Jasminum polyanthum Franch. as a natural source of (-)-methyl jasmonate: an alternative to the use of the synthetic standard.
BACKGROUND
Methyl jasmonate (MJ) contains two chiral centres at C-3 and C-7 in its chemical structure, which implies that it can exist in four possible stereoisomeric forms, namely (+)-MJ, (-)-MJ, (+)-epiMJ and (-)-epiMJ. The absolute configuration of the two side chains of MJ affects the biological activity associated with this compound.


OBJECTIVE
To isolate pure (-)-MJ from a natural source, Jasminum polyanthum Franch., with the intention of increasing the knowledge about its biological properties, including its effect on the biosynthesis of plant metabolites.


METHODS
The method used was based on steam distillation extraction (SDE) as an extraction technique followed by high-performance liquid chromatography (HPLC) as a purification procedure. The HPLC flow-rate as well as the number of fractions accumulated were optimised to achieve the concentration and purity required.


RESULTS
The employment of 0.3 mL/min as HPLC flow-rate and the accumulation of three HPLC fractions allowed the required enantiomeric purity (95%) and concentration (0.36 mg/L in each HPLC fraction) to efficiently obtain (-)-methyl jasmonate from Jasminum polyanthum Franch. to be achieved.


CONCLUSIONS
The approach proposed may enable the properties and effect of pure (-)-MJ on plant responses to be studied. The use of a natural source to obtain (-)-MJ is presented as an alternative to the enantioselective synthesis and enantiomeric resolution from the standard racaemic mixture.
Blanch
Gracia Patricia
GP
Instituto de Fermentaciones Industriales, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, Madrid.
Flores
Gema
G
Caja
Maria del Mar
Mdel M
Ruiz del Castillo
Maria Luisa
ML
D000085:Acetates / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003517:Cyclopentanes / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D035264:Flowers / Q000737:chemistry; D031660:Jasminum / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D054883:Oxylipins / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D015203:Reproducibility of Results; D052617:Solid Phase Microextraction / Q000379:methods; D013237:Stereoisomerism
D000085:Acetates; D003517:Cyclopentanes; D054883:Oxylipins; C072239:methyl jasmonate