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

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 with TPA as a promoter. Furthermore, upon evaluation of the cytotoxic activities of compounds 1-17 against human cancer cell lines, compounds 2, 5-7, 9, and 14 showed potent activities against HL60 cell line, and compound 2 against SK-BR-3 cell line.
AuthorsJie Zhang, Yan Huang, Takashi Kikuchi, Harukuni Tokuda, Nobutaka Suzuki, Kei-ichiro Inafuku, Motofumi Miura, Shigeyasu Motohashi, Takashi Suzuki, Toshihiro Akihisa
JournalChemistry & biodiversity (Chem Biodivers) Vol. 9 Issue 2 Pg. 428-40 (Feb 2012) ISSN: 1612-1880 [Electronic] Switzerland
PMID22344919 (Publication Type: Journal Article)
CopyrightCopyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.
Chemical References
  • Antigens, Viral
  • Antineoplastic Agents, Phytogenic
  • Carcinogens
  • Epstein-Barr virus early antigen
  • Glycosides
  • Triterpenes
  • cucurbitane
  • 9,10-Dimethyl-1,2-benzanthracene
  • Tetradecanoylphorbol Acetate
Topics
  • 9,10-Dimethyl-1,2-benzanthracene (toxicity)
  • Animals
  • Antigens, Viral (metabolism)
  • Antineoplastic Agents, Phytogenic (isolation & purification, pharmacology)
  • Apoptosis (drug effects)
  • Carcinogens (toxicity)
  • Cell Transformation, Neoplastic (drug effects)
  • Glycosides (isolation & purification, pharmacology)
  • Humans
  • Mice
  • Molecular Structure
  • Momordica charantia (chemistry)
  • Plant Leaves (chemistry)
  • Skin Neoplasms (chemically induced, prevention & control)
  • Tetradecanoylphorbol Acetate (pharmacology)
  • Triterpenes (isolation & purification, pharmacology)
  • Tumor Cells, Cultured

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