Occurrence of cis-4-Tetradecenoic Acid in the Oils of Kernels of Lindera erythrocarpa Seeds, as a Major Component

  • Kim, Seong-Jin (Department of Food Science & Nutrition, Dong-A University) ;
  • Joh, Yong-Goe (Department of Food Science & Nutrition, Dong-A University)
  • Published : 2006.02.28

Abstract

Kernel oils of Lindera erythrocarpa seeds had high level of unusual fatty acid. Picolinyl ester of this unknown fatty acid showed molecular ion at m/z = 317 with other diagnostic ions such as m/z = 151, 191 (40 amu between two peaks), 204, and 218 on GC-MS. Characteristic peak at $720\;cm^{-1}$ appeared in IR spectrum. In $^1H-NMR$ spectrum both methylene protons at C-3 and C-6 resonated at ${\delta}2.309$ and ${\delta}2.012$, and methine protons of double bond resonated in lower magnetic field centered at ${\delta}5.296$ (C-4) and ${\delta}5.387$ (C-5) as multiplet (J = 9.7Hz). In $^{13}C-NMR$, signals at ${\delta}22.669$ and ${\delta}27.048$ were due to C-3 and C-6 of ${\delta}^4$-monoenoic acid. Results obtained from spectroscopic measurements confirmed unknown fatty acid as cis-4-tetradecenoic acid (cis-4-$C_{14:1}$). Main fatty acid components of oils were cis-4-$C_{14:1}$ (44.5-45.1%), oleic acid ($C_{18:1}$), 20.4-21.3%), and lauric acid ($C_{12:0}$, 11.6-12.4%), along with trace amounts of cis-4-$C_{12:1}$ and cis-4-$C_{16:1}$.

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References

  1. Song JT, Chung HB, Kim BW, Jin HS. Colourful Korean Flora Encyclopedia. vol. 1 (in Korean), Che-II Pub. Co., Ltd., Seoul, Korea pp. 308-320 (1989)
  2. Hopkins CY, Chisholm MJ, Prince L. Fatty acids of Lindera umbellata and other Lauraceae seed oils. Lipids 1: 118-122 (1965) https://doi.org/10.1007/BF02533002
  3. Hitchcock C. Fatty Acids. pp. 1-19. In: Recent Advances in the Chemistry and Biochemistry of Plant Lipids. Galliard T. and Mercer EI. (ed), Academic Press, New York, NY, USA (1975)
  4. Christie WW, Brechany EY, Shukla VKS. Analysis of seed oils containing cyclopentenyl fatty acids by combined chromatographic procedures. Lipids 24: 116-120 (1989) https://doi.org/10.1007/BF02535247
  5. Bligh EG, Dyer WI A rapid method of total lipid extraction and purification. Can. J. Physiol. 37: 911-917 (1959) https://doi.org/10.1139/y59-099
  6. Kim SJ, Woo HK, Seo MY, Joh yo. Analysis of the fatty acids in puffer fish liver oils by combined chromatographic proceduresresolution of fatty acid methyl esters by Ag'vchromatography and their identification by GC-MS using 4, 4-methyloxazoline derivatives. Food Sci. Biotechnol. 12: 326-336 (2003)
  7. Christie ww. Silver ion chromatography using solid-phase extraction columns packed with a bonded-sulfonic acid phase. J. Lipid Res. 30: 1471-1473 (1989)
  8. Chapman D. Infrared spectroscopy of lipids. J. Am. Oil Chem. Soc. 42: 353-371 (1965) https://doi.org/10.1007/BF02635571
  9. Balazy M, Nies AS. Characterization of epoxides of polyunsaturated fatty acids by mass spectrometry via 3-pyridinylmethyl esters. Biomed. Environ. Mass Spectrom. 18: 328-336 (1989) https://doi.org/10.1002/bms.1200180508
  10. Christie WW, Brechany EY, Holman T. Mass spectra of the picolinyl esters of isomeric mono- and dienoic fatty acids. Lipids 22: 224-228 (1987) https://doi.org/10.1007/BF02533983
  11. Silverstein M, Bassler GC, Morrill TC. Proton Magnetic Resonance Spectrometry. pp. 181-238. In: Spectrometric Identification of Organic Compounds, 4th ed., John Wiley & Sons, New York, NY, USA (1981)
  12. Christie WW. GC and Lipids. The Oily Press, Ayr, Scotland, UK (1982)
  13. Joh YG, Elenkov IJ, Stefanov KL, Popov SS, Dobson G, Christie ww. Novel di-, tri-, and tetraenoic fatty acids with bis-methyleneinterrupted double-bond systems from the sponge Haliclona cinerea. Lipids 32: 13-17 (1997) https://doi.org/10.1007/s11745-997-0003-6
  14. Williams DH, Fleming J. Spectroscopic Methods in Organic Chemistry, McGraw-Hill, New York, USA (1966)
  15. Batchelor JG, Cushley RJ, Prestegard JH. Carbon-13 fourier transform nulcear magnetic resonance VIII. Role of steric and electric field effects in fatty acid spectra. J. Org. Chem. 39: 16981705 (1974) https://doi.org/10.1021/jo00925a023
  16. Bus J, Sies I, Lie Ken Jie MSF. 13C-NMR of methyl, methylene and carbonyl carbon atoms of methyl a1kenoates and alkynoates. Chem. Phys. Lipids 17: 501-518 (1976) https://doi.org/10.1016/0009-3084(76)90049-9
  17. Hopkins CY. Nuclear Magnetic Resonance in Fatty Acids and Glycerides, Vol. 8, part 2. pp. 215-252. In: Progress in the Chemistry of Fats and Other Lipids, Holman RT. (ed), Pergamon Press, Oxford, UK (1965)
  18. Gunstone FD. Fatty Acid and Lipid Chemistry, 1st ed., B1ackie Academic & Professional, London, UK pp. 6-8 (1996)
  19. Cahoon EB, Shanklin J, Ohlrogge JB. Expression of a coriander desaturase results in petrose1inic acid production in transgenic tobacco. Proc. Natl. Acad. Sci. USA 89: 1184 (1992)
  20. Murphy DJ. Identification and characterization of genes and enzyme for the genetic engineering of oilseed crops for production of oils for the oleochemical industry: a review. Ind. Crops Prod. 1: 251 (1993) https://doi.org/10.1016/0926-6690(92)90026-R
  21. Ohlrogge JB. Design for new plant products: engineering of fatty Acid metabolism. Plant Physiol. 104: 821 (1994) https://doi.org/10.1104/pp.104.3.821
  22. Surh JH, Kwon HJ. Fatty acid content and composition of various Korean shellfish. Food Sci. Biotechnol. 12: 83-87 (2003)