title: Enantiomeric resolution of (±)-licarin A by high-performance liquid-chromatography using a chiral stationary phase.
abstract: (±)-Licarin A (1), a neolignan obtained by the oxidative coupling reaction of isoeugenol, had in this study its enantiomers resolved. A novel, quick and efficient enantiomeric resolution of 1 was directly performed by chiral high-performance liquid chromatography (HPLC-PDA) protocol (CHIRALPACK(®) AD column; 9:1 (v/v) n-hexane:2-propanol; 1.0 mL/min). This method provided a chromatogram profile with a well-resolved peak separation. After isolation of each enantiomer with ee>99.9%, they were analysed in a polarimeter. Compound 2, which showed a retention time (t(r)) of 12.13 min, was the (+)-enantiomer and compound 3 (t(r)=18.90 min) was the (-)-enantiomer.
authors.affiliation: Grupo de Pesquisas em Produtos Naturais, Núcleo de Ciências Exatas e Tecnológicas, Universidade de Franca, Avenida Dr. Armando Salles de Oliveira, 2001, 14404-600 Franca, SP, Brazil.
authors.forename: Ana Carolina
authors.initials: AC
authors.lastname: Pereira
authors.forename: Lizandra G
authors.initials: LG
authors.lastname: Magalhães
authors.forename: Ana Helena
authors.initials: AH
authors.lastname: Januário
authors.forename: Patrícia M
authors.initials: PM
authors.lastname: Pauletti
authors.forename: Wilson Roberto
authors.initials: WR
authors.lastname: Cunha
authors.forename: Jairo Kenupp
authors.initials: JK
authors.lastname: Bastos
authors.forename: Dhammika N P
authors.initials: DN
authors.lastname: Nanayakkara
authors.forename: Márcio Luis A e
authors.initials: ML
authors.lastname: Silva
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D000688:Amylose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005054:Eugenol / Q000031:analogs & derivatives / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification; D048448:Phenylcarbamates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006586:Hexanes; D017705:Lignans; D048448:Phenylcarbamates; C496603:dehydrodiisoeugenol; C432503:licarin A; C080033:Chiralpak AD; C026385:n-hexane; D005054:Eugenol; D000688:Amylose; D019840:2-Propanol