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).
Keywords: glycoside; pharmacological activity; piceatannol; pterostilbene; resveratrol; synthesis.
© 2015 New York Academy of Sciences.