Document Detail

Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides.
MedLine Citation:
PMID:  16950623     Owner:  NLM     Status:  MEDLINE    
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.
Marienca Femenía-Ríos; Carlos M García-Pajón; Rosario Hernández-Galán; Antonio J Macías-Sánchez; Isidro G Collado
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't     Date:  2006-09-06
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  16     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2006 Nov 
Date Detail:
Created Date:  2006-10-09     Completed Date:  2007-01-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  5836-9     Citation Subset:  IM    
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, s/n, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
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MeSH Terms
Acetates / chemical synthesis,  pharmacology*
Antifungal Agents / chemical synthesis*,  pharmacology
Butylated Hydroxytoluene / pharmacology
Caffeic Acids / pharmacology
Colletotrichum / metabolism*
Free Radical Scavengers / metabolism*
Furans / chemical synthesis,  pharmacology*
Hydroxybenzoic Acids / pharmacology
Peracetic Acid / analogs & derivatives,  chemical synthesis,  pharmacology*
Plant Diseases / microbiology
Reg. No./Substance:
0/2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran; 0/Acetates; 0/Antifungal Agents; 0/Caffeic Acids; 0/Free Radical Scavengers; 0/Furans; 0/Hydroxybenzoic Acids; 128-37-0/Butylated Hydroxytoluene; 331-39-5/caffeic acid; 79-21-0/Peracetic Acid; 99-50-3/protocatechuic acid

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