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含咪唑烷酮环的马杜拉菌素：是天然产物还是萃取溶剂副反应产物？

Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents?

机构信息

Fundación MEDINA, Avda. del Conocimiento 34, 18016 Granada, Spain.

Institut Pasteur Korea, 16, Daewangpangyo-ro 712 beon-gil, Bundang-gu, Seongnam-si 13488, Gyeonggi-do, Republic of Korea.

出版信息

Int J Mol Sci. 2023 Dec 25;25(1):301. doi: 10.3390/ijms25010301.

DOI:10.3390/ijms25010301
PMID:38203471
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10779116/
Abstract

Madurastatins are a group of pentapeptides containing an oxazoline moiety, and, in a few cases, an imidazolidinone ring as an additional structural feature. In our search for new potential antiparasitic metabolites from natural sources, we studied the acetone extracts from a culture of sp. CA-135719. The LC/HRMS analysis of this extract identified the presence of the known madurastatins C1 (), D1 (), and D2 () together with additional members of the family that were identified as the new madurastatins H2 () and 33--D1 () after isolation and spectroscopic analysis. The planar structures of the new compounds were established by HRMS, ESI-qTOF-MS/MS, and 1D and 2D NMR data, and their absolute configuration was proposed using Marfey's and bioinformatic analyses of the biosynthetic gene cluster (BGC). A revision of the absolute configuration of madurastatins D1 and D2 is proposed. Additionally, madurastatins containing imidazolidinone rings are proved to be artifacts originating during acetone extraction of the bacterial cultures.

摘要

马杜拉菌素是一组含有噁唑啉部分的五肽，在少数情况下，含有咪唑烷酮环作为附加结构特征。在我们从天然来源中寻找新的潜在抗寄生虫代谢物的研究中，我们研究了 sp. CA-135719 的培养物的丙酮提取物。该提取物的 LC/HRMS 分析鉴定出已知的马杜拉菌素 C1()、D1()和 D2()的存在，以及通过分离和光谱分析鉴定为新的马杜拉菌素 H2()和 33--D1()的家族其他成员。新化合物的平面结构通过 HRMS、ESI-qTOF-MS/MS 以及 1D 和 2D NMR 数据确定，其绝对构型使用 Marfey 的和生物信息学分析生物合成基因簇 (BGC) 来提出。提出了对马杜拉菌素 D1 和 D2 的绝对构型的修订。此外，含有咪唑烷酮环的马杜拉菌素被证明是在细菌培养物的丙酮提取过程中产生的人工产物。

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