486
Views
13
CrossRef citations to date
0
Altmetric
Regular Papers

CYCLODEXTRINS AND THEIR DERIVATIVES IN THE RESOLUTION OF CHIRAL NATURAL PRODUCTS: A REVIEW

, , , , , , , & show all
Pages 194-215 | Published online: 01 May 2012

REFERENCES

  • Alan , L. H. Natural products in drug discovery . Drug Discovery Today 2008 , 13 ( 19–20 ), 894 – 901 .
  • Cragg , G. M. ; Newman , D. J. ; Snader , K. M. Natural products in drug discovery and development . J. Nat. Prod. 1997 , 60 ( 1 ), 52 – 60 .
  • Newman , D. J. ; Cragg , G. M. ; Snader , K. M. Natural products as sources of new drugs over the period 1981–2002 . J. Nat. Prod. 2003 , 66 ( 7 ), 1022 – 1037 .
  • Newman , D. J. ; Cragg , G. M. Natural products as sources of new drugs over the last 25 years . J. Nat. Prod. 2007 , 70 ( 3 ), 461 – 477 .
  • Wu , L. J. Chemistry of Natural Medicines ; People's Medical Publishing House Press : Beijing , China , 2008 ; 5 – 17 .
  • Dewick , P. M. Medicinal Natural Products: A Biosythethic Approach, , 2nd ed. Wiley : New York , 2002 ; pp. 7 – 30 .
  • Zhao , J. L. ; Shan , T. S. ; Mou , Y. ; Zhou , L. G. Plant-derived bioactive compounds produced by endophytic fungi . Mini Rev. Med. Chem. 2011 , 11 ( 2 ), 159 – 168 .
  • Pezzuto , J. M. Plant-derived anticancer agents . Biochem. Pharmacol. 1997 , 53 ( 2 ), 121 – 133 .
  • Liang , Q. J. ; Zhang , S. ; Zheng , Y. B. ; Wang , C. ; Wang , Y. C. Effects of anti-tumor drugs harringtonine on the proliferation of Hela cell and their relationship with cenpB gene . Acta Biophysica Sinica 2005 , 21 ( 1 ), 26 – 31 .
  • Kay , C. D. The future of flavonoid research . Br. J. Nutr. 2010 , 104 ( S3 ), 91 – 95 .
  • Quideau , S. ; Deffieux , D. ; Doaut-Casassus , C. ; Pouyséqu , L. Plant polyphenols: Chemical properties, biological activities, and synthesis . Angew. Chem., Int. Ed. Engl. 2011 , 50 ( 3 ), 586 – 621 .
  • Caffieri , S. ; Lisa , F. D. ; Boesani , F. ; Facco , M. ; Semenzato , G. ; Acqua , F. D. ; Canton , M. The mitochondrial effects of novel apoptogenic molecules generated by psoralen photolysis as a crucial mechanism in PUVA therapy . Blood 2007 , 109 ( 11 ), 4988 – 4991 .
  • Singh , G. B. ; Singh , S. ; Bani , S. ; Gupta , B. D. ; Banerjee , S. K. Anti-inflammatory effect of oleanolic acid in rats and mice . J. Pharm. Pharmacol. 1992 , 44 ( 5 ), 456 – 458 .
  • Liu , J. Oleanolic acid and ursolic acid: research perspectives . J. Ethnopharmacol. 2005 , 11 ( 1–2 ), 92 – 94 .
  • Yamamoto , N. ; Ejiri , M. ; Mizuno , S. Biogenic peptides and their potential use . Curr. Pharm. Des. 2003 , 9 ( 16 ), 1345 – 1355 .
  • Siddiqui , B. S. ; Khatoon , N. ; Begum , S. ; Durrani , S. A. Two new triterpenoid isomers from Nerium oleander leaves . Nat. Prod. Res. 2009 , 23 ( 17 ), 1603 – 1608 .
  • Parish , C. A. ; Smith , S. K. ; Calati , K. ; Zink , D. ; Wilson , K. ; Roemer , T. ; Jiang , B. ; Xu , D. ; Bills , G. ; Platas , G. ; Peláez , F. ; Díez , M. T. ; Tsou , N. ; McKeown , A. E. ; Ball , R. G. ; Powles , M. A. ; Yeung , L. ; Liberator , P. ; Harris , G. Isolation and structure elucidation of parnafungins, antifungal natural products that inhibit mRNA polyadenylation . J. Am. Chem. Soc. 2008 , 130 ( 22 ), 7060 – 7066 .
  • Malhotra , A. ; Krilov , L. R. Viral croup . Ped. Rev. 2001 , 22 ( 1 ), 5 – 12 .
  • Nguyen , L. A. ; He , H. ; Chuong , P. H. Chiral drugs: An overview . Int. J. Biomed. Sci. 2006 , 2 ( 2 ), 85 – 100 .
  • Engstrom , A. ; Wan , H. ; Andersson , P. E. ; Josefsson , B. Determination of chiral reagent purity by capillary electrophoresis . J. Chromatogr. A 1995 , 715 ( 1 ), 151 – 158 .
  • Brooks , D. P. ; Koster , F. P. ; Albrightson , C. R. ; William , F. H. ; Moore , M. L. ; Stassen , F. L. ; Schmidt , D. B. ; Kinter , L. B. Vasopressin receptor antagonism in rhesus monkey and man: Stereochemical requirements . Eur. J. Pharmacol. 1989 , 160 ( 1 ), 159 – 162 .
  • Stalcup , A. M. Chiral separations . Annu. Rev. Anal. Chem. 2010 , 3 ( 1 ), 341 – 363 .
  • Subramanian , G. Chiral Separation Techniques: A Practical Approach, , 3rd ed. ; Wiley : New York , 2006 ; pp. 160 – 200 .
  • Schneiderman , E. ; Stalcupm , A. M. Cyclodextrins: A versatile tool in separation science . J. Chromatogr. B 2000 , 745 ( 1 ), 83 – 102 .
  • Loftsson , T. ; Duchêne , D. Cyclodextrin and their pharmaceutical applications . Int. J. Pharm. 2007 , 39 ( 1–2 ), 1 – 11 .
  • Challa , R. ; Ahuja , A. ; Ali , J. ; Khar , R. K. Cyclodextrins in drug delivery: An updated review. AAPS Pharm. Sci. Tech. 2005, 6(2), 329–357.
  • Stella , V. J. ; He , Q. Cyclodextrins . Toxicol. Pathol. 2008 , 36 ( 1 ), 30 – 42 .
  • Adamovics , J. A. Chromatographic Analysis of Pharmaceuticals, , 2nd ed. ; Marcel Dekker : New York , 1997 ; pp. 57 – 240 .
  • Kuhn , R. ; Hoffstetter-Kuhn , S. Chiral separations by capillary electrophoresis . Chromatographia 1992 , 34 ( 9–10 ), 505 – 512 .
  • Bylka , W. ; Matlawska , I. ; Pilewski , N. A. Natural flavonoids as antimicrobial agents . J. Am. Nutr. Assoc. 2004 , 7 ( 2 ), 24 – 31 .
  • Erich , G. The Science of Flavonoids ; Springer : Berlin , 2002 ; 1 – 17 .
  • Zhang , P. C. Chemistry of Flavonoids ; Chemical Industry Press : Beijing , China , 2009 ; pp. 4 – 20 .
  • Yáńez , J. A. ; Andrews , P. K. ; Davies , N. M. Methods of analysis and separation of chiral flavonoids . J. Chromatogr. B 2007 , 848 ( 2 ), 159 – 181 .
  • Asztemborska , M. ; Miskiewicz , M. ; Sybilska , D. Separation of some chiral flavanones by micellar electrokinetic chromatography . Electrophoresis 2003 , 24 ( 15 ), 2527 – 2531 .
  • Gel-Moreto , N. ; Streich , R. ; Galensa , R. Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice . J. Chromatogr. A 2001 , 925 ( 1–2 ), 279 – 289 .
  • Krause , M. ; Galensa , R. Optical resolution of flavanones by high-performance liquid chromatography on various chiral stationary phases . J. Chromatogr. A 1990 , 514 ( 2 ), 147 – 159 .
  • Wistuba , D. ; Trapp , O. ; Moreto , G. ; Galensa , R. ; Schurig , V. Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers . Anal. Chem. 2006 , 78 ( 10 ), 3424 – 3433 .
  • Ahn , E. M. ; Nakamura , N. ; Akao , T. ; Komatsu , K. ; Qui , M. H. ; Hattori , M. Prenylated flavonoids from Moghania philippinesis . Phytochemistry 2003 , 64 ( 8 ), 1389 – 1394 .
  • Lin , C. H. ; Fang , W. R. ; Kuo , C. M. ; Chang , W. Y. ; Liu , Y. C. ; Lin , W. Y. ; Wu , J. C. ; Lin , C. E. Chiral separation of hydroxyflavanones in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors . J. Chromatogr. A 2008 , 1118 ( 2 ), 301 – 307 .
  • Aturki , Z. ; Sinibaldi , M. Separation of diastereisomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl ether-β-cyclodextrin as the selector . J. Sep. Sci. 2003 , 26 ( 9–10 ), 844 – 850 .
  • Carbonnier , B. ; Janus , L. ; Zukowski , J. High performance liquid chromatographic enantioseparation of flavanones on 2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin copolymer coated silica phase . J. Chromatogr. Sci. 2005 , 43 ( 7 ), 358 – 361 .
  • Kim , H. ; Choi , Y. ; Lim , J. ; Paik , S. ; Jung , S. Chiral separation of catechin by capillary electrophoresis using mono-, di-, tri-succinyl-β-cyclodextrin as chiral selectors . Chirality 2009 , 21 ( 10 ), 937 – 942 .
  • Abidi , S. L. Chiral-phase high-performance liquid chromatography of rotenoid racemates . J. Chromatogr. A 1987 , 404 ( 1 ), 133 – 143 .
  • Wang , F. P. Chemistry of Alkaloids ; Chemical Industry Press : Beijing , China , 2008 ; 10 – 15 .
  • Cordell , G. A. ; Quinn-Bettie , M. L. ; Farnsworth , N. R. The potential of alkaloids in drug discovery . Phytother. Res. 2001 , 15 ( 3 ), 183 – 205 .
  • Vansal , S. S. ; Feller , D. R. Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes . Biochem. Pharmacol. 1999 , 58 ( 5 ), 807 – 810 .
  • Snopek , J. ; Ivan , J. ; Smolková-Keulemansová , E. Use of cyclodextrins in isotachophoresis: IV. The influence of cyclodextrins on the chiral resolution of ephedrine alkaloid enantiomers . J. Chromatogr. A 1988 , 438 , 211 – 218 .
  • Fanali , S. ; Flieger , M. ; Steinerova , N. ; Nardi , A. Use of cyclodextrins for the enantioselective separation of ergot alkaloids by capillary zone electrophoresis . Electrophoresis 1992 , 13 ( 1–2 ), 39 – 43 .
  • Frach , K. ; Blaschke , G. Separation of ergot alkaloids and their epimers and determination in sclerotia by capillary electrophoresis . J. Chromatogr. A 1998 , 808 ( 1–2 ), 247 – 252 .
  • Maruszak , W. ; Trojanowicz , M. ; Margasińska , M. ; Engelhardt , H. Application of carboxymethyl-β-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters . J. Chromatogr. A 2001 , 926 ( 2 ), 327 – 336 .
  • Avula , B. ; Khan , A. Separation and determination of ephedrine enantiomers and synephrine by high performance capillary electrophoresis in dietary supplements . Chromatographia 2004 , 59 ( 1–2 ), 71 – 77 .
  • Jiang , T. F. ; Lv , Z. H. ; Wang , Y. H. Chiral separation of ephedrine alkaloids from Ephedra sinica extract and its medicinal preparation using cyclodextrin-modified capillary zone electrophoresis. J. Anal. Chem. 2007, 62(1), 85–89.
  • Tsimachidis , D. ; Cesla , P. ; Hájek , T. ; Theodoridis , G. ; Janderam , P. Capillary electrophoretic chiral separation of cinchona alkaloids using a cyclodextrin selector . J. Sep. Sci. 2008 , 31 ( 6–7 ), 1130 – 1136 .
  • Stalcup , A. M. ; Faulkner , J. R. ; Tang , Y. ; Armstrong , D. W. ; Levy , L. W. ; Regalado , E. Determination of the enantiomeric purity of scopolamine isolated from plant extract using achiral/chiral coupled column chromatography . Biomed. Chromatogr. 1991 , 5 ( 1 ), 3 – 7 .
  • Wedig , M. ; Holzgrabe , U. Enantioseparation of tropane alkaloids by means of anionic cyclodextrin-modified capillary electrophoresis . Electrophoresis 1999 , 20 ( 7 ), 1555 – 1560 .
  • Zwenger , S. ; Basu , C. Plants terpenoids, applications and future potentials . Biotechnol. Mol. Biol. Rev. 2008 , 3 ( 1 ), 1 – 7 .
  • Kościelski , T. ; Sybilska , D. ; Jurczak , J. Separation of α- and β-pinene into enantiomers in gas-liquid chromatography systems via a cyclodextrin inclusion complexes . J. Chromatogr. 1983 , 280 ( 1 ), 131 – 134 .
  • Quattrini , F. ; Biressi , G. ; Juza , M. ; Mazzotti , M. ; Fuganti , C. ; Morbidelli , M. Enantiomer separation of α-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases . J. Chromatogr. A 1999 , 865 ( 1–2 ), 201 – 210 .
  • Gahm , K. H. ; Chang , L. W. ; Armstrong , D. W. Chiral separation of monoterpenes using mixtures of sulfated β-cyclodextrins and α-cyclodextrin as chiral additives in the reversed-polarity capillary electrophoresis mode . J. Chromatogr. A 1997 , 759 ( 1–2 ), 149 – 155 .
  • Neugebauer , W. ; Schreier , P. Identification and enantiodifferentiation of C13 norisoprneoid degradation products of glycosidically bound 3-hydroxy-α-ioinol from stinging nettle . J. Agric. Food. Chem. 1995 , 43 ( 6 ), 1647 – 1653 .
  • Wang , Y. ; Zhao , M. Chiral separation of enantiomers of a plant growth regulator, abscisic acid, by capillary electrophoresis with cyclodextrin additives . J. Liq. Chromatogr. Relat. Technol. 2003 , 26 ( 11 ), 1709 – 1717 .
  • Khrimian , A.; Cosse A. A. ; Crook , D. J. Absolute configuration of 7-epi-sesquithujene . J. Nat. Prod. 2011 , 74 ( 6 ), 1414 – 1420 .
  • Huang , K. ; Armstrong , D. W. GC-MS analysis of crocetane, phytane and some of their stereoisomers using cyclodextrin-based stationary phases . Org. Geochem. 2009 , 40 ( 2 ), 283 – 286 .
  • Diagone , C. A. ; Ogawa , C. A. ; Langas , F. M. Evaluation of cyclodextrins as chiral selectors in the separation of selected monoterpenes by capillary liquid chromatography and capillary electrophoresis . J. Liq. Chromatogr. Relat. Technol. 2003 , 26 ( 4 ), 505 – 516 .
  • Singh , G. ; Kapoor , I. P. S. ; Pandey , S. K. ; Singh , U. K. ; Singh , R. K. Studies on essential oils: Part 10, Antibacterial activity of volatile oils of some spices . Phytother. Res. 2002 , 16 ( 7 ), 680 – 682 .
  • Gerald , G. ; Martin , G. S. Chiral Separations, Methods and Protocols ; Humana Press : New York , 2004 ; 61 – 66 .
  • Bicchi , C. ; Amato , A. D. ; Rubiolo , P. Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oils, aroma and flavour fields . J. Chromatogr. A 1999 , 843 ( 1–2 ), 99 – 121 .
  • Chanotiya , C. S. ; Yadav , A. Enantiomeric composition of (3 R)-(-)- and (3S)-(+)-linalool in various essential oils of Indian origin by enantioselective capillary gas chromatography-flame ionization and mass spectrometry detection methods . Nat. Prod. Commun. 2009 , 4 ( 4 ), 563 – 566 .
  • Noge , K. ; Shimizu , N. ; Becerra , J. X. (R)-(-)-Linalyl acetate and (S)-(-)-germacrene D from the leaves of Mexican Bursera linanoe . Nat. Prod. Commun. 2010 , 5 ( 3 ), 351 – 354 .
  • Hardt , I. ; König , W. A. Preparative enantiomer separation with modified cyclodextrins as chiral stationary phases . J. Chromatogr. A 1994 , 666 ( 1–2 ), 611 – 615 .
  • Bicchi , C. ; Amato , A. D. ; Manzin , V. ; Galli , A. ; Galli , M. Cyclodextrin derivatives in GC separation of racemic mixtures of volatiles—Part XII: Thick-film wide-bore columns for enantiomer GC preparation . J. High Res. Chromatogr. 1997 , 20 ( 9 ), 493 – 498 .
  • Bicchi , C. ; Artuffo , G. ; Amato , D. A. ; Galli , A. ; Galli , M. Cyclodextrin derivatives in the GC separation of racemic mixtures of volatile compounds: Part IV. J. High Res. Chromatogr. 1992, 15(10), 655–658.
  • Bicchi , C. ; Artuffo , G. ; Amato , D. A. ; Galli , A. ; Galli , M. Cyclodextrin derivatives in the GC separation of racemic mixtures of volatile compounds: Part V . J. High Res. Chromatogr. 1992 , 15 ( 11 ), 710 – 714 .
  • Bicchi , C. ; Artuffo , G. ; Amato , D. A. ; Galli , A. ; Galli , M. Cyclodextrin derivatives in the GC separation of racemic mixtures of volatile compounds: Part VI . J. High Res. Chromatogr. 1993 , 16 ( 4 ), 209 – 214 .
  • Schurig , V. Use of derivatized cyclodextrins as chiral selectors for the separation of enantiomers by gas chromatography . Ann. Pharm. Fr. 2010 , 68 ( 2 ), 82 – 98 .
  • Pályi , G. ; Zucchi , C. Progress in Biological Chirality ; Elsevier : Amsterdam , 2004 ; 221 – 230 .
  • Rizzi , A. M. ; Runge-Cladrowa , S. ; Jonsson , H. ; Osla , S. Enantiomeric resolution of derivatiized D, L-amino acids by high-performance liquid chromatography using a β-cyclodextrin chiral stationary phase . J. Chromatogr. A 1995 , 710 ( 2 ), 287 – 295 .
  • Chang , M. H. ; Tsai , C. F. ; Li , F. C. Enantiomeric separation of Dns-DL-amino acids by γ-cyclodextrin-modified micellar capillary electrophoresis . J. Agric. Food. Chem. 1998 , 46 ( 11 ), 4598 – 4603 .
  • Rizzi , A. M. ; Kremser , L. Enantioseparation of derivatized amino acids by capillary isoelectric focusing using cyclodextrin complexation . Electrophoresis 1999 , 20 ( 17 ), 3410 – 3416 .
  • Chen , S. The facile HPLC enantioresolution of amino acids, peptides on naphthylethylcarbamate-ß-cyclodextrin bonded phases using the acetonitrile-based mobile phase after their pre-column derivatization with phenyl isothiocyanate: Factors that affect the resolution . Amino Acids 2004 , 26 ( 3 ), 291 – 298 .
  • Cucinotta , V. ; Giuffrida , A. ; Grasso , G. ; Maccarrone , G. High selectivity in new chiral separations of dansyl amino acids by cyclodextrin derivatives in electrokinetic chromatography . J. Chromatogr. A. 2007 , 1155 ( 2 ), 172 – 179 .
  • Kitagawa , F. ; Otsuka , K. Recent progress in capillary electrophoretic analysis of amino acid enantiomers . J. Chromatogr. B 2011 , 879 ( 29 ), 3078 – 3095 .
  • Duquesne , S. ; Destoumieux-Garzón , D. ; Peduzzi , J. ; Rebuffat , S. Microcins, gene-encoded antibacterial peptides from enterobacteria . Nat. Prod. Rep. 2007 , 24 ( 4 ), 708 – 734 .
  • Sabbah , S. ; Scriba , G. K. E. Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis using carboxymeyl-β-cyclodextrin and succinyl-β-cyclodextrin: Influence of the amino acid sequence, nature of the cyclodextrin and pH . Electrophoresis 2001 , 22 ( 7 ), 1385 – 1393 .
  • Li , J. J. ; Waldron , C. K. Effect of surfactant concentration of the determination of trans, trans-muconic acid in urine by cationic micellar electrokinetic chromatography with thermo-optical absorbance detection . J. Liq. Chromatogr. Relat. Technol. 1999 , 22 ( 12 ), 1919 – 1933 .
  • Janini , G. M. ; Muschik , G. M. ; Issaq , H. J. Electrokinetic chromatography in suppressed elecro-osmotic flow environment: Use of a charged cyclodextrin for the separation of enantiomers and geometric isomers . Electrophoresis 1996 , 17 ( 10 ), 1575 – 1583 .
  • Skanchy , D. J. ; Wilson , R. ; Poh , T. ; Xie , G. H. ; Demarest , C. W. ; Stobauqh , J. F. Resolution of acylated dipeptide stereoisomer by capillary electrophoresis using sulfobutylether derivatized beta-cyclodextrin . Electrophoresis 1997 , 18 ( 6 ), 985 – 995 .
  • Verleysen , K. ; Sabah , S. ; Scriba , G. ; Sandra , P. Enantioseparation of aspartyl dipeptides by CE: Comparison between 18-crown-6-tetracarboxylic acid and carboxymethyl-β-cyclodextrin as chiral selector . Chromatographia 1999 , 49 ( 3–4 ), 215 – 218 .
  • Sanger-Van de Griend , C. E. Enantiomeric separation of glycyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors . Electrophoresis 1999 , 20 ( 17 ), 3147 – 3424 .
  • Sanger-Van de Griend , C. E. Enantiomeric separation of alanyl and leucyl dipeptides by capillary electrophoresis with cyclodextrins as chiral selectors . Electrophoresis 2000 , 21 ( 12 ), 2397 – 2404 .
  • Sabbah , S. ; Scriba , G. K. E. Influence of the structure of cyclodextrins and amino acid sequence of dipeptides and tripeptides on the pH-dependent reversal of the migration order in capillary electrophoresis . J. Chromatogr. A 2000 , 894 ( 1–2 ), 267 – 272 .
  • Sabbah , S. ; Scriba , G. K. E. Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis using carboxymethyl-β-cyclodextrin and succinyl-β-cyclodextrin: Influence of amino acid sequence, nature of the cyclodextrin and pH . Electrophoresis 2001 , 22 ( 7 ), 1385 – 1393 .
  • Cheng , Y. ; Bai , M. ; Wang , X. ; Ming , Y. ; You , J. Chiral separation of dipeptides by capillary electrophoresis. Chin. J. Chromatogr. 2006, 24(2), 188–191.
  • Sänger-van de Griend , C. E. ; Gröningsson , K. ; Arvidsson , T. Enantiomeric separation of a tertrapeptide with cyclodextrin extension of the model for chiral capillary electrophoresis by complex formation of enantiomer molecule with more than one chiral selector molecules . J. Chromatogr. A 1997 , 782 ( 2 ), 271 – 279 .
  • Chen , Y. ; Zhang , J. H. ; Zhang , L. ; Chen , G. N. Separation of dipeptides with two chiral centers using 2-hydroxypropyl-CD-modified MEKC . Electrophoresis 2010 , 31 ( 9 ), 1493 – 1497 .
  • Hearon , W. M. ; Macgreor , W. S. The naturally occurring lignans . Chem. Rev. 1995 , 55 ( 5 ), 957 – 1068 .
  • Thompson , L. U. ; Boucher , B. A. ; Cotterchio , M. ; Kreiger , N. ; Liu , Z. Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada . Nutr. Cancer 2007 , 59 ( 2 ), 176 – 184 .
  • Müller , U. ; Mrestani , Y. ; Neubert , R. ; Dräger , B. Chiral separation of the plant lignan matairesinol by capillary electrophoresis . Electrophoresis 2008 , 29 ( 17 ), 3582 – 3587 .
  • Xie , L. H. ; Ahn , E. M. ; Akao , T. ; Monem , A. A. ; Nakamura , N. ; Hattori , M. Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria . Chem. Pharm. Bull. 2003 , 51 ( 4 ), 378 – 384 .
  • Riveiro , M. E. ; De-Kimpe , N. ; Moglioni , A. ; Vázquez , R. ; Monczor , F. ; Shayo , C. ; Davio , C. Coumarins: Old compounds with novel promising therapeutic perspectives . Curr. Med. Chem. 2010 , 17 ( 13 ), 1325 – 1338 .
  • Armstrong , D. W. ; Chang , L. W. ; Chang , S. C. ; Wang , X. ; Ibrahim , H. ; Reid , G. R. ; Beesley , T. E. Comparison of the enantioselectivity of β-cyclodextrin vs heptakis-2, 3-O-dimethyl-β-cyclodextrin LC stationary phases . J. Liq. Chromatogr. Relat. Technol. 1997 , 20 ( 20 ), 3279 – 3282 .
  • Schumacher , D. D. ; Mitchell , C. R. ; Xiao , T. L. ; Rozhkov , X. R. ; Larock , R. C. ; Armstrong , D. W. Cyclodextrin-based liquid chromatographic enantiomeric separation of chiral dihydrofuraocoumarins, an emerging class of medicinal compounds . J. Chromatogr. A 2003 , 1011 ( 1–2 ), 37 – 47 .
  • Majid , E. ; Male , B. K. ; Tzeng , M. Y. ; Omamogho , O. J. ; Glennon , D. Y. ; Luong , J. H. T. Cyclodextrin-modified capillary electrophoresis for achiral and chiral separation of ergostane and lanostane compounds extracted from the fruiting body of Antrodia camphorata. Electrophoresis 2009 , 30 ( 11 ), 1967 – 1975 .
  • Mesplet , N. ; Tran , T. T. ; Morin , P. ; Francois , C. An original way to use a β-cyclodextrin-bonded silica stationary phase in electrochromatography application to the achiral separation of nucleobases and nucleosides . Chromatographia 2002 , 56 ( 1–2 ), 51 – 56 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.