Abstract
Most studies of linoleic acid biohydrogenation propose that it converts to stearic acid through the production of cis-9 trans-11 CLA and trans-11 C18:1. However, several other CLA have been identified in ruminai contents, suggesting additional pathways may exist. To explore this possibility, this research investigated the linoleic acid biohydrogenation pathway to identify CLA isomers in cultures of ruminai microorganisms after dosing with a 13C stable isotope. The 13C enrichment was calculated as [(M+1/M)×100] in labeled minus unlabeled cultures. After 48 h incubation, significant 13C enrichment was observed in seven CLA isomers, indicating their formation from linoleic acid. All enriched CLA isomers had double bonds in either the 9,11 or 10,12 position except for trans-9 cis-11 CLA. The cis-9 trans-11 CLA exhibited the highest enrichment (30.65%), followed by enrichments from 21.06 to 23.08% for trans-10 cis-12, cis-10 trans-12, trans-9 trans-11, and trans-10 trans-12 CLA. The remaining two CLA (cis-9 cis-11 and cis-10 cis-12 CLA) exhibited enrichments of 18.38 and 19.29%, respectively. The results of this study verified the formation of cis-9 trans-11 and trans-10 cis-12 CLA isomers from linoleic acid biohydrogenation. An additional five CLA isomers also contained carbons originating from linoleic acid, indicating that pathways of linoleic acid biohydrogenation are more complex than previously described.
Similar content being viewed by others
References
Beam, T.M., T.C. Jenkins, P.J. Moate, R.A. Kohn, and D.L. Palmquist. 2000. Effects of amount and source of fat on the rates of lipolysis and biohydrogenation of fatty acids in ruminal contents. J. Dairy Sci. 83, 2564–2573.
Coakley, M., M.C. Johnson, E. McGrath, S. Rahman, R.P. Ross, G.F. Fitzgerald, R. Devery, and C. Stanton. 2006. 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. Nutr. Cancer 56, 95–102.
DeLany, J.P. and D.B. West. 2000. Changes in body composition with conjugated linoleic acid. J. Am. Coo. Nutr. 19, 487S–493S.
Duckett, S.K., J.G. Andrae, and F.N. Owens. 2002. Effect of high-oil corn or added corn oil on ruminal biohydrogenation of fatty acids and conjugated linoleic acid formation of beef steers fed finishing diets. J. Anim. Sci. 80, 3353–3360.
Goering, H.K. and P.J. Van Soest. 1970. Forage fiber analysis. Agric. Handbook No. 379. ARS, USDA, Washington, DC, USA.
Griinari, J.M. and D.E. Bauman. 1999. Biosynthesis of conjugated linoleic acid and its incorporation into meat and milk in ruminants, Vol. 1., pp. 180–200 in Advances in Conjugated Linoleic Acid Research, In M.P. Yurawecz, M.M. Mossoba, J.K.G. Kramer, M.W. Pariza, and G.J. Nelson (ed.). AOCS Press, Champaign, IL, USA.
Griinari, J.M., B.A. Corl, S.H. Lacy, P.Y. Chouinard, K.V. Nurmela, and D.E. Bauman. 2000. Conjugated linoleic acid is synthesized endogenously in lactating dairy cows by Δ(9)-desaturase, J. Nutr. 130, 2285–2291.
Harfoot, C.G. and G.P. Hazlewood. 1997. Lipid metabolism in the rumen. In P.N. Hobson and C.S. Stewart (eds.), The rumen microbial ecosystem, pp. 382–426. Chapman and Hall, London, UK.
Ip, C., S. Banni, E. Angioni, G. Carta, J. McGinley, H.J. Thompson, D. Barbano, and D.E. Bauman. 1999. Conjugated linoleic acid-enriched butter fat alters mammary gland morphogenesis and reduces cancer risk in rats. J. Nutr. 129, 2135–2142.
Jenkins, T.C., R.J. Wallace, P.J. Moate, and E.E. Mosley. 2008. Board-invited review: Recent advances in biohydrogenation of unsaturated fatty acids within the rumen microbial ecosystem. J. Anim. Sci. 86, 397–412.
Jiang, J., L. Bjorck, and R. Fonden. 1998. Production of conjugated linoleic acid by dairy starter cultures. J. Appl. Microbiol. 85, 95–102.
Kellens, M.J., H.L. Goderis, and P.P. Tobback. 1986. Biohydrogenation of unsaturated fatty acids by a mixed culture of rumen microorganisms. Biotechnol. Bioeng. 28, 1268–1276.
Kemp, P., R.W. White, and D.L. Lander. 1975. The hydrogenation of unsaturated fatty acids by five bacterial isolates from the sheep rumen, including a new species. J. Gen. Microbiol. 90, 100–114.
Kim, Y.J., R.H. Liu, D.R. Bond, and J.B. Russell. 2000. Effect of linoleic acid concentration on conjugated linoleic acid production by Butyrivibrio fibrisolvens A38. Appl. Environ. Microbiol. 66, 5226–5230.
Kim, Y.J., R.H. Liu, K.L. Rychlik, and J.B. Russell. 2002. The enrichment of a ruminal bacterium (Megasphaera elsdenii YJ-4) that produces the trans-10, cis-12 isomer of conjugated linoleic acid. J. Appl. Microbiol. 92, 976–982.
Kramer, J.K.G., V. Fellner, M.E.R. Dugan, F.D. Sauer, M.M. Mossoba, and M.P. Yurawecz. 1997. Evaluating acid and base catalysts in the methylation of milk and rumen fatty acids with special emphasis on conjugated dienes and total trans fatty acids. Lipids 32, 1219–1228.
Lawrence, P. and J.T. Brenna. 2006. Acetonitrile covalent adduct chemical ionization mass spectrometry for double bond localization in non-methylene-interrupted polyene fatty acid methyl esters. Anal. Chem. 78, 1312–1317.
Liavonchanka, A., E. Hornung, I. Feussner, and M.G. Rudolph. 2006. Structure and mechanism of the Propionibacterium acnes polyunsaturated fatty acid isomerase. Proc. Natl. Acad. Sci. USA 103, 2576–2581.
Maia, M.R.G., L.C. Chaudhary, L. Figueres, and R.J. Wallace. 2006. Metabolism of polyunsaturated fatty acids and their toxicity to the microflora of the rumen. Antonie van Leeuwenhoek 91, 303–314.
Michaud, A.L., G.Y. Diau, R. Abril, and J.T. Brenna. 2002. Double bond localization in minor homoallylic fatty acid methyl esters using acetonitrile chemical ionization tandem mass spectrometry. Anal. Biochem. 307, 348–360.
Michaud, A.L., M.P. Yurawecz, P. Delmonte, B.A. Corl, D.E. Bauman, and J.T. Brenna. 2003. Identification and characterization of conjugated fatty acid methyl esters of mixed double bond geometry by acetonitril chemical ionization tandem mass spectrometry. Anal. Chem. 75, 4925–4930.
Mosley, E.E., G.L. Powell, M.B. Riley, and T.C. Jenkins. 2002. Microbial biohydrogenation of oleic acid to trans isomers in vitro. J. Lipid Res. 43, 290–296.
Nam, I.S. and P.C. Garnsworthy. 2007a. Biohydrogenation of linoleic acid by rumen fungi compared with rumen bacteria. J. Appl. Microbiol. 103, 551–556.
Nam, I.S. and P.C. Garnsworthy. 2007b. Factors influencing biohydrogenation and conjugated linoleic acid production by mixed rumen fungi. J. Microbiol. 45, 199–204.
Ogawa, J., J. Matsumura, S. Kishino, Y. Omura, and S. Shimizu. 2001. Conjugated linoleic acid accumulation via 10-hydroxy-12-octadecaenoic acid during microaerobic transformation of linoleic acid by Lactobacillus acidophilus. Appl. Environ. Microbiol. 67, 1246–1252.
Pariza, M.W. 2004. Perspective on the safety and effectiveness of conjugated linoleic acid. Am. J. Clin. Nutr. 79, 1132–1136.
Piperova, L.S., J. Sampugna, B.B. Teter, K.F. Kalscheur, M.P. Yurawecz, Y. Ku, K.M. Morehouse, and R.A. Erdman. 2002. Duodenal and milk trans octadecenoic acid and conjuaged 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.
Proell, J.M., E.E. Mosley, G.L. Powell, and T.C. Jenkins. 2002. Isomerization of stable isotopically labeled elaidic acid to cis and trans monoenes by rumincl microbes. J. Lipid Res. 43, 2072–2076.
Ryder, J.W., C.P. Portocarrero, X.M. Song, L. Cui, and M. Yu. 2001. Isomer specific antidiabetic properties of conjugated linoleic acid. Improved glucose tolerance, skeletal muscle insulin action and UCP-2 gene expression. Diabetes 50, 1149–1157.
Shingfield, K.J., S. Ahvenjarvi, V. Toivonen, A. Arola, K.V.V. Nurmela, P. Huhtanen, and J.M. Griinari. 2003. Effect of fish oil on biohydrogenation of fatty acids and milk fatty acid content in cows. Anim. Sci. 77, 165–179.
Van Pelt, C.K. and J.T. Brenna. 1999. Acetonitrile chemical ionization tandem mass spectrometry to locate double bonds in polyunsaturated fatty acid methyl esters. Anal. Chem. 71, 1981–1989.
Van Nevel, C. and D.I. Demeryer. 1996. Influence of pH on lipolysis and biohydrogenation of soybean oil by rumen contents in vitro. Reprod. Nutr. Dev. 36, 53–63.
Wahle, K.W., S.D. Heys, and D. Rotondo. 2004. Conjugated linoleic acids: Are they beneficial or detrimental to health? Prog. Lipid Res. 43, 553–587.
Wu, Z., O.A. Ohajuruka, and D.L. Palmquist. 1991. Ruminal synthesis, biohydrogenation, and digestibilities of fatty acids by dairy cows. J. Dairy Sci. 74, 3025–3034.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, YJ., Jenkins, T.C. Identification of enriched conjugated linoleic acid isomers in cultures of ruminal microorganisms after dosing with 1-13C-linoleic acid. J Microbiol. 49, 622–627 (2011). https://doi.org/10.1007/s12275-011-0415-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12275-011-0415-8