1932

Abstract

Conjugated linoleic acid (CLA) is in ruminant-derived foods and is known to combat obesity-related diseases. However, CLA levels in a healthy diet are too low to produce a clinical effect. Therefore, CLA has been produced by linoleic isomerization through fermentation and chemical catalysis. Many of these techniques are not practical for food production, but a recent development has enabled production of CLA-rich triglyceride vegetable oils from high linoleic acid oils by a minor modification of conventional food-oil processing techniques. These oils were used to produce common lipid-based food, such as margarine, shortenings, and salad dressings, whose quality was enhanced by the presence of CLA-rich oil and provided a significant CLA source. Meat and egg CLA content and subsequent food quality can also be increased by addition of dietary CLA. However, consumer awareness of CLA benefits needs to increase prior to commercial-scale production of CLA-rich oil.

Loading

Article metrics loading...

/content/journals/10.1146/annurev-food-030216-025703
2017-02-28
2024-04-26
Loading full text...

Full text loading...

/deliver/fulltext/food/8/1/annurev-food-030216-025703.html?itemId=/content/journals/10.1146/annurev-food-030216-025703&mimeType=html&fmt=ahah

Literature Cited

  1. Ahn DU, Sell JL, Jo C, Chamruspollert M, Jeffrey M. 1999. Effect of dietary conjugated linoleic acid on the quality characteristics of chicken eggs during refrigerated storage. Poult. Sci. 78:922–28 [Google Scholar]
  2. Aletor VA, Eder K, Becker K, Paulicks BR, Roth FX, Roth-Maier DA. 2003. The effects of conjugated linoleic acids or an alpha-glucosidase inhibitor on tissue lipid concentrations and fatty acid composition of broiler chicks fed a low-protein diet. Poult. Sci. 82:796–804 [Google Scholar]
  3. Alonso L, Cuesta EP, Gilliland SE. 2003. Production of free conjugated linoleic acid by Lactobacillusacidophilus and Lactobacillus casei of human intestinal origin. J. Dairy Sci. 86:1941–46 [Google Scholar]
  4. Andjelkovic DD, Min B, Ahn D, Larock RC. 2006. Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils. J. Agric. Food Chem. 54:9535–43 [Google Scholar]
  5. Aydin R, Pariza MW, Cook ME. 2001. Olive oil prevents the adverse effects of dietary conjugated linoleic acid on chick hatchability and egg quality. J. Nutr. 131:800–6 [Google Scholar]
  6. Aydin R. 2007. The effects of conjugated linoleic acid (CLA) and canola oil on the fatty acid composition and quality of eggs from laying hens. S. Afr. J. Anim. Sci. 35:3172–79 [Google Scholar]
  7. Badiani A, Montellato L, Bochicchio D, Anfossi P, Zanardi E, Maranesi M. 2004. Selected nutrient contents, fatty acid composition, including conjugated linoleic acid, and retention values in separable lean from lamb rib loins as affected by external fat and cooking method. J. Agric. Food Chem. 52:5187–94 [Google Scholar]
  8. Barret A, Ross RP, Fitzgerald GF, Stanton C. 2007. Rapid screening method for analyzing the conjugated linoleic acid production capabilities of bacterial cultures. Appl. Environ. Microbiol. 73:2333–37 [Google Scholar]
  9. Bassaganya-Riera J, Hontecillas R, Horne WT, Sandridge M, Herfarth HH. et al. 2012. Conjugated linoleic acid modulates immune responses in patients with mild to moderately active Crohn's disease. Clin. Nutr. 31:721–27 [Google Scholar]
  10. Basu A, Kasar TG. 1986. Catalytic isomerization of safflower oil with rhodium complexes. J. Am. Oil Chem. Soc. 63:1444–46 [Google Scholar]
  11. Bauer P, Horlacher P, Claus P. 2009. Direct isomerization of linoleic acid to conjugated linoleic acids (CLA) using gold catalysts. Chem. Eng. Technol. 32:2005–10 [Google Scholar]
  12. Bee G. 2001. Dietary conjugated linoleic acids affect tissue lipid composition but not de novo lipogenesis in finishing pigs. Anim. Res. 50:383–99 [Google Scholar]
  13. Behra A, Witte H, Bayrak Z. 2013. Homogenous metal complex catalyzed conjugation of methyl linoleate. Eur. J. Lipid Sci. Technol. 115:721–28 [Google Scholar]
  14. Bernas A, Kumar N, Mäki-Arvela P, Kul′kova NV, Holmbom B. et al. 2003. Isomerization of linoleic acid over supported metal catalysts. Appl. Catal. A. 245:257–75 [Google Scholar]
  15. Bernas A, Kumar N, Laukkanen P, Väyrynen J, Salmi T, Murzin DY. 2004. Influence of ruthenium precursor on catalytic activity of Ru/Al2O3 catalyst in selective isomerization of linoleic acid to cis-9,. trans -11- and trans-10, cis-12-conjugated linoleic acid. Appl. Catal. A. 267:121–33 [Google Scholar]
  16. Bernas A, Murzin DY. 2005. Linoleic acid isomerization on Ru/Al2O3 catalyst: 2. Elementary step mechanism and data fitting. Chem. Eng. J. 115:23–43 [Google Scholar]
  17. Bradley TF, Richardson D. 1942. Alkali-induced isomerization of drying oils and fatty acids. Ind. Eng. Chem. 34:237–42 [Google Scholar]
  18. Bradley TF. 1944. Drying oils. US Patent No. 2350583
  19. Castro-Webb N, Ruiz-Narváez EA, Campos H. 2012. Cross-sectional study of conjugated linoleic acid in adipose tissue and risk of diabetes. Am. J. Clin. Nutr. 96:175–81 [Google Scholar]
  20. Chamruspollert M, Sell JL. 1999. Transfer of dietary conjugated linoleic acid to egg yolks of chickens. Poult. Sci. 78:1138–50 [Google Scholar]
  21. Chintareddy VR, Oshel RE, Doll KM, Yu ZK, Wu W. et al. 2012. Investigation of conjugated soybean oil as drying oils and CLA sources. J. Am. Oil Chem. Soc. 89:1749–62 [Google Scholar]
  22. Choi BD, Kang SJ, Ha YL, Ackman RG. 1999. Accumulation of conjugated linoleic acid (CLA) in tissues of fish fed diets containing various levels of CLA. Quality Attributes of Muscle Foods C-T Ho, F Shahidi 61–71 New York: Springer [Google Scholar]
  23. Choi NJ, Park HG, Kim YJ, Kim IH, Kang HS. et al. 2008. Utilization of monolinolein as a substrate for conjugated linoleic acid production by Bifidobacterium breve LMC 520 of human neonatal origin. J. Agric. Food Chem. 56:10908–12 [Google Scholar]
  24. Chorfa N, Hamoudi S, Arul J, Belkacemi K. 2013. Sulfur promotion in conjugated isomerization of safflower oil over bifunctional structured Rh/SBA-15 catalysts. ChemCatChem 5:1917–34 [Google Scholar]
  25. Chung SH, Kim IH, Park HG, Kang HS, Yoon CS. et al. 2008. Synthesis of conjugated linoleic acid by human-derived Bifidobacterium breve LMC 017: utilization as a functional starter culture for milk fermentation. J. Agric. Food Chem. 56:3311–16 [Google Scholar]
  26. Claus P. 2005. Heterogeneously catalysed hydrogenation using gold catalysts. Appl. Catal. A. 291:222–29 [Google Scholar]
  27. Coakley M, Ross RP, Nordgren M, Fitzgerald G, Devery R, Stanton C. 2003. Conjugated linoleic acid biosynthesis by human-derived Bifidobacterium species. J. Appl. Microbiol. 94:138–45 [Google Scholar]
  28. Cowan JC. 1949. Isomerization reactions of drying oils. Ind. Eng. Chem. 41:294–304 [Google Scholar]
  29. Dannenberger D, Nuernberg G, Scollan N, Schabbel W, Steinhart H. et al. 2004. Effect of diet on the deposition of n-3 fatty acids, conjugated linoleic and C18:1 trans fatty acid isomers in muscle lipids of German Holstein bulls. J. Agric. Food Chem. 21:6607–15 [Google Scholar]
  30. DeJarlais WJ, Gast LE. 1971. Conjugation of polyunsaturated fats: activity of some group VIII metal compounds. J. Am. Oil Chem. Soc. 48:157–59 [Google Scholar]
  31. Deshpande VM, Gadkari RG, Mukesh D, Narasimhan CS. 1985. Studies on kinetics of catalytic isomerization of methyl linoleate. J. Am. Oil Chem. Soc. 62:734–38 [Google Scholar]
  32. Dianóczki C, Kovari J, Novak L, Poppe L, Recseg K. 2007. Method for the preparation of conjugated linoleic acid. US Patent No. 0078274 A1
  33. Dilzer A, Park Y. 2012. Implication of conjugated linoleic acid (CLA) in human health. Crit. Rev. Food Sci. Nutr. 52:488–513 [Google Scholar]
  34. Du M, Ahn DU. 2002. Effect of dietary conjugated linoleic acid on the growth rate of live birds and on the abdominal fat content and quality of broiler meat. Poult. Sci. 3:428–33 [Google Scholar]
  35. Faukner J, Rawles SD, Proctor A, Sink TD, Chen R. et al. 2013. The effects of diets containing standard soybean oil, soybean oil enhanced with conjugated linoleic acids, menhaden fish oil, or an algal docosahexaenoic acid supplement on channel catfish performance, body composition, sensory evaluation, and storage characteristics. N. Am. J. Aquac. 75:2252–65 [Google Scholar]
  36. French P, Stanton C, Lawless F, O'Riordan EG, Monahan FJ. et al. 2000. Fatty acid composition, including conjugated linoleic acid, of intramuscular fat from steers offered grazed grass, grass silage, or concentrate-based diets. J. Anim. Sci. 78:2849–55 [Google Scholar]
  37. Gatlin LA, See MT, Larick DK, Lin X, Odle J. 2002. Conjugated linoleic acid in combination with supplemental dietary fat alters pork fat quality. J. Nutr. 132:3105–12 [Google Scholar]
  38. Gangidi RR, Lokesh BR. 2014. Conjugated linoleic acid (CLA) formation in edible oils by photoisomerization: a review. J. Food Sci. 79:781–85 [Google Scholar]
  39. Gangidi RR, Proctor A. 2004. Photochemical production of conjugated linoleic acid from soybean oil. Lipids 39:577–82 [Google Scholar]
  40. Gebauer SK, Chardigny JM, Jakobsen MU, Lamarche B, Lock AL. et al. 2011. Effects of ruminant trans fatty acids on cardiovascular disease and cancer: a comprehensive review of epidemiological, clinical, and mechanistic studies. Adv. Nutr. 2:332–54 [Google Scholar]
  41. Geboers J, Goossens S, Philippaerts A, Sels B. 2013. Method for the production of conjugated polyunsaturated fatty acids with heterogeneous catalysts. US Patent No. 0245299 A1
  42. Ghisalberti C. 2001. Process for the preparation of conjugated linoleic acid (CLA). Patent No. WO2001018161
  43. Gorissen L, Leroy F, De Vuyst L, De Smet S, Raes K. 2015. Bacterial production of conjugated linoleic acid and linolenic acid. Crit. Rev. Food Sci. Nutr. 55:1561–74 [Google Scholar]
  44. Goli SA, Sahri MM, Kadivar M, Keramat J. 2009. The production of an experimental table margarine enriched with conjugated linoleic acid (CLA): physical properties. J. Am. Oil Chem. Soc. 86:453–58 [Google Scholar]
  45. Gorissen L, Raes K, De Smet S, De Vuyst L, Leroy F. 2012. Microbial production of conjugated linoleic acid and linolenic acids in fermented foods: technological bottlenecks. Eur. J. Lipid Sci. Technol. 114:486–91 [Google Scholar]
  46. Gorissen L, Raes K, Weckx S, Dannenberger D, Leroy F. et al. 2010. Production of conjugated linoleic acid and conjugated linolenic acid isomers by Bifidobacterium species. App. Microbiol. Biotechnol. 87:2257–66 [Google Scholar]
  47. Ham JS, In YM, Jeong SG, Kim JG, Lee EH. et al. 2002. Screening of conjugated linoleic acid producing lactic acid bacteria from fecal samples of healthy babies. Asian Australas. J. Anim. Sci. 15:1031–35 [Google Scholar]
  48. Hosseini ES, Kermanshahi RK, Hosseinkhani S, Shojaosadati SA, Nazari M. 2015. Conjugated linoleic acid production from various substrates by probiotic Lactobacillus plantarum. Ann. Microbiol. 65:27–32 [Google Scholar]
  49. Iwata T, Kamegai T, Sato Y, Watanabe K, Kasai M. 1999. Method for producing conjugated linoleic acid. US Patent No. 5986116 A
  50. Jain VP, Proctor A. 2006. Photocatalytic production and processing of conjugated linoleic acid–rich soy oil. J. Agric. Food Chem 54:5590–96 [Google Scholar]
  51. Jain VP, Proctor A. 2007. Kinetics of photoirradiation-induced synthesis of soy oil–conjugated linoleic acid isomers. J. Agric. Food Chem. 55:889–94 [Google Scholar]
  52. Jain VP, Proctor A, Lall R. 2008. Pilot-scale production of conjugated linoleic acid–rich soy oil by photoirradiation. J. Food Sci. 73:E183–92 [Google Scholar]
  53. Jiang J, Björck L, Fondén R. 1998. Production of conjugated linoleic acid by dairy starter cultures. J. Appl. Microbiol. 85:95–102 [Google Scholar]
  54. Ju JW, Jung MY. 2003. Formation of conjugated linoleic acids in soybean oil during hydrogenation with a nickel catalyst as affected by sulfur addition. J. Agric. Food Chem. 51:3144–49 [Google Scholar]
  55. Joo ST, Lee JI, Ha YL, Park GB. 2002. Effects of dietary conjugated linoleic acid on fatty acid composition, lipid oxidation, color, and water-holding capacity of pork loin. J. Anim. Sci. 80:108–12 [Google Scholar]
  56. Khanal RC. 2004. Dietary Influence on Conjugated Linoleic Acid Content of Milk and Consumer Acceptability of Milk and Cheese Naturally Enriched with Conjugated Linoleic Acid Logan, UT: Utah State Dep. Anim. Dairy Vet. Sci.
  57. Khanal RC, Olson KC. 2004. Factors affecting conjugated linoleic acid (CLA) content in milk, meat, and egg: a review. Pak. J. Nutr. 3:82–98 [Google Scholar]
  58. Khosravi A, Safari M, Khodaiyan F, Gharibzahedi S. 2015. Bioconversion enhancement of conjugated linoleic acid by Lactobacillus plantarum using the culture media manipulation and numerical optimization. J. Food Sci. Technol. 52:5781–89 [Google Scholar]
  59. Kim JH, Kim Y, Kim YJ, Park Y. 2016. Conjugated linoleic acid: potential health benefits as a functional food ingredient. Annu. Rev. Food Sci. Technol. 7:221–44 [Google Scholar]
  60. Kishino S, Ogawa J, Matsumura K, Shimizu K. 2002. Conjugated linoleic acid production from linoleic acid by lactic acid bacteria. J. Am. Oil Chem. Soc. 79:159–63 [Google Scholar]
  61. Knight TW, Knowles SO, Death AF, Cummings TL, Muir PD. 2004. Conservation of conjugated linoleic, trans‐vaccenic and long chain omega‐3 fatty acid content in raw and cooked lamb from two cross‐breeds. N. Z. J. Agric. Res. 47:129–35 [Google Scholar]
  62. Krajca KE. 1979. Flow process for conjugating unconjugated unsaturation of fatty acids. US Patent No. 1117138 A1
  63. Kreich M, Claus P. 2005. Direct conversion of linoleic acid over silver catalysts in the presence of H2: an unusual way towards conjugated linoleic acids. Angew. Chem. Int. Ed. 44:7800–4 [Google Scholar]
  64. Krompiec S, Penczek R, Krompiec M, Pluta T, Ignasiak H. et al. 2009. Transition metals for conjugation of polyunsaturated acids and their esters. Curr. Org. Chem. 13:896–913 [Google Scholar]
  65. Krompiec S, Suwiński J, Majewski J, Grobelny J. 1997. Isomerization of vegetable oils catalyzed by dichlorotris(triphenylphosphine)ruthenium(II). Pol. J. Appl. Chem. 41:35–46 [Google Scholar]
  66. Krompiec S, Suwiński J, Majewski J, Grobelny J. 1998. Isomerization of vegetable oils catalyzed by ruthenium complexes. Pol. J. Appl. Chem. 42:43–48 [Google Scholar]
  67. Larock RC, Dong X, Chung S, Reddy CK, Ehlers LE. 2001. Preparation of conjugated soybean oil and other natural oils and fatty acids by homogeneous transition metal catalysis. J. Am. Oil Chem. Soc. 78:447–53 [Google Scholar]
  68. Lauridsen C, Mu H, Henckel P. 2005. Influence of dietary conjugated linoleic acid (CLA) and age at slaughtering on performance, slaughter- and meat quality, lipoproteins, and tissue deposition of CLA in barrows. Meat Sci 69:393–99 [Google Scholar]
  69. Lawson RE, Moss AR, Givens DI. 2001. The role of dairy products in supplying conjugated linoleic acid to man's diet: a review. Nutr. Res. Rev. 14:153–72 [Google Scholar]
  70. Lee HY, Park JH, Seok SH, Baek MW, Kim DJ. et al. 2006. Human originated bacteria, Lactobacillus rhamnosus PL60, produce conjugated linoleic acid and show anti-obesity effects in diet-induced obese mice. Biochem. Biophys. Acta 1761:736–44 [Google Scholar]
  71. Lee K, Paek K, Lee HY, Park JH, Lee Y. 2007. Antiobesity effect of trans-10, cis-12-conjugated linoleic acid–producing Lactobacillus plantarum PL62 on diet-induced obese mice. J. Appl. Microbiol. 103:1140–46 [Google Scholar]
  72. Lee SO, Kim CS, Cho SK, Choi HJ, Ji GE, Kun D. 2003. Bioconversion of linoleic acid into conjugated linoleic acid during fermentation and by washed cells of Lactobacillus reuteri. Biotechnol. Lett. 25:935–38 [Google Scholar]
  73. Li JY, Zhang LW, Du M, Han X, Yi HX. et al. 2011. Effect of Tween series on growth and cis-9, trans-11 conjugated linoleic acid production of Lactobacillus acidophilus F0221 in the presence of bile salts. Int. J. Mol. Sci. 12:9138–54 [Google Scholar]
  74. Liu P, Shen S, Ruan H, Zhou Q, Ma L, He G. 2011. Production of conjugated linoleic acids by Lactobacillus plantarum strains isolated from naturally fermented Chinese pickles. J. Zhejiang Univ. Sci. B 12:923–30 [Google Scholar]
  75. Mayfield S, Proctor A, Shinn SE, Dewettinck K, Patel AR. 2015a. CLA-rich soy oil shortening production and characterization. J. Am. Oil Chem. Soc. 92:1267–75 [Google Scholar]
  76. Mayfield S, Van de Walle D, Delbaere C, Shinn SE, Proctor A. et al. 2015b. CLA-rich chocolate bar and chocolate paste production and characterization. J. Am. Oil Chem. Soc. 92:1633–42 [Google Scholar]
  77. Mir Z, Paterson LJ, Mir PS. 2000. Fatty acid composition and conjugated linoleic acid content of intramuscular fat in crossbred cattle with and without Wagyu genetics fed a barley-based diet. Can. J. Anim. Sci. 80:195–97 [Google Scholar]
  78. Monster J, Yan YC. 2014. Method for producing conjugated linoleic acid. US Patent No. 0113968 A1
  79. Moon HS. 2014. Biological effects of conjugated linoleic acid on obesity-related cancers. Chem. Biol. Interact. 24:189–95 [Google Scholar]
  80. Moore T. 1937. Spectroscopic changes in fatty acids. Biochem. J. 31:138–41 [Google Scholar]
  81. Mukesh D, Naraslmhan S, Gadkarl R, Deshpande VM. 1985. Kinetics and mathematical modeling of isomerization of methyl linoleate on ruthenium catalyst. 1. Conjugation and polymerization. Ind. Eng. Chem. Prod. Res. Dev. 24:318–23 [Google Scholar]
  82. Mukesh D, Narasimhan S, Deshpande VM, Ramnarayan K. 1988. Isomerization of methyl linoleate on supported ruthenium-nickel catalyst. Ind. Eng. Chem. Res. 27:409–14 [Google Scholar]
  83. Oh DK, Hong GH, Lee Y, Min S, Sin HS, Cho SK. 2003. Production of conjugated linoleic acid by isolated Bifidobacterium strains. World J. Microbiol. Biotechnol. 19:907–12 [Google Scholar]
  84. Pariza M, Wand Yang XY. 1999. Method of producing conjugated fatty acids. US Patent No. 5856149
  85. Pariza M, Wand Yang XY. 2000. Method of producing conjugated fatty acids. US Patent No. 6060304
  86. Parodi PW. 2003. Conjugated linoleic acid in food. Adv. Conjug. Linoleic Acid Res. 2:101–22 [Google Scholar]
  87. Park Y. 2009. Conjugated linoleic acid (CLA): good or bad trans-fat?. J. Food Compos. Anal. 22:S4–12 [Google Scholar]
  88. Park HG, Cho SD, Kim JH, Lee H, Chung SH. et al. 2009. Characterization of conjugated linoleic acid production by Bifidobacterium breve LMC 520. J. Agric. Food Chem. 57:571–75 [Google Scholar]
  89. Philippaerts A, Goossens S, Jacobs PA, Sels BF. 2011. Catalytic production of conjugated fatty acids and oils. ChemSusChem 4:684–702 [Google Scholar]
  90. Poulson CS, Dhiman TR, Ure AL, Cornforth D, Olson KC. 2004. Conjugated linoleic acid content of beef from cattle fed diets containing high grain, CLA, or raised on forages. Livest. Prod. Sci. 91:117–28 [Google Scholar]
  91. Proctor A, Shah U. 2015. Conjugated linoleic acid rich vegetable oil production from linoleic acid rich oils by heterogeneous catalysis. US Patent No. 9062272 B2
  92. Puniya AK, Chaitanya S, Tyagi AK, De S, Singh K. 2008. Conjugated linoleic acid producing potential of lactobacilli isolated from the rumen of cattle. J. Ind. Microbiol. Biotechnol. 35:1223–28 [Google Scholar]
  93. Raes K, Balcaen A, Dirinck P, De Winne A, Claeys E. et al. 2003. Meat quality, fatty acid composition and flavour analysis in Belgian retail beef. Meat Sci 65:1237–46 [Google Scholar]
  94. Raes K, Huyghebaert G, De Smet S, Nollet L, Arnouts S, Demeyer D. 2002. The deposition of conjugated linoleic acids in eggs of laying hens fed diets varying in fat level and fatty acid profile. J. Nutr. 132:182–89 [Google Scholar]
  95. Ramsay TG, Evock-Clover CM, Steele NC, Azain MJ. 2001. Dietary conjugated linoleic acid alters fatty acid composition of pig skeletal muscle and fat. J. Anim. Sci. 79:2152–61 [Google Scholar]
  96. Realini CE, Duckett SK, Brito GW, Dalla Rizza M, De Mattos D. 2004. Effect of pasture versus concentrate feeding with or without antioxidants on carcass characteristics, fatty acid composition, and quality of Uruguayan beef. Meat Sci 66:567–77 [Google Scholar]
  97. Reaney MJT. 2002. Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst. US Patent No. 6409649 B1
  98. Ritzenthaler KL, McGuire MK, Falen R, Shultz TD, Dasgupta N, McGuire MA. 2001. Estimation of conjugated linoleic acid intake by written dietary assessment methodologies underestimates actual intake evaluated by food duplicate methodology. J. Nutr. 131:1548–54 [Google Scholar]
  99. Rongione JC, Galante JH, Bernhardt RJ. 2010. Process for preparing conjugated linoleic acid and derivatives thereof from ricinoleic acid. US Patent No. 0036142 A1
  100. Rongione JC, Galante JH, Clauss SL, Bernhardt RJ, Xayariboun P. 2005. Production and purification of esters of conjugated linoleic acids. Patent No. WO067888
  101. Rosberg-Cody E, Ross RP, Hussey S, Ryan CA, Murphy BP. et al. 2004. Mining the microbiota of the neonatal gastrointestinal tract for conjugated linoleic acid–producing bifidobacteria. Appl. Environ. Microbiol. 70:4635–41 [Google Scholar]
  102. Ruan CM, Proctor A. 2014. Physicochemical properties of conjugated linoleic acid–rich soy oil. J. Am. Oil Chem. Soc. 91:49–54 [Google Scholar]
  103. Saebo A, Skarie C, Jerome D, Haroldsson D. 2002. Conjugated linoleic acid compositions and methods of making same. US Patent No. 6410761 B1
  104. Santos-Silva J, Bessa RJB, Mendes IA. 2003. The effect of supplementation with expanded sunflower seed on carcass and meat quality of lambs raised on pasture. Meat Sci 65:1301–8 [Google Scholar]
  105. Salamon RV, Vargane-Visi E, Andras CD, Kiss ZC, Csapo J. 2015. Synthetic methods to obtain conjugated fatty acids by catalysis: a review. Acta Aliment 44:229–34 [Google Scholar]
  106. Schoerken U, Meyer C, Horlacher P, Both S. 2007. Process for the enzymatic synthesis of triglycerides. US Patent No. 0148746 A1
  107. Seki K, Kaneko R, Kobayashi K. 1989. Photoconjugation of methyl linoleate in the presence of iodine as a sensitizer. J. Am. Oil Chem. Soc. 38:949–54 [Google Scholar]
  108. Shah U, Patel AR, Van de Walle D, Rajarethinem PS, Proctor A, Dewettinck K. 2014. CLA-rich soy oil margarine production and characterization. J. Am. Oil Chem. Soc. 91:309–16 [Google Scholar]
  109. Shang XG, Wang FL, Li DF, Yin JD, Li JY. 2004. Effects of dietary conjugated linoleic acid on the productivity of laying hens and egg quality during refrigerated storage. Poult. Sci. 83:1688–95 [Google Scholar]
  110. Shinn SE, Gilley AD, Proctor A, Anthony NB. 2015a. Three hen strains fed photoisomerized trans, trans CLA-rich soy oil exhibit different yolk accumulation rates and source-specific isomer deposition. Lipids 50:397–406 [Google Scholar]
  111. Shinn SE, Gilley AD, Proctor A, Anthony NB. 2015b. Effect of trans, trans CLA egg enrichment from CLA-rich soy oil on yolk fatty acid composition, viscosity and physical properties. J. Agric. Food Chem. 63:2506–13 [Google Scholar]
  112. Shinn SE, Proctor A, Gilley AD, Cho S, Martin E, Anthony NB. 2016. Effect of feeding CLA on plasma and granules fatty acid composition of eggs and prepared mayonnaise quality. Food Chem 197:57–65 [Google Scholar]
  113. Sieber R, Collomb M, Aeschlimann A, Eyer H. 2004. Impact of microbial cultures on conjugated linoleic acid in dairy products: a review. Int. Dairy J. 14:1–15 [Google Scholar]
  114. Sirri F, Tallarico N, Meluzzi A, Franchini A. 2003. Fatty acid composition and productive traits of broiler fed diets containing conjugated linoleic acid. Poult. Sci. 82:1356–61 [Google Scholar]
  115. Szymczyk B, Pisulewski PM, Szczurek W, Hanczakowski P. 2001. Effects of conjugated linoleic acid on growth performance, feed conversion efficiency, and subsequent carcass quality in broiler chickens. Br. J Nutr. 85:465–73 [Google Scholar]
  116. Sleeter RT. 1996. Method of conjugating double bonds in organic compounds. Patent No. EP0736593 A1
  117. Sleeter RT. 2004. Process for conjugating carbon-carbon double bonds in oils. US Patent No. 6696581 B1
  118. Song YS, Kang SW, Oh Dk, Rho YT, Hong SI. Kim SW. 2005. Bioconversion of linoleic acid to conjugated linoleic acid by. Bifidobacterium breve. Biotechnol. Bioprocess. Eng. 10:357–61 [Google Scholar]
  119. Sosa-Castañeda J, Hernández-Mendoza A, Astiazarán-García H, Garcia HS, Estrada-Montoya MC. et al. 2015. Screening of Lactobacillus strains for their ability to produce conjugated linoleic acid in milk and to adhere to the intestinal tract. J. Dairy Sci. 98:6651–59 [Google Scholar]
  120. Sutter F, Casutt MM, Ossowski DA, Scheeder MRL, Kreuzer M. 2000. Comparative evaluation of rumen‐protected fat, coconut oil and various oilseeds supplemented to fattening bulls: 1. Effects on growth, carcass and meat quality. Arch. Anim. Nutr. 53:1–23 [Google Scholar]
  121. Strzetelski J, Kowalczyk J, Osieglowski S, Stasiniewicz T, Lipiarska E, Pustkowiak H. 2001. Fattening bulls on maize silage and concentrate supplemented with vegetable oils. J. Anim. Feed Sci. 10:259–71 [Google Scholar]
  122. Szumacher-Strabel M, Cieslak A, Potkanski A, Kowalczyk J, Czauderna M. 2001. The effects of different amounts and types of fat on the level of conjugated linoleic acid level in the meat and milk of sheep. J. Anim. Feed Sci. 10:103–8 [Google Scholar]
  123. Szymczyk B, Pisulewski PM. 2003. Effects of dietary conjugated linoleic acid on fatty acid composition and cholesterol content of hen egg yolks. Br. J. Nutr. 90:93–99 [Google Scholar]
  124. Tang D, Marangoni AG. 2006. Microstructure and fractal analysis of fat crystal networks. J. Am. Oil Chem. Soc. 83:377–88 [Google Scholar]
  125. Timmermann F, Gaupp R, Gierke J, Von Kries R, Adams W, Sander A. 2001. Conjugated linoleic acid–based synthetic triglycerides. US Patent No. 6177580 B1
  126. US Dep. Health Hum. Serv., US Dep. Agric. 2015. 2015–2020 Dietary Guidelines for Americans Washington, DC: USDA, 8th ed. http://health.gov/dietaryguidelines/2015/guidelines/
  127. Van Nieuwenhove CP, Oliszewski R, Gonzalez SN, Chaia ABP. 2007. Conjugated linoleic acid conversion by dairy bacteria cultured in MRS broth and buffalo milk. Lett. Appl. Microbiol. 44:467–74 [Google Scholar]
  128. Villar-Tajadura MA, Rodriguez-Alcala LM, Martin V, de Segura AG, Rodriguez JM. et al. 2014. Production of conjugated linoleic and conjugated α-linolenic acid in a reconstituted skim milk–based medium by bifidobacterial strains isolated from human breast milk. Biomed. Res. Inter 23146133–41 [Google Scholar]
  129. Von Singer H, Seibel R, Mees U. 1977. Die Isomerisierung des Linolsäuremethylesters mit Rhodiumkomplexen. Fette. Seifen. Anstrichm. 79:147–50 [Google Scholar]
  130. Wang LM, Lv JP, Chu ZQ, Cui YY, Ren XH. 2007. Production of conjugated linoleic acid by Propionibacterium freudenreichii. Food Chem. 103:313–18 [Google Scholar]
  131. Ward AT, Wittenberg KM, Froebe HM, Przybylski R, Malcolmson L. 2003. Fresh forage and solin supplementation on conjugated linoleic acid levels in plasma and milk. J. Dairy Sci 86:1742–50 [Google Scholar]
  132. Whigham LD, Watras AC, Schoeller DA. 2007. Efficacy of conjugated linoleic acid for reducing fat mass: a meta-analysis in humans. Am. J. Clin. Nutr. 85:1203–11 [Google Scholar]
  133. Whitlock LA, Schingoethe DL, Hippen AR, Kalscheur KF, Baer RJ. et al. 2002. Fish oil and extruded soybeans fed in combination increased conjugated linoleic acids in milk of dairy cows more than when fed separately. J. Dairy Sci. 85:234–43 [Google Scholar]
  134. Xu S, Boylston TD, Glatz BA. 2004. Effect of lipid source on probiotic bacteria and conjugated linoleic acid formation in milk model systems. J. Am. Oil Chem. Soc. 81:589–95 [Google Scholar]
  135. Yamasaki M, Kitagawa T, Chujo H, Koyanaqi N, Nishida E. et al. 2004. Physiological difference between free and triglyceride-type conjugated linoleic acid on the immune function of C57BL/6N mice. J. Agric. Food Chem. 52:3644–48 [Google Scholar]
  136. Yan Y, Schmid U, Harris JB. 2005. Process for the production of CLA triglycerides. US Patent No. 6943261 B2
  137. Zeng Z, Lin J, Gong D. 2009. Identification of lactic acid bacterial strains with high conjugated linoleic acid–producing ability from natural sauerkraut fermentations. J. Food Sci. 74:M154–58 [Google Scholar]
/content/journals/10.1146/annurev-food-030216-025703
Loading
/content/journals/10.1146/annurev-food-030216-025703
Loading

Data & Media loading...

  • Article Type: Review Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error