Literature Survey

Analysis of Conjugated Fatty Acids (including CLA)

 

There is increasing interest in conjugated linoleic acid (CLA) because of its potential therapeutic properties. Analytical methodology is especially importance now that it is recognized that different isomers may behave differently in biological systems. I can recommend the review by Banni & Martin cited in full below, together with a number of articles in the books - Advances in Conjugated Linoleic Acid Research, Vols. 1-3, published by AOCS Press.

The following references deal with analysis of conjugated fatty acids in general as well as conjugated linoleic acid specifically. They were collected as part of our regular literature reviews for our own research purposes, and cover the years 1964 to the present. We cannot claim to have covered the subject exhaustively, but we have done our best. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author.

  • Adlof,R. and Lamm,T. Fractionation of cis-and trans-oleic, linoleic, and conjugated linoleic fatty acid methyl esters by silver ion high-performance liquid chromatography. J. Chromatogr. A, 799, 329-332 (1998).
  • Adlof,R.O. The Lindlar-catalyzed reduction of methyl santalbate: A facile preparation of methyl 9-cis,11-trans-octadecadienoate-9,10-d(2). J. Am. Oil Chem. Soc., 76, 301-304 (1999).
  • Adlof,R.O. Separation of conjugated linoleic acid-containing mono-, di-and triacylglycerols by silver-ion high-performance liquid chromatography. Eur. J. Lipid Sci. Technol., 103, 614-617 (2001).
  • Adlof,R.O. Application of silver ion chromatography to the separation of conjugated linoleic acid isomers. In: Advances in Conjugated Linoleic Acid Research, Volume 2., pp. 37-55 (edited by J.L. Sebedio, W.W. Christie & R.O. Adlof, AOCS Press, Champaign, IL.) (2003).
  • Adlof,R.O. Separation of conjugated linoleic acid methyl esters by silver-ion high performance liquid chromatography in semi-preparative mode. J. Chromatogr. A, 1033, 369-371 (2004).
  • Adlof,R.O., Copes,L.C. and Walter,E.L. Changes in conjugated linoleic acid composition within samples obtained from a single source. Lipids, 36, 315-317 (2001).
  • Adlof,R.O., Menzel,A. and Dorovska-Taran,V. Analysis of conjugated linoleic acid-enriched triacylglycerol mixtures by isocratic silver-ion high-performance liquid chromatography. J. Chromatogr. A, 953, 293-297 (2002).
  • Aldai,N., Murray,B.E., Najera,A.I., Troy,D.J. and Osoro,K. Derivatization of fatty acids and its application for conjugated linoleic acid studies in ruminant meat lipids. J. Sci. Food Agric., 85, 1073-1083 (2005).
  • Alves,S.P., Maia, M.R.G., Bessa, R.J.B., Fonseca, A.J.M. and Cabrita, A.R.J. Identification of C18 intermediates formed during stearidonic acid biohydrogenation by rumen microorganisms in vitro. Lipids, 47, 171-183 (2012).
  • Ando,T., Ogura,Y. and Uchiyama,M. Mass spectra of lipidopterous sex pheromones with a conjugated diene system. Agric. Biol. Chem., 52, 1415-1423 (1988).
  • Angioni,E., Lercker,G. , Frega,N.G., Carta,G., Melis,M.P., Murru,E., Spada,S. and Banni,S. UV spectral properties of lipids as a tool for their identification. Eur. J. Lipid Sci. Technol., 104, 59-64 (2002).
  • Attygalle,A.B., Svatos,A., Wilcox,C. and Voerman,S. Gas-phase infrared-spectroscopy for determination of double bond configuration of some polyunsaturated pheromones and related compounds. Anal. Chem., 67, 1558-1567 (1995).
  • Bang,M.H., Han,J.T., Kim,H.Y., Park,Y.D., Park,C.H., Lee,K.R. and Baek,N.I. 13-hydroxy-9Z,11E,15E-octadecatrienoic acid from the leaves of Cucurbita moschata. Arch. Pharm. Res., 25, 438-440 (2002).
  • Banni,S. and Martin,J.-C. Conjugated linoleic acid and metabolites. In: Trans Fatty Acids in Human Nutrition, pp. 261-302 (edited by J.L. Sebedio and W.W. Christie, Oily Press, Dundee) (1998).
  • Banni,S., Carta,G., Contini,M.S., Angioni,E., Deiana,M., Dessi,M.A., Melis,M.P. and Corongiu,F.P. Characterization of conjugated diene fatty acids in milk, dairy products, and lamb tissues. J. Nutr. Biochem., 7, 150-155 (1996).
  • Banni,S., Day,B.W., Evans,R.W., Corongiu,F.P. and Lombardi,B. Detection of conjugated diene isomers of linoleic acid in liver lipids of rats fed a choline-devoid diet indicates that the diet does not cause lipoperoxidation. J. Nutr. Biochem., 6, 281-289 (1995).
  • Banni,S., Day,B.W., Evans,R.W., Corongui,F.P. and Lombardi,B. Liquid chromatographic-mass spectrometric analysis of conjugated diene fatty acids in a partially hydrogenated fat. J. Am. Oil Chem. Soc., 71, 1321-1325 (1994).
  • Banni,S., Petroni,A., Blasevich,M., Carta,G., Angioni,E., Murru,E., Day,B.W., Melis,M.P., Spada,S. and Ip,C. Detection of conjugated C16 PUFAs in rat tissues as possible partial beta-oxidation products of naturally occurring conjugated linoleic acid and its metabolites. Biochim. Biophys. Acta, 1682, 120-127 (2004).
  • Berdeaux,O., Christie,W.W., Gunstone,F.D. and Sebedio,J.L. Large-scale synthesis of methyl cis-9,trans-11-octadecadienoate from methyl ricinoleate. J. Am. Oil Chem. Soc., 74, 1011-1015 (1997).
  • Berdeaux,O., Juaneda,P. and Sebedio,J.L. Analysis of conjugated and trans fatty acids after derivatization. Analusis, 26, M45-M51 (1998).
  • Berdeaux,O., Voinot,L., Angioni,E., Juaneda,P. and Sebedio,J.L. A simple method of preparation of methyl trans-10,cis-12-and cis-9,trans-11-octadecadienoates from methyl linoleate. J. Am. Oil Chem. Soc., 75, 1749-1755 (1998).
  • Bergter,L. and Seidl,P.R. Complete assignment of the C13 NMR spectrum of oiticica oil: interpretation of chemical shifts in conjugated systems. Lipids, 19, 44-47 (1984).
  • Blasi,F., Giua,L., Lombardi,G., Codini,M., Simonetti,M.S., Damiani,P. and Cossignani,L. Improved HRGC separation of cis,trans CLA isomers as Diels-Alder adducts of alkyl esters. J. Chromatogr. Sci., 49, 379-383 (2011).
  • Blasko,J., Kubinec,R., Ostrovsky,I., Pavlikova,E., Krupcik,J. and Sojak,L. Chemometric deconvolution of gas chromatographic unresolved conjugated linoleic acid isomers triplet in milk samples. J. Chromatogr. A, 1216, 2757-2761 (2009).
  • Bohlin,M.E., Ohman,M., Hamberg,M. and Blomberg,L.G. Separation of conjugated trienoic fatty acid isomers by capillary electrophoresis. J. Chromatogr. A, 985, 471-478 (2003).
  • Bondia-Pons,I., Molto-Puigmarti,C., Castellote,A.I. and Lopez-Sabater,M.C. Determination of conjugated linoleic acid in human plasma by fast gas chromatography. J. Chromatogr. A, 1157, 422-429 (2007).
  • Broadwater,J.A., Laundre,B.J. and Fox,B.G. Desaturation of trans-octadecenoyl-acyl carrier protein by stearoyl-acyl carrier protein Delta(9) desaturase. J. Inorganic Biochem., 78, 7-14 (2000).
  • Brutting,R. and Spiteller,G. Products of dimerization of unsaturated fatty acids. 12. The dimerization of conjugated fatty acids. Fat Sci. Technol., 96, 445-451 (1994).
  • Cahoon,E.B., Ripp,K.G., Hall,S.E. and Kinney,A.J. Formation of conjugated Delta(8),Delta(10)-double bonds by Delta(12)-oleic-acid desaturase-related enzymes - Biosynthetic origin of calendic acid. J. Biol. Chem., 276, 2637-2643 (2001).
  • Cao,Y., Gao,H.-L., Chen,J.-N., Chen,Z.-Y. and Yang,L. Identification and characterization of conjugated linolenic acid isomers by Ag+HPLC and NMR. J. Agric. Food Chem., 54, 9004-9009 (2006).
  • Cao, Y., Yang,L., Gao,H.L., Chen,J.N., Chen,Z.Y. and Ren,Q.S. Re-characterization of three conjugated linolenic acid isomers by GC-MS and NMR. Chem. Phys. Lipids, 145, 128-133 (2007).
  • Chang, M.-K., Conkerton,E.J., Chapital,D. and Wan,P.J. Behaviour of diglycerides and conjugated fatty acid triglycerides in reverse-phase chromatography. J. Am. Oil Chem. Soc., 71, 1173-1175 (1994).
  • Chen,J., Cao,Y., Gao,H., Yang,L. and Chen,Z.-Y. Isomerization of conjugated linolenic acids during methylation. Chem. Phys. Lipids, 150, 136-142 (2007).
  • Chin,S.F., Liu,W., Storkson,J.M., Ha,Y.L. and Pariza,M.W. Dietary sources of conjugated dienoic isomers of linoleic acid, a newly recognised class of anticarcinogens. J. Food Comp. Anal., 5, 185-197 (1992).
  • Chisaguano, A.M., Lozano, B., Molto-Puigmarti, C., Castellote, A.I., Rafecas, M. and Lopez-Sabater, M.C. Elaidic acid, vaccenic acid and rumenic acid (c9, t11-CLA) determination in human plasma phospholipids and human milk by fast gas chromatography. Anal. Methods, 5, 1264-1272 (2013).
  • Chouinard, P.Y., Corneau,L., Barbano,D.M., Metzger,L.E. and Bauman,D.E. Conjugated linoleic acids alter milk fatty acid composition and inhibit milk fat secretion in dairy cows. J. Nutr., 129, 1579-1584 (1999).
  • Christie, W.W. Analysis of conjugated linoleic acid - an overview. In: Advances in Conjugated Linoleic Acid Research, Volume 2., pp. 1-12 (edited by J.L. Sebedio, W.W. Christie & R.O. Adlof, AOCS Press, Champaign, IL.) (2003).
  • Christie, W.W. and Han, X. Lipid Analysis - Isolation, Separation, Identification and Lipidomic Analysis (4th edition), 446 pages (Oily Press, Bridgwater, U.K. and Woodhead Publishing Ltd, Cambridge, U.K.) (2010) - Woodhead Publishing Ltd.
  • Christie, W.W., Dobson,G. and Adlof,R.O. A practical guide to the isolation, analysis and identification of conjugated linoleic acid. Lipids, 42, 1073-1084 (2007).
  • Christie, W.W., Dobson,G. and Gunstone,F.D. Isomers in commercial samples of conjugated linoleic acid. Lipids, 32, 1231 (1997).
  • Christie, W.W., Sébédio,J.L. and Juanéda,P. A practical guide to the analysis of conjugated linoleic acid (CLA). INFORM, 12, 147-152 (2001).
  • Christy, A.A. Infrared spectroscopy and partial least square calibration in the simultaneous quantification of isolated trans and conjugated linoleic acids. In: Lipid Analysis and Lipidomics: New Techniques and Applications. pp. 335-354 (ed: M.M. Mossoba, J.K.G. Kramer, J.T. Brenna and R.E. McDonald, AOCS Press, Champaign, USA) (2006).
  • Christy, A.A. Thermally induced isomerization of trilinolein and trilinoelaidin at 250 degrees C: analysis of products by gas chromatography and infrared spectroscopy. Lipids, 44, 1105-1112 (2009).
  • Christy, A.A. Evidence in the formation of conjugated linoleic acids from thermally induced 9t12t linoleic acid: a study by gas chromatography and infrared spectroscopy. Chem. Physics Lipids, 161, 86-94 (2009).
  • Christy, A.A. Isomerization of 9c11t/10t12c CLA in triacylglycerols. Lipids, 45, 733-741 (2010).
  • Christy, A.A., Egeberg,P.K. and Ostensen,E.T. Simultaneous quantitative determination of isolated trans fatty acids and conjugated linoleic acids in oils and fats by chemometric analysis of the infrared profiles. Vibrational Spectr., 33, 37-48 (2003).
  • Conacher, H.B.S., Gunstone,F.D., Hornby,G.M. and Padley,F.B. Glyceride studies. Part IX. Intraglyceride distribution of vernolic acid and of five conjugated octadecatrienoic acids in seed glycerides. Lipids, 5, 434-441 (1970).
  • Corl, B.A., Baumgard,L.H., Griinari,J.M., Delmonte,P., Morehouse,K.M., Yuraweczc,M.P. and Bauman,D.E. Trans-7,cis-9 CLA is synthesized endogenously by delta(9)-desaturase in dairy cows. Lipids, 37, 681-688 (2002).
  • Corongiu,F.P. and Banni,S. Detection of conjugated dienes by second derivative UV spectroscopy. Methods Enzymol., 233, 303-310 (1994).
  • Corongui,F.P., Banni,S. and Dessi,M.A. Conjugated dienes detected in tissue lipid extracts by second derivative spectroscopy. Free Radical Biol. Med., 7, 183-186 (1989).
  • Corongiu,F.P. and Milia,A. An improved and simple method for determining diene conjugation in autoxidized polyunsaturated fatty-acids. Chem.-Biol. Interact, 44, 289-297 (1983).
  • Cossignani, L., Giua, L., Lombardi, G., Simonetti, M.S., Damiani, P. and Blasi, F. Analysis of CLA isomer distribution in nutritional supplements by single column silver-ion HPLC. J. Am. Oil Chem. Soc., 90, 327-335 (2013).
  • Cross, R.F, Ostrowska,E., Muralitharan,H. and Dunshea,F.R. Mixed mode retention and the use of competing acid for the Ag+-HPLC analysis of underivatized conjugated linoleic acids. J. High Resolut. Chromatogr., 23, 317-323 (2000).
  • Cross, R.F. and Widman,H.A. Ag+ HPLC of conjugated linoleic acids on a silica-based stationary phase. Part I: Introduction, experimental, and retention patterns. J. Sep. Sci., 25, 239-244 (2002).
  • Cross, R.F. and Widman,H.A. Ag+ HPLC of conjugated linoleic acids on a silica-based stationary phase. Part II: Resolution and extrapolations. J. Sep. Sci., 25, 245-251 (2002).
  • Cross, R.F. and Zackari,H. Ag+HPLC of conjugated linoleic acids on a silica-based stationary phase. Part IV: A reference stationary phase and retention mechanisms. J. Sep. Sci., 26, 480-488 (2003).
  • Cross, R.F. and Zackari,H. Ag+HPLC of conjugated linoleic acids on a silica-based stationary phase. Part III: Model compounds. J. Sep. Sci., 25, 897-903 (2002).
  • Cruz-Hernandez, C., Deng,Z.Y., Zhou,J.Q., Hill,A.R., Yurawecz,M.P., Delmonte,P., Mossoba,M.M., Dugan,M.E.R. and Kramer,J.K.G. Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography. J. Ass. Off. Anal. Chem. Int., 87, 545-562 (2004).
  • Czauderna, M., Kowalczyk,J., Potkanski,A., Szumacher-Strabel,M. and Chojecki,G. Quantification of conjugated linoleic acid and other essential fatty acids in ovine meat, milk, fat, and intestinal digesta. J. Anim. Feed Sci., 10, 385-392 (2001).
  • Dannenberger,D., Nuernberg,K. and Nuernberg,G. Diet-dependent occurrence of CLA isomers in rumen and duodenal digesta of slaughtered bulls. Eur. J. Lipid Sci. Technol., 111, 553-562 (2009).
  • Davis,A.L., McNeill,G.P. and Caswell,D.C. Analysis of conjugated linoleic acid isomers by C-13 NMR spectroscopy. Chem. Phys. Lipids, 97, 155-165 (1999).
  • Davis,A.L., McNeill,G.P. and Caswell,D.C. Identification and quantification of conjugated linoleic acid isomers in fatty acid mixtures by 13C NMR spectroscopy. In: Advances in Conjugated Linoleic Acid Research, Vol. 1. (ed. M.P. Yurawecz, M.M. Mossoba, J.K.G. Kramer, M.W. Pariza and G.J. Nelson, AOCS Press, Champaign) pp. 164-179 (1999).
  • de la Fuente,M.A., Luna.P. and Juarez,M. Chromatographic techniques to determine conjugated linoleic acid isomers. Trends Anal. Chem., 25, 917-926 (2006).
  • Delmonte,P., Kataoka,A., Corl,B.A., Bauman,D.E. and Yurawecz,M.P. Relative retention order of all isomers of cis/trans conjugated linoleic acid FAME from the 6,8- to 13,15-positions using silver ion HPLC with two elution systems. Lipids, 40, 509-514 (2005).
  • Delmonte,P., Roach,J.A.G., Mossoba,M.M., Losi,G. and Yurawecz,M.P. Synthesis, isolation, and GC analysis of all the 6,8-to 13,15-cis/trans conjugated linoleic acid isomers. Lipids, 39, 185-191 (2004).
  • Delmonte,P., Roach,J.A.G., Mossoba,M.M., Morehouse,K.M., Lehmann,L. and Yurawecz,M.P. Synthesis and isolation of trans-7,cis-9 octadecadienoic acid and other CLA isomers by base conjugation of partially hydrogenated gamma-linolenic acid. Lipids, 38, 579-583 (2003).
  • Delmonte,P., Yurawecz,M.P., Mossoba,M.M., Cruz-Hernandez,C. and Kramer,J.K.G. Improved identification of conjugated linoleic acid isomers using silver-ion HPLC separations. J. Ass. Off. Anal. Chem. Int., 87, 563-568 (2004).
  • Destaillats,F. and Angers,P. Evidence for [1,5] sigmatropic rearrangements of CLA in heated oils. Lipids, 37, 435-438 (2002).
  • Destaillats,F. and Angers,P. Directed sequential synthesis of conjugated linoleic acid isomers from Delta(7,9) to Delta(12,14). Eur. J. Lipid Sci. Technol., 105, 3-8 (2003).
  • Destaillats,F., Berdeaux,O., Sebedio,J.L., Juaneda,P., Gregoire,S., Chardigny,J.M., Bretillon,L. and Angers,P. Metabolites of conjugated isomers of alpha-linolenic acid (CLnA) in the rat. J. Agric. Food Chem., 53, 1422-1427 (2005).
  • Destaillats,F., Sebedio,J.L., Berdeaux,O., Juaneda, P. and Angers,P. Gas chromatography-mass spectrometry determination of metabolites of conjugated cis-9,trans-11, cis-15 18:3 fatty acid. J. Chromatogr. B, 820, 15-22 (2005).
  • Devi,P.S. TLC as a tool for quantitative isolation of conjugated trienoic fatty acids. J. Am. Oil Chem. Soc., 80, 315-318 (2003).
  • Dionisi,F., Golay,P.A., Elli,M. and Fay,L.B. Stability of cyclopropane and conjugated linoleic acids during fatty acid quantification in lactic acid bacteria. Lipids, 34, 1107-1115 (1999).
  • Dobson,G. Gas chromatography-mass spectrometry of conjugated linoleic acid and metabolites. In: Advances in Conjugated Linoleic Acid Research, Volume 2., pp. 13-36 (edited by J.L. Sebedio, W.W. Christie & R.O. Adlof, AOCS Press, Champaign, IL.) (2003).
  • Dobson,G. Identification of conjugated fatty acids by gas chromatography mass spectrometry of 4-methyl-1,2,4-triazoline-3,5-dione adducts. J. Am. Oil Chem. Soc., 75, 137-142 (1998).
  • Dugan,M.E.R., Kramer,J.K.G., Robertson,W.M., Meadus,W.J., Aldai,N. and Rolland,D.C. Comparing subcutaneous adipose tissue in beef and muskox with emphasis on trans 18:1 and conjugated linoleic acids. Lipids, 42, 509-518 (2007).
  • Ecker,J., Scherer, M., Schmitz, G. and Liebisch, G. A rapid GC-MS method for quantification of positional and geometric isomers of fatty acid methyl esters. J. Chromatogr. B, 897, 98-104 (2012).
  • Einhorn,J., Virelizier,H., Gemal,A.L. and Tabet,J.C. Direct determination of double bond position in long chain conjugated dienes by t-butyl+ CI/mass spectrometry. Tetrahedron Letts, 26, 1445-1448 (1985).
  • El-Jaber,N., Estevez-Braun,A., Ravelo,A.G., Munoz-Munoz,O., Rodriguez-Afonso,A. and Murguia,J.R. Acetylenic acids from the aerial parts of Nanodea muscosa. J. Nat. Prod., 66, 722-724 (2003).
  • Emken,E.A., Scholfield,C.R., Davison,V.L. and Frankel,E.N. Separation of conjugated methyl octadecadienoate and trienoate geometric isomers by silver-resin column and preparative gas-liquid chromatography. J. Am. Oil Chem. Soc., 44, 373-375 (1967).
  • Erciyes,A.T. and Civelekoglu,H. On the argentation thin-layer chromatography of some conjugated trienoic acids. Bull. Tech. Univ. Istanbul, 36, 381-396 (1983).
  • Eulitz,K., Yurawecz,M.P., Sehat,N., Fritsche,J., Roach,J.A.G., Mossoba,M.M., Kramer,J.K.G., Adlof,R.O. and Ku,Y. Preparation, separation, and confirmation of the eight geometrical cis/trans conjugated linoleic acid isomers 8,10-through 11,13-18:2. Lipids, 34, 873-877 (1999).
  • Foglia,T.A., Conkerton,E.J. and Sonnet,P.E. Regioselective analysis of triacylglycerols by lipase hydrolysis. J. Am. Oil Chem. Soc., 72, 1275-1279 (1995).
  • Fritsche,J., Fritsche,S., Solomon,M.B., Mossoba,M.M., Yurawecz,M.P., Morehouse,K. and Ku,Y. Quantitative determination of conjugated linoleic acid isomers in beef fat. Eur. J. Lipid Sci. Technol., 102, 667-672 (2000).
  • Fritsche,J., Mossoba,M.M., Yurawecz,M.P., Roach,J.A.G., Sehat,N., Ku,Y. and Steinhart,H. Conjugated linoleic acid (CLA) isomers in human adipose tissue. Z. Lebensm.-Unters. Forsch., 205, 415-418 (1997).
  • Fritsche,J., Rickert,R., Steinhart,H., Yurawecz,M.P., Mossoba,M.M., Sehat,N., Roach,J.A.G., Kramer,J.K.G. and Ku,Y. Conjugated linoleic acid (CLA) isomers: formation, analysis, amounts in foods, and dietary intake. Fett-Lipid, 101, 272-276 (1999).
  • Fu,W.C., Gu,X.H., Tao,G.J., Tang,J. and Jiang,Z.L. Structure identification of triacylglycerols in the seed oil of Momordica charantia L. var. abbreviata Ser. J. Am. Oil Chem. Soc., 86, 33-39 (2009).
  • Gaydou,E.M., Miralles,J. and Rasoazanakolona,V. Analysis of conjugated octadecatrienoic acids in Momordica balsaminaseed oil by gas-liquid chromatography and 13C NMR spectroscopy. J. Am. Oil Chem. Soc., 64, 997-1000 (1987).
  • Geiger,O., Glushka,J., Lugtenberg, B.J.J., Spaink,H.P. and Thomas-Oates,J.E. NodFE-Dependent fatty acids that lack an alpha-beta-unsaturation are subject to differential transfer, leading to novel phospholipids. Mol. Plant-Microbe Interactions, 11, 33-44 (1998).
  • Gómez-Cortés,P., Tyburczy,C., Brenna,J.T., Juárez,M. and Angel de la Fuente,M. 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 (2009).
  • Gorissen,L., Raes,K., Weckx,S., Dannenberger,D., Leroy,F., De Vuyst,L. and De Smet,S. Production of conjugated linoleic acid and conjugated linolenic acid isomers by Bifidobacterium species. Appl. Microbiol. Biotechnol., 87, 2257-2266 (2010).
  • Gunstone,F.D. and Subbarao,R. New tropical seed oils 1. Conjugated trienoic and tetraenoic acids and their oxo derivatives in the seed oils of Chrysobalanus icaco and Parinarium laurinum. Chem. Phys. Lipids, 1, 349-359 (1967).
  • Hamalainen,T.I., Sundberg,S., Hase,T. and Hopia,A. Stereochemistry of the hydroperoxides formed during autoxidation of CLA methyl ester in the presence of alpha-tocopherol. Lipids, 37, 533-540 (2002).
  • Hamberg,M. Oxidation of octadecatrienoic acids in the red alga Lithothamnion corallioides: structural and stereochemical studies of conjugated tetraene fatty acids and bis-allylic hydroxy acids. J. Chem. Soc. Perkin Trans. I., 3065-3072 (1993).
  • Haque,M.E., Haque,M., Rahman,M.M., Rahman,M.M., Khondkar,P., Wahed,M.I.I., Mossadik,M.A., Gray,A.I. and Sarker,S.D. E-Octadec-7-en-5-ynoic acid from the roots of Capparis zeylanica. Fitoterapia, 75, 130-133 (2004).
  • Hasegawa,T., Ishibashi,M., Takata,T., Takano,F. and Ohta,T. Cytotoxic fatty acid from Pleurocybella porrigens. Chem. Pharm. Bull., 55, 1748-1749 (2007).
  • Hayes,D.G., Kleiman,R., Weisleder,D., Adlof,R.O., Cuperus,F.P. and Derksen,J.T.P. Occurrence of estolides in processed Dimorphotheca pluvialis seed oil. Ind. Crops Products, 4, 295-301 (1995).
  • Higashi,T., Takekawa, M., Min, J.Z. and Toyo'oka, T. Diels-Alder derivatization for sensitive detection and characterization of conjugated linoleic acids using LC/ESI-MS/MS. Anal. Bioanal. Chem., 403, 495-502 (2012).
  • Honkanen,A.M., Griinari, J.M., Vanhatalo, A., Ahvenjarvi, S., Toivonen, V. and Shingfield, K.J. Characterization of the disappearance and formation of biohydrogenation intermediates during incubations of linoleic acid with rumen fluid in vitro. J. Dairy Sci., 95, 1376-1394 (2012).
  • Horii,N., Arato,S., Narayan,B., Hosokawa,M., Sashima,T. and Miyashita,K. Occurrence of conjugated cyclopropanoid acid in purified fish oil. J. Am. Oil Chem. Soc., 84, 749-754 (2007).
  • Hurst,W.J., Tarka,S.M., Dobson,G. and Reid,C.M. Determination of conjugated linoleic acid (CLA) concentrations in milk chocolate J. Agric. Food Chem., 49, 1264-1265 (2001).
  • Husain,S. and Devi,K.S. Separation and identification of isomeric conjugated fatty acids by HPLC with photodiode array detection. Lipids, 28, 1037-1040 (1993).
  • Igarashi,M. and Miyazawa,T. Preparation and fractionation of conjugated trienes from alpha-linolenic acid and their growth-inhibitory effects on human tumor cells and fibroblasts. Lipids, 40, 109-113 (2005).
  • Igarashi,M., Tsuzuki,T., Kambe,T. and Miyazawa,T. Recommended methods of fatty acid methylester preparation for conjugated dienes and trienes in food and biological samples. J. Nutr. Sci. Vitam., 50, 121-128 (2004).
  • Ingram,C.D. and Brash,A.R. Characterisation of HETEs and related conjugated dienes by UV spectroscopy. Lipids, 23, 340-344 (1988).
  • Ismail,A.A., Nicodemo,A., Sedman,J., van de Voort,F.R. and Holzbaur,I.E. Infrared spectroscopy of lipids: principles and applications. In: 'Spectral Properties of Lipids', pp. 235-269 (edited by R.J. Hamilton & J. Cast, Sheffield Academic Press) (1998).
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Updated: August 13, 2013