title: Ordered mesoporous silica functionalized with β-cyclodextrin derivative for stereoisomer separation of flavanones and flavanone glycosides by nano-liquid chromatography and capillary electrochromatography.
abstract: In this paper a chiral stationary phase (CSP) was prepared by the immobilization of a β-CD derivative (3,5-dimethylphenylcarbamoylated β-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 100μm 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, 6-hydroxyflavanone, 4'-methoxyflavanone, 7-methoxyflavanone, 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, 10mM 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 10min. Good results were also achieved by CEC employing two different mobile phases. The use of MeOH/H2O, 5mM 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.
authors.affiliation: Departamento de Tecnología Química y Energética, Tecnología Química y Ambiental, Tecnología Mecánica y Química Analítica, E.S.C.E.T, Universidad Rey Juan Carlos, C/Tulipán s/n, 28933 Móstoles, Madrid, Spain; Institute of Chemical Methodologies, Italian National Council of Research, Area della Ricerca di Roma, Via Salaria Km 29, 300-00015 Monterotondo Scalo, Rome, Italy.
authors.forename: Mariana
authors.initials: M
authors.lastname: Silva
authors.affiliation: Departamento de Tecnología Química y Energética, Tecnología Química y Ambiental, Tecnología Mecánica y Química Analítica, E.S.C.E.T, Universidad Rey Juan Carlos, C/Tulipán s/n, 28933 Móstoles, Madrid, Spain.
authors.forename: Damián
authors.initials: D
authors.lastname: Pérez-Quintanilla
authors.affiliation: Departamento de Tecnología Química y Energética, Tecnología Química y Ambiental, Tecnología Mecánica y Química Analítica, E.S.C.E.T, Universidad Rey Juan Carlos, C/Tulipán s/n, 28933 Móstoles, Madrid, Spain.
authors.forename: Sonia
authors.initials: S
authors.lastname: Morante-Zarcero
authors.affiliation: Departamento de Tecnología Química y Energética, Tecnología Química y Ambiental, Tecnología Mecánica y Química Analítica, E.S.C.E.T, Universidad Rey Juan Carlos, C/Tulipán s/n, 28933 Móstoles, Madrid, Spain.
authors.forename: Isabel
authors.initials: I
authors.lastname: Sierra
authors.affiliation: Departamento de Química Analítica, Química Física e Ingeniería Química, Facultad de Biología, Ciencias Ambientales y Química, Universidad de Alcalá, Ctra. Madrid-Barcelona Km 33.600, 28871 Alcalá de Henares, Madrid, Spain.
authors.forename: María Luisa
authors.initials: ML
authors.lastname: Marina
authors.affiliation: Institute of Chemical Methodologies, Italian National Council of Research, Area della Ricerca di Roma, Via Salaria Km 29, 300-00015 Monterotondo Scalo, Rome, Italy.
authors.forename: Zeineb
authors.initials: Z
authors.lastname: Aturki
authors.affiliation: Institute of Chemical Methodologies, Italian National Council of Research, Area della Ricerca di Roma, Via Salaria Km 29, 300-00015 Monterotondo Scalo, Rome, Italy. Electronic address: salvatore.fanali@imc.cnr.it.
authors.forename: Salvatore
authors.initials: S
authors.lastname: Fanali
mesh_terms: D053801:Capillary Electrochromatography / Q000379:methods*; D044950:Flavanones / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D036103:Nanotechnology; D012822:Silicon Dioxide / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D044950:Flavanones; D006027:Glycosides; D047392:beta-Cyclodextrins; D012822:Silicon Dioxide
keywords: Capillary electrochromatography; Chiral separations; Flavanones; Nano-liquid chromatography; Ordered mesoporous silica; β-Cyclodextrin stationary phase