Evaluation of triterpene glycoside estrogenic activity using LC/MS and immunoaffinity extraction.
We present a study on the mass spectral as well as the binding properties of three triterpene glycosides (cimicifugoside, cimiracemoside F, 27-deoxyactein) contained in black cohosh to the ligand binding domain of estrogen receptor beta (ER-beta). Using affinity ultrafiltration and LC/ MS detection, initial experiments using estradiol and the phytoestrogens daidzein and genistein (compounds known to bind ER-beta) were performed to serve as positive controls. The same affinity techniques and LC/MS procedures were then employed to show that neither the triterpene glycosides nor their enzymatically prepared aglycons bound significantly to ER-beta, except for 27-deoxyactein aglycon, which showed weak binding affinity (4%). Additionally, metabolites of the aglycons were prepared by incubation with female human liver microsomes and subjected to binding experiments with ER-beta. No significant binding of the metabolites to the receptor was observed. Further studies are needed to fully characterize whether these triterpene glycosides as well as other components of black cohosh in this plant extract bind to the estrogen receptor alpha (ER-alpha).
Onorato
J
J
Analytical Toxicology, Cornell University, Ithaca, New York 14850, USA.
Henion
J D
JD
D002623:Chemistry Techniques, Analytical / Q000379:methods; D002853:Chromatography, Liquid / Q000379:methods; D047629:Estrogen Receptor beta; D004968:Estrogens, Non-Steroidal / Q000032:analysis / Q000378:metabolism* / Q000494:pharmacology; D005260:Female; D006027:Glycosides / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D007529:Isoflavones; D007700:Kinetics; D013058:Mass Spectrometry / Q000379:methods; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen / Q000378:metabolism*; D014315:Triterpenes / Q000032:analysis / Q000378:metabolism* / Q000494:pharmacology
D047629:Estrogen Receptor beta; D004968:Estrogens, Non-Steroidal; D006027:Glycosides; D007529:Isoflavones; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen; D014315:Triterpenes