Arahypin-16 (1), a new prenylated resveratrol with a unique dihydrobenzofuran ring, has been isolated as a microbial metabolite of resveratrol (2) from whole-cell fermentation of Aspergillus sp. SCSIOW2. The stereochemistry of 1 was determined by ECD calculations. 1 showed about half of the extracellular radical scavenging effect (IC50 = 161.4 μM) compared with resveratrol (IC50 = 80.5 μM), while on biomembranes it exhibited the same range of protection effects against free radicals generated from AAPH (IC50 = 78.6 μM and 87.9 μM).
Keywords: Aspergillus sp. SCSIOW2; DPPH scavenging activity; ECD; erythrocyte protection activity; prenylation; resveratrol.