Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE

Abstract

Succinoglycan, a shinorhizobial exopolysaccharide produced by Shinorhizobium meliloti, is composed of an octasaccharide subunit. S. meliloti produces both high-molecular-weight and low-molecular-weight (M(r)<10 000) succinoglycans that consisted of monomer, dimer, or trimer of an octasaccharide unit. We isolated and purified the monomer among low-molecular-weight succinoglycans and used this microbial linear octasaccharide as a novel chiral additive for enantiomeric separation of some flavanones such as homoeriodictyol, hesperetin, naringenin, and isosakuranetin in CE. Throughout the present investigation, we firstly used noncyclic oligosaccharides for the chiral separation of flavanones. We also found that successful enantioseparation of four flavanones depends on the presence of succinate substituents of the linear monomeric octasaccharide in CE, suggesting that succinylation of succinoglycan monomer is decisive for the effective enantiomeric separation.

Solubility Enhancement of Salicylic Acid by Complexation with Succinoglycan Monomers Isolated from Sinorhizobium meliloti

“…11,12 The successful enantio separation of flavonoids using the succinoglycan monomer is based on the different interactions between the monomer and the R or S configuration of chiral flavonoids. Also, the structural property of the succinoglycan dimers was investigated.…”

Hydrophobic Interactions of Succinoglycan Dimers Isolated from Sinorhizobium meliloti with Hydrophobic Fluorescence Probes, 8-anilino-1-naphthalenesulfonate and 6-p-toluidino-2-naphthalenesulfonate

“…Monomers of succinoglycan have been isolated and investigated as chiral additives in capillary electrophoresis (CE) for the chiral separation of some flavonoids. 8,9 The effect of enantioseparation is known to be dependent on the succinate moiety of the monomer structure. Also, flavonoid enantioseparations using succinoglycan monomer show that the monomer may directly interact with flavonoids produced by the host plant.…”

Solubilization of Pyrimethamine, Antibacterial Drug, by Low-Molecular-Weight Succinoglycan Dimers Isolated from Shinorhizobium meliloti

“…12,14 Depending on the number of succinyl moieties in their structure, the monomers are purified into M1, M2, and M3 fractions, and the dimers are purified into D1, D2, D3, and D4 fractions. 12,15,16 In addition, we previously …”