Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-11-26 DOI:10.1021/acs.jnatprod.4c00987

Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon

引用次数: 0

Abstract

A bioassay-guided chemical investigation of an Australian pasture-soil-derived Streptomyces sp. yielded the rare carbocyclic ansa-polyketide kendomycin (1) along with a series of new analogues, goondomycins A-H (2-9), featuring unprecedented carbo/heterocyclic scaffolds and chromophores, with structures assigned by detailed spectroscopic analysis, chemical and biochemical transformations, and biosynthetic considerations. Goondomycins B (2) and F (7) are noteworthy in being potent motility inhibitors of heartworm Dirofilaria immitis microfilaria (EC₅₀ 0.3 and 0.5 μM) and L4 larvae (EC₅₀ 1.4 and 1.8 μM), while exhibiting no significant antibacterial and antifungal activity or cytotoxicity to mammalian cells.

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Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.

在生物测定的指导下，对澳大利亚牧场土壤中的链霉菌进行了化学研究，发现了罕见的碳环ansa-polyketide kendomycin (1)，以及一系列新的类似物，即鹅膏霉素A-H (2-9)，它们具有前所未有的碳环/杂环支架和发色团，其结构是通过详细的光谱分析、化学和生化转化以及生物合成考虑确定的。值得注意的是，鹅膏菌素 B (2) 和 F (7) 是一种强效的蠕动抑制剂，可抑制心丝虫 Dirofilaria immitis 微丝蚴 (EC50 0.3 和 0.5 μM) 和 L4 幼虫 (EC50 1.4 和 1.8 μM)，同时对哺乳动物细胞没有明显的抗菌和抗真菌活性或细胞毒性。

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.