title: Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column.
abstract: A pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-5-O-beta-d-glucopyranoside (1a, 1b), was successfully separated by RP-C(18) high-performance liquid chromatography from Balanophora involucrata Hook. f. Some other compounds, including a pair of flavanone enantiomers, (2R)- and (2S)-eriodictyol (2a, 2b), and a pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-7-O-beta-d-glucopyranoside(3a, 3b), were separated by capillary electrophoresis from the same plant. The absolute configurations at C-2 of 1a and 1b were determined based on their circular dichroism spectra. Enzymatic hydrolysis of 1a and 1b by beta-d-glucosidase afforded (2R)- and (2S)-eriodictyol, respectively, which were used as the authentic standards for co-elution to determine the migration order of the enantiomers, 2a and 2b. We also report the first example of identifying the migration order of 2a and 2b and resolving the separation of 3a and 3b by capillary electrophoresis. In addition, 1a was unambiguously characterized for the first time by NMR spectra.
authors.affiliation: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China.
authors.forename: Jianyu
authors.initials: J
authors.lastname: Pan
authors.forename: Si
authors.initials: S
authors.lastname: Zhang
authors.forename: Liushui
authors.initials: L
authors.lastname: Yan
authors.forename: Jiandong
authors.initials: J
authors.lastname: Tai
authors.forename: Qiang
authors.initials: Q
authors.lastname: Xiao
authors.forename: Kun
authors.initials: K
authors.lastname: Zou
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhou
authors.forename: Jun
authors.initials: J
authors.lastname: Wu
mesh_terms: D031111:Balanophoraceae / Q000737:chemistry*; D002021:Buffers; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D044950:Flavanones / Q000302:isolation & purification*; D005960:Glucosides / Q000302:isolation & purification*; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism
chemical_list: D002021:Buffers; D003505:Cyclodextrins; D044950:Flavanones; D005960:Glucosides; C007619:eriodictyol; C028610:flavanone