Ferulic acid (FERH) is known to exert leishmanicidal action against Leishmania (Leishmania) amazonensis. In this study, the ferulate anion (FER–) was intercalated into a layered double hydroxide (LDH) for FER– delivery during an antileishmania in vitro test. The LDH-FER– intercalation compound was prepared by coprecipitation and was characterized by X-ray powder diffraction, thermogravimetry, UV-Vis, infrared, and Raman spectroscopy analyses. Leishmania (L.) amazonensisin vitro assays were conducted to assess the LDH-FER– potential. LDH-FER– was found to promote a dose-dependent reduction of L. (L.) amazonensis amastigotes (intracellular form, half maximal inhibitory concentration (IC50) = 1.78 µg mL-1) without exerting a deleterious effect on the host macrophages (medium cytotoxic concentration (CC50) = 212.61 µg mL-1 and selectivity index = 119.4). LDH-FER– was found to be an effective inhibitor of the amastigote form of L. (L.) amazonensis, suggesting that LDH-FER– was able to deliver FER– inside the parasitophorous vacuoles where the pH is more acidic.

The purification of the hexanic extract from the leaves of a native variety of mahogany collected in Santarém (Pará, Brazil) afforded eight new phragmalin limonoids along with eight known compounds. This variety, according to field observations, should be considered resistant against the specialist insect Hypsipyla grandella, that attacks the terminal shoots only of juvenile mahogany and not of matured ones. After observing that four phragmalin limonoids were present just in mature leaves, we carried out two bioassays, one of them using a fraction from hexanic extract of mature leaves and another using a mix of four limonoids. The results of the bioassay using the isolated limonoids showed a direct effect on the larvae of H. grandella, suggesting that these limonoids act as inhibitors of larvae growth. This should be the reason why larvae choose the young leaves for their development.

A new compound, 5,7,3'-trihydroxy-4'-methoxy-8-prenylisoflavone, was isolated from the leaves of Vatairea guianensis Aubl. (Fabaceae), together with two known isoflavones lupiwighteone and 5,7,4'-trihydroxy-3'-methoxy-8-prenylisoflavone. All isolated compounds were characterized based on infrared (IR), UV, 1H and 13C nuclear magnetic resonance (NMR), including 2D NMR analyses and high resolution mass spectrometry. The ethanolic extract from V. guianensis leaves displayed activity against Candida dubliniensis, C. albicans and C. krusei. However, the EtOAc fraction from that extract exhibited more significant activity than the ethanolic extract, showing antifungal activity for all fungi species investigated. The major compound 5,7,3'-trihydroxy-4'-methoxy-8-prenylisoflavone isolated from that EtOAc fraction was also active against C. parapsilosis and C. dubliniensis.

Das folhas de Vatairea guianensis Aublé foram isoladas quatro isoflavonas identificadas como, 5,3',-diidroxi-4'-metoxi-2",2"-dimetilpirano-(5",6":8,7)-isoflavona ( 1: ), 5,7-diidroxi-3',4'-metilenodioxi-8-prenil-isoflavona ( 2: ) e 5,3'-diidroxi-4'-metoxi-7-O-β-glicopiranosídeo-8-prenil-isoflavona ( 3: ) e derrona ( 4: ), juntamente com cinco triterpenos identificados em mistura de lupeol, α-amirina, β-amirina, germanicol e ácido betulínico. As substâncias 1: 3: são novos produtos naturais, porém 1: e 2: já foram citados como produtos de síntese. No entanto, todas essas substâncias são relatadas pela primeira vez para essa espécie. Suas estruturas químicas foram elucidadas com base nos seus dados de ressonância magnética nuclear (RMN) 1D e 2D e por espectrometria de massas de alta resolução. O extrato etanólico das folhas e os compostos 1-3: foram avaliados quanto ao seu potencial sequestrador do radical DPPH• (2,2-difenil-1-picril-hidrazila) e os resultados mostram que o extrato apresentou alta atividade (CI50 = 6,2 ± 0,4 µg mL-1), enquanto as substâncias testadas apresentaram baixo poder antioxidante (CI50 ≥ 29,5 ± 2,5 µg mL-1) quando comparadas com TROLOX (CI50 = 4,5 ± 0,4 µg mL-1).

Four isoflavones were isolated from Vatairea guianensis Aublé leaves and identified as 5,3'-dihydroxy-4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-isoflavone ( 1: ), 5,7-dihydroxy-3',4'-methylenedioxy-8-prenyl-isoflavone ( 2: ), 5,3'-dihydroxy-4'-methoxy-7-O-β-glucopyranoside-8-prenyl-isoflavone ( 3: ) and derrone ( 4: ) together with five triterpenes identified in mixture, lupeol, α-amyrin, β-amyrin, germanicol and betulinic acid. Substances 1: 3: are novel natural products, although 1: and 2: have been cited as synthetic products. However, all these compounds are first reported from this species. Their chemical structures were elucidated based on their 1D and 2D nuclear magnetic resonance (NMR) data and high resolution mass spectrometry. The ethanol extract from the leaves and 1: 3: were evaluated for their potential in scavenging DPPH• (2,2-diphenyl-1-picrylhydrazylradical) and the results showed that the extract presented high activity (IC50 = 6.2 ± 0.4 µg mL-1), while the isolated compounds showed low antioxidant power (IC50 ≥ 29.5 ± 2.5 µg mL-1) when compared to Trolox (IC50 = 4.5 ± 0.4 µg mL-1).

Das folhas de Deguelia utilis foram isolados cinco flavonoides: 5,3'-di-hidróxi-4'-metóxi2'',2''-dimetilcromeno-(5'',6'':6,7)-di-hidroflavonol (1), 5,3'-di-hidróxi-7,4'-dimetóxi-6,8dimetilalil-di-hidroflavonol (2), 5,3'-di-hidróxi-4'-metóxi-8-prenil-2'',2''-dimetilcromeno(5'',6'':6,7)-flavanona (3), 5,3'-di-hidróxi-7,4'-dimetóxi-6,8-dimetilalil-flavanona (4), 3,5,3'-tri-hidróxi-7,4'-dimetóxi-6,8-dimetilalil-flavanol (5), juntamente com os estilbenos: 4-metoxilonchocarpeno (6) e lonchocarpeno (7). Suas estruturas químicas foram elucidadas com base nos seus dados de NMR (ressonância magnética nuclear) e HRESITOF-MS (espectrometria de massas de alta resolução por tempo de vôo, com ionização por eletrospray). Além disso, a fim de investigar o potencial efeito citoprotetor desses flavonoides, foi utilizada uma fração eluída com hexano:AcOEt contendo os sete flavonoides, em um modelo in vitro de neurodegeneração, utilizando culturas primárias do hipocampo de ratos neonatal (PND2-P3) expostos à rotenona, um inibidor mitocondrial do complexo I. Houve uma redução significativa da viabilidade celular (19,4 ± 1,6%), quando as culturas foram expostas à rotenona 30 nmol L-1 por 72 h. A exposição concomitante das culturas a FR3 (5 µg mL-1) e rotenona 30 nmol L-1 resultou em valores de viabilidade celular semelhante ao grupo controle (99,6 ± 4,8%), sugerindo um efeito citoprotetor para essa fração.

Five new flavonoids, 5,3'-dihydroxy-4'-methoxy-2'',2''-dimethylchromene-(5'',6'':6,7)dihydroflavonol (1), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-dihydroflavonol (2), 5,3'-dihydroxy-4'-methoxy-8-allyl-2'',2''-dimethylchromene-(5'',6'':6,7) flavanone (3), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-flavanone (4), 3,5,3'-trihydroxy-7,4'-dimethoxy6,8-dimethylallyl-flavanol (5), together with the stilbenes 4-methoxylonchocarpene (6) and lonchocarpene (7) were isolated from the leaves of Deguelia utilis. Their chemical structures were established on the basis of NMR (nuclear magnetic resonance) spectral data and HRESITOF-MS (electrospray ionization-high resolution time-of-flight mass spectrometry). Also, in order to investigate potential cytoprotective effects of these flavonoids, we used a fraction eluted with hexane:EtOAc containing all seven flavonoids, in an in vitro model of neurodegeneration, using hippocampal primary cultures from neonatal (PND2-P3) rats exposed to rotenone, a mitochondrial complex I inhibitor. There was a significant reduction in cell viability (19.4 ± 1.6%) when the cultures were exposed to 30 nmol L-1 rotenone for 72 h. Concomitant exposure of the cultures to the FR3 (5 µg mL-1) and 30 nmol L-1 rotenone resulted in values of cell viability similar to control groups (99.6 ± 4.8%), strongly suggesting a cytoprotective effect for this flavonoid-rich fraction.

A biodiversidade Amazônica pode ser uma fonte de substâncias capazes de serem utilizadas no controle de plantas daninhas. Neste estudo relatamos o isolamento e a identificação de cinco estilbenos a partir das folhas do "timbó vermelho" (Deguelia rufescens var. urucu): 4-metoxilonchocarpeno (1); 3,5-dimetoxi-4´-hidroxi-3´-prenil-trans-estilbeno (2), lonchocarpeno (3), 3,5-dimetoxi-4´-O-prenil-trans-estilbeno (4) e pteroestilbeno (5). As substâncias 2 e 4 são novos produtos naturais, porém 2 já havia sido citada como produto de síntese. Foi avaliada a potencial atividade alelopática de 1, 2 e 4 sobre a germinação de sementes e o crescimento da planta daninha Mimosa pudica. Os efeitos observados sobre a germinação das sementes de M. pudica não variaram significantemente (p > 0,05) quando a análise da fitotoxidade foi realizada com as substâncias isoladamente, cuja inibição máxima não ultrapassou 20%. A inibição mais intensa, quanto ao desenvolvimento da radícula e do hipocótilo, foi encontrada para o composto 4 (p < 0,05). Isoladamente, 4 causou efeito inibitório significativamente maior (p < 0,05) no desenvolvimento da radícula e do hipocótilo, do que 1 e 2. Quando testados aos pares, apresentaram antagonismo para a germinação de sementes e sinergismo para o desenvolvimento da radícula e hipocótilo.

The Amazon biodiversity may provide plants whose chemical substances are capable of controlling weeds. In this study we report the isolation and identification of five stilbenes from the leaves of "timbó vermelho" (Deguelia rufescens var. urucu): 4-methoxylonchocarpene (1); 3,5-dimethoxy-4´-hydroxy-3´-prenyl-trans-stilbene (2), lonchocarpene (3), 3,5-dimethoxy-4´-O-prenyl-trans-stilbene (4) and pterostilbene (5). Compounds 2 and 4 are new natural products although 2 has been previously cited as synthesis product. Potential allelopathic activity for 1, 2 and 4 was evaluated over seed germination and plant growth of Mimosa pudica weed. The observed effects on seed germination did not vary significantly (p > 0.05) when the analysis of phytotoxicity was performed with the substances alone, the maximum inhibition did not exceed 20%. The most intense inhibitions on radicle and hypocotyl development were found for compound 4 (p < 0.05). When tested in pairs, showed antagonism for seed germination and synergism for radicle and hypocotyl development.

O presente trabalho trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7"-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de ¹H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC.) Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC) procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol), four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside), one isoflavone (5,7,4'-trimethoxyisoflavone), one flavone (5,4'-dihydroxy-7,3',5'-trimethoxyflavone) and four biflavones (amenthoflavone, 7,7"-O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone). The structures of the compounds were established by the analysis of ¹H, 13C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.

Derris urucu é uma planta da Amazônia com propriedades inseticida e ictiotóxica. Estudos com esta espécie reportam a presença de flavonóides, principalmente rotenóides, bem como de estilbenos. A partir do extrato etanólico das folhas de Derris urucu (Leguminosae), três novos diidroflavonóides, denominados urucuol A (1), B (2) e C (3) e o diidroflavonol isotirumalina (4), foram isolados e identificados. As estruturas destes compostos foram elucidadas por uma extensiva análise espectroscópica de RMN uni e bidimensional, UV, IV e dados de EM, além de comparação com dados da literatura. Os compostos isolados (1-4) foram avaliados quanto ao seu potencial sequestrador do radical DPPH• e apresentaram baixo poder antioxidante quando comparados ao antioxidante comercial trans-resveratrol.

Derris urucu is an Amazonian plant with insecticide and ichthyotoxic properties. Studies with this species show the presence of flavonoids, mainly rotenoids, as well as stilbenes. The ethanol extract of the leaves of Derris urucu (Leguminosae) afforded three new dihydroflavonols named urucuol A (1), B (2) and C (3), and the dihydroflavonol isotirumalin (4). Their structures were elucidated by extensive analysis of 1D and 2D NMR, UV and IR spectra and MS data and comparison with literature data. The isolated compounds (1-4) were evaluated for DPPH• radical scavenging activity and showed a relatively lower antioxidant ability compared to the commercial antioxidant trans-resveratrol.

Um extrato metanol-água das folhas de Inga edulis foi fracionado para identificar os compostos polifenólicos. Os compostos identificados foram o acido gálico, a catequina, a epicatequina, a miricetina-3-ramnopiranosídeo, a quercetina-3-glucopiranosídeo e a quercetina-3-ramnopiranosídeo. A capacidade antioxidante do extrato e dos polifenóis puros foi medida pelo teste ORAC e comparada com o teor em fenólicos totais (TP). O extrato bruto seco apresentou valores de ORAC (11.16 mmol TE per g) e TP (496.5 mg GAE per g) muito altos. Os compostos identificados foram responsáveis, respectivamente, por 9.53 % e 12.10 % dos valores ORAC e de TP do extrato de folhas de Inga edulis.

A methanol-water extract of Inga edulis leaves was fractionated to identify the polyphenolic compounds. The identified compounds were gallic acid, catechin, epicatechin, myricetin-3-rhamnopyranoside, quercetin-3-glucopyranoside and quercetin-3-rhamnopyranoside. The antioxidant activity of the extract and of pure polyphenols was measured by the ORAC assay and compared with the Total Phenolic (TP) content. The dry crude extract presented very high values for ORAC (11.16 mmol TE per g) and TP (496.5 mg GAE per g). The identified compounds were responsible for 9.53 % and 12.10 % of the ORAC value and TP content of the Inga edulis leaf extract, respectively.

Duas novas flavonas, 5 -hidroxi -7,5' -dimetoxi -3',4' -metilenodioxiflavona e 5 -hidroxi -7,3',5' -trimetoxi -4' -(3,3 -dimetilaliloxi) flavona foram isoladas das folhas de Ficus gomelleira, juntamente com três flavonas conhecidas, a 5,6,7,3',4',5' -hexametoxiflavona, 5 -hidroxi -8,3',4' -trimetoxi -2'',2'' -dimetilpirano (5",6":6,7) -flavona e 5 -hidroxi -8,3',4',5' -tetrametoxi -2'',2'' -dimetilpirano (5",6":6,7) -flavona. As estruturas das substâncias isoladas foram elucidadas com base na análise de seus dados espectrais, bem como por comparação com dados da literatura.

Two new flavones, 5 -hydroxy -7,5' -dimethoxy -3',4' -methylenedioxyflavone and 5 -hydroxy -7,3',5' -trimethoxy -4' -(3,3 -dimethylallyloxy) flavone, as well as three known flavones: 5,6,7,3',4',5' -hexamethoxyflavone, 5 -hydroxy -8,3',4' -trimethoxy -2'',2'' -dimethylpyrano (5",6":6,7) -flavone and 5 -hydroxy -8,3',4',5' -tetramethoxy -2'',2'' -dimethylpyrano (5",6":6,7) -flavone were isolated from the leaves of Ficus gomelleira. Their structures were elucidated by spectroscopic methods and comparison with literature data.