Genome-informed Discovery of Monchicamides A-K: Cyanobactins from the Microcoleaceae Cyanobacterium LEGE 16532.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-24 DOI:10.1021/acs.jnatprod.4c01063

Raquel Castelo-Branco, João P Pereira, Sara Freitas, Marco Preto, Ana R Vieira, João Morais, Pedro N Leão

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引用次数: 0

Abstract

Genome mining has emerged as an important tool for the discovery of natural products and is particularly effective for the swift identification of ribosomally synthesized and post-translationally modified peptides (RiPPs). Among RiPPs, cyanobactins have gained attention due to their diverse structures and bioactive properties. Here, we explored the Microcoleaceae cyanobacterium LEGE 16532 strain and identified the mon biosynthetic gene cluster (BGC), which was predicted to encode cyanobactin-like molecules. This led to the detection of 11 macrocyclic cyanobactins, the monchicamides, some of which feature mono- or diprenylation. One of the compounds was isolated, monchicamides I (9), and its planar structure was established by LC-HRESIMS/MS data as well as 1D and 2D NMR spectroscopy, confirming forward O-prenylation in Tyr. In addition, the absolute configuration of compound 9 was determined by Marfey's method and chiral-phase HPLC. The structures of the additional cyanobactins were proposed from MS/MS data analysis. The bioactivity profile of the isolated compound was also evaluated, but no cytotoxic, antimicrobial, or antiamoebic activity was observed.

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微甘蓝科蓝细菌LEGE 16532中Monchicamides A-K: Cyanobactins的基因组信息发现。

基因组挖掘已经成为发现天然产物的重要工具，对于快速鉴定核糖体合成和翻译后修饰肽（RiPPs）特别有效。在ripp中，蓝藻菌因其多样的结构和生物活性而备受关注。本研究以微甘蓝科蓝藻LEGE 16532菌株为研究对象，鉴定出编码类蓝藻分子的单生物合成基因簇（mon biosynthetic gene cluster， BGC）。这导致了11个大环蓝藻的检测，单链酰胺，其中一些特点是单或二烯基化。其中一个化合物monchicamides I(9)被分离出来，通过lc - hremsims /MS数据以及1D和2D NMR谱图确定了其平面结构，证实了Tyr中的正向o -戊烯酰化。此外，用Marfey法和手性相高效液相色谱法测定了化合物9的绝对构型。通过质谱/质谱分析确定了其他蓝藻菌素的结构。分离的化合物的生物活性也进行了评估，但没有观察到细胞毒性，抗菌或抗阿米巴活性。

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.