Literature Survey

Stereospecific Analysis of Triacyl-sn-glycerols

 

Stereospecific analysis of triacyl-sn-glycerols, i.e. determination of the fatty acid compositions of positions sn-1, 2 and 3, is not the easiest of analytical tasks, but great strides have been made in recent years. You may find that our web-pages on triacylglycerols are a good introduction to the topic. Regiospecific analysis, i.e. differentiation of position 2 from the primary positions by lipase hydrolysis or NMR spectroscopy is not covered here.

The following references were collected as part of our regular literature reviews for our own research purposes, and cover the years 1965 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.

  • Agren,J.J. and Kuksis,A. Analysis of diastereomeric DAG naphthylethylurethanes by normal-phase HPLC with on-line electrospray MS. Lipids, 37, 613-619 (2002).
  • Agren,J.J., Ravandi,A., Kuksis,A. and Steiner,G. Structural and compositional changes in very low density lipoprotein triacylglycerols during basal lipolysis. Eur. J. Biochem., 269, 6223-6232 (2002).
  • Anderson, R.E., Bottino,N.R. and Reiser,R. Pancreatic lipase hydrolysis as a source of diglycerides for the stereospecific analysis of triglycerides. Lipids, 2, 440-442 (1967).
  • Ando,Y. and Kobayashi,S. Positional distribution of docosahexaenoic acid in triacyl-sn-glycerols of rotifers Brachionus plicatilis enriched with fish oil fatty acid ethyl esters. Aquaculture Res., 35, 1391-1394 (2004).
  • Ando,Y. and Oomi,Y. Positional distribution of highly unsaturated fatty acids in triacyl-sn-glycerols of Artemia nauplii enriched with docosahexaenoic acid ethyl ester. Lipids, 36, 733-740 (2001).
  • Ando,Y. and Takagi,T. Micro method for stereospecific analysis of triacyl-sn-glycerols by chiral-phase HPLC. J. Am. Oil Chem. Soc., 70, 1047-1049 (1993).
  • Ando,Y., Nishimura,K., Aoyanagi,N. and Takagi,T. Stereospecific analysis of fish oil triacyl-sn-glycerols. J. Am. Oil Chem. Soc., 69, 417-424 (1992).
  • Ando,Y., Ota,T., Matsuhira,Y. and Yazawa,K. Stereospecific analysis of triacyl-sn-glycerols in docosahexaenoic acid-rich fish oils. J. Am. Oil Chem. Soc., 73, 483-487 (1996).
  • Ando,Y., Satake,M. and Takahashi,Y. Reinvestigation of positional distribution of fatty acids in docosahexaenoic acid-rich fish oil triacyl-sn-glycerols. Lipids, 35, 579-582 (2000).
  • Ando,Y., Shimoyama,A. and Ota,T. Changes in positional distribution of fatty acids in dorsal muscle triacyl-sn-glycerols from chum salmon, Oncorhynchus keta, at spawning season. Comp. Biochem. Physiol. B, 113, 89-93 (1996).
  • Ando,Y., Tomita,Y. and Haba,Y. Preparation of ethyl magnesium bromide for regiospecific analysis of triacylglycerols. J. Oleo Sci., 57, 459-462 (2008).
  • Arunga, R.O. and Morrison,W.R. The structural analysis of wheat flour glycerolipids. Lipids, 6, 768-776 (1971).
  • Bezard, J., Ouedraogo,M.A. and Sempore,G. Stereospecific analysis of the palmito-oleo-linolein of cottonseed oil. Rev. Franc. Corps Gras, 37, 171-175 (1990).
  • Bezard, J., Ouedraogo,M.A., Sempore,G. and Schreiber,L. Study of the stereospecific distribution of fatty acids in the triglycerides of cottonseed oil. Rev. Franc. Corps Gras, 37, 83-90 (1990).
  • Bezard, J.A. and Sempore,B.G. Structural analysis of peanut oil triacylglycerols. in New Trends in Lipid and Lipoprotein Analyses, pp. 106-132 (ed. J.-L. Sebedio and E.G. Perkins, AOCS Press, Champaign, USA) (1995).
  • Blasi, F., Lombardi, G., Damiani, P., Simonetti, M.S., Giua, L. and Cossignani, L. Triacylglycerol stereospecific analysis and linear discriminant analysis for milk speciation. J. Dairy Res., 80, 144-151 (2013).
  • Blasi, F., Montesano,D., De Angelis,M., Maurizi,A., Ventura,F., Cossignani,L., Simonetti,M.S. and Damiani,P. Results of stereospecific analysis of triacylglycerol fraction from donkey, cow, ewe, goat and buffalo milk. J. Food Comp. Anal., 21, 1-7 (2008).
  • Boukhchina, S., Gresti,J., Kallel,H. and Bezard,J. Stereospecific analysis of TAG from sunflower seed oil. J. Am. Oil Chem. Soc., 80, 5-8 (2003).
  • Breckenridge, W.C. Stereospecific analysis of triacylglycerols. in 'Handbook of Lipid Research. Vol. 1. Fatty Acids and Glycerides', pp. 197-232 (edited by A. Kuksis, Plenum Press, New York) (1978).
  • Breckenridge, W.C. and Kuksis,A. Specific distribution of short-chain fatty acids in molecular distillates of bovine milk fat. J. Lipid Res., 9, 388-393 (1968).
  • Breckenridge, W.C. and Kuksis,A. Structure of bovine milk fat triglycerides. I. Short and medium chain lengths. Lipids, 3, 291-300 (1968).
  • Breckenridge, W.C. and Kuksis,A. Structure of bovine milk fat triglycerides: II. Long chain lengths. Lipids, 4, 197-204 (1969).
  • Breckenridge, W.C. and Kuksis,A. Stereochemical course of diacylglycerol formation in rat intestine. Lipids, 7, 256-259 (1972).
  • Brockerhoff,H. A stereospecific analysis of triglycerides. J. Lipid Res., 6, 10-15 (1965).
  • Brockerhoff,H. An unsolved problem of triglyceride analysis. Lipids, 1, 162 (1966).
  • Brockerhoff,H. Stereospecific analysis of triglycerides: an alternative method. J. Lipid Res., 8, 167-169 (1967).
  • Brockerhoff,H. Stereospecific analysis of triglycerides. Lipids, 6, 942-956 (1971).
  • Brockerhoff,H. Determination of fatty acids in position sn-3 of triglycerides. Lipids, 8, 439 (1973).
  • Brockerhoff,H. and Ackman,R.G., Positional distribution of isomers of monoenoic fatty acids in animal glycerolipids. J. Lipid Res., 8, 661-666 (1967).
  • Brockerhoff,H. and Yurkowski,M. Stereospecific analysis of several vegetable fats. J. Lipid Res., 7, 62-64 (1966).
  • Brockerhoff,H., Hoyle,R.J. and Wolmark,N. Positional distribution of fatty acids in triglycerides of animal depot fats. Biochim. Biophys. Acta, 116, 67-72 (1966).
  • Brockerhoff,H., Hoyle,R.J., Hwang,P.C. and Litchfeld,C. Positional distribution of fatty acids in depot triglycerides of aquatic animals. Lipids, 3, 24-29 (1968).
  • Carriere, F., Rogalska,E., Cudrey,C., Ferrato,F., Laugier,R. and Verger,R. In vivo and in vitro studies on the stereoselective hydrolysis of tri- and diglycerides by gastric and pancreatic lipases. Bioorg. Med. Chem., 5, 429-435 (1997).
  • Chandler, I.C., Quinlan,P.T. and McNeill,G.P. Lipase-catalyzed synthesis of chiral triglycerides. J. Am. Oil Chem. Soc., 75, 1513-1518 (1998).
  • Christie, W.W. The glyceride structure of Sapium sebiferum seed oil. Biochim. Biophys. Acta, 187, 1-5 (1969).
  • Christie, W.W. Biosynthesis of triglycerides in freshly secreted milk from goats. Lipids, 9, 876-882 (1974).
  • Christie, W.W. Structural analysis of triglycerides containing isotopically-labelled fatty acids. J. Chromatogr. Sci., 13, 411-415 (1975).
  • Christie, W.W. The positional distribution of fatty acids in triglycerides. in 'Analysis of Oils and Fats', pp. 313-339 (ed R.J. Hamilton & J.B.Rossell, Elsevier Applied Science, London) (1986).
  • Christie, W.W. Methods for stereospecific analysis of triacyl-sn-glycerols in 'Contemporary Lipid Analysis, 2nd Symposium Proceedings', pp. 63-71 (edited by N.U. Olsson & B.G. Herslof, LipidTeknik, Stockholm) (1992).
  • Christie, W.W. Silver ion and chiral chromatography in the analysis of triacylglycerols. Prog. Lipid Res., 33, 9-18 (1994).
  • Christie, W.W. and Clapperton,J.L. Structures of the triacylglycerols of human milk and some substitutes. J. Soc. Dairy Technol., 35, 22-24 (1982).
  • 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. and Hunter,M.L. Stereospecific analysis of triacylglycerols that contain isotopically labelled fatty acids. Biochim. Biophys. Acta, 316, 282-287 (1973).
  • Christie, W.W. and Hunter,M.L. The composition and structure of the lipids of sheep lymph. J. Sci. Food Agric., 29, 442-446 (1978).
  • Christie, W.W. and Hunter,M.L. Stereospecific distribution of palmitic acid in the triacylglycerols of rat adipocytes. Effects of varying the composition of the substrate fatty acids in vitro. Biochem. J., 191, 637-643 (1980).
  • Christie, W.W. and Hunter,M.L. Metabolism of the diacetyl derivatives of stereoisomeric monoacyl-sn-glycerols by rat adipocytes in vitro. Biochem. J., 235, 833-838 (1986).
  • Christie, W.W. and Moore,J.H. A semimicro method for the stereospecific analysis of triglycerides. Biochim. Biophys. Acta, 176, 445-452 (1969).
  • Christie, W.W. and Moore,J.H. The effect of dietary copper on the structure and physical properties of adipose tissue triglycerides in pigs. Lipids, 4, 345-349 (1969).
  • Christie, W.W. and Moore,J.H. The structures of egg yolk triglycerides. Biochim. Biophys. Acta, 218, 83-88 (1970).
  • Christie, W.W. and Moore,J.H. The variation of triglyceride structure with fatty acid composition in pig adipose tissue. Lipids, 5, 921-928 (1970).
  • Christie, W.W. and Moore,J.H. A comparison of the structures of triglycerides from various pig tissues. Biochim. Biophys. Acta, 210, 46-56 (1970).
  • Christie, W.W. and Moore,J.H. Structures of triglycerides isolated from various sheep tissues. J. Sci. Food Agric., 22, 120-124 (1971).
  • Christie, W.W. and Moore,J.H. The lipid composition and triglyceride structure of eggs from several avian species. Comp. Biochem. Physiol., 41B, 297-306 (1972).
  • Christie, W.W. and Moore,J.H. The structures of adipose tissue and heart muscle triglycerides in the domestic chicken (Gallus gallus). J. Sci. Food Agric., 23, 73-77 (1972).
  • Christie, W.W. and Noble,R.C. The lipid composition of the spleen and intestinal and popliteal lymph nodes in the sheep. Lipids, 20, 389-392 (1985).
  • Christie, W.W. and Vernon,R.G. The positional distribution of fatty acids incorporated into triacylglycerols by rat adipose tissue slices in vitro. Biochem. Biophys. Res. Commun., 66, 243-249 (1975).
  • Christie, W.W., Clegg,R.A., Calvert,D.T. and Noble,R.C. The positional distributions of fatty acids in the triacylglycerols and phosphatidylcholines of the intestinal and popliteal lymph and plasma of sheep. Lipids, 19, 982-986 (1984).
  • Christie, W.W., Hunter,M.L. and Moore,J.H. The structure of the plasma triglycerides from lactating cows. N. Z. J. Dairy Sci. Technol., 13, 119-120 (1978).
  • Christie, W.W., Hunter,M.L. and Vernon,R.G. Triacylglycerol biosynthesis in rat adipose-tissue homogenates. Biochem J., 159, 571-577 (1976).
  • Christie, W.W., Moore,J.H. and Gottenbos,J.J. Effect of dietary saturated fatty acids and linoleic acid upon the structures of triglycerides in rabbit tissues. Lipids, 9, 201-207 (1974).
  • Christie, W.W., Moore,J.H., Lorimer,A.R. and Lawrie,T.D.V. The structures of triglycerides from atherosclerotic plaques and other human tissues. Lipids, 6, 854-856 (1971).
  • Christie, W.W., Nikolova-Damyanova,B., Laakso,P. and Herslof,B. Stereospecific analysis of triacyl-sn-glycerols via resolution of diastereomeric diacylglycerol derivatives by HPLC on silica. J. Am. Oil Chem. Soc., 68, 695-701 (1991).
  • Cossignani, L., Blasi,F., Bosi,A., D'Arco,G., Maurelli,S., Simonetti,M.S. and Damiani,P. Detection of cow milk in donkey milk by chemometric procedures on triacylglycerol stereospecific analysis results. J. Dairy Res., 78, 335-342 (2011).
  • Cossignani, L., Damiani,E., Gabrielli,L., Montesano,D., Simonetti,M.S., Petrosino,T., Ventura,E., Marini,E. and Damiani,P. Structural characteristics of the triacylglycerol fraction from the seed fat of Mangifera indica L. Ital. J. Food Sci., 20, 263-271 (2008).
  • Cossignani, L., Luneia,R., Damiani,P., Simonetti,M.S., Riccieri,R. and Tiscornia,E. Analysis of isomeric diacylglycerolic classes to evaluate the quality of olive oil in relation to storage conditions. Eur. Food Res. Technol., 224, 379-383 (2007).
  • Cossignani, L., Simonetti,M.S., Neri,A. and Damiani,P. Structural analysis of triacylglycerol fraction and some of its sub-fractions from an eicosapentaenoic acid docosahexaenoic acid dietary supplement. Z. Lebensm.-Unters. Forsch., 208, 203-207 (1999).
  • Damiani,P., Cossignani,L., Simonetti,M.S., Campisi,B., Favretto,L. and Favretto,L.G. Stereospecific analysis of the triacylglycerol fraction and linear discriminant analysis in a climatic differentiation of Umbrian extra-virgin olive oils. J. Chromatogr. A, 758, 109-116 (1997).
  • Damiani,P., Cossignani,L., Simonetti,M.S., Santinelli,F. and Monotti,M. Stereospecific analysis of triacylglycerols from vegetable oils by two procedures.2. Normal and high-oleic sunflower oils. J. Am. Oil Chem. Soc., 74, 927-933 (1997).
  • Damiani,P., Cossignani,L., Simonetti,M.S., Blasi,F., Petrosino,T. and Neri,A. Identification of cocoa butter equivalents added to cocoa butter. III. Stereospecific analysis of triacylglycerol fraction and some its subfraction. Eur. Food Res. Technol., 223, 645-648 (2006).
  • Damiani,P., Rosi,M., Castellini,M., Santinelli,F., Cossignani,L. and Simonetti,M.S. Stereospecific analysis of triacylglycerols by an enzymic procedure using a new sn-1,2-diacylglycerol kinase preparation - application to olive and sunflower oils. Ital. J. Food Sci., 6, 113-122 (1994).
  • Damiani,P., Santinelli,F., Simonetti,M.S., Castellini,M. and Rosi,M. Comparison between two procedures for stereospecific analysis of triacylglycerols from vegetable oils. 1. Olive oil. J. Am. Oil Chem. Soc., 71, 1157-1162 (1994).
  • De La Roche,I.A., Weber,E.J. and Alexander,D.E. Effects of fatty acid concentration and positional specificity on maize triglyceride structure. Lipids, 6, 531-536 (1971).
  • De La Roche,I.A., Weber,E.J. and Alexander,D.E. The selective utilization of diglyceride species into maize triglycerides. Lipids, 6, 537-540 (1971).
  • Fatemi,S.H. and Hammond,E.G. Glyceride structure variation in soybean varieties. I. Stereospecific analysis. Lipids, 12, 1032-1036 (1977).
  • Hadley,N.F. and Christie,W.W. The lipid composition and triglyceride structure of eggs and fat bodies of the lizard Sceloporus jarrovi. Comp. Biochem. Physiol., 48B, 275-284 (1974).
  • Haley,J.E. and Jack,R.C. Stereospecific analysis of triacylglycerols and major phosphoglycerides from Lipomyces lipoferus. Lipids, 9, 679-681 (1974).
  • Hammond,E.G. The resolution of complex triglyceride mixtures. Lipids, 4, 246-249 (1969).
  • Harp,T.K. and Hammond,E.G. Stereospecific analysis of soybean triacylglycerols. Lipids, 33, 209-216 (1998).
  • Henderson,R.J., Christie,W.W. and Moore,J.H. Positional distribution of exogenous and endogenous fatty acids in triacylglycerols formed by rat adipocytes in vitro. Biochim. Biophys. Acta, 574, 8-17 (1979).
  • Hunter,M.L., Christie,W.W. and Moore,J.H, The structures of the principal glycerolipids of pig liver. Lipids, 8, 65-70 (1973).
  • Itabashi,Y. Chiral-phase HPLC resolution of enantiomeric diacylglycerol moieties of fish-oil triacylglycerols. Bunseki Kagaku, 48, 1145-1148 (1999).
  • Itabashi,Y., Myher,J.J. and Kuksis,A. Determination of positional distribution of short-chain fatty acids in bovine milk fat on chiral columns. J. Am. Oil Chem. Soc., 70, 1177-1181 (1993).
  • Itabashi,Y., Kuksis,A., Marai,L. and Takagi,T. HPLC resolution of diacylglycerol moieties of natural triacylglycerols on a chiral phase consisting of bonded R-(+)-1-(1-naphthyl)-ethylamine. J. Lipid Res., 31, 1711-1717 (1990).
  • Jensen, R.G., Sampugna,J. and Quinn,J.G. Comments on the analysis of some triacid triglyceride mixtures. Lipids, 1, 294-295 (1966).
  • Kim,M., No,S. and Yoon,S.H. Stereospecific analysis of fatty acid composition of chufa (Cyperus esculentus L.) tuber oil. J. Am. Oil Chem. Soc., 84, 1079-1080 (2007).
  • Kuksis,A. Acylglycerols (glycerides). in 'Handbook of Chromatography. Vol. I. Lipids', pp. 381-480 (edited by H.K.Mangold, CRC Press, Boca Raton) (1984).
  • Kuksis,A. Analysis of positional isomers of glycerolipids by non-enzymatic methods. In Advances in Lipid Methodology - Three, pp. 1-36 (ed. W. Christie, Oily Press, Dundee) (1996).
  • Kuksis,A. and Itabashi,Y. LC/MS and chiral separation. In: Lipid Analysis and Lipidomics: New Techniques and Applications. pp. 73-108 (ed: M.M. Mossoba, J.K.G. Kramer, J.T. Brenna and R.E. McDonald, AOCS Press, Champaign, USA) (2006).
  • Kuksis,A. and Itabashi,Y. Regio- and stereospecific analysis of glycerolipids. Methods, 36, 172-185 (2005).
  • Kuksis,A., Myher,J.J. and Marai,L. Lipid methodology - chromatography and beyond. II. GC/MS, LC-MS and specific enzymic hydrolysis of glycerolipids. J. Am. Oil Chem. Soc., 62, 762-767 (1985).
  • Kuksis,A., Myher,J.J. and Marai,L. Lipid methodology - chromatography and beyond. III. Analyses of natural and 2H-labelled glycerolipids by GC/MS and LC/MS with specific enzymic hydrolyses. J. Am. Oil Chem. Soc., 62, 767-773 (1985).
  • Lands, W.E.M. and Slakey,P.M. A solved problem of triglyceride analysis. Lipids, 1, 295 (1966).
  • Lands, W.E.M., Pieringer,R.A., Slakey,P.M. and Zschoche,A. A micromethod for the stereospecific determination of triglyceride structure. Lipids, 1, 444-448 (1963).
  • Lawson, L.D., and Hughes,B.G. Triacylglycerol structure of plant and fungal oils containing gamma-linolenic acid. Lipids, 23, 313-317 (1988).
  • Lisa, M. and Holcapek, M. Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols. Anal. Chem., 85, 1852-1859 (2013).
  • Manganaro, F., Myher,J.J., Kuksis,A. and Kritchevsky,D. Acylstructure of genetic varieties of peanut oils of varying atherogenic potential. Lipids, 16, 508-517 (1981).
  • Marai, L., Breckenridge,W.C. and Kuksis,A. Specific distribution of fatty acids in the milk fat triglycerides of goat and sheep. Lipids, 4, 562-570 (1969).
  • Martin, J.-C., Bougnoux,P., Antoine,J.-M., Lanson,M. and Couet,C. Triacylglycerol structure of human colostrum and mature milk. Lipids, 28, 637-643 (1993).
  • Martinez-Force, E., Ruiz-Lopez,N. and Garces,R. The determination of the asymmetrical stereochemical distribution of fatty acids in triacylglycerols. Anal. Biochem., 334, 175-182 (2004).
  • Maurin,R., Fellat-Zarrouck,K. and Ksir,M. Positional analysis and determination of triacylglycerol structure of Argania spinosa seed oil. J. Am. Oil Chem. Soc., 69, 141-145 (1992).
  • Morley, N.H., Kuksis, A. and Buchnea, D. Hydrolysis of synthetic triacylglycerols by pancreatic and lipoprotein lipase. Lipids, 9, 481-488 (1974).
  • Morrison, I.M. and Hawke,J.C. Positional distribution of fatty acids in the triglycerides of bovine milk fat with elevated levels of linoleic acid. Lipids, 12, 1005-1011 (1977).
  • Myher, J.J. and Kuksis,A. Stereospecific analysis of TG via racemic phosphatidylcholines and phospholipase C. Can. J. Biochem., 57, 117-124 (1979).
  • Myher, J.J., Kuksis,A., Breckenridge,W.C. and Little,J.A. Studies of triacylglycerol structure of very low density lipoproteins of normolipemic subjects and patients with type III and type IV hyperlipoproteinemia. Lipids, 19, 683-691 (1984).
  • Myher, J.J., Kuksis,A., Breckenridge,W.C., McGuire,V. and Little,J.A. Comparative studies of triacylglycerol structure of VLDL lipopoproteins and chylomicrons of normolipemic subjects with Type II hyperlipoproteinemia. Lipids, 20, 90-101 (1985).
  • Myher, J.J., Kuksis,A., Marai,L. and Cerbulis,J. Stereospecific analysis of FA esters of chloropropanediol isolated from fresh goat milk. Lipids, 21, 309-314 (1986).
  • Myher, J.J., Kuksis,A. and Steiner,G. Milk fat structure of a patient with type 1 hyperlipidemia. Lipids, 19, 673-682 (1984).
  • Myher, J.J., Kuksis,A. and Park,P.W. Stereospecific analysis of docosahexaenoic acid-rich triacylglycerols by chiral-phase HPLC with online electrospray mass spectrometry. in 'New Techniques and Applications in Lipid Analysis', pp. 100-120 (edited by R.E. McDonald and M.M. Mossoba, AOCS Press, Champaign) (1998).
  • Myher, J.J., Kuksis,A., Yang,L-Y. and Marai,L. Stereochemical course of intestinal absorption and transport of mustardseed triacylglycerols in the rat. Biochem. Cell Biol., 65, 811-821 (1987).
  • Myher, J.J., Marai, L., Kuksis,A. and Kritchevsky,D. Acylglycerol structure of peanut oils of different atherogenic potential. Lipids, 12, 775-785 (1977).
  • Nagai, T., Matsumoto, Y., Jiang, Y.Y., Ishikawa, K., Wakatabe, T., Mizobe, H., Yoshinaga, K., Kojima, K., Kuroda, I., Saito, T., Beppu, F. and Gotoh, N. Actual ratios of triacylglycerol positional isomers and enantiomers comprising saturated fatty acids and highly unsaturated fatty acids in fishes and marine mammals. J. Oleo Sci., 62, 1009-1015 (2013).
  • Ohlson, R., Podlaha,O. and Toregard,B. Stereospecific analysis of some Cruciferae species. Lipids, 10, 734-735 (1975).
  • Pan, W.P. and Hammond,E.G. Stereospecific analysis of TG of Glycine max, Glycine soya, Avena sativa and Avena sterilis strains. Lipids, 18, 882-888 (1983).
  • Parijs, J., De Weerdt,G.A., Beke,R. and Barbier,F. Stereospecific analysis of human plasma triglycerides. Lipids, 9, 937-938 (1974).
  • Parodi, P.W. Positional distribution of fatty acids in triglycerides from milk of several species of mammals. Lipids, 17, 437-442 (1982).
  • Parodi, P.W. and Griffiths,M. A comparison of the positional distribution of fatty acids in milk triglycerides of the extant monotremes platypus (Ornithorhynchus anatinus) and echidna (Tachyglossus aculeatus). Lipids, 18, 845-847 (1983).
  • Petrosino,T., Riccieri,R., Blasi,F., Brutti,M., D'arco,G., Bosi,A., Maurelli,S., Cossignani,L., Simonetti,M.S. and Damiani,P. Original normal-phase high-performance liquid chromatographic separation of monoacylglycerol classes from extra virgin olive oil triacylglycerols for their stereospecific analysis. J. AOAC Int., 90, 1647-1654 (2007).
  • Pfeffer,P.E., Sampugna,J., Schwartz,D.P. and Shoolery,J.N. Analytical 13C NMR: detection, quantitation and positional analysis of butyrate in butter oil. Lipids, 12, 869-871 (1977).
  • Pham,L.J. and Gregorio,M.A The triacylglycerol structure of coconut oil determined by chromatography combined with stereospecific analysis. Philippine Agricultural Scientist, 91, 343-347 (2008).
  • Phillips,B.E., Smith,C.R. and Tallent,W.H. Glycerides of Limnanthes douglasii seed oil. Lipids, 6, 93-99 (1971).
  • Phornpiboonya,Y. and Jack,R.C. Changes in stereospecific distribution of yeast fatty acids with age. Chem. Phys. Lipids, 26, 57-66 (1980).
  • Piyatheerawong,W., Iwasaki,Y. and Yamane,T. Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography. J. Chromatogr. A, 1068, 243-248 (2005).
  • Raclot,T., Groscolas,R. and Leray,C. Composition and structure of triacylglycerols in brown adipose tissue of rats fed fish oil. Lipids, 29, 759-764 (1994).
  • Raclot,T., Leray,C., Bach,A.C. and Groscolas,R. The selective mobilization of fatty acids is not based on their positional distribution in white-fat-cell triacylglycerols. Biochem. J., 311, 911-916 (1995).
  • Redden,P.R., Lin,X.R., Fahey,J. and Horrobin,D.F. Stereospecific analysis of the major triacylglycerol species containing gamma-linolenic acid in evening primrose oil and borage oil. J. Chromatogr. A, 704, 99-111 (1995).
  • Reske,J., Siebrecht,J. and Hazebroek,J. Triacylglycerol composition and structure in genetically modified sunflower and soybean oils. J. Am. Oil Chem. Soc., 74, 989-998 (1997).
  • Rodriguez,J.A., Ben Ali,Y., Abdelkafi,S., Mendoza,L.D., Leclaire,J., Fotiadu,F., Buono,G., Carriere,F. and Abousalham,A. In vitro stereoselective hydrolysis of diacylglycerols by hormone-sensitive lipase. Biochim. Biophys. Acta, 1801, 77-83 (2010).
  • Rogalska,E., Cudrey,C., Ferrato,F. and Verger,R. Stereoselective hydrolysis of triglycerides by animal and microbial lipases. Chirality, 5, 24-30 (1993).
  • Rogalska,E., Ransac,S. and Verger,R. Stereoselectivity of lipases. II. Stereoselective hydrolysis of triglycerides by gastric and pancreatic lipases. J. Biol. Chem., 265, 20271-20276 (1990).
  • Rosati,O., Albrizio,S., Montesano,D., Riccieri,R., Cossignani,L., Curini,M., Simonetti,M.S., Rastrelli,L. and Damiani,P. HPLC separation and NMR structural elucidation of sn-1,2-, 2,3-, and 1,3-diacylglycerols from olive oil as naphthylethylurethane derivatives. J. Agric. Food Chem., 55, 191-196 (2007).
  • Sampugna,J. and Jensen,R.G. Stereospecific analysis of the major triglyceride species in the monounsaturated fraction of cocoa butter. Lipids, 4, 444-449 (1969).
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 Updated: February 5, 2014