title: Stereoisomeric separation of some flavanones using highly succinate-substituted α-cyclosophoro-octadecaoses as chiral additives in capillary electrophoresis.
abstract: α-Cyclosophoro-octadecaoses (α-C18), produced by Rhodobacter sphaeroides, are mostly homogeneous in size with 18 glucose units per ring as the predominant form. α-C18s are linked by β-(1→4)-linkages and one α-(1→6)-linkage and are also known to be highly substituted by acetyl (0-2 per mol) and/or succinoyl groups (1-7 per mol). We isolated and purified α-C18 and successfully used it in capillary electrophoresis (CE) as a chiral additive for the separation of five flavanones and flavanone-7-O-glycosides, including naringenin, hesperetin, eriodictyol, homoeriodictyol, isosakuranetin, and hesperidin. Throughout the CE experiment with unsubstituted α-C18 (uα-C18) obtained after alkaline treatment of the isolated α-C18, we found that successful chiral separation critically depends on the presence of succinate substituents attached to α-C18 in CE, suggesting that succinoylation of α-C18 is decisive for effective stereoisomeric separation.
authors.affiliation: Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, 1 Hwayang-dong Gwangjin-gu, Seoul 143-701, South Korea.
authors.forename: Chanho
authors.initials: C
authors.lastname: Kwon
authors.forename: Seunho
authors.initials: S
authors.lastname: Jung
mesh_terms: D019075:Electrophoresis, Capillary / Q000379:methods*; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D013237:Stereoisomerism; D019802:Succinic Acid / Q000737:chemistry*; D013696:Temperature; D047391:alpha-Cyclodextrins / Q000737:chemistry*
chemical_list: D044950:Flavanones; D047391:alpha-Cyclodextrins; D019802:Succinic Acid