Conjugated Linoleic Acid Oils
Rakesh Kapoor
Bioriginal Food and Science Corp., Saskatoon, Saskatchewan, Canada
Search for more papers by this authorMartin Reaney
Bioriginal Food and Science Corp., Saskatoon, Saskatchewan, Canada
Search for more papers by this authorRakesh Kapoor
Bioriginal Food and Science Corp., Saskatoon, Saskatchewan, Canada
Search for more papers by this authorMartin Reaney
Bioriginal Food and Science Corp., Saskatoon, Saskatchewan, Canada
Search for more papers by this authorAbstract
Conjugated linoleic acid (CLA) is a name given to a mixture of geometric and positional isomers of linoleic acid having conjugated double bonds. Depending on the position and cis-trans-configuration of conjugated double bonds, 54 isomers are possible, of which 14 isomers have been identified in commercial products. CLA was first produced in 1935 via alkali treatment of polyunsaturated fatty acid-rich oils. The early research used CLA mainly as a marker for the study of fat metabolism because of its high UV absorbency compared with nonconjugated fat. From the 1980s, the research interest has increased in its biological properties, particularly its role in cancer, diabetes, and fat metabolism regulation. The present article discusses the metabolism, uses, method of production, and analysis of CLA.
References
- 1Dann, W.J. and Moore, T. (1933). Biochem. J. 27: 1166–1169.
- 2Kapoor, R., Westcott, N.D., Reaney, M.J.T., and Jones, S. (2003). Inform. 14: 482–484.
- 3Reaney, M.J.T., Westcott, N.D., Kapoor, R., and Jones, S. (2002). Inform. 13: 802–807.
- 4Dann, W.J., Moore, T., Booth, R.L. et al. (1935). Biochem. J. 29: 138–146.
- 5Reiser, R. (1951). Arch. Biochem. Biophys. 32: 113–120.
- 6Parodi, P.W. (1977). J. Dairy Sci. 60: 1550–1553.
- 7Miller, E.S. and Burr, G.O. (1937). Proc. Soc. Exp. Biol. Med. 36: 726–729.
- 8Aaes-Jorgensen, E. (1958). J. Nutr. 66: 465–483.
- 9Reiser, R. (1950). Proc. Soc. Exp. Biol. Med. 74: 666–669.
- 10Barnes, R.H., Miller, E.S., and Burr, G.O. (1941). Proc. Soc. Exp. Biol. Med. 45: 233–240.
- 11Belury, M.A. and Kempa-Steczko, A. (1997). Lipids 32: 199–204.
- 12Ip, C., Jiang, C., Thompson, H.J., and Scimeca, J.A. (1997). Carcinogenesis 18: 755–759.
- 13Sebedio, J.L., Angioni, E., Chardigny, J.M. et al. (2001). Lipids 36: 575–582.
- 14Kramer, J.K., Sehat, N., Dugan, M.E. et al. (1998). Lipids 33: 549–558.
- 15Shen, W., Chuang, C.C., Martinez, K. et al. (2013). J. Lipid Res. 54: 909–922.
- 16Sebedio, J.L., Juaneda, P., Dobson, G. et al. (1997). Biochim. Biophys. Acta 1345: 5–10.
- 17Sebedio, J.L., Gnaedig, S., and Chardigny, J.M. (1999). Curr. Opin. Clin. Nutr. Metab. Care 2: 499–506.
- 18Sebedio, J.L., Juaneda, P., Gregoire, S. et al. (1999). Lipids 34: 1319–1325.
- 19Bretillon, L., Chardigny, J.M., Gregoire, S. et al. (1999). Lipids 34: 965–969.
- 20Urquhart, P., Parkin, S.M., Rogers, J.S. et al. (2002). Biochim. Biophys. Acta 1580: 150–160.
- 21Holman, R.T. (1951). Proc. Soc. Exp. Biol. Med. 76: 100–102.
- 22Akahoshi, A., Goto, Y., Murao, K. et al. (2002). Biosci. Biotechnol. Biochem. 66: 916–920.
- 23Ostrowska, E., Suster, D., Muralitharan, M. et al. (2003). Br. J. Nutr. 89: 219–229.
- 24Yamasaki, M., Ikeda, A., Oji, M. et al. (2003). Nutrition 19: 30–35.
- 25Blankson, H., Stakkestad, J.A., Fagertun, H. et al. (2000). J. Nutr. 130: 2943–2948.
- 26Riserus, U., Berglund, L., and Vessby, B. (2001). Int. J. Obes. Relat. Metab. Disord. 25: 1129–1135.
- 27Thom, E., Wadstein, J., and Gudmundsen, O. (2001). J. Int. Med. Res. 29: 392–396.
- 28Belury, M.A., Mahon, A., and Banni, S. (2003). J. Nutr. 133: 257S–260S.
- 29Zambell, K.L., Keim, N.L., Van Loan, M.D. et al. (2000). Lipids 35: 777–782.
- 30Madry, E., Chudzicka-Strugala, I., Grabanska-Martynska, K. et al. (2016). Acta Sci.Pol. Technol. Aliment. 15: 107–113.
- 31Larson, T.M., Toubro, S., Goudmundsen, O., and Astrup, A. (2006). AJCN 83: 606–612.
- 32Kamphuis, M.M., Lejeune, M.P., Saris, W.H., and Westerterp-Plantenga, M.S. (2003). Int. J. Obes. Relat. Metab. Disord. 27: 840–847.
- 33Kim, J.H., Kim, Y., Kim, Y.J., and Park, Y. (2016). Annu. Rev. Food Sci. Technol. 7: 221–244.
- 34Namazi, N., Irandoost, P., Larijani, B., and Azadbakht, L. (2019). Crit. Rev. Food Sci. Nutr. 22: 1–14.
- 35Park, Y., Albright, K.J., Liu, W. et al. (1997). Lipids 32: 853–858.
- 36Brown, J.M. and McIntosh, M.K. (2003). J. Nutr. 133: 3041–3046.
- 37De Deckere, E.A., van Amelsvoort, J.M., McNeill, G.P., and Jones, P. (1999). Br. J. Nutr. 82: 309–317.
- 38Park, Y., Storkson, J.M., Albright, K.J. et al. (1999). Lipids 34: 235–241.
- 39Kang, K. and Pariza, M.W. (2001). Biochem. Biophys. Res. Commun. 287: 377–382.
- 40Nagao, K., Wang, Y.M., Inoue, N. et al. (2003). Nutrition 19: 652–656.
- 41Kang, K., Liu, W., Albright, K.J. et al. (2003). Biochem. Biophys. Res. Commun. 303: 795–799.
- 42Brown, J.M., Boysen, M.S., Jensen, S.S. et al. (2003). J. Lipid. Res. 44: 1287–1300.
- 43Tsuboyama-Kasaoka, N., Takahashi, M., Tanemura, K. et al. (2000). Diabetes 49: 1534–1542.
- 44Tsuboyama-Kasaoka, N., Miyazaki, H., Kasaoka, S., and Ezaki, O. (2003). J. Nutr. 133: 1793–1799.
- 45Riserus, U., Arner, P., Brismar, K., and Vessby, B. (2002). Diabetes Care 25: 1516–1521.
- 46Pariza, M.W. and Hargraves, W.A. (1985). Carcinogenesis 6: 591–593.
- 47Ha, Y.L., Grimm, N.K., and Pariza, M.W. (1987). Carcinogenesis 8: 1881–1887.
- 48Ha, Y.L., Storkson, J., and Pariza, M.W. (1990). Cancer Res. 50: 1097–1101.
- 49Shultz, T.D., Chew, B.P., and Seaman, W.R. (1992). Anticancer Res. 12: 2143–2145.
- 50Ip, C., Singh, M., Thompson, H.J., and Scimeca, J.A. (1994). Cancer Res. 54: 1212–1215.
- 51Lavillonniere, F., Chajes, V., Martin, J.C. et al. (2003). Nutr. Cancer 45: 190–194.
- 52Cesano, A., Visonneau, S., Scimeca, J.A. et al. (1998). Anticancer Res. 18: 1429–1434.
- 53Cheng, J.L., Futakuchi, M., Ogawa, K. et al. (2003). Cancer Lett. 196: 161–168.
- 54Park, H.S., Ryu, J.H., Ha, Y.L., and Park, J.H. (2001). Br. J. Nutr. 86: 549–555.
- 55Durgam, V.R. and Fernandes, G. (1997). Cancer Lett. 116: 121–130.
- 56Kavanaugh, C.J., Liu, K.L., and Belury, M.A. (1999). Nutr. Cancer 33: 132–138.
- 57Cho, H.J., Kim, W.K., Kim, E.J. et al. (2003). Am. J. Physiol. Gastrointest. Liver Physiol. 284: G996–G1005.
- 58Miller, A., Stanton, C., and Devery, R. (2002). Anticancer Res. 22: 3879–3887.
- 59Masso-Welch, P.A., Zangani, D., Ip, C. et al. (2004). J. Nutr. 134: 299–307.
- 60Ip, C., Dong, Y., Thompson, H.J. et al. (2001). Nutr. Cancer 39: 233–238.
- 61Ip, C., Scimeca, J.A., and Thompson, H. (1995). Nutr. Cancer 24: 241–247.
- 62Aro, A., Mannisto, S., Salminen, I. et al. (2000). Nutr. Cancer 38: 151–157.
- 63McGowan, M.M., Eisenberg, B.L., Lewis, L.D. et al. (2013). Breast Cancer Res. Treat. 138: 175–183.
- 64Martel, P.M., Bingham, C.M., McGraw, C.J. et al. (2006). Exp. Cell Res. 312: 278–288.
- 65den Hartigh, L.J. (2019). Nutrients 11: 370. doi: 10.3390/nu11020370.
- 66Houseknecht, K.L., Vanden Heuvel, J.P., Moya-Camarena, S.Y. et al. (1998). Biochem. Biophys. Res. Commun. 244: 678–682.
- 67Ryder, J.W., Portocarrero, C.P., Song, X.M. et al. (2001). Diabetes 50: 1149–1157.
- 68Clement, L., Poirier, H., Niot, I. et al. (2002). J. Lipid Res. 43: 1400–1409.
- 69Hargrave, K.M., Azain, M.J., Kachman, S.D., and Miner, J.L. (2003). Obes. Res. 11: 1104–1115.
- 70Nagao, K., Inoue, N., Wang, Y.M., and Yanagita, T. (2003). Biochem. Biophys. Res. Commun. 310: 562–566.
- 71Ostrowska, E., Cross, R.F., Muralitharan, M. et al. (2002). Br. J. Nutr. 88: 625–634.
- 72Noone, E.J., Roche, H.M., Nugent, A.P., and Gibney, M.J. (2002). Br. J. Nutr. 88: 243–251.
- 73Garibay-Nieto, N., Queipo-Garcia, G., Alvarez, F. et al. (2017). J. Clin. Endocrinol Metab. 102: 132–140.
- 74Lee, K.N., Kritchevsky, D., and Pariza, M.W. (1994). Atherosclerosis 108: 19–25.
- 75Kritchevsky, D., Tepper, S.A., Wright, S. et al. (2000). Coll. Nutr. 19: 472S–477S.
- 76Nicolosi, R.J., Rogers, E.J., Kritchevsky, D. et al. (1997). Artery 22: 266–277.
- 77Gavino, V.C., Gavino, G., Leblanc, M.J., and Tuchweber, B. (2000). J. Nutr. 130: 27–29.
- 78Yu-Poth, S., Yin, D., Zhao, G. et al. (2004). J. Nutr. 134: 68–71.
- 79Pariza, M.W. and Lee, K.N. (1998). (assigned to, Madison, Wisconsin). U.S. Patent 5, 837, 733, 1998.
- 80Toomey, S., Roche, H., Fitzgerald, D., and Belton, O. (2003). Biochem. Soc. Trans. 31: 1075–1079.
- 81Truitt, A., McNeill, G., and Vanderhoek, J.Y. (1999). Biochim. Biophys. Acta 1438: 239–246.
- 82Nagao, K., Inoue, N., Wang, Y.M. et al. (2003). Biochem. Biophys. Res. Commun. 306: 134–138.
- 83Benito, P., Nelson, G.J., Kelley, D.S. et al. (2001). Lipids 36: 229–236.
- 84Sluijs, I., Plantinga, Y., De Roose, B. et al. (2010). Am. J. Clin. Nutr. 91: 175–183.
- 85Pfeuffer, M., Fielitz, K., Laue, C. et al. (2011). J. Am. Coll. Nutr. 30: 19–28.
- 86Cook, M.E., Ellen, B., Stahl, J.L. et al. (1996). (assigned to, Madison, Wisconsin). U.S. Patent 5, 585, 400, 1996.
- 87Cook, M.E., Pariza, M.W., Yang, X., and De Voney, D. (1997). (assigned to, Madison, Wisconsin), U.S. Patent 5, 674, 901, 1997.
- 88Hayek, M.G., Han, S.N., Wu, D. et al. (1999). J. Nutr. 129: 32–38.
- 89Whigham, L.D., Cook, E.B., Stahl, J.L. et al. (2001). Am. J. Physiol. Regul. Integr. Comp. Physiol. 280: R908–R912.
- 90Wong, M.W., Chew, B.P., Wong, T.S. et al. (1997). Anticancer Res. 17: 987–993.
- 91Cook, M.E., Kim, S., Pariza, M.W., and De Voney, D. (1999). (assigned to, Madison, Wisconsin), U.S. Patent 5, 914, 346, 1999.
- 92Yu, Y., Correll, P.H., and Vanden Heuvel, J.P. (2002). Biochim. Biophys. Acta 1581: 89–99.
- 93Bassaganya-Riera, J., Hontecillas, R., Zimmerman, D.R., and Wannemuehler, M.J. (2002). Vaccine 20: 1435–1444.
- 94Bassaganya-Riera, J., Pogranichniy, R.M., Jobgen, S.C. et al. (2003). J. Nutr. 133: 3204–3214.
- 95Bontempo, V., Sciannimanico, D., Pastorelli, G. et al. (2004). J. Nutr. 134: 817–824.
- 96Kelley, D.S., Taylor, P.C., Rudolph, I.L. et al. (2000). Lipids 35: 1065–1071.
- 97Kelley, D.S., Simon, V.A., Taylor, P.C. et al. (2001). Lipids 36: 669–674.
- 98Cheng, W.L., Lii, C.K., Chen, H.W. et al. (2004). J. Agric. Food Chem. 52: 71–78.
- 99Cook, M.E., Pariza, M.W., Lee, K.N., and Wentworth, B.C. (1996). (assigned to, Madison, Wisconsin). U.S. Patent 5, 504, 114, 1996.
- 100Stock, R.H. and Compton, J.D. (2001). (assigned to, Princeton, New Jersey). U.S. Patent 6, 316, 041, 2001.
- 101Cook, M.E., Rahim, A., and Pariza, M.W. (2000). (assigned to, Madison, Wisconsin). U.S. Patent 6, 113, 973, 2000.
- 102Kelly, M.L., Berry, J.R., Dwyer, D.A. et al. (1998). J. Nutr. 128: 881–885.
- 103Nurmela, K. and Griinari, M. (2003). (assigned to, Helsinki, Finland). U.S. Patent 6, 635, 271, 2003.
- 104Ward, A.T., Wittenberg, K.M., Froebe, H.M. et al. (2003). J. Dairy Sci. 86: 1742–1750.
- 105Dhiman, T.R., Anand, G.R., Satter, L.D., and Pariza, M.W. (1999). J. Dairy Sci. 82: 2146–2156.
- 106Dhiman, T.R., Helmink, E.D., McMahon, D.J. et al. (1999). J. Dairy Sci. 82: 412–419.
- 107Dhiman, T.R., Satter, L.D., Pariza, M.W. et al. (2000). J. Dairy Sci. 83: 1016–1027.
- 108Ward, A.T., Wittenberg, K.M., and Przybylski, R. (2002). J. Dairy Sci. 85: 1191–1196.
- 109Whitlock, L.A., Schingoethe, D.J., Hippen, A.R. et al. (2002). J. Dairy Sci. 85: 234–243.
- 110Loor, J.J. and Herbein, J.H. (1998). J. Nutr. 128: 2411–2419.
- 111Franklin, S.T., Martin, K.R., Baer, R.J. et al. (1999). J. Nutr. 129: 2048–2054.
- 112Christie, W.W., Dobson, G., and Gunstone, F.D. (1997). Lipids 32: 1231.
- 113Mounts, T.L. and Dutton, H.L. (1970). Lipids 5: 997–1005.
- 114Johnson, R.W. and Daniels, R.W. (1996). In: Encyclopedia of Chemical Technology, 4e (ed. K. Othmer), 168–177. New York: Wiley.
- 115 Henkel Corporation (1991). Specifications and characteristics of Emery oleochemicals, Technical Bulletin A-473. Cincinnati, Ohio: Henkel Corporation, Emery Group.
- 116Padley, F.B., Gunstone, F.D., and Harwood, F.B. (1994). In: The Lipid Handbook, 2e (ed. F.D. Gunstone, H. Hashimoto and F.B. Padley), 47–224. London: Chapman and Hall.
- 117Fritz, E. and Johnson, R.W. (1988). Fatty Acids in Industry. New York: Marcel Dekker.
- 118Gunstone, F.D., Kates, M., and Harwood, J.L. (1994). In: The Lipid Handbook, 2e (ed. F.D. Gunstone, J.L. Harwood and F.B. Padley), 47–224. London: Chapman and Hall.
- 119Keulemans, C. (1990). In: Patent.
- 120Cleary, M.T., Kulprathipanja, S., and Neuzil, R.W. (1985). (assigned to, Des Plaines, Illinois). U.S. Patent 4, 524, 029, 1985.
- 121Cleary, M.T. and Kulprathipanja, M. T. (1982). (assigned to, Des Plaines, Illinois). U.S. Patent 4, 353, 838, 1982.
- 122Kirshner, H.G. (1945). (assigned to, Jersey City, New Jersey). U.S. Patent 2, 389, 260, 1945.
- 123Burr, G.O. (1941). U.S. Patent 2, 242, 230, 1941.
- 124Cawley, J.D. (1944). U.S. Patent 2, 343, 644, 1944.
- 125Struve, A. (1983). (assigned to, Dusseldorf-Holthausen, Denmark). U.S. Patent 4, 381, 264 1983.
- 126Bradley, T.F. (1944). U.S. Patent 2, 350, 583, 1944.
- 127Krajca, K.E.(1979). (assigned to, Jacksonville, Florida). U.S. Patent 4, 164, 505, 1979.
- 128Bradley, T.F. and Richardson, D. (1942). Ind. Eng. Chem. 34: 237–242.
- 129Nichols, P.L., Riemenschneider, R.W., and Herb, S.F. (1950). J. Am. Chem. Soc. 27: 329–336.
- 130Reaney, M.J.T., Liu, M.M., and Westcott, N.D. (1999). In: Advances in Conjugated Linoleic Acid Research (ed. M.P. Yurawecz, M.M. Mossoba, J.K. Kramer, et al.), 39–54. Champaign, Illinois: AOCS Press.
- 131Saebo, A. (2003). In: Advances in Conjugated Linoleic Acid Research (ed. J.L. Sebedio, W.W. Christie and R. Adolf), 71–81. Champaign, Illinois: AOCS Press.
- 132Richardson, T.A. (1993). Industrial Plastics: Theory and Application. Cincinnati, Ohio: South West Publishing Co.
- 133Pariza, M.W. and Yang, Y.M. (1999). (assigned to, Madison, Wisconsin). U.S. Patent 5, 856, 149, 1999.
- 134Solomon, D.H. (1977). The Chemistry of Natural Film Formers, 2e, 33–74. Huntington, New York: Robert E. Krieger Publishing Co.
- 135Zabolotskij, D.A., Demin, P.M., and Mylagkoya, G.I., Russian Patent 2021, 252, 1994.
- 136Lie Ken, M.S.F., Jie, M.K.P., and Alam, M.S. (1977). Lipids 32: 1041–1044.
10.1007/s11745-997-0134-9 Google Scholar
- 137Sehat, N., Yurawecz, M.P., Roach, J.A. et al. (1998). Lipids 33: 217–221.
- 138Sehat, N., Rickert, R., Mossoba, M.M. et al. (1999). Lipids 34: 407–413.
- 139Booth, R.L., Kon, S.K., Dann, W.J., and Moore, T. (1935). Biochem. J. 29: 133–137.
- 140Czauderna, M. and Kowalczyk, J. (2001). J. Chromatogr. B. Biomed. Sci. Appl. 760: 165–178.
- 141Jackson, J.E., Paschke, R.F., Tolberg, W. et al. (1952). Oil Chem. Soc. 29: 229–234.
- 142Mossoba, M.M., Yurawecz, M.P., Kramer, J.K. et al. (1999). In: Advances in Conjugated Linoleic Acid Research (ed. M.P. Yurawecz, M.M. Mossoba, J.K. Kramer, et al.), 141–151. Champaign, Illinois: AOCS Press.
- 143Fritsche, J., Mossoba, M.M., Yurawecz, M.P. et al. (1997). Unters Forsch. A 205: 415–418.
- 144Ackman, R.G., Eaton, C.A., Sipos, J.C., and Crew, N.F. (1981). J. Can. Inst. Food Sci. Technol. 14: 103–107.
- 145Yurawecz, M.P., Kramer, J.K., and Ku, Y. (1999). In: Advances in Conjugated Linoleic Acid Research (ed. M.P. Yurawecz, M.M. Mossoba, J.K. Kramer, et al.), 64–82. Champaign, Illinois: AOCS Press.
- 146Ostrowska, E., Dunshea, F.R., Muralitharan, M., and Cross, R.F. (2000). Lipids 35: 1147–1153.
- 147Werner, S.A., Luedecke, L.O., Shultz, T.D., and Agric, J. (1992). Food Chem. 40: 1817–1821.
- 148Kramer, J.K., Fellner, V., Dugan, M.E. et al. (1997). Lipids 32: 1219–1228.
- 149Park, Y., Albright, K.J., Cai, Z.Y., and Pariza, M.W. (2001). J. Agric. Food Chem. 49: 1158–1164.
- 150Eulitz, K., Yurawecz, M.P., Sehat, N. et al. (1999). Lipids 34: 873–877.
- 151Spitzer, V. (1999). In: Advances in Conjugated Linoleic Acid Research (ed. M.P. Yurawecz, M.M. Mossoba, M.W. Pariza and G.J. Nelson), 110–125. Champaign, Illinois: AOCS Press.
- 152Janssen, G. and Paramentier, G. (1978). Biomed. Mass Spectrom. 5: 439–443.
- 153Reaney, M.J.T., Dong, L.Y., Taylor, W.G., and Amer, J. (2001). Oil Chem. Soc. 78: 1083–1086.
- 154Lie Ken, M.S.F., Jie, M.K.P., and Alam, M.S. (1999). In: Advances in Conjugated Linoleic Acid Research (ed. M.P. Yurawecz, M.M. Mossoba, J.K. Kramer, et al.), 152–163. Champaign, Illinois: AOCS Press.
- 155Davis, A.L., McNeill, G.P., and Caswell, D.C. (1999). In: Advances in Conjugated Linoleic Acid Research, vol. 1 (ed. M.P. Yurawecz, M.M. Mossoba, J.K. Kramer, et al.), 164–179. Champaign, Illinois: AOCS Press.
- 156Davis, A.L., McNeill, G.P., and Caswell, D.C. (1999). Chem. Phys. Lipids 97: 155–165.
- 157Jie, M.S., Pasha, M.K., and Alam, M.S. (1997). Lipids 32: 1041–1044.
- 158Brice, B.A., Swain, S.F., Herb, S.F. et al. (1949). J. Am. Oil Chem. Soc. 29: 279–287.
- 159Ritz, J. and Reese, J. (1976). (assigned to, Frankfurt, Germany). U.S. Patent 3, 984, 444, 1976.