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Anti-diabetic and anti-inflammatory indole diterpenes from the marine-derived fungus Penicillium sp. ZYX-Z-143

文献类型： 外文期刊

作者： Dai, Lu-Ting 1 ; Yang, Li 1 ; Guo, Jiao-Cen 1 ; Ma, Qing-Yun 1 ; Xie, Qing-Yi 1 ; Jiang, Li 3 ; Yu, Zhi-Fang 3 ; Dai, Hao-Fu 1 ; Zhao, You-Xing 1 ;

作者机构： 1.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Key Lab Res & Dev Nat Prod Li Folk Med Hainan Prov, Haikou 571101, Peoples R China

2.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Natl Key Lab Trop Crop Breeding, Haikou 571101, Peoples R China

3.Nanjing Agr Univ, Coll Food Sci & Technol, Nanjing 210095, Peoples R China

关键词： Indole diterpenoids; Penicillium sp.; PTP1B; Anti-inflammatory; alpha-glucosidase

期刊名称：BIOORGANIC CHEMISTRY （ 影响因子：5.1； 五年影响因子：5.3 ）

ISSN： 0045-2068

年卷期： 2024 年 145 卷

页码：

收录情况： SCI

摘要： Seven new indole-diterpenoids, penpaxilloids A-E (1-5), 7-methoxypaxilline-13-ene (6), and 10-hydroxy-paspaline (7), along with 20 known ones (8-27), were isolated from the marine-derived fungus Penicillium sp. ZYX-Z-143. Among them, compound 1 was a spiro indole-diterpenoid bearing a 2,3,3a,5-tetrahydro-1H-benzo[d]pyrrolo[2,1-b][1,3]oxazin-1-one motif. Compound 2 was characterized by a unique heptacyclic system featuring a rare 3,6,8-trioxabicyclo[3.2.1]octane unit. The structures of the new compounds were established by extensive spectroscopic analyses, NMR calculations coupled with the DP4 + analysis, and ECD calculations. The plausible biogenetic pathway of two unprecedented indole diterpenoids, penpaxilloids A and B (1 and 2), was postulated. Compound 1 acted as a noncompetitive inhibitor against protein tyrosine phosphatase 1B (PTP1B) with IC50 value of 8.60 +/- 0.53 mu M. Compound 17 showed significant alpha-glucosidase inhibitory activity with IC50 value of 19.96 +/- 0.32 mu M. Moreover, compounds 4, 8, and 22 potently suppressed nitric oxide production on lipopolysaccharide-stimulated RAW264.7 macrophages.

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