6α,7β-Diacetoxyvouacap14(17)-ene (16) |
(α) OAc |
(β) OAc |
C === Inserir caracter correspondente ao PDF === CH2
|
|
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525.
|
7β-Acetoxyvouacapane (17) |
(α) H |
(β) OAc |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Spindola et al. (2009)Spindola, H.M., Carvalho, J.E., Ruiz, A.L.T.G., Rodrigues, R.A.F., Denny, C., Sousa, I.M.O., Tamashiro, J.Y., Foglio, M.A., 2009. Furanoditerpenes from Pterodon pubescens Benth. with selective in vitro anticancer activity for prostate cell line. J. Braz. Chem. Soc. 20, 569-575.
|
6α,7β-Diacetoxyvouacapane (18) |
(α) OAc |
(β) OAc |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Spindola et al. (2009)Spindola, H.M., Carvalho, J.E., Ruiz, A.L.T.G., Rodrigues, R.A.F., Denny, C., Sousa, I.M.O., Tamashiro, J.Y., Foglio, M.A., 2009. Furanoditerpenes from Pterodon pubescens Benth. with selective in vitro anticancer activity for prostate cell line. J. Braz. Chem. Soc. 20, 569-575.
|
Vouacapane-6α,7β,14β-triol (19) |
(α) OH |
(β) OH |
(α) Me |
(β) OH |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203.
|
6α,7β-Dihydroxyvouacapan-17β-oate sodium (20) |
(α) OH |
(β) OH |
(β) COONa |
(α) H |
(α) Me |
(β) Me |
Duarte et al. (1992Duarte, I.D.G., Alves, D.L.F., Craig, M.N., 1992. Possible participation of endogenous opioid peptides on the mechanism involved in analgesia induced by vouacapano. Life Sci. 50, 891-897., 1996)Duarte, I.D.G., Alves, D.L.F., Veloso, D.P., Craig, M.N., 1996. Evidence of the involvement of biogenic amines in the antinociceptive effect of a vouacapan extracted from Pterodon polygalaflorus Benth. J. Ethnopharmacol. 55, 13-18.
|
6α,7β-Dihydroxyvouacapan-17β-oic acid (21) |
(α) OH |
(β) OH |
(β) COOH |
(α) H |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Campos et al. (1994)Campos, A.M., Silveira, E.R., Braz-Filho, R., Teixeira, T.C., 1994. Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36, 403-406., Demuner et al. (1996)Demuner, A.J., Barbosa, L.C.A., Veloso, D.P., Alves, L.D.F., Howarth, O.W., 1996. Structure and plant growth regulatory activity of new diterpenes from Pterodon polygalaeflorus. J. Nat. Prod. 59, 770-772., Belinelo et al. (2002)Belinelo, V.J., Reis, G.T., Stefani, G.M., Alves, D.L.F., Veloso, D.P., 2002. Derivatives and its activities on the electrically stimulated guinea-pig ileum preparation. J. Braz. Chem. Soc. 13, 830-837., Rubinger et al. (2004)Rubinger, M.M.M., Branco, P.A.C., Guilardi, S., Souza, E.M.R., Gambardella, M.T.P., Borges, E.E.L., Alves, D.L.F., Veloso, D.P., 2004. Preparation, X-ray structural studies and plant growth regulatory activity of methyl 6α,7β-Thiocarbonydioxyvouacapan-17β-oate. J. Braz. Chem. Soc. 15, 219-223., Omena et al. (2006)Omena, M.C., Bento, E.S., Paula, J.E., Sant'ana, A.E.G., 2006. Larvicidal diterpenes from Pterodon polygalaeflorus. Vector Borne Zoonotic Dis. 6, 216-222., Díaz et al. (2006Díaz, B.K., Santos, F.J., Rubinger, M.M., Veloso, D.P., Hennsen, B.L., 2006. A diterpene γ-lactone derivative from Pterodon polygalaeflorus Benth. as a photosystem II inhibitor and uncoupler of photosynthesis. J. Biosci. 61, 227-233., 2010)Díaz, B.K., Branco, P.A.C., Santos, F.J.L., Rubinger, M.M.M., Alves, D.L.F., Veloso, D.P., Hennsen, B.L., 2010. Furanoditerpene ester and thiocarbonyl deoxy derivatives inhibit photosynthesis. Pest. Biochem. Physiol. 96, 119-126., Branco et al. (2008)Branco, P.A.C., Santos, F.J.L., Rubinger, M.M.M., Alves, D.L.F., Veloso, D.P., Díaz, B.K., Hennsen, B.L., 2008. Inhibition and uncoupling of photosynthetic electron transport by diterpene lactone amide derivatives. J. Biosci. 63, 251-259., Santos et al. (2008)Santos, F.J.L., Alcântara, A.F.C., Alves, D.L.F., Veloso, D.P., 2008. Theoretical and experimental NMR studies of the Swern oxidation of methyl 6α,7β-dihydroxyvouacapan-17β-oate. Struct. Chem. 19, 625-631., Euzébio et al. (2009Euzébio, F.P.G., Santos, F.J.L., Veloso, D.P., Ruiz, A.L.T.G., Carvalho, J.E., Alves, D.L.F., Fátima, A., 2009. Effect of 6α,7β-dihydroxyvouacapan-17β-oic acid and its lactone derivatives on the growth of human cancer cells. Bioorg. Chem. 37, 96-100., 2010)Euzébio, F.P.G., Santos, F.J.L., Veloso, D.P., Alcântara, A.F.C., Ruiz, A.L.T.G., Carvalho, J.E., Foglio, M.A., Alves, D.L.F., Fátima, A., 2010. Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives. Bioorg. Med. Chem. 18, 8172-8177., Galceran et al. (2011)Galceran, C.B., Sertie, J.A.A., Lima, C.S., Carvalho, J.C.T., 2011. Anti-inflammatory and analgesic effects of 6α,7β-dihydroxyvouacapan-17β-oic acid isolated from Pterodon emarginatus Vog. fruits. Inflammopharmacology 19, 139-143.
|
Methyl 6α,7β-dihydroxyvouacapan-17β-oate (22) |
(α) OH |
(β) OH |
(β) COOMe |
(α) H |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Arriaga et al. (2000)Arriaga, A.M.C., Castro, M.A.B., Silveira, E.R., Braz-Filho, R., 2000. Further diterpenoids isolated from Pterodon polygalaeflorus. J. Braz. Chem. Soc. 11, 187-190., Rubinger et al. (2004)Rubinger, M.M.M., Branco, P.A.C., Guilardi, S., Souza, E.M.R., Gambardella, M.T.P., Borges, E.E.L., Alves, D.L.F., Veloso, D.P., 2004. Preparation, X-ray structural studies and plant growth regulatory activity of methyl 6α,7β-Thiocarbonydioxyvouacapan-17β-oate. J. Braz. Chem. Soc. 15, 219-223., Omena et al., 2006Omena, M.C., Bento, E.S., Paula, J.E., Sant'ana, A.E.G., 2006. Larvicidal diterpenes from Pterodon polygalaeflorus. Vector Borne Zoonotic Dis. 6, 216-222., Santos et al. (2008)Santos, F.J.L., Alcântara, A.F.C., Alves, D.L.F., Veloso, D.P., 2008. Theoretical and experimental NMR studies of the Swern oxidation of methyl 6α,7β-dihydroxyvouacapan-17β-oate. Struct. Chem. 19, 625-631., Spindola et al. (2009Spindola, H.M., Carvalho, J.E., Ruiz, A.L.T.G., Rodrigues, R.A.F., Denny, C., Sousa, I.M.O., Tamashiro, J.Y., Foglio, M.A., 2009. Furanoditerpenes from Pterodon pubescens Benth. with selective in vitro anticancer activity for prostate cell line. J. Braz. Chem. Soc. 20, 569-575., 2010Spindola, H.M., Servat, L., Denny, C., Rodrigues, R.A.F., Eberlin, M.N., Cabral, E., Souza, I.M.O., Tamashiro, J.Y., Carvalho, J.E., Foglio, M.A., 2010. Antinociceptive effect of geranylgeraniol and 6α,7β-dihydroxyvouacapan-17β-oate methyl ester isolated from Pterodon pubescens Benth. BMC Pharm. 10, http://dx.doi.org/10.1186/1471-2210-10-1. http://dx.doi.org/10.1186/1471-2210-10-1...
, 2011)Spindola, H.M., Servat, L., Rodrigues, R.A.F., Sousa, I.M.O., Carvalho, J.E., Foglio, M.A., 2011. Geranylgeraniol and 6α,7β-dihydroxyvouacapan-17β-oate methyl ester isolated from Pterodon pubescens Benth.: further investigation on the antinociceptive mechanism of action. Eur. J. Pharmacol. 656, 45-51., Díaz et al. (2010)Díaz, B.K., Branco, P.A.C., Santos, F.J.L., Rubinger, M.M.M., Alves, D.L.F., Veloso, D.P., Hennsen, B.L., 2010. Furanoditerpene ester and thiocarbonyl deoxy derivatives inhibit photosynthesis. Pest. Biochem. Physiol. 96, 119-126.
|
Methyl 7β-acetoxy-6α-hydroxyvouacapan-17β-oate (23) |
(α) OH |
(β) OAc |
(β) COOMe |
(α) H |
(α) Me |
(β) Me |
Mahajan and Monteiro (1973)Mahajan, J.R., Monteiro, M.B., 1973. New diterpenoids from Pterodon emarginatus Vog. J. Braz. Chem. Soc. 42, 520-525., Servat et al. (2012)Servat, L., Spindola, H.M., Rodrigues, R.A.F., Sousa, I.M.O., Ruiz, A.L.T.G., Carvalho, J.E., Foglio, M.A., 2012. Pterodon pubescens Benth.: stability study of microencapsulated extract and isolated compounds monitored by antinociceptive assays. J. Braz. Chem. Soc. 23, 1244-1253.
|
6α,7β-diacetoxyvouacapan-14β-al (24) |
(α) OAc |
(β) OAc |
(α) H |
(β) CHO |
(α) Me |
(β) Me |
Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203.
|
6α,7β-Diacetoxyvouacapan-14β-oate (25) |
(α) OAc |
(β) OAc |
(α) H |
(β) COOMe |
(α) Me |
(β) Me |
Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203.
|
Methyl 6α-acetoxy-7β-hydroxyvouacapan-17β-oate (26) |
(α) OAc |
(β) OH |
(β) COOMe |
(α) H |
(α) Me |
(β) Me |
Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Campos et al. (1994)Campos, A.M., Silveira, E.R., Braz-Filho, R., Teixeira, T.C., 1994. Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36, 403-406., Hoscheid et al. (2012)Hoscheid, J., Reinas, A., Cortez, D.A.G., Costa, W.F., Cardoso, M.L.C., 2012. Determination by GC–MS-SIM of furanoditerpenes in Pterodon pubescens Benth.: development and validation. Talanta 100, 372-376., Servat et al. (2012)Servat, L., Spindola, H.M., Rodrigues, R.A.F., Sousa, I.M.O., Ruiz, A.L.T.G., Carvalho, J.E., Foglio, M.A., 2012. Pterodon pubescens Benth.: stability study of microencapsulated extract and isolated compounds monitored by antinociceptive assays. J. Braz. Chem. Soc. 23, 1244-1253., Oliveira et al. (2017)Oliveira, L.A.R., Oliveira, G.A.R., Lemes, G.F., Romão, W., Vaz, B.G., Albuquerque, S., Gonçalez, C., Lião, L.M., Bara, M.T.F., 2017. Isolation and structural characterization of two new furanoditerpenes from Pterodon emarginatus (Fabaceae). J. Braz. Chem. Soc., http://dx.doi.org/10.21577/0103-5053.20170118. http://dx.doi.org/10.21577/0103-5053.201...
|
Methyl 6α-hydroxy-7β-acetoxyvouacapan-17β-oate (27) |
(α) OH |
(β) OAc |
(β) COOMe |
(α) H |
(α) Me |
(β) Me |
Fascio et al. (1976)Fascio, M., Mors, W.B., Gilbert, B., Mahajan, J.R., Monteiro, M.B., Santos Filho, D., Vichnewski, W., 1976. Diterpenoid furans from Pterodon species. Phytochemistry 15, 201-203., Hoscheid et al. (2012)Hoscheid, J., Reinas, A., Cortez, D.A.G., Costa, W.F., Cardoso, M.L.C., 2012. Determination by GC–MS-SIM of furanoditerpenes in Pterodon pubescens Benth.: development and validation. Talanta 100, 372-376., Servat et al. (2012)Servat, L., Spindola, H.M., Rodrigues, R.A.F., Sousa, I.M.O., Ruiz, A.L.T.G., Carvalho, J.E., Foglio, M.A., 2012. Pterodon pubescens Benth.: stability study of microencapsulated extract and isolated compounds monitored by antinociceptive assays. J. Braz. Chem. Soc. 23, 1244-1253.
|
6α-Hydroxy-7β-acetoxyvouacap-14(17)-ene (28) |
(α) OH |
(β) OAc |
C = CH2
|
|
(α) Me |
(β) Me |
Campos et al. (1994)Campos, A.M., Silveira, E.R., Braz-Filho, R., Teixeira, T.C., 1994. Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36, 403-406.
|
Vouacapane-6α,7β,14β,19-tetraol (29) |
(α) OH |
(β) OH |
(α) Me |
(β) OH |
(β) CH2OH |
(α) Me |
Demuner et al. (1996)Demuner, A.J., Barbosa, L.C.A., Veloso, D.P., Alves, L.D.F., Howarth, O.W., 1996. Structure and plant growth regulatory activity of new diterpenes from Pterodon polygalaeflorus. J. Nat. Prod. 59, 770-772., Arriaga et al. (2000)Arriaga, A.M.C., Castro, M.A.B., Silveira, E.R., Braz-Filho, R., 2000. Further diterpenoids isolated from Pterodon polygalaeflorus. J. Braz. Chem. Soc. 11, 187-190., Vieira et al. (2008)Vieira, C.R., Marques, M.F., Soares, P.R., Matuda, L., Oliveira, C.M.A., Kato, L., Silva, C.C., Guillo, L.A., 2008. Antiproliferative activity of Pterodon pubescens Benth. seed oil and its active principle on human melanoma cells. Phytomedicine 15, 528-532.
|
6α-Acetoxyvouacapane (30) |
(α) OAc |
(β) H |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Pimenta et al. (2006)Pimenta, A.T.A., Santiago, G.M.P., Arriaga, A.M.C., Menezes, G.H.A., Bezerra, S.B., 2006. Estudo fitoquímico e avaliação da atividade larvicida de Pterodon polygalaeflorus Benth. (Leguminosae) sobre Aedes aegypti. Rev. Bras. Farmacogn. 16, 501-505.
|
6α-Hydroxyvouacapane (31) |
(α) OH |
(β) H |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Arriaga et al. (2000)Arriaga, A.M.C., Castro, M.A.B., Silveira, E.R., Braz-Filho, R., 2000. Further diterpenoids isolated from Pterodon polygalaeflorus. J. Braz. Chem. Soc. 11, 187-190., Pimenta et al. (2006)Pimenta, A.T.A., Santiago, G.M.P., Arriaga, A.M.C., Menezes, G.H.A., Bezerra, S.B., 2006. Estudo fitoquímico e avaliação da atividade larvicida de Pterodon polygalaeflorus Benth. (Leguminosae) sobre Aedes aegypti. Rev. Bras. Farmacogn. 16, 501-505.
|
Vouacapane (32) |
(α) H |
(β) H |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Pimenta et al. (2006)Pimenta, A.T.A., Santiago, G.M.P., Arriaga, A.M.C., Menezes, G.H.A., Bezerra, S.B., 2006. Estudo fitoquímico e avaliação da atividade larvicida de Pterodon polygalaeflorus Benth. (Leguminosae) sobre Aedes aegypti. Rev. Bras. Farmacogn. 16, 501-505.
|
6α,7β-Dihydroxyvouacapan-17β-methylene-ol (33) |
(α) OH |
(β) OH |
(β) CH2OH |
(α) H |
(α) Me |
(β) Me |
Spindola et al. (2009)Spindola, H.M., Carvalho, J.E., Ruiz, A.L.T.G., Rodrigues, R.A.F., Denny, C., Sousa, I.M.O., Tamashiro, J.Y., Foglio, M.A., 2009. Furanoditerpenes from Pterodon pubescens Benth. with selective in vitro anticancer activity for prostate cell line. J. Braz. Chem. Soc. 20, 569-575.
|
6α-Acetoxy-7β-hydroxyvouacapan (34) |
(α) OAc |
(β) OH |
(α) Me |
(β) H |
(α) Me |
(β) Me |
Spindola et al. (2009)Spindola, H.M., Carvalho, J.E., Ruiz, A.L.T.G., Rodrigues, R.A.F., Denny, C., Sousa, I.M.O., Tamashiro, J.Y., Foglio, M.A., 2009. Furanoditerpenes from Pterodon pubescens Benth. with selective in vitro anticancer activity for prostate cell line. J. Braz. Chem. Soc. 20, 569-575.
|
6α,19β-Diacetoxy-7β,14β-dihydroxyvouacapan (35) |
(α) OAc |
(β) OH |
(β) OH |
(α) Me |
(α) Me |
(α) OAc |
Oliveira et al. (2017)Oliveira, L.A.R., Oliveira, G.A.R., Lemes, G.F., Romão, W., Vaz, B.G., Albuquerque, S., Gonçalez, C., Lião, L.M., Bara, M.T.F., 2017. Isolation and structural characterization of two new furanoditerpenes from Pterodon emarginatus (Fabaceae). J. Braz. Chem. Soc., http://dx.doi.org/10.21577/0103-5053.20170118. http://dx.doi.org/10.21577/0103-5053.201...
|
6α-Acetoxy-7β,14β-dihydroxyvouacapan (36) |
(α) OAc |
(β) OH |
(β) OH |
(α) Me |
(α) Me |
(β) Me |
Oliveira et al. (2017)Oliveira, L.A.R., Oliveira, G.A.R., Lemes, G.F., Romão, W., Vaz, B.G., Albuquerque, S., Gonçalez, C., Lião, L.M., Bara, M.T.F., 2017. Isolation and structural characterization of two new furanoditerpenes from Pterodon emarginatus (Fabaceae). J. Braz. Chem. Soc., http://dx.doi.org/10.21577/0103-5053.20170118. http://dx.doi.org/10.21577/0103-5053.201...
|