Paspalines C–D and Paxillines B–D: New Indole Diterpenoids from Penicillium brefeldianum WZW-F-69

• Published in: Marine drugs Vol. 20; no. 11; p. 684
• Main Authors: Lin, Weiwen, Li, Hanpeng, Wu, Zhiwen, Su, Jingyi, Zhang, Zehong, Yang, Li, Deng, Xianming, Xu, Qingyan
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 29.10.2022; MDPI
• Subjects: Abalone culture; Antiinfectives and antibacterials; Antimicrobial activity; Aquaculture; Cancer; Carbon; Cell cycle; Cell lines; Cells; Cytotoxicity; Disease resistance; Diterpenes; Fungi; indole diterpenoids; marine fungus; Marine molluscs; Natural products; NMR; Nuclear magnetic resonance; paspalines; paxillines; Penicillium; Penicillium brefeldianum; Polyculture (aquaculture); Ring structures; Tumor cell lines; Two dimensional analysis
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md20110684

Five new indole diterpenoids named paspaline C–D (1–2) and paxilline B–D (3–5), as well as eleven known analogues (6–16), were identified from fungus Penicillium brefeldianum strain WZW-F-69, which was isolated from an abalone aquaculture base in Fujian province, China. Their structures were elucidated mainly through 1D- and 2D-NMR spectra analysis and ECD comparison. Compound 1 has a 6/5/5/6/6/8 hexacyclic ring system bearing 2,2-dimethyl-1,3-dioxocane, which is rare in natural products. Compound 2 has an unusual open F-ring structure. The cytotoxic activities against 10 cancer cell lines and antimicrobial activities against model bacteria and fungi of all compounds were assayed. No compound showed antimicrobial activity, but at a concentration of 1 μM, compounds 1 and 6 exhibited the highest inhibition rates of 71.2% and 83.4% against JeKo-1 cells and U2OS cells, respectively.