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Original Articles

C19 Odd-chain Polyunsaturated Fatty Acids (PUFAs) Are Metabolized to C21-PUFAs in a Rat Liver Cell Line, and Curcumin, Gallic Acid, and Their Related Compounds Inhibit Their Desaturation

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Pages 1641-1650 | Received 24 Jan 2000, Accepted 26 Mar 2000, Published online: 22 May 2014

  • 1) Gross, R. W., High plasmalogen and arachidonic acid content of canine myocardial sarcolemma: a fast atom bombardment mass spectroscopic and gas chromatography-mass spectroscopic characterization. Biochemistry, 23, 158-165 (1984).
  • 2) Parodi, P. W., Positional distribution of fatty acids in triglycerides from milk of several species of mammals. Lipids, 17, 437-442 (1982).
  • 3) Paradis, M. and Ackman, R. G., Localization of a source of marine odd chain-length fatty acids. II. Seasonal propagation of odd chain-length monoethylenic fatty acids in a marine food chain. Lipids, 11, 871-876 (1976).
  • 4) Paradis, M. and Ackman, R. G., Localization of a marine source of odd chain-length fatty acids. I. The amphipod Pontoporeia femorata (Kroyer). Lipids, 11, 863-870 (1976).
  • 5) Aveldaño, M. I., Robinson, B. S., Johnson, D. W., and Poulos, A., Long and very long chain polyunsaturated fatty acids of the n-6 series in rat seminiferous tubules. J. Biol. Chem., 268, 11663-11669 (1993).
  • 6) Mayzaud, P. and Ackman, R. G., The 6,9,12,15,18-heneicosapentaenoic acid of seal oil. Lipids, 13, 25-28 (1978).
  • 7) Ackman, R. G., Eaton, C. A., and Hingley, J., Fillet fat and fatty acid details for Newfoundland winter herring. Can. Inst. Food Sci. Technol. J., 8, 155-159 (1975).
  • 8) Ackman, R. G., Sipos, J. C., and Jangaard, P. M., A quantitation problem in the open tubular gas chromatography of fatty acid esters from cod liver lipids. Lipids, 2, 251-257 (1967).
  • 9) Ackman, R. C., Eaton, C. A., and Jangaard, P. M., Lipids of the finwhale (Balaenoptera physalus) from north Atlantic waters. Can. J. Biochem., 43, 1521-1530 (1965).
  • 10) Rodríguez, C., Henderson, R. J., Porter, A. E. A., and Dick, J. R., Modification of odd-chain length unsaturaetd fatty acids by hepatocytes of rainbow trout (Oncorhynchus mykiss) fed diets containing fish oil or olive oil., Lipids, 32, 611-619 (1997).
  • 11) Larsen, L. N., Høvik, K., Bremer, J., Holm, K. H., Myhren, F., and Børretzen, B., Heneicosapentaenoate (21:5n-3): its incorporation into lipids and its effects on arachidonic acid and eicosanoid synthesis. Lipids, 32, 707-714 (1997).
  • 12) Schlenk, H. and Sand, D. M., A new group of essential fatty acids and their comparison with other polyenoic fatty acids. Biochim. Biophys. Acta., 44, 305-320 (1967).
  • 13) Ikeda, I., Murakami, J., Oka, T., Sugano, M., Yamada, H., Shimizu, S., Kawashima, H., Shinmen, Y., and Amachi, T., Effects of oleic, arachidonic and 5,8,11,14-nonadecatetraenoic acids on lipid secretion and ketogenesis in perfused rat liver. Lipids, 26, 27-30 (1991).
  • 14) Shirasaka, N., Yokochi, T., and Shimizu, S., Formation of a novel odd chain polyunsaturated fatty acid, 5,8,11,14,17-cis-nonadecapentaenoic acid, by an EPA-producing aquatic fungus, Saprolegnia sp. 28YTF-1. Biosci. Biotechnol. Biochem., 59, 1963-1965 (1995).
  • 15) Shimizu, S., Kawashima, H., Akimoto, K., Shinmen, Y., and Yamada, H., Production of odd chain polyunsaturated fatty acids by Mortierella fungi. J. Am. Oil. Chem. Soc., 68, 254-258 (1991).
  • 16) Sprecher, H., Biochemistry of essential fatty acids. Prog. Lipid Res., 20, 13-22 (1981).
  • 17) Kawashima, H., Akimoto, K., Shiresaka, N., and Shimizu, S., Inhibitory effects of alkyl gallate and its derivatives on fatty acid desaturation. Biochim. Biophys. Acta., 1299, 34-38 (1996).
  • 18) Kawashima, H., Akimoto, K., Jareonkitmongkol, S., Shiresaka, N., and Shimizu, S., Inhibition of rat liver microsomal desaturases by curcumin and related compounds. Biosci. Biotechnol. Biochem., 60, 108-110 (1996).
  • 19) Umeda-Sawada, R., Takahashi, N., and Igarashi, O., Interaction of sesamin and eicosapentaenoic acid against Δ5 desaturation and n-6/n-3 ratio of essential fatty acids in rat. Biosci. Biotechnol. Biochem., 59, 2268-2273 (1995).
  • 20) Luthria, D. L., Mohammed, B. S., and Sprecher, H., Regulation of the biosynthesis of 4,7,10,13,16,19-docosahexaenoic acid. J. Biol. Chem., 271, 16020-16025 (1996).
  • 21) Moore, S. A., Hurt, E., Yoder, E., Sprecher, H., and Spector, A. A., Docosahexaenoic acid synthesis in human skin fibroblasts involves peroxisomal retroconversion of tetracosahexaenoic acid. J. Lipid Res., 36, 2433-2443 (1995).
  • 22) Voss, A., Reinhart, M., Sankarappa, S., and Sprecher, H., The metabolism of 7,10,13,16,19-docosapentaenoic acid to 4,7,10,13,16,19-docosahexaenoic acid in rat liver is independent of a 4-desaturase. J. Biol. Chem., 266, 19995-20000 (1991).
  • 23) Jareonkitmongkol, S., Shimizu, S., and Yamada, H., Fatty acid desaturation-defective mutants of an arachidonic-acid-producing fungus, Mortierella alpina 1S-4. J. General Microbiology, 138, 997-1002 (1992).
  • 24) Cham, B. E. and Knowles, B. R., A solvent system for delipidation of plasma or serum without protein precipitation. J. Lipid Res., 17, 176-181 (1976).
  • 25) Coon, H. G. and Weiss, N. C., A quantitative composition of formation of spontaneous and virus-produced viable hybrids. Proc. Natl. Acad. Sci. USA, 62, 852-859 (1969).
  • 26) Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the folin phenol reagent. J. Biol. Chem., 193, 265-275 (1951).
  • 27) Folch, J., Leesm, M., and Sloane-Stanley, G. H., A simple method for isolation and purification of total lipids from animal tissue. J. Biol. Chem., 226, 497-509 (1957).
  • 28) Andersson, B. Å. and Holman, R. T., Pyrrolidides for mass spectrometric determination of the position of the double bond in monounsaturated fatty acids. Lipids, 9, 185-190 (1973).
  • 29) Christie, W. W., Brechany, E. Y., Johnson, S. B., and Holman, R. T., A comparison of pyrrolidide and picolinyl ester derivatives for the identification of fatty acids in natural samples by gas chromatography-mass spectrometry. Lipids, 21, 657-661 (1986).

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