Pyrrolidine Derivatives

The following references dealing with mass spectrometry of pyrrolidide derivatives 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.

  • 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).
  • Alborn,H.T., Jones,T.H., Stenhagen,G.S. and Tumlinson,D.J.H. Identification and synthesis of volicitin and related components from beet armyworm oral secretions. J. Chem. Ecol., 26, 203-220 (2000).
  • Andersson,B.A. Mass spectrometry of fatty acid pyrrolidides. Prog. Chem. Fats other Lipids, 16, 279-308 (1978).
  • Andersson,B.A. Pyrrolidides in the structural analysis of lipids by mass spectrometry. Adv. Biochem. Physiol. Plant Lipids, 257-262 (1979).
  • Andersson,B.A. and Bertelsen,O. A study of the wax from the free-flowing preen gland secretion of the Coscoroba swan. Chem. Scripta, 8, 135-139 (1975).
  • Andersson,B.A. and Holman,R.T. Pyrrolidides for mass spectrometric determination of the position of double bonds in monounsaturated fatty acids. Lipids, 9, 185-190 (1974).
  • Andersson,B.A. and Holman,R.T. Mass spectrometric localisation of methylbranching in fatty acids using acylpyrrolidines. Lipids, 10, 716-718 (1975).
  • Andersson,B.A., Christie,W.W. and Holman,R.T. Mass spectrometric determination of positions of double bonds in polyunsaturatd fatty acid pyrrolidides. Lipids, 10, 215-219 (1975).
  • Andersson,B.A., Dinger,F. and Dinh-Nguyen,D. Mass spectrometry studies of stable isotope-labelled carboxylic acid derivatives. IV. Pyrrolidides of vicinal and geminal dideuterated n-octadecanoic acids and the omega trideuterated analogue. Chem. Scripta, 19, 118-121 (1982).
  • Andersson,B.A., Dinger,F. and Dinh-Nguyen,N. Mass spectrometry studies of stable isotope labelled carboxylic acid derivatives. I. Normal chain saturated deuterium and carbon-13 compounds. Chem. Scripta, 8, 200-203 (1975).
  • Andersson,B.A., Dinger,F., Dinh-Nguyen,N. and Raal,A. Mass spectrometry studies of stable isotope-labelled carboxylic acid derivatives. III. Methyl perdeuterio-n-alkanpyrrolidamates. Chem. Scripta, 10, 114-116 (1976).
  • Andersson,B.A., Dinger.F. and Dinh-Nguyen,N. Mass spectrometry studies of stable isotope-labelled carboxylic acid derivatives. II. Normal-chain dideuteriated monoethylenic compounds. Chem. Scripta, 9, 155-157 (1976).
  • Andersson,B.A., Heimermann,W.H. and Holman,R.T. Comparison of pyrrolidides with other amides for the mass spectrometry determination of structure of unsaturated fatty acids. Lipids, 9, 443-449 (1974).
  • Ayanoglu,E., Kurtz,K., Kornprobst,J.M. and Djerassi,C. New natural 2-acetoxy fatty acids using CI and EI mass spectrometry. Lipids, 20, 141-144 (1985).
  • Ayanoglu,E., Popov,S., Kornprobst,J.M., Aboud-Bichara,A. and Djerassi,C. Phospholipid studies of marine organisms. V. New alpha-methoxy acids from Higginsia tethyoides. Lipids, 18, 830-836 (1983).
  • Ayanoglu,E., Walkup,R.D., Sica,D. and Djerassi,C. Phospholipid studies of marine organisms: III. New phospholipid FA from Petrosia ficiformis. Lipids, 17, 617-625 (1982).
  • Barnathan,G., Doumenq,P., Njinkoue,J.-M., Miralles,J., Debitus,C., Levi,C. and Kornprobst,J.-M. Sponge fatty acids 3. Occurrence of series of n-7 monoenoic and iso-5,9 dienoic long-chain fatty acids in the phospholipids of the marine sponge Cinachyrella aff. schulzei Keller. Lipids, 29, 297-303 (1994).
  • Barnathan,G., Kornprobst,J.M., Doumenq,P. and Miralles,J. New unsaturated long-chain fatty acids in the phospholipids from the Axinellida sponges Trikentrion loeve and Pseudaxinella cf. lunaecharta. Lipids, 31, 193-200 (1996).
  • Barnathan,G., Kornprobst,J.M., Doumenq,P., Miralles.J. and Bouryesnault,N. Sponge fatty-acids. 5. Characterization of complete series of 2-hydroxy long-chain fatty-acids in phospholipids of 2 Senegalese marine sponges from the family Suberitidae - Pseudosuberites sp and Suberites massa. J. Nat. Prod., 56, 2104-2113 (1993).
  • Barnathan,G., Miralles,J., Gaydou,E.M., Boury-Esnault,N. and Kornprobst,J.-M. New phospholipid fatty acids from the marine sponge Cinachyrella alloclada Uliczka. Lipids, 27, 779-784 (1992).
  • Barnathan,G., Genin,E., Velosaotsy,N.E., Kornprobst,J.M., Al-Lihaibi,S., Al-Sofyani,A. and Nongonierma,R. Phospholipid fatty acids and sterols of two Cinachyrella sponges from the Saudi Arabian Red Sea: comparison with Cinachyrella species from other origins. Comp. Biochem. Physiol. B, 135, 297-308 (2003).
  • Bertelsen,O. and Dinh-Nguyen,N. Contribution to the studies of the naturally occurring lipids. 1. Uropygial gland wax of the black-necked swan (Cygnus melanocoryphus). Chem. Scripta, 19, 172-175 (1982).
  • Broadwater,J.A., Laundre,B.J. and Fox,B.G. Desaturation of trans-octadecenoyl-acyl carrier protein by stearoyl-acyl carrier protein Delta(9) desaturase. J. Inorganic Biochem., 78, 7-14 (2000).
  • Carballeira,N.M. and Alicea,J. The first naturally occurring alpha-methoxylated branched-chain fatty acids from the phospholipids of Amphimedon complanata. Lipids, 36, 83-87 (2001).
  • Carballeira,N.M. and Emiliano,A. Novel brominated phospholipid fatty acids from the Caribbean sponge Agelas sp. Lipids, 28, 763-766 (1993).
  • Carballeira,N.M. and Lopez,M.R. On the isolation of 2-hydroxydocosanoic and 2-hydroxytricosanoic acids from the marine sponge Arnphimedon compressa. Lipids, 24, 89-91 (1989).
  • Carballeira,N.M. and Medina,J.R. New delta(5,9)-fatty acids in the phospholipids of the sea anemone Stoichactis helianthus. J. Nat. Prod., 57, 1688-1695 (1994).
  • Carballeira,N.M. and Maldonado,L. Identification of 5,9-hexadecadienoic acid in the marine sponge Chondrilla nucula. Lipids, 21, 470-471 (1986).
  • Carballeira,N.M. and Maldonado,L. The phospholipid fatty acids of the marine sponge Xestospongia muta. Lipids, 23, 682-684 (1988).
  • Carballeira,N.M. and Maldonado,M.E. 7-methyl-8-hexadecenoic acid: a novel fatty acid from the marine sponge Desmapsama anchorata. Lipids, 23, 690-693 (1988).
  • Carballeira,N.M. and Maldonado,M.E. New phospholipid fatty acids from the caribbean sponge Ectyoplasia ferox. Lipids. 24, 371-374 (1989).
  • Carballeira,N.M. and Maldonado,M.E. On the isolation of the new fatty acid 6,11-eicosadienoic (20:2) and related 6,11-dienoic acids from the sponge Euryspongia rosea. Lipids, 24, 665-668 (1989).
  • Carballeira,N.M. and Pagan,M. Identification and total synthesis of a novel dimethylated fatty acid from the Caribbean sponge Calyx podatypa. J. Nat. Prod., 63, 666-669 (2000).
  • Carballeira,N.M. and Reyes,E.D. Identification of the new 23-methyl-5,9-pentacosadienoic acid in the sponge Cribrochalina vasculum. Lipids, 25, 69-71 (1990).
  • Carballeira,N.M. and Shalabi,F. Novel brominated phospholipid fatty acids from the Caribbean sponge Petrosia sp. J. Nat. Prod., 56, 739-746 (1993).
  • Carballeira,N.M. and Shalabi,F. Identification of naturally occurring trans,trans 5,9 fatty acids from the sponge Plakortis halichondroides. Lipids, 25, 835-840 (1990).
  • Carballeira,N.M., Cruz,C. and Sostre,A. Identification of the novel 7-methyl-6-octadecenoic acid in Holothuria mexicana. J. Nat. Prod., 59, 1076-1078 (1996).
  • Carballeira,N.M., Cruz,H. and Ayala,N.L. Total synthesis of 2-methoxy-14-methylpentadecanoic acid and the novel 2-methoxy-1 4-methylhexadecanoic acid identified in the sponge Agelas dispar. Lipids, 37, 1033-1037 (2002).
  • Carballeira,N.M., Miranda,C., Lozano,C.M., Nechev,J.T., Ivanova,A., Ilieva,M., Tzvetkova,I. and Stefanov,K. Characterization of novel methyl-branched chain fatty acids from a halophilic Bacillus species. J. Nat. Prod., 64, 256-259 (2001).
  • Carballeira,N.M., Maldonado,L. and Porras,B. Isoprenoid fatty acids from marine sponges. Are sponges selective? Lipids, 22, 767-769 (1987).
  • Carballeira,N.M., Montano,N., Vicente,J. and Rodriguez,A.D. Novel cyclopropane fatty acids from the phospholipids of the Caribbean sponge Pseudospongosorites suberitoides. Lipids, 42, 519-524 (2007).
  • Carballeira,N.M., Oyola,D., Vicente,J. and Rodriguez,A.D. Identification of novel alpha-methoxylated phospholipid fatty acids in the caribbean sponge Erylus goffrilleri. Lipids, 42, 1047-1053 (2007).
  • Carballeira,N.M., Reyes,E.D. and Shalabi,F. Identification of novel iso/anteiso nonacosadienoic acids from the phospholipids of the sponges Chondrosia remiformis and Myrmekioderma styx. J. Nat. Prod., 56, 1850-1855 (1993).
  • Carballeira,N.M., Reyes,E.D., Sostre,A., Rodriguez,A.D., Rodriguez,J.L. and Gonzalez,F.A. Identification of the novel antimicrobial fatty acid (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid in Eunicea succinea. J. Nat. Prod., 60, 502-504 (1997).
  • Carballeira,N.M., Shalabi,F. and Negron,V. 2-Hydroxy fatty acids from marine sponges 2. The phospholipid fatty acids of the Caribbean sponges Verongula gigantean and Aplysina archeri. Lipids, 24, 229-232 (1989).
  • Carballeira,N.M., Shalabi,F. and Maldonado,M.E. Identification of the new 18-hexacosenoic acid in the sponge Thalysias juniperina. Lipids, 25, 235-237 (1990).
  • Carballeira,N.M., Sostre,A. and Rodr?gue,A.D. Phospholipid fatty acid composition of Gorgonians of the Genus Pseudopterogorgia: identification of tetracosapolyenoic acids. Comp. Biochem. Physiol. B, 113, 781-783 (1996).
  • Carballeira,N.M., Sostre,A., Stefanov,K., Popov,S., Kujumgiev,A., Dimitrova-Konaklieva,S., Tosteson,C.G. and Tosteson,T.R. The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix, identification of the novel 9-methyl-10-hexadecenoic acid. Lipids, 32, 1271-1275 (1997).
  • 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. Unusual gas chromatographic properties of fatty acid pyrrolidides. Eur. J. Lipid Sci. Technol., 104, 69-70 (2002).
  • 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., 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).
  • Dasgupta, A., Ayanoglu,E. and Djerassi,C. Phospholipid studies of marine organisms: new branched fatty acids from Strongylophora durissima. Lipids, 19, 768-776 (1984).
  • Dasgupta, A., Ayanoglu,E., Wegmann-Szente,A., Tomer,K.B. and Djerassi,C. Mass spectral behaviour and HPLC of some unusual molecular phospholipid species. Chem. Phys. Lipids, 41, 335-347 (1986).
  • Dasgupta, A., Banerjee,P. and Malik,S. Use of microwave irradiation for rapid transesterification of lipids and accelerated synthesis of fatty acyl pyrrolidides for analysis by GC-MS: study of fatty acid profiles of olive oil, evening primrose oil, fish oils and phospholipids from mango pulp. Chem. Phys. Lipids, 62, 281-291 (1992).
  • Dembitsky, V.M., Rezanka,T., Bychek,I.A. and Shustov,M.V. Identification of fatty acids from Cladonia lichens. Phytochemistry, 30, 4015-4018 (1991).
  • Denis, C., Wielgosz-Collin,G., Breteche,A., Ruiz,N., Rabesaotra,V., Boury-Esnault,N., Kornprobst,J.M. and Barnathan,G. New 17-methyl-13-octadecenoic and 3,16-docosadienoic acids from the sponge Polymastia penicillus. Lipids, 44, 655-663 (2009).
  • Dobson, G. and Christie,W.W. Mass spectrometry of fatty acid derivatives. Eur. J. Lipid Sci. Technol., 104, 36-43 (2002).
  • 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).
  • Duque, C., Cepeda,N. and Martinez,A. The steryl ester and phospholipid fatty acids of the sponge Agelas conifera from the Colombian Caribbean. Lipids, 28, 767-769 (1993).
  • Eagles, J., Fenwick,G.R. and Self,R. Remote group derivatives: limitations on the effectiveness of pyrrolidide derivatives of oxygen-containing fatty acids. Biomed. Mass Spectrom., 6, 462-464 (1979).
  • El Kebir, M.V.O., Barnathan,G., Gaydou,E.M., Siau,Y., and Miralles,J. Fatty acids in liver, muscle and gonad of three tropical rays including non-methylene-interrupted dienoic fatty acids. Lipids, 42, 525-535 (2007).
  • Gensler, W.J. and Marshall,J.P. Structures of mycobacterial bis-cyclopropane mycolates by mass spectrometry. Chem. Phys. Lipids, 19, 128-143 (1977).
  • Gerson, T., Patel,J.J. and Nixon,L.N. Some unusual fatty acids of Rhizobium. Lipids, 10, 134-139 (1975).
  • 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).
  • Hennessy, A.A., Barrett, E., Ross, R.P., Fitzgerald, G.F., Devery, R. and Stanton, C. The production of conjugated a-linolenic, g-linolenic and stearidonic acids by strains of bifidobacteria and propionibacteria. Lipids, 47, 313-327 (2012).
  • Henningson, P.J., Vick,B.A., Bugbee,W.M. and Gudmestad,N.C. Characterization of 12-methyl-cis-4-tetradecenoic acid from Corynebacterium sepedonicum. Lipids, 23, 1086-1088 (1988).
  • Holz, G.G., Beach,D.H., Singh,B.N. and Fish,W.R. Biosynthesis of the novel fatty acid, 17-methyl-cis-9,10-methylene-octadecanoic acid, by the parasitic protozoan, Herpetomonas megaseliae. Lipids, 18, 607-610 (1983).
  • Imbs, A.B. and Latyshev,N.A. New Delta 5 and Delta 4 unsaturated medium-and long-chain fatty acids in the freshwater sponge Baicalospongia bacilifera. Chem. Phys. Lipids, 92, 117-125 (1998).
  • Imbs, A.B. and Rodkina,S.A. Isolation of 2-methyl branched unsaturated very long fatty acids from marine sponge Halichondria panicea and identification of them by GC-MS and NMR. Chem. Phys. Lipids, 129, 173-181 (2004).
  • Imbs, A.B. and Rodkina,S.A. Trans and positional ethylenic bonds in two dominant isomers of eicosapentaenoic acid from the freshwater sponge Baicalospongia bacillifera. Lipids, 40, 963-968 (2005).
  • Imbs, A.B., Demidkova,D.A., Dautova,T.N. and Latyshev,N.A. Fatty acid biomarkers of symbionts and unusual inhibition of tetracosapolyenoic acid biosynthesis in corals (Octocorallia). Lipids, 44, 325-335 (2009).
  • Imbs, A.B., Latyshev,N.A., Zhukova,N.V. and Dautova,T.N. Comparison of fatty acid compositions of azooxanthellate Dendronephthya and zooxanthellate soft coral species. Comp. Biochem. Physiol. B, 148, 314-321 (2007).
  • Iversen, S.A., Cawood,P., Madigan,M.J., Lawson,A.M. and Dormandy,T.L. Identification of a diene conjugated component of human lipid as octadeca-9,11-dienoic acid. FEBS Letts, 171, 320-324 (1984).
  • Kakela,R., Hyvarinen,H. and Vainiotalo,P. Unusual fatty acids in the depot fat of the Canadian beaver (Castor canadensis). Comp. Biochem. Physiol. B, 113, 625-629 (1996).
  • Kangani,C.O. and Kelley,D.E. One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent. Tetrahedron Letts., 46, 8917-8920 (2005).
  • Kangani,C.O., Kelley,D.E. and DeLany,J.P. New method for GC/FID and GC-C-IRMS analysis of plasma free fatty acid concentration and isotopic enrichment. J. Chromatogr. B, 873, 95-101 (2008).
  • Karas, M.A. and Russa, R. New long chain bases in lipophosphonoglycan of Acanthamoeba castellanii. Lipids, 48, 639-650 (2013).
  • Kawaguchi,A., Kobayashi,Y., Ogawa,Y. and Okuda,S. Determination of double bond position in PUFA by mass spectrometry. Chem. Pharm. Bull., 31, 3228-3232 (1983).
  • Kendel, M., Barnathan, G., Fleurence, J., Rabesaotra, V. and Wielgosz-Collin, G. Non-methylene interrupted and hydroxy fatty acids in polar lipids of the alga Grateloupia turuturu over the four seasons. Lipids,48, 535-545 (2013).
  • Klein,R.A. and Schmitz,B. Double bond location in fatty acids; a critical analysis of the feasibility of using specifically deuterated pyrrolidides for mass spectral analysis. Biomed. Environ. Mass Spectrom., 13, 429-438 (1986).
  • Krasikova,I.N., Kapustina,N.V., Isakov,V.V., Dmitrenok,A.S., Dmitrenok,P.S, Gorshkova,N.M. and Solov'eva,T.F. Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119T. Eur. J. Biochem., 271, 2895-2904 (2004).
  • Lam,W.K., Hahn,S., Ayanoglu,E. and Djerassi,C. Phospholipid studies of marine organisms. 22. Structure and biosynthesis of a novel brominated fatty acid from a hymeniacidonid sponge. J. Org. Chem., 54, 3428-3432 (1989).
  • Lankelma,J., Ayanoglu,E. and Djerassi,C. Double-bond location in long-chain PUFA by CI-mass spectrometry. Lipids, 18, 853-858 (1983).
  • Lawson,M.P., Thompson,J.E. and Djerassi,C. Cell membrane localization of long chain C24-C30 fatty acids in two marine Demosponges. Lipids, 23, 741-749 (1988).
  • Litchfield,C., Tyszkiewicz,J. and Dato,V. 5,9,23-triacontatrienoic acid, principal fatty acid of the marine sponge Chondrilla nucula. Lipids, 15, 200-202 (1980).
  • Makarieva,T.N., Santalova,E.A., Gorshkova,I.A., Dmitrenok,A.S., Guzii,A.G., Gorbach,V.I., Svetashev,V.I. and Stonik,V.A. A new cytotoxic fatty acid (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid and the sterols from the far eastern sponge Geodinella robusta. Lipids, 37, 75-80 (2002).
  • Mansour,M.P., Volkman,J.K., Holdsworth,D.G., Jackson,A.E. and Blackburn,S.I. Very-long-chain (C-28) highly unsaturated fatty acids in marine dinoflagellates. Phytochemistry, 50, 541-548 (1999).
  • Martinez,A., Duque,C. and Fujimoto,Y. Novel fatty acid esters of (7E,12E,18R,20Z)-variabilin from the marine sponge Ircinia felix. Lipids, 32, 565-569 (1997).
  • Mayzaud,P. and Ackman,R.G. The 6,9,12,15,18-heneicosapentaenoic acid of seal oil. Lipids, 13, 190-194 (1978).
  • Mazzella,N., Molinet,J., Syakti,A.D., Barriol,A., Dodi,A., Bertrand,J.C. and Doumenq,P. Effects of pure n-alkanes and crude oil on bacterial phospholipid classes and molecular species determined by electrospray ionization mass spectrometry. J. Chromatogr. B, 822, 40-53 (2005).
  • Miralles,J., Barnathan,G., Galonnier,R., Sall,T., Samb,A., Gaydou,E.M. and Kornprobst,J.M. New branched-chain fatty acids from the Senegalese gorgonian Leptogorgia piccola (white and yellow morphs). Lipids, 30, 459-466 (1995).
  • Nishimaki-Mogami,T., Minegishi,K., Takahashi,A., Kawasaki,Y., Kurokawa,Y. and Uchiyama,M. Characterisation of skin surface lipids from the monkey (Macaca fascicularis). Lipids, 23, 869-877 (1988).
  • Njinkoue,J.M., Barnathan,G., Miralles,J., Gaydou,E.M. and Samb,A. Lipids and fatty acids in muscle, liver and skin of three edible fish from the Senegalese coast: Sardinella maderensis, Sardinella aurita and Cephalopholis taeniops. Comp. Biochem. Physiol. B, 131, 395-402 (2002).
  • Ogawa,J., Matsumura,K., Kishino,S., Omura,Y. and Shimizu,S. Conjugated linoleic acid accumulation via 10-hydroxy-12-octadecaenoic acid during microaerobic transformation of linoleic acid by Lactobacillus acidophilus. Appl. Environm. Microbiol., 67, 1246-1252 (2001).
  • 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).
  • Pearce,R.E. and Stillway,L.W. Non-methylene-interrupted and omega4 dienoic fatty acids of the white shrimp Penaeus setiferus. Lipids, 12, 544-549 (1977).
  • Petrzika,M., Engst,W. and Macholz,R. Mass spectrometric structural analysis of fatty acid mixtures from biological material after capillary GC. Nahrung, 35, 491-502 (1991).
  • Quevrain, E., Barnathan, G., Meziane, T., Domart-Coulon, I., Rabesaotra, V. and Bourguet-Kondracki, M.L. New 2-methyl-13-icosenoic acid from the temperate Calcisponge Leuconia johnstoni. Lipids, 47, 345-353 (2012).
  • Rafidinarivo,E., Lanéelle,M.-A., Montrozier,H., Valero-Guillén,P., Astola,J., Luquin,M., Promé,J.-C. and Daffé,M. Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids. J. Lipid Res., 50, 477-490 (2009).
  • Rezanka,T. and Mares,P. Unusual and very long-chain fatty acids produced by Basidiomycetes. J. Chromatogr. A, 409, 390-395 (1987).
  • Rezanka,T., Viden,I., Pokorna,L., Klanova,K. and Podojil,M. Fatty acids of Lactobacillus bulgaricus determined by gas chromatography-mass spectrometry. Folia Microbiol., 28, 470-473 (1983).
  • Rezanka,T., Vokoun,J., Slavicek,J. and Podojil,M. Determination of fatty acids in algae by capillary gas chromatography-mass spectrometry. J. Chromatogr., 268, 71-78 (1983).
  • Rezanka,T., Vyhnalek,O. and Podojil,M. Separation and identification of lipids and fatty acids of the marine alga Fucus vesiculosus by thin-layer chromatography and gas chromatography-mass spectrometry. Folia Microbiol., 33, 309-313 (1988).
  • Rezanka,T. and Votruba,J. Chromatography of very long-chain fatty acids from animal and plant kingdoms. Anal. Chim. Acta, 465, 273-297 (2002).
  • Rezanka,T., Sokolov,M.Y. and Viden,I. Unusual and very-long-chain fatty acids in Desulfotomaculum, a sulfate-reducing bacterium. FEMS Microbiol. Letts, 73, 231-238 (1990).
  • Rod'kina,S.A. Fatty acids from the sponge Tedania dirhaphis. Chem. Nat. Compounds, 41, 289-292 (2005).
  • Rod'kina,S.A. Fatty acids from the Okhotsk sea sponge Forcepia uschakowi. Chem. Nat. Compounds, 43, 515-518 (2007).
  • Rod'kina,S.A., Imbs,A.B. and Krasokhin,V.B. Fatty acids of sponges from the Sea of Okhotsk. Russ. J. Marine Biol., 34, 384-390 (2008).
  • Rod'kina,S.A., Latyshev,N.A. and Imbs,A.B. Fatty acids from the Sea of Japan sponge Halichondria panicea. Russ. J. Bioorg. Chem., 29, 382-386 (2003).
  • Rodriguez,W., Osorno,O., Ramos,F.A., Duque,C. and Zea,S. New fatty acids from Colombian Caribbean Sea sponges. Biochem. System. Ecol., 38, 774-783 (2010).
  • Rontani,J.F. Electron ionization mass spectrometric determination of double bond position in monounsaturated alpha,beta- and beta,gamma-isomeric isoprenoid acids. Rapid Commun. Mass Spectrom., 12, 961-967 (1998).
  • Rontani,J.F., Christodoulou,S. and Koblizek,M. GC-MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria. Lipids, 40, 97-108 (2005).
  • Rontani,J.F., Zabeti,N. and Aubert,C. Double bond migration to methylidene positions during electron ionization mass spectrometry of branched monounsaturated fatty acid derivatives. J. Am. Soc. Mass Spectrom., 20, 1997-2005 (2009).
  • Ruiz,N., Dubois,N., Wielgosz-Collin,G., du Pont,T.R., Berge,J.-P., Pouchus,Y.F. and Barnathan,G. Lipid content and fatty acid composition of a marine-derived Trichoderma longibrachiatum strain cultured by agar surface and submerged fermentations. Process Biochem., 42, 676-680 (2007).
  • Saito,T. and Ochiai,H. Identification of a novel all-cis-5,9,12-heptadecatrienoic acid in the cellular slime mold Polysphondylium pallidum. Lipids, 31, 445-447 (1996).
  • Saito,T. and Ochiai,H. Fatty acid composition of the cellular slime mold Polysphondylium pallidum. Lipids, 33, 327-332 (1998).
  • Satouchi,K. and Saito,K. Separation and determination of oleic and cis-vaccenic acids by gas-liquid chromatography-mass spectrometry using a polar cyanopropylsiloxane liquid phase. Biomed. Mass Spectrom., 6, 144-148 (1979).
  • Shibahara,A., Yamamoto,K., Nakayama,T. and Kajimoto,G. cis-Vaccenic acid in mango pulp lipids. Lipids, 21, 388-394 (1986).
  • Shukla,V.K.S., Clausen,J., Egsgaard,H. and Larsen,E. The content of fat and polyenoic fatty acids in the major food sources of the arctic diet. Localization of double bonds in FA by mass spectrometry of FA pyrrolidides. Fette Seifen Anstrichm., 82, 193-199 (1980).
  • Soltani,M., Metzger,P. and Largeau,C. Effects of hydrocarbon structure on fatty acid, fatty alcohol, and beta-hydroxy acid composition in the hydrocarbon-degrading bacterium Marinobacter hydrocarbonoclasticus. Lipids, 39, 491-505 (2004).
  • Spencer,G.F., Payne-Wahl,K., Plattner,R.D. and Kleiman,R. Lactobacillic and methyl-branched olefinic acids in Byrsocarpus coccineus seed oil. Lipids, 14, 72-74 (1979).
  • Takagi,T. and Itabashi,Y. cis-5-Olefinic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols. Lipids, 17, 716-723 (1982).
  • Takagi,T., Kaneniwa,M. and Itabashi,Y. Fatty acids in crinoidea and ophiuroidea: Occurrence of all-cis-6,9,12,15,18,21-tetracosahexaenoic acid. Lipids, 21, 430-433 (1986).
  • Takayama,K., Quereshi,N. and Schnoes,H.K. Isolation and characterization of the monounsaturated long chain fatty acids of Mycobacterium tuberculosis. Lipids, 13, 575-579 (1978).
  • Taylor,J., Parkes,R.J., Wahle,K.W.J. and Graham,A. The monoenoic FA composition of a marine species of Desulphobulbus grown on lactate. Lipids, 20, 393-397 (1985).
  • Thiel,V., Blumenberg,M., Hefter J., Pape,T., Pomponi,S., Reed,J., Reitner,J., W?rheide,G. and Michaelis,W. A chemical view of the most ancient metazoa - biomarker chemotaxonomy of hexactinellid sponges. Naturwissensch., 89, 60-66 (2002).
  • 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).
  • Tulloch,A.P. Mass spectrometry of pyrrolidides of oxo, hydroxy and trimethylsilyloxy octadecanoic acids. Lipids, 20, 652-663 (1985).
  • Tulloch,A.P. Cutin acids: synthesis and mass spectrometry of methyl 16-hydroxy-7-oxo-, 16-hydroxy -8-oxo-, 16-hydroxy-9-oxo-, 16-hydroxy-10-oxo- and 7,16-, 8,16-, 9,16- and 10,16-dihydroxyhexadecanoates. Lipids, 15, 881-888 (1980).
  • Tvrzicka,E., Rezanka,T., Krijt,J. and Janousek,V. Identification of very-long-chain fatty acids in rat and mouse Harderian gland lipids by capillary gas chromatography-mass spectrometry. J. Chromatogr. B, 431, 231-238 (1988).
  • Usata,N., Kaneniwa,M., Masuda,Y., Yasuhiro Ando,Y. and Iida,H. Fatty acid composition of two species of Japanese freshwater sponges Heterorotula multidentata and Spongilla alba. Fisheries Sci., 68, 236-238 (2002).
  • Valicenti,A.J., Chapman,C.J., Holman,R.T. and Chipault,J.R. Mass spectrometry identification of C20 FA in bovine lens using the pyrrolidide derivative. Lipids, 13, 190-194 (1978).
  • Valicenti,A.J., Heimermann,W.H. and Holman,R.T. Mass spectrometry location of triple bonds in FA and fragmentation mechanisms of N-acylpyrrolidides. J. Org. Chem., 44, 1068-1073 (1979).
  • Vetter,W. and Meister,L. Fragmentation of the chain in the mass spectra of the pyrrolidides of alkylcyclohexanecarboxylic acids. Org. Mass Spectrom., 21, 85-89 (1986).
  • Vetter,W. and Walther,W. The mass spectra of pyrrolidides of some aliphatic-alicyclic carboxylic acids. Monats. Chemie, 106, 203-211 (1975).
  • Vetter,W. and Walther,W. Preparation of pyrrolidides from fatty acids via trimethylsilyl esters for GC-MS analysis. J. Chromatogr. A, 513, 405-407 (1990).
  • Vetter,W. and Walther,W. Pyrrolidides as derivatives for the determination of the fatty acids of triacylglycerols by gas-chromatography. J. Chromatogr. A, 686, 149-154 (1994).
  • Vetter,W., Walther,W. and Vecchi,M. Pyrrolidides as derivatives for structural analysis of aliphatic and alicyclic fatty acids by mass spectrometry. Helv. Chim. Acta, 54, 1599-1605 (1971).
  • Viracaoundin,I., Barnathan,G., Gaydou,E.M. and Aknin,M. Phospholipid FA from Indian Ocean tunicates Eudistoma bituminis and Cystodytes violatinctus. Lipids, 38, 85-88 (2003).
  • Voinov,V.G., Boguslavskiy,V.M. and Elkin,Y.N. Resonance electron-capture for determining double bond and hydroxy group locations in fatty acids. Org. Mass Spectrom., 29, 641-646 (1994).
  • Vyssotski, M., Ryan, J., Lagutin, K., Wong, H., Morgan, X. and Stott, M. A novel fatty acid, 12,17-dimethyloctadecanoic acid, from the extremophile Thermogemmatispora sp (Strain T81). Lipids, 47, 601-611 (2012).
  • Walkup,R.D., Jamieson,G.C., Ratcliff,M.R. and Djerassi,C. Phospholipids of marine organisms II. Phospholipids, phospholipid-bound fatty acids and free sterols of the sponge Aplysina fistularis (Pallas) forma fulva (Pallas). Isolation and structure elucidation of unprecedented branched-chain fatty acids. Lipids, 16, 631-646 (1981).
  • Whittle,E., Cahoon,E.B., Subrahmanyam,S. and Shanklin,J. A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English Ivy) can synthesize 16- and 18-carbon monoene and diene products. J. Biol. Chem., 280, 28169-28176 (2005).
  • Wijekoon,W.M.D., Ayanoglu,E. and Djerassi,C. Phospholipid studies of marine organisms 9. New brominated demospongic acids from the phospholipids of two Petrosia species. Tetrahedron Letts, 25, 3285-3288 (1984).
  • Zabeti,N., Bonin,P., Volkman,J.K., Guasco,S. and Rontan,J.-F. Fatty acid composition of bacterial strains associated with living cells of the haptophyte Emiliania huxleyi. Org. Geochem., 41, 627-636 (2010).
  • Zhang,S., Sakuradani,E. and Shimizu,S. Identification and production of n-8 odd-numbered polyunsaturated fatty acids by a Delta 12 desaturation-defective mutant of Mortierella alpina 1S-4. Lipids, 41, 623-626 (2006).
  • Zhang,S., Sakuradani,E., Ito,K. and Shimizu,S. Identification of a novel bifunctional Delta 12/Delta 15 fatty acid desaturase from a basidiomycete, Coprinus cinereus TD#822-2. FEBS Letts, 581, 315-319 (2007).
  • Zhukova,N.V. Lipid classes and fatty acid composition of the tropical nudibranch mollusks Chromodoris sp. and Phyllidia coelestis. Lipids, 42, 1169-1175 (2007).

Updated February 5, 2014