Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
권호 표지
DOI QR코드

DOI QR Code

Identification of Fatty Acids in the Oils of Pine Nuts by GC-MS of Their Picolinyl Esters and 4,4-dimethyloxazoline Derivatives in Combination with Silver-Ion Chromatography

  • Kim, Seong-Jin (Department of Food Science & Nutrition, Dong-A University) ;
  • Woo, Hyo-Kyeng (Department of Food Science & Nutrition, Dong-A University) ;
  • Seo, Min-Young (Department of Food Science & Nutrition, Dong-A University) ;
  • Joh, Yong-Goe (Department of Food Science & Nutrition, Dong-A University)
  • Published : 2002.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

A mixture of methyl ester derivatives of fatty acids from the oils of pine nuts was well resolved to five fractions differing by degree of unsaturation by silver ion solid-phase extraction column chromatography ($Ag^{+}$-SEC). Polyunsaturated fatty acid with non-methylene interrupted conjugated double bond (NMiDB) radical held more strongly to silver ions in the column than methylene interrupted conjugated double bond (MiDB) one when they had the same number of double bonds. Although both the picolinyl ester and DMOX derivative provided clear mass ion species powerful enough to elucidate the structure of the polyunsaturated fatty acid (PUFA) with NMiDB and/or methylene interrupted conjugated double bond (MiDB) radical in the oils, the picolinyl ester of PUFA with NMiDB radical did not provide a cluster of mass ions neighboring diagnostic mass ions induced by the double bond in the proximal to the carboxyl group. However, the DMOX derivative of PUFA with NMiDB group as well as MiDB showed abundant mass ion species differing by gaps of 12 amu, which made it possible with greater ease to locate the double bonds in the molecule. The oil contained $C_{18:2{\omega}6}$ (46.2 %) and $C_{18:1{\omega}9}$ (25.4 %) as main components, and considerable amounts of PUFAs with NMiDB radical such as ${\Delta}^{5.\;9.\;12}-C_{18:3}$ (16.0 %), ${\Delta}^{5.\;9}-C_{18:2}$ (2.3 %) and ${\Delta}^{5.\;11.\;14}-C_{20:3}$ (0.8 %).

Keywords

References

  1. B. A. Andersson, Prog. Chem. Fats and Other Lipids, 16. 279 (1978) https://doi.org/10.1016/0079-6832(78)90048-4
  2. D. J. Harvey, 'Advances in Lipid Methodology-One', edited by W. W.Chhstie, pp. 19-80, The Oily Press, Dundee, Scotland (1992)
  3. A. P. Tulloch, Lipids, 20, 652 (1985) https://doi.org/10.1007/BF02534383
  4. Q. T. Yu, J. Y. Zhang and Z. H. Huang,Biomed Mass Spectrom., 13, 212 (1987)
  5. D. J. Harvey, Biomed Mass Spectrom.,11, 340 (1984) https://doi.org/10.1002/bms.1200110705
  6. D. J. Harvey, Biomed. Mass Spectrom., 11, 187 (1984) https://doi.org/10.1002/bms.1200110410
  7. W. W. Chrisde, E. Y. Brechany, S. B. Johnson, and R. T. Holman, Lipids, 21, 657 (1986) https://doi.org/10.1007/BF02537217
  8. Y. -G. Joh, I. J. Elenkov, K. L. Stefanov, S. S. Popov, G. Dobson, and W. W. Chhstie, Lipids, 32, 13 (1997) https://doi.org/10.1007/s11745-997-0003-6
  9. W. W. Christie, E. Y. Brechany, M. S. F. Lie Ken Jie, and O. Bakare, Biol. Mass Spectrom., 20, 629 (1991) https://doi.org/10.1002/bms.1200201007
  10. W. W. Chrisde, E. Y. Brechany, M. S. F. Lie Ken Jie, and C. F. Wbng, Biol. Mass Spectrom., 21, 267 (1992) https://doi.org/10.1002/bms.1200210508
  11. J. Y. Zhang, Q. T. Yu, B. N. Liu, and Z. H. Huang, Biomed Mass Spectrom., 15, 33 (1988) https://doi.org/10.1002/bms.1200150106
  12. V. Spitzer, Prog. Chem. Fats and Other Lipids, 35, 387 (1997)
  13. J. A. G. Roach, M. P. Yurawecz, M. M. Mossoba, and K. Eulitz, 'Spectral Properties of Lipids', edited by R. J. Hamilton and J. Cast, pp. 141-182, Sheffield Academic Press, ShefSeld, England (1999)
  14. J. Y. Zhang, H. Y. Wang, Q. T. Yu, B.N. Liu, and Z. H. Huang, J. Am Oil Chem Soc., 66, 242 (1989) https://doi.org/10.1007/BF02546068
  15. J. Y. Zhang, X. J. Yu, H. Y. Wang, B. N. Liu, Q. T. Yu, and Z. H. Huang, J. Am. Oil Chem. Soc., 66, 256 (1989) https://doi.org/10.1007/BF02546071
  16. H. M. Liebich, N. Schmeider, H. G. Wahl, and J. Wahl, J. High ResoI Chromatogr., 17, 519 (1994) https://doi.org/10.1002/jhrc.1240170703
  17. V. Spitzer, J. High ResoI Chromatogr., 18, 413 (1995) https://doi.org/10.1002/jhrc.1240180704
  18. V. Spitzer, Phytochemistry, 42, 1357 (1996) https://doi.org/10.1016/0031-9422(96)00140-9
  19. Q. T. Yu, B. N. Liu, J. Y. Zhang, and Z. H. Huang, Lipids, 24, 79 (1989) https://doi.org/10.1007/BF02535269
  20. B. Nikolova-Damyanova, 'Advances in Lipid Methodology-One', edited by W. W. Chhstie, pp. 181-237, The Oily Press, Dundee, Scotland (1992)
  21. W. W. Christie, 'Lipid Analysis (2nded.)', pp. 74-75, Pergamon Press, Oxford, UK (1982)
  22. W. W. Christie, J. Lipid Res., 30, 1471 (1989)
  23. W. W. Chhstie, J. Sci. Food Agric., 52, 573 (1990) https://doi.org/10.1002/jsfa.2740520414
  24. R. O. Adolf and E. A. Emken, J. Am Oil Chem. Soc., 62, 1592 (1985) https://doi.org/10.1007/BF02541694
  25. O, S. Privett, M. L. Blank, D.Codding, and E. C. Nickell, J. Am Oil Chem Soc., 42, 381 (1965) https://doi.org/10.1007/BF02635573
  26. H. K. Mangold, 'Thin-Layer Chromatography', edited by E. Stahl, pp. 363-421, Springer-Verlag, New York (1969)
  27. B. Nikolova-Damyanova, B. Herslof, and W. W. Christie, J. Chromatogr., 609, 133 (1992) https://doi.org/10.1016/0021-9673(92)80156-O
  28. B. Nikolova-Damyanova, W. W. Christie, and B. Herslof, J. Chromatogr. A, 749, 47 (1996) https://doi.org/10.1016/0021-9673(96)00365-2
  29. W. W. Chhstie, E. Y. Brechany, K. L. Stefanov, and S. S. Popov, Lipicls, 27, 640 (1992)
  30. M. T. G. Hierro, G. Robertson, W. W. Chhstie, and Y. -G. Joh, J. Am. Oil Chem Soc., 73, 575 (1996) https://doi.org/10.1007/BF02518110