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

• Published in: Chemical & Pharmaceutical Bulletin Vol. 59; no. 4; pp. 499 - 501
• Main Authors: Yun, Keumja, Kondempudi, Chinni Mahesh, Choi, Hong Dae, Kang, Jung Sook, Son, Byeng Wha
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 2011; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 1-O-(α-D-mannopyranosyl)chlorogentisyl alcohol; Alcohols - chemistry; Alcohols - isolation & purification; Alcohols - pharmacology; Aquatic Organisms - microbiology; Ascorbic Acid - pharmacology; Benzyl Alcohol - chemistry; Benzyl Alcohol - isolation & purification; Benzyl Alcohol - pharmacology; Benzyl Alcohols - chemistry; Benzyl Alcohols - pharmacology; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Chrysosporium - chemistry; Chrysosporium - metabolism; Chrysosporium synchronum; Free Radical Scavengers - chemistry; Free Radical Scavengers - metabolism; Free Radical Scavengers - pharmacology; Life Sciences & Biomedicine; Mannose - analogs & derivatives; Mannose - chemistry; Mannose - isolation & purification; Mannose - pharmacology; marine-derived fungus; microbial mannosidation; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Stereoisomerism; 1-O-(alpha-D-mannopyranosyl)chlorogentisyl alcohol; TRANSFORMATION; GROWTH-FACTOR RECEPTOR; STREPTOMYCES SP; Chrysosporium synchronum; METABOLISM; microbial mannosidation; HEPARIN; marine-derived fungus; ISOLATE
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.59.499

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).