| Summary: | Chemical examination of a marine sponge-associated <i>Penicillium copticola</i> fungus resulted in the isolation of ten undescribed eremophilanes, namely copteremophilanes A–J (<b>1</b>–<b>10</b>), along with two new glycosides, 5-glycopenostatin F (<b>11</b>) and 5-glucopenostatin I (<b>12</b>). Their structures were determined by extensive spectroscopic data, in association with ECD data and chemical conversions for configurational assignments. Analogs <b>1</b>, <b>2</b>, and <b>10</b> represent a group of uncommon skeletons of eremophilanes with an aromatic ring and a methyl migration from C-5 to C-9, and analogs <b>11</b> and <b>12</b> are characteristic of a PKS scaffold bearing a glucose unit. The incorporation of a chlorinated phenylacetic unit in <b>3</b>–<b>9</b> is rarely found in nature. Analog <b>7</b> showed neuroprotective effect, whereas <b>8</b> 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.
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