具有多种聚合模式的Chalasoergodimers a - e-异源二聚体

IF 4.9 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2025-09-11 DOI:10.1007/s13659-025-00544-5

Ze-Hong Lin, Han-Wen Shan, Li-Kun Yang, Tian-Tian Sun, Li-Ying He, Hui-Fang Du, Ya-Hui Zhang, Shan Liu, Xu Wang, Du-Qiang Luo, Fei Cao

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引用次数: 0

摘要

从一种海产毛藻真菌中分离到5个新的异源二聚体，chalasoergodimers a - e（1-5）和3个已知的异源二聚体（6-8），以及4个毛球蛋白单体（9-12）。新化合物1 ~ 5的结构通过HRESIMS、NMR、化学计算13C NMR和ECD等方法进行了表征。其中，化合物1是由麦角糖-4,6,8(14)，22-四烯-3 - β-醇取代毛囊球蛋白Fex(9)而得，代表了毛囊球蛋白-麦角甾醇衍生物杂合体中一种新的二聚化模式。化合物2在NH-1′上具有取代，是这种在C-3′上具有r构型的二聚体类型的第一个例子。化合物3-5是由毛球蛋白和14-脱氢麦角甾醇之间的Diels-Alder环加成形成的。此外，化合物9-12对人非小细胞肺癌细胞（A549）具有显著的细胞毒活性，其中化合物 12的IC50值为5.14 μM，作用最强。图形抽象

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Chalasoergodimers A–E, heterodimers with multiple polymerization modes from a marine-derived Chaetomium sp. fungus

Five new heterodimers, chalasoergodimers A–E (1–5), and three known heterodimers (6–8), along with four chaetoglobosin monomers (9–12), were isolated from a marine-derived Chaetomium sp. fungus. The structures of new compounds 1–5 were elucidated by HRESIMS, NMR, chemical calculated ¹³C NMR and ECD methods. Among them, compound 1 was derived from C-2′ substitution of chaetoglobosin Fex (9) with ergosta-4,6,8(14),22-tetraen-3β-ol, representing a new dimerization mode among chaetoglobosin-ergosterol derivative hybrids. Compound 2 featured substitution at NH-1′ and constituted the first example of this dimeric type bearing an R-configuration at C-3′′. Compounds 3–5 were formed via a Diels–Alder cycloaddition between chaetoglobosins and 14-dehydroergosterol. Furthermore, it was revealed that compound 9–12 exhibited the significant cytotoxic activity against the human non-small cell lung cancer cell (A549), with compound 12 showing the most potent effect at an IC₅₀ of 5.14 μM.

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.