Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 2: mass spectral characterization |
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Authors: | Cui Pei H Duke Rujee K Tattam Bruce N Duke Colin C |
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Institution: | Pharmacogenomics, Faculty of Pharmacy, University of Sydney, NSW 2006, Australia. |
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Abstract: | Methyl esters of C18 polyunsaturated fatty acids, including gamma-linolenic acid, alpha-linolenic acid and stearidonic acid, were epoxidised using m-chloroperbenzoic acid. Nine monoepoxides were obtained by normal-phase HPLC, identified using LC-MS and NMR, and characterized by NMR spectroscopy and mass spectrometry. This study is focused on structural characterization using LC-MS and LC/APCI/MS/MS. The elution profiles of these monoepoxides in RP-HPLC are determined as 12,13->9,10->6,7-epoxy, 9,10->15,16->12,13-epoxy and 15,16->12,13->9,10-epoxy derivatives of gamma-linolenic, alpha-linolenic and stearidonic acid methyl esters, respectively. The major diagnostic fragmentations in MS/MS identified are postulated to be induced by cleavages of the epoxide ring and alpha-bond cleavage to the epoxy group from M+H]+ and/or M+H-MeOH]+. |
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Keywords: | Epoxide Epoxy fatty acids Polyunsaturated fatty acid NMR Mass spectrometry HPLC |
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