Dataset Information

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

ABSTRACT: Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in Citrus reticulata 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 (R/S) 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 Citrus reticulata 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.

SUBMITTER: Jiang B

PROVIDER: S-EPMC9867467 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Publications

Chiral Separation, Configuration Confirmation and Bioactivity Determination of the Stereoisomers of Hesperidin and Narirutin in <i>Citrus reticulata</i> Blanco.

Jiang Bingtong B Cao Sirong S Zhang Jiayu J Wang Zhaokun Z

Molecules (Basel, Switzerland) 20230115 2

Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in <i>Citrus reticulata</i> 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 ab ...[more]

PMID: 36677930

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Project description:BackgroundCitrus reticulata Blanco 'Orah' is one of the most widely grown citrus varieties in southern China. It has been proven that microbial and organic manure fertilization improve the yields and appearances of 'Orah' fruits. However, details regarding the mechanisms underlying the effects of combined fertilization on the agronomic traits and rhizosphere bacterial community of plants still need to be elucidated.ResultsThis study compared the rhizosphere bacterial community and carotenoids of 'Orah' with (WYT group) and without (WYCK group) combined fertilization in a local orchard in Wuming town from Nanning, Guangxi, China. The WYT group was sprayed with 50 ml Strongreen and 250 g of Yumeiren five times while WYCK group did not sprayed. Combined fertilization increased fruit weight and the Citrus color index (CCI) significantly (p < 0.05). By 16s rRNA sequencing, 7,126 operational taxonomic units (OTU) were obtained. A higher Shannon index was observed in the WYT group compared to that in the WYCK group. Comparison between the two groups showed that Pseudomonas was enriched in the WYT group with LDA (log10) score of 4.32, and Cyanobacteria was enriched in the WYCK group with LDA (log10) score of -4.11. At the family level, Phyllobacteriaceae (abundance mean: 0.0046 in WYCK vs. 0.0073 in WYT) was significantly abundant in the WYT group, whereas Thermosporothrix (abundance mean: 0.00053 in WYCK vs. 0.0019 in WYT) and Sphingobium (abundance mean: 0.00053 in WYCK vs. 0.0013 in WYT) were significantly abundant in the WYCK group. A total of 51 carotenoid components were tested by UPLC-MS/MS. In the pulp tissues, 37 carotenoid components were decreased in the WYT group compared to those in the WYCK group. In fruit skin, 24 significantly different components (7 downregulated and 17 upregulated) were identified in WYT compared to those in WYCK. Correlation analysis revealed that the network between OTUs and carotenoids contained seven carotenoid components and four OTUs. Four OTUs, strain TRA3-20 (a eubacterium), Roseiflexus, OPB35, and Fictibacillus correlated to carotenoid accumulation regulation in fruit skin.ConclusionsThis study demonstrates the impact of the fertilization on soil microorganisms and carotenoid components. It constructs the regulatory network contained four OTUs for seven carotenoid components, providing evidence on precise fertilization in Orah.

Dataset Information

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

Publications

Chiral Separation, Configuration Confirmation and Bioactivity Determination of the Stereoisomers of Hesperidin and Narirutin in <i>Citrus reticulata</i> Blanco.

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