TY - JOUR
T1 - Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities
AU - Ichige, Marina
AU - Fukuda, Erina
AU - Miida, Saki
AU - Hattan, Jun Ichiro
AU - Misawa, Norihiko
AU - Saito, Shun
AU - Fujimaki, Takahiro
AU - Imoto, Masaya
AU - Shindo, Kazutoshi
PY - 2013/3/6
Y1 - 2013/3/6
N2 - 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).
AB - 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).
KW - Apios americana Medik
KW - LNCaP human prostate adenocarcinoma cells
KW - antiandrogenic activity
KW - isoflavone glucosides
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U2 - 10.1021/jf305233t
DO - 10.1021/jf305233t
M3 - Article
C2 - 23402539
AN - SCOPUS:84874848683
SN - 0021-8561
VL - 61
SP - 2183
EP - 2187
JO - Journal of agricultural and food chemistry
JF - Journal of agricultural and food chemistry
IS - 9
ER -