Development and validation of a RP-UHPLC-ESI-MS/MS method for the chiral separation and determination of flavanone, naringenin and hesperetin enantiomers

Baranowska, Irena; Hejniak, Judyta; Magiera, Sylwia

doi:10.1016/j.talanta.2016.06.020

Cited by 29 publications

(11 citation statements)

References 28 publications

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“…For instance, compound 31 had a [M+H] + peak at m/z 303.0860, and the secondary MS included m/z 219.0653, 177.0547, 171.0552, and 153.0184 fragment ions. Combined with the literature and MS fragment information [14], compound 31 was confirmed as hesperetin, whose fragmentation pattern is shown in Figure 4b. Similarly, compounds 39 and 55 generated [M+H] + peaks at m/z 287.0912 and 301.1069 in positive ion mode, respectively.…”

Section: Resultsmentioning

confidence: 83%

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Zheng

Liu

Chao

et al. 2020

J of Separation Science

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To systematically identify the lipophilic constituents of Citri Reticulatae Pericarpium from different cultivars, supercritical CO2 fluid extraction and ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry were integrated for the component analysis of 18 batches of Citri Reticulatae Pericarpium from 12 cultivars for the first time. A total of 57 components from the supercritical CO2 fluid extracts were demonstrably or tentatively identified by the obtained parent peaks, fragment peaks, and retention times. In total, two flavonoids, six organic acids, nine coumarins, three aldehydes, seven esters, three terpenes, one limonoid, and five other compounds were detected for the first time; notably, coumarin components have not yet been reported in Citri Reticulatae Pericarpium. Furthermore, the extract constituents differed between cultivars. In particular, organic acids were more abundant in Citrus reticulata “Chachi” than in other cultivars, and pterostilbene was exclusively found in Citrus reticulata “Yichangju”. The results showed that a greater variety of compounds in Citri Reticulatae Pericarpium could be extracted by supercritical CO2 fluid extraction and detected by ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry. This study provides a more scientific basis for further analysis of the pharmacological activity and quality of Citri Reticulatae Pericarpium components from different cultivars.

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Section: Resultsmentioning

confidence: 83%

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Zheng

Liu

Chao

et al. 2020

J of Separation Science

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“…It was a method described by Baranowska I. et al. with modifications in the form of using crude SFE M. sativa extract, mixing the sample during hydrolysis, and evaporation of a solvent at a defined temperature (Figure ).…”

Section: Methodsmentioning

confidence: 99%

“…The hydrolysis method was carried out according to Baranowska et al. with modifications. In this method, crude SFE plant extract and non‐acidified distilled water were used.…”

Section: Methodsmentioning

confidence: 99%

“…After this, the samples were cooled, and evaporated to dryness at the temperature not exceeding 40 • C. The dry residue was dissolved in methanol (150 μL). It was a method described by Baranowska I. et al [32] with modifications in the form of using crude SFE M. sativa extract, mixing the sample during hydrolysis, and evaporation of a solvent at a defined temperature ( Figure 2).…”

Section: Acid Hydrolysismentioning

confidence: 99%

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Isolation and determination of saponin hydrolysis products from Medicago sativa using supercritical fluid extraction, solid‐phase extraction and liquid chromatography with evaporative light scattering detection

Kiełbasa

Krakowska

Rafińska

et al. 2018

J of Separation Science

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Saponins are widespread secondary metabolites with various beneficial properties: fungicidal, antibacterial, antiviral, and anticancer. Alfalfa saponin molecules contain mainly: medicagenic acid, hederagenin, bayogenin, and soyasapogenol B. Structural diversity of saponins makes their determination in Medicago sativa extracts very difficult. The most popular determination technique is high‐performance liquid chromatography applied with evaporative light scattering detection. Qualitative and quantitative analysis of sapogenins from Medicago sativa by high‐performance liquid chromatography with evaporative light scattering detection required hydrolysis and purification of extracts obtained by supercritical fluid extraction. Hydrolysis of saponins with concentrated hydrochloric acid provided high concentration of medicagenic acid. In the purification process, satisfactory results were obtained for solid‐phase extraction using octadecyl. Recoveries were from 71 to 99% with a standard deviation from 2 to 8. Hydrolysis with concentrated hydrochloric acid was the only method that allowed identification of all four analyzed sapogenins. Moreover, it is characterized by a short time of preparation, simplicity of execution, a small amount of the sample and solvents. The hydrolysis and purification methods coupled with high‐performance liquid chromatography and evaporative light scattering detection can be successfully used for qualitative and quantitative analysis of the main saponins present in Medicago sativa plant extracts obtained by supercritical fluid extraction.

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“…Therefore, the development of enantioselective methods is important for pharmacodynamics, pharmacokinetics, toxicological, and quality control of many kinds of substances . For this purpose, techniques like gas and liquid chromatography dominated for many years, but capillary electrophoresis (CE) has proven to be a great choice . CE has many advantages and one can cite no organic solvent consumption for analysis in the case of aqueous electrophoresis, instrumental simplicity, and high efficiencies.…”

Section: Introductionmentioning

confidence: 99%

Computational contribution to the electrophoretic enantiomer separation mechanism and migration order using modified β‐cyclodextrins

et al. 2017

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Capillary electrophoresis (CE) is an extremely effective technique in many kinds of separations, including separation of enantiomers. Some additional techniques may be necessary to determine the enantiomer migration order (EMO) and also the mechanism involved in chiral recognition. This paper reports the development and optimization of a CE method for enantioseparation of racemic mixture of both R- and S-stereoisomers of tramadol (TRM) with a computational contribution for the EMO determination and the responsible mechanisms for chiral distinction. Parameters such as composition and concentration of background electrolyte (BGE) and type and concentration of cyclodextrins (CD) were evaluated. For calculations, a sequential methodology was used, resorting to semiempirical Parametric Model 3 (PM3) followed by calculations accomplished using density functional theory. The best results were obtained with sulfated-β-CD (s-β-CD) and carboxymethyl-β-cyclodextrin (cm-β-CD) as chiral selector. Calculations show that the inclusion of TRM is not a probable process due to the shape of the TRM molecule and the size CDs cavities. Therefore, the chiral recognition process occurs by the formation of association complexes between modified β-CD and groups of TRM molecules. The structural analysis of the fragments of complexes at a pH of 10 and a thermodynamic analysis of the complexes' formation process allows determining the EMO. Comparing results obtained experimentally and computationally, it seems that the developed method is adequate for separation of TRM enantiomers and the computational methodology is also adequate to get a sense of the system at a molecular level.

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Development and validation of a RP-UHPLC-ESI-MS/MS method for the chiral separation and determination of flavanone, naringenin and hesperetin enantiomers

Cited by 29 publications

References 28 publications

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Isolation and determination of saponin hydrolysis products from Medicago sativa using supercritical fluid extraction, solid‐phase extraction and liquid chromatography with evaporative light scattering detection

Computational contribution to the electrophoretic enantiomer separation mechanism and migration order using modified β‐cyclodextrins

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Development and validation of a RP-UHPLC-ESI-MS/MS method for the chiral separation and determination of flavanone, naringenin and hesperetin enantiomers

Cited by 29 publications

References 28 publications

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO2 fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO2 fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Isolation and determination of saponin hydrolysis products from Medicago sativa using supercritical fluid extraction, solid‐phase extraction and liquid chromatography with evaporative light scattering detection

Computational contribution to the electrophoretic enantiomer separation mechanism and migration order using modified β‐cyclodextrins

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Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry

Identification of lipophilic components in Citri Reticulatae Pericarpium cultivars by supercritical CO₂ fluid extraction with ultra‐high‐performance liquid chromatography–Q Exactive Orbitrap tandem mass spectrometry