title: Development of a high speed counter-current chromatography system with Cu(II)-chiral ionic liquid complexes and hydroxypropyl-β-cyclodextrin as dual chiral selectors for enantioseparation of naringenin.
abstract: Cu(II) complexed amino acid ionic liquid, Cu(II)-[1-butyl-3-methylimidazolium][L-Pro] (Cu(II)-[BMIm][L-Pro]), was successfully adopted as chiral ligand to improve the enantioseparation efficiency in high speed counter-current chromatography (HSCCC). For the enantioseparation of intractable naringenin (NRG) racemic mixtures, Cu(II)-[BMIm][L-Pro] coupled with hydroxypropyl-β-cyclodextrin (HP-β-CD) was successfully applied as dual chiral selectors in HSCCC. The influence of important parameters, including the concentration of the chiral selectors, the pH value, and the temperature were investigated. Under optimal conditions, 4.5mg of (+)-NRG and 4.1mg of (-)-NRG were successfully separated from 10mg NRG racemic mixtures with the purity of 98%. The chiral recognition mechanism of dual chiral selectors was illuminated by the UV-vis and NMR spectra, suggesting that the enantioseparation was upon the difference of the thermodynamic stability of the quaternary complexes of Cu(II), [BMIm][L-Pro], HP-β-CD, and NRG. The results illustrated that the developed HSCCC system, based on the synergistic mechanism of Cu(II)-[BMIm][L-Pro] and HP-β-CD, exhibited better performance on enantioseparation and had great application potential in preparative chiral separation of natural products.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China.
authors.forename: Chao
authors.initials: C
authors.lastname: Han
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China.
authors.forename: Sisi
authors.initials: S
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China.
authors.forename: Lijuan
authors.initials: L
authors.lastname: Bai
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China. Electronic address: Luojg99@163.com.
authors.forename: Jianguang
authors.initials: J
authors.lastname: Luo
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, PR China. Electronic address: cpu_lykong@126.com.
authors.forename: Lingyi
authors.initials: L
authors.lastname: Kong
mesh_terms: D000073738:2-Hydroxypropyl-beta-cyclodextrin; D000596:Amino Acids / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D003377:Countercurrent Distribution; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification*; D052578:Ionic Liquids / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D044950:Flavanones; D052578:Ionic Liquids; D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D003300:Copper; C005273:naringenin
keywords: Chiral separation; High-speed counter-current chromatography; Hydroxypropyl-β-cyclodextrin; Naringenin; [1-Butyl-3-methylimidazolium][L-Pro]