Conjugated linolenic acid (CLnA) isomers as new bioactive lipid compounds in ruminant-derived Food products. A review

Journal of Animal and Feed Sciences

Volumn 26, Issue 1, 2017, Pages 3-17

  Bialek M ^a   Czauderna, M ^a   Bialek A ^b  

^a KIELANOWSKI INSTITUTE OF ANIMAL PHYSIOLOGY AND NUTRITION   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Biohydrogenation; Conjugated linolenic acid; Food of ruminant origin; Ruminants; Unsaturated fatty acids

Indexed keywords

EID: 85020003768     PISSN: 12301388     EISSN: None     Source Type: Journal    
DOI: 10.22358/jafs/68862/2017     Document Type: Article

References (89)

1. Akraim F., Nicot M. C., Juaneda P., Enjalbert F., 2007. Conjugated linolenic acid (CLnA), conjugated linoleic acid (CLA) and other biohydrogenation intermediates in plasma and milk fat of cows fed raw or extruded linseed. Animal 1, 835-843, https://doi.org/10.1017/S175173110700002X
2. Alves S. P., Bessa R. J. B., 2014. The trans-10, cis-15 18:2: a missing intermediate of trans-10 shifted rumen biohydrogenation pathway? Lipids 49, 527-541, https://doi.org/10.1007/s11745-014-3897-4
3. th Edition. Gaithersburg, MD (USA)
4. Badinga L., Gülay M. S., Ealy A., 2016. CLA and EPA inhibit LPS-induced prostaglandin release from bovine endometrial cells through an NF-?B-dependent signaling mechanism. Turk. J. Vet. Anim. Sci. 40, 382-388, https://doi.org/10.3906/vet-1510-67
5. Bessa R. J. B., Alves S. P., Jerónimo E., Alfaia C. M., Prates J. A. M., Santos-Silva J., 2007. Effect of lipid supplements on ruminal biohydrogenation intermediates and muscle fatty acids in lambs. Eur. J. Lipid Sci. Technol. 109, 868-878, https://doi.org/10.1002/ejlt.200600311
6. Bialek A., Jelinska M., Bamburowicz-Klimkowska M., Tokarz A., 2014b. Effect of bitter melon aqueous extract and pomegranate oil on glucose concentration and lipid profile in blood of rats - preliminary study. Int. J. Cardiol. Lipidol. Res. 1, 1-7, https://doi.org/10.15379/2410-2822.2014.01.01.01
7. Białek A., Jelińska M., Tokarz A., Pergół A., Pinkiewicz K., 2016. Influence of pomegranate seed oil and bitter melon aqueous extract on polyunsaturated fatty acids and their lipoxygenase metabolites concentration in serum of rats. Prostaglandins Other Lipid Mediat. 126, 29-37, https://doi.org/10.1016/j.prostaglandins.2016.07.005
8. Białek A., Teryks M., Tokarz A., t2014a. Conjugated linolenic acids (CLnA, super CLA) - natural sources and biological activity (in Polish). Postȩpy Hig. Med. Dosw. 68, 1238-1250, https://doi.org/10.5604/17322693.1127881
9. Białek A., Tokarz A., 2013. Conjugated linoleic acid as a potential protective factor in prevention of breast cancer (in Polish). Postȩpy Hig. Med. Dosw. 67, 6-14, https://doi.org/10.5604/17322693.1028764
10. Buccioni A., Decandia M., Minieri S., Molle G., Cabiddu A., 2012. Lipid metabolism in the rumen: New insights on lipolysis and biohydrogenation with an emphasis on the role of endogenous plant factors. Anim. Feed Sci. Technol. 74, 1-25, https://doi.org/10.1016/j.anifeedsci.2012.02.009
11. Chaturvedula V. S. P., Indra P., 2011. Bioactive chemical constituents from pomegranate (Punica granatum) juice, seed and peel - a review. Int. J. Res. Chem. Environ. 1, 1-18
12. Corl B. A., Baumgard L. H., Dwyer D. A., Griinari J. M., Phillips B. S., Bauman D. E., 2001. The role of Δ9-desaturase in the production of cis-9, trans-11 CLA. J. Nutr. Biochem. 12, 622-630, http://dx.doi.org/10.1016/S0955-2863 (01) 00180-2
13. +-hPLC of conjugated linoleic acids on a silica-based stationary phase. Part III: Model compounds. J. Sep. Sci. 25, 897-903, https://doi.org/10.1002/1615-9314 (20020301) 25:4<245::AID-JSSC245>3.0. CO;2-G
14. Czauderna M., Kowalczyk J., Marounek M., Michalski J. P., Rozbicka-Wieczorek A. J., Krajewska K. A., 2011. A new internal standard for HPLC assay of conjugated linoleic acid in animal tissues and milk. Czech J. Anim. Sci. 56, 23-29
15. Czauderna M., Kowalczyk J., Wąsowska I., Niedźwiecka K. M., 2003. Determination of conjugated linoleic acid isomers by liquid chromatography and photodiode array detection. J. Anim. Feed Sci. 12, 369-382, https://doi.org/10.22358/jafs/67717/2003
16. de Carvalho E. B. T., de Melo I. L. P., Mancini-Filho J., 2010. Chemical and physiological aspects of isomers of conjugated fatty acids. Ciênc. Tecnol. Aliment. 30, 295-307, https://doi.org/10.1590/S0101-20612010000200002
17. Decker E. A., Park Y., 2010. Healthier meat products as functional foods. Meat Sci. 86, 49-55, https://doi.org/10.1016/j. meatsci.2010.04.021
18. de la Fuente M. A., Luna P., Juárez M., 2006. Chromatographic techniques to determine conjugated linoleic acid isomers. TrAC Trends Anal. Chem. 25, 917-926, https://doi.org/10.1016/j. trac.2006.04.012
19. Destaillats F., Berdeaux O., Sébédio J.-L., Juaneda P., Grégoire S., Chardigny J.-M., Bretillon L., Angers P., 2005a. Metabolites of conjugated isomers of α-linolenic acid (CLnA) in the rat.. J. Agric. Food Chem. 53, 1422-1427, https://doi.org/10.1021/jf0481958
20. Destaillats F., Trottier J. P., Galvez J. M. G., Angers P., 2005b. Analysis of α-linolenic acid biohydrogenation intermediates in milk fat with emphasis on conjugated linolenic acids. J. Dairy Sci. 88, 3231-3239, https://doi.org/10.3168/jds. S0022-0302 (05) 73006-X
21. Doreau M., Bauchart D., Chilliard Y., 2011. Enhancing fatty acid composition of milk and meat through animal feeding. Anim. Prod. Sci. 51, 19-29, https://doi.org/10.1071/AN10043
22. Dugan M. E. R., Aldai N., Aalhaus J. L., Rolland D. C., Kramer J. K. G., 2011. Review: Trans-forming beef to provide healthier fatty acid profiles. Can. J. Anim. Sci. 91, 545-556, https://doi.org/10.4141/cjas2011-044
23. Ebrahimi M., Rajion M. A., Goh Y. M., 2014. Effects of oils rich in linolenic and α-linolenic acids on fatty acid profile and gene expression in goat meat. Nutrients 6, 3913-3928, https://doi.org/10.3390/nu6093913
24. Fontes A. L. R., 2015. Identification of bacterial strains able to produce CLNA isomers for a possible application in the elaboration of new functional food products. Master Thesis, Universidade Católica Portugesa, Porto (Portugal)
25. Fritsche J., Fritsche S., Solomon M. B., Mossoba M. M., Yurawecz M. P., Morehouse K., Ku Y., 2000. Quantitative determination of conjugated linoleic acid isomers in beef fat. Eur. J. Lipid Sci. Technol. 102, 667-672, https://doi.org/10.1002/1438-9312 (200011) 102:11<667::AID-EJLT667>3.0. CO;2-N
26. Gasmi J., Sanderson J. T., 2013. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study. Phytomedicine 20, 734-742, https://doi.org/10.1016/j. phymed.2013.01.012
27. Glasser F., Ferlay A., Doreau M., Schmidely P., Sauvant D., Chilliard Y., 2008. Long-chain fatty acid metabolism in dairy cows: a metaanalysis of milk fatty acid yield in relation to duodenal fows and de novo synthesis. J. Dairy Sci. 91, 2771-2785, https://doi.org/10.3168/jds.2007-0383
28. Gómez-Cortés P., Tyburczy C., Brenna J. T., Juárez M., de la Fuente M. A., 2009. Characterization of cis-9 trans-11 trans-15 C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS. J. Lipid Res. 50, 2412-2420, https://doi.org/10.1194/jlr. M800662-JLR200
29. Griinari J. M., Bauman D. E., 1999. Biosynthesis of conjugated linoleic acid and its incorporation into meat and milk in ruminants. In: M. P. Yurawecz, Mossoba M. M., J. K. G. Kramer, M. W. Pariza, G. J. Nelson (Editors). Advances in Conjugated Linoleic Acid Research. Volume 1. AOCS Press, Champaign, IL (USA), pp. 180-200
30. Grossmann M. E., Mizuno N. K., Schuster T., Cleary M. P., 2010. Punicic acid is an ω-5 fatty acid capable of inhibiting breast cancer proliferation. Int. J. Oncol. 36, 421-426, https://doi.org/10.3892/ijo-00000515
31. Ha Y. L., Grimm N. K., Pariza M. W., 1987. Anticarcinogens from fried ground beef: heat-altered derivatives of linoleic acid. Carcinogenesis 8, 1881-1887, https://doi.org/10.1093/carcin/8.12.1881
32. Halmemies-Beauchet-Filleau A., Kokkonen T., Lampi A.-M., Toivonen V., Shingfield K. J., Vanhatalo A., 2011. Effect of plant oils and camelina expeller on milk fatty acid composition in lactating cows fed diet based on red clover silage. J. Dairy Sci. 94, 4413-4430, https://doi.org/10.3168/jds.2010-3885
33. Harfoot C. G., Hazlewood G. P., 1997. Lipid metabolism in the rumen. In: P. N. Hobson, C. S. Stewart (Editors). The Rumen Microbial Ecosystem. Chapman & Hall, London (UK), pp. 382-426
34. Hennessy A. A., Ross R. P., Devery R., Stanton C., 2011. The health promoting properties of the conjugated isomers of α-linolenic acid. Lipids 46, 105-119, https://doi.org/10.1007/s11745-010-3501-5
35. Honkanen A. M., Leskinen H., Toivonen V., McKain N., Wallace R. J., Shingfield K. J., 2016. Metabolism of α-linolenic acid during incubations with strained bovine rumen contents: products and mechanisms. Br. J. Nutr. 115, 2093-2105, https://doi.org/10.1017/S0007114516001446
36. Jelińska M., Białek A., Mojska H., Gielecińska I., Tokarz A., 2014. Effect of conjugated linoleic acid mixture supplemented daily after carcinogen application on linoleic and arachidonic acid metabolites in rat serum and induced tumours. Biochim. Biophys. Acta Mol. Basis Dis. 1842, 2230-2236, https://doi.org/10.1016/j.bbadis.2014.08.013
37. Jenkins T. C., Wallace R. J., Moate P. J., Mosley E. E., 2008. Recent advances in biohydrogenation of unsaturated fatty acids within the rumen microbial ecosystem. J. Anim. Sci. 86, 397-412, https://doi.org/10.2527/jas.2007-0588
38. Jerónimo E., Alves S. P., Alfaia C. M., Prates J. M., Santos-Silva J., Bessa R. J. B., 2011. Biohydrogenation intermediates are differentially deposited between polar and neutral intramuscular lipids of lambs. Eur. J. Lipid Sci. Technol. 113, 924-934, https://doi.org/10.1002/ejlt.201000398
39. Kairenius P., Toivonen T., Shingfeld K. J., 2011. Identification and ruminal outflow of long-chain fatty acids biohydrogenation intermediates in cows fed diets containing fish oil. Lipids 46, 587-606, https://doi.org/10.1007/s11745-011-3561-1
40. Kishino S., Ogawa J., Yokozeki K., Shimizu S., 2009. Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production. Appl. Microbiol. Biotechnol. 84, 87-97, https://doi.org/10.1007/s00253-009-1949-0
41. Koba K., Belury M. A. Sugano M., 2007a. Potential health benefits of conjugated trienoic acids. Lipid Technol. 19, 200-203, https://doi.org/10.1002/lite.200700067
42. Koba K., Imamura J., Akashoshi A., Kohno-Murase J., Nishizono S., Iwabuchi M., Tanaka K., Sugano M., 2007b. Genetically modified rapeseed oil containing cis-9, trans-11, cis-13-octadecatrienoic acid affects body fat mass and lipid metabolism in mice. J. Agric. Food Chem. 55, 3741-3748, https://doi.org/10.1021/jf063264z
43. Kotsampasi B., Christodoulou V., Zotos A., Liakopoulou-Kyriakides M., Goulas P., Petrotos K., Natas P., Bampidis V. A., 2014. Effects of dietary pomegranate byproducts silage supplementation on performance, carcass characteristics and meat quality of growing lambs. Anim. Feed Sci. Technol. 197, 92-102, https://doi.org/10.1016/j.anifeedsci.2014.09.003
44. Leat W. M. F., Kemp P., Lysons R. J., Alexander T. J. L., 1977. Fatty acid composition of depot fats from gnotobiotic lambs. J. Agric. Sci. 88, 175-179, https://doi.org/10.1017/S0021859600033918
45. Lee Y.-J., Jenkins T. C., 2011. Biohydrogenation of linolenic acid to stearic acid by the rumen microbial population yields multiple intermediate conjugated diene isomers. J. Nutr. 141, 1445-1450, https://doi.org/10.3945/jn. 111.138396
46. Lerch S., Shingfield K. J., Ferlay A., Vanhatalo A., Chillard Y., 2012. Rapeseed or linseed in grass-based diets: Effects on conjugated linoleic and conjugated linolenic acid isomers in milk fat from Holstein cows over 2 consecutive lactations. J. Dairy Sci. 95, 7269-7287, https://doi.org/10.3168/jds.2012-5654
47. Loor J. J., Ueda K., Ferlay A., Chilliard Y., Doreau M., 2004. Biohydrogenation, duodenal flow, and intestinal digestibility of trans fatty acid and conjugated linoleic acids in response to dietary forage: concentrate ratio and linseed oil in dairy cows. J. Dairy Sci. 87, 2472-2485, https://doi.org/10.3168/jds. S0022-0302 (04) 73372-X
48. Loor J. J., Ueda K., Ferlay A., Chilliard Y., Doreau M., 2005. Intestinal flow and digestibility of trans fatty acids and conjugated linoleic acids (CLA) in dairy cows fed a high-concentrate diet supplemented with fish oil, linseed oil, or sunflower oil. Anim. Feed Sci. Technol. 119, 203-225, https://doi.org/10.1016/j. anifeedsci.2005.01.001
49. Manso T., Gallardo B., Guerra-Rivas C., 2016. Modifying milk and meat fat quality through feed changes. Small Rumin. Res. 142, 31-37, https://doi.org/10.1016/j.smallrumres.2016.03.003
50. Mapiye C., Aalhus J. L., Turner T. D. et al., 2013b. Effects of feeding flaxseed or sunflower-seed in high-forage diets on beef production, quality and fatty acid composition. Meat Sci. 95, 98-109, https://doi.org/10.1016/j.meatsci.2013.03.033
51. Mapiye C., Turner T. D., Rolland D. C., Basarab J. A., Baron V. S., McAllister T. A., Block H. C., Uttaro B., Aalhus J. L., Dugan M. E. R., 2013a. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without faxseed. Livest. Sci. 151, 11-20, https://doi.org/10.1016/j.livsci.2012.10.021
52. Mapiye C., Vahmani P., Mlambo V., Muchenje V., Dzama K., Hoffman L. C., Dugan M. E. R., 2015. The trans-octadecenoic fatty acid profile of beef: Implications for global food and nutrition security. Food Res. Int. 76, 992-1000, https://doi.org/10.1016/j. foodres.2015.05.001
53. Melo I. L. P., de Carvalho E. B. T., Silva A. M. O, Yoshmine L. T., Sattler J. A. G., Pavan R. T., Mancini-Filho J., 2016. Characterization of constituents, quality and stability of pomegranate seed oil (Punica granatum L.). Food Sci. Technol. 36, 132-139, https://doi.org/10.1590/1678-457X.0069
54. Mills S., Ross R. P., Hill C., Fitzgerald G. F., Stanton C., 2011. Milk intelligence: Mining milk for bioactive substances associated with human health. Int. Dairy J. 21, 377-401, https://doi.org/10.1016/j.idairyj.2010.12.011
55. Modaresi J., Fathi Nasri M. H., Rashidi L., Dayani O., Kebreab E., 2011. Effect of supplementation with pomegranate seed pulp on concentrations of conjugated linoleic acid and punicic acid in goat milk. J. Dairy Sci. 94, 4075-4080, https://doi.org/10.3168/jds.2010-4069
56. Nekooeian A. A., Eftekhari M. H., Adibi S., Rajaeifard A., 2014. Effect of pomegranate seed oil on insulin release in rats with type 2 diabetes. Iran. J. Med. Sci. 39, 130-135
57. Ogawa J., Kishino S., Ando A., Sugimoto S., Mihara K., Shimizu S., 2005. Production of conjugated fatty acids by lactic acid bacteria. J. Biosci. Bioeng. 100, 355-364, https://doi.org/10.1263/jbb.100.355
58. Park Y., Pariza M. W., 2007. Mechanisms of body fat modulation by conjugated linoleic acid (CLA). Food Res. Int. 40, 311-323, https://doi.org/10.1016/j.foodres.2006.11.002
59. Pariza M. W., Ashoor S. H., Chu F. S., Lund D. B., 1979. Effects of temperature and time on mutagen formation in pan-fried hamburger. Cancer Lett. 7, 63-69, https://doi.org/10.1016/S0304-3835 (79) 80097-X
60. Pariza M. W., Park Y., Cook M. E., 1999. Conjugated linoleic acid and the control of cancer and obesity. Toxicol. Sci. 52, Suppl. 1, 107-110, https://doi.org/10.1093/toxsci/52.suppl-1.107
61. Petersen M. B., 2014. The effect of forbs on rumen biohydrogenation of fatty acids and bovine milk fatty acid composition. PhD Thesis, Aarhus University, Aarhus (Denmark)
62. Plourde M., Destaillats F., Chouinard P. Y., Angers P., 2007. Conjugated α-linolenic acid isomers in bovine milk and muscle. J. Dairy Sci. 90, 5269-5275, https://doi.org/10.3168/jds.2007-0157
63. Plourde M., Sergiel J.-P., Chardigny J.-M., Grégoire S., Angers P., Sébédio J.-L., 2006. Absorption and metabolism of conjugated α-linolenic acid given as free fatty acids or triacyloglycerols in rats. Nutr. Metab. 3, 8, https://doi.org/10.1186/1743-7075-3-8
64. Ray R. B., Raychoudhuri A., Steele R., Nerurkar P., 2010. Bitter Melon (Momordica charantia) extract inhibits breast cancer cell proliferation by modulating cell cycle regulatory genes and promotes apoptosis. Cancer Res. 70, 1925-1931, https://doi.org/10.1158/0008-5472. CAN-09-3438
65. Razzaghi A., Naserian A. A., Valizadeh R., Ebrahimi S. H., Khorrami B., Malekkhahi M., Khiaosa-ard R., 2015. Pomegranate seed pulp, pistachio hulls and tomato pomace as replacement of wheat bran increased milk conjugated linoleic acid concentrations without adverse effects on ruminal fermentation and performance of Saanen dairy goats. Anim. Feed Sci. Technol. 210, 46-55, https://doi.org/10.1016/j.anifeedsci.2015.09.014
66. Rego O. A., Alves S. P., Antunes L. M. S., Rosa H. J. D., Alfaia C. F. M., Prates J. A. M., Cabrita A. R. J., Fonseca A. J. M., Bessa R. J. B., 2009. Rumen biohydrogenation-derived fatty acids in milk fat from grazing dairy cows supplemented with rapeseed, sunflower, or linseed oils. J. Dairy Sci. 92, 4530-4540, https://doi.org/10.3168/jds.2009-2060
67. Roach J. A. G., Mossoba M. M., Yurawecz M. P., Kramer J. K. G., 2002. Chromatographic separation and identification of conjugated linoleic acid isomers. Anal. Chim. Acta 465, 207-226, https://doi.org/10.1016/S0003-2670 (02) 00193-9
68. Saha S. S., Ghosh M., 2009. Comparative study of antioxidant activity of α-eleostearic acid and punicic acid against oxidative stress generated by sodium arsenite. Food Chem. Toxicol. 47, 2551-2556, https://doi.org/10.1016/j.fct.2009.07.012
69. Saliba L., Gervais R., Lebeuf Y., Chouinard P. Y., 2014. Effect of feeding linseed oil in diets differing in forage to concentrate ratio: 1. Production performance and milk fat content of biohydrogenation intermediates of α-linolenic acid. J. Dairy Res. 81, 82-90, https://doi.org/10.1017/S0022029913000691
70. Shingfield K. J., Bernard L., Leroux C., Chilliard Y., 2010a. Role of trans fatty acids in the nutritional regulation of mammary lipogenesis in ruminants. Animal 4, 1140-1166, https://doi.org/10.1017/S1751731110000510
71. Shingfield K. J., Bonnet M., Scollan N. D., 2013. Recent developments in altering the fatty acid composition of ruminant-derived foods. Animal 7, Suppl. 1, 132-162, https://doi.org/10.1017/S1751731112001681
72. Shingfield K. J., Lee M. R. F., Humphries D. J., Scollan N. D., Toivonen V., Reynolds C. K., Beever D. E., 2010b. Effect of incremental amounts of fish oil in the diet on ruminal lipid metabolism in growing steers. Br. J. Nutr. 104, 56-66, https://doi.org/10.1017/S0007114510000292
73. Shinohara N., Tsuduki T., Ito J. et al., 2012. Jacaric acid, a linolenic acid isomer with a conjugated triene system, has a strong antitumor effect in vitro and in vivo. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1821, 980-988, https://doi.org/10.1016/j. bbalip. 2012.04.001
74. Sinclair L. A., 2007. Nutritional manipulation of the fatty acid composition of sheep meat: a review. J. Agric. Sci. 145, 419-434, https://doi.org/10.1017/S0021859607007186
75. Stolyhwo A., Rutkowska J., 2013. An improved silver ion HPLC combined with capillary gas chromatography of cis/trans fatty acids in alimentary fats and human milk fat. Food Anal. Methods 6, 457-469, https://doi.org/10.1007/s12161-012-9454-y
76. Tanaka K., 2005. Occurrence of conjugated linoleic acid in ruminant products and its physiological functions. Animal Sci. J. 76, 291-303, https://doi.org/10.1111/j.1740-0929.2005.00268.x
77. Tsuzuki T., Kawakami Y., Abe R., Nakagawa K., Koba K., Imamura J., Iwata T., Ikeda I., Miyazawa T., 2006. Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid. J. Nutr. 136, 2153-2159
78. Tsuzuki T., Tokuyama Y., Igarashi M., Nakagawa K., Ohsaki Y., Komai M., Miyazawa T., 2004. α-Eleostearic acid (9z11E13E-18:3) is quickly converted to conjugated linoleic acid (9Z11E-18:2) in rats. J. Nutr. 134, 2634-2639
79. Turner T. D., Meadus W. J., Mapiye C., Vahmani P., López-Campos O., Duff P., Rolland D. C., Church J. S., Dugan M. E. R., 2015. Isolation of α-linolenic acid biohydrogenation products by combined silver ion solid phase extraction and semi-preparative high performance liquid chromatography. J. Chromatogr. B 980, 34-40, https://doi.org/10.1016/j.jchromb.2014.11.038
80. Vroegrijk I. O. C. M., van Diepen J. A., van den Berg S. et al., 2011. Pomegranate seed oil, a rich source of punicic acid, prevents diet-induced obesity and insulin resistance in mice. Food Chem. Toxicol. 49, 1426-1430, https://doi.org/10.1016/j. fct.2011.03.037
81. Wallace R. J., McKain N., Shingfield K. J., Devillard E., 2007. Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. J. Lipid Res. 48, 2247-2254, https://doi.org/10.1194/jlr. M700271-JLR200
82. Wąsowska I., Maia M. R. G., Niedźwiedzka K. M., Czauderna M., Ramalho Ribeiro J. M. C., Devillard E., Shingfield K. J., Wallace R. J., 2006. Influence of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids. Br. J. Nutr. 95, 1199-1211, https://doi.org/10.1079/BJN20061783
83. Wood J. D., Enser M., Fisher A. V., Nute G. R., Sheard P. R., Richardson R. I., Hughes S. I., Whittington F. M., 2008. Fat deposition, fatty acid composition and meat quality: A review. Meat Sci. 78, 343-358, https://doi.org/10.1016/j.meatsci.2007.07.019
84. Yasui Y., Hosokawa M., Kohno H., Tanaka T., Miyashita K., 2006. Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells. Anticancer Res. 26, 1855-1860
85. Yuan G., Sinclair A. J., Xu C., Li D., 2009a. Incorporation and metabolism of punicic acid in healthy young humans. Mol. Nutr. Food Res. 53, 1336-1342, https://doi.org/10.1002/mnfr.200800520
86. Yuan G.-F., Chen X.-E., Li D., 2014. Conjugated linolenic acids and their bioacitivities: a review. Food Funct. 5, 1360-1368, https://doi.org/10.1039/c4fo00037d
87. Yuan G.-F., Sinclair A. J., Sun H.-Y., Li D., 2009b. Fatty acid composition in tissues of mice fed diets containing conjugated linolenic acid and conjugated linoleic acid. J. Food Lipids 16, 148-163, https://doi.org/10.1111/j.1745-4522.2009.01138.x
88. Yuan G.-F., Wahlqvist M. L., Yuan J.-Q., Wang Q.-M., Li D., 2009c. Effect of punicic acid naturally occurring in food on lipid peroxidation in healthy young humans. J. Sci. Food Agric. 89, 2331-2335, https://doi.org/10.1002/jsfa.3729
89. Zened A., Troegeler-Meynadier A., Nicot M. C., Combes S., Cauquil L., Farizon Y., Enjalbert F., 2011. Starch and oil in the donor cow diet and starch in substrate differently affect the in vitro ruminal biohydrogenation of linoleic and linolenic acids. J. Dairy Sci. 94, 5634-5645, https://doi.org/10.3168/jds.2011-4491