Dibenzylbutyrolactone lignans from Virola sebifera

Lopes, Lucia Maria Xavier; Yoshida, Massayoshi; Gottlieb, Otto R.

doi:10.1016/s0031-9422(00)84055-8

Cited by 71 publications

(51 citation statements)

References 6 publications

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“…Weber, 1989) and 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone (Lopes et al, 1983) by co-TLC and by comparison of the spectral data (MS and NMR) with authentic samples as described in the literature (Fig. 1).…”

Section: Resultsmentioning

confidence: 98%

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production

Lee

Ban

Kim

et al. 2005

Phytotherapy Research

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The chloroform and the ethyl acetate fractions from the roots of Acanthopanax chiisanensis exhibited the significant inhibition of TPA-induced prostaglandin E(2) (PGE(2)) production in rat peritoneal macrophages. Five lignans were isolated from the chloroform fraction and their structures were elucidated as l-sesamin, helioxanthin, savinin, taiwanin C, and 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone. Among the lignans tested, taiwanin C showed the most potent inhibitory activity (IC(50) = 0.12 microM) on PGE(2) production with the relative order of potency, taiwanin C >> 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone > savinin = helioxanthin. l-Sesamin showed no inhibitory activity at 30 microM.

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Section: Resultsmentioning

confidence: 98%

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production

Lee

Ban

Kim

et al. 2005

Phytotherapy Research

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“…Lignans containing β-and α-ethoxy groups at C-9 have been isolated previously from some Piper 7-10 and Dacrydium [11][12] species. The structures of two diastereomeric lignans (3 and 4) [13][14][15][16][17] , neolignan eupomatenoid-7 (5) 6 and α-tocopherylquinone (6) 18-21 were established on the basis of their spectral data and comparison with those of the analogous compounds recorded in previous reports.…”

Section: Resultsmentioning

confidence: 99%

Two Dibenzylbutyrolactol Derivatives and Other Chemical Constituents from Aristolochia peltato-deltoidea

Silva¹,

Palmeira²,

Conserva³

et al. 1999

J. Braz. Chem. Soc.

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Do extrato hexânico das partes aéreas de Aristolochia peltato-deltoidea Hoehne (Aristolochiaceae) foram isolados duas novas lignanas epiméricas do tipo dibenzilbutirolactol, rel-(8R, 8'S, 9S)-3,4-dimetoxi-3',4'-metilenodioxi-9β-etoxi-e rel-(8R, 8'S, 9R)-3,4-dimetoxi-3',4'-metilenodioxi-9α-etoxi-lignanas-8.8',9.O.9', além da neolignana benzofurânica eupomatenóide-7, α-tocoferilquinona, β-sitosterol e estigmasterol. Do extrato clorofórmico foram isoladas duas lignanas dibenzilbutirolactonas diasteroisoméricas:lenodioxi-9-oxo-lignanas-8.8',9.O.9'. A composição química das frações apolares do extrato hexânico também foi analisada por CG/EM. Dentre os componentes detectados, dez foram identificados. As estruturas dos compostos isolados foram elucidadas utilizando-se métodos espectrométricos.The hexane extract from the aerial parts of Aristolochia peltato-deltoidea Hoehne (Aristolochiaceae) afforded two new epimeric lignans dibenzylbutyrolactol type, rel-(8R, 8'S, 9S)-3,4-dimethoxy-3',4'-methylenodioxy-9β-ethoxy-and rel-(8R, 8'S, 9R)-3,4-dimethoxy-3',4'-methylenodioxy-9α-ethoxy-lignans-8.8',9.O.9', besides a benzofuran neolignan, known as eupomatenoid-7, α-tocopherylquinone, β-sitosterol and stigmasterol. From chloroform extract were isolated two diastereomeric dibenzylbutyrolactone lignans : rel-(8R, 8'R)-and rel-(8R, 8'S)-3,4-dimethoxy-3',4'-methylenodioxy-9-oxo-lignans-8.8',9.O.9'. Chemical composition analysis by GC/MS of the non polar fractions from hexane extract also was carried out and ten components were identified. The structures of the isolated compounds were elucidated utilizing spectrometric methods.

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“…Diversos grupos de substâncias como ácidos graxos, alcalóides, fl avonóides, lignóides, policetídeos, taninos e terpenos foram isolados e identifi cados principalmente das sementes, folhas e cascas de espécies de Virola (Barata et al, 2000;Blumenthal et al, 1997;Corothie;Nakano, 1969;Lopes et al, 1983;Martinez et al, 1999;Rezende;Kato, 2002).…”

Section: Introductionunclassified

Atividade antiproliferativa dos extratos e da fração orgânica obtidos das folhas de Virola sebifera Aubl. (Myristicaceae)

Denny

Zacharias

Kohn

et al. 2007

Rev. bras. farmacogn.

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RESUMO:As cascas de Virola sebifera (Myristicaceae) são utilizadas por populações indígenas amazônicas em preparações alucinógenas, nas quais foram encontrados alcalóides como a dimetiltriptamina e seus derivados. Considerando a enorme importância dos alcalóides isolados de plantas na terapêutica do câncer e a presença desses compostos em espécies de Virola, o presente trabalho teve por objetivo o estudo da atividade antiproliferativa em cultura de células tumorais humanas de extratos e da fração orgânica, obtidos das folhas de Virola sebifera. O extrato bruto diclorometânico (EBD) foi considerado o mais ativo, com seletividade principalmente para a linhagem de pulmão (NCI-460) -IC 50 : 4,46 g/mL e para a fração orgânica (FO) obtida por extração ácido-base -IC 50 ; 6,91 g/mL. A atividade observada possivelmente pode ser atribuída a alcalóides ou compostos nitrogenados que foram evidenciados pelo corante Dragendorff. Assim, a purifi cação da FO será necessária a fi m de comprovar a presença de compostos nitrogenados, através de isolamento e determinação estrutural, bem como a participação desses compostos na atividade antiproliferativa observada.Unitermos: Virola sebifera, Myristicaceae, atividade antiproliferativa, células tumorais, alcalóides.ABSTRACT: "Antiproliferative activity of extracts and fractions from Virola sebifera Aubl. leaves (Myristicaceae)". Barks of Virola sebifera (Myristicaceae) used by Amazonian Indian communities in hallucinogenic snuff preparations have yielded dimethyltryptamine and derivatives. Considering the importance of the alkaloids isolated from plants for the development of chemotherapy, and the presence of these compounds in several Virola species, the scope of this work was to evaluate the antiproliferative activity of the extracts and the organic fraction from Virola sebifera leaves. The crude dichloromethane extract was the most active with selectivity for lung line (NCI-460) -IC 50 : 4.46 g/mL, as well as the organic fraction (OF) -IC 50 : 6.91 g/mL. The observed activity could probably be attributed to alkaloids or nitrogen compounds that were evidenced by the Dragendorff reagent. However, the future purifi cation of OF will be necessary to prove the presence of alkaloids and their role in the antiproliferative activity in human cells as well as isolating and identifying these compounds.

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Dibenzylbutyrolactone lignans from Virola sebifera

Cited by 71 publications

References 6 publications

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production

Two Dibenzylbutyrolactol Derivatives and Other Chemical Constituents from Aristolochia peltato-deltoidea

Atividade antiproliferativa dos extratos e da fração orgânica obtidos das folhas de Virola sebifera Aubl. (Myristicaceae)

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Dibenzylbutyrolactone lignans from Virola sebifera

Cited by 71 publications

References 6 publications

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E2 production

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E2 production

Two Dibenzylbutyrolactol Derivatives and Other Chemical Constituents from Aristolochia peltato-deltoidea

Atividade antiproliferativa dos extratos e da fração orgânica obtidos das folhas de Virola sebifera Aubl. (Myristicaceae)

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Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E₂ production