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A new conjugated linoleic acid isomer, 7 trans, 9 cis-octadecadienoic acid, in cow milk, cheese, beef and human milk and adipose tissue

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Lipids

Abstract

The identity of a previously unrecognized conjugated linoleic acid (CLA) isomer, 7 trans, 9 cis-octadecadienoic acid (18∶2) was confirmed in milk, cheese, beef, human milk, and human adipose tissue. The 7 trans, 9 cis-18∶2 isomer was resolved chromatographically as the methyl ester by silver ion-high-performance liquid chromatography (Ag+-HPLC); it eluted after the major 9 cis, 11 trans-18∶2 isomer (rumenic acid) in the natural products analyzed. In the biological matrices in-vestigated by Ag+-HPLC, the 7 trans, 9 cis-18∶2 peak was generally due to the most abundant minor CLA isomer, ranging in concentration from 3 to 16% of total CLA. By gas chromatography (GC) with long polar capillary columns, the methyl ester of 7 trans, 9 cis-18∶2 was shown to elute near the leading edge of the major 9 cis, 11 trans-18∶2 peak, while the 4,4-dimethyloxazoline (DMOX) derivative permitted partial resolution of these two CLA isomers. The DMOX derivative of this new CLA isomer was analyzed by gas chromatography-electron ionization mass spectrometry (GC-EIMS). The double bond positions were at Δ7 and Δ9 as indicated by the characteristic mass spectral fragment ions at m/z 168, 180, 194, and 206, and their allylic cleavages at m/z 154 and 234. The cis/trans double-bond configuration was established by GC-direct deposition-Fourier transform infrared as evidenced from the doublet at 988 and 949 cm−1 and absorptions at 3020 and 3002 cm−1. The 7 trans, 9 cis-18∶2 configuration was established by GC-EIMS for the DMOX derivative of the natural products examined, and by comparison to a similar product obtained from treatment of a mixture of methyl 8-hydroxy-and 11-hydroxyoctadec-9 cis enoates with BF3, in methanol.

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Abbreviations

Ag+-HPLC:

silver ion-high-performance liquid chromatography

cis/trans :

fefers to all the CLA isomers having either a cis, trans or a trans, cis configuration

CLA:

conjugated linoleic acid

DMOX:

4,4-dimethyloxazoline

FAME:

fatty acid methyl esters

GC-DD-FTIR:

gas chromatography-direct deposition-Fourier transform infrared

GC-EIMS:

gas chromatography-electron ionization mass spectrometry

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Author information

Authors and Affiliations

  1. Office of Food Labeling, U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition, 200 C St., S.W., DC 20204, Washington

    Martin P. Yurawecz, John A. G. Roach, Najibullah Sehat, Magdi M. Mossoba & Youh Ku

  2. Southern Crop Protection, Food Research Center, Agriculture and Agri-Food Canada, N1G2W1, Guelph, Ontario, Canada

    John K. G. Kramer

  3. Institute of Food Chemistry, University of Hamburg, Hamburg, Germany

    Jan Fritsche & Hans Steinhart

Authors
  1. Martin P. Yurawecz
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  2. John A. G. Roach
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  3. Najibullah Sehat
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  4. Magdi M. Mossoba
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  5. John K. G. Kramer
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  6. Jan Fritsche
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  7. Hans Steinhart
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  8. Youh Ku
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Corresponding author

Correspondence to Martin P. Yurawecz.

Additional information

Contribution number S010 from the Food Research Center, Guelph, Ontario, Canada.

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Yurawecz, M.P., Roach, J.A.G., Sehat, N. et al. A new conjugated linoleic acid isomer, 7 trans, 9 cis-octadecadienoic acid, in cow milk, cheese, beef and human milk and adipose tissue. Lipids 33, 803–809 (1998). https://doi.org/10.1007/s11745-998-0273-z

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  • DOI: https://doi.org/10.1007/s11745-998-0273-z

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