Tonakiamides A and B, Antitrypanosomal Lipopeptides Isolated from a Marine Okeania sp. Cyanobacterium

IF 3.7 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2026-10-23 Epub Date: 2026-09-25 DOI:10.1021/acs.jnatprod.6c00670

Natsumi Watanabe, Ghulam Jeelani, Tomoyoshi Nozaki, Arihiro Iwasaki

引用次数: 0

Abstract

The structure elucidation of peptidic natural products is often hindered by extensive N-methylation and repetitive sequence motifs, which complicate NMR spectral analysis. Tonakiamides A and B (1 and 2), two lipopeptides isolated from a marine Okeania sp. cyanobacterium collected in Japan, represent such challenging compounds. Tonakiamides A and B (1 and 2) are acyclic nonapeptides composed of a hexanoic acid moiety and nine amino acid residues, six of which are N-methylated, resulting in complex mixtures of rotamers. Their structures were elucidated through a combination of spectroscopic and spectrometric analyses together with the characterization of three partial hydrolysates obtained under mild hydrolysis conditions. Tonakiamides A and B exhibited moderate growth-inhibitory activities against Trypanosoma brucei rhodesiense, the causative agent of African sleeping sickness.

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海洋蓝藻中抗锥虫体脂肽的tonakamides A和B

多肽天然产物的结构解析常常受到广泛的n -甲基化和重复序列基序的阻碍，使核磁共振光谱分析复杂化。Tonakiamides A和B(1和2)，是从日本收集的海洋Okeania sp.蓝藻中分离出来的两个脂肽，代表了这种具有挑战性的化合物。Tonakiamides A和B（1和2）是由己酸部分和9个氨基酸残基组成的无环非肽，其中6个被n甲基化，形成复杂的旋转体混合物。通过光谱学和光谱分析的结合以及在温和水解条件下得到的三种部分水解产物的表征，阐明了它们的结构。Tonakiamides A和B对非洲昏睡病的病原体——布氏罗得西亚锥虫表现出中等的生长抑制活性。

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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来源期刊

Journal of Natural Products 生物-药学

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.