Journal
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
Volume 401, Issue 1, Pages 305-313Publisher
SPRINGER HEIDELBERG
DOI: 10.1007/s00216-011-5061-9
Keywords
Prenylation; Isoflavonoids; Licorice; Estrogenicity; Antagonism; Superinduction
Funding
- Food and Nutrition Delta of the Ministry of Economic Affairs, The Netherlands
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The roots of licorice (Glycyrrhiza glabra) are a rich source of flavonoids, in particular, prenylated flavonoids, such as the isoflavan glabridin and the isoflavene glabrene. Fractionation of an ethyl acetate extract from licorice root by centrifugal partitioning chromatography yielded 51 fractions, which were characterized by liquid chromatography-mass spectrometry and screened for activity in yeast estrogen bioassays. One third of the fractions displayed estrogenic activity towards either one or both estrogen receptors (ERs; ER alpha and ER beta). Glabrene-rich fractions displayed an estrogenic response, predominantly to the ER alpha. Surprisingly, glabridin did not exert agonistic activity to both ER subtypes. Several fractions displayed higher responses than the maximum response obtained with the reference compound, the natural hormone 17 beta-estradiol (E(2)). The estrogenic activities of all fractions, including this so-called superinduction, were clearly ER-mediated, as the estrogenic response was inhibited by 20-60% by known ER antagonists, and no activity was found in yeast cells that did not express the ER alpha or ER beta subtype. Prolonged exposure of the yeast to the estrogenic fractions that showed superinduction did, contrary to E(2), not result in a decrease of the fluorescent response. Therefore, the superinduction was most likely the result of stabilization of the ER, yeast-enhanced green fluorescent protein, or a combination of both. Most fractions displaying superinduction were rich in flavonoids with single prenylation. Glabridin displayed ER alpha-selective antagonism, similar to the ER alpha-selective antagonist RU 58668. Whereas glabridin was able to reduce the estrogenic response of E(2) by approximately 80% at 6 x 10(-6) M, glabrene-rich fractions only exhibited agonistic responses, preferentially on ER alpha.
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