Abstract
Methyl-branched fatty acids, which are usually minor components (≤0.1%) in fish oils, were concentrated in the non-urea-complexing fraction along with polyunsaturated fatty acids during the enrichment of omega-3 fatty acids from certain fish oils via the urea complexation process. The methyl-branched fatty acids in the omega-3 polyunsaturated fatty acid concentrates, which were prepared from three fish body oils, were characterized by gas chromatography and gas chromatography/mass spectrometry. Among the major branched-chain fatty acids expected and identified were the known isoprenoid acids—mainly 4,8,12-trimethyltridecanoic, pristanic, and phytanic—and the well-known iso and anteiso structures. Two novel phytol-derived multimethyl-branched fatty acids, 2,2,6,10,14-pentamethylpentadecanoic and 2,3,7,11,15-pentamethylhexadecanoic, were identified in redfish (Sebastes sp.) oil. These two fatty acids were absent in oils from menhaden (Brevoortia tyrannus) and Pacific salmon (mixed, but mostly from sockeye,Oncorhynchus nerka). The major branched-chain fatty acid in the salmon oil, 7-methyl-7-hexadecenoic acid, was also present to a moderate extent in menhaden oil. A novel vicinal dimethyl-branched fatty acid, 7,8-dimethyl-7-hexadecenoic was detected in all of the fish oils examined, but was most important in the salmon oil. Three monomethyl-branched fatty acids, 11-methyltetradecanoic acid, and 11- and 13-methylhexadecanoic, hitherto undescribed in fish lipids, were also detected in salmon, redfish and menhaden oils.
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Abbreviations
- AgNO3-TLC:
-
silver nitrate-thin layer chromatography
- BCFA:
-
branched-chain fatty acid
- DHA:
-
docosahexaenoic acid
- DMHD:
-
dimethylhexadecanoic acid
- ECL:
-
equivalent chain length
- EPA:
-
eicosapentaenoic acid
- FID:
-
flame ionization detector
- GC/MS:
-
gas chromatography/mass-spectrometry
- GLC:
-
gas-liquid chromatography
- ITD:
-
Ion Trap Detector
- MHD:
-
methylhexadecanoic
- MTD:
-
methyltetradecanoic
- NUCF:
-
non-urea-complexing fraction
- PMHD:
-
pentamethylhexadecanoic
- PMPD:
-
pentamethylpentadecanoic
- PUFA:
-
polyunsaturated fatty acid
- TMHD:
-
tetramethylhexadecanoic or phytanic
- TMPD:
-
tetramethylpentadecanoic acid or pristanic
- TMTD:
-
trimethyltridecanoic acid
References
Ackman, R.G., and Hooper, S.N. (1968)Comp. Biochem. Physiol. 24, 549–565.
Lough, A.K. (1973)Prog. Chem. Fats and Other Lipids, XIV, 5–48.
Dyerberg, J., and Jorgensen, K.A. (1982)Prog. Lipid Res. 21, 255–269.
Kromhout, D., Bosschieter, E.B., and Coulander, C. de L. (1985)N. Engl. J. Med. 312, 1205–1209.
Ackman, R.G. (1980)Advances in Fish Science and Technology (J.J. Connell, ed.), pp. 86–103, Fishing News Books Ltd., Surrey, England.
Ackman, R.G. (1982) inNutritional Evaluation of Long-chain Fatty Acids in Fish Oil (S.M. Barlow and M.E. Stansby, eds.), pp. 25–88, Academic Press, N.Y., N.Y..
Ackman, R.G. (1988)Chem. and Ind. 139–145.
Bailey, B.E. (1952) inBulletin 89; Marine Oils with Particular Reference to Those of Canada. Fish. Res. Bd. Can., Ottawa, Canada.
Ackman, R.G., Burgher, R.D., and Jangaard, P.M. (1963)Can. J. Biochem. Physiol. 41, 1627–1641.
Ratnayake, W.M.N., Olsson, B., Matthews, D., and Ackman, R.G. (1988)Fat. Sci. Technol. 90, 381–386.
Ackman, R.G., Ratnayake, W.M.N., and Olsson, B. (1988)J. Am. Oil. Chem. Soc. 65, 136–138.
Wachs, W., and May, A. (1968)Deut. Lebensm. Rundsch. 64, 412–416.
Sen Gupta, A.K., and Peters, H. (1966)Fette Seifen Anstrichmittel 68, 349–360
Ackman, R.G., Sipos, J.C., and Hooper, S.N. (1977)J. Am. Oil. Chem. Soc. 54, 199–201.
Sano, Y. (1966)Yukagaku 15, 99–108.
Sano, Y. (1966)Yukagaku 15, 140–147.
Sano, Y. (1966)Yukagaku 15, 456–160.
Sano, Y. (1967)Yukagaku 16, 8–12.
Sano, Y. (1967)Yakagaku 16, 56–61.
Sano, Y., Aikawa, D. and Murase, K., (1965)Yukagaku 14, 171–178.
Pascal, J.C., and Ackman, R.G. (1975)Lipids 10, 478–482.
Ackman, R.G., Safe, L., Hooper, S.N., Paradis, M., and Safe, S. (1973)Lipids 8, 21–24.
Morrison, W.R., and Smith, L.M. (1964)J. Lipid Res. 5, 600–608.
Sébédio, J-L., and Ackman, R.G. (1981)Lipids 16, 461–467.
Harvey, D.J. (1982)Biomedical Mass Spectrometry 9, 33–38.
Ackman, R.G., Sipos, J.C., and Tocher, C.S. (1967)J. Fish. Res. Bd. Canada 24, 635–650.
Ackman, R.G. (1968)J. Chromatog. 34, 165–173.
Ackman, R.G. (1967)J. Chromatog. 28, 225–331.
Ackman, R.G. (1969)J. Chromatog. 29, 170–175.
McLafferty, F.W. (1980)Interpretation of Mass Spectra, 3rd edition, University Science Books, Mill Valley, CA.
Abrahamsson, S., Stallberg-Stenhagen, S., and Stenhagen, E. (1964)Prog. Chem. Fats other Lipids 7, 1–157.
McCloskey, J.A. (1969)Methods in Enzymol. XIV, 382–450.
Douglas, A.G., Blumer, M., Eglinton, G., and Douraghi-Zadeh, K. (1971)Tetrahedron 27 1071–1092.
Ratnayake, W.M.N., Timmins, A., Ohshima T., and Ackman, R.G. (1986)Lipids 21, 518–524.
Ackman, R.G., and Hansen, R.P. (1967)Lipids 2, 357–362.
Christie, W.W., Brechany, E.Y., Johnson, S.B., and Holman, R.T. (1986)Lipids 21, 657–661.
Egge, H., Murawski, U., Ryhage, R., Gyorgy, P., Chatranon, W., and Zilkiken, F. (1972)Chem. Phys. Lipids 8, 42–55.
Maclean, I., Eglinton, G., Douraghi-Zadeh, K., Ackman, R.G., and Hooper, S.N. (1968).Nature 218, 1019–1023.
Cox, R.E., Maxwell, J.R., Ackman, R.G., and Hooper, S.N. (1972)Can. J. Biochem. 50, 1238–1241.
Ackman, R.G. (1971)Lipids 6, 520–522.
Carballeira, N.M., and Maldonado, M.E. (1988)Lipids 23, 690–693.
Sano, Y. (1967)Yukagaku 16, 605–610.
Karlsson, K-A., Leffler, H., and Samuelsson, B.O.E. (1979),Biochim. Biophys. Acta 574, 79–93.
Marzouki, Z.M.H., Taha, A.M., and Gomaa, K.S. (1988)J. Chromatogr. 425, 11–24.
Dolphin, P.J., Amy, R.M., Koeslag, D.G., Limoges, B.F., and Russell, J.C. (1988)Biochim. Biophys. Acta 962, 317–329.
Philbrick, D-J., Mahadevappa, V.P., Ackman, R.G., and Holub, B.J. (1987)J. Nutr. 117, 1663–1670.
Ota, T., and Takagi, T. (1982)Bull. Fac. Fish. Hokkaido Univ. 33, 149–153.
Scrimgeour, C.M. (1977)J. Am. Oil Chem. Soc. 54, 210–211.
Ackman, R.G., and Harrington, M. (1975)J. Can. Diet. Ass. 36, 50–53.
Dulaney, J.T., Williams, M., Evans, J.E., Costell, C.E., and Kolodny, E.H. (1978)Biochim. Biophys. Acta 529, 1–12.
Leaf, A., and Weber, P.C. (1981)N. Eng. J. Med. 318, 549–557.
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Ratnayake, W.M.N., Olsson, B. & Ackman, R.G. Novel branched-chain fatty acids in certain fish oils. Lipids 24, 630–637 (1989). https://doi.org/10.1007/BF02535080
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DOI: https://doi.org/10.1007/BF02535080