title: Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana.
abstract: 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.
authors.affiliation: Department of Pharmacology and Therapeutics, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Shimoda
authors.forename: Toshio
authors.initials: T
authors.lastname: Harada
authors.forename: Hatsuyuki
authors.initials: H
authors.lastname: Hamada
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Nakajima
authors.forename: Hiroki
authors.initials: H
authors.lastname: Hamada
mesh_terms: 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*
chemical_list: D002074:Butanones; D005421:Flavoring Agents; C013738:zingerone; D006139:Guaiacol; C035522:raspberry ketone