title: Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities.
abstract: Resveratrol was glucosylated to its 3- and 4'-β-glucosides by cultured cells of Phytolacca americana. On the other hand, cultured P. americana cells glucosylated pterostilbene to its 4'-β-glucoside. P. americana cells converted piceatannol into its 4'-β-glucoside. The 3- and 4'-β-glucosides of resveratrol were further glucosylated to 3- and 4'-β-maltosides of resveratrol, 4'-β-maltoside of which is a new compound, by cyclodextrin glucanotransferase. Resveratrol 3-β-glucoside and 3-β-maltoside showed low 2,2-diphenyl-1-picrylhydrazyl free-radical-scavenging activity, whereas other glucosides had no radical-scavenging activity. Piceatannol 4'-β-glucoside showed the strongest inhibitory activity among the stilbene glycosides towards histamine release from rat peritoneal mast cells. Pterostilbene 4'-β-glucoside showed high phosphodiesterase inhibitory activity.
authors.affiliation: a Faculty of Medicine, Department of Chemistry , Oita University , Oita , Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Sato
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Shimizu
authors.forename: Yoshiko
authors.initials: Y
authors.lastname: Shimizu
authors.forename: Masaaki
authors.initials: M
authors.lastname: Akagi
authors.forename: Yuki
authors.initials: Y
authors.lastname: Eshita
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Ozaki
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Nakajima
authors.forename: Kohji
authors.initials: K
authors.lastname: Ishihara
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Masuoka
authors.forename: Hiroki
authors.initials: H
authors.lastname: Hamada
authors.forename: Kei
authors.initials: K
authors.lastname: Shimoda
authors.forename: Naoji
authors.initials: N
authors.lastname: Kubota
mesh_terms: D000818:Animals; D018926:Anti-Allergic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds; D002460:Cell Line; D060326:Chemistry Techniques, Synthetic; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry*; D006636:Histamine Release / Q000187:drug effects; D008297:Male; D018696:Neuroprotective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010726:Phosphodiesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates; D051381:Rats; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D018926:Anti-Allergic Agents; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D006027:Glycosides; D018696:Neuroprotective Agents; D010726:Phosphodiesterase Inhibitors; D010851:Picrates; D013267:Stilbenes; C107773:pterostilbene; C041525:3,3',4,5'-tetrahydroxystilbene; C004931:1,1-diphenyl-2-picrylhydrazyl; D000077185:Resveratrol
keywords: glycoside; piceatannol; pterostilbene; resveratrol