Production of structured triacylglycerols from microalgae

Phytochemistry

Volumn 104, Issue , 2014, Pages 95-104

  Řezanka, Tomáš ^a   Lukavský, Jaromír ^b   Nedbalová, Linda ^b,c   Sigler, Karel ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b INSTITUTE OF BOTANY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Chiral LC; Enantiomers; Microalgae; NARP LC MS APCI; Polyunsaturated fatty acids; Polyunsaturated triacylglycerols; Structured triacylglycerols

Indexed keywords

ALGAE; AUDOUINELLA; BALBIANIA INVESTIENS; MYRMECIA BISECTA; NANNOCHLOROPSIS; NANNOCHLOROPSIS LIMNETICA; PALMODICTYON VARIUM; PHAEODACTYLUM TRICORNUTUM; PSEUDOCHANTRANSIA; THOREA RAMOSISSIMA;

ARACHIDONIC ACID; FATTY ACID; ICOSAPENTAENOIC ACID; NITROGEN; PHOSPHORUS; TRIACYLGLYCEROL;

CHEMISTRY; GREEN ALGA; ISOLATION AND PURIFICATION; METABOLISM; MICROALGA; RED ALGA; STRAMENOPILE;

ARACHIDONIC ACID; CHLOROPHYTA; EICOSAPENTAENOIC ACID; FATTY ACIDS; MICROALGAE; NITROGEN; PHOSPHORUS; RHODOPHYTA; STRAMENOPILES; TRIGLYCERIDES;

EID: 84901821676     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.04.013     Document Type: Article

References (51)

1. P. Araujo, H. Zhu, J.F. Breivik, J.I. Hjelle, and Y. Zeng Determination and structural elucidation of triacylglycerols in krill oil by chromatographic techniques Lipids 49 2014 163 172
2. S. Boukhchina, J. Gresti, H. Kallel, and J. Bezard Stereospecific analysis of TAG from sunflower seed oil J. Am. Oil Chem. Soc. 80 2003 5 8
3. W.C. Byrdwell Qualitative and quantitative analysis of triacylglycerols by atmospheric pressure ionization (APCI and ESI) mass spectrometry techniques W.C. Byrdwell, Modern Methods for Lipid Analysis by Liquid Chromatography/Mass Spectrometry and Related Techniques 2005 AOCS Press Champaign 298 412
4. W.W. Christie Gas Chromatography and Lipids 1989 Oily Press Ayr, Scotland
5. R.A. Coleman, and P.L. Douglas Enzymes of triacylglycerol synthesis and their regulation Prog. Lipid Res. 43 2004 134 176 (Pubitemid 37492937)
6. L. Cossignani, M.S. Simonelti, A. Neri, and P. Damiani Structural analysis of triacylglycerol fraction and some its sub-fractions from an eicosapentaenoic acid/docosahexaenoic acid dietary supplement Z. Lebensm. Unters. Forsch. A 208 1999 203 207
7. S. Cubow The influence of positional distribution of fatty acids in native, interesterified and structure-specific lipids on atherogenesis J. Nutr. Biochem. 7 1996 530 541
8. L. Fauconnot, F. Robert, R. Villard, and F. Dionisi Chemical synthesis and NMR characterization of structured polyunsaturated triacylglycerols Chem. Phys. Lipids 139 2006 125 136 (Pubitemid 43185991)
9. N. Gotoh, Y. Matsumoto, T. Nagai, H. Mizobe, I. Otake, K. Ichioka, I. Kuroda, H. Watanabe, N. Noguchi, and S. Wada Actual ratios of triacylglycerol positional isomers consisting of saturated and highly unsaturated fatty acids in fishes and marine mammals Food Chem. 127 2011 467 472
10. S. Gronowitz, and B. Herslof ORD and CD studies of glycerides. 4 Unsaturated glycerides Chem. Phys. Lipids 23 1979 101 109
11. F. Guiheneuf, V. Mimouni, L. Ulmann, and G. Tremblin Combined effects of irradiance level and carbon source on fatty acid and lipid class composition in the microalga Pavlova lutheri commonly used in mariculture J. Exp. Mar. Biol. Ecol. 369 2009 136 143
12. R.R.R.L. Guillard, and C.J. Lorenzen Yellow-green algae with chlorophyllide C J. Phycol. 8 1972 10 14
13. 2+-dependent AraM from Bacillus subtilis Biochemistry 47 2008 7376 7384 (Pubitemid 351991016)
14. A. Halldorsson, C.D. Magnusson, and G.G. Haraldsson Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation Tetrahedron 59 2003 9101 9109 (Pubitemid 37329558)
15. C. Hellmuth, O. Uhl, M. Segura-Moreno, H. Demmelmair, and B. Koletzko Determination of acylglycerols from biological samples with chromatography-based methods J. Sep. Sci. 34 2011 3470 3483
16. E. Hita, A. Robles, B. Camacho, A. Ramírez, L. Esteban, M.J. Jiménez, M.M. Muñío, P.A. González, and E. Molina Production of structured triacylglycerols (STAG) rich in docosahexaenoic acid (DHA) in position 2 by acidolysis of tuna oil catalyzed by lipases Process Biochem. 42 2007 415 422 (Pubitemid 46329547)
17. Q. Hu, M. Sommerfeld, E. Jarvis, M. Ghirardi, M. Posewitz, M. Seibert, and A. Darzins Microalgal triacylglycerols as feedstocks for biofuel production: perspectives and advances Plant J. 54 2008 621 639 (Pubitemid 351678050)
18. R. Irimescu, K. Furihata, K. Hata, Y. Iwasaki, and T. Yamane Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structured triacylglycerols via 2-monoacylglycerols JAOCS J. Am. Oil Chem. Soc. 78 2001 743 748 (Pubitemid 32932263)
19. Y. Iwasaki, M. Yasui, T. Ishikawa, R. Irimescu, K. Hata, and T. Yamane Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography J. Chromatogr. A 905 2001 111 118 (Pubitemid 33646378)
20. I. Khozin-Goldberg, C. Bigogno, P. Shrestha, and Z. Cohen Nitrogen starvation induces the accumulation of arachidonic acid in the freshwater green alga Parietochloris incisa (Trebuxiophyceae) J. Phycol. 38 2002 991 994 (Pubitemid 35280765)
21. I. Khozin-Goldberg, U. Iskandarov, and Z. Cohen LC-PUFA from photosynthetic microalgae: occurrence, biosynthesis, and prospects in biotechnology Appl. Microbiol. Biotechnol. 91 2011 905 915
22. M. Kunesova, R. Braunerova, P. Hlavaty, E. Tvrzicka, B. Stankova, J. Skrha, J. Hilgertova, M. Hill, J. Kopecky, M. Wagenknecht, V. Hainer, M. Matoulek, J. Parizkova, A. Zak, and S. Svacina The influence of n-3 polyunsaturated fatty acids and very low calorie diet during a short-term weight reducing regimen on weight loss and serum fatty acid composition in severely obese women Physiol. Res. 55 2006 63 72 (Pubitemid 43276813)
23. I. Lang, L. Hodac, T. Friedl, and I. Feussner Fatty acid profiles and their distribution patterns in microalgae: a comprehensive analysis of more than 2000 strains from the SAG culture collection BMC Plant Biol. 11 2011 art. No. 124
24. H.M. Leskinen, J.-P. Suomela, and H.P. Kallio 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
25. M. Lisa, and M. Holcapek Triacylglycerols profiling in plant oils important in food industry, dietetics and cosmetics using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry J. Chromatogr. A 1198-1199 2008 115 130
26. M. Lisa, and M. Holcapek Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols Anal. Chem. 85 2013 1852 1859
27. M. Lisa, H. Velinska, and M. Holcapek Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards Anal. Chem. 81 2009 3903 3910
28. M. Lisa, K. Netusilova, L. Franek, H. Dvorakova, V. Vrkoslav, and M. Holcapek 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. 1218 2011 7499 7510
29. M.L. MacDonald, Q.R. Rogers, and J.G. Morris Nutrition of the domestic cat, a mammalian carnivore Annu. Rev. Nutr. 4 1984 521 562
30. H.R. Mottram Regiospecific analysis of triacylglycerols using high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry W.C. Byrdwell, Modern Methods for Lipid Analysis by Liquid Chromatography/Mass Spectrometry and Related Techniques 2005 AOCS Press Champaign, IL 276 297
31. H. Mu, and T. Porsgaard The metabolism of structured triacylglycerols Prog. Lipid Res. 44 2005 430 448 (Pubitemid 41613755)
32. M.D.M. Munio, A. Robles, L. Esteban, P.A. González, and E. Molina Synthesis of structured lipids by two enzymatic steps: Ethanolysis of fish oils and esterification of 2-monoacylglycerols Process Biochem. 44 2009 723 730
33. T. Nagai, H. Mizobe, I. Otake, K. Ichioka, K. Kojima, Y. Matsumoto, N. Gotoh, I. Kuroda, and S. Wada Enantiomeric separation of asymmetric triacylglycerol by recycle high-performance liquid chromatography with chiral column J. Chromatogr. A 1218 2011 2880 2886
34. T. Nagai, Y. Matsumoto, Y. Jiang, K. Ishikawa, T. Wakatabe, H. Mizobe, K. Yoshinaga, K. Kojima, I. Kuroda, T. Saito, F. Beppu, and N. Gotoh 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
35. D. Piomelli Arachidonic acid in cell signaling Curr. Opin. Cell Biol. 5 1993 274 280 (Pubitemid 23239781)
36. P. Quinlan, and S. Moore Modification of triglycerides by lipases: process technology and its application to the production of nutritionally improved fats INFORM 4 1993 580 585
37. P.R. Redden, X.R. Lin, J. Fahey, and D.F. Horrobin Stereospecific analysis of the major triacylglycerol species containing gamma-linolenic acid in evening-primrose oil and borage oil J. Chromatogr. 704 1995 99 111
38. T. Rezanka Polyunsaturated and unusual fatty-acids from slime-molds Phytochemistry 33 1993 1441 1444
39. T. Rezanka, and M. Podojil The very long-chain fatty-acids of the green-alga, Chlorella kessleri Lipids 19 1984 472 473
40. T. Rezanka, J. Lukavsky, L. Nedbalova, and K. Sigler 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
41. T. Rezanka, J. Lukavsky, L. Nedbalova, I. Kolouchova, and K. Sigler Effect of starvation on the distribution of positional isomers and enantiomers of triacylglycerol in the diatom Phaeodactylum tricornutum Phytochemistry 80 2012 17 27
42. T. Rezanka, I. Kolouchova, A. Cejkova, T. Cajthaml, and K. Sigler Identification of regioisomers and enantiomers of triacylglycerols in different yeasts using reversed- and chiral-phase LC-MS J. Sep. Sci. 36 2013 3310 3320
43. A. Robles, M.J. Jiménez, L. Esteban, P.A. González, L. Martín, A. Rodríguez, and E. Molina Enzymatic production of human milk fat substitutes containing palmitic and docosahexaenoic acids at sn-2 position and oleic acid at sn-1,3 positions Lebensm.-Wiss. Technol. 44 2011 1986 1992
44. G. Sempore, and J. Bezard Determination of molecular-species of oil triacylglycerols by reversed-phase and chiral-phase high-performance liquid-chromatography J. Am. Oil Chem. Soc. 68 1991 702 709
45. A.P. Simopoulos Omega-3 fatty acids in health and disease and in growth and development Am. J. Clin. Nutr. 54 1991 438 463 (Pubitemid 21898954)
46. M.M. Soumanou, U.T. Bornscheuer, U. Schmid, and R.D. Schmid Synthesis of structured triglycerides by lipase catalysis Fett/Lipid 100 1998 156 160
47. S.D. Stamatov, and J. Stawinski 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 (Pubitemid 350115420)
48. R. Staub Ernahrungs-physiologisch-okologische Untersuchungen an der planktonischen Blaualge Oscillatoria rubescens DC Schweiz. Z. Hydrol. 23 1961 82 198
49. E.R. Suarez, P.F. Mugford, A.J. Rolle, I.W. Burton, J.A. Walter, and J.A. Kralovec 13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates J. Am. Oil Chem. Soc. 87 2010 1425 1433
50. H. Takeuchi, M. Kasai, N. Taguchi, H. Tsuji, and M. Suzuk Effect of triacylglycerols containing medium- and long-chain fatty acids on serum triacylglycerols levels and body fat in college athletes J. Nutr. Sci. Vitaminol. 48 2002 109 114 (Pubitemid 34733441)
51. F.E. Ziegler, and G.D. Berger Mild method for the esterification of fatty-acids Synth. Commun. 9 1979 539 543