Pullenvalenes A–D: Nitric Oxide-Mediated Transcriptional Activation (NOMETA) Enables Discovery of Triterpene Aminoglycosides from Australian Termite Nest-Derived Fungi

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-04-04 DOI:10.1021/acs.jnatprod.3c01233

Amila Agampodi Dewa, Zeinab G. Khalil, Waleed M. Hussein, Shengbin Jin, Yanan Wang, Pablo Cruz-Morales and Robert J. Capon*,

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引用次数: 0

Abstract

We report on the use of nitric oxide-mediated transcriptional activation (NOMETA) as an innovative means to detect and access new classes of microbial natural products encoded within silent biosynthetic gene clusters. A small library of termite nest- and mangrove-derived fungi and actinomyces was subjected to cultivation profiling using a miniaturized 24-well format approach (MATRIX) in the presence and absence of nitric oxide, with the resulting metabolomes subjected to comparative chemical analysis using UPLC-DAD and GNPS molecular networking. This strategy prompted study of Talaromyces sp. CMB-TN6F and Coccidiodes sp. CMB-TN39F, leading to discovery of the triterpene glycoside pullenvalenes A–D (1–4), featuring an unprecedented triterpene carbon skeleton and rare 6-O-methyl-N-acetyl-d-glucosaminyl glycoside residues. Structure elucidation of 1–4 was achieved by a combination of detailed spectroscopic analysis, chemical degradation, derivatization and synthesis, and biosynthetic considerations.

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普伦缬氨酸 A-D：一氧化氮介导的转录激活（NOMETA）有助于从澳大利亚白蚁巢穴衍生真菌中发现三萜氨基糖苷类化合物

我们报告了利用一氧化氮介导的转录激活（NOMETA）作为一种创新手段来检测和获取沉默生物合成基因簇内编码的新类别微生物天然产物的情况。在一氧化氮存在和不存在的情况下，使用微型化 24 孔格式方法（MATRIX）对白蚁巢穴和红树林衍生真菌和放线菌的小型文库进行了培养分析，并使用 UPLC-DAD 和 GNPS 分子网络对由此产生的代谢组进行了比较化学分析。这种策略促进了对 Talaromyces sp. CMB-TN6F 和 Coccidiodes sp. CMB-TN39F 的研究，发现了三萜糖苷 pullenvalenes A-D（1-4），其特点是具有前所未有的三萜碳骨架和罕见的 6-O-甲基-N-乙酰-d-氨基葡萄糖苷残基。通过详细的光谱分析、化学降解、衍生化和合成以及生物合成的综合考虑，1-4 的结构得以阐明。

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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.