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Commercial Conjugated Linoleic Acid (CLA) Fortified Dairy Products

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Handbook of Food Fortification and Health

Abstract

Conjugated linoleic acid (CLA) is a mixture of positional and geometric conjugated isomers of the essential linoleic fatty acid (LA, C18:2 cis 9, cis 12) characterized by the presence of double bonds from 6 to 14 position (6–8; 7–9; 8–10; 9–11; 10–12; 11–13; 12–14) and four conformations (cis, trans; trans, cis; trans, trans, and cis, cis) yielding 28 possible isomers [1]. The CLA is mainly found in food products from ruminants such as dairy products (0.34–1.07 g/100 g fat) [2] and beef (0.12–0.68 g/100 g fat) [3], because it is produced as an intermediate in the biohydrogenation pathway by ruminal bacteria (Fig. 14.1). The most abundant isomers (Table 14.1) are rumenic acid (RA; C18:2 cis 9, trans 11) accounting 75–90 % of total CLA in milk fat and C18:2 trans 7, cis 9 with 3–16 % [4]. Many research works had investigated the biological effects of RA reporting anticarcinogenic [10], antiaterogenic [11], antioxidative [12], and stimulation of the immune system [13]. Reduction of body fat [14] (antiobesity activity) has been associated with the C18:2 trans 10, cis 12 isomer mainly present in CLA synthetic oils. In the current market there are available rich CLA oils with a concentration of 80 g CLA/100 g oil with a 1:1 mixture of the two major isomers C18:2 cis 9, trans 11 and C18:2 trans 10, cis 12 and other minor isomers consisting of all cis/trans isomers of C18:2 9,11; 10,12 and 11,13 [15]. Various methods are available to produce synthetic CLA oil but alkaline isomerization of linoleic acid is the most common method [16] (Fig. 14.2).

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Abbreviations

BMI:

Body mass index

CLA:

Conjugated linoleic acid

CVD:

Cardiovascular diseases

EFSA:

European Food Safety Authority

GRAS:

Generally recognized as safe

LA:

Linoleic acid (C18:2 cis 9, cis 12)

MUFA:

Monounsaturated fatty acid

PUFA:

Polyunsaturated fatty acid

RA:

Rumenic acid (C18:2 cis 9, trans 11)

SFA:

Saturated fatty acid

TAG:

Triacylglycerol

TVA:

trans vaccenic acid (C18:1 trans 11)

References

  1. Roach JAG, Mossoba MM, Yurawecz MP, et al. Chromatographic separation and identification of conjugated linoleic acid isomers. Anal Chim Acta. 2002;465(1–2):207–26.

    Article  CAS  Google Scholar 

  2. Schmid A, Collomb M, Sieber R, et al. Conjugated linoleic acid in meat and meat products: a review. Meat Sci. 2006;73(1):29–41.

    Article  PubMed  CAS  Google Scholar 

  3. Fritsche J, Rickert R, Steinhart H, et al. Conjugated linoleic acid (CLA) isomers: formation, analysis, amounts in foods, and dietary intake. Fett Lipid. 1999;101(8):272–6.

    Article  CAS  Google Scholar 

  4. Collomb M, Schmid A, Sieber R, et al. Conjugated linoleic acids in milk fat: variation and physiological effects. Int Dairy J. 2006;16(11):1347–61.

    Article  CAS  Google Scholar 

  5. Chilliard Y, Glasser F, Ferlay A, et al. Diet, rumen biohydrogenation and nutritional quality of cow and goat milk fat. Eur J Lipid Sci Technol. 2007;109(8):828–55.

    Article  CAS  Google Scholar 

  6. Jenkins TC, McGuire MA. Major advances in nutrition: impact on milk composition. J Dairy Sci. 2006;89(4):1302–10.

    Article  PubMed  CAS  Google Scholar 

  7. Wallace RJ, McKain N, Shingfield KJ, et al. Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. J Lipid Res. 2007;48(10):2247–54.

    Article  PubMed  CAS  Google Scholar 

  8. Gómez-Cortés P. Efecto de la suplementación de la dieta ovina con distintas fuentes lipídicas sobre el perfil de ácidos grasos de la leche. E-prints Complutense: Facultad de Ciencias Químicas, Departamento de Química Física I, Universidad Complutense de Madrid; 2010.

    Google Scholar 

  9. Park YW, Juárez M, Ramos M, et al. Physico-chemical characteristics of goat and sheep milk. Small Rumin Res. 2007;68(1–2):88–113.

    Article  Google Scholar 

  10. Ha YL, Grimm NK, Pariza MW. Anticarcinogens from fried ground beef: heat-altered derivatives of linoleic acid. Carcinogenesis. 1987;8(12):1881–7.

    Article  PubMed  CAS  Google Scholar 

  11. Tanaka K. Occurrence of conjugated linoleic acid in ruminant products and its physiological functions. Anim Sci J. 2005;76(4):291–303.

    Article  CAS  Google Scholar 

  12. Hur SJ, Park GB, Joo ST. Biological activities of conjugated linoleic acid (CLA) and effects of CLA on animal products. Livest Sci. 2007;110(3):221–9.

    Article  Google Scholar 

  13. O’Shea M, Bassaganya-Riera J, Mohede ICM. Immunomodulatory properties of conjugated linoleic acid. Am J Clin Nutr. 2004;79(6):1199S–206.

    PubMed  Google Scholar 

  14. Park Y, Pariza MW. Mechanisms of body fat modulation by conjugated linoleic acid (CLA). Food Res Int. 2007;40(3):311–23.

    Article  CAS  Google Scholar 

  15. Rodriguez-Alcala LM, Fontecha J. Hot topic: fatty acid and conjugated linoleic acid (CLA) isomer composition of commercial CLA-fortified dairy products: evaluation after processing and storage. J Dairy Sci. 2007;90(5):2083–90.

    Article  PubMed  CAS  Google Scholar 

  16. Villeneuve P, Lago R, Barouh N, et al. Production of conjugated linoleic acid isomers by dehydration and isomerization of castor bean oil. J Am Oil Chem Soc. 2005;82(4):261–9.

    Article  CAS  Google Scholar 

  17. Ochoa JJ, Farquharson AJ, Grant I, et al. Conjugated linoleic acids (CLAs) decrease prostate cancer cell proliferation: different molecular mechanisms for cis-9, trans-11 and trans-10, cis-12 isomers. Carcinogenesis. 2004;25(7):1185–91.

    Article  PubMed  CAS  Google Scholar 

  18. de la Torre A, Debiton E, Juaneda P, et al. Beef conjugated linoleic acid isomers reduce human cancer cell growth even when associated with other beef fatty acids. Br J Nutr. 2006;95(2):346–52.

    Article  Google Scholar 

  19. Larsson SC, Bergkvist L, Wolk A. High-fat dairy food and conjugated linoleic acid intakes in relation to colorectal cancer incidence in the Swedish Mammography Cohort. Am J Clin Nutr. 2005;82(4):894–900.

    PubMed  CAS  Google Scholar 

  20. Chajés V, Lavillonniére F, Maillard V, et al. Conjugated linoleic acid content in breast adipose tissue of breast cancer patients and the risk of metastasis. Nutr Cancer. 2003;45(1):17–23.

    Article  PubMed  Google Scholar 

  21. Risérus U, Arner P, Brismar K, et al. Treatment with dietary trans10cis12 conjugated linoleic acid causes isomer-specific insulin resistance in obese men with the metabolic syndrome. Diabetes Care. 2002;25(9):1516–21.

    Article  PubMed  Google Scholar 

  22. Tricon S, Burdge GC, Jones EL, et al. Effects of dairy products naturally enriched with cis-9, trans-11 conjugated linoleic acid on the blood lipid profile in healthy middle-aged men. Am J Clin Nutr. 2006;83(4):744–53.

    PubMed  CAS  Google Scholar 

  23. Racine NM, Watras AC, Carrel AL, et al. Effect of conjugated linoleic acid on body fat accretion in overweight or obese children. Am J Clin Nutr. 2010;91(5):1157–64.

    Article  PubMed  CAS  Google Scholar 

  24. Belury MA, Kavanaugh CJ, Liu K-L. Conjugated linoleic acid modulates phorbol ester-induced PPAR-[delta] and K-FABP mRNA expression in mouse skin. Nutr Res. 2007;27(1):48–55.

    Article  CAS  Google Scholar 

  25. Tanmahasamut P, Liu J, Hendry LB, et al. Conjugated linoleic acid blocks estrogen signaling in human breast cancer cells. J Nutr. 2004;134(3):674–80.

    PubMed  CAS  Google Scholar 

  26. Coakley M, Johnson MC, McGrath E, et al. Intestinal bifidobacteria that produce trans-9, trans-11 conjugated linoleic acid: a fatty acid with antiproliferative activity against human colon SW480 and HT-29 cancer cells, vol. 56. Philadelphia, PA: ETATS-UNIS: Taylor & Francis; 2006.

    Google Scholar 

  27. Lai K-L, Torres-Duarte A, Vanderhoek J. 9-trans, 11-trans-CLA: antiproliferative and proapoptotic effects on bovine endothelial cells. Lipids. 2005;40(11):1107–16.

    Article  PubMed  CAS  Google Scholar 

  28. Benjamin S, Spener F. Conjugated linoleic acids as functional food: an insight into their health benefits. Nutr Metab (Lond). 2009;6:36.

    Article  Google Scholar 

  29. Ritzenthaler KL, McGuire MK, Falen R, et al. Stimation of conjugated linoleic acid intake by written dietary assessment methodologies underestimates actual intake evaluated by food duplicate methodology. J Nutr. 2001;131(5):1548–54.

    PubMed  CAS  Google Scholar 

  30. Ip C, Singh M, Thompson HJ, et al. Conjugated linoleic acid suppresses mammary carcinogenesis and proliferative activity of the mammary gland in the rat. Cancer Res. 1994;54(5):1212–5.

    PubMed  CAS  Google Scholar 

  31. Kamphuis MMJW, Lejeune MPGM, Saris WHM, et al. The effect of conjugated linoleic acid supplementation after weight loss on body weight regain, body composition, and resting metabolic rate in overweight subjects. Int J Obes Relat Metab Disord. 2003;27(7):840–7.

    Article  PubMed  CAS  Google Scholar 

  32. Larsen TM, Toubro S, Gudmundsen O, et al. Conjugated linoleic acid supplementation for 1 y does not prevent weight or body fat regain. Am J Clin Nutr. 2006;83(3):606–12.

    PubMed  CAS  Google Scholar 

  33. Gaullier J-M, Halse J, Hoye K, et al. Supplementation with conjugated linoleic acid for 24 months is well tolerated by and reduces body fat mass in healthy, overweight humans. J Nutr. 2005;135(4):778–84.

    PubMed  CAS  Google Scholar 

  34. Food and Drug Administration (FDA). GRASS notice for conjugates linoleic acid (CLA)-rich oil for use in certain foods. GRAS Notice No. GRN 000153. 2004.

    Google Scholar 

  35. EFSA Panel on Dietetic Products NaAN. Scientific opinion on the safety of “conjugated linoleic acid (CLA)-rich oil” (Tonalin® TG 80) as a novel food ingredient. EFSA J. 2010;8(5):1600.

    Google Scholar 

  36. Silveira MB, Carraro R, Monereo S, et al. Conjugated linoleic acid (CLA) and obesity. Public Health Nutr. 2007;10(10 A):1181–6.

    PubMed  Google Scholar 

  37. Tricon S, Burdge GC, Kew S, et al. Opposing effects of cis-9, trans-11 and trans-10, cis-12 conjugated linoleic acid on blood lipids in healthy humans. Am J Clin Nutr. 2004;80(3):614–20.

    PubMed  CAS  Google Scholar 

  38. Ramos R, Mascarenhas J, Duarte P, et al. Conjugated linoleic acid-induced toxic hepatitis: first case report. Dig Dis Sci. 2009;54(5):1141–3.

    Article  PubMed  Google Scholar 

  39. Palmquist DL, Lock AL, Shingfield KJ, et al. Biosynthesis of conjugated linoleic acid in ruminants and humans. In: Steve LT, editor. Advances in food and nutrition research, vol. 50. San Diego, California: Academic; 2005. p. 179–217.

    Chapter  Google Scholar 

  40. Mosley EE, McGuire MK, Williams JE, et al. Cis-9, trans-11 conjugated linoleic acid is synthesized from vaccenic acid in lactating women. J Nutr. 2006;136(9):2297–301.

    PubMed  CAS  Google Scholar 

  41. Morand-Fehr P, Fedele V, Decandia M, et al. Influence of farming and feeding systems on composition and quality of goat and sheep milk. Small Rumin Res. 2007;68(1–2):20–34.

    Article  Google Scholar 

  42. Collomb M, Sieber R, Buetikofer U. CLA isomers in milk fat from cows fed diets with high levels of unsaturated fatty acids. Lipids. 2004;39(4):355–64.

    Article  PubMed  CAS  Google Scholar 

  43. Dhiman TR, Satter LD, Pariza MW, et al. Conjugated linoleic acid (CLA) content of milk from cows offered diets rich in linoleic and linolenic acid. J Dairy Sci. 2000;83(5):1016–27.

    Article  PubMed  CAS  Google Scholar 

  44. Khanal RC. Factors affecting conjugated linoleic acid (CLA) content in milk, meat, and egg: a review. Pak J Nutr. 2004;3(2):82.

    Article  Google Scholar 

  45. Luna P, Fontecha J, Juarez M, et al. Conjugated linoleic acid in ewe milk fat. J Dairy Res. 2005;72(4):415–24.

    Article  PubMed  CAS  Google Scholar 

  46. Gómez-Cortés P, Frutos P, Mantecón AR, et al. Milk production, conjugated linoleic acid content, and in vitro ruminal fermentation in response to high levels of soybean oil in dairy ewe diet. J Dairy Sci. 2008;91(4):1560–9.

    Article  PubMed  Google Scholar 

  47. Chouinard PY, Corneau L, Butler WR, et al. Effect of dietary lipid source on conjugated linoleic acid concentrations in milk fat. J Dairy Sci. 2001;84(3):680–90.

    Article  PubMed  CAS  Google Scholar 

  48. Anadón A, Martínez-Larrañaga MR, Martínez MA, et al. Acute oral safety study of dairy fat rich in trans-10 C18:1 versus vaccenic plus conjugated linoleic acid in rats. Food Chem Toxicol. 2010;48(2):591–8.

    Article  PubMed  Google Scholar 

  49. Gómez-Cortés P, Bach A, Luna P, et al. Effects of extruded linseed supplementation on n-3 fatty acids and conjugated linoleic acid in milk and cheese from ewes. J Dairy Sci. 2009;92(9):4122–34.

    Article  PubMed  Google Scholar 

  50. Fuentes MC, Calsamiglia S, Sanchez C, et al. Effect of extruded linseed on productive and reproductive performance of lactating dairy cows. Livest Sci. 2008;113(2–3):144–54.

    Article  Google Scholar 

  51. Bauman DE, Mather IH, Wall RJ, et al. Major advances associated with the biosynthesis of milk. J Dairy Sci. 2006;89(4):1235–43.

    Article  PubMed  CAS  Google Scholar 

  52. Smit LA, Baylin A, Campos H. Conjugated linoleic acid in adipose tissue and risk of myocardial infarction. Am J Clin Nutr. 2010;92(1):34–40.

    Article  PubMed  CAS  Google Scholar 

  53. Warensjö E, Jansson JH, Cederholm T, et al. Biomarkers of milk fat and the risk of myocardial infarction in men and women: a prospective, matched case-control study. Am J Clin Nutr. 2010;92(1):194–202.

    Article  PubMed  Google Scholar 

  54. Bauman DE, Griinari JM. Nutritional regulation of milk fat synthesis. Annu Rev Nutr. 2003;23:203–27.

    Article  PubMed  CAS  Google Scholar 

  55. Howard FAC, Henderson C. Hydrogenation of polyunsaturated fatty acids by human colonic bacteria. Lett Appl Microbiol. 1999;29(3):193–6.

    Article  PubMed  CAS  Google Scholar 

  56. Jiang J, Björck L, Fondén R. Production of conjugated linoleic acid by dairy starter cultures. J Appl Microbiol. 1998;85(1):95–102.

    Article  PubMed  CAS  Google Scholar 

  57. Kishino S, Park S-B, Takeuchi M, et al. Novel multi-component enzyme machinery in lactic acid bacteria catalyzing CC double bond migration useful for conjugated fatty acid synthesis. Biochem Biophys Res Commun. 2011;416(1–2):188–93.

    Article  PubMed  CAS  Google Scholar 

  58. Liavonchanka A, Hornung E, Feussner I, et al. Structure and mechanism of the Propionibacterium acnes polyunsaturated fatty acid isomerase. Proc Natl Acad Sci U S A. 2006;103(8):2576–81.

    Article  PubMed  CAS  Google Scholar 

  59. Van Nieuwenhove CP, Oliszewski R, Gonzalez SN, et al. Influence of bacteria used as adjunct culture and sunflower oil addition on conjugated linoleic acid content in buffalo cheese. Food Res Int. 2007;40(5):559–64.

    Article  Google Scholar 

  60. Alonso L, Cuesta EP, Gilliland SE. Production of free conjugated linoleic acid by Lactobacillus acidophilus and Lactobacillus casei of human intestinal origin. J Dairy Sci. 2003;86(6):1941–6.

    Article  PubMed  CAS  Google Scholar 

  61. Adamczak M, Bornscheuer UT, Bednarski W. Properties and biotechnological methods to produce lipids containing conjugated linoleic acid. Eur J Lipid Sci Technol. 2008;110(6):491–504.

    Article  CAS  Google Scholar 

  62. Puniya AK, Chaitanya S, Tyagi AK, et al. Conjugated linoleic acid producing potential of lactobacilli isolated from the rumen of cattle. J Ind Microbiol Biotechnol. 2008;35(11):1223–8.

    Article  PubMed  CAS  Google Scholar 

  63. Akalin AS, Tokusoglu O, Gonc S, et al. Occurrence of conjugated linoleic acid in probiotic yoghurts supplemented with fructooligosaccharide. Int Dairy J. 2007;17(9):1089–95.

    Article  CAS  Google Scholar 

  64. Rodríguez-Alcalá LM, Braga T, Malcata FX, et al. Quantitative and qualitative determination of CLA produced by Bifidobacterium and lactic acid bacteria by combining spectrophotometric and Ag+-HPLC techniques. Food Chem. 2011;125:1373–8.

    Article  Google Scholar 

  65. Gorissen L, Raes K, Weckx S, et al. Production of conjugated linoleic acid and conjugated linolenic acid isomers by Bifidobacterium species. Appl Microbiol Biotechnol. 2010;87(6):2257–66.

    Article  PubMed  CAS  Google Scholar 

  66. Wall R, Ross RP, Shanahan F, et al. Metabolic activity of the enteric microbiota influences the fatty acid composition of murine and porcine liver and adipose tissues. Am J Clin Nutr. 2009;89(5):1393–401.

    Article  PubMed  CAS  Google Scholar 

  67. Rosberg-Cody E, Stanton C, O’Mahony L, et al. Recombinant lactobacilli expressing linoleic acid isomerase can modulate the fatty acid composition of host adipose tissue in mice. Microbiology. 2011;157(2):609–15.

    Article  PubMed  CAS  Google Scholar 

  68. Park HG, Heo W, Kim SB, et al. Production of conjugated linoleic acid (CLA) by Bifidobacterium breve LMC520 and its compatibility with CLA-producing rumen bacteria. J Agric Food Chem. 2010;59(3):984–8.

    Article  PubMed  Google Scholar 

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Rodríguez-Alcalá, L.M., Villar-Tajadura, A., Juarez, M., Fontecha, J. (2013). Commercial Conjugated Linoleic Acid (CLA) Fortified Dairy Products. In: Preedy, V., Srirajaskanthan, R., Patel, V. (eds) Handbook of Food Fortification and Health. Nutrition and Health. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4614-7076-2_14

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