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Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP-HPLC and using Cyclodextrins in a Novel Way.
Phytochem Anal. 2017 May; 28(3):151-158.PA

Abstract

INTRODUCTION

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 KF for 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.

CONCLUSION

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.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Matencio A
Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
Bermejo-Gimeno MJ
Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
García-Carmona F
Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.
López-Nicolás JM
Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Murcia, Campus de Espinardo, 30071, Murcia, Spain.

MeSH

AcetatesChromatography, High Pressure LiquidChromatography, Reverse-PhaseCyclodextrinsCyclopentanesHydrogen-Ion ConcentrationMolecular Docking SimulationOxylipinsReproducibility of ResultsStereoisomerismTemperaturebeta-Cyclodextrins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27910224

Citation

Matencio, Adrián, et al. "Separating and Identifying the Four Stereoisomers of Methyl Jasmonate By RP-HPLC and Using Cyclodextrins in a Novel Way." Phytochemical Analysis : PCA, vol. 28, no. 3, 2017, pp. 151-158.
Matencio A, Bermejo-Gimeno MJ, García-Carmona F, et al. Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP-HPLC and using Cyclodextrins in a Novel Way. Phytochem Anal. 2017;28(3):151-158.
Matencio, A., Bermejo-Gimeno, M. J., García-Carmona, F., & López-Nicolás, J. M. (2017). Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP-HPLC and using Cyclodextrins in a Novel Way. Phytochemical Analysis : PCA, 28(3), 151-158. https://doi.org/10.1002/pca.2654
Matencio A, et al. Separating and Identifying the Four Stereoisomers of Methyl Jasmonate By RP-HPLC and Using Cyclodextrins in a Novel Way. Phytochem Anal. 2017;28(3):151-158. PubMed PMID: 27910224.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP-HPLC and using Cyclodextrins in a Novel Way. AU - Matencio,Adrián, AU - Bermejo-Gimeno,Mario J, AU - García-Carmona,Francisco, AU - López-Nicolás,José Manuel, Y1 - 2016/12/02/ PY - 2016/08/02/received PY - 2016/09/21/revised PY - 2016/09/25/accepted PY - 2016/12/3/pubmed PY - 2017/8/9/medline PY - 2016/12/3/entrez KW - RP-HPLC KW - cyclodextrin KW - docking KW - enantioseparation KW - methyl jasmonate SP - 151 EP - 158 JF - Phytochemical analysis : PCA JO - Phytochem Anal VL - 28 IS - 3 N2 - INTRODUCTION: 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 KF for 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. CONCLUSION: 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. SN - 1099-1565 UR - https://www.unboundmedicine.com/medline/citation/27910224/Separating_and_Identifying_the_Four_Stereoisomers_of_Methyl_Jasmonate_by_RP_HPLC_and_using_Cyclodextrins_in_a_Novel_Way_ DB - PRIME DP - Unbound Medicine ER -