Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-11-20 DOI:10.1021/acs.jnatprod.4c00832

João P A Reis, Sara Freitas, Tereza Procházková, Pedro N Leão

引用次数: 0

Abstract

The cyanobacterial dialkylresorcinol bartolosides were initially reported to feature glycosylated and halogenated moieties. Later, biosynthetic and in vitro studies showed that the chlorinated alkyl chains are utilized for a nucleophilic substitution with free fatty acid carboxylates from primary metabolism, generating bartoloside esters. Here, we applied a workflow based on PCR screening coupled to LC-HRESIMS and molecular network analysis with the aim of discovering additional bartoloside diversity. We report the annotation of 27 bartoloside and bartoloside ester derivatives, including the characterization of two new bartolosides, underlining the breadth of structures generated by bartoloside biosynthetic pathways. Some of the herein reported bartolosides feature hydroxylation in their side chains, a modification that has not been associated with this metabolite family.

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扩大蓝藻二烷基间苯二酚巴托苷家族的多样性。

最初报道的蓝藻二烷基间苯二酚酒石酸苷具有糖基化和卤化分子。后来，生物合成和体外研究表明，氯化烷基链可与初级代谢产生的游离脂肪酸羧基发生亲核取代反应，生成巴托苷酯。在此，我们采用了基于 PCR 筛选、LC-HRESIMS 和分子网络分析的工作流程，旨在发现更多的巴托苷多样性。我们报告了 27 种酒石酸苷和酒石酸苷酯衍生物的注释，包括两种新酒石酸苷的表征，强调了酒石酸苷生物合成途径产生的结构的广泛性。本文报告的一些巴托苷的侧链具有羟基化特征，这种修饰与该代谢物家族并不相关。

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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.