从培养的淡水蓝藻螺旋鱼腥藻中分离得到纳马霉素 B 和 C 以及 Spumigins K-N。

Namalides B and C and Spumigins K-N from the Cultured Freshwater Cyanobacterium Sphaerospermopsis torques-reginae.

机构信息

Department of Clinical and Toxicological Analyses, School of Pharmaceutical Sciences, University of São Paulo , Avenida Prof. Lineu Prestes 580, 05508-900, São Paulo, SP, Brazil.

Department of Biochemistry, Institute of Chemistry, University of São Paulo , Avenida Prof. Lineu Prestes 748, 05508-900, São Paulo, SP, Brazil.

出版信息

J Nat Prod. 2017 Sep 22;80(9):2492-2501. doi: 10.1021/acs.jnatprod.7b00370. Epub 2017 Sep 6.

DOI:10.1021/acs.jnatprod.7b00370

PMID:28876933

Abstract

Chemical investigations of the terrestrial cyanobacterium Sphaerospermopsis torques-reginae ITEP-024 from northern Brazil afforded namalides B (1) and C (2), the first analogues of this anabaenopeptide-like metabolite to be described. Four other related peptides (3-6), termed spumigins K-N, were also identified. Planar structures and absolute configurations for 1, 2, and 3a-6a were deduced by a combination of 2D NMR, HRMS analysis, and Marfey's methodology. Spumigins K-N (3-6) are the first examples of spumigins containing a 2-hydroxy-4-(4-hydroxyphenyl)butanoic acid (Hhpba) in the N-terminal position. Compounds 1 and 2 inhibited carboxypeptidase A with IC values of 0.75 and 2.0 μM, respectively.

摘要

对来自巴西北部的陆生蓝藻 Sphaerospermopsis torques-reginae ITEP-024 的化学研究得到了 namalides B（1）和 C（2），这是首次描述这种类似 anabaenopeptide 的代谢物的类似物。还鉴定了另外四种相关肽（3-6），称为 spumigins K-N。通过二维 NMR、高分辨率质谱分析和 Marfey 方法的组合，推断出 1、2 和 3a-6a 的平面结构和绝对构型。Spumigins K-N（3-6）是第一个在 N 端含有 2-羟基-4-（4-羟基苯基）丁酸（Hhpba）的 spumigins 实例。化合物 1 和 2 对羧肽酶 A 的抑制作用的 IC 值分别为 0.75 和 2.0 μM。