Chem. Pharm. Bull., 59(4),499-501, April 2011

Note

Microbial Mannosidation of Bioactive Chlorogentisyl Alcohol by the Marine-Derived Fungus Chrysosporium synchronum

Keumja YUN,^a Chinni Mahesh KONDEMPUDI,^a Hong Dae CHOI,^b Jung Sook KANG,^c and Byeng Wha SON^*,a

^a Department of Chemistry, Pukyong National University; Busan 608-737, Korea: ^b Department of Chemistry, Dongeui University; Busan 614-714, Korea: and ^c College of Dentistry, Pusan National University; Yangsan, Gyeongnam 626-770, Korea. * To whom correspondence should be addressed. e-mail: sonbw@pknu.ac.kr

The biological transformation of the biologically active chlorogentisyl alcohol (1), isolated from the marine-derived 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-(α-D-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 μM, respectively. The compounds 1 and 2 were more active than the positive control, L-ascorbic acid (IC₅₀, 20.0 μM).

Key words marine-derived fungus; Chrysosporium synchronum; microbial mannosidation; 1-O-(α-D-mannopyranosyl)chlorogentisyl alcohol