从刺果番荔枝叶中分离出的五种新的单四氢呋喃环番荔枝内酯。

Five new monotetrahydrofuran ring acetogenins from the leaves of Annona muricata.

作者信息

Zeng L, Wu F E, Oberlies N H, McLaughlin J L, Sastrodihadjo S

机构信息

Purdue University, School of Pharmacy and Pharmacal Sciences, Department of Medicinal Chemistry and Molecular Pharmacology, West Lafayette, Indiana 47907, USA.

出版信息

J Nat Prod. 1996 Nov;59(11):1035-42. doi: 10.1021/np960447e.

DOI:10.1021/np960447e

PMID:8946744

Abstract

Bioactivity-directed fractionation of the leaves of Annona muricata resulted in the isolation of annopentocins A (1), B (2), and C(3), and cis- and trans-annomuricin-D-ones (4, 5). Compounds 1-3 are the first acetogenins reported bearing a mono-tetrahydrofuran (THF) ring with one flanking hydroxyl, on the hydrocarbon side, and another hydroxyl, on the lactone side, that is one carbon away from the THF ring. Compounds 4 and 5 were obtained in a mixture and are new mono-THF ring acetogenins bearing two flanking hydroxyls and an erythro-diol located between the THF and the ketolactone rings. Compound 1 was selectively cytotoxic to pancreatic carcinoma cells (PACA-2), and 2 and 3 were selectively cytotoxic to lung carcinoma cells (A-549); the mixture of 4 and 5 was selectively cytotoxic for the lung (A-549), colon (HT-29), and pancreatic (PACA-2) cell lines with potencies equal to or exceeding those of Adriamycin.

摘要

对刺果番荔枝叶进行生物活性导向分离，得到了番荔枝戊菌素A（1）、B（2）和C（3），以及顺式和反式番荔枝霉素-D-酮（4、5）。化合物1-3是首次报道的产乙酸素，其在烃基侧带有一个单四氢呋喃（THF）环且有一个邻位羟基，在内酯侧有另一个羟基，该羟基与THF环相隔一个碳原子。化合物4和5以混合物形式获得，是带有两个邻位羟基和一个位于THF与酮内酯环之间的赤藓糖醇的新型单THF环产乙酸素。化合物1对胰腺癌细胞（PACA-2）具有选择性细胞毒性，化合物2和3对肺癌细胞（A-549）具有选择性细胞毒性；化合物4和5的混合物对肺癌（A-549）、结肠癌（HT-29）和胰腺（PACA-2）细胞系具有选择性细胞毒性，其效力等于或超过阿霉素。