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Perochalasins A-C 的结构与生物合成，海洋来源真菌 M16 产生的开链 merocytochalasans

Structure and Biosynthesis of Perochalasins A-C, Open-Chain Merocytochalasans Produced by the Marine-Derived Fungus sp. M16.

机构信息

Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, São Carlos, SP, Brazil.

Department of Chemistry and BioDiscovery Institute, University of North Texas, 1155 Union Circle, Denton, Texas 76203, United States.

出版信息

J Nat Prod. 2024 Sep 27;87(9):2204-2215. doi: 10.1021/acs.jnatprod.4c00516. Epub 2024 Aug 16.

DOI:10.1021/acs.jnatprod.4c00516
PMID:39150723
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11443529/
Abstract

Novel open-chain merocytochalasans, perochalasins A-C (-), containing an unusual N-O six-membered heterocyclic moiety, were isolated from cultures of the marine-derived sp. M16 fungus, along with cytochalasin Z (), cytochalasin Z (), [12]-cytochalasin (), and phenochalasin B (). The structures of compounds - were established by analysis of the spectroscopic data. Full genome sequencing of sp. M16 enabled the identification of a cytochalasan biosynthetic gene cluster and a proposal for the biosynthetic assembly of perochalasins. The proposal is supported by the nonenzymatic conversion of phenochalasin B () into -, based on isotope-labeled hydroxylamine (NHOH and NDOD) feeding studies and . In contrast to other merocytochalasans, these are the first cytochalasans confirmed to arise via nucleophilic addition and at a distinct location from the reactive macrocycle olefin, potentially expanding further the range of merocytochalasans to be discovered or engineered. Cytochalasin Z () exhibited antiplasmodial activities in the low micromolar range against the chloroquine-sensitive 3D7 strain as well as against resistant strains of the parasite (Dd2, TM90C6B, and 3D7r_MMV848).

摘要

新型开链单环 merocytochalasans，perochalasins A-C(-)，含有一个不寻常的 N-O 六元杂环部分，从海洋来源的 sp. M16 真菌的培养物中分离出来，同时还有细胞松弛素 Z()、细胞松弛素 Z()、[12]-细胞松弛素()和 phenochalasin B()。通过分析光谱数据确定了化合物-的结构。sp. M16 的全基因组测序使我们能够鉴定出细胞松弛素生物合成基因簇，并提出了 perochalasins 的生物合成组装方案。该方案得到了基于同位素标记羟胺（NHOH 和 NDOD）喂养研究和的 phenochalasin B()非酶转化为-的支持。与其他 merocytochalasans 不同，这些是第一个通过亲核加成并在与反应性大环烯烃不同的位置产生的细胞松弛素，可能会进一步扩大 merocytochalasans 的发现或工程范围。细胞松弛素 Z()对氯喹敏感的 3D7 株以及寄生虫的耐药株（Dd2、TM90C6B 和 3D7r_MMV848）表现出低微摩尔范围内的抗疟原虫活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/555e167b71c5/np4c00516_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/1e55395527c2/np4c00516_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/7ebeb7a46d73/np4c00516_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/119972937a1c/np4c00516_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/86693395b573/np4c00516_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/36e025d64435/np4c00516_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/555e167b71c5/np4c00516_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/1e55395527c2/np4c00516_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/7ebeb7a46d73/np4c00516_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/119972937a1c/np4c00516_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/86693395b573/np4c00516_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/36e025d64435/np4c00516_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/11443529/555e167b71c5/np4c00516_0006.jpg

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