title: Isolation of the four methyl jasmonate stereoisomers and their effects on selected chiral volatile compounds in red raspberries.
abstract: The four stereoisomers present in a commercial sample of methyl jasmonate (MJ) were isolated at semi-preparative scale by HPLC, using a permethylated β-cyclodextrin column. This allowed the baseline resolution and collection of both major (methyl jasmonates) and minor (epi-methyl jasmonates) stereoisomers. When 1.5 mL of a 5mg per mL MJ solution were injected, isolated amounts were 3.56 mg for (-) and (+)-methyl jasmonates, with respective purities of 96.1% and 99.9%, and 0.18 mg for (-)- and (+)-epi-methyl jasmonates, with 98.6% and 91.6% respective purities. The post-harvest treatment of red raspberry fruits with the pure methyl jasmonate stereoisomers isolated proved that (-)-epi-MJ either promotes the bioformation of (+)-limonene or inhibits that of (-)-limonene to a greater extent than the other three MJ stereoisomers, while the biosynthesis of the (+)-enantiomer of α-ionone is favoured equally, whichever MJ stereoisomer used. The results obtained in the present study might be used to obtain food products with improved sensory characteristics.
authors.affiliation: Instituto de Ciencia y Tecnología de Alimentos y Nutrición, Consejo Superior de Investigaciones Científicas (ICTAN-CSIC), c/ Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Gema
authors.initials: G
authors.lastname: Flores
authors.forename: Gracia Patricia
authors.initials: GP
authors.lastname: Blanch
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Ruiz del Castillo
mesh_terms: D000085:Acetates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001711:Biotransformation / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D005421:Flavoring Agents / Q000378:metabolism; D005638:Fruit / Q000187:drug effects / Q000378:metabolism; D054883:Oxylipins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D027824:Rosaceae / Q000187:drug effects* / Q000378:metabolism*; D013237:Stereoisomerism; D055549:Volatile Organic Compounds / Q000378:metabolism*
chemical_list: D000085:Acetates; D003517:Cyclopentanes; D005421:Flavoring Agents; D054883:Oxylipins; D055549:Volatile Organic Compounds; C072239:methyl jasmonate
keywords: Aroma; Chiral; Enantiomer; Functional foods; Methyl jasmonate; Raspberry; epi-Methyl jasmonate