Peniciphenalenins A−F from the culture of a marine-associated fungus Penicillium sp. ZZ901. (August 2018)

• Record Type: Journal Article
• Authors: Li, Qiao; Zhu, Rongyao; Yi, Wenwen; Chai, Weiyun; Zhang, Zhizhen; Lian, Xiao-Yuan
• Is Part Of: Phytochemistry. Volume 152(2018)
• Page Start: 53
• Page End: 60
• Publication Date: 2018-08
• Subjects: Penicillium sp. ZZ901 -- Marine fungus -- Peniciphenalenins -- Phenalenone derivatives -- Antiproliferative activity -- Antibacterial activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.04.021
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Marine-derived fungi of the genus Penicillium represent a huge potential for synthesizing the secondary metabolites with structural and bioactive uniqueness and diversity. In this study, six previously undescribed compounds peniciphenalenins A−F and four known compounds (+)-sclerodin, (+)-scleroderolide, (+)-sclerodione, and physcion were isolated from the culture of a marine-derived fungus Penicillium sp. ZZ901. Structures of the isolated compounds were elucidated by a combination of extensive NMR spectroscopic analysis, HRESIMS data, optical rotation value, ECD calculation, and single crystal X-ray diffraction. Peniciphenalenins A−C are the second examples of the type of neoherqueinones. The possible biosynthetic route of nine phenalenone derivatives has been suggested. The known (+)-scleroderolide showed both antiproliferative activity against glioma cells with IC50 values of 23.24–37.26 μM and antibacterial activity in suppressing the growth of methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 7.0 and 9.0 μg/mL, respectively. Graphical abstract: Nine phenalenone derivatives and one anthraquinone were isolated from the culture of a marine-associated Penicillium sp. ZZ901. Peniciphenalenins A-C are the second examples of the type of neoherqueinones. The known (+)-scleroderolide showed both anti-glioma and antibacterial activities. Image 1 Highlights: Peniciphenalenins A−F were isolated from a marine fungus Penicillium sp. ZZ901. Peniciphenalenins A−C are the second examples of the type of neoherqueinones. The possible biosynthetic pathway of the phenalenone derivatives has been proposed. (+)-Scleroderolide showed both anti-glioma and antibacterial activities.