DOI QR코드

DOI QR Code

Elimination of Saturated Fatty Acids, Toxic Cyclic nonapeptide and Cyanogen Glycoside Components from Flax Seed Oil

  • Choi, Eun-Mi (Life Science Research Institute, E.S. Biotechnology Co. Ltd.) ;
  • Kim, Jeung-Won (Life Science Research Institute, E.S. Biotechnology Co. Ltd.) ;
  • Pyo, Mi-Kyung (Life Science Research Institute, E.S. Biotechnology Co. Ltd.) ;
  • Jo, Sung-Jun (Life Science Research Institute, E.S. Biotechnology Co. Ltd.) ;
  • Han, Byung-Hoon (Life Science Research Institute, E.S. Biotechnology Co. Ltd.)
  • Published : 2007.03.30

Abstract

Flax seed(Linseed, Linum usitatissimum L.) and its oil, a richest source of alpha-linolenic acid(ALA)(${\omega}-3$), contain saturated fatty acids, neurotoxic cyanogen glycosides and immuno-suppressive cyclic-nonapeptides. Present paper describes the development of two chemical processes, Process-A and -B, to remove saturated fatty acids and to destroy cyclic nonapeptides and cyanogen glycosides from flax seed oil. Process-A consists of three major steps, i.e., extraction of fatty acid mixture by alkaline saponification, removal of saturated fatty acid by urea-complexation, and triglyceride reconstruction of unsaturated fatty acid via fatty acyl-chloride activation using oxalyl chloride. Process-B consists of preparation of fatty acid ethyl ester by transesterification, elimination of saturated fatty acid ester by urea-complexation, and reconstruction of triglyceride by interesterification with glycerol-triacetate (triacetin). The destruction of lipophilic cyclic nonapeptide during saponification or transesterification processes could be demonstrated indirectly by the disappearance of antibacterial activity of bacitracin, an analogous cyclic-decapeptide. The cyanogen glycosides were found only in the dregs after hexane extraction, but not in the flax seed oil. The reconstructed triglyceride of flax seed oil, obtained by these two different pathways after elimination of saturated fatty acid and toxic components, showed agreeable properties as edible oil in terms of taste, acid value, iodine and peroxide value, glycerine content, and antioxidant activity.

Keywords

References

  1. Ahrens, E. H., Blankenhorn, D.H. and Tsaltas, T.T. (1954). Effect on human serum lipids of substituting plant for animal fat in the diet. Proc. Soc. Exp. Biol. Med. 86, 872-8 https://doi.org/10.3181/00379727-86-21260
  2. Christie W. W. Lipid analysis, Pergamon Press. p-714, 1973
  3. Canmar Grain Products Corp.Canada through Ihreflex Co. Ltd. In Korea(Personal communication), Roasted Golden Flax seed Presentation
  4. Egekeze, J. O., Dowling T. M., Neru, G., Holly, J. P. and Gray, R. B. (1997). Talanta. 44, 1203-9 https://doi.org/10.1016/S0039-9140(96)02160-1
  5. Herald, W., Dietmal, R., Sabine, B., and Karl-Wolfgang, M. (1994) Immunocytol. localization of hydroxynitrile lyses from Sorghum bicolor L. and Linum usitassimumL. Plant Sci., 103, 145 54 https://doi.org/10.1016/0168-9452(94)90202-X
  6. Hettiarachchy, N., Hareland, G., Ostenson, A. and Balder-Shank, G. (1990). Composition of eleven flax seed varieties grown in North Dakota Proc. 53rd. Flax Inst. P. 36-40
  7. Hiroshi, M., Akira, S., Teruki, M., Koichi, T., Hideji, I., Toshihiko, H. and Kitaro, O. (1997). A new immunosuppressive cyclic nonapeptide, cyclolinopeptide B from Linumusitissimum. Bioorg. Med. Chem. Letters. 7, 10, 1269-72 https://doi.org/10.1016/S0960-894X(97)00206-0
  8. Hegsted, D. M., McGandy, R. B., Myers, M. L. and Stare, F. J. (1965). Quantitative effects of dietary fat on serum cholesterol in man. Am. J. Clin. Nutr. 17, 281-95 https://doi.org/10.1093/ajcn/17.5.281
  9. Hwang, D. H. and Carroll, A. E. (1980). Decreased formation of prostaglandins derived from arachidonic acid by dietary linolenate in rats. J. Clin. Nutr. 33, 590-7 https://doi.org/10.1093/ajcn/33.3.590
  10. Irena Nied'zwied'z-Siege'n. (1998). Cyanogenic glycosides in Linum usitatissimum, Phytochem. 49, 1, 59-63 https://doi.org/10.1016/S0031-9422(97)00953-9
  11. Jorgensen, J. H. and Sahm, D. E. (1995). Manual of Clinical Microbiology, 6th ed., ASN, Washington, 1277
  12. Karl, G.., Guenter, G.., Barbara, K., Helmut, S. and Christoph, K. (2004). Reaction mechanism of Hydroxynitrile Lyases of the a/b-Hydrolase Superfamily. J. Biol. Chem., 279( 19), 20501-10 https://doi.org/10.1074/jbc.M401575200
  13. Keys, A., Anderson, J. T. and Grande, F. (1957), Prediction of serum cholesterol response of man to change in fats in the diet. Lancet. 2, 959-66 https://doi.org/10.1016/S0140-6736(57)91998-0
  14. Kinsel, L. W., Partridge, J., Boling, L., Margen, S. and Michaels, G. P. (1952) Dietary modification of serum cholesterol and phospholipids. J. Clin. Endoclinol. 12, 909-13 https://doi.org/10.1210/jcem-12-7-909
  15. Lorian, V. (1996). Antibiotics in Laboratory Medicine. Williams & Wilkins. Baltimore
  16. Merina, E., Bala, N. and Sudhakaran, P. R. (1997) Catabolism of linamarin in cassava(Manihot esculenta cranz). Plant Science. 126, 155-62 https://doi.org/10.1016/S0168-9452(97)00100-3
  17. Roberta, R. E., Nicoletta, P., Anna, P., Ananth, P., Min, Y. and Catherine, R. (1999). Antioxidant. activity applying an improved ABTS radical cation decolourization assay. Free Radical Biol. Med. 26(9/10), 1231-7 https://doi.org/10.1016/S0891-5849(98)00315-3
  18. Terry, J., Gaymes, M. C., Ignacy, Z. S. and John, E. K. (1997) Cyclolinopeptide A(CLA) mediates its immunosuppressive activity through cyclophilin dependent calcineurin inactivation. FEBS, Letter. 418, 224-7 https://doi.org/10.1016/S0014-5793(97)01345-8
  19. U.S. Department of Health and Human Services. (1997). Atlanta, GA., Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Cyanide Update). Public Health Service
  20. Visjaimohan, K., Mallika, J., Sabitha, K. E., Subramaniyam, S., Anandhan, C. and Shyamala, Devi C. S. (2007) Beneficial effects of alpha linolenic acid rich flax seed oil on growth performance and hepatic cholesterol metabolism in high fat diet fed rats. Life Sciences. In press
  21. Willls, A. L. (1981). Nutritional and pharmacological factors in eicosanoid biology. Nutr. Rev. 39, 289-301 https://doi.org/10.1111/j.1753-4887.1981.tb06794.x

Cited by

  1. Quality and Antioxidant Properties of Pound Cakes Supplemented with Flaxseed Powder vol.43, pp.12, 2014, https://doi.org/10.3746/jkfn.2014.43.12.1959