Author(s): Shimoda K, Harada T, Hamada H, Nakajima N, Hamada H
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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.
This article was published in Phytochemistry
and referenced in Medicinal Chemistry