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A novel tetracyclic polyketide uniquely spiro-attached with a γ-lactone ring and a potent cytotoxic agent possessing a thiol-reactive pharmacophore were isolated from the mangrove endophytic fungus Penicillium chermesinum.

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New protoberberine alkaloids, namely alangiumkaloids A (1) and B (2), 27-O-trans-caffeoylcylicodiscic acid (3), and β-Dglucopyranos-1-yl N-methylpyrrole-2-carboxylate (5) together with myriceric acid B (4), isoalangiside (6), alangiside (7), 3-O-demethyl-2-O-methylalangiside (8), and demethylalangiside (9) have been isolated from Alangium salviifolium. The cancer chemopreventive properties and cytotoxic activities of the isolated compounds were evaluated. Compounds 3, 4, and 9 scavenged DPPH free radicals with IC 50 values of 21.4, 21.8, and 24.0 μM, respectively. Alangisides 7 and 9 inhibited superoxide anion radical formation in the xanthine/