Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides.
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.
Femenía-Ríos
Marienca
M
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, s/n, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
García-Pajón
Carlos M
CM
Hernández-Galán
Rosario
R
Macías-Sánchez
Antonio J
AJ
Collado
Isidro G
IG
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
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