ANTITUMOR AGENTS .135. STRUCTURE AND STEREOCHEMISTRY OF POLACANDRIN, A NEW CYTOTOXIC TRITERPENE FROM POLANISIA-DODECANDRA

被引:19
作者
SHI, Q
CHEN, K
FUJIOKA, T
KASHIWADA, Y
CHANG, JJ
KOZUKA, M
ESTES, JR
MCPHAIL, AT
MCPHAIL, DR
LEE, KH
机构
[1] UNIV N CAROLINA,SCH PHARM,DIV MED CHEM & NAT PROD,NAT PROD LAB,CHAPEL HILL,NC 27599
[2] UNIV N CAROLINA,SCH MED,ANIM MED LAB,CHAPEL HILL,NC 27599
[3] KYOTO PHARMACEUT UNIV,KYOTO 607,JAPAN
[4] UNIV OKLAHOMA,DEPT BOT,NORMAN,OK 73019
[5] DUKE UNIV,PAUL M GROSS CHEM LAB,DEPT CHEM,DURHAM,NC 27706
来源
JOURNAL OF NATURAL PRODUCTS | 1992年 / 55卷 / 10期
关键词
D O I
10.1021/np50088a015
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new dammarane triterpene, polacandrin [1], has been isolated from Polanisia dodecandra. The structure of 1 was established as 1beta,3alpha,12beta,25-tetrahydroxy-20(S),24(S)-epoxydammarane chemical and spectroscopic methods, which included the concerted application of a number of 2D nmr techniques that involved H-1-H-1 COSY, HETCOR, NOESY, and long-range HETCOR. Single-crystal X-my analysis of polacandrin pentahydrate verified the complete structure and stereochemistry. Polacandrin showed potent cytotoxicities against KB (ED50 = 0.60 mug/ml), P-388 (ED50 = 0.90 mug/ml), and RPMI-7951 (ED50 = 0.62 mug/ml) tumor cells.
引用
收藏
页码:1488 / 1497
页数:10
相关论文
共 10 条
[1]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[2]   MASS SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS .32. PENTACYCLIC TRITERPENES [J].
BUDZIKIEWICZ, H ;
WILSON, JM ;
DJERASSI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (22) :3688-&
[3]   BIOGENETICALLY SIGNIFICANT TRITERPENES IN A SPECIES OF MELIACEAE - CABRALEA-POLYTRICHA A JUSS [J].
CASCON, SC ;
BROWN, KS .
TETRAHEDRON, 1972, 28 (02) :315-&
[4]  
CORREL DS, 1970, MANUIAL VASCULAR PLA, P706
[5]  
Ibers J. A., 1974, INT TABLES XRAY CRYS, VIV
[6]   TRITERPENES OF JAPANESE WHITE BIRCH AND CONFIGURATION AT C-24 OF OCOTILLOL-II AND ITS RELATED COMPOUNDS [J].
NAGAI, M ;
TANAKA, N ;
TANAKA, O ;
ICHIKAWA, S .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1973, 21 (09) :2061-2065
[7]   CABRALEA-EICHLERIANA DC (MELIACEAE) .1. STRUCTURE AND STEREOCHEMISTRY OF WOOD EXTRACTIVES [J].
RAO, MM ;
MESHULAM, H ;
ZELNIK, R ;
LAVIE, D .
TETRAHEDRON, 1975, 31 (04) :333-339
[8]   PAPYRIFERIC ACID - A TRITERPENOID FROM ALASKAN PAPER BIRCH [J].
REICHARDT, PB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4576-4578
[9]  
SHIBATA S, 1965, TETRAHEDRON LETT, P207
[10]  
TANAKA O, 1978, PHYTOCHEMISTRY, V17, P1353, DOI 10.1016/S0031-9422(00)94588-6