Meroterpenoids from the fungus Penicillium sclerotiorum GZU-XW03-2 and their anti-inflammatory activity. (October 2022)

• Record Type: Journal Article
• Authors: Zhao, Min; Chen, Xiao-Cong; Pan, Wen-Cong; Liu, Xia; Tan, Shao-Li; Cui, Hui; Zhao, Zhong-Xiang
• Is Part Of: Phytochemistry. Volume 202(2022)
• Publication Date: 2022-10
• Subjects: Penicillium sclerotiorum -- Trichocomaceae -- Meroterpenoids -- Anti-inflammatory activity -- iNOS inhibitor; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113307
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven undescribed meroterpenoids, peniscmeroterpenoids A − G, were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03-2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid A possessed an unprecedented and highly oxidized 6/7/6/5/5 pentacyclic system, featuring a unique tetrahydrofuro [2, 3-b]furan-2(3 H )-one motif. Peniscmeroterpenoids B − E owned rare 6(D)/5(E) fused rings were not common in natural products, and peniscmeroterpenoid E is the first example of a berkeleyone analogue stripped of the methyl ester fragment. In bioassays, peniscmeroterpenoids A and D inhibited the production of nitric oxide (NO) in RAW264.7 cells with IC50 values of 26.60 ± 1.15 and 8.79 ± 1.22 μM. Moreover, peniscmeroterpenoid D significantly suppressed the production of pro-inflammatory mediators (COX-2, IL-1 β and IL-6) and the protein expression of the enzyme iNOS. Graphical abstract: Seven undescribed meroterpenoids, peniscmeroterpenoids A − G, were isolated from the marine-derived fungus Penicillium sclerotiorum . And, peniscmeroterpenoid D acts by inhibiting the expression of inflammatory factors. Image 1 Highlights: Peniscmeroterpenoid A possessed an unprecedented and highly oxidized 6/7/6/5/5 pentacyclic system. Peniscmeroterpenoids B − E owned rare 6(D)/5(E) fused rings were not common in natural. Peniscmeroterpenoid D with a unique 6/6/6/5 tetracyclic skeleton was a good iNOS inhibitor.