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Enzymic reduction of [6]-gingerol, a major pungent principle of ginger, in the cell-free preparation of rat liver
Cited 15 time in
Web of Science
Cited 23 time in Scopus
- Authors
- Issue Date
- 1994
- Publisher
- Elsevier BV
- Citation
- Life Sciences, Vol.54 No.19, pp.PL321-PL326
- 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
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