从海洋海绵中发现的 Jasplakinolide（Jaspamide）类似物的新结构和生物活性特性。
New structures and bioactivity properties of jasplakinolide (jaspamide) analogues from marine sponges.
机构信息
Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz,California 95064, USA.
出版信息
J Med Chem. 2010 Feb 25;53(4):1651-61. doi: 10.1021/jm9013554.
Abstract
The goal of this study was to isolate and study additional jasplakinolide analogues from two taxonomically distinct marine sponges including two Auletta spp. and one Jaspis splendens. This led to the isolation of jasplakinolide (1) and eleven jasplakinolide analogues (3-13) including seven new analogues (6-10, 12, and 13). Structure elucidation of the new compounds was based on a combination of 1D and 2D NMR analysis, optical rotation, circular dichroism, and preparation of Mosher's esters. Five of the new compounds are oxidized tryptophan derivatives of 1, including a unique quinazoline derivative (9). Compounds 1, 3, 5-8, and 11 were evaluated in the NCI 60 cell line screen, and all compounds were tested in a microfilament disruption assay. Jasplakinolide B (11) exhibited potent cytotoxicity (GI(50) < 1 nM vs human colorectal adenocarcinoma (HCT-116) cells) but did not exhibit microfilament-disrupting activity at 80 nM.
摘要
本研究的目的是从两种分类上不同的海洋海绵中分离并研究其他的 Jasplakinolide 类似物，包括两种 Auletta 属和一种 Jaspis splendens。这导致了 Jasplakinolide（1）和 11 种 Jasplakinolide 类似物（3-13）的分离，包括 7 种新的类似物（6-10、12 和 13）。新化合物的结构阐明基于 1D 和 2D NMR 分析、旋光、圆二色性和 Mosher 酯的制备的组合。其中 5 种新化合物是 1 的氧化色氨酸衍生物，包括一种独特的喹唑啉衍生物（9）。化合物 1、3、5-8 和 11 在 NCI 60 细胞系筛选中进行了评估，所有化合物均在微丝断裂测定中进行了测试。Jasplakinolide B（11）表现出很强的细胞毒性（GI（50）<1 nM 对人结直肠腺癌细胞（HCT-116）），但在 80 nM 时没有表现出微丝断裂活性。
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