Distribution and Content of Geometric Isomers of Conjugated Linoleic Acid in Dairy Foods from the Quebec Province of Canada

  • Park, Seung-Yong (Department of Animal Science, Cheonan Yonam College) ;
  • Ahn, Jae-Eun (Department of Food Science and Agricultural Chemistry, McGill University) ;
  • Kim, Geun-Bae (Department of Animal Science and Technology, Chung-Ang University) ;
  • Jung, Mun-Yhung (Department of Food Science and Technology, Woosuk University) ;
  • Lee, Byong-H. (Food R&D Centre, Agriculture and Agri-Food Canada)
  • Published : 2008.02.29

Abstract

The distributions and content of geometrical isomers of conjugated linoleic acids (CLA) in dairy foods such as milk, yogurt, and cheese, produced or being sold in the Quebec province of Canada, were investigated by gas chromatographic analysis. The mean contents of total CLA (mg/g fat) were $5.06{\pm}0.74$ in 4 low-fat milk samples, $14.14{\pm}4.95$ in 6 yogurt samples, and $18.22{\pm}7.89$ in 5 natural ripened cheeses. Among the yogurt samples, YY contained the highest content of total CLA ($20.68{\pm}5.17\;mg/g$ fat). Among the cheese samples, Gruyere contained the highest amount of total CLA ($29.86{\pm}0.62$) as well as c-9,t-11 ($22.03{\pm}0.36\;mg/g$ fat), followed by Jarlsberg ($22.76{\pm}0.14$), Provolone ($16.42{\pm}0.52$), Cheddar ($13.83{\pm}0.81$), and Swiss ($8.23{\pm}1.11$). Based on the distribution ratios of CLA isomers in these dairy foods, the c-9,t-11 isomer appeared to be the major CLA isomer in both the low-fat milk ($89.87{\pm}2.39%$) and yogurt ($90.98{\pm}4.42%$). In the cheeses, however, the ratio of c-9,t-11 ($54.86{\pm}13.06%$) was slightly higher than that of c-10,c-12 ($40.81{\pm}13.40%$).

Keywords

References

  1. Ha YL, Grimm NK, Pariza MW. Newly recognized anticarcinogenic fatty acid: Identification and quantification in natural and processed cheese. J. Agr. Food Chem. 37: 75-81 (1989) https://doi.org/10.1021/jf00085a018
  2. Delany JP, Blohm F, Truett AA, Scimeca JA, West DB. Conjugated linoleic acid rapidly reduce body fat content in mice without affecting energy intake. Am. J. Phys. 276: 1172-1179 (1999)
  3. Baumgard LH, Corl BA, Dwyer DA, Saebo A, Bauman DE. Identification of the conjugated linoleic acid isomer that inhibits milk fat synthesis. Am. J. Phys. 278: 179-184 (2000)
  4. Martin JC, Sebedio JL, Caselli C, Pimont C, Martine L, Beruard A. Lymphatic delivery and in vitro pancreatic lipase hydrolysis of glycerol esters of conjugated linoleic acid in rat. J. Nutr. 130: 1108- 1114 (2000)
  5. Miner JL, Cederberg CA, Nielson MK, Chen X, Baile CA. Conjugated linoleic acid (CLA), body fat, and apoptosis. Obes. Res. 9: 129-134 (2001) https://doi.org/10.1038/oby.2001.16
  6. Park YJ, Albright J, Storkson JM, Cook ME, Pariza MW. Effects of conjugated linoleic acid on body composition in mice. Lipids 32: 853-858 (1997) https://doi.org/10.1007/s11745-997-0109-x
  7. Delany JP, West DB. Changes in body composition with conjugated linoleic acid. J. Am. Coll. Nutr. 19: 487-493 (2000) https://doi.org/10.1080/07315724.2000.10718952
  8. Mueller HL, Kirchgessner M, Roth FX, Stangle GI. Effects of conjugated linoleic acid on energy metabolism in growing finishing pigs. J. Anim. Physiol. An. N. 83: 85-94 (2000) https://doi.org/10.1046/j.1439-0396.2000.00253.x
  9. Chin SF, Liu W, Storkson JM, Ha YL, Pariza MW. Dietary sources of conjugated dienoic isomers of linoleic acid, a newly recognized class anticarcinogens. J. Food Compos. Anal. 5: 185-197 (1992) https://doi.org/10.1016/0889-1575(92)90037-K
  10. Riera JB, Hontecillas R, Beitz DC. Colonic anti inflammatory mechanism of conjugated linoleic acid. Clin. Nutr. 21: 451-459 (2002) https://doi.org/10.1054/clnu.2002.0594
  11. Nicolosi RT, Rogers EJ, Kirtchersyky D, Scimeca JA, Huth PJ. Dietary conjugated linoleic acid reduces plasma lipoproteins and early aortic atherosclerosis in hypercholesterolemic hamsters. Artery 22: 266-277 (1997)
  12. Stangle GI. High dietary levels of a conjugated linoleic acid mixture alter hepatic glycerophospholipid class profile and cholesterol carrying serum lipoprotein of rats. J. Nutr. Biochem. 11: 184-191 (2000) https://doi.org/10.1016/S0955-2863(00)00063-2
  13. Miller CC, Park Y, Pariza MW, Cook ME. Feeding conjugated linoleic acid to animals partially overcomes catabolic responses due to endotoxin injection. Biochem. Bioph. Res. Co. 198: 1107-1112 (1994) https://doi.org/10.1006/bbrc.1994.1157
  14. Liu KL, Belury MA. Conjugated linoleic acid residues arachidonic acid content and ${PGE_2}$ synthesis in murine keratinocytes. Cancer Lett. 127: 15-22 (1998) https://doi.org/10.1016/S0304-3835(97)00479-5
  15. Pariza MW, Park YJ, Cook ME. Conjugated linoleic acid and the control of cancer and obesity. Toxicol. Sci. 52: 107-110 (1999) https://doi.org/10.1093/toxsci/52.suppl_1.107
  16. Ma DWL, Wierzbicki AA, Field CJ, Clandinin MT. Preparation of conjugated linoleic acid from safflower oil. J. Am. Oil Chem. Soc. 76: 729-730 (1999) https://doi.org/10.1007/s11746-999-0167-3
  17. Pariza MW, Park YJ, Cook ME. The biologically acitive isomers of conjugated linoleic acid. Prog. Lipid Res. 40: 283-287 (2001) https://doi.org/10.1016/S0163-7827(01)00008-X
  18. Jiang J, Bjorck L, Fonden R. Production of conjugated linoleic acid by dairy starter cultures. J. Appl. Microbiol. 85: 95-102 (1998) https://doi.org/10.1046/j.1365-2672.1998.00481.x
  19. Griinari JM, Cort BA, Lacy SH, Chouinard PY, Nurmela KVV, Bauman DE. Conjugated linoleic acid is synthesized endogenously in lactating dairy cows by ${\Delta}^{9}$-desaturase. J. Nutr. 130: 2285-2291 (2000)
  20. Ogawa J, Matsumurs K, Kishino S, Omura Y, Shimizu S. Conjugated linoleic acid accumulation via 10-hydroxy-12-octadecanoic acid during microaerobic transformation of linoleic acid by Lactobacillus acidophilus. Appl. Environ. Microb. 67: 1246-1252 (2001) https://doi.org/10.1128/AEM.67.3.1246-1252.2001
  21. Kelly ML, Berrym JR, Ewyer DA, Griinari JM, Choinard PY, Vanamburgh ME, Bauman DE. Dietary fatty acid sources affect conjugated linoleic acid concentrations in milk from lactating dairy cow. J. Nutr. 128: 881-885 (1998)
  22. Bessa RJ, Santos-Silva J, Ribeiro JM, Portugal AV. Reticulo-rumen bio-hydrogenation and the enrichment of ruminal edible products with linoleic acid conjugated isomers. Appl. Environ. Microb. 63: 201-211 (2000)
  23. Choi SH, Song MK. Effects of the level of carbohydrates on biohydrogenation and CLA production by rumen bacteria when incubated with soybean oil and flaxseed oil in vitro. J. Anim. Sci. Technol. 48: 521-532 (2005)
  24. Jiang J, Bjorck L, Fonden R, Emanuelson M. Occurence of conjugated 9,11-octadecadienoic acid (CLA) in bovine milk: Effects of feed and feeding regimen. J. Dairy Sci. 79: 438-445 (1996) https://doi.org/10.3168/jds.S0022-0302(96)76383-X
  25. Wang JH, Song MK. pH affects the in vitro formation of cis-9,trans- 11 octadecanoic acid by ruminal bacteria when incubated with oilseeds. Asian-Austral. J. Anim. 16: 1743-1748 (2003) https://doi.org/10.5713/ajas.2003.1743
  26. Choi SH, Song MK. Effects of C18-polyunsaturated fatty acids on their direct incorporation into the rumen bacterial lipids and CLA production in vitro. Asian-Austral. J. Anim. 18: 512-515 (2006)
  27. Dhiman TR, Helmin ED, Mcmahon DJ, Fire RL, Pariza MW. Conjugated linoleic acid content in milk and cheese from cows fed extruded oilseeds. J. Dairy Sci. 82: 412-419 (1999) https://doi.org/10.3168/jds.S0022-0302(99)75247-1
  28. Choi NJ, Imm JY, Oh SJ, Kim BC, Hwang HJ, Kim YJ. Effect of pH and oxygen on conjugated linoleic acid (CLA) production by mixed rumen bacteria from cows fed high concentrate and high forage diets. Anim. Feed Sci. Tech. 123-124: 643-653 (2005) https://doi.org/10.1016/j.anifeedsci.2005.04.054
  29. Lin H, Boylston TD, Chang MJ, Luedecke LD, Shultz TD. Survey of the conjugated linoleic acid contents of dairy products. J. Dairy Sci. 78: 2358-2364 (1995) https://doi.org/10.3168/jds.S0022-0302(95)76863-1
  30. Ha YL, Pariza MW. Naturally occuring novel anticarcinogens: Conjugated dienoic derivatives of linoleic acid (CLA). J. Korean Soc. Food Nutr. 24: 401-407 (1991)
  31. Chin SF, Storkson JM, Lui M, Albright KJ, Pariza MW. Conjugated linoleic acid (9,11- and 10,12-octadecadienoic acid) is produced on conventional but not germ-free rats fed linoleic acid. J. Nutr. 124: 694-701 (1994)
  32. Yun CS. Screening of dairy starter culture for CLA producing and development of functional fermented milk by the starter culture. Research Report No. 501026-2. Agriculture R&D Promotion Center, Seoul, Korea (2003)
  33. Pariza MW. Method of producing conjugated fatty acids. U.S. patent 6,060,304 (2000)
  34. Jung MY, Kim GB, Jang ES, Jung YK, Park SY, Lee BH. Improved extraction method with hexane for gas chromatographic analysis of conjugated linoleic acids. J. Dairy Sci. 89: 90-94 (2006) https://doi.org/10.3168/jds.S0022-0302(06)72072-0
  35. Jung MY, Ha YL. Conjugated linoleic acid isomers in partially hydrogenated soybean oil obtained during nonselective and selective hydrogenation processes. J. Agr. Food Chem. 47; 704-708 (1999) https://doi.org/10.1021/jf981087z
  36. Shantha NC, Decker EA, Henning B. Comparison of methylation methods for the quantification of conjugated linoleic acid isomer. J. Assoc. Off. Ana. Chem. Int. 73: 644-649 (1993)
  37. Collomb M, Butikofer U, Sieber R, Bosset JO, Jeangros B. Conjugated linoleic acid and trans fatty acid composition of cows' milk fat produced in lowland and highland. J. Dairy Res. 68: 519-523 (2001)
  38. Zlatanos S, Laskaridis K, Feist C, Sagredos A. CLA content and fatty acid composition of Greek Feta cheese and hard cheese. Food Chem. 78: 471-477 (2002) https://doi.org/10.1016/S0308-8146(02)00159-0
  39. Lin H, Boylston TD, Luedecke LO, Shultz TD. Factors affecting the conjugated linoleic acid content of Cheddar cheese. J. Agr. Food Chem. 46: 801-807 (1998) https://doi.org/10.1021/jf970639v
  40. Jiang J, Björck L, Fondén R. Conjugated linoleic acid in swedish dairy products with special reference to the manufacture of hard cheeses. Int. Dairy J. 7: 863-867 (1997) https://doi.org/10.1016/S0958-6946(98)00004-1
  41. Werner SA, Luedecke LO, Schultz TD. Determination of conjugated linoleic acid content and isomer distribution in three Cheddar-type cheese: Effects of cheese cultures, processing, and aging. J. Agr. Food Chem. 41: 1817-1821 (1992)
  42. Steffen C, Eberhard P, Bosset JO, Ruegg M. Swiss-type varieties. pp. 83-110. In: Cheese Chemistry. Fox PF (ed). Chapman & Hall, London, UK (1993)
  43. Robinson RK. A Colour Guide to Cheese and Fermented Milks. Chapman & Hall, London, UK. pp. 103-104 (1995)