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.

In Vitro and In Vivo Effects of Xanthorrhizol on Human Breast Cancer MCF-7 Cells Treated With Tamoxifen

“…Curcuma xanthorrhiza Roxb., an indigenous herb of Southeast Asia countries, is commonly used to bring about uterus tightening (13), particularly in pregnant women after childbirth or when patients suffer from postpartum uterine swelling (14). Xanthorrhizol, a sesquiterpene compound isolated from Curcuma xanthorrhiza Roxb., has been reported to possess not only anticandidal, antibacterial, antimetastatic, and anti-inflammatory activity (15 -17).…”

A Natural Remedy that Reduces Symptoms of Menopause

“…These carefully chosen herbs contain phytoestrogens and other compounds that have beneficial therapeutic potentials in maintaining women's fertility [3][4][5][6] and reducing menopause systems as well as adjusting other factors such as those related to psychological reasons and stress [7][8][9][10][11]. It showed distinctive effectiveness as observed by clinicians who used it on many cases of women aged between 40-60 years during …”

“…While not regulated by the FDA, herbal dietary supplements are among the most common complementary treatments for menopause. Menopause 6 has been clinically shown to reduce and adjust menopausal symptoms by regulating female sex hormones [3][4][5][6], balancing the levels of these two hormones that may be due to dysfunctional immune system [7][8][9][10] certain allergies, autoimmune thyroid disorder and antibodies to hormone production and other factors such as psychological disorders and stress. As a result, Menopause 6 is a promising new therapy for women struggling with hot flashes, mood swings, or other symptoms of menopause (Figure 1).…”

Determination of the Marker Diarylheptanoid Phytoestrogens in <i>Curcuma comosa</i> Rhizomes and Selected Herbal Medicinal Products by HPLC-DAD

“…[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Pure compounds and plant extracts of C. comosa exhibited several pharmacological activities including anti-allergic, 9) anti-inflammatory, 13) anti-melanogenesis, 8) hepatoprotective, 16) bonesparing 17) and estrogenic effects. 20) Among these pharmacological activities, the estrogen-like property of the C. comosa has evoked public interest and led to research studies for its application as a hormone replacement therapy instead of estrogen treatment.…”

“…21) Compound 2 was identified as the most potent phytoestrogenic agent. [18][19][20] In recombinant yeast system, the relative potency of estrogenic activity of 2 and 3 showed 4 and 1% respectively compared to 17β-estradiol. 5) Our unpublished in silico-study also found that all compounds exhibited affinity to estrogen receptors and that supported the findings of previous studies in estrogen-like activity of 2 and 3.…”