Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana.
The biotransformation of raspberry ketone and zingerone were individually investigated using cultured cells of Phytolacca americana. In addition to (2S)-4-(4-hydroxyphenyl)-2-butanol (2%), (2S)-4-(3,4-dihydroxyphenyl)-2-butanol (5%), 4-[4-(beta-d-glucopyranosyloxy)phenyl]-2-butanone (19%), 4-[(3S)-3-hydroxybutyl]phenyl-beta-d-glucopyranoside (23%), and (2S)-4-(4-hydroxyphenyl)but-2-yl-beta-d-glucopyranoside (20%), two biotransformation products, i.e., 2-hydroxy-4-[(3S)-3-hydroxybutyl]phenyl-beta-d-glucopyranoside (12%) and 2-hydroxy-5-[(3S)-3-hydroxybutyl]phenyl-beta-d-glucopyranoside (11%), were isolated from suspension cells after incubation with raspberry ketone for three days. On the other hand, two compounds, i.e., (2S)-4-(4-hydroxy-3-methoxyphenyl)but-2-yl-beta-d-glucopyranoside (17%) and (2S)-2-(beta-d-glucopyranosyloxy)-4-[4-(beta-d-glucopyranosyloxy)-3-methoxyphenyl]butane (16%), together with (2S)-4-(4-hydroxy-3-methoxyphenyl)-2-butanol (15%), 4-[4-(beta-d-glucopyranosyloxy)-3-methoxyphenyl]-2-butanone (21%), and 4-[(3S)-3-hydroxybutyl]-2-methoxyphenyl-beta-d-glucopyranoside (24%) were obtained upon addition of zingerone. Cultured cells of P. americana can reduce, and regioselectively hydroxylate and glucosylate, these food ingredients to their beta-glycosides.
Shimoda
Kei
K
Department of Pharmacology and Therapeutics, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan.
Harada
Toshio
T
Hamada
Hatsuyuki
H
Nakajima
Nobuyoshi
N
Hamada
Hiroki
H
D001711:Biotransformation; D002074:Butanones / Q000378:metabolism*; D002460:Cell Line; D002478:Cells, Cultured; D005421:Flavoring Agents / Q000378:metabolism; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D029604:Phytolacca americana / Q000166:cytology / Q000378:metabolism*
D002074:Butanones; D005421:Flavoring Agents; C013738:zingerone; D006139:Guaiacol; C035522:raspberry ketone