Salicylaldehyde derivatives represent a class of benzene carbaldehydes usually bearing hydroxyl groups, prenyl moieties, and saturated or unsaturated side chains. They are widely distributed in terrestrial, plant endophytic, and marine-derived fungi, exhibiting cytotoxic, antibacterial, antifungal, and antioxidant activities. Chemically, the prenyl group and side chain can cyclize in different patterns and fuse to the salicylaldehyde nucleus, affording diverse kinds of polycyclic chemical scaffolds.1 In our ongoing search for bioactive secondary metabolites from marine fungi, nine pairs of unprecedented polycyclic salicylaldehyde derivative enantiomers, euroticins A-I, as well as a known one were isolated from a marine-derived fungus Eurotium sp. SCSIO F452 by a large scale fermentation. These compounds possess highly constructed 6/6/6/5/7, 6/6/6/6, 6/6/6/5, and 6/6/5 architectures. Their structures were established by comprehensive spectroscopic analyses, X-ray diffraction, ECD and 13C NMR calculations. Selected compounds showed significant α-glucosidase inhibitory and antioxidative activities, as well as moderate cytotoxic activities against a panel of cancer cell lines.2-4