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The biological transformation of the biologically active chlorogentisyl alcohol (1), isolated from the marinederived fungus Aspergillus sp., was studied. Preparative-scale fermentation of chlorogentisyl alcohol with marine-derived fungus Chrysosporium synchronum resulted in the isolation of a new glycosidic metabolite, 1-O-(aD-mannopyranosyl)chlorogentisyl alcohol (2). The stereostructure of the new metabolite obtained was assigned
on the basis of detailed spectroscopic data analyses, chemical reaction, and chemical synthesis. Compounds 1 and 2 exhibited significant radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) with IC50 values of 1.0 and 4.7 mM, respectively. The compounds 1 and 2 were more active than the positive control, Lascorbic acid (IC50, 20.0 mM).
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