title: Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides.
abstract: A novel metabolite (-)-1 was isolated as its peracetylated derivative, (-)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran (2), from a strain of the phytopathogenic fungus Colletotrichum gloeosporioides CECT 20122. The synthesis of (-)-1 was carried out by ring-closing metathesis of diene 6 and stereoselective dihydroxylation of a dihydrofuran derivative 7 as key steps. The tetraol (-)-1 showed free radical scavenging activity comparable to that of BHT, caffeic acid or protocatechuic acid.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, s/n, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
authors.forename: Marienca
authors.initials: M
authors.lastname: Femenía-Ríos
authors.forename: Carlos M
authors.initials: CM
authors.lastname: García-Pajón
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernández-Galán
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Macías-Sánchez
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D002109:Caffeic Acids / Q000494:pharmacology; D020231:Colletotrichum / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000378:metabolism*; D005663:Furans / Q000138:chemical synthesis / Q000494:pharmacology*; D062385:Hydroxybenzoates / Q000494:pharmacology; D010463:Peracetic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology
chemical_list: C515788:2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran; D000085:Acetates; D000935:Antifungal Agents; D002109:Caffeic Acids; D016166:Free Radical Scavengers; D005663:Furans; D062385:Hydroxybenzoates; D002084:Butylated Hydroxytoluene; C009091:protocatechuic acid; D010463:Peracetic Acid; C040048:caffeic acid