Antitumor-promoting effects and cytotoxic activities of dammar resin triterpenoids and their derivatives.
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| Abstract |
Nineteen known triterpenoids, 1-19, and one known sesquiterpenoid, 20, were isolated from dammar resin obtained from Shorea javanica K. & V. (Dipterocarpaceae). One of the acidic triterpenoids, dammarenolic acid (1), was converted to fourteen derivatives, namely, an alcohol, 21, an aldehyde, 22, and twelve L-amino acid conjugates, 23-34. Compounds 1-34 were examined 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, a known primary screening test for antitumor promoters. All of the compounds tested, except for compounds 4, 5, 12-14, 16, and 17, showed inhibitory effects against EBV-EA activation with potencies either comparable with or stronger than that of beta-carotene, a known natural antitumor promoter. In addition, (20S)-20-hydroxy-3,4-secodammara-4(28),24-dien-3-al (22) 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 promoter. Furthermore, evaluation of the cytotoxic activities of compounds 1-34 against human cancer cell lines showed that reduction (i.e., 21 and 22) or conjugation with L-amino acids (i.e., 23-34) of compound 1 enhanced the cytotoxicity against human melanoma cell line CRL1579.
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| Authors | Motohiko Ukiya, Takashi Kikuchi, Harukuni Tokuda, Keiichi Tabata, Yumiko Kimura, Takanari Arai, Yoichiro Ezaki, Osamu Oseto, Takashi Suzuki, Toshihiro Akihisa |
| Journal | Chemistry & biodiversity (Chem Biodivers) Vol. 7 Issue 8 Pg. 1871-84 (Aug 2010) ISSN: 1612-1880 [Electronic] Switzerland |
| PMID | 20730953 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't) |
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