title: Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP-HPLC and using Cyclodextrins in a Novel Way.
abstract: BACKGROUND
  Several authors have reported on the different bioactivities of methyl jasmonate (MeJA) stereoisomers. However, no simple, precise and cheap method for separating and identifying them using reversed-phase high performance liquid chromatography (RP-HPLC) has been developed.
  
  
  OBJECTIVE
  (1) To create a simple, precise and cheap method for separating and identifying the four stereoisomers present in commercial racemic mixtures of MeJA and (2) to identify the four stereoisomers using molecular docking techniques and coinjection. Materials and Methods - RP-HPLC using a 250 mm C18 column and different proportions of cyclodextrins (CDs) and organic solvents was applied to a commercial sample of racemic MeJA.
  
  
  RESULTS
  The results show that the best conditions for separating the MeJA stereoisomers are: 20% methanol in the mobile phase, a temperature of 45 °C and a 16 mM concentration of methyl-β-cyclodextrin (M-β-CD). A simple C18 250 mm column and a flow rate of 1.25 mL/min were used. The reduction in the retention time of MeJA observed when M-β-CD is added to the mobile phases was used to determine the complexation constants of the guest/CD complex and compared with the obtained when other CDs were used. The KFfor M-β-CD (117.49 ± 5.9 1/M) was obtained with a 1:1 stoichiometry. The four stereoisomers were identified by molecular docking techniques and coinjection of a commercially available rosemary essential oil.
  
  
  CONCLUSIONS
  The new method identified and classified the four stereoisomers of MeJA in the following ordination: (-)epiMeJA, (-)MeJA; (+)MeJA and (+)epiMeJA. These results could be used to improve the elicitation of cell cultures with only the best isomer. Copyright © 2016 John Wiley & Sons, Ltd.
authors.affiliation: Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
authors.forename: Adrián
authors.initials: A
authors.lastname: Matencio
authors.affiliation: Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
authors.forename: Mario J
authors.initials: MJ
authors.lastname: Bermejo-Gimeno
authors.affiliation: Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: García-Carmona
authors.affiliation: Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
authors.forename: José Manuel
authors.initials: JM
authors.lastname: López-Nicolás
mesh_terms: D000085:Acetates / Q000032:analysis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D003517:Cyclopentanes / Q000032:analysis* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D062105:Molecular Docking Simulation; D054883:Oxylipins / Q000032:analysis* / Q000737:chemistry*; D015203:Reproducibility of Results; D013237:Stereoisomerism; D013696:Temperature; D047392:beta-Cyclodextrins / Q000737:chemistry
chemical_list: D000085:Acetates; D003505:Cyclodextrins; D003517:Cyclopentanes; D054883:Oxylipins; D047392:beta-Cyclodextrins; C108732:methyl-beta-cyclodextrin; C072239:methyl jasmonate
keywords: RP-HPLC; cyclodextrin; docking; enantioseparation; methyl jasmonate