来自 NIES-3585 Nodularia sp.蓝藻的 Noducyclamides A1-A4、B1 和 B2

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-04-08 DOI:10.1021/acs.jnatprod.3c01272
Jakia Jerin Mehjabin, Chin-Soon Phan and Tatsufumi Okino*, 
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引用次数: 0

摘要

对培养的 Nodularia sp.(NIES-3585)亲水部分进行的化学研究获得了六种新的环状脂肽,即含有 10 个氨基酸残基的结核环酰胺 A1-A4(1-4)和十二肽结核环酰胺 B1 和 B2(5 和 6)。这些脂肽的平面结构是在结合 HRMS 和一维及二维 NMR 光谱数据分析的基础上阐明的。这些肽在结构上类似于泻肽,含有非蛋白源氨基酸 3-羟基缬氨酸和 3-羟基亮氨酸以及一个 β-氨基癸酸残基。结核环酰胺(1-6)的绝对构型是通过酸水解和高级马菲分析确定的。Noducyclamide B1 (5) 对 MCF7 乳腺癌细胞株具有细胞毒性活性,IC50 值为 3.0 μg/mL (2.2 μM)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Noducyclamides A1–A4, B1, and B2 from the Cyanobacterium Nodularia sp. NIES-3585

A chemical investigation of the hydrophilic fraction of a cultured Nodularia sp. (NIES-3585) afforded six new cyclic lipopeptides, noducyclamides A1–A4 (14) containing 10 amino acid residues and dodecapeptides noducyclamides B1 and B2 (5 and 6). The planar structures of these lipopeptides were elucidated based on the combination of HRMS and 1D and 2D NMR spectroscopic data analyses. These peptides are structurally analogous to laxaphycins and contain the nonproteinogenic amino acids 3-hydroxyvaline and 3-hydroxyleucine and a β-amino decanoic acid residue. The absolute configurations of the noducyclamides (16) were determined by acid hydrolysis, followed by advanced Marfey’s analysis. Noducyclamide B1 (5) showed cytotoxic activities against MCF7 breast cancer cell lines with an IC50 value of 3.0 μg/mL (2.2 μM).

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来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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