title: Selective (1)O(2) quenchers, oligostilbenes, from Vitis wilsonae: structural identification and biogenetic relationship.
abstract: Two previously unknown resveratrol trimers named wilsonols A-B, as well as a resveratrol tetramer named wilsonol C, were isolated from Vitis wilsonae Veitch, together with 12 known oligostilbenes. Their chemical structures have been elucidated by detailed analyses of 1D and 2D NMR spectroscopic data, as well as chemical evidence obtained via either catalysis with HRP (horseradish peroxidase) and H(2)O(2) (hydrogen peroxide), acid, or UV irradiation. During the chemical processes, a biomimetic resveratrol tetramer named diviniferin B that has not been found in nature was obtained. These oligostilbenes showed potent scavenging abilities towards DPPH radicals and selective quenching effects on (1)O(2) radicals. Furthermore, the biogenetic transformations between the 16 oligostilbenes have been elaborated chemically to provide a comprehensive mechanism of the antioxidative defense system in this plant species.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
authors.forename: Liyan
authors.initials: L
authors.lastname: Jiang
authors.forename: Shan
authors.initials: S
authors.lastname: He
authors.forename: Cuirong
authors.initials: C
authors.lastname: Sun
authors.forename: Yuanjiang
authors.initials: Y
authors.lastname: Pan
mesh_terms: D001713:Biphenyl Compounds / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification; D010100:Oxygen / Q000737:chemistry*; D010851:Picrates / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000302:isolation & purification; D027843:Vitis / Q000737:chemistry*
chemical_list: D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D010936:Plant Extracts; D013267:Stilbenes; C577254:wilsonol A; C577255:wilsonol B; C577256:wilsonol C; C004931:1,1-diphenyl-2-picrylhydrazyl; D000077185:Resveratrol; D010100:Oxygen