title: Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. Requires metabolic activation.
abstract: Curcuma comosa Roxb. has traditionally been used as a dietary supplement for health promotion in peri- and postmenopausal women in Thailand. We investigated the estrogenic activity of 7 naturally occurring diarylheptanoids from the extracts of C. comosa both in vitro and in vivo. A yeast recombinant system containing human estrogen receptor alpha, coactivator TIF2 and a beta-galactosidase reporter gene was used to determine estrogenic activity of diarylheptanoids metabolically activated with rat liver S9-fraction prior to the assay. The most potent compound was (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol, with a relative potency of 4% compared to 17beta-estradiol. The metabolic activation of diarylheptanoids markedly enhanced their efficiency. The chemical structure required for estrogenic activity of diarylheptanoids was the presence of a keto group at C3 and absence of hydroxyl moiety in ring B. Only diarylheptanoids showing full estrogenic efficiency in vitro were able to elicit uterotrophic activity of in immature ovariectomized rat. This is the first evidence for in vivo estrogenic activity of diarylheptanoids from C. comosa. This novel class of natural phytoestrogens has the potential to be developed for use as dietary supplement in the treatment of menopausal symptoms.
authors.affiliation: Department of Physiology, Faculty of Science, Mahidol University, Bangkok, Thailand.
authors.forename: Wipawee
authors.initials: W
authors.lastname: Winuthayanon
authors.forename: Kanoknetr
authors.initials: K
authors.lastname: Suksen
authors.forename: Chuenchit
authors.initials: C
authors.lastname: Boonchird
authors.forename: Aporn
authors.initials: A
authors.lastname: Chuncharunee
authors.forename: Mathurose
authors.initials: M
authors.lastname: Ponglikitmongkol
authors.forename: Apichart
authors.initials: A
authors.lastname: Suksamrarn
authors.forename: Pawinee
authors.initials: P
authors.lastname: Piyachaturawat
mesh_terms: D000818:Animals; D030024:Curcuma / Q000737:chemistry*; D036381:Diarylheptanoids / Q000737:chemistry / Q000494:pharmacology*; D004958:Estradiol / Q000494:pharmacology; D047628:Estrogen Receptor alpha / Q000187:drug effects / Q000235:genetics; D005260:Female; D006801:Humans; D009929:Organ Size / Q000187:drug effects; D010052:Ovariectomy; D048789:Phytoestrogens / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry*; D051381:Rats; D017208:Rats, Wistar; D012441:Saccharomyces cerevisiae / Q000235:genetics; D014599:Uterus / Q000187:drug effects / Q000254:growth & development
chemical_list: D036381:Diarylheptanoids; D047628:Estrogen Receptor alpha; D048789:Phytoestrogens; D010936:Plant Extracts; D004958:Estradiol