Bibliography of Mass Spectrometry of Fatty Acids

Mild Ionization Techniques

Scottish thistle Atmospheric-pressure chemical-ionization (APCI), electrospray and several other are mild ionization techniques are available and they are particularly effective when linked to high-performance liquid chromatography. In conjunction with tandem-MS techiques, these can give useful structural information on fatty acids. Another very promising technique involves acetonitrile-chemical-reaction tandem mass spectrometry in the gas phase for locating double bonds in fatty acid methyl esters (from the laboratory of Professor J.T. Brenna mainly). In addition, there is now greatest interest in the use of the Paterno-Buchi reaction.

The following references were collected as part of our regular literature reviews for our own research purposes, but this topic has never been of importance to us, so the literature coverage is far from complete. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. New references may be added at irregular intervals - check the bottom of the page for when it was last updated. DOI addresses are included from 2014 onwards. As I am no longer able to keep up the literature on this topic, I recommend the following reviews -

Chen, C., Li, R.J. and Wu, H. Recent progress in the analysis of unsaturated fatty acids in biological samples by chemical derivatization-based chromatography-mass spectrometry methods. J. Chromatogr. B, 1215, 123572 (2023); DOI.

Wang, Z., Yang, T.X., Brenna, J.T. and Wang, D.H. Fatty acid isomerism: analysis and selected biological functions. Food Function, in press (2023); DOI.

Alves, S.P. and Bessa,R.J.B. Identification of cis-12,cis-15 octadecadienoic acid and other minor polyenoic fatty acids in ruminant fat. Eur. J. Lipid Sci. Technol., 109, 879-883 (2007).
Alves, S.P., Maia, M.R.G., Bessa, R.J.B., Fonseca, A.J.M. and Cabrita, A.R.J. Identification of C18 intermediates formed during stearidonic acid biohydrogenation by rumen microorganisms in vitro. Lipids, 47, 171-183 (2012).
Alves, S.P., Tyburczy,C., Lawrence,P., Bessa,R.J.B. and Brenna,J.T. Acetonitrile covalent adduct chemical ionization tandem mass spectrometry of non-methylene-interrupted pentaene fatty acid methyl esters. Rapid Commun. Mass Spectrom., 25, 1933-1941 (2011).
Bicalho, B., David,F., Rumplel,K., Kindt,E. and Sandra,P. Creating a fatty acid methyl ester database for lipid profiling in a single drop of human blood using high resolution capillary gas chromatography and mass spectrometry. J. Chromatogr. A, 1211, 120-128 (2008).
Borden, S.A., Damer, H.N., Krogh, E.T. and Gill, C.G. Direct quantitation and characterization of fatty acids in salmon tissue by condensed phase membrane introduction mass spectrometry (CP-MIMS) using a modified donor phase. Anal. Bioanal. Chem., 411, 291-303 (2019); DOI.
Brenna, J.T. Double bond localization in fatty acid methyl esters by covalent adduct chemical ionization (CACI) tandem mass spectrometry. Lipid Technology, 17, 229-232 (2005).
Brenna, J.T. Structural analysis of unsaturated fatty acid methyl ester isomers with acetonitrile covalent adduct chemical ionization. In: Lipid Analysis and Lipidomics: New Techniques and Applications. pp. 157-172 (ed: M.M. Mossoba, J.K.G. Kramer, J.T. Brenna and R.E. McDonald, AOCS Press, Champaign, USA) (2006)
Brenna, J.T. Fatty acid analysis by high resolution gas chromatography and mass spectrometry for clinical and experimental applications. Curr. Opin. Clin. Nutr. Metab. Care, 16, 548-554 (2013).
Chonglo, L., Tian, R., Shi, R.Y., Ouyang, Z. and Xia, Y. Coupling the Paterno-Buchi (PB) reaction with mass spectrometry to study unsaturated fatty acids in mouse model of multiple sclerosis. Front. Chem., 7, 807 (2019); DOI.
Gallon, A.A. and Pryor,W.A. The identification of the allylic nitrite and nitro derivatives of methyl linoleate and methyl linolenate by negative chemical ionization mass spectroscopy. Lipids, 28, 125-133 (1993).
Garlito, B., Portoles, T., Niessen, W.M.A., Navarro, J.C., Hontoria, F., Monroig, O., Varo, I. and Serrano, R. Identification of very long-chain (>C-24) fatty acid methyl esters using gas chromatography coupled to quadrupole/time-of-flight mass spectrometry with atmospheric pressure chemical ionization source. Anal. Chim. Acta, 1051, 103-109 (2019); DOI.
Gaugg, M.T., Bruderer, T., Nowak, N., Eiffert, L., Sinues, P.M.L., Kohler, M. and Zenobi, R. Mass-spectrometric detection of omega-oxidation products of aliphatic fatty acids in exhaled breath. Anal. Chem., 89, 10329-10334 (2017); DOI.
Gómez-Cortés, P., Brenna, J.T., Lawrence, P. and de la Fuente, M.A. Novel characterisation of minor alpha-linolenic acid isomers in linseed oil by gas chromatography and covalent adduct chemical ionisation tandem mass spectrometry. Food Chem., 200, 141-145 (2016); DOI.
Gómez-Cortés, P., Tyburczy,C., Brenna,J.T., Juárez,M. and Angel de la Fuente,M. Characterization of cis-9,trans-11,trans-15-C18:3 in milk fat by GC and covalent adduct chemical ionization tandem MS. J. Lipid Res., 50, 2412-2420 (2009).
Goulitquer, S., Dreano,Y., Berthou,F., Corcos,L. and Lucas,D. Determination of epoxyeicosatrienoic acids in human red blood cells and plasma by GC/MS in the NICI mode. J. Chromatogr. B, 876, 83-88 (2008).
Gu, W.Y., Liu, M.X., Sun, B.Q., Guo, M.Q., Wu, J.L. and Li, N. Profiling of polyunsaturated fatty acids in human serum using off-line and on-line solid phase extraction-nano-liquid chromatography-quadrupole-time-of-flight mass spectrometry. J. Chromatogr. A, 1537, 141-146 (2018); DOI.
Hong, S., Cheng, T,-Y., Layre, E., Sweet, L., Young, D.C., Posey, J.E., Butler, W.R. and Moody, D.B. Ultralong C100 mycolic acids support the assignment of Segniliparus as a new bacterial genus. PLoS One, 7, e39017 (2012); DOI.
Infante, J.P., Tschanz,C.L., Shaw,N., Michaud,A.L., Lawrence,P. and Brenna,J.T. Straight-chain acyl-CoA oxidase knockout mouse accumulates extremely long chain fatty acids from alpha-linolenic acid: Evidence for runaway carousel-type enzyme kinetics in peroxisomal beta-oxidation diseases. Mol. Genetics Metab., 75, 108-119 (2002).
Kuiper, H.C., Wei, N., McGunigale, S.L. and Vesper, H.W. Quantitation of trans-fatty acids in human blood via isotope dilution-gas chromatography-negative chemical ionization-mass spectrometry. J. Chromatogr. B, 1076, 35-43 (2018); DOI.
Lanéelle, M.A. Eynard, N., Spina, L., Lemassu, A., Laval, F., Huc, E., Etienne, G., Marrakchi, H. and Daffé, M. Structural elucidation and genomic scrutiny of the C60-C100 mycolic acids of Segniliparus rotundus. Microbiology, 159, 191-203 (2013); DOI.
Lawrence, P. and Brenna,J.T. Acetonitrile covalent adduct chemical ionization mass spectrometry for double bond localization in non-methylene-interrupted polyene fatty acid methyl esters. Anal. Chem., 78, 1312-1317 (2006).
Lopez-Bascon, M.A. Calderon-Santiago, M. and Priego-Capote, F. Confirmatory and quantitative analysis of fatty acid esters of hydroxy fatty acids in serum by solid phase extraction coupled to liquid chromatography tandem mass spectrometry. Anal. Chim. Acta, 943, 82-88 (2016); DOI.
Losito, I., Facchini, L., Valentini, A., Cataldi, T.R.I. and Palmisano, F. Fatty acidomics: Evaluation of the effects of thermal treatments on commercial mussels through an extended characterization of their free fatty acids by liquid chromatography - Fourier transform mass spectrometry. Food Chem., 255, 309-322 (2018); DOI.
Ma, X., Zhao, X., Li, J., Zhang, W., Cheng, J.-X., Ouyang, Z. and Xia, Y. Photochemical tagging for quantitation of unsaturated fatty acids by mass spectrometry. Anal. Chem., 88, 8931-8935 (2016); DOI.
Marshall, D.L., Saville, J.T., Maccarone, A.T., Ailuri, R., Kelso, M.J., Mitchell, T.W. and Blanksby, S.J. Determination of ester position in isomeric (O-acyl)-hydroxy fatty acids by ion trap mass spectrometry. Rapid Commun. Mass Spectrom., 30, 2351-2359 (2016); DOI.
Michaud, A.L, Lawrence,P., Adlof,R. and Brenna,J.T. On the formation of conjugated linoleic acid diagnostic ions with acetonitrile chemical ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom., 19, 363-368 (2005).
Michaud, A.L, Yurawecz,M.P., Delmonte,P., Corl,B.A., Bauman,D.E. and Brenna,J.T. Identification and characterization of conjugated fatty acid methyl esters of mixed double bond geometry by acetonitrile chemical ionization tandem mass spectrometry. Anal. Chem., 75, 4925-4930 (2003).
Michaud, A.L., Diau,G.Y., Abril,R. and Brenna,J.T. Double bond localization in minor homoallylic fatty acid methyl esters using acetonitrile chemical ionization tandem mass spectrometry. Anal. Biochem., 307, 348-360 (2002).
Mok, H.J., Lee, J.W., Bandu, R., Kang, H.S., Kim, K.H. and Kim, K.P. A rapid and sensitive profiling of free fatty acids using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) after chemical derivatization. RSC Adv., 6, 32130-32139 (2016); DOI.
Murphy, R.C., Okuno, T., Johnson, C.A. and Barkleyte, R.M. Determination of double bond positions in polyunsaturated fatty acids using the photochemical Paterno-Buchi reaction with acetone and tandem mass spectrometry. Anal. Chem., 89, 8545-8553 (2017); DOI.
Nichols, D.S. and Davies,N.W. Improved detection of polyunsaturated fatty acids as phenacyl esters using liquid chromatography-ion trap mass spectrometry. J. Microb. Methods, 50, 103-113 (2002).
Oldham, N.J. and Svatos,A. Determination of the double bond position in functionalized monoenes by chemical ionization ion-trap mass spectrometry using acetonitrile as a reagent gas. Rapid Commun. Mass Spectrom., 13, 331-336 (1999).
Ozaki, H., Nakano, Y., Sakamaki, H., Yamanaka, H. and Nakai, M. Basic eluent for rapid and comprehensive analysis of fatty acid isomers using reversed-phase high performance liquid chromatography/Fourier transform mass spectrometry. J. Chromatogr. A, 1585, 113-120 (2019); DOI.
Park, H.G., Zhang, J.Y., Foster, C., Sudilovsky, D., Schwed, D.A., Mecenas, J., Devapatla, S., Lawrence, P., Kothapalli, K.S.D. and Brenna, J.T. A rare eicosanoid precursor analogue, sciadonic acid (5Z,11Z,14Z-20:3), detected in vivo in hormone positive breast cancer tissue. PLEFA, 134, 1-6 (2018); DOI.
Park, W.J., Kothapalli,K.S.D., Lawrence,P., Tyburczy,C. and, Brenna,J.T. An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta 8-desaturates 20:2n-6 and 20:3n-3. J. Lipid Res., 50, 1195-1202 (2009).
Pereira, E.R., Kopp, J.F., Raab, A., Krupp, E.M., Menoyo, J.D., Carasek, E., Welz, B. and Feldmann, J. Arsenic containing medium and long chain fatty acids in marine fish oil identified as degradation products using reversed-phase HPLC-ICP-MS/ESI-MS. J. Anal. Atomic Spectr., 31, 1836-1845 (2016); DOI.
Ran-Ressler, R.R., Lawrence, P. and Brenna, J.T. Structural characterization of saturated branched chain fatty acid methyl esters by collisional dissociation of molecular ions generated by electron ionization. J. Lipid Res., 53, 195-203 (2012).
Rezanka, T. Analysis of very long chain polyunsaturated fatty acids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Biochem. System. Ecol., 28, 847-856 (2000).
Rezanka, T. Analysis of polyunsaturated fatty acids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J. High Resolut. Chromatogr., 23, 338-342 (2000).
Rezanka, T. Identification of very long chain fatty acids by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy from green alga Chlorella kessleri. J. Sep. Sci., 25, 1332-1336 (2002).
Rezanka, T. and Dembitsky,V.A. Tetratriacontanonaenoic acid, first natural acid with nine double bonds isolated from a crustacean Bathynella natans. Tetrahedron, 60, 4261-4264 (2004).
Rezanka, T. and Sigler,K. Identification of very long chain unsaturated fatty acids from Ximenia oil by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy. Phytochemistry, 68, 925-934 (2007).
Rezanka, T. and Votruba,J. Analysis of fatty acids by APCI-MS. In 'Modern Methods for Lipid Analysis by Liquid Chromatography/Mass Spectrometry and Related Techniques' (Ed. W.C. Byrdwell, AOCS Press, Champaign), pp. 242-275 (2005).
Rezanka, T., Nedbalova,L. and Sigler,K. Identification of very-long-chain polyunsaturated fatty acids from Amphidinium carterae by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy. Phytochemistry, 69, 2391-2399 (2008).
Rezanka, T., Nedbalova,L. and Sigler,K. Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry. Phytochemistry, 69, 2849-2855 (2008).
Ritter, A., Goulitquer,S., Salaun,J.P., Tonon,T., Correa,J.A. and Potin,P. Copper stress induces biosynthesis of octadecanoid and eicosanoid oxygenated derivatives in the brown algal kelp Laminaria digitata. New Phytologist, 180, 809-821 (2008).
Rush, D., Jaeschke,A., Hopmans,E.C., Geenevasen,J.A.J., Schouten,S. and Damste,J.S.S. Short chain ladderanes: Oxic biodegradation products of anammox lipids. Geochim. Cosmochim. Acta, 75, 1662-1671 (2011).
Saba, A., Mazzini,F., Raffaelli,A., Mattei,A. and Salvadori,P. Identification of 9(E),11(E)-18 : 2 fatty acid methyl ester at trace level in thermal stressed olive oils by GC coupled to acetonitrile CI-MS and CI-MS/MS, a possible marker for adulteration by addition of deodorized olive oil. J. Agric. Food Chem., 53, 4867-4872 (2005).
Schlotterbeck, J., Cebo, M., Kolb, A. and Lammerhofer, M. Quantitative analysis of chemoresistance-inducing fatty acid in food supplements using UHPLC-ESI-MS/MS. Anal. Bioanal. Chem., 411, 479-491 (2019); DOI.
Schroter, J., Griesinger, H., Reuss, E., Schulz, M., Riemer, T., Suss, R., Schiller, J. and Fuchs, B. Unexpected products of the hypochlorous acid-induced oxidation of oleic acid: A study using high performance thin-layer chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A, 1439, 89-96 (2016); DOI.
Semeraro, M., Rizzo, C., Boenzi, S., Cappa, M., Bertini, E., Antonetti, G. and Dionisi-Vici, C. A new multiplex method for the diagnosis of peroxisomal disorders allowing simultaneous determination of plasma very-long-chain fatty acids, phytanic, pristanic, docosahexaenoic and bile acids by high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry. Clin. Chim. Acta, 458, 159-164 (2016); DOI.
Sun, C.X., Zhao, Y.Y. and Curtis, J.M. The direct determination of double bond positions in lipid mixtures by liquid chromatography/in-line ozonolysis/mass spectrometry. Anal. Chim. Acta, 762, 68-75 (2013).
Treschow, A.P., Hodges,L.D., Wright,P.F.A., Wynne,P.M., Kalafatis,N. and Macrides,T.A. Novel anti-inflammatory omega-3 PUFAs from the New Zealand green-lipped mussel, Perna canaliculus. Comp. Biochem. Physiol. B, 147, 645-656 (2007).
Tsikas, D., Zoerner,A.A. and Jordan,J. Oxidized and nitrated oleic acid in biological systems: Analysis by GC-MS/MS and LC-MS/MS, and biological significance. Biochim. Biophys. Acta, 1811, 694-705 (2011)
Uchida, H., Itabashi, Y., Watanabe, R., Matsushima, R., Oikawa, H., Suzuki, T., Hosokawa, M., Tsutsumi, N., Ura, K., Romanazzi, D. and Miller, M.R. 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., 252, 84-91 (2018); DOI.
Uenishi, Y., Takii,T., Yano,I. and Sunagawa,M. Separation and molecular characterization of mycolic acid from the cell wall skeleton of Mycobacterium bovis BCG Tokyo 172 (SMP-105) and BCG substrains by normal-phase high performance liquid chromatography and liquid chromatography/mass spectrometry. J. Microbiol. Methods, 77, 320-322 (2009).
Uhlig, S., Negard, M., Heldal, K.K., Straumfors, A., Madso, L., Bakke, B. and Eduard, W. Profiling of 3-hydroxy fatty acids as environmental markers of endotoxin using liquid chromatography coupled to tandem mass spectrometry. J. Chromatogr. A, 1434, 119-126 (2016); DOI.
Valto, P., Knuutinen,J. and Alen,R. Resin and fatty-acid analysis by solid-phase extraction coupled to atmospheric pressure chemical ionization-mass spectrometry. Int. J. Environ. Anal. Chem., 87, 87-97 (2007).
Van Pelt, C.K. and Brenna,J.T. Acetonitrile chemical ionization tandem mass spectrometry to locate double bonds in polyunsaturated fatty acid methyl esters. Anal. Chem., 71, 1981-1989 (1999).
Van Pelt, C.K., Carpenter,B.K. and Brenna,J.T. Studies of structure and mechanism in acetonitrile chemical ionization tandem mass spectrometry of polyunsaturated fatty acid methyl esters. J. Am. Soc. Mass Spectrom., 10, 1253-1262 (1999).
Van Pelt, C.K., Huang,M.C., Tschanz,C.L. and Brenna,J.T. An octaene fatty acid, 4,7,10,13,16,19,22,25-octacosaoctaenoic acid (28:8n-3), found in marine oils. J. Lipid Res., 40, 1501-1505 (1999).
Vrkoslav, V. and Cvacka, J. Identification of the double-bond position in fatty acid methyl esters by liquid chromatography/atmospheric pressure chemical ionisation mass spectrometry. J. Chromatogr. A, 1259, 244-250 (2012).
Wang, Z., Yang, T.X., Brenna, J.T. and Wang, D.H. Fatty acid isomerism: analysis and selected biological functions. Food Function, in press (2023); DOI.
Wolyniak, C.J., Brenna,J.T., Murphy,K.J. and Sinclair,A.J. Gas chromatography-chemical ionization-mass spectrometric fatty acid analysis of a commercial supercritical carbon dioxide lipid extract from New Zealand green-lipped mussel (Perna canaliculus). Lipids, 40, 355-360 (2005).
Wood, P.L., Scoggin, K., Ball, B.A., Troedsson, M.H. and Squires, E.L. Lipidomics of equine sperm and seminal plasma: Identification of amphiphilic (O-acyl)-omega-hydroxy-fatty acids. Theriogenology, 86, 1212-1221 (2016); DOI.
Wu, Q., Comi, T.J., Li, B., Rubakhin, S.S. and Sweedler, J.V. On-tissue derivatization via electrospray deposition for matrix assisted laser desorption/ionization mass spectrometry imaging of endogenous fatty acids in rat brain tissues. Anal. Chem., 88, 5988-5995 (2016); DOI.
Xie, X.B. and Xia, Y. Analysis of conjugated fatty acid isomers by the Paterno-Buchi reaction and trapped ion mobility mass spectrometry. Anal. Chem., 91, 7173-7180 (2019); DOI.
Xu, Y.H. and Brenna,J.T. Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond localization in monoene- and diene-containing triacylglycerols. Anal. Chem., 79, 2525-2536 (2007).
Xu, Y.-J. and Zhang, J. Determination of fatty acid methyl esters by GC-triple quadrupole MS using electron and chemical ionization. Bioanalysis, 5, 1527-1543 (2013); DOI.
Yin, H.Y. and Porter,N.A. New insights regarding the autoxidation of polyunsaturated fatty acids. Antiox. Redox Signaling, 7, 170-184 (2005).
You, J., Zhao,X., Suo,Y., Li,Y., Wang,H. and Chen,G. Determination of long-chain fatty acids in bryophyte plants extracts by HPLC with fluorescence detection and identification with MS. J. Chromatogr. B, 848, 283-291 (2007).
Zahardis, J., LaFranchi,B.W. and Petrucci,G.A. Photoelectron resonance capture ionization mass spectrometry of fatty acids in olive oil. Eur. J. Lipid Sci. Technol., 108, 925-935 (2006).
Zhao, Y.Y., Zhao, H.S., Zhao, X., Jia, J., Ma, Q., Zhang, S.C., Zhang, X.R., Chiba, H., Hui, S.P. and Ma, X.X. Identification and quantitation of C=C location isomers of unsaturated fatty acids by epoxidation reaction and tandem mass spectrometry. Anal. Chem., 89, 10270-10278 (2017); DOI.

© References compiled by: William W. Christie
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