3-Pyridylcarbinol ('picolinyl') Esters

The widely used term 'picolinyl ester' is inaccurate and should now be avoided. The correct trivial name is ‘nicotinyl’ esters, but all dubiety is removed if they are given the more systematic name ‘3-pyridylcarbinol’ (picolinyl alcohol is in fact 2-pyridylcarbinol). The following references dealing with mass spectrometry of 3-pyridylcarbinol esters of fatty acids have been collected as part of our regular literature searches for research purposes. The list is as comprehensive as we can manage but may not be exhaustive. References are listed alphabetically according to the surname of the first author, but not necessarily chronologically for a given author.

  • Adkisson,H.D., Risener,F.S., Zarrinkar,P.P., Walla,M.D., Christie,W.W. and Wuthier,R.E. Unique fatty acid composition of normal cartilage: discovery of high levels of n-9 eicosatrienoic acid and low levels of n-6 polyunsaturated fatty acids. FASEB J., 5, 344-353 (1991).
  • Akesson-Nilsson,G. and Wesen,C. Structural characterization of 5,6-dichlorotetradecanoic acid, an isolated metabolite of 9,10-dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry. J. Mass Spectrom., 39, 1313-1320 (2004).
  • Altabe,S.G., Aguilar,P., Caballero,G.M. and de Mendoza,D. The Bacillus subtilis acyl lipid desaturase is a 5 desaturase. J. Bact., 185, 3228-3231 (2003).
  • Ando,Y., Kawabata,Y., Narukawa,K. and Ota,T. Demospongic acids of the marine sponge Halichondria panicea from the coast of Hokkaido, Japan. Fisheries Sci., 64, 136-139 (1998).
  • Augustyn,O.P.H., Ferreira,D. and Kock,J.L.F. Differentiation between yeast species, and strains within a species, by cellular fatty acid analysis. 4. Saccharomyces-sensu-stricto, Hanseniaspora, Saccharomycodes and Wickerhamiella. System. Appl. Microbiol., 14, 324-334 (1991).
  • Augustyn,O.P.H., Kock,J.L.F. and Ferreira,D. Differentiation between yeast species, and strains within a species, by cellular fatty acid analysis. 5. A feasible technique? System. Appl. Microbiol., 15, 105-115 (1992).
  • Balazy,M. and Nies,A.S. Characterization of epoxides of polyunsaturated fatty acids by mass spectrometry via 3-pyridinylmethyl esters. Biomed. Environ. Mass Spectrom., 18, 328-336 (1989).
  • Berdeaux,O., Gregoire,S., Fournier,C., Christie,W.W., Lambelet,P. and Sebedio,J.L. Detection of lactobacillic acid in low erucic rapeseed oil - A note of caution when quantifying cyclic fatty acid monomers in vegetable oils. Chem. Phys. Lipids, 163, 698-702 (2010).
  • Berdeaux,O., Juaneda,P. and Sebedio,J.L. Analysis of conjugated and trans fatty acids after derivatization. Analusis, 26, M45-M51 (1998).
  • Bertelsen,O. and Dinh-Nguyen,N. Structure elucidation of alkyl-branched chain aliphatic alcohols and FA by mass spectrometry of their respective alkyl nicotinate and picolinyl carboxylate derivatives. Fette Seifen Anstrichm., 87, 336-342 (1985).
  • Brechany,E.Y. and Christie,W.W. Identification of the unsaturated oxo fatty acids in cheese. J. Dairy Res., 61, 111-115 (1994).
  • Brechany,E.Y. and Christie,W.W. Identification of the saturated oxo fatty acids in cheese. J. Dairy Res., 59, 57-64 (1992).
  • Budge,S.M. and Parrish,C.C. FA determination in cold water marine samples. Lipids, 38, 781-791 (2003).
  • Carballeira,N.M. and Reyes,M. Identification of a new 6-bromo-5,9-eicosadienoic acid from the anemone Condylactis gigantea and the zoanthid Palythoa caribaeorum. J. Nat. Prod., 58, 1689-1694 (1995).
  • Carreto,L., Moore,E., Nobre,M.F., Wait,R., Riley,P.W., Sharp,R.J. and Dacosta,M.S. Rubrobacter xylanophilus sp.nov.: a new thermophilic species isolated from a thermally polluted effluent. Int. J. System. Bact., 46, 460-465 (1996).
  • Choma,A. and Komaniecka,I. Straight and branched (omega-1)-hydroxylated very long chain fatty acids are components of Bradyrhizobium lipid A. Acta Biochim. Polon., 58, 51-57 (2011).
  • Christie, W.W. The chromatographic analysis of lipids. In: 'The Lipid Handbook - 3rd edition', pp. 426-455 (edited by F.D. Gunstone, J.L. Harwood and A. Dijkstra, Chapman & Hall, London) (2007).
  • Christie, W.W. HPLC and gas chromatography-mass spectrometry in the analysis of fatty acids in 'Fats for the Future', pp. 335-344 (edited by R.C. Cambie, Ellis Horwood Ltd, Chichester). (1989).
  • Christie, W.W. Mass spectrometry of fatty acids with methylene-interrupted ene-yne systems. Chem. Phys. Lipids, 94, 35-41 (1998).
  • Christie, W.W. Mass spectrometry of fatty acid derivatives. In: Applications of Modern Mass Spectrometry in Plant Science Research (Proc. Phytochemical Society of Europe), pp. 195-209 (edited by R.P. Newton and T.J. Walton, Clarendon Press, Oxford). (1996).
  • Christie, W.W. Structural analysis of fatty acids. In: Advances in Lipid Methodology - Four, pp. 119-169 (edited by W.W. Christie, Oily Press, Dundee) (1997).
  • Christie, W.W. Gas chromatography mass spectrometry methods for structural analysis of fatty acids. Lipids, 33, 343-353 (1998).
  • Christie, W.W. Recent developments in high-performance liquid and gas chromatography of lipids. Rev. Franc. Corps Gras, 38, 155-160 (1991).
  • Christie, W.W. 13-Phenyltridec-9-enoic and 15-phenylpentadec-9-enoic acids in Arum maculatum seed oil. Eur. J. Lipid Sci. Technol., 105, 779-780 (2003).
  • Christie, W.W. and Han, X. Lipid Analysis - Isolation, Separation, Identification and Lipidomic Analysis (4th edition), 446 pages (Oily Press, Bridgwater, U.K. and Woodhead Publishing Ltd, Cambridge, U.K.) (2010) - Woodhead Publishing Ltd.
  • Christie, W.W. and Stefanov,K. Separation of picolinyl ester derivatives of fatty acids by high-performance liquid chromatography for identification by mass spectrometry. J. Chromatogr. A, 392, 259-265 (1987).
  • Christie, W.W., Brechany,E.Y. and Holman,R.T. Mass spectra of the picolinyl esters of isomeric mono- and dienoic fatty acids. Lipids, 22, 224-228 (1987).
  • Christie, W.W., Brechany,E.Y. and Lie Ken Jie,M.S.F. Mass spectra of the picolinyl ester derivatives of some isomeric dimethylene-interrupted octadecadiynoic acids. Chem. Phys. Lipids, 46, 225-229 (1988).
  • Christie, W.W., Brechany,E.Y. and Shukla,V.K.S. Analysis of seed oils containing cyclopentenyl fatty acids by combined chromatographic procedures. Lipids, 24, 116-120 (1989).
  • Christie, W.W., Brechany,E.Y. and Stefanov,K. Silver ion high-performance liquid chromatography and gas chromatography-mass spectrometry in the analysis of complex fatty acid mixtures: application to marine invertebrates. Chem. Phys. Lipids, 46, 127-136 (1988).
  • Christie, W.W., Brechany,E.Y., Gunstone,F.D., Lie Ken Jie,M.S.F. and Holman,R.T. Mass spectra of the picolinyl esters of some non-methylene-interrupted octadecadienoic acids. Lipids, 22, 664-666 (1987).
  • Christie, W.W., Brechany,E.Y., Johnson,S.B. and Holman,R.T. A comparison of pyrrolidide and picolinyl ester derivatives for the identification of fatty acids in natural samples by gas chromatography-mass spectrometry. Lipids, 21, 657-661 (1986).
  • Christie, W.W. and Dobson,G. Formation of cyclic fatty acids during the frying process. Eur. J. Lipid Sci. Technol., 102, 515-520 (2000).
  • Christie, W.W., Brechany,E.Y., Lie Ken Jie,M.S.F. and Bakare,O. MS characterization of picolinyl and methyl ester derivatives of isomeric thia fatty acids. Biol. Mass Spectrom., 20, 629-635 (1991).
  • Christie, W.W., Brechany,E.Y., Lie Ken Jie,M.S.F. and Wong,C.F. Mass spectrometry of derivatives of isomeric allenic fatty acids. Biol. Mass Spectrom., 21, 267-270 (1992).
  • Christie, W.W., Brechany,E.Y., Marekov,I.N., Stefanov,K.L. and Andreev,S.N. The fatty acids of the sponge Hymeniacidon sanguinea from the Black Sea. Comp. Biochem. Physiol. B, 109, 245-252 (1994).
  • Christie, W.W., Brechany,E.Y., Sebedio,J.L. and Le Quere,J.L. Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic monoenoic acids formed in frying oils. Chem. Phys. Lipids, 66, 143-153 (1993).
  • Christie, W.W., Brechany,E.Y., Stefanov,K. and Popov,S. The fatty acids of the sponge Dysidea fragilis from the Black Sea. Lipids, 27, 640-644 (1992).
  • Christie, W.W., Hamilton,J.T.G. and Harper,D.B. Mass spectrometry of fluorinated fatty acids in the seed oil of Dichapetalum toxicarium. Chem. Phys. Lipids, 97, 41-47 (1998).
  • Cox, A.D. and Wilkinson,S.G. Polar lipids and fatty acids of Pseudomonas cepacia. Biochim. Biophys. Acta, 1001, 60-67 (1989).
  • Dembitsky, V.M., Rezanka,T. and Shubina,E.E. Unusual hydroxy fatty acids from some higher fungi. Phytochemistry, 34, 1057-1059 (1993).
  • Demirbuker, M., Blomberg,L.G., Olsson,N.U., Bergqvist,M., Herslof,B.G. and Jacobs,F.A. Characterization of triacylglycerols in the seeds of Aquilegia vulgaris by chromatographic and mass spectrometric methods. Lipids, 27, 436-441 (1992).
  • Destaillats, F. and Angers,P. One-step methodology for the synthesis of FA picolinyl esters from intact lipids. J. Am. Oil Chem. Soc., 79, 253-256 (2002).
  • Destaillats, F., Trottier,J.P., Galvez,J.M.G. and Angers,P. Analysis of alpha-linolenic acid biohydrogenation intermediates in milk fat with emphasis on conjugated linolenic acids. J. Dairy Sci., 88, 3231-3239 (2005).
  • Destaillats, F., Wolff,R.L. and Angers,P. Saturated and unsaturated anteiso-C-19 acids in the seed lipids from Hesperopeuce mertensiana (Pinaceae). Lipids, 37, 325-328 (2002).
  • Deterding, L.J. and Gross,M.L. Fast-atom-bombardment and tandem mass spectrometry for determining structures of fatty acids as their picolinyl esters. Anal. Chim. Acta, 200, 431-445 (1987).
  • Dobson, G. Cyclic fatty acids: qualitative and quantitative analysis. In: 'Lipid Analysis in Oils and Fats', pp. 136-180 (edited by R.J. Hamilton, Blackie, London) (1998).
  • Dobson, G. and Christie,W.W. Structural analysis of fatty acids by mass spectrometry of picolinyl esters and dimethyloxazoline derivatives. Trends Anal. Chem., 15, 130-137 (1996).
  • Dobson, G. and Christie,W.W. Mass spectrometry of fatty acid derivatives. Eur. J. Lipid Sci. Technol., 104, 36-43 (2002).
  • Dobson, G., Christie,W.W. and Sebedio,J.L. Saturated bicyclic fatty acids formed in heated sunflower oils. Chem. Phys. Lipids, 87, 137-147 (1997).
  • Dobson, G., Christie,W.W. and Sebedio,J.L. The nature of cyclic fatty acids formed in heated vegetable oils. Grasas Aceites, 47, 26-33 (1996).
  • Dobson, G., Christie,W.W. and Sebedio,J.L. Monocyclic saturated fatty acids formed from oleic acid in heated sunflower oils. Chem. Phys. Lipids, 82, 101-110 (1996).
  • Dobson, G., Christie,W.W., Brechany,E.Y., Sebedio,J.L. and Le Quere,J.L. Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic dienoic fatty acids formed in frying oils. Chem. Phys. Lipids, 75, 171-182 (1995).
  • Dowd, M.K. Identification of the unsaturated heptadecyl fatty acids in the seed oils of Thespesia populnea and Gossypium hirsutum. J. Am. Oil Chem. Soc., 89, 1599-1609 (2012).
  • Dubois, N., Barnathan,G., Gouygou,J.P. and Berge,J.P. Gas chromatographic behavior of fatty acid derivatives for mass spectrometry on low-polarity capillary columns. Eur. J. Lipid Sci. Technol., 111, 688-697 (2009).
  • Dubois, N., Barthomeuf,C. and Berge,J.P. Convenient preparation of picolinyl derivatives from fatty acid esters. Eur. J. Lipid Sci. Technol., 108, 28-32 (2006).
  • Grav, H.J., Asiedu,D.K. and Berge,R.K., Gas chromatographic measurement of 3-thia and 4-thia fatty acids incorporated into various classes of rat liver lipids during feeding experiments. J. Chromatogr. B, 658, 1-10 (1994).
  • G?mez-Cort?s, P., Tyburczy,C., Brenna,J.T., Ju?rez,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).
  • Griffiths, G., Brechany,E.Y., Jackson,F.M., Christie,W.W., Stymne,S. and Stobart,A.K. Distribution and biosynthesis of stearidonic acid in leaves of Borago officinalis. Phytochemistry, 43, 381-386 (1996).
  • Hamilton, J.T.G. and Christie,W.W. Mechanisms for ion formation during the electron impact-mass spectrometry of picolinyl ester and 4,4-dimethyloxazoline derivatives of fatty acids. Chem. Phys. Lipids, 105, 93-104 (2000).
  • Hammann, S., Tillmann, U., Schroder, M. and Vetter, W. Profiling the fatty acids from a strain of the microalgae Alexandrium tamarense by means of high-speed counter-current chromatography and gas chromatography coupled with mass spectrometry. J. Chromatogr. A, 1312, 93-103 (2013).
  • Harvey, D.J. Picolinyl esters as derivatives for the structural determination of long chain branched and unsaturated fatty acids. Biomed. Mass Spectrom., 9, 33-38 (1982).
  • Harvey, D.J. Picolinyl derivatives for the structural determination of fatty acids by mass spectrometry. Applications to polyenoic acids, hydroxy acids, di-acids and related compounds. Biomed. Mass Spectrom., 11, 340-347 (1984).
  • Harvey, D.J. Picolinyl derivatives for the characterization of cyclopropane fatty acids by mass spectrometry. Biomed. Mass Spectrom., 11, 187-192 (1984).
  • Harvey, D.J. Identification of long-chain fatty acids and alcohols from human cerumen by the use of picolinyl and nicotinate esters. Biomed. Environ. Mass Spectrom., 18, 719-723 (1989).
  • Harvey, D.J. Identification by gas chromatography-mass spectrometry of long-chain fatty acids and alcohols from Meibomian glands using picolinyl and nicotinate derivatives. Biomed. Chromatogr., 3, 251-254 (1989).
  • Harvey, D.J. Long-chain fatty acids and alcohols from gerbil meibomian glands. J. Chromatogr. B, 494, 23-30 (1989).
  • Harvey, D.J. Identification by GC and MS of lipids from the rat Harderian gland. J. Chromatogr. B, 565, 27-34 (1991).
  • Harvey, D.J. Lipids from the guinea pig harderian gland - use of picolinyl and other pyridine-containing derivatives to investigate the structures of novel branched-chain fatty acids and glycerol ethers. Biol. Mass Spectrom., 20, 61-69 (1991).
  • Harvey, D.J. Mass spectrometry of picolinyl and other nitrogen-containing derivatives of fatty acids. In: 'Advances in Lipid Methodology - One' (edited by W.W. Christie, Oily Press, Ayr), pp. 19-80 (1992).
  • Harvey, D.J. Identification and quantification of lipids from rabbit harderian glands by GC-MS. Biomed. Chromatogr., 5, 143-147 (1991).
  • Harvey, D.J. Picolinyl esters for the structural determination of fatty acids by GC/MS. Mol. Biotech., 10, 251-260 (1998).
  • Harvey, D.J. Pyridine-containing derivatives for the structural elucidation of the alkyl chains of lipids by MS and a comparison with the spectra of related heterocyclic derivatives. Spectros. Int. J., 8, 211-244 (1990).
  • Harvey, D.J. and Tiffany,J.M. Identification of meibomian gland lipids by gas chromatography-mass spectrometry: application to the meibomian lipids of the mouse. J. Chromatogr. A, 301, 173-188 (1984).
  • Harvey, D.J., Tiffany,J.M., Duerden,J.M., Pandher,K.S. and Mengher,L.S. Identification by combined gas chromatography-mass spectrometry of constituent long-chain fatty acids and alcohols from the meibomian glands of the rat and a comparison with human meibomian glands. J. Chromatogr. B, 414, 253-263 (1987).
  • Hastings, N., Agaba,M., Tocher,D.R., Leaver,M.J., Dick,J.R., Sargent,J.R. and Teale,A.J. A vertebrate fatty acid desaturase with 5 and 6 activities. Proc. Natl. Acad. Sci. USA, 98, 14304-14309 (2001).
  • Hauff, S. and Vetter,W. Exploring the fatty acids of vernix caseosa in form of their methyl esters by off-line coupling of non-aqueous reversed phase high performance liquid chromatography and gas chromatography coupled to mass spectrometry. J. Chromatogr. A, 1217, 8270-8278 (2010).
  • Hauff, S., Rilfors,L., Hottinger,G. and Vetter,W. Structure and absolute configuration of an unsaturated anteiso fatty acid from Bacillus megaterium. J. Chromatogr. A, 1217, 1683-1687 (2010).
  • Hierro, M.T.G., Robertson,G., Christie,W.W. and Joh,Y.-G. The fatty acid composition of the seeds of Ginkgo biloba. J. Am. Oil Chem. Soc., 73, 575-579 (1996).
  • Holmback, J., Karlsson,A.A. and Arnoldsson,K.C. Characterization of N-acylphosphatidylethanolamine and acylphosphatidylglycerol in oats. Lipids, 36, 153-165 (2001).
  • Honda, A., Yamashita,K., Hara,T., Ikegami,T., Miyazaki,T., Shirai,M., Xu,G.R., Numazawa,M. and Matsuzaki,Y. Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS. J. Lipid Res., 50, 350-357 (2009).
  • Honda, A., Yamashita,K., Miyazaki,H., Shirai,M., Ikegami,T., Xu,G., Numazawa,M., Hara,T. and Matsuzaki,Y. Highly sensitive analysis of sterol profiles in human serum by LC-ESI-MS/MS. J. Lipid Res., 49, 2063-2073 (2008).
  • Joh,Y.-G., Brechany,E.Y. and Christie,W.W. Characterization of wax esters in the roe oil of amber fish, Seriola aureovittata. J. Am. Oil Chem. Soc., 72, 707-713 (1995).
  • Joh,Y.G., Elenkov,I.J., Stefanov,K.L., Popov,S.S., Dobson,G. and Christie,W.W. Novel di-, tri-, and tetraenoic fatty acids with bis-methylene-interrupted double-bond systems from the sponge Haliclona cinerea. Lipids, 32, 13-17 (1997).
  • Joh,Y.-G., Kim,S.-J. and Christie,W.W. The structure of the triacylglycerols containing punicic acid in the seed oil of Trichosanthes kirilowii. J. Am. Oil Chem. Soc., 72, 1037-1042 (1995).
  • Johnson,D.W., Beckman,K., Fellenberg,A.J., Robinson,B.S. and Poulos,A. Monoenoic fatty acids in human brain lipids: isomer identification and distribution. Lipids, 27, 177-180 (1992).
  • Kawashima, H. Unusual minor nonmethylene-interrupted di-, tri-, and tetraenoic fatty acids in limpet gonads. Lipids, 40, 627-630 (2005).
  • Kawashima, H. and Ohnishi,M. Occurrence of novel nonmethylene-interrupted C-24 polyenoic fatty acids in female gonad lipids of the limpet Cellana grata. Biosci. Biotechn. Biochem., 70, 2575-2578 (2006).
  • Kawashima, H. and Ohnishi, M. Novel heneicosadienoic and tricosadienoic acid isomers in ovaries of marine Archaeogastropods. Lipids, 47, 827-833 (2012).
  • Kawashima, H., Ohnishi,M., Ogawa,S. and Matsui,K. Unusual fatty acid isomers of triacylglycerols and polar lipids in female limpet gonads of Cellana grata. Lipids, 43, 559-567 (2008).
  • Kim,S.J. and Joh,Y.G. Occurrence of cis-4-tetradecenoic acid in the oils of kernels of Lindera erythrocarpa seeds, as a major component. Food Sci. Biotechnol., 15, 107-111 (2006).
  • Knothe,G., Rashid,U., Yusup,S. and Anwar,F. Fatty acids of Thespesia populnea: mass spectrometry of picolinyl esters of cyclopropene fatty acids. Eur. J. Lipid Sci. Technol., 113, 980–984 (2011).
  • Kurkiewicz,S., Dzierzewicz,Z., Wilczok,T. and Dworzanski,J.P. GC/MS determination of fatty acid picolinyl esters by direct curie-point pyrolysis of whole bacterial cells. J. Am. Soc. Mass Spectrom., 14, 58-62 (2003).
  • Leth,T. Chemometric analysis of mass spectra of cis and trans fatty acid picolinyl esters. Z. Lebensm.-Unters. Forsch., 205, 111-115 (1997).
  • Libert,R., Van Hoof,F., Thillaye,M., Vincent,M.F., Nassogne,M.C., de Hoffmann,E. and Schanck,A. Identification of undescribed medium-chain acylcarnitines present in urine of patients with propionic and methylmalonic acidemias. Clin. Chim. Acta, 295, 87-96 (2000).
  • Libert,R., Van Hoof,F., Thillaye,M., Vincent,M.F., Nassogne,M.C., Stroobant,V., de Hoffmann,E. and Schanck,A. Identification of new medium-chain acylcarnitines present in urine of a patient with medium-chain acyl-CoA dehydrogenase deficiency. J. Inher. Metab. Dis., 22, 9-18 (1999).
  • Libert,R., Van Hoof,F., Thillaye,M., Vincent,M.F., Nassogne,M.C., Stroobant,V., de Hoffmann,E. and Schanck,A. Identification of new medium-chain acylcarnitines present in normal human urine. Anal. Biochem., 251, 196-205 (1997).
  • Lie Ken Jie,M.S.F. and Cheung,Y.K. Mass spectral studies on methyl and picolinyl ester derivatives of isomeric selena fatty acids. Biol. Mass Spectrom., 21, 505-508 (1992).
  • Lie Ken Jie,M.S.F. and Choi,Y.C. Gas chromatography-mass spectrometry of the picolinyl ester derivatives of deuterated acetylenic fatty acids. J. Chromatogr. A, 625, 271-276 (1992).
  • Lie Ken Jie,M.S.F. and Choi,Y.C. Mass spectral determination of deuterium-labelled picolinyl fatty esters in the determination of double bond position. J. Am. Oil Chem. Soc., 69, 1245-1247 (1992).
  • Lie Ken Jie,M.S.F. and Choi,Y.C. GC-MS of saturated and unsaturated even and odd-number long chain fatty acids by analysis of the picolinyl esters. Application to a Chinese medicinial seed (Cuscuta semen) seed oil. J. Int. Fed. Clin. Chem., 3, 121-128 (1991).
  • Lie Ken Jie,M.S.F., Cheung,Y.K., Chau,S.H., Christie,W.W. and Brechany,E.Y. Mass spectra of the picolinyl ester derivatives of some conjugated diacetylenic acids. Chem. Phys. Lipids, 63, 65-68 (1992).
  • Lie Ken Jie,M.S.F., Choi,C.Y.C., Berger,A. and Berger,R.G. Re-examination of the fatty acid composition of Biota orientalis seed oil by gas chromatography-mass spectrometry of the picolinyl ester derivatives. J. Chromatogr. A, 543, 257-261 (1991).
  • Lie Ken Jie,M.S.F., Lam,C.N.W., Ho,J.C.M. and Lau,M.M.L. Epoxidation of a conjugated linoleic acid isomer. Eur. J. Lipid Sci. Technol., 105, 391-396 (2003).
  • Mitei,Y.C., Ngila,J.C., Yeboah,S.O., Wessjohann,L. and Schmidt,J. NMR, GC-MS and ESI-FTICR-MS profiling of fatty acids and triacylglycerols in some botswana seed oils. J. Am. Oil Chem. Soc., 85, 1021-1032 (2008).
  • Moule,A.L. and Wilkinson,S.G. Polar lipids, fatty acids and isoprenoid quinones of Alteromonas putrefaciens (Shewalla putrefaciens). System. Appl. Microbiol., 9, 192-198 (1987).
  • Nagao,T., Watanabe,Y., Hiraoka,K., Kishimoto,N., Fujita,T. and Shimada,Y. Microbial conversion of vegetable oil to rare unsaturated fatty acids and fatty alcohols by an Aeromonas hydrophila isolate. J. Am. Oil Chem. Soc., 86, 1189-1197 (2009).
  • Nechev,J., Christie,W.W., Robaina,R., de Diego,F., Popov,S. and Stefanov,K. Chemical composition of the sponge Hymeniacidon sanguinea from the Canary Islands. Comp. Biochem. Physiol. A, 137, 365-374 (2004).
  • Nechev,J., Christie,W.W., Robaina,R., de Diego,F., Popov,S. and Stefanov,K. Lipid composition of the sponge Verongia aerophoba from the Canary Islands. Eur. J. Lipid Sci. Technol., 104, 800-807 (2002).
  • Nechev,J., Christie,W.W., Robaina,R., de Diego,F.M., Ivanova,A., Popov,S. and Stefanov,K. Chemical composition of the sponge Chondrosia reniformis from the Canary Islands. Hydrobiologia, 489, 91-98 (2002).
  • Nikolova-Damyanova,B., Christie,W.W. and Herslof,B. The structure of the triacylglycerols of meadowfoam oil. J. Am. Oil Chem. Soc., 67, 503-507 (1990).
  • Oku,H., Mimura,K., Tokitsu,Y., Onaga,K., Iwasaki,H. and Chinen,I. Biased distribution of the branched-chain fatty acids in ceramides of vernix caseosa. Lipids, 35, 373-381 (2000).
  • Oursel,D., Loutelier-Bourhis,C., Orange,N., Chevalier,S., Norris,V. and Lange,C.M. Identification and relative quantification of fatty acids in Escherichia coli membranes by gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom., 21, 3229-3233 (2007).
  • Pedneault,K., Angers,P., Gosselin,A. and Tweddell,R.J. Fatty acid composition of lipids from mushrooms belonging to the family Boletaceae. Mycol. Res., 110, 1179-1183 (2006).
  • Ratnayake,W.M.N. and Pelletier,G. Positional and geometrical isomers of linoleic acid in partially hydrogenated oils. J. Am. Oil Chem. Soc., 69, 95-105 (1992).
  • Ratnayake,W.M.N., Olsson,B. and Ackman,R.G. Novel branched-chain fatty acids in certain fish oils. Lipids, 24, 630-637 (1989).
  • Rezanka,T. Branched and very long-chain dicarboxylic acids from Equisetum species. Phytochemistry, 47, 1539-1543 (1998).
  • Rezanka,T. Analysis of very long chain fatty acids by HPLC and GC-MS with chemical ionization. LC-GC Int., 3 (10), 46-49 (1990).
  • Rezanka,T. Identification of very long polyenoic acids as picolinyl esters by Ag+ ion-exchange HPLC, reversed-phase HPLC and GC-MS. J. Chromatogr. A, 513, 344-348 (1990).
  • 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 Dembitsky,V.M. Identification of unusual cyclopropane monounsaturated fatty acids from the deep-water lake invertebrate Acanthogammarus grewingkii. Comp. Biochem. Physiol. B, 109, 407-413 (1994).
  • Rezanka,T. and Dembitsky,V.M. Isoprenoid fatty acids from fresh-water sponges. J. Nat. Prod., 56, 1898-1904 (1993).
  • Rezanka,T. and Dembitsky,V.M. Multibranched polyunsaturated and very-long-chain fatty acids of freshwater Israeli sponges. J. Nat. Prod., 65, 709-713 (2002).
  • 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 Sigler,K. Identification of very long chain fatty acids from sugar cane wax by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy. Phytochemistry, 67, 916-923 (2006).
  • Rezanka,T., Nedbalova,L. and Sigler,K. Unusual medium-chain polyunsaturated fatty acids from the snow alga Chloromonas brevispina. Microbiol. Res., 163, 373-379 (2008).
  • 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).
  • Rezanka,T., Nedbalova,L., Elster,J., Cajthaml,T. and Sigler,K. Very-long-chain iso and anteiso branched fatty acids in N-acylphosphatidylethanolamines from a natural cyanobacterial mat of Calothrix sp. Phytochemistry, 70, 655-663 (2009).
  • Rezanka,T., Sigler,K. and Dembitsky,V.M. Syriacin, a novel unusual sulfated ceramide glycoside from the freshwater sponge Ephydatia syriaca (Porifera, Demospongiae, Spongillidae). Tetrahedron, 62, 5937-5943 (2006).
  • Rezanka,T., Siristova,L., Melzoch,K. and Sigler,K. Identification of (S)-11-cycloheptyl-4-methylundecanoic acid in acylphosphatidylglycerol from Alicyclobacillus acidoterrestris. Chem. Phys. Lipids, 159, 104-113 (2009).
  • Rowe, N.J., Tunstall,J., Galbraith,L. and Wilkinson,S.G. Lipid composition and taxonomy of [Pseudomonas] echinoides: transfer to the genus Sphingomonas. Microbiology, 146, 3007-3012 (2000).
  • Rubino, F.M. and Zecca,L. Triple quadrupole tandem MS study of the 3-picolinyl esters of fatty acids. Org. Mass Spectrom., 27, 1240-1247 (1992).
  • Rubino, F.M. and Zecca,L. Application of triple quadrupole tandem MS to the analysis of pyridine-containing derivatives of long-chain acids and alcohols. J. Chromatogr. B, 579, 1-12 (1992).
  • Santana-Marques, M.G.O., Ferrer-Correia,A.J.V., Caldwell,K.A. and Gross,M.L. Charge-remote fragmentation and the 2-step elimination of alkanols from fast-atom bombardment-desorbed (M+H)+, (M+Cat)+ and (M-H)- ions of aromatic beta-hydroxyoximes. J. Am. Soc. Mass Spectrom., 4, 819-827 (1993).
  • Schroder, M. and Vetter, W. Detection of 430 fatty acid methyl esters from a transesterified butter sample. J. Am. Oil Chem. Soc., 90, 771-790 (2013).
  • Sebedio, J.L., Juaneda,P., Dobson,G., Ramilison,I., Martin,J.C., Chardigny,J.M. and Christie,W.W. Metabolites of conjugated isomers of linoleic acid (CLA) in the rat. Biochim. Biophys. Acta, 1345, 5-10 (1997).
  • Siristova, L., Luhovy,R., Sigler,K. and Rezanka,T. Biosynthesis of omega-alicyclic fatty acids induced by cyclic precursors and change of membrane fluidity in thermophilic bacteria Geobacillus stearothermophilus and Meiothermus ruber. Extremophiles, 15, 423-429 (2011).
  • Sittig, M. and Hirsch,P. Chemotaxonomic investigation of budding and or hyphal bacteria. System. Appl. Microbiol., 15, 209-222 (1992).
  • Sledzinski, T., Mika, A., Stepnowski, P., Proczko-Markuszewska, M., Kaska, L., Stefaniak, T. and Swierczynski, J. Identification of cyclopropaneoctanoic acid 2-hexyl in human adipose tissue and serum.. Lipids, 48, 839-848 (2013).
  • Spitzer, V. Gas chromatography/(electron impact)mass spectrometry analysis of conjugated linoleic acid (CLA) using different derivatization techniques. In: Advances in Conjugated Linoleic Acid Research, Vol. 1. (ed. M.P. Yurawecz, M.M. Mossoba, J.K.G. Kramer, M.W. Pariza and G.J. Nelson, AOCS Press, Champaign) pp. 110-125 (1999).
  • Spitzer, V., Marx,F., Maia,J.G.S. and Pfeilsticker,K. The mass spectra of the picolinyl ester derivatives of malvalic and sterculic acid. Fat Sci. Technol., 96, 395-396 (1994).
  • Spitzer, V., Marx,F., Maia,J.G.S. and Pfeilsticker,K. Curupira tefeensis II. Occurrence of acetylenic fatty acids. Fat Sci. Technol., 93, 169-174 (1991).
  • Stefanov, K., Konaklieva,M., Brechany,E.Y. and Christie,W.W. Fatty acid composition of some algae from the Black Sea. Phytochemistry, 27, 3495-3497 (1988).
  • Stefanov, K., Seizova,K., Brechany,E.Y. and Christie,W.W. An unusual fatty acid composition for a fresh-water mussel, Unio tumidus, from Bulgaria. J. Nat. Prod., 55, 979-981 (1992).
  • Stefanov, K.L., Christie,W.W., Brechany,E.Y., Popov,S.S., and Andreev,S.N. Lipid composition of the red and green forms of Actinia equina from the Black Sea. Comp. Biochem. Physiol. B, 103, 687-690 (1992).
  • Tsevegsuren, N., Fujimoto,K., Christie,W.W. and Endo,Y. Occurrence of a novel cis, cis, cis-octadeca-3,9,12-trienoic (Z,Z,Z-octadeca-3,9,12-trienoic) acid in Chrysanthemum (Tanacetum) zawadskii Herb. (Compositae) seed oil. Lipids, 38, 573-578 (2003).
  • Tsydendambaev, V.D., Christie,W.W., Brechany,E.Y. and Vereshchagin,A.G. Identification of unusual fatty acids of four alpine plant species from the Pamirs. Phytochemistry, 65, 2685-2703 (2004).
  • Van Boven, M., Holser,R.A., Cokelaere,M., Decuypere,E., Govaerts,C. and Lemey,J. Characterization of triglycerides isolated from jojoba oil. J. Am. Oil Chem. Soc., 77, 1325-1328 (2000).
  • Vetter, W. and Wegner,I. Quantitative determination of isostearic acid isomers in skin creams by GC-MS-SIM. Chromatographia, 70, 157-164 (2009).
  • Wait,R. and Hudson,M.J. The use of picolinyl esters for the characterization of microbial lipids: application to the unsaturated and cyclopropane fatty acids of Campylobacter species. Lett. Appl. Microbiol., 1, 95-99 (1985).
  • Wellburn, A.R., Robinson,D.C., Thomson,A. and Leith,I.D. Influence of episodes of summer O-3 on delta(5) and delta(9) fatty-acids in autumnal lipids of Norway spruce [Picea abies (L) Karst]. New Phytologist, 127, 355-361 (1994).
  • Wetzel, D.L. and Reynolds,J.E. Definitive identification of fatty acid constituents in marine mammal tissues. Canad. J. Fish. Aquatic Sci., 61, 554-560 (2004).
  • Wing, D.R., Harvey,D.J., La Droitte,P., Robinson,K. and Belcher,S. Examination of the esterified fatty acids from mouse erythrocyte and synaptosomal membrane phospholipids and their distribution between various phospholipid types. J. Chromatogr. A, 368, 103-111 (1986).
  • Wolff, R.L. and Christie,W.W. Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis 5-olefinic acids. Eur. J. Lipid Sci. Technol., 104, 234-244 (2002).
  • Wolff, R.L., Christie,W.W. and Coakley,D. Bishomopinolenic (7,11,14-20:3) acid in Pinaceae seed oils. J. Am. Oil Chem. Soc., 74, 1583-1586 (1997).
  • Wolff, R.L., Christie,W.W. and Coakley,D. The unusual occurrence of 14-methylhexadecanoic acid in pinaceae seed oils among plants. Lipids, 32, 971-973 (1997).
  • Wolff, R.L., Christie,W.W. and Marpeau,A.M. Reinvestigation of the polymethylene-interrupted 18:2 and 20:2 acids of Ginkgo biloba seed lipids. J. Am. Oil Chem. Soc., 76, 273-276 (1999).
  • Wolff, R.L., Christie,W.W., Pedrono,F. and Marpeau,A.M. Arachidonic, eicosapentaenoic, and biosynthetically related fatty acids in the seed lipids from a primitive gymnosperm, Agathis robusta. Lipids, 34, 1083-1097 (1999).
  • Wolff, R.L., Christie,W.W., Pedrono,F., Marpeau,A.M., Tsevegsuren,N., Aitzetmuller,K. and Gunstone,F.D. Delta 5-olefinic acids in the seed lipids from four Ephedra species and their distribution between the alpha and beta positions of triacylglycerols. Characteristics common to Coniferophytes and Cycadophytes. Lipids, 34, 855-864 (1999).
  • Wretsenjo, I., Svensson,L. and Christie,W.W. Gas chromatographic-mass spectrometric identification of fatty acids in borage oil using the picolinyl ester derivatives. J. Chromatogr. A, 521, 89-98 (1990).
  • Wu, P.F., Grav,H.J., Horn,R. and Bremer,J . Effects of chain length and sulfur position of thia fatty acids on their incorporation into phospholipids in 7800 c1 hepatoma cells and isolated rat hepatocytes, and their effects on fatty acid composition of phospholipids. Biochem. Pharmacol., 51, 751-758 (1996).
  • Yang, S., Minkler,P. and Hoppel,C. Cis-3,4-methylene-heptanoylcarnitine: Characterization and verification of the C8:1 acylcarnitine in human urine. J. Chromatogr. B, 857, 251-258 (2007).
  • Yang, S., Minkler,P., Hoppel,C. and Tserng,K.-Y. Picolinyl ester fragmentation mechanism studies with application to the identification of acylcarnitine acyl groups following transesterification. J. Am. Soc. Mass Spectrom., 17, 1620-1628 (2006).
  • Yu, C.M., Curtis,J.M., Wright,J.L.C., Ayer,S.W. and Fathiafshar,Z.R. An unusual fatty acid and its glyceride from the marine fungus Microsphaeropis olivacea. Canad. J. Chem., 74, 730-735 (1996).

 

Updated February 5, 2014