Comprehensive investigation into the interconversion of C-2 diastereomers of naringin
Hongliang Yao1,2, Weiwei Su1,2, Linhuo Lin1
1Guangdong Engineering and Technology Research Center for Quality and Efficacy Re-evaluation of Post-marketed TCM, Guangdong Key Laboratory of Plant Resources, School of Life Sciences, Sun Yat-sen University, Guangzhou, China.
Abstract:
Naringin is a flavanone that widely presents on daily diet and traditional medicinal materials. The ratios of naringin C-2 diastereomers are found different in reported samples, thus suspiciously leading to various functions. In this study, we measured the interconversion of C-2 diastereomers intensively with ultimate high-performance liquid chromatography and circular dichroism spectra. We examined the diastereomeric naringins in fresh citrus fruit, Huajuhong decoction pieces, and naringin tablet; evaluated the impact of tablet production procedures in factory; and monitored the rapid racemization in incubation. The results not only confirmed that enzyme, temperature, and pH condition could influence the interconversion but also demonstrated that diverse ratios of diastereomers showed limited influence on metabolic behaviors of naringin in the blood, which consequently cause comparable bioactivities. This study could provide comprehensive understanding of diastereomeric interconversion and provide useful reference for drug development.
More Related Videos
Related Concept Videos
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
2° Amines to N-Nitrosamines: Reaction with NaNO2
SN2 Reaction: Kinetics
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
Steps in Outbreak Investigation
SN2 Reaction: Mechanism
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
SN2 Reaction: Transition State
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...


