Molecular Modeling Studies on the Chiral Separation of (±)-Catechins by Mono-succinyl-β-cyclodextrin

Chiral separation is a subject of great interest in the development, use, and action of pharmaceutical agents. Chiral pharmaceutical compounds typically have different pharmacological and toxicological properties, and therefore the quantitative chiral composition of these compounds should be determined. 1 The catechin discussed in this work belongs to the group of polyphenols, which are represented by the class of flavan-3-ols. The flavan-3-ols show notable physiological effects, including antioxidant, antimicrobial, and anticarcinogenic activities.

[1]  A. Puglisi,et al.  The 6-derivative of beta-cyclodextrin with succinic acid: a new chiral selector for CD-EKC. , 2005, Journal of pharmaceutical and biomedical analysis.

[2]  T. Lóránd,et al.  Chiral separation of bioactive cyclic Mannich ketones by HPLC and CE using cellulose derivatives and cyclodextrins as chiral selectors. , 2002, Journal of biochemical and biophysical methods.

[3]  D. Armstrong,et al.  Separation of drug stereoisomers by the formation of beta-cyclodextrin inclusion complexes. , 1986, Science.

[4]  Seunho Jung,et al.  Aqueous Solubility Enhancement of Some Flavones by Complexation with Cyclodextrins , 2008 .

[5]  Seunho Jung,et al.  Preference Prediction for the Stable Inclusion Complexes between Cyclodextrins and Monocyclic Insoluble Chemicals Based on Monte Carlo Docking Simulations , 2006 .

[6]  A. Torrens,et al.  Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes. , 1999, Chirality.

[7]  Y. Michotte,et al.  Influence of methanol on the enantioresolution of antihistamines with carboxymethyl‐β‐cyclodextrin in capillary electrophoresis , 2004, Electrophoresis.

[8]  M. Nielen Chiral separation of basic drugs using cyclodextrin-modified capillary zone electrophoresis , 1993 .

[9]  S. Kodama,et al.  Direct enantioseparation of catechin and epicatechin in tea drinks by 6‐O‐α‐D‐glucosyl‐β‐cyclodextrin‐modified micellar electrokinetic chromatography , 2004 .

[10]  Jungwon Choi,et al.  Chiral Separation and Discrimination of Catechin by Microbial Cyclic β-(1→3),(1→6)-glucans Isolated from Bradyrhizobium japonicum , 2007 .

[11]  C. García-Ruiz,et al.  Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis , 2003, Electrophoresis.

[12]  G. Scriba,et al.  Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis using carboxymethyl‐β‐cyclodextrin and succinyl‐β‐cyclodextrin: Influence of the amino acid sequence, nature of the cyclodextrin and pH , 2001, Electrophoresis.

[13]  O. Trapp,et al.  Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers. , 2006, Analytical chemistry.

[14]  L Wang,et al.  Molecular dynamics and free-energy calculations applied to affinity maturation in antibody 48G7. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[15]  R. Galensa,et al.  (-)-Catechin in cocoa and chocolate: occurrence and analysis of an atypical flavan-3-ol enantiomer. , 2007, Molecules.

[16]  J. Vivanco,et al.  Enantiomeric-Dependent Phytotoxic and Antimicrobial Activity of (±)-Catechin. A Rhizosecreted Racemic Mixture from Spotted Knapweed1 , 2002, Plant Physiology.

[17]  R. Gotti,et al.  Analysis of catechins in Theobroma cacao beans by cyclodextrin-modified micellar electrokinetic chromatography. , 2006, Journal of chromatography. A.

[18]  G. Williamson,et al.  (+)-Catechin is more bioavailable than (−)-catechin: Relevance to the bioavailability of catechin from cocoa , 2006, Free radical research.

[19]  G. Blaschke,et al.  Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis , 1996 .

[20]  Y. Ishihama,et al.  Cyclodextrin-modified micellar electrokinetic chromatography: Separation of hydrophobic and enantiomeric compounds , 1993 .

[21]  D. Osguthorpe,et al.  Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase‐trimethoprim, a drug‐receptor system , 1988, Proteins.

[22]  G. Scuseria,et al.  Gaussian 03, Revision E.01. , 2007 .

[23]  M. Serafini,et al.  Plasma antioxidants from chocolate , 2003, Nature.

[24]  V. Davankov The nature of chiral recognition: Is it a three‐point interaction? , 1997 .

[25]  E. Bosch,et al.  Determination of dissociation constants of flavonoids by capillary electrophoresis , 2005, Electrophoresis.

[26]  Chung S. Yang,et al.  Cancer chemopreventive activity and bioavailability of tea and tea polyphenols. , 2003, Mutation research.

[27]  J. Hamilton,et al.  Crystal structure of an inclusion complex of .beta.-cyclodextrin with racemic fenoprofen: direct evidence for chiral recognition , 1988 .

[28]  P. Walter,et al.  Stereospecific effects of (+)- and (-)-catechin on glycogen metabolism in isolated rat hepatocytes. , 1983, Biochimica et biophysica acta.

[29]  C. García-Ruiz,et al.  Separation of etodolac enantiomers by capillary electrophoresis. Validation and application of the chiral method to the analysis of commercial formulations , 2005, Electrophoresis.

[30]  R. Galensa,et al.  Enantioseparation of catechin and epicatechin in plant food by chiral capillary electrophoresis , 2007 .