Conjugated linoleic acid synthesis

Figure 4.1 Biosynthetic pathways of those CLA isomers present in the most abundant quantities in human foods. Ruminal formation is marked with sohd arrow, while formation in other organs by A -desaturase reaction is shown with dotted arrows (according to CoUomb et al. (2006), Buccioni et al. (2012) and Lerch et al. (2012)). Question marks indicate that the exact mechanism is unclear. The underlined compounds are the conjugated linoleic acid isomers. The compounds without underline are the intermediaries of conjugated linoleic acid synthesis.

Conjugated Linoleic Acid Synthesis within the Gut Microbial Ecosystem of Ruminants... 

Lie and coworkers31 reported the synthesis and NMR properties of all geometrical isomers of conjugated linoleic acids. Pure geometric isomers of conjugated linoleic acid (CLA) were prepared from castor oil as the primary starting material. Methyl octadeca-9Z, 11 /i-dienoate (36) and methyl octadeca-9Z,llZ-dienoate (38) were obtained by zinc reduction of methyl santalbate (35, methyl octadec-11 -en-9-ynoatc) and methyl... 

Liu, K-L. and Belury, M.A., Conjugated linoleic acid reduces arachidonic acid content and PGE2 synthesis in murine keratinocytes, Cancer Lett., 1 A, 1050, 1998. 

Baumgard, L.H., Corl, B.A., Dwyer, D.A., Saebo, A., Bauman, D.E. 2000. Identification of the conjugated linoleic acid isomer that inhibits milk fat synthesis. Am. J. Physiol. 278, R179-184. 

Baumgard, L.H., Sangster, J.K., Bauman, D.E. 2001. Milk fat synthesis in dairy cows is progressively reduced by increasing supplemental amounts of trans-10, cis-12 conjugated linoleic acid (CLA). J. Nutr. 131, 1764-1769. 

Loor, J.J., Herbein, J.H. 1998. Exogenous conjugated linoleic acid isomers reduce bovine milk fat concentration and yield by inhibiting de novo fatty acid synthesis. J. Nutr. 128, 2411-2419. 

Moore, C.E., Hafliger, H.C., Mendivil, O.B., Sanders, S.R., Bauman, D.E., Baumgard, L.H. 2004. Increasing amounts of conjugated linoleic acid (CLA) progressively reduces milk fat synthesis immediately postpartum. J. Dairy Sci. 87, 1886-1895. 

Piperova, L.S., Sampugna, J., Teter, B.B., Kalscheur, K.F., Yurawecz, M.P., Ku, Y., Morehouse, K.M., Erdman, R.A. 2002. Duodenal and milk trans octadecenoic acid and conjugated linoleic acid (CLA) isomers indicate that postabsorptive synthesis is the predominant source of cis-9-containing CLA in lactating dairy cows. J. Nutr. 132, 1235-1241. 

Takahashi, Y., Kushiro, M., Shinohara, K., and Ide,T. 2003. Activity and mRNA levels of enzymes involved in hepatic fatty acid synthesis and oxidation in mice fed conjugated linoleic acid. Biochim. Biophys. Acta, 1631, 265-273. 

Over the last two decades, the conjugated fats and, particularly, conjugated linoleic acid (CLA) have been intensively studied for their biological activity. As a result of the ease of synthesis, blends of two CLA isomers, namely 9,11-ct and 10,12-tc-CLA, have been the focus of most research into biological activity. Recent research, however, has been expanding to include pure or enriched isomer preparations. 

M. Hossen and E. Hernandez Enzyme-catalyzed synthesis of structured phospholipids with conjugated linoleic acid. European Journal of Lipid and Science and Technology 107 (2005) 730-736. 

Garcia, H.S., Arcos, J.A., Ward, D.J., and Hill Jr., C.G. 2000. Synthesis of glycerides containing n-3 fatty acids and conjugated linoleic acid by solvent-free acidolysis of fish oil, Biotechnol. Bioeng., 70, 587-591. 

Chung, S.FL, Kim, I.H, Park, H.G., Kang, H.S. et al (2008) Synthesis of conjugated linoleic acid by human-derived Bifidobacterium breve LMC 017 utilization as a functional starter culture for milk fermentation. ). Agric. Food Chem., 56, 3311-3316. 

Yang, B., Chen, FL, Gu, Z., Tian, F. et al (2014) Synthesis of conjugated linoleic acid by the linoleate isomerase complex in food-derived lactobacilli. 

Kay, J. K., Mackle, T. R., Auldist, M. J., Thomson, N. A., Bauman, D. E. (2004). Endogenous synthesis of cis-9,trans-11 conjugated linoleic acid in dairy cows fed fresh pasture. Journal of Dairy Science, 87, 369-378. 

Piperova, L.S., J. Sampugna, B.B. Teter, K.F. Kalscheur, M.P Yurawecz, Y. Ku, K.M. Morehouse, and R.A. Erdman. Duodenal and Milk Trans Octadecenoic Acid and Conjugated Linoleic Acid (CLA) Isomers Indicate that Postabsorptive Synthesis is the Predominant Source of Cw-9-Containing CLA in Lactating Dairy Cows. J. Nutr. 132 1235-1241 (2002). 

Destaillats, F. and P. Angers. Directed Sequential Synthesis of Conjugated Linoleic Acid... 

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