Anti-tumor promoting effects of multiflorane-type triterpenoids and cytotoxic activity of karounidiol against human cancer cell lines

被引:53
作者
Akihisa, T
Tokuda, H
Ichiishi, E
Mukainaka, T
Toriumi, M
Ukiya, M
Yasukawa, K
Nishino, H
机构
[1] Nihon Univ, Coll Sci & Technol, Chiyoda Ku, Tokyo 1018308, Japan
[2] Kyoto Prefectural Univ Med, Dept Biochem, Kamigyo Ku, Kyoto 6020841, Japan
[3] Nihon Univ, Coll Pharm, Funabashi, Chiba 2748555, Japan
关键词
Trichosanthes kirilowii; Cucurbitaceae; anti-tumor promoter; Epstein-Barr virus early antigens; multiflorane-type triterpenoids; structure-activity relationships; cytotoxicity;
D O I
10.1016/S0304-3835(01)00689-9
中图分类号
R73 [肿瘤学];
学科分类号
100214 ;
摘要
Forty-nine multiflorane-type triterpenoids consisting of 11 compounds isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae) and 38 of their derivatives have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate in Raji cells as a primary screening test for anti-tumor promoters. All of the compounds tested showed an inhibitory effect against EBV-EA activation, and among which 43 were revealed to possess remarkable activity with potencies either comparable to or stronger than that of glycyrrhetic acid, a known natural anti-tumor promoter. Their structure-activity relationship is discussed. Evaluation of the cytotoxic activity of karounidiol (27) against human cancer cell lines exhibited cytotoxicity especially against a human renal cancer. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.
引用
收藏
页码:9 / 14
页数:6
相关论文
共 13 条
[1]   7-oxodihydrokarounidiol-3-benzoate and other triterpenes from the seeds of cucurbitaceae [J].
Akihisa, T ;
Kimura, Y ;
Kasahara, Y ;
Kumaki, K ;
Thakur, S ;
Tamura, T .
PHYTOCHEMISTRY, 1997, 46 (07) :1261-1266
[2]   KAROUNIDIOL [D-C-FRIEDO-OLEANA-7,9(11)-DIENE-3-ALPHA,29-DIOL] AND ITS 3-O-BENZOATE - NOVEL PENTACYCLIC TRITERPENES FROM TRICHOSANTHES-KIRILOWII - X-RAY MOLECULAR-STRUCTURE OF KAROUNIDIOL DIACETATE [J].
AKIHISA, T ;
TAMURA, T ;
MATSUMOTO, T ;
EGGLESTON, DS ;
KOKKE, WCMC ;
SHIMIZU, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :439-443
[3]  
AKIHISA T, 1992, CHEM PHARM BULL, V40, P1199, DOI 10.1248/cpb.40.1199
[4]  
AKIHISA T, 1994, CHEM PHARM BULL, V42, P1101, DOI 10.1248/cpb.42.1101
[5]   ISOKAROUNIDIOL [D-C-FRIEDOOLEANA-6,8-DIENE-3-ALPHA,29-DIOL] - THE 1ST NATURALLY-OCCURRING TRITERPENE WITH A DELTA-6,8-CONJUGATED DIENE SYSTEM - IODINE-MEDIATED DEHYDROGENATION AND ISOMERIZATION OF ITS DIACETATE [J].
AKIHISA, T ;
KOKKE, WCMC ;
KIMURA, Y ;
TAMURA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1959-1962
[6]   5-DEHYDROKAROUNIDIOL [D-C-FRIEDO-OLEANA-5,7,9(11)-TRIENE-3-ALPHA,29-DIOL], A NOVEL TRITERPENE FROM TRICHOSANTHES-KIRILOWII MAXIM [J].
AKIHISA, T ;
KOKKE, WCMC ;
KRAUSE, JA ;
EGGLESTON, DS ;
KATAYAMA, S ;
KIMURA, Y ;
TAMURA, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (12) :3280-3283
[7]   SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN [J].
BOYD, MR ;
PAULI, KD .
DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) :91-109
[8]   TRITERPENE ALCOHOLS IN THE SEEDS OF 2 CUCUMIS SPECIES OF CUCURBITACEAE [J].
ITOH, T ;
SHIGEMOTO, T ;
SHIMIZU, N ;
TAMURA, T ;
MATSUMOTO, T .
PHYTOCHEMISTRY, 1982, 21 (09) :2414-2415
[9]  
Konoshima T, 1996, BIOL PHARM BULL, V19, P962, DOI 10.1248/bpb.19.962
[10]  
NAMBA T, 1994, ENCY WAKAN YAKU COLO, V1, P217