Ordered mesoporous silica functionalized with beta-cyclodextrin derivative for stereoisomer separation of flavanones and flavanone glycosides by nano-liquid chromatography and capillary electrochromatography
Authors
Silva, Mariana; Marina Alegre, María Luisa; Pérez Quintanilla, Damián; Morante Zarcero, Sonia; Sierra, Isabel; [et al.]Identifiers
Permanent link (URI): http://hdl.handle.net/10017/48160DOI: 10.1016/j.chroma.2017.02.012
ISSN: 00219673
Date
2017-03-25Affiliation
Universidad de Alcalá. Departamento de Química Analítica, Química Física e Ingeniería QuímicaBibliographic citation
Journal of Chromatography A, 2017, v. 1490, p. 166-176
Keywords
Nano-liquid chromatography
Capillary electrochromatography
Ordered mesoporous silica
Chiral separations
beta-Cyclodextrin stationary phase
Flavanones
Project
info:eu-repo/grantAgreement/CAM//S2013%2FABI-3028/ES/Estrategias avanzadas para la mejora y el control de la calidad y la seguridad de los alimentos/AVANSECAL-CM
info:eu-repo/grantAgreement/MINECO//CTQ2013-48740-P/ES/METODOLOGIAS AVANZADAS PARA ANALISIS QUIRAL MEDIANTE TECNICAS MICROSEPARATIVAS. BUSQUEDA DE BIOMARCADORES EN SISTEMAS ENANTIOSELECTIVOS/
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
© Elsevier
Access rights
info:eu-repo/semantics/openAccess
Abstract
In this paper a chiral stationary phase (CSP) was prepared by the immobilization of a beta-CD derivative (3,5-dimethylphenylcarbamoylated beta-CD) onto the surface of amino-functionalized spherical ordered mesoporous silica (denoted as SM) via a urea linkage using the Staudinger reaction. The CSP was packed into fused silica capillaries 100 mu m I.D. and evaluated by means of nano-liquid chromatography (nano-LC) and capillary electrochromatography (CEC) using model compounds for the enantio- and the diastereomeric separation. The compounds flavanone, 2'-hydroxyflavanone, 4'-hydroxyflavanone, 6hydroxyflavanone, 4'-methoxyflavanone, 7-methoxyfiavanone, hesperetin, hesperidin, naringenin, and naringin were studied using reversed and polar organic elution modes. Baseline stereoisomer resolution and good results in terms of peak efficiency and short analysis time of all studied flavonoids and flavanones glycosides were achieved in reversed phase mode, using as mobile phase a mixture of MeOH/H2O, 10 mM ammonium acetate pH 4.5 at different ratios. For the polar organic mode using 100% of MeOH as mobile phase, the CSP showed better performances and the baseline chiral separation of several studied compounds occurred in an analysis time of less than 10 min. Good results were also achieved by CEC employing two different mobile phases. The use of MeOH/H2O, 5 mM ammonium acetate buffer pH 6.0 (90/10, v/v) was very effective for the chiral resolution of flavanone and its methoxy and hydroxy derivatives. (C) 2017 Elsevier B.V. All rights reserved.
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