Allenic germacranolides, bourbonene derived lactones and other constituents from Vernonia species

Bohlmann, Ferdinand; Jakupovic, Jasmin; Gupta, Rajinder K.; King, Robert M.; Robinson, Harold

doi:10.1016/s0031-9422(00)84169-2

Cited by 67 publications

(17 citation statements)

References 5 publications

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“…Successive chromatographic separations of dichloromethane fraction as described in the Experimental section resulted in the isolation of a new polyacetylene (1 C correlations in the HMBC experiment with carbon at d 171.9, confirming the α-β-unsaturated lactone system, as well as with methyne carbon at 79.6 ppm, evidencing a five-member lactone ring. Additionally, methyne hydrogen at 5.14 ppm showed correlations with methylene carbon at 24.5 ppm, which is attached to the lactone ring, as evidenced in the 1 H NMR spectrum.…”

Section: Resultsmentioning

confidence: 90%

“…Many other compounds have also been isolated, such as thiophenes and dithio compounds. 1,2 Among the species of Vernonia, cytotoxicity has been described for isolated sesquiterpene lactones from V. cinerea, 3 V. lasiopus, 4 and V. amygdalina. 5 Besides sesquiterpene lactones, polar compounds from water-soluble extracts of Vernonia have also been found to have cytotoxic and imunomodulatory activities such as those from the edible leaves of V. amygdalina 6 and from the roots of V. kotschyana 7 and V. anthelmintica.…”

Section: Introductionmentioning

confidence: 99%

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A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

Buskuhl¹,

Freitas²,

Monachè³

et al. 2009

J. Braz. Chem. Soc.

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A fração diclorometano obtida pelo particionamento do extrato hidroalcoólico obtido das folhas e flores de Vernonia scorpioides (Asteraceae) resultou no isolamento e caracterização de um novo poliacetileno, 5-octa-2,4,6-triinil-furan-2(5H)-ona. A determinação estrutural foi baseada em dados de espectrometria de Ressonância Magnética Nuclear mono e bidimensionais, de Massas e de Infravermelho. Foi investigado o potencial antitumoral e genotóxico do novo poliacetileno e os resultados encontrados sugerem genotoxicidade e citotoxicidade, onde a morte celular ocorreu via apoptose, envolvendo um mecanismo dependente de caspase.The dichloromethane fraction obtained from hydroalcoholic crude extract of leaves and flowers of Vernonia scorpioides (Asteraceae) was investigated, resulting in the isolation and structure elucidation of a new polyacetylene namely 5-octa-2,4,6-triynyl-furan-2(5H)-one. The structure of the isolated compound was determined based on IR, NMR (1D and 2D) and MS spectrometric data. The antitumor potential, including cytotoxicity to tumor cells and genotoxicity, was investigated. The results suggest that apoptotic cell death may have occurred, at least in part, via a caspasedependent mechanism.Keywords: polyacetylene, Vernonia scorpioides, cytotoxicity, genotoxicity, Asteraceae IntroductionThe widespread genus Vernonia (Asteraceae) is characterized by the fact that it produces highly oxygenated sesquiterpene lactones, such as glaucolides and hirsutinolides, some of which are allenic lactones. Many other compounds have also been isolated, such as thiophenes and dithio compounds.1,2 Among the species of Vernonia, cytotoxicity has been described for isolated sesquiterpene lactones from V. cinerea, 3 V. lasiopus, 4 and V. amygdalina. 5 Besides sesquiterpene lactones, polar compounds from water-soluble extracts of Vernonia have also been found to have cytotoxic and imunomodulatory activities such as those from the edible leaves of V. amygdalina 6 and from the roots of V. kotschyana 7 and V. anthelmintica. 8The species Vernonia scorpioides (Lam.) Pers., which is very common in Brazil, is popularly known as "Piracá", "Enxuga" or "Erva-de-São-Simão" and usually grows in poor deforested neotropical soils.9 Alcoholic extract from the fresh leaves is widely used in topical applications, to treat a variety of skin disorders, including chronic wounds, such as ulcers of the lower limbs. In previous studies, chloroform and hexane crude extracts of V. scorpioides leaves have shown fungicide activity, 10 moderate bactericide activity and mild wound healing effects.11 In addition, in mice treated with dichloromethane extract of the leaves, the Ehrlich tumor disappeared completely.12 Therefore, as part of our ongoing search for bioactive compounds of V. scorpioides, a new polyacetylene isolated from the dichloromethane fraction is described, and its antitumor potential, as well as in vitro cytotoxicity to tumor cells and cell death via genotoxicity, are evaluated. Results and DiscussionThe crude ethanol extract of V. s...

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Section: Resultsmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

Buskuhl¹,

Freitas²,

Monachè³

et al. 2009

J. Braz. Chem. Soc.

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“…Todos os compostos isolados foram descritos previamente para o gênero (Bohlmann & Zdero, 1982;Misra et al, 1984). Estas informações sobre a espécie Vernonia tweediana Baker, conhecida como pertencente a um grupo de plantas de ocorrência marcante na América do Sul, apresentam os primeiros resultados do estudo fi toquímico da fração em diclorometano das folhas da planta.…”

Section: Resultsunclassified

Fitoconstituintes isolados da fração em diclorometano das folhas de Vernonia tweediana Baker

Zanon¹,

Pereira²,

Boschetti³

et al. 2008

Rev. bras. farmacogn.

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RESUMO:Fracionamento cromatográfi co da fração em diclorometano obtida do extrato etanólico das folhas de Vernonia tweediana Baker (Asteraceae) conduziu ao isolamento de α-amirina, β-amirina, lupeol, β-sitosterol, estigmasterol e espinasterol. As estruturas foram identifi cadas através de técnicas espectroscópicas usuais, além da comparação com dados relatados na literatura. Os compostos isolados são relatados pela primeira vez para a espécie V. tweediana. Unitermos:Vernonia tweediana, Asteraceae, triterpenos, esteróides.ABSTRACT: "Phytoconstituents isolated from dichloromethane fraction of Vernonia tweediana Baker leaves". Fractionation of the dichloromethane -soluble fraction from the ethanol extract of the leaves of Vernonia tweediana (Asteraceae) led to the isolation of α-amyrin, β-amyrin, lupeol, β-sitosterol, stigmasterol and spinasterol. The structures of the isolates were elucidated by spectroscopic analysis and comparison with literature data. The isolated compounds are reported for the fi rst time to the species V. tweediana.

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“…De fato, à exceção de saponinas, as substâncias identificadas e isoladas até então das folhas e partes aéreas de Vernonia polyanthes (TABELA 2) são dessas classes majoritárias. Um único estudo descreveu o isolamento de um poliacetileno (BOHLMANN et al, 1981) TABELA 2: Quantitativo de substâncias isoladas e/ou identificadas das folhas e de partes aéreas de Vernonia polyanthes.…”

Section: Resultsunclassified

Vernonia polyanthes (Spreng.) Less.: uma visão geral da sua utilização como planta medicinal, composição química e atividades farmacológicas

et al. 2017

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Allenic germacranolides, bourbonene derived lactones and other constituents from Vernonia species

Cited by 67 publications

References 5 publications

A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

Fitoconstituintes isolados da fração em diclorometano das folhas de Vernonia tweediana Baker

Vernonia polyanthes (Spreng.) Less.: uma visão geral da sua utilização como planta medicinal, composição química e atividades farmacológicas

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