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来自海洋蓝藻两个帕尔米拉环礁样本的林格比藻毒素K-N

Lyngbyabellins K-N from Two Palmyra Atoll Collections of the Marine Cyanobacterium .

作者信息

Choi Hyukjae, Mevers Emily, Byrum Tara, Valeriote Frederick A, Gerwick William H

机构信息

Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Dr. MC 0212, La Jolla, CA, 92093, USA.

Department of Chemistry and Biochemistry, University of California San Diego,9500 Gilman Dr., La Jolla, CA, 92093, USA.

出版信息

European J Org Chem. 2012 Sep 1;2012(27):5141-5150. doi: 10.1002/ejoc.201200691. Epub 2012 Aug 14.

Abstract

Five lipopeptides of the lyngbyabellin structure class, four cyclic (, and ) and one linear (), were isolated from the extracts of two collections of filamentous marine cyanobacteria obtained from Palmyra Atoll in the Central Pacific Ocean. Their planar structures and absolute configurations were elucidated by combined spectroscopic and chromatographic analyses as well as chemical synthesis of fragments. In addition to structural features typical of the lyngbyabellins, such as two thiazole rings and a chlorinated 2-methyloctanoate residue, these new compounds possess several unique aspects. Of note, metabolites and possessed rare mono-chlorination on the 3-acyloxy-2-methyloctanoate residue while lyngbyabellin N () had an unusual -dimethylvaline terminus. Lyngbyabellin N also possessed a leucine statine residue, and showed strong cytotoxic activity against HCT116 colon cancer cell line (IC = 40.9 ± 3.3 nM).

摘要

从取自中太平洋帕尔米拉环礁的两批丝状海洋蓝细菌提取物中分离出了5种具有林格比阿贝林结构类别的脂肽,其中4种为环状(、和),1种为线性()。通过光谱和色谱分析相结合以及片段的化学合成阐明了它们的平面结构和绝对构型。除了林格比阿贝林典型的结构特征,如两个噻唑环和一个氯化2-甲基辛酸残基外,这些新化合物还具有几个独特之处。值得注意的是,代谢物和在3-酰氧基-2-甲基辛酸残基上具有罕见的单氯化,而林格比阿贝林N()具有不寻常的-二甲基缬氨酸末端。林格比阿贝林N还具有亮氨酸他汀残基,并对HCT116结肠癌细胞系表现出强细胞毒性活性(IC = 40.9±3.3 nM)。

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