Synthesis of 3, 4-Dimethoxyphenyl β-D-Glucopyranoside and Its Related Glycosides by Cultured Plant Cells

Abstract

3, 4-Dimethoxyphenol (3, 4-DMP) was converted into the corresponding glucoside in suspension-cultured cells of Coffea arabica. The maximum efficiency of glucosylation was attained, more than 40%, within 96 h after the addition of 1mM 3, 4-DMP when cultured in a modified Murashige and Skoog's medium with 5μM 2, 4-dichlorophenoxyacetic acid and 0.5μM kinetin. The glucoside was identified as 3, 4-dimethoxyphenyl β-D-glucopyranoside (3, 4-DMP glucoside) by ¹H-NMR and hydrolysis with α- and β-glucosidases. As the application of the glycosylation by C. arabica cells, eleven glycosides were obtained from seven methoxyphenols including 3, 4-DMP.