Eutypetides A—E, Structurally Intriguing Polyketides Formed by Intramolecular [4+2] Cycloaddition from Marine‐Derived Fungus Eutypella sp. F0219

IF 5.5 1区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chinese Journal of Chemistry Pub Date : 2024-09-17 DOI:10.1002/cjoc.202400716

Zhong‐Ping Jiang, Meng‐Ting Chen, Xiao Xiang, Cong‐Jun Xu, Yong Rao, Hong‐Zhi Du, Wan‐Shan Li, Ling Huang

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Abstract

Comprehensive SummaryFour polycyclic ten‐membered lactones possessing unprecedented 10/6/5 tricyclic ring skeleton, named eutypetides A—D (1—4), and an intriguing polyketide containing a hexahydroisobenzofuran‐1(3H)‐one motif, named eutypetide E (5) were isolated from the marine‐derived fungus Eutypella sp. F0219, together with three new related biosynthetic polyketides eutypetides F—H (6—8). The absolute configurations of 1—5 were unequivocally determined by single‐crystal X‐ray diffraction analyses (Cu Kα), modified Mosher's method and electronic circular dichroism (ECD) calculations. Eutypetides G (7) showed remarkable anti‐inflammatory activity and could reduce the mRNA expression of proinflammatory cytokines IL‐1β, IL‐6, TNF‐α, and iNOS induced by LPS. Most notably, compounds 1—4 were formed biogenetically from 6—7 via the key intramolecular [4+2] cycloaddition, while compound 5 could be constructed biogenetically from 8 through the intramolecular [4+2] cycloaddition. All the above eight polyketides are proposed to originate from a C10 and a C6 fatty acid.

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海洋真菌 Eutypella sp. F0219 分子内[4+2]环加成形成的结构奇特的多酮苷 Eutypetides A-E

综合摘要从海洋源真菌 Eutypella sp.F0219 中分离出来，同时分离出的还有三个新的相关生物合成多酮化合物，即丁内酯 F-H （6-8）。通过单晶 X 射线衍射分析（Cu Kα）、改进的莫舍尔法和电子圆二色性（ECD）计算，明确确定了 1-5 的绝对构型。Eutypetides G (7) 具有显著的抗炎活性，可降低 LPS 诱导的促炎细胞因子 IL-1β、IL-6、TNF-α 和 iNOS 的 mRNA 表达。最值得注意的是，化合物 1-4 是由 6-7 通过关键的分子内[4+2]环化反应生物合成的，而化合物 5 则是由 8 通过分子内[4+2]环化反应生物合成的。上述 8 种多酮类化合物均拟源于一种 C10 脂肪酸和一种 C6 脂肪酸。

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来源期刊

Chinese Journal of Chemistry 化学-化学综合

CiteScore

8.80

自引率

14.80%

发文量

422

审稿时长

1.7 months

期刊介绍： The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.