Insights into the Natural Occurrence of Monomeric and Dimeric Chromanone Lactones.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-09 DOI:10.1021/acs.orglett.5c01052

Falei Zhang,Chuanteng Ma,Wenxue Wang,Meilin Zhu,Guojian Zhang,Tianjiao Zhu,Qian Che,Dehai Li

引用次数: 0

Abstract

Chromanone lactones (CLs) are a group of fungal metabolites biologically linked to tetrahydroxanthones (THXs); however, their formation in nature, particularly the occurrence of dimeric CLs, remains largely unknown. Herein, we report the discovery and identification of a biosynthetic gene cluster (ble) for the production of dimeric CLs in Dothideomycetes sp. BMC-101 through genome mining. Investigations into the biosynthetic pathway reveal that the CL moiety is derived from a THX derivative via a nonenzymatic retro-Dieckmann fragmentation. Furthermore, we demonstrate that the P450 monooxygenase BleJ accepts only THXs, rather than CLs, as substrates for dimerization. Subsequently, the THX dimers can convert into CL dimers spontaneously. Our work not only explores the spontaneous conversion of THXs to CLs, which supports the natural occurrence of CLs, but also demonstrates that CL dimers do not arise from the dimerization of CL monomers.

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对天然存在的单体和二聚体铬内酯的认识。

铬酮内酯（CLs）是一组与四羟基蒽酮（THXs）生物相关的真菌代谢物；然而，它们在自然界的形成，特别是二聚体CLs的发生，在很大程度上仍然是未知的。本文报道了通过基因组挖掘，在Dothideomycetes sp. BMC-101中发现并鉴定了一个生产二聚体CLs的生物合成基因簇（ble）。对生物合成途径的研究表明，CL片段是通过非酶逆转录dieckmann片段从THX衍生物中衍生出来的。此外，我们证明了P450单加氧酶BleJ只接受thx，而不是CLs作为二聚化的底物。随后THX二聚体可以自发转化为CL二聚体。我们的工作不仅探索了thx到CL的自发转化，这支持了CL的自然发生，而且还证明了CL二聚体不是由CL单体的二聚化产生的。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.