Synthesis of the furanoheliangolide ring skeleton

McDougal, Patrick G.; Oh, Young Im; VanDerveer, Don

doi:10.1021/jo00262a024

Cited by 37 publications

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“…This might be com pared to the proposed mechanism for the antitumor activity of the eremantholides by reaction with biological nucleophiles (Mc Dougal et al 1989). …”

Section: Resultsmentioning

confidence: 62%

Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

Saúde-Guimarães

Raslan

Chiari

et al. 2014

An. Acad. Bras. Ciênc.

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Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1',2'-epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1',2'-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1',2'-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, 1 H and 13 C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain.

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“…This might be com pared to the proposed mechanism for the antitumor activity of the eremantholides by reaction with biological nucleophiles (Mc Dougal et al 1989). …”

Section: Resultsmentioning

confidence: 62%

Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

Saúde-Guimarães

Raslan

Chiari

et al. 2014

An. Acad. Bras. Ciênc.

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“…Compound 1 besides to possess an α-methylene-γ-lactone unity, to present others two α,β-unsaturated carbonyl groups. Nevertheless, the eremantholides were less cytotoxic (Mc Dougal et al, 1989).…”

Section: Resultsmentioning

confidence: 94%

“…In the case of eremantholides, the eletrophilic center, that would be responsible for its antitumor activity, is the carbon five (Mc Dougal et al, 1989). Covalent binding of sesquiterpene lactones to free sulfydryl groups in proteins may interfere with the functions of these macromolecules.…”

Section: Resultsmentioning

confidence: 99%

In Vitro Antitumor Activity of Sesquiterpene Lactones from Lychnophora trichocarpha

Saúde-Guimarães

Raslan

Oliveira

2014

Rev. bras. plantas med.

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ABSTRACT:The sesquiterpene lactones lychnopholide and eremantholide C were isolated from Lychnophora trichocarpha Spreng. (Asteraceae), which is a plant species native to the Brazilian Savannah or Cerrado and popularly known as arnica. Sesquiterpene lactones are known to present a variety of biological activities including antitumor activity. The present paper reports on the evaluation of the in vitro antitumor activity of lychnopholide and eremantholide C, in the National Cancer Institute, USA (NCI, USA), against a panel of 52 human tumor cell lines of major human tumors derived from nine cancer types. Lychnopholide disclosed significant activity against 30 cell lines of seven cancer types with IC 100 (total growth concentration inhibition) values between 0.41 µM and 2.82 µM. Eremantholide C showed significant activity against 30 cell lines of eight cancer types with IC 100 values between 21.40 µM and 53.70 µM. Lychnopholide showed values of lethal concentration 50 % (LC 50 ) for 30 human tumor cell lines between 0.72 and 10.00 µM, whereas eremantholide C presented values of LC 50 for 21 human tumor cell lines between 52.50 and 91.20 µM. Lychnopholide showed an interesting profile of antitumor activity. The α-methylene-γ-lactone present in the structure of lychnopholide, besides two α,β-unsaturated carbonyl groups, might be responsible for the better activity and higher cytotoxicity of this compound in relation to eremantholide C. Keywords:Lychnopholide, eremantholide C, sesquiterpene lactones, Lychnophora trichocarpha, antitumor.RESUMO: Atividade antitumoral in vitro de lactonas sesquiterpenicas de Lychnophora. As lactonas sesquiterpênicas licnofolida e eremantolida C foram isoladas de Lychnophora trichocarpha Spreng. (Asteraceae), espécie vegetal nativa do cerrado brasileiro e popularmente conhecida por arnica brasileira. As lactonas sesquiterpênicas são conhecidas por apresentarem variadas atividades biológicas, incluindo atividade antitumoral. O presente artigo relata a avaliação da atividade antitumoral in vitro de licnofolida e eremantolida C frente a um painel de 52 linhagens de células tumorais, provenientes de tumores humanos referentes a nove principais tipos de câncer. Os testes foram conduzidos no National Cancer Institute, USA (NCI, USA). Licnofolida apresentou atividade significativa frente a 30 linhagens de células tumorais referentes a sete tipos de câncer, com valores de CI 100 (concentração que inibe 100% do crescimento celular) entre 0,41 µM e 2,82 µM. Eremantolida C mostrou atividade significativa frente a 30 linhagens de células tumorais referentes a oito tipos de câncer, com valores de CI 100 entre 21,40 µM e 53,70 µM. Licnofolida apresentou valores de concentração letal 50 % (CL 50 ) para 30 linhagens de células tumorais humanas entre 0,72 e 10,00 µM, enquanto eremantolida C mostrou valores de CL 50 para 21 linhagens entre 52,50 e 91,20 µM. Licnofolida apresentou um interessante perfil de atividade antitumoral. A presença na estrutura química da licnofolida de uma α-metileno-γ-lactona, al...

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“…40 In addition, 1,3-dienyl sulfides play a very important role in Diels-Alder reactions, where they impart an added level of reactivity and regioselectivity to such cycloadditions. [41][42][43][44] Due to their synthetic utility, a variety of methods have been developed for their preparation. [45][46][47][48][49] However, the stereoselective synthesis of polysubstituted 1,3-dienyl sulfides has received less attention.…”

mentioning

confidence: 99%

A facile stereoselective synthesis of 1,3-dienyl and 1,4-dienyl sulfides by hydrostannylation-Stille tandem reaction of acetylenic sulfides

Yao

Hao

Cai

2009

Journal of Chemical Research

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Synthesis of the furanoheliangolide ring skeleton

Cited by 37 publications

References 0 publications

Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

In Vitro Antitumor Activity of Sesquiterpene Lactones from Lychnophora trichocarpha

A facile stereoselective synthesis of 1,3-dienyl and 1,4-dienyl sulfides by hydrostannylation-Stille tandem reaction of acetylenic sulfides

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