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彼得罗西芬菌素A和B,源自海绵分离的短密青霉菌株的新型环缩肽。

Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of Penicillium brevicompactum.

作者信息

Bringmann Gerhard, Lang Gerhard, Steffens Stefan, Schaumann Karsten

机构信息

Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.

出版信息

J Nat Prod. 2004 Mar;67(3):311-5. doi: 10.1021/np034015x.

DOI:10.1021/np034015x
PMID:15043401
Abstract

A strain of Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis was investigated for its secondary metabolites. Using fast centrifugal partitioning chromatography (FCPC) two previously unknown cyclodepsipeptides, petrosifungins A (1) and B (2), were isolated, both containing two neighboring units of the nonproteinogenic amino acid l-pipecolinic acid. The absolute configurations of all amino acids were established to be l using GITC derivatization and Marfey's method. Furthermore, the known metabolite brevianamide A (3) was isolated. The likewise known compounds mycophenolic acid (4) and asperphenamate (5) were identified from their spectroscopic properties directly in the extract using HPLC-UV, -MS, and -NMR coupling.

摘要

对从地中海海绵状石海绵(Petrosia ficiformis)标本中分离得到的短密青霉(Penicillium brevicompactum)菌株的次生代谢产物进行了研究。利用快速离心分配色谱法(FCPC)分离出两种此前未知的环缩肽,即石海绵菌素A(1)和B(2),它们均含有两个相邻的非蛋白质氨基酸L-哌啶酸单元。使用GITC衍生化和马尔菲方法确定所有氨基酸的绝对构型均为L型。此外,还分离出了已知的代谢产物短柄酰胺A(3)。同样已知的化合物霉酚酸(4)和曲霉芬酸(5)通过使用HPLC-UV、-MS和-NMR联用技术,根据其光谱性质直接在提取物中鉴定出来。

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