Bioactive taxoids from Japanese yew Taxus cuspidata and taxol biosynthesis

被引:48
作者
Kobayashi, J [1 ]
Shigemori, H [1 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 060, Japan
关键词
D O I
10.3987/REV-97-SR(N)7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of new taxoids, named taxuspines A similar to H and J similar to Z (1 similar to 25), have been isolated together with 37 known taxoids (26 similar to 62) including taxol (42) from the Japanese yew Taxus cuspidata Sieb. ct Zucc. These new taxoids possessed various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, or 6/12-membered ring systems. Among the new taxoids, some non-taxol-type compounds remarkably reduced CaCl2-induced depolymerization of microtubules, or increased cellular accumulation of vincristine in multidrug-resistant tumor cells as potent as verapamil. Here we describe our recent results on the isolation, structure elucidation, and bioactivity of these new and known taxoids as well as recent development of taxol biosynthesis.
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收藏
页码:1111 / 1133
页数:23
相关论文
共 44 条
[1]   REVISED STRUCTURE OF BREVIFOLIOL AND SOME BACCATIN-VI DERIVATIVES [J].
APPENDINO, G ;
BARBONI, L ;
GARIBOLDI, P ;
BOMBARDELLI, E ;
GABETTA, B ;
VITERBO, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (20) :1587-1589
[2]   THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .10. REARRANGED TAXANES FROM TAXUS-BACCATA [J].
APPENDINO, G ;
CRAVOTTO, G ;
ENRIU, R ;
JAKUPOVIC, J ;
GARIBOLDI, P ;
GABETTA, B ;
BOMBARDELLI, E .
PHYTOCHEMISTRY, 1994, 36 (02) :407-411
[3]   THE PHYTOCHEMISTRY OF THE YEW TREE [J].
APPENDINO, G .
NATURAL PRODUCT REPORTS, 1995, 12 (04) :349-360
[4]  
BOLLAG DM, 1995, CANCER RES, V55, P2325
[5]   STRUCTURES OF 4 NEW TAXININE CONGENERS AND A PHOTOCHEMICAL TRANSANNULAR REACTION [J].
CHIANG, HC ;
WOODS, MC ;
NAKADAIRA, Y ;
NAKANISHI, K .
CHEMICAL COMMUNICATIONS, 1967, (23) :1201-+
[6]  
DEMARCANO DPD, 1970, J CHEM SOC CHEM COMM, P1382
[7]   Studies on the biosynthesis of taxol: The taxane carbon skeleton is not of mevalonoid origin [J].
Eisenreich, W ;
Menhard, B ;
Hylands, PJ ;
Zenk, MH ;
Bacher, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (13) :6431-6436
[8]   THE BIOCHEMISTRY OF P-GLYCOPROTEIN-MEDIATED MULTIDRUG RESISTANCE [J].
ENDICOTT, JA ;
LING, V .
ANNUAL REVIEW OF BIOCHEMISTRY, 1989, 58 :137-171
[9]   BIOSYNTHESIS OF TAXOIDS - MODE OF FORMATION OF THE TAXOL SIDE-CHAIN [J].
FLEMING, PE ;
MOCEK, U ;
FLOSS, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :805-807
[10]  
GAMINI S, 1993, J NAT PRODUCTS, V56, P884