Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities

Chemistry & Biodiversity
Jie ZhangToshihiro Akihisa

Abstract

Seventeen cucurbitane-type triterpenoids, 1-17, including six new compounds, (23E)-3β,25-dihydroxy-7β-methoxycucurbita-5,23-dien-19-al (1), (23S*)-3β-hydroxy-7β,23-dimethoxycucurbita-5,24-dien-19-al (6), (23R*)-23-O-methylmomordicine IV (7), (25ξ)-26-hydroxymomordicoside L (8), 25-oxo-27-normomordicoside L (9), and 25-O-methylkaravilagenin D (12), were isolated from a MeOH extract of the leaves of Japanese Momordica charantia. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Compounds 1-17 were examined for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, a known primary screening test for inhibitors of tumor promotion. Four compounds, 1, (23E)-3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al (2), karavilagenin D (11), and 12, showed potent inhibitory effects on EBV-EA induction with IC(50) values in the range of 242-264 mol ratio/32 pmol TPA. In addition, compounds 1 and 11 exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and ...Continue Reading

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Citations

Apr 9, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tzung-Hsun TsaiPo-Jung Tsai
May 7, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Jutamas SaengsaiWeena Jiratchariyakul
Mar 13, 2016·Chinese Journal of Natural Medicines·Prasad R DandawateShrikant Anant
Oct 25, 2014·Natural Product Reports·Robert A Hill, Joseph D Connolly
Jul 12, 2012·Chemistry & Biodiversity·Takashi KikuchiToshihiro Akihisa
Jun 12, 2018·Journal of the Science of Food and Agriculture·Jose L PerezBhimanagouda S Patil
Aug 14, 2013·Chemistry & Biodiversity·Aranya ManosroiToshihiro Akihisa

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