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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M800662-JLR200 on June 19, 2009

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Journal of Lipid Research, Vol. 50, 2412-2420, December 2009
Copyright © 2009 by American Society for Biochemistry and Molecular Biology

Characterization of cis-9 trans-11 trans-15 C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS

Pilar Gómez-Cortés*, Cynthia Tyburczy{dagger}, J. Thomas Brenna{dagger}, Manuela Juárez* and Miguel Angel de la Fuente1,*

* Instituto del Frío (Consejo Superior de Investigaciones Científicas), José Antonio Novais 10, 28040 Madrid, Spain
{dagger} Division of Nutritional Sciences, Cornell University, Ithaca, NY 14853

1 To whom correspondence should be addressed. e-mail: mafl{at}if.csic.es

Rumen biohydrogenation of dietary {alpha}-linolenic acid gives rise in ruminants to accumulation of fatty acid intermediates, some of which may be transferred into milk. Rumelenic acid [cis-9 trans-11 cis-15 C18:3 (RLnA)] has recently been characterized, but other C18:3 minor isomers are still unknown. The objective of this work was to identify a new isomer of octatridecenoic acid present in milk fat from ewes fed different sources of {alpha}-linolenic acid. Structural characterization of this fatty acid was achieved by GC-MS. Analysis of dimethyloxazoline and picolinyl ester derivatives allowed for location of the double bond positions. Covalent adduct chemical ionization tandem mass spectrometry confirmed the positional structure 9-11-15, identical to RLnA, and helped to establish double bond geometry (cis-trans-trans). This new C18:3 isomer could be formed by isomerization of cis-15 bond of RLnA and subsequently converted by hydrogenation to trans-11 trans-15 C18:2, an octadecadienoic acid also detected in this study.

Supplementary key words fatty acid • {alpha}-linolenic acid • conjugated linoleic acid • ewe • biohydrogenation intermediate • vaccenic acid • gas chromatography • mass spectrometry

Abbreviations: Ag+-HPLC, silver ion high performance liquid chromatography; CLA, conjugated linoleic acid; CACI-MS, covalent adduct chemical ionization mass spectrometry; CACI-MS/MS, covalent adduct chemical ionization tandem mass spectrometry; DMOX, dimethyloxazoline; FAME, fatty acid methyl esters; FID, flame ionization detector; RA, rumenic acid, cis-9 trans-11 C18:2; RLnA, rumelenic acid, cis-9 trans-11 cis-15 C18:3; TMR, total mixed ration; tR, retention time


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