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Stereoselective Metabolism of Naringenin Enantiomers in Rat Liver Microsomes: CYP3A Dependency and Species Specificity
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DOI：10.1021/acs.jafc.6c06013.png)
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Abstract
En 中文
Naringenin, a chiral flavonoid, contains a chiral center and exists as (R)- and (S)-enantiomers, yet its enantiomer-specific metabolism has remained largely unexplored. Herein, high-purity (R)- and (S)-naringenin were isolated via chiral semipreparative chromatography, and their racemization kinetics under near-physiological conditions were systematically quantified. Incubation with rat liver microsomes revealed pronounced stereoselectivity: the (R)-enantiomer was metabolized significantly faster than the (S)-enantiomer. Mechanistic studies identified the CYP3A subfamily as the key mediator of this stereoselectivity. Notably, this stereoselective profile was completely absent in human liver microsomes, uncovering a critical species difference. These findings provide direct evidence for enzyme-level chiral recognition in naringenin metabolism and highlight species-specific disparities in its metabolic pathway.
Keywords:
Anatomy
Metabolism
Molecular structure
Peptides and proteins
Rodent models
naringenin enantiomers
liver microsomes
racemization
stereoselective metabolism
cytochromes P450
Journal
IF:
6.2
Papers:
4.5W
Citations:
15.3W
Organization
Cited Papers