Publication: Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. requires metabolic activation
Issued Date
2009-02-11
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ISSN
00218561
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2-s2.0-61449169095
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Agricultural and Food Chemistry. Vol.57, No.3 (2009), 840-845
Suggested Citation
Wipawee Winuthayanon, Kanoknetr Suksen, Chuenchit Boonchird, Aporn Chuncharunee, Mathurose Ponglikitmongkol, Apichart Suksamrarn, Pawinee Piyachaturawat Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. requires metabolic activation. Journal of Agricultural and Food Chemistry. Vol.57, No.3 (2009), 840-845. doi:10.1021/jf802702c Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27054
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Title
Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. requires metabolic activation
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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 α, coactivator TIF2 and a β-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 17β-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. © 2009 American Chemical Society.