Glycosylation of hesperetin by plant cell cultures

The biotransformation of hesperetin by cultured cells of Ipomoea batatas and Eucalyptus perriniana was investigated. Three glycosides, hesperetin 3'-O-beta-D-glucopyranoside (33 mu g/g fr. wt of cells), hesperetin 3',7-O-beta-D-diglucopyranoside (217 mu g/g fr. wt of cells), and hesperetin 7-O-[6-O-(beta-D-glucopyranosyl))-beta-D-glucopyranoside (beta-gentiobioside, 22 mu g/g fr. wt of cells), together with three hitherto known glycosides, hesperetin 5-O-beta-D-glucopyranoside (23 mu g/g fr. wt of cells), hesperetin 7-O-beta-D-glucopyranoside (57 mu g/g fr. wt of cells), and hesperetin 7-O-[6-O-(alpha(alpha-L-rhamnopyranosyl)]-beta-D-glucopyranoside (beta-rutinoside, hesperidin, 13 mu g/g fr. wt of cells), were isolated from cultured suspension cells of E. perriniana that had been treated with hesperetin. Oligosaccharide chains were regioselectively formed at the C-7 position of hesperetin to afford P-gentiobioside and P-rutinoside. On the other hand, cultured L batatas cells converted hesperetin into hesperetin 3'-O-beta-D-glucopyranoside (60 mu g/g fr. wt of cells), hesperetin 5-O-beta-D-glucopyranoside (23 mu g/g fr. wt of cells), and hesperetin 7-O-beta-D-glucopyranoside (110 mu g/g fr. wt of cells). (c) 2007 Elsevier Ltd. All rights reserved.