Eremophilane-Type Sesquiterpenes from a Marine-Derived Fungus Penicillium Copticola with Antitumor and Neuroprotective Activities

• Published in: Marine drugs Vol. 20; no. 11; p. 712
• Main Authors: Zhang, Jianping, Liu, Dong, Fan, Aili, Huang, Jian, Lin, Wenhan
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 13.11.2022; MDPI
• Subjects: Analogs; Anticancer properties; Antimitotic agents; Antineoplastic agents; antitumor activity; Antitumour agents; Aromatic compounds; Biological products; Carbon; Chemical properties; copteremophilanes A–J; Fungi; Glycosides; Health aspects; Identification and classification; Lung cancer; marine fungus; Marine invertebrates; Marine resources; Migrations; Neuroprotection; Neuroprotective agents; Non-small cell lung carcinoma; Penicillium; Penicillium copticola; Pharmaceutical research; Sesquiterpenes; Small cell lung carcinoma; structure elucidation; China
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md20110712

Chemical examination of a marine sponge-associated Penicillium copticola fungus resulted in the isolation of ten undescribed eremophilanes, namely copteremophilanes A–J (1–10), along with two new glycosides, 5-glycopenostatin F (11) and 5-glucopenostatin I (12). Their structures were determined by extensive spectroscopic data, in association with ECD data and chemical conversions for configurational assignments. Analogs 1, 2, and 10 represent a group of uncommon skeletons of eremophilanes with an aromatic ring and a methyl migration from C-5 to C-9, and analogs 11 and 12 are characteristic of a PKS scaffold bearing a glucose unit. The incorporation of a chlorinated phenylacetic unit in 3–9 is rarely found in nature. Analog 7 showed neuroprotective effect, whereas 8 exhibited selective inhibition against human non-small cell lung cancer cells (A549). This study enriched the chemical diversity of eremophilanes and extended their bioactivities to neuroprotection.