title: Novel isoflavone glucosides in groundnut (Apios americana Medik) and their antiandrogenic activities.
abstract: Isoflavone glucosides (2'-hydroxy,5-methoxy genistein-7-O-glucoside (1), 2'-hydroxy genistein-7-O-gentibioside (2), 5-methoxy genistein-7-O-glucoside (3), 3',5-dimethoxy genistein-7-O-glucoside (4), 2'-hydroxy genistein-7-O-glucoside (5), genistein-7-O-gentibioside (6), 2'-hydroxy,5-methoxy genistein-4',7-O-diglucoside (7), and 2'-hydroxy genistein-4',7-O-diglucoside (8)) were isolated from the groundnut of Apios americana Medik. Their structures were elucidated on the basis of HR-ESI-MS and 1D- and 2D-NMR analyses. Compounds 1, 2, 4, and 7 are new compounds presented here for the first time. Compounds 2 and 5 were proven to be androgen receptor antagonists due to their binding activities for androgen receptors (IC50 280 and 160 μM, respectively) and the inhibitory activity of androgen-induced expression of prostate-specific antigen (PSA) mRNA in LNCaP (prostate adenocarcinoma) cells (IC50 20 and 18 μM, respectively).
authors: Department of Food and Nutrition, Japan Women's University , 2-8-1, Mejirodai, Bunkyo-ku, Tokyo 112-8681, Japan.
authors: Marina
authors: M
authors: Ichige
authors: Erina
authors: E
authors: Fukuda
authors: Saki
authors: S
authors: Miida
authors: Jun-ichiro
authors: J
authors: Hattan
authors: Norihiko
authors: N
authors: Misawa
authors: Shun
authors: S
authors: Saito
authors: Takahiro
authors: T
authors: Fujimaki
authors: Masaya
authors: M
authors: Imoto
authors: Kazutoshi
authors: K
authors: Shindo
mesh_terms: D000726:Androgen Antagonists / Q000737:chemistry / Q000494:pharmacology*; D059002:Androgen Receptor Antagonists; D010367:Arachis / Q000737:chemistry*; D045744:Cell Line, Tumor; D015870:Gene Expression / Q000187:drug effects; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D017430:Prostate-Specific Antigen / Q000235:genetics; D011471:Prostatic Neoplasms / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000726:Androgen Antagonists; D059002:Androgen Receptor Antagonists; D005960:Glucosides; D007529:Isoflavones; D017430:Prostate-Specific Antigen