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Eremophilane-Type Sesquiterpenes from a Marine-Derived Fungus Penicillium Copticola with Antitumor and Neuroprotective Activities
Authors:Jianping Zhang  Dong Liu  Aili Fan  Jian Huang  Wenhan Lin
Affiliation:1.State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China;2.Institute of Ocean Research, Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Abstract: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.
Keywords:marine fungus, Penicillium copticola, copteremophilanes A–  J, structure elucidation, antitumor activity, neuroprotection
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