gibbs, J.A., Taylor, D.R., 1967. The Limonoids of Trichilia havanensis Jacq.:an epoxide rearrangement. Chem. Commun. 14, 720–721.
|
Trichilia hirta
|
Fruits |
Hirtinone, six protolimonoids – nilocitin, dihydronilocitin B, melianone epimers, piscidinol A, melianone lactone, one tertranortriterpenoid, hirtin, and one sesquiterpene, spathulenol |
Vieira et al., 2013Vieira, I.J.C., de Aquino Azevedo, O., de Souza, J.J., Braz-Filho, R., dos Santos Gonçalves, M., de Araújo, M.F., 2013. Hirtinone, a novel cycloartane-type triterpene and other compounds from Trichilia hirta L. (Meliaceae). Molecules 18, 2589–2597.
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|
|
A limonoid methyl-11β-acetoxy-6,23-dihydroxy-12α(2-methylpropionyloxy)-3, 7,21-trioxo-1,5,14,20-meliacatetraen-29-oate |
Cortez et al., 1992Cortez, D.A.G., Fernandes, J.B., Vieira, P.C., Da Silva, M.F.G.F., Ferreira, G.A., 1992. Limonoids from Trichilia hirta. Phytochemistry 31, 625–628.
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|
Seeds and leaves |
Hirtine |
Chan and Taylor, 1966Chan, W.R., Taylor, D.R., 1966. Hirtin and deacetylhirtin: new ‘limonoids’ from Trichilia hirta. Chem. Commun. 7, 206–207.
|
|
Seeds and fruits |
Deacetylhirtine, azadirone |
Chan and Taylor, 1966Chan, W.R., Taylor, D.R., 1966. Hirtin and deacetylhirtin: new ‘limonoids’ from Trichilia hirta. Chem. Commun. 7, 206–207.
|
Trichilia lepidota
|
Leaves |
Terpenes: epoxide caryophyllene, epoxide humulene, spathulenol and steroids: ergost-5,24(28)-dien-3,12-diol-(3β,12β), ergost-5,24(28)-diene-3,12-diol-3-hexadecanoate (3β,12β), 24-methyl-12-β-hydroxycolest-4-en-3-one, 24-methylen-colesterol |
Pupo et al., 2002Pupo, M.T., Adorno, M.A.T., Vieira, P.C., Fernandes, J.B., Silva, M.F.G., Pirani, J.R., 2002. Terpenoids and steroids from Trichilia species. J. Braz. Chem. Soc. 13, 382–388.
|
Trichilia pallida
|
Leaves |
24-methylen-3β,4β,22-trihydroxycolesterol, 24-methylen-3β,22-dihydroxycolesterol, 24-methylen-colesterol |
Cunha et al., 2008Cunha, U.S., Vendramim, J.D., Rocha, W.C., Vieira, P.C., 2008. Bioatividade de moléculas isoladas de Trichilia pallida Swatz (Meliaceae) sobre Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae). Neotrop. Entomol. 37, 709–715.
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|
Roots |
Tetranortriterpnoids 6-hydroxy-11β-acetoxy-12α-(2-methyl propanoyloxy)-3,7-dioxo-14 β,15β-epoxy-1,5-meliacadien-29-oate, methyl 6,11 β-dihydroxy-12α-(2-methyl propanoyloxy)-3,7-dioxo-14β,15β-epoxy-1,5-meliacadien-29-oate and methyl 6-hydroxy-11β-acetoxy-12α-(2-methylbutanoyloxy)-3,7-dioxo-14β,15β-epoxy-1,5-meliacadien-29-oate |
Simmonds et al., 2001Simmonds, M.S.J., Stevenson, P.C., Porter, E.A., Veitch, N.C., 2001. Insect antifeedant activity of three new tetranortriterpenoids from Trichilia pallida. J. Nat. Prod. 64, 1117–1120.
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Trichilia prieuriana
|
Leaves |
Protolimonoid glucoside, prieurianoside, and glycolipid 1,2-dilinolenoyl-3-galactopyranosylglycerol |
Olugbade and Adesanya, 2000Olugbade, T.A., Adesanya, S.A., 2000. Prieurianoside, a protolimonoid glucoside from the leaves of Trichilia prieuriana. Phytochemistry 54, 867–870.
|
|
Stem |
Prieurianin acetate and prieurianin |
Gullo et al., 1975Gullo, V.P., Miura, I., Nakanishi, K., Cameron, A.F., Connolly, J.D., Duncanson, F.D., Harding, A.E., Mccrindle, R., Taylor, D.A.H., 1975. Structure of prieurianin, a complex tetranortriterpenoid; nuclear magnetic resonance analysis at no ambient temperatures and X-ray structure determination. J. Chem. Soc. Chem. Commun. 9, 345–346.
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Trichilia quadrijuga
|
Leaves |
Terpenes: kudtdiol, spathulenol and steroids, β-sitosterol, itesmol, stigmasterol |
Rodrigues et al., 2009Rodrigues, V.F., Carmo, H.M., Oliveira, R.R., Braz-Filho, R., Mathias, L., Vieira, I.J.C.,2009. Isolation of terpenoids from Trichilia quadrijuga (Meliaceae) by droplet counter-current chromatography. Chomatographia 70, 1191–1195.
|
Trichilia rubra
|
Root |
Three minor limonoid components, rubralins A-C |
Musza et al., 1995Musza, L.L., Killar, L.M., Speight, P., Barrow, C.J., Gillum, A.M., Cooper, R., 1995. Minor limonoids from Trichilia rubra. Phytochemistry 39, 621–624.
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|
|
Limonoids rubrin A, B, C, D, E, F and G |
Musza et al., 1994Musza, L.L., Killar, L.M., Speight, P., Mcelhiney, S., Barrow, C.J., Gillum, A.M., Cooper, R., 1994. Potent new cell adhesion inhibitory compounds from the root of Trichilia rubra. Tetrahedron 50, 11369–11378.
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Trichilia rubescens
|
Leaves |
trichirubun A, trichirubun B |
Krief et al., 2004, 2006Krief, S., Martin, M.T., Grellier, P., Kasenene, J., Sévenet, T., 2004. Novel antimalarial compounds isolated in a survey of self-medicative behavior of wild chimpanzees in Uganda. Antimicrob. Agents Chemother. 48, 3196–3199.
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Trichilia silvatica
|
leaves |
(2S,3S,6R,7R)-humulene-2,3,6,7-diepoxide, (2R,3R,6R,7R)-humulene-2,3,6,7-diepoxide, mustacone |
Souza et al., 2009Souza, P.R., Paula, V.F., Correia, S.J., Nascimento, J.C., 2009. Terpenos das folhas de Trichilia silvatica (Meliaceae). In: 32nd Annual Convention of Brazilian Society of Chemistry, Fortaleza City, Ceará State, 30 May to 2 June (CD Data).
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Trichilia welwitschii
|
Seeds |
Limonoids, dregeanin DM4, rohituka 3 and trichilia lactone D5 |
Tsamo et al., 2013Vanucci, C., Lange, C., Lhommet, G., Dupont, B., Davoust, D., Vauchot, B., Clement, J.L., Brunk, F., 1992. An insect antifeedant limonoid from seed of Khaya ivorensis. Phytochemistry 31, 3003–3004.
|
|
Bark |
28,29-dinorcycloart-24-ene-3,4,6-triol (4), sitosterol-3-O-β-d-glucoside, 4-hydroxy-N-methyl- -proline, stigmasterol and sitosterol |
|
Turraea floribunda
|
Seed |
Limonoids and limonoid derivatives, turraflorins D-I, turraflorins A and B |
McFarland et al., 2004McFarland, K., Mulholland, D.A., Fraser, L.A., 2004. Limonoids from Turraea floribunda Meliaceae. Phytochemistry 65, 2031–2037.
|
|
Root bark |
11β-acetoxy-3,7-diacetyl-4α-carbomethoxy-12α-isobutyryloxy-28-nor-1-tigloyl-havanensin |
Torto et al., 1996Torto, B., Hassanali, A., Nyandat, E., Bentley, M.D., 1996. A limonoid from Turraea floribunda. Phytochemistry 42, 1235–1237.
|
|
|
Limonoids of the havanensis class |
Torto et al., 1995Um, B.H., Lobstein, A., Weniger, B., Spiegel, C., Yice, F., Rakotoarison, O., Andriantsitohaina, R., Anton, R., 2003. New coumarins from Cedrelopsis grevei. Fitoterapia 74, 638–642.
|
Turraea holstii
|
Stem and root bark |
Triterpenoids, holstinone A. (21R,23R-epoxy-7α,24S-dihydroxy-21α,25-dimethoxyapotirucalla-1,14-dien-3-one), holstinone B (21S,23R-epoxy-7α,24S,25-trihydroxy-21β-methoxyapotirucalla-1,14-dien-3-one) and holstinone C (21R,23R-epoxy-7α,24S,25-trihydroxy-21α-methoxyapotirucalla-1,14-dien-3-one). |
Mulholland et al., 1999cMulholland, D.A., Kotsos, M., Mahomed, H.A., Taylor, D.A.H., 1998c. Triterpenoids from Owenia cepiodora. Phytochemistry 49, 2457–2460.
|
Turraea parvifolia
|
Root bark |
Vilasinin limonoids, 1α,3α-diacetylvilasinin, 1α-acetyl-3α-propionylvilasinin and 1α,3α-diacetyl-7α-tigloylvilasinin, and two azadirone limonoids mzikonone and 12α-acetoxy-1,2-dihydroazadirone |
Cheplogoi and Mulholland, 2003aCheplogoi, P.K., Mulholland, D.A., 2003a. Limonoids from Turraea parvifolia (Meliaceae). Biochem. Syst. Ecol. 31, 799–803.
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|
Seeds |
Turraparvin A-D, 12α-acetoxyazadironolide, 11-epi-21-hydroxytoonacilide, 11-epi-23-hydroxytoonacilide |
Cheplogoi and Mulholland, 2003bCheplogoi, P.K., Mulholland, D.A., 2003b. Tetranortriterpenoid derivatives from Turraea parvifolia (Meliaceae). Phytochemistry 62, 1173–1178.
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Turraea pubescens
|
Twigs and leaves |
Pregnane steroids, 2β,3β,5β-trihydroxy-pregn-20-en-6-one, 3β-hydroxy-5α-pregn-7,20-dien-6-one, and 3β-acetoxy-5α-pregn-7,20-dien-6-one |
Wang et al., 2006Wang, X.N., Fan, C.Q., Yue, J.M., 2006. New pregnane steroids from Turraea pubescens. Steroids 71, 720–724.
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|
Twigs |
Steroids turranin A-C and one new sesquiterpene turranin F and two new natural products turranin D and E, as well as three known steroids villosterol, 3β-hydroxy-5α-pregn-7,20-dien-6-one, and 2β,3β,5β-trihydroxypregn-20-en-6-one |
Yuan et al., 2013Yuan, C.M., Tang, G.H., Wang, X.Y., Zhang, Y., Cao, M.M., Li, X.H., Li, Y., Li, S.L., Di, Y.T., He, H.P., Hao, X.J., Hua, H.M., 2013. New steroids and sesquiterpene from Turraea pubescens. Fitoterapia 90, 119–125.
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Turraea wakefieldii
|
Root bark |
Limonoids 11β,12α-diacetoxyneotecleanin, 11β,12α-diacetoxy-14β,15β-epoxyneotecleanin, 7α,12α-diacetoxy-14β,15β-epoxy-11β-hydroxyneotecleanin, 7α,12α-diacetoxy-11β-hydroxyneotecleanin, 11β,12α-diacetoxy-1-deoxo-14β,15β-epoxy-3β-hydroxy-2-oxo-neotecleanin |
Ndung'u et al., 2003Ndung’u, M., Hassanali, A., Hooper, A.M., Chhabra, S., Miller, T.A., Paul, R.L., Torto, B., 2003. Ring A-seco mosquito larvicidal limonoids from Turraea wakefieldii. Phytochemistry 64, 817–823.
|
Turraeanthus mannii
|
Root bark |
(3R,4R,3′R,4′R)-6,6′-dimethoxy-3,4,3′,4′-tetrahydro-2H,20H-[3,3′]bichromenyl-4,40-diol and 15-acetoxy-labda-8(17),12E,14Z-trien-16-alcoumarin derivative, chromenone, two labdane diterpenes and one pregnane steroid |
Sielinou et al., 2012Sielinou, V.T., Vardamides, J.C., Nkengfack, A.E., Laatsch, H., 2012. Phenolic derivatives and an antifungal and cytototoxic labdane diterpenoid from the root bark of Turraeanthus mannii. Phytochem. Lett. 5, 409–413.
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Turreanthus africanus
|
Seeds |
Two labdane diterpenoids and seco-tetranortriterpenoid. 12,15-epoxylabda-8(17),12,14-trien-16al and 16-acetoxy-12(R), 15-epoxy-15β-hydroxylabda-8 (17), 13 (16)-diene and a limonoid 17-epi 12-dehydroxy heudebolin |
Tane et al., 2004Tane, P., Akam, M.T., Tsopmo, A., Ndi, C.P., Sterner, O., 2004. Two lab danediterpenoids and a seco-tetranortriterpenoid from Turreanthus africanus. Phytochemistry 65, 3083–3087.
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Walsura chrysogyne
|
Barks |
Limonoids walsogyne A |
Mohamad et al., 2008Mohamad, K., Hirasawa, Y., Lim, C.S., Awang, K., Hadi, A.H.A., Takeya, K., Morita,H., 2008. Ceramicine A and walsogyne A, novel limonoids from two species of Meliaceae. Tetrahedron Lett. 49, 4276–4278.
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|
|
Limonoids, Walsogynes B-G |
Nugroho et al., 2013Nugroho, A.E., Okuda, M., Yamamoto, Y., Hirasawa, Y., Wong, C.P., Kaneda, T., Shirota, O., Hadi, A.H.A., Morita, H., 2013. Walsogynes B-G, limonoids from Walsura chrysogyne. Tetrahedron 69, 4139–4145.
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Walsura piscidia
|
Leaves |
Piscidinol F, apotirucallane |
Govindachari et al., 1995Govindachari, T.R., Krishna Kumari, G.N., Suresh, G., 1995. Triterpenoids from Wal-sura piscidia. Phytochemistry 39, 167–170.
|
|
Aerial parts |
Lup-20-(29)-ene-3β,30-diol and 5-hydroxy-7,3′,4′,5′-tetra methoxy flavones |
Balakrishna et al., 1995Balakrishna, K., Rao, R.B., Patra, A., Usman Ali, S., 1995. Constituents of Walsura piscidia. Fitoterapia 66, 548–550.
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Walsura robusta
|
Leaves |
Sesquiterpenoid 10β-nitro-isodauc-3-en-15-al, 10-oxo-isodauc-3-en-15-al |
Li et al., 2013aLi, H., Tang, G.H., Yu, Z., Hao, X.J., Qing, Z., He, H.P., 2013a. A new carotane sesquiterpene from Walsura robusta. Chin. J. Nat. Med. 11, 84–86.
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Walsura trichostemon
|
Roots |
Apotirucallane, trichostemonate |
Sichaem et al., 2012Sichaem, J., Aree, T., Khumkratok, S., Jong-aramruang, J., Tip-pyang, S., 2012. A new cytotoxic apotirucallane from the roots of Walsura trichostemon. Phytochem. Lett. 5, 665–667.
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Walsura trifoliata
|
Leaves and twigs |
Apo-tirucallane triterpenoids, piscidinone A and B |
Rao et al., 2012Rao, M.S.A., Suresh, G., Yadav, P.A., Prasad, K.R., Nayak, V.L., Ramakrishna, S., Rao, C.V., Babu, K.S., 2012. Novel apo-tirucallane triterpenoids from Walsura trifoliate. Tetrahedron Lett. 53, 6241–6244.
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Walsura yunnanensis
|
Bark |
Walsurin, isowalsuranolide, 11β-acetoxy walsuranolide and 20,22-dihydro-22,23-epoxy walsuranolide and 11β-hydroxy dihydrocedrelone, 11β-acetoxy dihydrocedrelone |
Luo et al., 2000dLuo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G., 2000d. Tetranortriterpenoids from Walsura yunnanensis. J. Nat. Prod. 63, 947–951.
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Xylocarpus granatum
|
Bark |
Friedelin, β-sitosterol, stigmasterol, methyl-3β-isopropyl-1-oxomeliacate, methyl-3β-acetoxy-oxomeliacate tria contanol |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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Phragmalin-type limonoids, xyloccensins Q-U along with xyloccensin P |
Cui et al., 2005Cui, J., Deng, Z., Li, J., Fu, H., Proksch, P., Lin, W., 2005. Phragmalin-type limonoids from the mangrove plant Xylocarpus granatum. Phytochemistry 66, 2334–2339.
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Three mexicanolides, xyloccensins L-N and eight 8, 9, 30-phragmalin ortho esters, named xyloccensins O-V |
Wu et al., 2006Wu, J., Xiao, Q., Li, Q., 2006. Limonoids from the Mangrove Xylocarpus granatum. Biochem. Syst. Ecol. 34, 838–841.
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Fruit |
Xyloccensin K, W, aurantiamide, daucosterol, (β)-catechin, spicatin, 6-acetoxycedrodorin |
Wu et al., 2006Wu, J., Xiao, Q., Li, Q., 2006. Limonoids from the Mangrove Xylocarpus granatum. Biochem. Syst. Ecol. 34, 838–841.
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Seeds |
Xyloccensin K |
Kokpol et al., 1996Kokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J., Rex, T.W.,1996. A Limonoid from Xylocarpus granatum. Phytochemistry 41, 903–905.
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Seven protolimonoids odoratone, grandifoliolenone, sapelin E acetate, holstinone B, C, hispidol B, piscidinol G |
Yin et al., 2009Yin, B., Huo, C., Shen, L., Wang, C., Zhao, L., Wang, Y., Shi, Q., 2009. Protolimonoidsfrom the seeds of Xylocarpus granatum. Biochem. Syst. Ecol. 37, 218–220.
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Xylocarpus moluccensis
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Seeds |
Xyloccensins A, B, C, D, E, F and methyl angolensate |
Rastogi and Mehrotra, 1993Rastogi, R.P., Mehrotra, B.N., 1993. Compendium of Indian Medicinal Plants, vol. 2. CDRI, Lucknow, New Delhi, Publications and Information Directorate.
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Godavarins A-J along with eight known limonoids, viz. xyloccensins L, P, Q, mexicanolide, 6-deoxy-3-detigloyl-swietenine acetate, fissinolide, methyl 3β-acetoxy-1-oxomeliaca-8(30), 14-dienoate, and methyl 3β-acetoxy-1-oxomeliaca-8(9),14-dienoate |
Li et al., 2010Li, J., Li, M.Y., Feng, G., Xiao, Q., Sinkkonen, J., Satyanandamurty, T., Wu, J., 2010. Limonoids from the seeds of a Godavari mangrove, Xylocarpus moluccensis. Phytochemistry 71, 1917–1924.
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Thaixylomolins D-F |
Li et al., 2013bLi, J., Li, M.Y., Xiao, Q., Pedpradab, P., Wu, J., 2013b. Thaixylomolins D-F, new limonoids from the Thai true mangrove, Xylocarpus moluccensis. Phytochem. Lett. 6, 482–485.
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