title: Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene.
abstract: The stilbene compound resveratrol was glycosylated to give its 4'-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4'-O-β-D-glucoside, and converted pinostilbene to its 4'-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.
authors.affiliation: a Faculty of Science, Department of Life Science , Okayama University of Science , Okayama , Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Uesugi
authors.affiliation: a Faculty of Science, Department of Life Science , Okayama University of Science , Okayama , Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Hamada
authors.affiliation: b Faculty of Medicine, Department of Biomedical Chemistry , Oita University , Oita , Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Shimoda
authors.affiliation: b Faculty of Medicine, Department of Biomedical Chemistry , Oita University , Oita , Japan.
authors.forename: Naoji
authors.initials: N
authors.lastname: Kubota
authors.affiliation: c Faculty of Agriculture, Department of Biological Sciences , Yamaguchi University , Yamaguchi , Japan.
authors.forename: Shin-Ichi
authors.initials: SI
authors.lastname: Ozaki
authors.affiliation: d Department of Applied Chemistry , Graduate School of Engineering, Okayama University of Science , Okayama , Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Nagatani
mesh_terms: D000363:Agaricales / Q000201:enzymology; D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005964:Glucosyltransferases / Q000378:metabolism; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D000072257:Oxygen Radical Absorbance Capacity; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D006027:Glycosides; D013267:Stilbenes; C522997:pinostilbene; C107773:pterostilbene; D014442:Monophenol Monooxygenase; D005964:Glucosyltransferases; D000077185:Resveratrol
keywords: glycoside; pinostilbene; pterostilbene; resveratrol