Geometrical and positional isomers of unsaturated furan fatty acids in food.
GC/MS
antioxidant
centrifugal partition chromatography
countercurrent chromatography
silver ion chromatography
unsaturated furan fatty acid
Journal
Lipids
ISSN: 1558-9307
Titre abrégé: Lipids
Pays: United States
ID NLM: 0060450
Informations de publication
Date de publication:
03 2023
03 2023
Historique:
revised:
14
10
2022
received:
08
08
2022
accepted:
01
11
2022
pubmed:
22
11
2022
medline:
14
3
2023
entrez:
21
11
2022
Statut:
ppublish
Résumé
Furan fatty acids (FuFA) are important antioxidants found in low concentrations in many types of food. In addition to conventional FuFA which normally feature saturated carboxyalkyl and alkyl chains, a few previous studies indicated the FuFA co-occurrence of low shares of unsaturated furan fatty acids (uFuFA). For their detailed analysis, the potential uFuFA were enriched by centrifugal partition chromatography (CPC) or countercurrent chromatography (CCC) followed by silver ion chromatography from a 4,7,10,13,16,19-docosahexaenoic acid ethyl ester oil, a 5,8,11,14,17-eicosapentaenoic acid ethyl ester oil and a latex glove extract. Subsequent gas chromatography with mass spectrometry (GC/MS) analysis enabled the detection of 16 individual uFuFA isomers with a double bond in conjugation with the central furan moiety. In either case, four instead of two uFuFA isomers previously reported in food, respectively, were detected by GC/MS. These isomers showed characteristic elution and abundance patterns in GC/MS chromatograms which indicated the presence of two pairs of cis/trans-isomers (geometrical isomers).
Substances chimiques
Fatty Acids, Unsaturated
0
Fatty Acids
0
Furans
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
69-79Informations de copyright
© 2022 The Authors. Lipids published by Wiley Periodicals LLC on behalf of AOCS.
Références
Batna A, Scheinkönig J, Spiteller G. The occurrence of furan fatty acids in Isochrysis sp. and Phaeodactylum tricornutum. BBA-Lipid Lipid Met. 1993;1166:171-6. https://doi.org/10.1016/0005-2760(93)90093-O
Batna A, Spiteller G. Herkunft des Sauerstoffatoms im Furanring von F-Säuren. Liebigs Ann Chem. 1991;1991:861-3. https://doi.org/10.1002/jlac.1991199101148
Batna A, Spiteller G. Biosynthesis of furan fatty acids in Saccharum species is Ca2+-dependent. Phytochemistry. 1993;32:311-5. https://doi.org/10.1016/S0031-9422(00)94987-2
Berthod A, Ruiz-Angel MJ, Carda-Broch S. Countercurrent chromatography: people and applications. J Chromatogr A. 2009;1216:4206-17. https://doi.org/10.1016/j.chroma.2008.10.071
Boselli E, Grob K, Lercker G. Determination of furan fatty acids in extra virgin olive oil. J Agric Food Chem. 2000;48:2868-73. https://doi.org/10.1021/jf990857j
Buxbaum LH. Über die Oxydation von Cyclohexanol mit molekularem Sauerstoff. Liebigs Ann Chem. 1967;706:81-9. https://doi.org/10.1002/jlac.19677060109
Dobson G, Christie WW, Nikolova-Damyanova B. Silver ion chromatography of lipids and fatty acids. J Chromatogr B. 1995;671:197-222. https://doi.org/10.1016/0378-4347(95)00157-E
Friesen JB, McAlpine JB, Chen S-N, Pauli GF. Countercurrent separation of natural products: an update. J Nat Prod. 2015;78:1765-96. https://doi.org/10.1021/np501065h
Gottstein V, Müller M, Günther J, Kuballa T, Vetter W. Direct 1H NMR quantitation of valuable furan fatty acids in fish oils and fish oil fractions. J Agric Food Chem. 2019;67:11788-95. https://doi.org/10.1021/acs.jafc.9b04711
Hammann S, Englert M, Müller M, Vetter W. Accelerated separation of GC-amenable lipid classes in plant oils by countercurrent chromatography in the co-current mode. Anal Bioanal Chem. 2015;407:9019-28. https://doi.org/10.1007/s00216-015-9068-5
Hammerschick T, Vetter W. Online hyphenation of centrifugal partition chromatography with countercurrent chromatography (CPC-CCC) and its application to the separation of saturated alkylresorcinols. Anal Bioanal Chem. 2022;414:5043-51. https://doi.org/10.1007/s00216-022-04136-x
Hammerschick T, Wagner T, Vetter W. Countercurrent chromatographic fractionation followed by gas chromatography/mass spectrometry identification of alkylresorcinols in rye. Anal Bioanal Chem. 2020;412:8417-30. https://doi.org/10.1007/s00216-020-02980-3
Hasma H, Subramaniam A. The occurrence of a furanoid fatty acid in Hevea brasiliensis latex. Lipids. 1978;13:905-7. https://doi.org/10.1007/BF02533847
Ishii K, Okajima H, Okada Y, Watanabe H. Effects of phosphatidylcholines containing furan fatty acid on oxidation in multilamellar liposomes. Chem Pharm Bull. 1989;37:1396-8. https://doi.org/10.1248/cpb.37.1396
Ishii K, Okajlma H, Koyamatsu T, Okada Y, Watanabe H. The composition of furan fatty acids in the crayfish. Lipids. 1988;23:818. https://doi.org/10.1007/BF02536228
Ito Y. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J Chromatogr A. 2005;1065:145-68. https://doi.org/10.1016/j.chroma.2004.12.044
Jandke J, Schmidt J, Spiteller G. Über das Verhalten von F-Säuren bei Oxidation mit Lipoxydase in Anwesenheit von SH-haltigen Verbindungen. Liebigs Ann Chem. 1988;1988:29-34. https://doi.org/10.1002/jlac.198819880107
Kirres C, Vetter W. Furan fatty acid content and homologue patterns of fresh green matrices. J Food Compos Anal. 2018;67:63-9. https://doi.org/10.1016/j.jfca.2018.01.001
Kröpfl A, Nemetz NJ, Goncalves Peca A, Vetter W. Countercurrent chromatography isolation of 11′-γ-tocomonoenol from pumpkin seed oil with detection of novel minor tocochromanols. J Am Oil Chem Soc. 2022;99:15-26. https://doi.org/10.1002/aocs.12559
Lauvai J, Becker A-K, Lehnert K, Schumacher M, Hieronimus B, Vetter W, et al. The furan fatty acid 9M5 acts as a partial ligand to peroxisome proliferator-activated receptor gamma and enhances adipogenesis in 3T3-L1 preadipocytes. Lipids. 2019;54:277-88. https://doi.org/10.1002/lipd.12152
Lemke RAS, Olson SM, Morse K, Karlen SD, Higbee A, Beebe ET, et al. A bacterial biosynthetic pathway for methylated furan fatty acids. J Biol Chem. 2020;295:9786-801. https://doi.org/10.1074/jbc.RA120.013697
Lemke RAS, Peterson AC, Ziegelhoffer EC, Westphall MS, Tjellström H, Coon JJ, et al. Synthesis and scavenging role of furan fatty acids. Proc Natl Acad Sci USA. 2014;111:E3450-7. https://doi.org/10.1073/pnas.1405520111
Liengprayoon S, Sriroth K, Dubreucq E, Vaysse L. Glycolipid composition of Hevea brasiliensis latex. Phytochemistry. 2011;72:1902-13. https://doi.org/10.1016/j.phytochem.2011.04.023
Masuchi Buscato MH, Müller F, Vetter W, Weiss J, Salminen H. Furan fatty acids in enriched ω-3 fish oil: oxidation kinetics with and without added monomethyl furan fatty acid as potential natural antioxidant. Food Chem. 2020;327:127087. https://doi.org/10.1016/j.foodchem.2020.127087
Mawlong I, Sujith Kumar MS, Singh D. Furan fatty acids: their role in plant systems. Phytochem Rev. 2016;15:121-7. https://doi.org/10.1007/s11101-014-9388-7
Müller F, Hogg M, Vetter W. Valuable furan fatty acids in soybeans and soy products. Eur Food Res Technol. 2020;246:1383-92. https://doi.org/10.1007/s00217-020-03497-w
Müller M, Hogg M, Ulms K, Vetter W. Concentrations, stability, and isolation of the furan fatty acid 9-(3-Methyl-5-pentylfuran-2-yl)-nonanoic acid from disposable latex gloves. J Agric Food Chem. 2017;65:7919-25. https://doi.org/10.1021/acs.jafc.7b02444
Müller M, Wasmer K, Vetter W. Multiple injection mode with or without repeated sample injections: strategies to enhance productivity in countercurrent chromatography. J Chromatogr A. 2018;1556:88-96. https://doi.org/10.1016/j.chroma.2018.04.069
Okada Y, Kaneko M, Okajima H. Hydroxyl radical scavenging activity of naturally occurring furan fatty acids. Biol Pharm Bull. 1996;19:1607-10. https://doi.org/10.1248/bpb.19.1607
Okada Y, Okajima H, Konishi H, Terauchi M, Ishii K, Liu I-M, et al. Antioxidant effect of naturally occurring furan fatty acids on oxidation of linoleic acid in aqueous dispersion. J Am Oil Chem Soc. 1990;67:858-62. https://doi.org/10.1007/BF02540506
Pacetti D, Alberti F, Boselli E, Frega NG. Characterisation of furan fatty acids in Adriatic fish. Food Chem. 2010;122:209-15. https://doi.org/10.1016/j.foodchem.2010.02.059
Scheinkönig J, Spiteller G. Herkunft der Methylsubstituenten in F-Säuren. Liebigs Ann Chem. 1991;1991:451-3. https://doi.org/10.1002/jlac.199119910182
Scheinkönig J, Spiteller G. F-Säure-haltige Phospholipidmoleküle in Zuckerrohrzellen. Liebigs Ann Chem. 1993;1993:121-4. https://doi.org/10.1002/jlac.199319930122
Schödel R, Spiteller G. Über das Vorkommen von F-Säuren in Rinderleber und deren enzymatischen Abbau bei Gewebeverletzung. Liebigs Ann Chem. 1987;1987:459-62. https://doi.org/10.1002/jlac.198719870354
Schröder M, Vetter W. Detection of 430 fatty acid methyl esters from a transesterified butter sample. J Am Oil Chem Soc. 2013;90:771-90. https://doi.org/10.1007/s11746-013-2218-z
Shirasaka N, Nishi K, Shimizu S. Biosynthesis of furan fatty acids (F-acids) by a marine bacterium Shewanella putrefaciens. BBA-Lipid Lipid Met. 1997;1346:253-60. https://doi.org/10.1016/S0005-2760(97)00042-8
Skalicka-Woźniak K, Garrard I. Counter-current chromatography for the separation of terpenoids: a comprehensive review with respect to the solvent systems employed. Phytochem Rev. 2014;13:547-72. https://doi.org/10.1007/s11101-014-9348-2
Spiteller G. Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids. 2005;40:755-71. https://doi.org/10.1007/s11745-005-1438-5
Svetlana Momchilova BN-D. Stationary phases for silver ion chromatography of lipids: preparation and properties. J Sep Sci. 2003;2003:261-70. https://doi.org/10.1002/jssc.200390032
Uchida H, Itabashi Y, Watanabe R, Matsushima R, Oikawa H, Suzuki T, et al. Detection and identification of furan fatty acids from fish lipids by high-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight mass spectrometry. Food Chem. 2018;252:84-91. https://doi.org/10.1016/j.foodchem.2018.01.044
Vetter W, Laure S, Wendlinger C, Mattes A, Smith AWT, Knight DW. Determination of furan fatty acids in food samples. J Am Oil Chem Soc. 2012;89:1501-8. https://doi.org/10.1007/s11746-012-2038-6
Vetter W, Ulms K, Wendlinger C, van Rijn J. Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system. NFS J. 2016;2:8-14. https://doi.org/10.1016/j.nfs.2015.11.001
Vetter W, Wendlinger C. Furan fatty acids-valuable minor fatty acids in food. Lipid Technol. 2013;25:7-10. https://doi.org/10.1002/lite.201300247
Wakimoto T, Kondo H, Nii H, Kimura K, Egami Y, Oka Y, et al. Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus. Proc Natl Acad Sci USA. 2011;108:17533-7. https://doi.org/10.1073/pnas.1110577108
Wendlinger C, Hammann S, Vetter W. Various concentrations of erucic acid in mustard oil and mustard. Food Chem. 2014;153:393-7. https://doi.org/10.1016/j.foodchem.2013.12.073
Wendlinger C, Hammann S, Vetter W. Detailed study of furan fatty acids in total lipids and the cholesteryl ester fraction of fish liver. Food Anal Methods. 2016;9:459-68. https://doi.org/10.1007/s12161-015-0211-x
Wendlinger C, Vetter W. High concentrations of furan fatty acids in organic butter samples from the German market. J Agric Food Chem. 2014;62:8740-4. https://doi.org/10.1021/jf502975b
Xu L, Sinclair AJ, Faiza M, Li D, Han X, Yin H, et al. Furan fatty acids-beneficial or harmful to health? Prog Lipid Res. 2017;68:119-37. https://doi.org/10.1016/j.plipres.2017.10.002