Evaluating the enantioselective capability of a cellulose tris(3,5-dimethylphenyl carbamate)-based stationary phase towards 5,7,2'-trihydroxyflavanone

In this study, an evaluation of the enantioselective of a chiral flavanone with 2-OH substitution (5,7,2- trihydroxyflavanone) on ring C was studied by high performance liquid chromatography using the cellulose tris(3,5- dimethylphenyl carbamate)-based stationary phase with n-hexane and iso-propanol doped with 0.1% (v/v) trifluoroacetic acid as a mobile phase.
Nội dung trích xuất từ tài liệu:
Evaluating the enantioselective capability of a cellulose tris(3,5-dimethylphenyl carbamate)-based stationary phase towards 5,7,2-trihydroxyflavanoneCite this paper: Vietnam J. Chem., 2023, 61(S2), 149-154 Research ArticleDOI: 10.1002/vjch.202300193 Evaluating the enantioselective capability of a cellulose tris(3,5-dimethylphenyl carbamate)-based stationary phase towards 5,7,2-trihydroxyflavanone Nguyen Khanh Hung1,2, Nguyen Tuan Thanh1,2, Nguyen Thi Thuy Luyen1,2,4, Nguyen Huy Du1,2,3*1 Faculty of Chemistry, University of Science, 227 Nguyen Van Cu Road, District 5, Ho Chi Minh City 70000, Viet Nam2 Vietnam National University of Ho Chi Minh City, Vo Truong Toan Road, Linh Trung Ward, Thu Duc City, Ho Chi Minh City 70000, Viet Nam3 Central Laboratory of Analysis, University of Science, 227 Nguyen Van Cu Road, District 5, Ho Chi Minh City 70000, Viet Nam 4 Faculty of Geology, University of Science, 227 Nguyen Van Cu Road, District 5, Ho Chi Minh City 70000, Viet Nam Submitted June 6, 2023; Revised July 30, 2023; Accepted August 22, 2023Abstract In this study, an evaluation of the enantioselective of a chiral flavanone with 2-OH substitution (5,7,2-trihydroxyflavanone) on ring C was studied by high performance liquid chromatography using the cellulose tris(3,5-dimethylphenyl carbamate)-based stationary phase with n-hexane and iso-propanol doped with 0.1% (v/v) trifluoroaceticacid as a mobile phase. Column temperature and mobile phase composition were investigated in the assessment of thechiral separation by considering the enantiomeric resolution factor (R s). Also, the absolute configurations of singleenantiomers were determined by measuring CD spectra based on the exciton-coupling method. The results pointed outthat the 2-hydroxy group was capable of advancing the enantioselective of flavanones on the cellulose tris(3,5-dimethylphenyl carbamate)-based stationary phase when the column temperature was higher than 30 oC and the mobilephase was of 10% iso-propanol doped with 0.1% (v/v) TFA in n-hexane. The absolute configuration determination showedthat the enantiomer with the 2S configuration was the first eluted and, consequently, the elution order of the enantiomersof 5,7,2-trihydroxyflavanone at optimal conditions was in contrast to 5,7,4-trihydroxyflavanone and 5,7-dihydroxyflavanone. The 2-OH substitution on the phenyl moiety appears to be capable of inducing or altering thestrength of inter-and intramolecular interactions when the chiral selectors are immobilized on the silica stationary phase. Keywords. Chiral separation, 5,7,2-trihydroxyflavanone, enantioselective, HPLC.1. INTRODUCTION based stationary phase is one of the most common chiral stationary phases (CSPs) used to separateAmong the classes of flavanoids, flavanones are effectively enantiomers from racemate of organicconsidered as Citrus flavonoids due to their dominant compounds.[5] This CSPs has the ability of resolvingcontent in Citrus fruits.[1,2] All flavanoids have a various flavanone with different substituents on C-chemical structure based on a fusion of chroman-4- ring. Currently, the biological activities of ()5,7,2-one moiety (ring A and C) with C2-aryl group (ring trihydroxyflavanone (2OH-TFVN) and its analoguesB). Therefore, flavanones present a unique structural have been established and the synthetic route can onlyfeature with a single chiral carbon center. yield a racemate of 2-OH-TFVN.[6-9] However, theTrihydroxyflavanone (TFVN), which is one of HPLC method based on Cellulose tris(3,5-subclasses of flavanones[2] has been shown to have dimethylphenyl carbamate) CSPs are not available tomore remarkable biological activities than their separate the single enantiomers of 5,7,2-flavanone nuclei such as regulating hyperglycaemia, trihydroxyflavanone (2OH-TFVN) efficientlythyroid dysfunction and lipid peroxidation in alloxan- whereas 4-OH-TFVN was easily separable into itsinduced diabetic mice.[3,4] two enantiomers.[10,11] Cellulose tris(3,5-dimethylphenyl carbamate)- As a result, this study was synthesized and149 Wiley Online Library © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH ...