title: Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol.
abstract: To enhance their water solubility and pharmacological activities, the stilbenes resveratrol, pterostilbene, and piceatannol were glycosylated to their monoglucosides (β-glucosides) and diglycosides (β-maltosides) by cultured cells and cyclodextrin glucanotransferase (CGTase). Cultured cells of Phytolacca americana and glucosyltransferase (PaGT) were capable of glucosylation of resveratrol to its 3- and 4'-β-glucosides. Pterostilbene was slightly transformed into its 4'-β-glucoside by P. americana cells. Piceatannol was readily converted into piceatannol 4'-β-glucoside, with the highest yield among the three substrates. The 3- and 4'-β-glucosides of resveratrol were subjected to further glycosylation by CGTase to give 3- and 4'-β-maltoside derivatives. The inhibitory action of resveratrol and pterostilbene toward histamine release induced with compound 48/80 from rat peritoneal mast cells was improved by β-glucosylation and/or β-maltosylation (i.e., the inhibitory activity for histamine release of the 3- and 4'-β-glucosides of resveratrol, the 3- and 4'-β-maltosides of resveratrol, and the 4'-β-glucoside of pterostilbene was higher than that of the corresponding aglycones, resveratrol and pterostilbene, respectively). In addition, the phosphodiesterase (PDE) inhibitory activity of resveratrol and pterostilbene was enhanced by β-glucosylation and/or β-maltosylation (i.e., the PDE inhibitory activities of the 3- and 4'-β-glucosides of resveratrol, the 4'-β-maltoside of resveratrol, and the 4'-β-glucoside of pterostilbene were higher than those of the corresponding aglycones, resveratrol and pterostilbene, respectively).
authors.affiliation: Department of Chemistry, Faculty of Medicine, Oita University, Oita, Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Shimoda
authors.affiliation: Department of Chemistry, Faculty of Medicine, Oita University, Oita, Japan.
authors.forename: Naoji
authors.initials: N
authors.lastname: Kubota
authors.affiliation: Department of Life Science, Faculty of Science, Okayama University of Science, Okayama, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Uesugi
authors.affiliation: National Institute of Fitness and Sports, Kanoya, Japan.
authors.forename: Hatsuyuki
authors.initials: H
authors.lastname: Hamada
authors.affiliation: Department of Physics, Faculty of Medicine, Oita University, Oita, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Tanigawa
authors.affiliation: Department of Life Science, Faculty of Science, Okayama University of Science, Okayama, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Hamada
mesh_terms: D000818:Animals; D018926:Anti-Allergic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002478:Cells, Cultured; D004353:Drug Evaluation, Preclinical; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006027:Glycosides / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D020128:Inhibitory Concentration 50; D010726:Phosphodiesterase Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D029604:Phytolacca americana / Q000166:cytology / Q000378:metabolism; D010936:Plant Extracts / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D000077185:Resveratrol; D012995:Solubility; D013267:Stilbenes / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*
chemical_list: D018926:Anti-Allergic Agents; D016166:Free Radical Scavengers; D006027:Glycosides; D010726:Phosphodiesterase Inhibitors; D010936:Plant Extracts; D013267:Stilbenes; C107773:pterostilbene; C041525:3,3',4,5'-tetrahydroxystilbene; D000077185:Resveratrol
keywords: glycoside; pharmacological activity; piceatannol; pterostilbene; resveratrol; synthesis