Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana

• Published in: Phytochemistry (Oxford) 2007-02, Vol.68 (4), p.487-492
• Main Authors: Shimoda, Kei, Harada, Toshio, Hamada, Hatsuyuki, Nakajima, Nobuyoshi, Hamada, Hiroki
• Format: Article
• Language: English
• Subjects: aromatic compounds; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Biotransformation; butanol; Butanones - metabolism; Cell Line; Cells, Cultured; cultured cells; Cultured plant cells; Di-β-Glucoside; ethers; Flavoring Agents - metabolism; Fundamental and applied biological sciences. Psychology; glucopyranoside; Glycosides; glycosylation; Guaiacol - analogs & derivatives; Guaiacol - metabolism; hydroxylation; ketones; Kinetics; Magnetic Resonance Spectroscopy; Methods. Procedures. Technologies; Phytolacca americana; Phytolacca americana - cytology; Phytolacca americana - metabolism; Phytolaccaceae; raspberries; Raspberry ketone; reduction; Rubus idaeus; Zingerone; Zingiber officinale; β-Glucoside
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2006.11.030

Four biotransformation products 8, 9, 13, and 14, together with eight known products, were isolated from the cultured cells of Phytolacca americana following administration of raspberry ketone ( 1) and zongerone ( 2). The biotransformation of raspberry ketone and zingerone were individually investigated using cultured cells of Phytolacca americana. In addition to (2 S)-4-(4-hydroxyphenyl)-2-butanol (2%), (2 S)-4-(3,4-dihydroxyphenyl)-2-butanol (5%), 4-[4-(β- d-glucopyranosyloxy)phenyl]-2-butanone (19%), 4-[(3 S)-3-hydroxybutyl]phenyl-β- d-glucopyranoside (23%), and (2 S)-4-(4-hydroxyphenyl)but-2-yl-β- d-glucopyranoside (20%), two biotransformation products, i.e., 2-hydroxy-4-[(3 S)-3-hydroxybutyl]phenyl-β- d-glucopyranoside (12%) and 2-hydroxy-5-[(3 S)-3-hydroxybutyl]phenyl-β- d-glucopyranoside (11%), were isolated from suspension cells after incubation with raspberry ketone for three days. On the other hand, two compounds, i.e., (2 S)-4-(4-hydroxy-3-methoxyphenyl)but-2-yl-β- d-glucopyranoside (17%) and (2 S)-2-(β- d-glucopyranosyloxy)-4-[4-(β- d-glucopyranosyloxy)-3-methoxyphenyl]butane (16%), together with (2 S)-4-(4-hydroxy-3-methoxyphenyl)-2-butanol (15%), 4-[4-(β- d-glucopyranosyloxy)-3-methoxyphenyl]-2-butanone (21%), and 4-[(3 S)-3-hydroxybutyl]-2-methoxyphenyl-β- 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 β-glycosides.