柑橘霉素A和B以及柑橘霉素A类似物的全合成与生物学研究。

Total syntheses and biological investigations of tamandarins A and B and tamandarin A analogs.

作者信息

Liang B, Richard D J, Portonovo P S, Joullié M M

机构信息

Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

J Am Chem Soc. 2001 May 16;123(19):4469-74. doi: 10.1021/ja010222c.

DOI:10.1021/ja010222c

PMID:11457232

Abstract

Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

摘要

柑橘霉素A（1）和B（2）是两种结构与双溴菌素B（3）相似的天然产物，最近从巴西被囊动物门的一种海鞘中分离得到。据报道，1在体外对各种人类癌细胞系的细胞毒性比3略强。本报告描述了1和2的首次全合成，以及柑橘霉素A侧链类似物的合成。这些化合物的细胞毒性数据表明，侧链修饰对双溴菌素和柑橘霉素都有类似的影响。这一观察结果支持了柑橘霉素作为双溴菌素模拟物的作用。