(±)-Feionemycin A and Chromonemycins A-D, Rearranged Aromatic Polyketides Uncovered by Type II Polyketide Gene Cluster Expression.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI:10.1021/acs.jnatprod.4c01433

Xiaofei Huang, Xiao Xu, Luning Zhou, Jiayi Li, Chuanteng Ma, Wenxue Wang, Qian Che, Dehai Li, Tianjiao Zhu, Guojian Zhang

引用次数: 0

Abstract

Two novel spiro aromatic polyketides, (+)- and (-)-feionemycin A (1), along with four atypical angucyclinones named as chromonemycins A-D (2-5), were discovered through heterologous expression of a type II polyketide gene cluster, within which one previously characterized flavoprotein monooxygenase was deactivated. Among those structures, compound 1 features an unprecedented oxaspiro[5.4]undecane architecture, and compounds 2-5 represent novel atypical angucyclinone variants derived from unusual cyclization of the polyketide chains. The structures and absolute configurations were elucidated by NMR, MS, single-crystal X-ray diffraction, theoretical NMR calculations, DP4+ probability analysis, and ECD analyses. (+)-1 showed cytotoxic activity against NCI-H446, with an IC₅₀ value of 2.26 μM.

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（±）-Feionemycin A和chromonemycin A- d，ⅱ型聚酮基因簇表达揭示的重排芳香聚酮。

通过异种表达II型聚酮基因簇，发现了两种新的螺旋芳香聚酮，(+)-和(-)-feionemycin A(1)，以及四种被命名为chromonemycin A- d的非典型氨环素（2-5），其中一种先前表征的黄蛋白单加氧酶被失活。在这些结构中，化合物1具有前所未有的oxspiro[5.4]十烷结构，而化合物2-5则代表了由于聚酮链的异常环化而产生的新型非典型环环酮变体。通过核磁共振、质谱、单晶x射线衍射、理论核磁共振计算、DP4+概率分析和ECD分析对其结构和绝对构型进行了表征。（+）-1对NCI-H446具有细胞毒活性，IC50值为2.26 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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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.