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 microg/g fr. wt of cells), hesperetin 3',7-O-beta-D-diglucopyranoside (217 microg/g fr. wt of cells), and hesperetin 7-O-[6-O-(beta-D-glucopyranosyl)]-beta-d-glucopyranoside (beta-gentiobioside, 22 microg/g fr. wt of cells), together with three hitherto known glycosides, hesperetin 5-O-beta-d-glucopyranoside (23 microg/g fr. wt of cells), hesperetin 7-O-beta-D-glucopyranoside (57 microg/g fr. wt of cells), and hesperetin 7-O-[6-O-(alpha-L-rhamnopyranosyl)]-beta-D-glucopyranoside (beta-rutinoside, hesperidin, 13 microg/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 beta-gentiobioside and beta-rutinoside. On the other hand, cultured I. batatas cells converted hesperetin into hesperetin 3'-O-beta-D-glucopyranoside (60 microg/g fr. wt of cells), hesperetin 5-O-beta-D-glucopyranoside (23 microg/g fr. wt of cells), and hesperetin 7-O-beta-D-glucopyranoside (110 microg/g fr. wt of cells).
Shimoda
Kei
K
Department of Pharmacology and Therapeutics, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan.
Hamada
Hatsuyuki
H
Hamada
Hiroki
H
D001711:Biotransformation; D018929:Cell Culture Techniques; D005052:Eucalyptus / Q000166:cytology / Q000378:metabolism*; D006031:Glycosylation; D006569:Hesperidin / Q000737:chemistry / Q000378:metabolism*; D027723:Ipomoea batatas / Q000166:cytology / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D012015:Reference Standards; D013997:Time Factors
D006569:Hesperidin; C013015:hesperetin