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A chemical investigation on an endophytic fungus  Penicillium expansum  isolated from the medicinal plant  Plantago depressa  Willd. (Plantaginaceae) afforded one new diketopiperazine-type alkaloid, namely penicimine A ( 1 ), as well as two known congeners ( 2  and  3 ). Their structures were elucidated by widespread spectroscopic data, and the absolute configurations of  1  and  2  were further confirmed by single-crystal X-ray diffraction analyses. Compound  1  represented the first example of benzyl-containing diketopiperazine-type alkaloid bearing a methyl group attached at C-15 position. Compound  1  showed anti-inflammatory activity against LPS-induced nitric oxide (NO) production in RAW264.7 mouse macrophages with an IC 50  value of 25.65 μM.

A new diketopiperazine-type alkaloid from the endophytic fungus Penicillium expansum