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.
structure elucidation, antitumor activity, Marine fungus, copteremophilanes A-J, neuroprotection, Penicillium copticola
NCBI PubMed ID: 36421990Publication DOI: 10.3390/md20110712Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: W. Lin
Institutions: State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China, Institute of Ocean Research, Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, FTIR, HPLC, UV, optical rotation measurement, HR-ESI-MS, DEPT-135, ECD, bioassays
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