Chiral Separation, Configuration Confirmation and Bioactivity Determination of the Stereoisomers of Hesperidin and Narirutin in Citrus reticulata Blanco

Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in Blanco. In the present study, a chiral HPLC-UV method with amylose tris(3,5-dimethylphenylcarbamate) as a stationary phase under a normal-phase mode was used to achieve the stereoselective separat...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-01, Vol.28 (2), p.873
Main Authors: Jiang, Bingtong, Cao, Sirong, Zhang, Jiayu, Wang, Zhaokun
Format: Article
Language:English
Subjects:
Absolute configuration
Amylose
anti-inflammatory activity
Anti-inflammatory agents
Biological activity
chiral separation
Chromatography
Chromatography, High Pressure Liquid
Circular dichroism
Citrus - chemistry
citrus peel
Citrus reticulata
Configurations
Density functional theory
Diastereoisomers
Dichroism
epimer composition
flavanone glycoside
Flavanones - chemistry
Flavonoids
Glycosides
Glycosides - chemistry
Herbal medicine
Hesperidin
Hesperidin - chemistry
High performance liquid chromatography
Inflammation
Liquid chromatography
Quality assessment
Separation
Stationary phase
Stereoisomerism
Stereoisomers
Stereoselectivity
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Summary:Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in Blanco. In the present study, a chiral HPLC-UV method with amylose tris(3,5-dimethylphenylcarbamate) as a stationary phase under a normal-phase mode was used to achieve the stereoselective separation of the C-2 diastereomers of hesperidin and narirutin simultaneously. The single epimer was then successfully prepared by applying semi-preparative chromatography, whose absolute configuration ( / ) was characterized by combining the experimental electronic circular dichroism (ECD) detection with time-dependent density functional theory (TDDFT) calculations. The epimer composition of these two chiral flavanone glycosides in Blanco was then determined, which was found to be slightly different in the herbs from different production regions. The anti-inflammatory activity of each prepared single epimer was further evaluated, and some differences between one pair of epimers of hesperidin and narirutin were observed, which suggested that the presence of different epimers should be considered in the quality evaluation and control of natural medicine.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28020873