Separation and Identification of Odd Chain Triacylglycerols of the Protozoan Khawkinea quartana and the Mold Mortierella alpina Using LC-MS

Lipids

Volumn 50, Issue 8, 2015, Pages 811-820

  Řezanka, Tomáš ^a   Vítová, Milada ^a   Nováková, Alena ^a   Sigler, Karel ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

Chiral LC APCI MS; Khawkinea quartana; Mold; Mortierella alpina; Protozoan; Structured triacylglycerols

Indexed keywords

TRIACYLGLYCEROL;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; DRUG IDENTIFICATION; ENANTIOMER; KHAWKINEA QUARTANA; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MORTIERELLA ALPINA; NONHUMAN; PROTOZOON; SEPARATION TECHNIQUE; STANDARD; STEREOSPECIFICITY; CHEMISTRY; EUGLENA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MORTIERELLA; PROCEDURES;

EUGLENA QUARTANA; MORTIERELLA ALPINA; PROTOZOA;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EUGLENA; MASS SPECTROMETRY; MORTIERELLA; TRIGLYCERIDES;

EID: 84938555014     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-015-4042-8     Document Type: Article

References (34)

1. Rezanka T, Sigler K (2009) Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms. Progr Lip Res 48:206-238
2. Schlenk H (1971) Odd numbered polyunsaturated fatty acids. Prog Chem Fats Lipids 9:587-605
3. Diedrich M, Henschel KP (1990) The natural occurrence of unusual fatty acids Part 1. Odd numbered fatty acids. Die Nahrung 34:935-943
4. Vlaeminck B, Fievez V, Cabrita ARJ, Fonseca AJM, Dewhurst RJ (2006) Factors affecting odd- and branched-chain fatty acids in milk: a review. Animal Feed Sci Technol 131:389-417
5. Kalo P, Kemppinen A, Ollilainen V (2009) Determination of triacylglycerols in butterfat by normal-phase HPLC and electrospray-tandem mass spectrometry. Lipids 44:169-195
6. Holcapek M, Jandera P, Zderadicka P, Hruba L (2003) Characterization of triacylglycerol and diacylglycerol composition of plant oils using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J Chromatogr A 1010:195-215
7. Cherif AO, Leveque N, Messaouda MB, Kallel H, Tchapla A, Moussa F (2014) NARP-HPLC/MS5 and silver cationization fingerprinting of triacylglycerols in wild and cultivar Tunisian peanut kernels. LWT - Food Sci Tech 57:236-242
8. Rezanka T, Schreiberova O, Krulikovska T, Masak J, Sigler K (2010) RP-HPLC/MS-APCI analysis of odd-chain TAGs from Rhodococcus erythropolis including some regioisomers. Chem Phys Lipids 163:373-380
9. Schreiberova O, Krulikovska T, Sigler K, Cejkova A, Rezanka T (2010) RP-HPLC/MS-APCI analysis of branched chain tag prepared by precursor-directed biosynthesis with Rhodococcus erythropolis. Lipids 45:743-756
10. Vasskog T, Andersen JH, Hansen E, Svenson J (2012) Characterization and cytotoxicity studies of the rare 21:4n-7 acid and other polyunsaturated fatty acids from the marine opisthobranch Scaphander lignarius, isolated using bioassay guided fractionation. Marine Drugs 10:2676-2690
11. Chang KJL, Dunstan GA, Abell GCJ, Clementson LA, Blackburn SI, Nichols PD, Koutoulis A (2012) Biodiscovery of new Australian thraustochytrids for production of biodiesel and long-chain omega-3 oils. Appl Microbiol Biotechnol 93:2215-2231
12. Chang KJL, Mansour MP, Dunstan GA, Blackburn SI, Koutoulis A, Nichols PD (2011) Odd-chain polyunsaturated fatty acids in thraustochytrids. Phytochemistry 72:1460-1465
13. Rohner CA, Couturier LIE, Richardson AJ, Pierce SJ, Prebble CEM, Gibbons MJ, Nichols PD (2013) Diet of whale sharks Rhincodon typus inferred from stomach content and signature fatty acid analyses. Mar Ecol Prog Ser 493:219-235
14. Simonetti MS, Blasi F, Bosi A, Maurizi A, Cossignani L, Damiani P (2008) Stereospecific analysis of triacylglycerol and phospholipid fractions of four freshwater fish species: Salmo trutta, Ictalurus punctatus, Ictalurus melas and Micropterus salmoides. Food Chem 110:199-206
15. Shimizu S, Kawashima H, Akimoto K, Shinmen Y, Yamada H (1991) Production of odd chain polyunsaturated fatty-acids by Mortierella fungi. J Amer Oil Chem Soc 68:254-258
16. Shirasaka N, Yokochi T, Shimizu S (1995) Formation of a novel odd chain polyunsaturated fatty-acid, 5,8,11,14,17-cis-nonadecapentaenoic acid, by an EPA-producing aquatic fungus, Saprolegnia sp, 28YTF-1. Biosci Biotechnol Biochem 59:1963-1965
17. Mottram HR (2005) Regiospecific analysis of triacylglycerols using high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. In: Byrdwell WC (ed) Modern Methods for Lipid Analysis by Liquid Chromatography/Mass Spectrometry and Related Techniques. AOCS Press, Champaign, IL, pp 276-297
18. Lisa M, Holcapek M (2013) Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols. Anal Chem 85:1852-1859
19. Itabashi Y (2012) Chiral separation of glycerolipids by high-performance liquid chromatography. J Lipid Nutrition 21:27-34
20. Pringsheim E.G. http://sagdb.uni-goettingen.de/culture-media/03%20Soil%20Water%20Media.pdf
21. Christie WW (1989) Gas Chromatography and Lipids. Oily Press, Ayr, Scotland
22. Ziegler FE, Berger GD (1979) Mild method for the esterification of fatty-acids. Synth Commun 9:539-543
23. Halldorsson A, Magnusson CD, Haraldsson GG (2003) Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation. Tetrahedron 59:9101-9109
24. Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911-917
25. Dembitsky VM, Rezanka T, Bychek IA (1992) Fatty-acids and phospholipids from lichens of the order Lecanorales. Phytochemistry 31:851-853
26. Dembitsky VM, Rezanka T, Rozentsvet OA (1993) Lipid-composition of 3 macrophytes from the Caspian Sea. Phytochemistry 33:1015-1019
27. Dembitsky VM, Rezanka T, Bychek IA, Shustov MV (1991) Identification of fatty-acids from Cladonia lichens. Phytochemistry 30:4015-4018
28. Rezanka T, Sigler K (2014) Separation of enantiomeric triacylglycerols by chiral-phase HPLC. Lipids 49:1251-1260
29. Momchilova S, Tsuji K, Itabashi Y, Nikolova-Damyanova B, Kuskis A (2004) Resolution of triacylglycerol positional isomers by reversed-phase high-performance liquid chromatography. J Sep Sci 27:1033-1036
30. Rezanka T, Lukavsky J, Sigler K, Nedbalova L, Vitova M (2015) Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus. Phytochemistry 110:37-45
31. Nagai T, Matsumoto Y, Jiang YY, Ishikawa K, Wakatabe T, Mizobe H, Yoshinaga K, Kojima K, Kuroda I, Saito T, Beppu F, Gotoh N (2013) 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
32. Stamatov SD, Stawinski J (2007) 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 5:3787-3800
33. Lisa M, Holcapek M, Bohac M (2009) Statistical evaluation of triacylglycerol composition in plant oils based on high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry data. J Agr Food Chem 57:6888-6898
34. Lang I, Hodac L, Friedl T, Feussner I (2011) 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 11:124