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Food Chem

Title:		Isolation of the four methyl jasmonate stereoisomers and their effects on selected chiral volatile compounds in red raspberries
Author(s):		Flores G; Blanch GP; Ruiz Del Castillo ML;
Address:		"Instituto de Ciencia y Tecnologia de Alimentos y Nutricion, Consejo Superior de Investigaciones Cientificas (ICTAN-CSIC), c/ Juan de la Cierva 3, 28006 Madrid, Spain"
Journal Title:		Food Chem
Year:		2013
Volume:		20130606
Issue:		3
Page Number:		2982 - 2987
DOI:		10.1016/j.foodchem.2013.05.117
ISSN/ISBN:		1873-7072 (Electronic) 0308-8146 (Linking)
Abstract:		"The four stereoisomers present in a commercial sample of methyl jasmonate (MJ) were isolated at semi-preparative scale by HPLC, using a permethylated beta-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 alpha-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"
Keywords:		"Acetates/*chemistry/isolation & purification/*pharmacology Biotransformation/drug effects Chromatography, High Pressure Liquid Cyclopentanes/*chemistry/isolation & purification/*pharmacology Flavoring Agents/metabolism Fruit/drug effects/metabolism Oxylip;"
Notes:		"MedlineFlores, Gema Blanch, Gracia Patricia Ruiz del Castillo, Maria Luisa eng Research Support, Non-U.S. Gov't England 2013/07/23 Food Chem. 2013 Dec 1; 141(3):2982-7. doi: 10.1016/j.foodchem.2013.05.117. Epub 2013 Jun 6"