Sesquiterpenes from Cyperus rotundus and 4α,5α-oxidoeudesm-11-en-3-one as a potential selective estrogen receptor modulator - 09/12/18
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Graphical abstract |
Highlights |
• | 4α,5α-oxidoeudesm-11-en-3-one newly isolated from natural resources. |
• | 4α,5α-oxidoeudesm-11-en-3-one exhibited potent estrogenic activity. |
• | 4α,5α-oxidoeudesm-11-en-3-one showed higher binding affinity to ER-β than ER-α. |
• | 4α,5α-oxidoeudesm-11-en-3-one showed both estrogenic and antiestrogenic effects depending on the E2 concentration. |
Abstract |
Estrogenic activity-oriented fractionation and purification of methanol extract from the rhizome of Cyperus rotundus, a well-known traditional herbal medicine, led to the isolation of six sesquiterpenes. 4α,5α-Oxidoeudesm-11-en-3-one (2) and cyper-11-ene-3,4-dione (3) together with four known sesquiterpenes, cyperotundone (1), caryophyllene α-oxide (4), α-cyperone (5), and isocyperol (6) were obtained from the hexane and dichloromethane fractions. Compounds 2 and 3 were newly isolated from natural resources in particular. To identify the possible use of isolated compounds as an alternative to hormone replacement therapy (HRT), estrogenic activity was evaluated by E-screen assay on MCF-7 BUS cells. Among the all isolated compounds from the rhizome of Cyperus rotundus, newly isolated from natural resource, 2 exhibited the most potent estrogenic activity. In an estrogen sensitive reporter gene assay, 2 significantly increased transcriptional activities. As a phytoestrogen, 2 was assessed by investigating dual action on ER-α and ER-β in competitive binding assay. It was found that 2 exerted higher binding affinity to ER-β than ER-α and it also showed both estrogenic and antiestrogenic effects depending on the E2 concentration. Our results indicate that newly isolated from Cyperus rotundus, 2 has biphasic activities on estrogen receptors which could be useful as an alternative HRT.
Le texte complet de cet article est disponible en PDF.Keywords : Cyperus rotundus, Sesquiterpenes, 4α,5α-oxidoeudesm-11-en-3-one, Estrogen, Hormone replacement therapy
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Vol 109
P. 1313-1318 - janvier 2019 Retour au numéroBienvenue sur EM-consulte, la référence des professionnels de santé.
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