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Enzymic reduction of [6]-gingerol, a major pungent principle of ginger, in the cell-free preparation of rat liver

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Authors
Surh, Young-Joon; Lee, Sang Sup
Issue Date
1994
Citation
Life Sciences, Vol.54 No.19, pp.PL321-PL326
Keywords
[6]-GINGEROLXENOBIOTIC KETONESTEREOSPECIFIC REDUCTION OF GINGEROL
Abstract
A reductive metabolism of S-(+)-[6]-gingerol [1-(4'-hydroxy-3'-methoxyphenyl)-5-hydroxydecan-3-one], the major pungent principle of ginger, was investigated in vitro with phenobarbital-induced rat liver 10,000 x g supernatant containing the NADPH-generating system. The ethyl acetate-extractable products were isolated and two metabolites were identified as diastereomers of [6]-gingerdiol by gas chromatography/mass spectrometry. The ratio of two isomers formed in die above reaction was about 1:5, suggesting the stereospecific reduction of S-(+)-[6]-gingerol by carbonyl reductase activity present in the postmitochondrial supernatant fraction of rat liver. The enzymic reduction of S-(+)-[61-gingerol thus introduces the second asymmetric carbon center in the molecule with concomitant production of S, S- and R, S-isomers of [6]-gingerdiol in different proportions. This stereospecific reduction of [6]-gingerol may be relevant to the clinical use of the compound.
ISSN
0024-3205
URI
https://hdl.handle.net/10371/172817
DOI
https://doi.org/10.1016/0024-3205(94)00602-4
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Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
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