Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities

Marina Ichige, Erina Fukuda, Saki Miida, Jun Ichiro Hattan, Norihiko Misawa, Shun Saito, Takahiro Fujimaki, Masaya Imoto, Kazutoshi Shindo

Research output: Contribution to journalArticle

20 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)2183-2187
Number of pages5
JournalJournal of Agricultural and Food Chemistry
Volume61
Issue number9
DOIs
Publication statusPublished - 2013 Mar 6

Fingerprint

Apios americana
genistin
Isoflavones
genistein
Glucosides
isoflavones
glucosides
peanuts
Genistein
Inhibitory Concentration 50
inhibitory concentration 50
Androgen Receptor Antagonists
prostate-specific antigen
Androgen Receptors
Prostate-Specific Antigen
androgens
adenocarcinoma
Androgens
Prostate
antagonists

Keywords

  • antiandrogenic activity
  • Apios americana Medik
  • isoflavone glucosides
  • LNCaP human prostate adenocarcinoma cells

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

Cite this

Ichige, M., Fukuda, E., Miida, S., Hattan, J. I., Misawa, N., Saito, S., ... Shindo, K. (2013). Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities. Journal of Agricultural and Food Chemistry, 61(9), 2183-2187. https://doi.org/10.1021/jf305233t

Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities. / Ichige, Marina; Fukuda, Erina; Miida, Saki; Hattan, Jun Ichiro; Misawa, Norihiko; Saito, Shun; Fujimaki, Takahiro; Imoto, Masaya; Shindo, Kazutoshi.

In: Journal of Agricultural and Food Chemistry, Vol. 61, No. 9, 06.03.2013, p. 2183-2187.

Research output: Contribution to journalArticle

Ichige, M, Fukuda, E, Miida, S, Hattan, JI, Misawa, N, Saito, S, Fujimaki, T, Imoto, M & Shindo, K 2013, 'Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities', Journal of Agricultural and Food Chemistry, vol. 61, no. 9, pp. 2183-2187. https://doi.org/10.1021/jf305233t
Ichige, Marina ; Fukuda, Erina ; Miida, Saki ; Hattan, Jun Ichiro ; Misawa, Norihiko ; Saito, Shun ; Fujimaki, Takahiro ; Imoto, Masaya ; Shindo, Kazutoshi. / Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities. In: Journal of Agricultural and Food Chemistry. 2013 ; Vol. 61, No. 9. pp. 2183-2187.
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