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来自水华淡水蓝藻 Stigonema sp. 的含 Ahp 的弹性蛋白酶抑制活性环二肽 Stigonemapeptin

Stigonemapeptin, an Ahp-containing depsipeptide with elastase inhibitory activity from the bloom-forming freshwater cyanobacterium Stigonema sp.

机构信息

Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612, USA.

出版信息

J Nat Prod. 2012 Apr 27;75(4):807-11. doi: 10.1021/np300150h. Epub 2012 Apr 6.

DOI:10.1021/np300150h
PMID:22483033
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3338906/
Abstract

Stigonemapeptin (1), a depsipeptide containing an Ahp (3-amino-6-hydroxy-2-piperidone) residue, was isolated from a bloom sample of the freshwater cyanobacterium Stigonema sp. collected from North Nokomis Lake in the Highland Lake District of northern Wisconsin. The planar structure was determined by 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of the amino acids were determined using the advanced Marfey's method after acid hydrolysis. Stigonemapeptin (1), characterized by the presence of the Ahp residue, also contained the modified amino acids Abu (2-amino-2-butenoic acid) and N-formylated Pro. Stigonemapeptin (1) showed in vitro elastase and chymotrypsin inhibitory activity, with IC(50) values of 0.26 and 2.93 μM, respectively.

摘要

石蒜肽素（1）是一种含有 Ahp（3-氨基-6-羟基-2-哌啶酮）残基的环二肽，从威斯康星州北部高地湖区北诺克米斯湖采集的淡水蓝藻石蒜属的水华样本中分离得到。通过 1D 和 2D NMR 实验以及 HRESIMS 分析确定了其平面结构。通过酸水解后的先进 Marfey 法确定了氨基酸的绝对构型。石蒜肽素（1）的特征是含有 Ahp 残基，还含有修饰氨基酸 Abu（2-氨基-2-丁烯酸）和 N-甲酰基 Pro。石蒜肽素（1）对弹性蛋白酶和糜蛋白酶具有体外抑制活性，IC50值分别为 0.26 和 2.93 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b4/3338906/8ba499791519/nihms369320f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b4/3338906/8ba499791519/nihms369320f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b4/3338906/8ba499791519/nihms369320f1.jpg

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