HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines

Uchiyama, Nahoko; Kim, Ik Hwi; Kikura‐Hanajiri, Ruri; Kawahara, Nobuo; Konishi, Tenji; Goda, Yukihiro

doi:10.1016/j.jpba.2007.04.004

Cited by 22 publications

(20 citation statements)

References 12 publications

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“…From the structural point of view, hesperidin is a chiral compound, with the C2 position of the 2 methoxyphenol having two tautomeric forms: 2R and 2S [25,26]. Thus, the presence of two isomers of complex 1 was also expected and confirmed by NMR spectroscopy (Fig.…”

Section: Synthesis and Characterization Of Complex Cis-[ru(hesp)(phenmentioning

confidence: 68%

Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Oliveira

Daniel

Carlos

2013

Journal of Molecular Structure

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Section: Synthesis and Characterization Of Complex Cis-[ru(hesp)(phenmentioning

confidence: 68%

Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Oliveira

Daniel

Carlos

2013

Journal of Molecular Structure

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“…Different analytical techniques such as TLC, UV, HPLC, capillary electrophoresis have been employed for analysis of isoflavonoids over the past decades (Drašar and Moravcova 2004;Liu et al 2008;Zhou et al 2009). LC methods with UV detection have questionable specificity for distinguishing compounds of very similar structures as they often exhibit fairly similar UV absorption characteristics (Bilia et al 2001;Cao et al 2008;Dachtler et al 2001;Krause and Galensa 1991;Pietta et al 1991;Qi et al 2006;Rehwald et al 1994;Tian et al 2006;Uchiyama et al 2008;Wu and Thompson 2006;Zhou et al 2008Zhou et al , 2009. Also these methods are time consuming and labour-intensive.…”

Section: Lc-ms/ms Analysis Of Isoflavonoidsmentioning

confidence: 99%

Phytochemical analysis of isoflavonoids using liquid chromatography coupled with tandem mass spectrometry

et al. 2015

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Isoflavonoids are the biologically active secondary metabolites of plants that are being used for several health promoting and restoring effects mediated through different pathways. Isoflavonoids are structurally similar to estrogens due to which also known as phytoestrogens and have shown potent estrogenic and anti-estrogenic activity. Association with large biological activity lead to the need of rapid, sensitive and precise quantitation of different isoflavonoids in different plant extracts, food materials and biological matrices as the biological activities mainly depends on the quantities and nature of isoflavonoids present in them. The characterisation, standardisation and quantification of herbal extracts or food products require techniques that are highly selective, sensitive and also provide mass measurement precisions and structural information. Liquid chromatography with tandem mass spectroscopy has made it possible to analyse and characterize several constituents and their metabolites in a single run along with high selectivity and sensitivity. In this review, we have summarised the application of LC-MS/MS for the identification and quantification of isoflavonoids reported for various plant extracts and food products along with their general extraction procedures and factors affecting extraction providing a view towards the conditions used for their analysis. The most suitable and widely acceptable extraction solvent system for the isoflavonoids is methanol or ethanol in combination with water ranging from 40 to 60 % organic solvent based on the type of tissues and the isoflavonoids to be extracted by different extraction techniques. ESI ionization with Q-TOF MS was the most useful detection system for the characterisation and quantification of the diverse isoflavonoids with molecular insights.

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“…Gaffield and Caccamese reported that mainly (2 S )‐naringin existed in immature fruits, while the ratio of S to R configuration turned to nearly 1:1 after the ripeness, due to absence of chalcone isomerase . Apart from enzymatic influence, high temperature and pH environment also accelerated the transformation between these 2 diastereomers. Besides, Uchiyama et al reported that the relative ratios of naringin to its C‐2 epimer varied from 29.0% to 89.1% in commercial samples, indicating no regular rule in marketed samples.…”

Section: Introductionmentioning

confidence: 99%

“…The stereogenic center in C‐2 as well as chiralities of the sugars causes the discrimination of diastereomeric naringins. During these 2 decades, aiming at separation of both diastereomers, epimeric analytical methodologies are established with various techniques …”

Section: Introductionmentioning

confidence: 99%

“…Apart from enzymatic influence, high temperature and pH environment also accelerated the transformation between these 2 diastereomers. Besides, Uchiyama et al reported that the relative ratios of naringin to its C‐2 epimer varied from 29.0% to 89.1% in commercial samples, indicating no regular rule in marketed samples. Therefore, both inside and outside conditions played vital roles when quantifying the distribution of diastereomeric naringins.…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive investigation into the interconversion of C‐2 diastereomers of naringin

Yao

Lin

et al. 2018

Chirality

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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.

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HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines

Cited by 22 publications

References 12 publications

Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Phytochemical analysis of isoflavonoids using liquid chromatography coupled with tandem mass spectrometry

Comprehensive investigation into the interconversion of C‐2 diastereomers of naringin

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