Phomoidrides E–G, three dimeric anhydrides from the fungus Pleosporales sp. give new insight to the biosynthesis of phomoidrides

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发布日期 2021-08-24

DOI 10.1039/D1QO01119G

影响因子 5.281

作者

Lihua Zhang, Yanan Wang, Le Zhang, Bingyu Liu, Chen Zhang, Daojiang Yan, Jian Bai, Youcai Hu

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摘要

Three phomoidride-type dimeric anhydrides, phomoidrides E–G (1–3), were isolated from the fungus Pleosporales sp. Their structures were elucidated by comprehensive spectroscopic analyses. Phomoidride E (1) possesses a totally new caged tricyclo[5.3.2.02;8]dodecane carbon skeleton with a newly formed five-membered bridged ring through a C–C bond. Phomoidride F (2) features a unique caged ring system containing a bicyclo[4.3.1]deca-2,6-diene fused with an additional γ-lactone ring. The identification of 1–3 offers new insight into phomoidride biosynthesis, where a new dimerization strategy with a key Claisen-like intermediate M1 instead of the previously proposed aldol-like product could be involved. 1 shows potent inhibitory activity against the HeLa cell line with an IC50 value of 1.41 μM.

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Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Phomoidrides E–G, three dimeric anhydrides from the fungus Pleosporales sp. give new insight to the biosynthesis of phomoidrides

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