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Three pairs of new spirocyclic alkaloid enantiomers eurotinoids A–C ( 1 – 3 ), as well as a known biogenetically related racemate dihydrocryptoechinulin D ( 4 ) were isolated from a marine-derived fungus  Eurotium  sp. SCSIO F452. Their structures were determined by spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds  1  and  2  represent the first two “ meta ” products from a non-stereoselective [4 + 2] Diels-Alder cycloaddition presumably between an enone group of a diketopiperazine alkaloid and a diene group of a benzaldehyde derivative via a new head-to-tail coupling mode biosynthetically, while  3  and  4  were “ ortho ” products. Their enantiomers exhibited different antioxidative and cytotoxic activities. The modes of action were investigated by a preliminary molecular docking study.

Three Pairs of New Spirocyclic Alkaloid Enantiomers From the Marine-Derived Fungus Eurotium sp. SCSIO F452