title: Microbial mannosidation of bioactive chlorogentisyl alcohol by the marine-derived fungus Chrysosporium synchronum.
abstract: 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 IC(50) values of 1.0 and 4.7 µM, respectively. The compounds 1 and 2 were more active than the positive control, L-ascorbic acid (IC(50), 20.0 µM).
authors.affiliation: Department of Chemistry, Pukyong National University, Busan, Korea.
authors.forename: Keumja
authors.initials: K
authors.lastname: Yun
authors.forename: Chinni Mahesh
authors.initials: CM
authors.lastname: Kondempudi
authors.forename: Hong Dae
authors.initials: HD
authors.lastname: Choi
authors.forename: Jung Sook
authors.initials: JS
authors.lastname: Kang
authors.forename: Byeng Wha
authors.initials: BW
authors.lastname: Son
mesh_terms: D000438:Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D059001:Aquatic Organisms / Q000382:microbiology*; D001205:Ascorbic Acid / Q000494:pharmacology; D019905:Benzyl Alcohol / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001592:Benzyl Alcohols / Q000737:chemistry* / Q000494:pharmacology; D002912:Chrysosporium / Q000737:chemistry / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C559419:1-O-(alpha-D-mannopyranosyl)chlorogentisyl alcohol; D000438:Alcohols; D001592:Benzyl Alcohols; D016166:Free Radical Scavengers; C559535:chlorogentisyl alcohol; D019905:Benzyl Alcohol; D008358:Mannose; D001205:Ascorbic Acid; C004771:2,5-dihydroxybenzyl alcohol