Enzymic reduction of [6]-gingerol, a major pungent principle of ginger, in the cell-free preparation of rat liver.
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 the 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-(+)-[6]-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.
Surh
Y J
YJ
Department of Epidemiology and Public Health, Yale University School of Medicine, New Haven, CT 06520-8034.
Lee
S S
SS
D000818:Animals; D002396:Catechols; D002474:Cell-Free System; D002855:Chromatography, Thin Layer; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D008099:Liver / Q000187:drug effects / Q000378:metabolism*; D008297:Male; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010634:Phenobarbital / Q000494:pharmacology; D010946:Plants, Medicinal; D051381:Rats; D017207:Rats, Sprague-Dawley; D017365:Spices
D002396:Catechols; D005233:Fatty Alcohols; C007845:gingerol; D010634:Phenobarbital