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1.
Bioorg Med Chem ; 16(14): 6891-902, 2008 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-18554915

RESUMO

Three new diarylheptanoids, a 1:2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene (9) and 1-(4-hydroxyphenyl)-7-phenyl-(4E,6E)-4,6-heptadien-3-one (16), and nine known diarylheptanoids, 2, 8, 10-12, 14, a 3:1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ERbeta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an olefinic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1-position of the heptyl chain.


Assuntos
Curcuma/química , Diarileptanoides/farmacologia , Fitoestrógenos/farmacologia , Rizoma/química , Diarileptanoides/isolamento & purificação , Receptor beta de Estrogênio/genética , Estrogênios/química , Estrogênios/farmacologia , Células HeLa , Humanos , Fitoestrógenos/isolamento & purificação , Reação em Cadeia da Polimerase Via Transcriptase Reversa , Relação Estrutura-Atividade , Transcrição Gênica/efeitos dos fármacos , Proteína bcl-X/genética
2.
J Nat Prod ; 65(8): 1194-7, 2002 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-12193031

RESUMO

A new ecdysteroid, zoanthusterone, has been isolated from a marine zoanthid, Zoanthus sp. Ten known ecdysteroids, ponasterone A, 20-hydroxyecdysone 2-acetate, viticosterone E, integristerone A 25-acetate, 2-deoxy-20-hydroxyecdysone, ecdysone, ajugasterone C, dacryhainansterone, inokosterone, and 20-hydroxyecdysone, have also been isolated. This is the first report of ecdysteroids in a Zoanthus species.


Assuntos
Cnidários/química , Ecdisteroides/química , Ecdisteroides/isolamento & purificação , Ecdisterona/análogos & derivados , Ecdisterona/isolamento & purificação , Animais , Colestenos/química , Colestenos/isolamento & purificação , Cromatografia em Camada Fina , Ecdisona/química , Ecdisona/isolamento & purificação , Ecdisterona/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Tailândia
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