Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects.
Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1-5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC(50) values of 200-409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1-5 for inhibitory effects against activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1-3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.
College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
Toshihiro
T
Akihisa
Naoki
N
Higo
Harukuni
H
Tokuda
Motohiko
M
Ukiya
Hiroyuki
H
Akazawa
Yuichi
Y
Tochigi
Yumiko
Y
Kimura
Takashi
T
Suzuki
Hoyoku
H
Nishino
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000494:pharmacology; D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification / Q000494:pharmacology; D000956:Antigens, Viral / Q000187:drug effects; D005638:Fruit / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D029777:Momordica charantia / Q000737:chemistry*; D020030:Nitric Oxide Donors / Q000494:pharmacology; D030421:Peroxynitrous Acid / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D012878:Skin Neoplasms / Q000139:chemically induced; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification / Q000494:pharmacology
D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; C033305:Epstein-Barr virus early antigen; D006027:Glycosides; D020030:Nitric Oxide Donors; D014315:Triterpenes; D030421:Peroxynitrous Acid; D015127:9,10-Dimethyl-1,2-benzanthracene; D013755:Tetradecanoylphorbol Acetate