大拉米德A - C，来自海洋蓝藻纤细鞘丝藻的含惕各酸且具有弹性蛋白酶抑制活性的环缩肽。
Largamides A-C, tiglic acid-containing cyclodepsipeptides with elastase-inhibitory activity from the marine cyanobacterium Lyngbya confervoides.
作者信息
Matthew Susan, Paul Valerie J, Luesch Hendrik
机构信息
Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
出版信息
Planta Med. 2009 Apr;75(5):528-33. doi: 10.1055/s-0029-1185332. Epub 2009 Feb 12.
Abstract
Three unusual tiglic acid-containing cyclodepsipeptides, possessing the revised regioisomeric structures for largamides A-C (1-3), have been isolated from the marine cyanobacterium Lyngbya confervoides collected from southeastern Florida. The two-dimensional structures were determined by NMR spectroscopy and the absolute configurations by chiral HPLC analysis of degradation products. Compounds 1-3 are moderate inhibitors of mammalian elastase activity in vitro with IC(50) values ranging from 0.53 to 1.41 microM.
摘要
从佛罗里达州东南部采集的海洋蓝藻纤细鞘丝藻（Lyngbya confervoides）中分离出了三种不同寻常的含惕各酸环缩肽，它们具有修正后的大酰胺A - C（1 - 3）区域异构体结构。通过核磁共振光谱确定了二维结构，并通过对降解产物的手性高效液相色谱分析确定了绝对构型。化合物1 - 3在体外是哺乳动物弹性蛋白酶活性的中度抑制剂，IC(50)值范围为0.53至1.41微摩尔。
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5
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6
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7
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8
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