Regioisomeric and enantiomeric analysis of triacylglycerols

Analytical Biochemistry

Volumn 524, Issue , 2017, Pages 3-12

  Řezanka, Tomáš ^a   Pádrová, Karolína ^b   Sigler, Karel ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Atmospheric pressure chemical ionization; Enantiomers; High performance liquid chromatography; Regioisomers; Triacylglycerols

Indexed keywords

SILVER; TRIACYLGLYCEROL;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRAL CHROMATOGRAPHY; ENANTIOMER; ENZYME CHEMISTRY; IONIZATION; ISOMERISM; LIPID ANALYSIS; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; REGIOISOMER; REVERSED PHASE LIQUID CHROMATOGRAPHY; STEREOSPECIFICITY; SUPERCRITICAL FLUID CHROMATOGRAPHY; CHEMISTRY; PROCEDURES;

GAS CHROMATOGRAPHY-MASS SPECTROMETRY; SILVER; TRIGLYCERIDES;

EID: 84979704129     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2016.05.028     Document Type: Article

References (72)

1. [1] Hu, J., Wei, F., Dong, X.Y., Lv, X., Jiang, M.L., Li, G.M., Chen, H., Characterization and quantification of triacylglycerols in peanut oil by off-line comprehensive two-dimensional liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry. J. Sep. Sci. 36 (2013), 288–300.
2. [2] Stamatov, S.D., Stawinski, J., Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides. Org. Biomol. Chem. 5 (2007), 3787–3800.
3. [3] Lísa, M., Velínská, H., Holčapek, M., Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards. Anal. Chem. 81 (2009), 3903–3910.
4. [4] Marangoni, A.G., Fat Crystal Networks. 2004, CRC Press, Boca Raton, FL, USA ISBN 9781420030549.
5. [5] Řezanka, T., Mareš, P., Determination of plant triacylglycerols using capillary gas-chromatography, high-performance liquid-chromatography and mass-spectrometry. J. Chromatogr. 542 (1991), 145–159.
6. [6] Kemppinen, A., Kalo, P., Analysis of sn-1(3)- and sn-2-short-chain acyl isomers of triacylglycerols in butteroil by gas-liquid chromatography. J. Am. Oil Chem. Soc. 75 (1998), 91–100.
7. [7] Mareš, P., High-temperature capillary gas-liquid chromatography of triacylglycerols and other intact lipids. Progr. Lip. Res. 27 (1988), 107–133.
8. [8] Blaise, P., Wolff, R., Farines, M., Regiospecific study of vegetable oil triacylglycerols by chemical cleavage and high-resolution NMR C-13, OCL-Ol. Corps Gras Li 4 (1997), 135–141.
9. [9] Mori, K., Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides. Tetrahedron 68 (2012), 8441–8449.
10. [10] Zhou, Q., Gao, B., Zhang, X., Xu, Y., Shi, H., Yu, L.L., Chemical profiling of triacylglycerols and diacylglycerols in cow milk fat by ultra-performance convergence chromatography combined with a quadrupole time-of-flight mass spectrometry. Food Chem. 143 (2014), 199–204.
11. [11] Lee, J.W., Uchikata, T., Matsubara, A., Nakamura, T., Fukusaki, E., Bamba, T., Application of supercritical fluid chromatography/mass spectrometry to lipid profiling of soybean. J. Biosci. Bioeng. 113 (2012), 262–268.
12. [12] Sandra, P., Medvedovici, A., Zhao, Y., David, F., Characterization of triglycerides in vegetable oils by silver-ion packed-column supercritical fluid chromatography coupled to mass spectroscopy with atmospheric pressure chemical ionization and coordination ion spray. J. Chromatogr. A 974 (2002), 231–241.
13. [13] Lee, J.W., Nagai, T., Gotoh, N., Fukusaki, E., Bamba, T., Profiling of regioisomeric triacylglycerols in edible oils by supercritical fluid chromatography/tandem mass spectrometry. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 966 (2014), 193–199.
14. [14] Christie, W.W., A stable silver-loaded column for the separation of lipids by high-performance liquid-chromatography. J. High. Resolut. Chrom. Chrom. Comm. 10 (1987), 148–150.
15. [15] Nikolova-Damyanova, B., Retention of lipids in silver ion high-performance liquid chromatography: facts and assumptions. J. Chromatogr. A 1216 (2009), 1815–1824.
16. [16] Lísa, M., Holčapek, M., Boháč, M., Statistical evaluation of triacylglycerol composition in plant oils based on high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry data. J. Agric. Food Chem. 57 (2009), 6888–6898.
17. [17] Holčapek, M., Dvořáková, H., Lísa, M., Girón, A.J., Sandra, P., Cvačka, J., Regioisomeric analysis of triacylglycerols using silver-ion liquid chromatography-atmospheric pressure chemical ionization mass spectrometry: comparison of five different mass analyzers. J. Chromatogr. A 1217 (2010), 8186–8194.
18. [18] Laakso, P., Christie, W.W., Pettersen, J., Analysis of North Atlantic and Baltic fish oil triacylglycerols by high-performance liquid chromatography with a silver ion column. Lipids 25 (1990), 284–291.
19. [19] Christie, W., Separation of molecular species of triacylglycerols by high-performance liquid chromatography with a silver ion column. J. Chromatogr. A 454 (1988), 273–284.
20. [20] Beccaria, M., Costa, R., Sullini, G., Grasso, E., Cacciola, F., Dugo, P., Mondello, L., Determination of the triacylglycerol fraction in fish oil by comprehensive liquid chromatography techniques with the support of gas chromatography and mass spectrometry data. Anal. Bioanal. Chem. 407 (2015), 5211–5225.
21. [21] Laakso, P., Voutilainen, P., Analysis of triacylglycerols by silver-ion high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Lipids 31 (1996), 1311–1322.
22. [22] Schuyl, P.J.W., de Joode, T., Vasconcellos, M.A., Duchateau, G.S.M.J.E., Silver-phase high-performance liquid chromatography electrospray mass spectrometry of triacylglycerols. J. Chromatogr. A 810 (1998), 53–61.
23. [23] Dugo, P., Favoino, O., Tranchida, P.Q., Dugo, G., Mondello, L., Off-line coupling of non-aqueous reversed-phase and silver ion high-performance liquid chromatography–mass spectrometry for the characterization of rice oil triacylglycerol positional isomers. J. Chromatogr. A 1041 (2004), 135–142.
24. [24] Leskinen, H., Suomela, J.-P., Pinta, J., Kallio, H., Regioisomeric structure determination of α-and γ-linolenoyldilinoleoylglycerol in blackcurrant seed oil by silver ion high-performance liquid chromatography and mass spectrometry. Anal. Chem. 80 (2008), 5788–5793.
25. [25] Holčapek, M., Velínská, H., Lísa, M., Česla, P., Orthogonality of silver-ion and non-aqueous reversed-phase HPLC/MS in the analysis of complex natural mixtures of triacylglycerols. J. Sep. Sci. 32 (2009), 3672–3680.
26. [26] Adlof, R.O., List, G.R., Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols. J. Agric. Food Chem. 51 (2003), 2096–2099.
27. [27] Francois, I., Pereira Ados, S., Sandra, P., Considerations on comprehensive and off-line supercritical fluid chromatography x reversed-phase liquid chromatography for the analysis of triacylglycerols in fish oil. J. Sep. Sci. 33 (2010), 1504–1512.
28. [28] Fardin-Kia, A.R., Delmonte, P., Kramer, J.K.G., Jahreis, G., Kuhnt, K., Santercole, V., Rader, J.I., Separation of the fatty acids in menhaden oil as methyl esters with a highly polar ionic liquid gas chromatographic column and identification by time of flight mass spectrometry. Lipids 48 (2013), 1279–1295.
29. [29] Řezanka, T., Nedbalová, L., Procházková, L., Sigler, K., Lipidomic profiling of snow algae by ESI-MS and silver-LC/APCI-MS. Phytochemistry 100 (2014), 34–42.
30. [30] Schreiberová, O., Krulikovská, T., Sigler, K., Čejková, A., Řezanka, T., RP-HPLC/MS-APCI analysis of branched chain TAG prepared by precursor-directed biosynthesis with Rhodococcus erythropolis. Lipids 45 (2010), 743–756.
31. [31] Lísa, M., Holčapek, M., Sovová, H., Comparison of various types of stationary phases in non-aqueous reversed-phase high-performance liquid chromatography-mass spectrometry of glycerolipids in blackcurrant oil and its enzymatic hydrolysis mixture. J. Chromatogr. A 1216 (2009), 8371–8378.
32. [32] Momchilova, S., Tsuji, K., Itabashi, Y., Nikolova-Damyanova, B., Kuksis, A., Resolution of triacylglycerol positional isomers by reversed-phase high-performance liquid chromatography. J. Sep. Sci. 27 (2004), 1033–1036.
33. [33] Kalo, P., Kemppinen, A., Kilpelainen, I., Determination of positional distribution of butyryl groups in milkfat triacylglycerols, triacylglycerol mixtures, and isolated positional isomers of triacylglycerols by gas chromatography and H-1 nuclear magnetic resonance spectroscopy. Lipids 31 (1996), 331–336.
34. [34] Kalo, P., Kemppinen, A., Ollilainen, V., Kuksis, A., Analysis of regioisomers of short-chain triacylglycerols by normal phase liquid chromatography-electrospray tandem mass spectrometry. Int. J. Mass Spectrom. 229 (2003), 167–180.
35. [35] Kalo, P., Kemppinen, A., Ollilainen, V., Kuksis, A., Regiospecific determination of short-chain triacylglycerols in butterfat by normal-phase HPLC with on-line electrospray-tandem mass spectrometry. Lipids 39 (2004), 915–928.
36. [36] Kalo, P., Kemppinen, A., Ollilainen, V., Determination of triacylglycerols in butterfat by normal-phase HPLC and electrospray-tandem mass spectrometry. Lipids 44 (2009), 169–195.
37. [37] Momchilova, S., Itabashi, Y., Nikolova-Damyanova, B., Kuksis, A., Regioselective separation of isomeric triacylglycerols by reversed-phase high-performance liquid chromatography: Stationary phase and mobile phase effects. J. Sep. Sci. 29 (2006), 2578–2583.
38. [38] Kuroda, I., Nagai, T., Mizobe, H., Yoshimura, N., Gotoh, N., Wada, S., HPLC separation of triacylglycerol positional isomers on a polymeric ODS column. Anal. Sci. 24 (2008), 865–869.
39. [39] Mottram, H.R., Evershed, R.P., Structure analysis of triacylglycerol positional isomers using atmospheric pressure chemical ionisation mass spectrometry. Tetrahedron Lett. 37 (1996), 8593–8596.
40. [40] Mottram, H.R., Woodbury, S.E., Evershed, R.P., Identification of triacylglycerol positional isomers present in vegetable oils by high performance liquid chromatography atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom. 11 (1997), 1240–1252.
41. [41] Mottram, H.R., Crossman, Z.M., Evershed, R.P., Regiospecific characterisation of the triacylglycerols in animal fats using high performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. Analyst 126 (2001), 1018–1024.
42. [42] Jakab, A., Jablonkai, I., Forgacs, E., Quantification of the ratio of positional isomer dilinoleoyl-oleoyl glycerols in vegetable oils. Rapid Commun. Mass Spectrom. 17 (2003), 2295–2302.
43. [43] Fauconnot, L., Hau, J., Aeschlimann, J.M., Fay, L.B., Dionisi, F., Quantitative analysis of triacylglycerol regioisomers in fats and oils using reversed-phase high-performance liquid chromatography and atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom. 18 (2004), 218–224.
44. [44] Leskinen, H., Suomela, J.P., Kallio, H., Quantification of triacylglycerol regioisomers in oils and fat using different mass spectrometric and liquid chromatographic methods. Rapid Commun. Mass Spectrom. 21 (2007), 2361–2373.
45. [45] Leskinen, H.M., Suomela, J.P., Kallio, H.P., Quantification of triacylglycerol regioisomers by ultra-high-performance liquid chromatography and ammonia negative ion atmospheric pressure chemical ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 24 (2010), 1–5.
46. [46] Allen, J.W., DiRusso, C.C., Black, P.N., Triglyceride quantification by catalytic saturation and LC-MS/MS reveals an evolutionary divergence in regioisometry among green microalgae. Algal Res. 5 (2014), 23–31.
47. [47] Baiocchi, C., Medana, C., Dal Bello, F., Giancotti, V., Aigotti, R., Gastaldi, D., Analysis of regioisomers of polyunsaturated triacylglycerols in marine matrices by HPLC/HRMS. Food Chem. 166 (2015), 551–560.
48. [48] Nagy, K., Sandoz, L., Destaillats, F., Schafer, O., Mapping the regioisomeric distribution of fatty acids in triacylglycerols by hybrid mass spectrometry. J. Lipid Res. 54 (2013), 290–305.
49. [49] Byrdwell, W.C., The simulacrum system as a construct for mass spectrometry of triacylglycerols and others. Lipids 51 (2016), 211–227.
50. [50] Řezanka, T., Schreiberová, O., Čejková, A., Sigler, K., The genus Dracunculus – A source of triacylglycerols containing odd-numbered ω-phenyl fatty acids. Phytochemistry 72 (2011), 1914–1926.
51. [51] Řezanka, T., Schreiberová, O., Krulikovská, T., Masák, J., Sigler, K., RP-HPLC/MS-APCI analysis of odd-chain TAGs from Rhodococcus erythropolis including some regioisomers. Chem. Phys. Lipids 163 (2010), 373–380.
52. [52] Lísa, M., Netušilová, K., Franěk, L., Dvořáková, H., Vrkoslav, V., Holčapek, M., Characterization of fatty acid and triacylglycerol composition in animal fats using silver-ion and non-aqueous reversed-phase high-performance liquid chromatography/mass spectrometry and gas chromatography/flame ionization detection. J. Chromatogr. A 1218 (2011), 7499–7510.
53. [53] Gotoh, N., Matsumoto, Y., Nagai, T., Mizobe, H., Yoshinaga, K., Kojima, K., Kuroda, I., Kitamura, Y., Shimizu, T., Ishida, H., Wada, S., Actual ratio of triacylglycerol positional isomers in milk and cheese. J. Oleo Sci. 61 (2012), 173–180.
54. [54] Nagai, T., Gotoh, N., Mizobe, H., Yoshinaga, K., Kojima, K., Matsumoto, Y., Wada, S., Rapid separation of triacylglycerol positional isomers binding two saturated fatty acids using octacocyl silylation column. J. Oleo Sci. 60 (2011), 345–350.
55. [55] Iwasaki, Y., Yasui, M., Ishikawa, T., Irimescu, R., Hata, K., Yamane, T., Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography. J. Chromatogr. A 905 (2001), 111–118.
56. [56] Lísa, M., Holčapek, M., Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols. Anal. Chem. 85 (2013), 1852–1859.
57. [57] Itabashi, Y., Chiral separation of glycerolipids by high-performance liquid chromatography. J. Lipid Nutr. 21 (2012), 27–34.
58. [58] Nagai, T., Matsumoto, Y., Jiang, Y., Ishikawa, K., Wakatabe, T., Mizobe, H., Yoshinaga, K., Kojima, K., Kuroda, I., Saito, T., 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 (2013), 1009–1015.
59. [59] Alvarez, H.M., Steinbuchel, A., Triacylglycerols in prokaryotic microorganisms. Appl. Microbiol. Biotechnol. 60 (2002), 367–376.
60. [60] Dragone, G., Fernandes, B., Vicente, A., Teixeira, J.A., Current research, technology and education topics in applied microbiology and microbial biotechnology. Vilas, A.M., (eds.) Third Generation Biofuels from Microalgae, Formatex Research Center, Badajoz, 2010, 1355–1366.
61. [61] Řezanka, T., Lukavský, J., Nedbalová, L., Sigler, K., Effect of nitrogen and phosphorus starvation on the polyunsaturated triacylglycerol composition, including positional isomer distribution, in the alga Trachydiscus minutus. Phytochemistry 72 (2011), 2342–2351.
62. [62] Řezanka, T., Lukavský, J., Siřišťová, L., Sigler, K., Regioisomer separation and identification of triacylglycerols containing vaccenic and oleic acids, and α-and γ-linolenic acids, in thermophilic cyanobacteria Mastigocladus laminosus and Tolypothrix sp. Phytochemistry 78 (2012), 147–155.
63. [63] Řezanka, T., Lukavský, J., Nedbalová, L., Kolouchová, I., Sigler, K., Effect of starvation on the distribution of positional isomers and enantiomers of triacylglycerol in the diatom Phaeodactylum tricornutum. Phytochemistry 80 (2012), 17–27.
64. [64] Řezanka, T., Matoulková, D., Kolouchová, I., Masák, J., Sigler, K., Brewer's yeast as a new source of palmitoleic acid—analysis of triacylglycerols by LC–MS. J. Am. Oil Chem. Soc. 90 (2013), 1327–1342.
65. [65] Řezanka, T., Kolouchová, I., Čejková, A., Cajthaml, T., Sigler, K., Identification of regioisomers and enantiomers of triacylglycerols in different yeasts using reversed- and chiral-phase LC-MS. J. Sep. Sci. 36 (2013), 3310–3320.
66. [66] Řezanka, T., Lukavský, J., Nedbalová, L., Sigler, K., Production of structured triacylglycerols from microalgae. Phytochemistry 104 (2014), 95–104.
67. [67] Řezanka, T., Nedbalová, L., Sigler, K., Comparative analysis of triacylglycerols from different Stichococcus strains by RP-HPLC/APCI-MS and chiral HPLC. J. Appl. Phycol. 27 (2015), 685–696.
68. [68] Řezanka, T., Sigler, K., Separation of enantiomeric triacylglycerols by chiral-phase HPLC. Lipids 49 (2014), 1251–1260.
69. [69] Řezanka, T., Lukavský, J., Sigler, K., Nedbalová, L., Vítova, M., Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus. Phytochemistry 110 (2015), 37–45.
70. [70] Řezanka, T., Vítova, M., Nováková, A., Sigler, K., Separation and identification of odd chain triacylglycerols of the protozoan Khawkinea quartana and the mold Mortierella alpina using LC-MS. Lipids 50 (2015), 811–820.
71. [71] Řezanka, T., Sigler, K., Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms. Prog. Lipid Res. 48 (2009), 206–238.
72. [72] Chang, K.J.L., Mansour, M.P., Dunstan, G.A., Blackburn, S.I., Koutoulis, A., Nichols, P.D., Odd-chain polyunsaturated fatty acids in thraustochytrids. Phytochemistry 72 (2011), 1460–1465.