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Two new cytochalasin derivatives, peniotrinins A (<b>1</b>) and B (<b>2</b>), three new citrinin derivatives, peniotrinins C–E (<b>4</b>, <b>5</b>, <b>7</b>), and one new tetramic acid derivative, peniotrinin F (<b>12</b>), along with nine structurally related known compounds, were isolated from the solid culture of <i>Peniophora</i> sp. SCSIO41203. Their structures, including the absolute configurations of their stereogenic carbons, were fully elucidated based on spectroscopic analysis, quantum chemical calculations, and the calculated ECD. Interestingly, <b>1</b> is the first example of a rare 6/5/5/5/6/13 hexacyclic cytochalasin. We screened the above compounds for their anti-prostate cancer activity and found that compound <b>3</b> had a significant anti-prostate cancer cell proliferation effect, while compounds <b>1</b> and <b>2</b> showed weak activity at 10 μM. We then confirmed that compound <b>3</b> exerts its anti-prostate cancer effect by inducing methuosis through transmission electron microscopy and cellular immunostaining, which suggested that compound <b>3</b> might be first reported as a potential anti-prostate methuosis inducer.