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Fatty Acids: Introduction

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Biogenesis of Fatty Acids, Lipids and Membranes

Part of the book series: Handbook of Hydrocarbon and Lipid Microbiology ((HHLM))

Abstract

Fatty acids have been part of the biosphere from its beginning, providing a high calorie foodstuff in metabolism, the structural basis of membranes , an important class of intra-and extracellular signaling molecules , and many other functions. They are a diverse group of molecules, although most are linear aliphatic molecules with a terminal carboxylic acid. Here, we provide an overview of their nomenclature, their synthesis, and their biodegradation and an outline of some of the major classes of fatty acids.

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References

  • Alonso L, Fraga MJ, Juárez M (2000) Determination of trans fatty acids and fatty acid profiles in margarines marketed in Spain. J Am Oil Chem Soc 77:131–136

    Article  CAS  Google Scholar 

  • Amirta R, Fujimori K, Shirai N, Honda Y, Watanabe T (2003) Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora. Chem Phys Lipid 126:121–131

    Article  CAS  Google Scholar 

  • Aries E, Doumenq P, Artaud J, Acquaviva M, Bertrand JC (2001) Effects of petroleum hydrocarbons on the phospholipid fatty acid composition of a consortium composed of marine hydrocarbon-degrading bacteria. Org Geochem 32:891–903

    Article  CAS  Google Scholar 

  • Bagby MO, Smith CR Jr, Wolff IA (1965) Laballenic acid. A new allenic acid from Leonotis nepetaefolia seed oil 1. J Org Chem 30:4227–4229

    Article  CAS  Google Scholar 

  • Banni S, Angioni E, Murru E, Carta G, Paola Melis M, Bauman D, Dong Y, Ip C (2001) Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland. Nutr Cancer 41:91–97

    Article  CAS  PubMed  Google Scholar 

  • Barford RA, Herb SF, Luddy FE, Magidman P, Riemenschneider RW (1963) Alcoholysis of Vernonia anthelmintica seed oil and isolation of methyl epoxyoleate. J Am Oil Chem Soc 40:136–138

    Article  CAS  Google Scholar 

  • Barkan D, Liu Z, Sacchettini JC, Glickman MS (2009) Mycolic acid cyclopropanation is essential for viability, drug resistance, and cell wall integrity of Mycobacterium tuberculosis. Chem Biol 16:499–509

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bellou S, Triantaphyllidou IE, Aggeli D, Elazzazy AM, Baeshen MN, Aggelis G (2016) Microbial oils as food additives: recent approaches for improving microbial oil production and its polyunsaturated fatty acid content. Curr Opin Biotechnol 37:24–35

    Article  CAS  PubMed  Google Scholar 

  • Benoit B, Plaisancie P, Geloen A, Estienne M, Debard C, Meugnier E, Loizon E, Daira P, Bodennec J, Cousin O, Vidal H, Laugerette F, Michalski MC (2014) Pasture v. standard dairy cream in high-fat diet-fed mice: improved metabolic outcomes and stronger intestinal barrier. Br J Nutr 112:520–535

    CAS  PubMed  Google Scholar 

  • Berge AFL (2008) How the ideology of low fat conquered America. J Hist Med Allied Sci 63:139–177

    Article  PubMed  Google Scholar 

  • Blanchet C, Lucas M, Julien P, Morin R, Gingras S, Dewailly E (2005) Fatty acid composition of wild and farmed Atlantic salmon (Salmo salar) and rainbow trout (Oncorhynchus mykiss). Lipids 40:529–531

    Article  CAS  PubMed  Google Scholar 

  • Blasbalg TL, Hibbeln JR, Ramsden CE, Majchrzak SF, Rawlings RR (2011) Changes in consumption of omega-3 and omega-6 fatty acids in the United States during the 20th century. Am J Clin Nutr 93:950–962

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Brune T, Haas K (2011) Equisetum species show uniform epicuticular wax structures but diverse composition patterns. AoB Plants 2011:plr009

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Bucas G, Saliot A (2002) Sea transport of animal and vegetable oils and its environmental consequences. Mar Pollut Bull 44:1388–1396

    Article  CAS  PubMed  Google Scholar 

  • Bu'Lock JD (1964) Polyacetylenes and related compounds in nature. Prog Org Chem 6:86–134

    Google Scholar 

  • Burr GO, Burr MM, Miller ES (1932) On the fatty acids essential in nutrition. 3. J Biol Chem 97:1–9

    CAS  Google Scholar 

  • Campbell JW, Morgan-Kiss RM, Cronan JE Jr (2003) A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway. Mol Microbiol 47:793–805

    Article  CAS  PubMed  Google Scholar 

  • Carballeira NM, Reyes M, Sostre A, Huang H, Verhagen MF, Adams MW (1997) Unusual fatty acid compositions of the hyperthermophilic archaeon Pyrococcus furiosus and the bacterium Thermotoga maritima. J Bacteriol 179:2766–2768

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Cathey HM, Steffens GL, Stuart NW, Zimmerman RH (1966) Chemical pruning of plants. Science 153:1382–1383

    Article  CAS  PubMed  Google Scholar 

  • Celmer WD, Solomons IA (1953) Mycomycin. III. The structure of mycomycin, an antibiotic containing allene, diacetylene and cis, trans-diene groupings. J Am Oil Chem Soc 75:1372–1376

    Article  CAS  Google Scholar 

  • Chan M, Himes RH, Akagi JM (1971) Fatty acid composition of thermophilic, mesophilic, and psychrophilic Clostridia. J Bacteriol 106:876–881

    CAS  PubMed  PubMed Central  Google Scholar 

  • Chrysan MM (2005) Margarines and spreads. Food emulsifiers and their applications. In: Shahidi F (ed) Bailey’s industrial oil and fat products, 6th edn. Wiley, New York, pp 307–326

    Google Scholar 

  • Conlon MA, Bird AR (2015) The impact of diet and lifestyle on gut microbiota and human health. Nutrients 7(1):17–44

    Article  CAS  Google Scholar 

  • Corley TA (1988) A history of the Burmah Oil Company: 1924–66. Heinemann, London

    Google Scholar 

  • Curran KA, Leavitt JM, Karim AS, Alper HS (2013) Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metabol Eng 15:55–66

    Article  CAS  Google Scholar 

  • Da Silva MS, Julien P, Pérusse L, Vohl MC, Rudkowska I (2015) Natural rumen-derived trans fatty acids are associated with metabolic markers of cardiac health. Lipids 50:873–882

    Article  CAS  PubMed  Google Scholar 

  • Daley CA, Abbott A, Doyle PS, Nader GA, Larson S (2010) A review of fatty acid profiles and antioxidant content in grass-fed and grain-fed beef. Nutr J 10:1

    Google Scholar 

  • Das S, Castillo C, Stevens T (2001) Phospholipid remodeling/generation in Giardia: the role of the lands cycle. Trends Parasitol 17:316–319

    Article  CAS  PubMed  Google Scholar 

  • Davis JB (1964) Microbial incorporation of fatty acids derived from n-alkanes into glycerides and waxes. Appl Microbiol 12:210–214

    CAS  PubMed  PubMed Central  Google Scholar 

  • Dayan FE, Cantrell CL, Duke SO (2009) Natural products in crop protection. Bioorg Med Chem 17:4022–4034

    Article  CAS  PubMed  Google Scholar 

  • de Batlle J, Sauleda J, Balcells E, Gomez FP, Mendez M, Rodriguez E, Barreiro E, Ferrer JJ, Romieu I, Gea J, Anto JM, Garcia-Aymerich J (2012) Association between omega3 and omega6 fatty acid intakes and serum inflammatory markers in COPD. J Nutr Biochem 23:817–821

    Article  PubMed  CAS  Google Scholar 

  • de Souza RJ, Mente A, Maroleanu A, Cozma AI, Ha V, Kishibe T, Uleryk E, Budylowski P, Schünemann H, Beyene J, Anand SS (2015) Intake of saturated and trans unsaturated fatty acids and risk of all cause mortality, cardiovascular disease, and type 2 diabetes: systematic review and meta-analysis of observational studies. Brit Med J 351:h3978

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Dear RE, Pattison FL (1963) Toxic fluorine compounds. XVIII. 1 the synthesis of the toxic principle of Dichapetalum toxicarium (18-Fluoro-cis-9-octadecenoic acid) and related ω-fluoro unsaturated acids. J Am Chem Soc 85:622–626

    Article  CAS  Google Scholar 

  • Dembitsky VM, Srebnik M (2002) Natural halogenated fatty acids: their analogues and derivatives. Prog Lipid Res 41:315–367

    Article  CAS  PubMed  Google Scholar 

  • Dubertret G, Mirshahi A, Mirshahi M, Gerard-Hirne C, Tremolieres A (1994) Evidence from in vivo manipulations of lipid composition in mutants that the delta 3-trans-hexadecenoic acid-containing phosphatidylglycerol is involved in the biogenesis of the light-harvesting chlorophyll a/b-protein complex of Chlamydomonas reinhardtii. Eur J Biochem 226:473–482

    Article  CAS  PubMed  Google Scholar 

  • Dyer JM, Chapital DC, Kuan JC, Mullen RT, Turner C, McKeon TA, Pepperman AB (2002) Molecular analysis of a bifunctional fatty acid conjugase/desaturase from tung. Implications for the evolution of plant fatty acid diversity. Plant Physiol 130:2027–2038

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • English J, Bonner J, Haagen-Smit AJ (1939) Structure and synthesis of a plant wound hormone. Science 90:329

    Article  CAS  PubMed  Google Scholar 

  • Freedman B, Bagby MO (1989) Heats of combustion of fatty esters and triglycerides. J Am Oil Chem Soc 66:1601–1605

    Article  CAS  Google Scholar 

  • Fujita Y, Matsuoka H, Hirooka K (2007) Regulation of fatty acid metabolism in bacteria. Mol Microbiol 66:829–839

    Article  CAS  PubMed  Google Scholar 

  • Gao J, Ajjawi I, Manoli A, Sawin A, Xu C, Froehlich JE, Last RL, Benning C (2009) FATTY ACID DESATURASE4 of Arabidopsis encodes a protein distinct from characterized fatty acid desaturases. Plant J 60:832–839

    Article  CAS  PubMed  Google Scholar 

  • Geiger O (2010) Lipids and Legionella virulence. In: Timmis KN (ed) Handbook of hydrocarbon and lipid microbiology, 1st edn. Springer, Berlin, pp 3195–3202

    Chapter  Google Scholar 

  • Ghosh S, Molcan E, DeCoffe D, Dai C, Gibson DL (2013) Diets rich in n-6 PUFA induce intestinal microbial dysbiosis in aged mice. Br J Nutr 110:515–523

    Article  CAS  PubMed  Google Scholar 

  • Gibellini F, Smith TK (2010) The Kennedy pathway – de novo synthesis of phosphatidylethanolamine and phosphatidylcholine. IUBMB Life 62:414–428

    Article  CAS  PubMed  Google Scholar 

  • Glass RL, Krick TP, Sand DM, Rahn CH, Schlenk H (1975) Furanoid fatty acids from fish lipids. Lipids 10:695–702

    Article  CAS  PubMed  Google Scholar 

  • Green AG (1986) A mutant genotype of flax (Linum usitatissimum L.) containing very low levels of linolenic acid in its seed oil. Can J Plant Sci 66:499–503

    Article  CAS  Google Scholar 

  • Grogan DW, Cronan JE (1997) Cyclopropane ring formation in membrane lipids of bacteria. Microbiol Mol Biol Rev 61:429–441

    CAS  PubMed  PubMed Central  Google Scholar 

  • Hammond EG, Lundberg WO (1953) A methyl docosahexaenoate: its isolation and characterization. J Am Oil Chem Soc 30:438–441

    Article  CAS  Google Scholar 

  • Hashimoto M, Orikasa Y, Hayashi H, Watanabe K, Yoshida K, Okuyama H (2015) Occurrence of trans monounsaturated and polyunsaturated fatty acids in Colwellia psychrerythraea strain 34H. J Basic Microbiol 55:838–845

    Article  CAS  PubMed  Google Scholar 

  • Heipieper HJ, Meinhardt F, Segura A (2003) The cis–trans isomerase of unsaturated fatty acids in Pseudomonas and Vibrio: biochemistry, molecular biology and physiological function of a unique stress adaptive mechanism. FEMS Microbiol Letts 229:1–7

    Article  CAS  Google Scholar 

  • Herrera LJ, Brand S, Santos A, Nohara LL, Harrison J, Norcross NR, Thompson S, Smith V, Lema C, Varela-Ramirez A, Gilbert IH (2016) Validation of N-myristoyltransferase as potential chemotherapeutic target in mammal-dwelling stages of Trypanosoma cruzi. PLoS Negl Trop Dis 10:e0004540

    Article  PubMed  PubMed Central  Google Scholar 

  • Hiltunen JK, Mursula AM, Rottensteiner H, Wierenga RK, Kastaniotis AJ, Gurvitz A (2003) The biochemistry of peroxisomal beta-oxidation in the yeast Saccharomyces cerevisiae. FEMS Microbiol Rev 27:35–64

    Article  CAS  PubMed  Google Scholar 

  • Hofmann K, Lucas RA (1950) The chemical nature of a unique fatty acid. J Am Chem Soc 72:4328–4329

    Article  CAS  Google Scholar 

  • Ishige T, Tani A, Sakai Y, Kato N (2003) Wax ester production by bacteria. Curr Opin Microbiol 6:244–250

    Article  CAS  PubMed  Google Scholar 

  • Janssen HJ, Steinbuchel A (2014) Fatty acid synthesis in Escherichia coli and its applications towards the production of fatty acid based biofuels. Biotechnol Biofuels 7:7

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Jimenez PN, Koch G, Thompson JA, Xavier KB, Cool RH, Quax WJ (2012) The multiple signaling systems regulating virulence in Pseudomonas aeruginosa. Microbiol Mol Biol Rev 76:46–65

    Article  CAS  PubMed  Google Scholar 

  • Johnson EA, Burdon KL (1947) Mycomycin-a new antibiotic produced by a moldlike actinomycete active against the bacilli of human tuberculosis. J Bacteriol 54:281

    CAS  PubMed  Google Scholar 

  • Jump DB, Tripathy S, Depner CM (2013) Fatty acid–regulated transcription factors in the liver. Ann Rev Nutr 33:249–269

    Article  CAS  Google Scholar 

  • Junker F, Ramos JL (1999) Involvement of the cis/trans isomerase Cti in solvent resistance of Pseudomonas putida DOT-T1E. J Bacteriol 181:5693–5700

    CAS  PubMed  PubMed Central  Google Scholar 

  • Jusoh M, Loh SH, Chuah TS, Aziz A, San Cha T (2015) Elucidating the role of jasmonic acid in oil accumulation, fatty acid composition and gene expression in Chlorella vulgaris (Trebouxiophyceae) during early stationary growth phase. Algal Res 9:14–20

    Article  Google Scholar 

  • Kaneda T (1991) Iso- and anteiso-fatty acids in bacteria: biosynthesis, function, and taxonomic significance. Microbiol Rev 55:288–302

    CAS  PubMed  PubMed Central  Google Scholar 

  • Kass LR, Bloch K (1967) On the enzymatic synthesis of unsaturated fatty acids in Escherichia coli. Proc Natl Acad Sci U S A 58:1168–1173

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Keweloh H, Heipieper HJ (1996) Trans unsaturated fatty acids in bacteria. Lipids 31:129–137

    Article  CAS  PubMed  Google Scholar 

  • Kim JJ, Miura R (2004) Acyl-CoA dehydrogenases and acyl-CoA oxidases. Structural basis for mechanistic similarities and differences. Eur J Biochem 271:483–493

    Article  CAS  PubMed  Google Scholar 

  • Kirpich IA, Petrosino J, Ajami N, Feng W, Wang Y, Liu Y, Beier JI, Barve SS, Yin X, Wei X, Zhang X, McClain CJ (2016) Saturated and unsaturated dietary fats differentially modulate ethanol-induced changes in gut microbiome and metabolome in a mouse model of alcoholic liver disease. Am J Pathol 186:765–776

    Article  CAS  PubMed  Google Scholar 

  • Kleber ME, Delgado GE, Lorkowski S, März W, von Schacky C (2015) Trans fatty acids and mortality in patients referred for coronary angiography: the Ludwigshafen risk and cardiovascular health study. Eur Heart J 2015:ehv446

    Google Scholar 

  • Klein RA, Hazlewood GP, Kemp P, Dawson RM (1979) A new series of long-chain dicarboxylic acids with vicinal dimethyl branching found as major components of the lipids of Butyrivibrio spp. Biochem J 183:691–700

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Knothe G, Dunn RO (2009) A comprehensive evaluation of the melting points of fatty acids and esters determined by differential scanning calorimetry. J Am Oil Chem Soc 86:843–856

    Article  CAS  Google Scholar 

  • Kuo J, Khosla C (2014) The initiation ketosynthase (FabH) is the sole rate-limiting enzyme of the fatty acid synthase of Synechococcus sp. PCC 7002. Metab Eng 22:53–59

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lands WEM (1960) Metabolism of glycerolipids. II. The enzymatic acylation of lysolecithin. J Biol Chem 235:2233–2237

    CAS  PubMed  Google Scholar 

  • Lang I, Hodac L, Friedl T, Feussner I (2011) Fatty acid profiles and their distribution patterns in microalgae: a comprehensive analysis of more than 2000 strains from the SAG culture collection. BMC Plant Biol 11:124

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lazzari M, Chiantore O (1999) Drying and oxidative degradation of linseed oil. Polymer Deg Stabil 65:303–313

    Article  CAS  Google Scholar 

  • Linder ME, Deschenes RJ (2007) Palmitoylation: policing protein stability and traffic. Nat Rev Mol Cell Biol 8:74–84

    Article  CAS  PubMed  Google Scholar 

  • Longo N, Frigeni M, Pasquali M (2016) Carnitine transport and fatty acid oxidation. Biochim Biophys Acta 1863:2422–2435

    Article  CAS  PubMed  Google Scholar 

  • Lynen F (1964) The pathway from “activated acetic acid” to the terpenes and fatty acids. Proc Roy Karol Inst 1964:103–138

    Google Scholar 

  • Lynen F (1969) Yeast fatty acid synthase. Meth Enzymol 14:17–33

    Article  CAS  Google Scholar 

  • Maggio-Hall LA, Keller NP (2004) Mitochondrial beta-oxidation in Aspergillus nidulans. Mol Microbiol 54:1173–1185

    Article  CAS  PubMed  Google Scholar 

  • Makula R, Finnerty WR (1968) Microbial assimilation of hydrocarbons I. Fatty acids derived from normal alkanes. J Bacteriol 95:2102–2107

    CAS  PubMed  PubMed Central  Google Scholar 

  • McDaniel J, Askew W, Bennett D, Mihalopoulos J, Anantharaman S, Fjeldstad AS, Rule DC, Nanjee NM, Harris RA, Richardson RS (2013) Bison meat has a lower atherogenic risk than beef in healthy men. Nutr Res 33:293–302

    Article  CAS  PubMed  Google Scholar 

  • McMurrough I, Rose AH (1973) Effects of temperature variation on the fatty acid composition of a psychrophilic Candida species. J Bacteriol 114:451–452

    CAS  PubMed  PubMed Central  Google Scholar 

  • Meesapyodsuk D, Qiu X (2008) An oleate hydroxylase from the fungus Claviceps purpurea: cloning, functional analysis, and expression in Arabidopsis. Plant Physiol 147:1325–1333

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Metz JG, Roessler P, Facciotti D, Levering C, Dittrich F, Lassner M, Valentine R, Lardizabal K, Domergue F, Yamada A, Yazawa K, Knauf V, Browse J (2001) Production of polyunsaturated fatty acids by polyketide synthases in both prokaryotes and eukaryotes. Science 293:290–293

    Article  CAS  PubMed  Google Scholar 

  • Metzger JO (2009) Fats and oils as renewable feedstock for chemistry. Eur J Lipid Sci Technol 111:865–876

    Article  CAS  Google Scholar 

  • Montgomery MK, Osborne B, Brown SH, Small L, Mitchell TW, Cooney GJ, Turner N (2013) Contrasting metabolic effects of medium- versus long-chain fatty acids in skeletal muscle. J Lipid Res 54:3322–3333

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Morita N, Shibahara A, Yamamoto K, Shinkai K, Kajimoto G, Okuyama H (1993) Evidence for cis-trans isomerization of a double bond in the fatty acids of the psychrophilic bacterium Vibrio sp. strain ABE-1. J Bacteriol 175:916–918

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mudge S (1997) Can vegetable oils outlast mineral oils in the marine environment? Mar Pollut Bull 34:213

    Article  CAS  Google Scholar 

  • Mustonen AM, Käkelä R, Nieminen P (2007) Different fatty acid composition in central and peripheral adipose tissues of the American mink (Mustela vison). Comp Biochem Physiol A 147:903–910

    Article  CAS  Google Scholar 

  • Nada MA, Abdel-Aleem S, Schulz H (1995) On the rate-limiting step in the beta-oxidation of polyunsaturated fatty acids in the heart. Biochim Biophys Acta 1255:244–250

    Article  PubMed  Google Scholar 

  • Nagy B, Bitz SM (1963) Long-chain fatty acids from the Orgueil meteorite. Arch of Biochem Biophys 101:240–248

    Article  CAS  Google Scholar 

  • Nakamura MT, Yudell BE, Loor JJ (2014) Regulation of energy metabolism by long-chain fatty acids. Prog Lipid Res 53:124–144

    Article  CAS  PubMed  Google Scholar 

  • Nudda A, McGuire MA, Battacone G, Pulina G (2005) Seasonal variation in conjugated linoleic acid and vaccenic acid in milk fat of sheep and its transfer to cheese and ricotta. J Dairy Sci 88:1311–1319

    Article  CAS  PubMed  Google Scholar 

  • Ohnishi M, Thompson GA Jr (1991) Biosynthesis of the unique trans-delta 3-hexadecenoic acid component of chloroplast phosphatidylglycerol: evidence concerning its site and mechanism of formation. Arch Biochem Biophys 288:591–599

    Article  CAS  PubMed  Google Scholar 

  • Oshima MI, Ariga T (1975) Omega-cyclohexyl fatty acids in acidophilic thermophilic bacteria. Studies on their presence, structure, and biosynthesis using precursors labeled with stable isotopes and radioisotopes. J Biol Chem 250:6963–6968

    CAS  PubMed  Google Scholar 

  • Pérez AC, Goossens A (2013) Jasmonate signaling: a copycat of auxin signaling? Plant Cell Environ 36:2071–2084

    Article  PubMed  CAS  Google Scholar 

  • Poirier Y, Antonenkov VD, Glumoff T, Hiltunen JK (2006) Peroxisomal beta-oxidation-a metabolic pathway with multiple functions. Biochim Biophys Acta 1763:1413–1426

    Article  CAS  PubMed  Google Scholar 

  • Pond CM, Mattacks CA, Colby RH, Ramsay MA (1992) The anatomy, chemical composition, and metabolism of adipose tissue in wild polar bears (Ursus maritimus). Can J Zoo 70:326–341

    Article  CAS  Google Scholar 

  • Qureshi N, Takayama K, Jordi HC, Schnoes HK (1978) Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra. J Biol Chem 253:5411–5417

    CAS  PubMed  Google Scholar 

  • Riekhof WR, Sears BB, Benning C (2005) Annotation of genes involved in glycerolipid biosynthesis in Chlamydomonas reinhardtii: discovery of the betaine lipid synthase BTA1Cr. Eukaryot Cell 4:242–252

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Rontani JF, Christodoulou S, Koblizek M (2005) GC-MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria. Lipids 40:97–108

    Article  CAS  PubMed  Google Scholar 

  • Rossi M, Buzzini P, Cordisco L, Amaretti A, Sala M, Raimondi S, Ponzoni C, Pagnoni UM, Matteuzzi D (2009) Growth, lipid accumulation, and fatty acid composition in obligate psychrophilic, facultative psychrophilic, and mesophilic yeasts. FEMS Microbiol Ecol 69:363–372

    Article  CAS  PubMed  Google Scholar 

  • Royce LA, Liu P, Stebbins MJ, Hanson BC, Jarboe LR (2013) The damaging effects of short chain fatty acids on Escherichia coli membranes. Appl Microbiol Biotechnol 97:8317–8327

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ruxton CH, Reed SC, Simpson MJ, Millington KJ (2004) The health benefits of omega-3 polyunsaturated fatty acids: a review of the evidence. J Hum Nutr Diet 17:449–459

    Article  CAS  PubMed  Google Scholar 

  • Ryan VH, Primiani CT, Rao JS, Ahn K, Rapoport SI (2014) Coordination of gene expression of arachidonic and docosahexaenoic acid cascade. PLOS One 9:e100858

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Schonfeld P, Wojtczak L (2016) Short- and medium-chain fatty acids in energy metabolism: the cellular perspective. J Lipid Res 57:943–954

    Article  PubMed  CAS  Google Scholar 

  • Schröder M, Vetter W (2013) Detection of 430 fatty acid methyl esters from a transesterified butter sample. J Am Oil Chem Soc 90:771–790

    Article  CAS  Google Scholar 

  • Schweizer E, Hofmann J (2004) Microbial type I fatty acid synthases (FAS): major players in a network of cellular FAS systems. Microbiol Mol Biol Rev 68:501–517

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Segré D, Ben-Eli D, Deamer DW, Lancet D (2001) The lipid world. Orig Life Evol B 31:119–145

    Article  Google Scholar 

  • Shah J (2009) Plants under attack: systemic signals in defence. Curr Opin Plant Biol 12:459–464

    Article  CAS  PubMed  Google Scholar 

  • Shirasaka N, Nishi K, Shimizu S (1995) Occurrence of a furan fatty acid in marine bacteria. Biochim Biophys Acta 1258:225–227

    Article  PubMed  Google Scholar 

  • Silva SA, Salvador AF, Cavaleiro AJ, Pereira MA, Stams AJ, Alves MM, Sousa DZ (2016) Toxicity of long chain fatty acids towards acetate conversion by Methanosaeta concilii and Methanosarcina mazei. Microb Biotechnol 9:514–518

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Simopoulos AP (2008) The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases. Exp Biol Med 233:674–688

    Article  CAS  Google Scholar 

  • Smith RJ, Grula EA (1982) Toxic components on the larval surface of the corn earworm (Heliothis zea) and their effects on germination and growth of Beauveria bassiana. J Invert Pathol 39:15–22

    Article  CAS  Google Scholar 

  • Song TJ, Cho HJ, Chang Y, Choi K, Jung AR, Youn M, Shin MJ, Kim YJ (2015) Low plasma proportion of omega 3-polyunsaturated fatty acids predicts poor outcome in acute non-cardiogenic ischemic stroke patients. J Stroke 17:168–176

    Article  PubMed  PubMed Central  Google Scholar 

  • Sztajer H, Wagner G, Schmnid RD (1993) Bacterial short-chain acyl-CoA oxidase: production, purification and characterization. Appl Microbiol Biotechnol 39:708–713

    Article  CAS  Google Scholar 

  • Takayama K, Wang C, Besra GS (2005) Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin Microbiol Rev 18:81–101

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Taleshi MS, Edmonds JS, Goessler W, Ruiz-Chancho MJ, Raber G, Jensen KB, Francesconi KA (2010) Arsenic-containing lipids are natural constituents of sashimi tuna. Environ Sci Technol 44:1478–1483

    Article  CAS  PubMed  Google Scholar 

  • Tehlivets O, Scheuringer K, Kohlwein SD (2007) Fatty acid synthesis and elongation in yeast. Biochim Biophys Acta 1771:255–270

    Article  CAS  PubMed  Google Scholar 

  • Teoh ML, Chu WL, Marchant H, Phang SM (2004) Influence of culture temperature on the growth, biochemical composition and fatty acid profiles of six Antarctic microalgae. J Appl Phycol 16:421–430

    Article  CAS  Google Scholar 

  • Toomey RE, Wakil SJ (1966) Studies on the mechanism of fatty acid synthesis. XVI. Preparation and general properties of acyl-malonyl acyl carrier protein-condensing enzyme from Escherichia coli. J Biol Chem 241:1159–1165

    CAS  PubMed  Google Scholar 

  • Vagelos PR, Alberts AW, Majerus PW (1969) Mechanism of saturated fatty acid biosynthesis in Escherichia coli. Meth Enzymol 14:39–43

    Article  CAS  Google Scholar 

  • Vieler A, Wu G, Tsai CH, Bullard B, Cornish AJ, Harvey C, Reca IB, Thornburg C, Achawanantakun R, Buehl CJ, Campbell MS, Cavalier D, Childs KL, Clark TJ, Deshpande R, Erickson E, Armenia Ferguson A, Handee W, Kong Q, Li X, Liu B, Lundback S, Peng C, Roston RL, Sanjaya SJP, Terbush A, Warakanont J, Zauner S, Farre EM, Hegg EL, Jiang N, Kuo MH, Lu Y, Niyogi KK, Ohlrogge J, Osteryoung KW, Shachar-Hill Y, Sears BB, Sun Y, Takahashi H, Yandell M, Shiu SH, Benning C (2012) Genome, functional gene annotation, and nuclear transformation of the heterokont oleaginous alga Nannochloropsis oceanica CCMP1779. PLoS Genet 8:e1003064

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • von Berlepsch S, Kunz HH, Brodesser S, Fink P, Marin K, Flugge UI, Gierth M (2012) The acyl-acyl carrier protein synthetase from Synechocystis sp. PCC 6803 mediates fatty acid import. Plant Physiol 159:606–617

    Article  CAS  Google Scholar 

  • Vrkoslav V, Míková R, Cvačka J (2009) Characterization of natural wax esters by MALDI-TOF mass spectrometry. J Mass Spectrom 44:101–110

    Article  CAS  PubMed  Google Scholar 

  • Wakimoto T, Kondo H, Nii H, Kimura K, Egami Y, Oka Y, Yoshida M, Kida E, Ye Y, Akahoshi S, Asakawa T (2011) Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus. Proc Natl Acad Sci U S A 108:17533–17537

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wallingford SC, Hughes MC, Green AC, van der Pols JC (2013) Plasma omega-3 and omega-6 concentrations and risk of cutaneous basal and squamous cell carcinomas in Australian adults. Cancer Epidemiol Biomark Prev 22:1900–1905

    Article  CAS  Google Scholar 

  • Weaver KL, Ivester P, Seeds M, Case LD, Arm JP, Chilton FH (2009) Effect of dietary fatty acids on inflammatory gene expression in healthy humans. J Biol Chem 284:15400–15407

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wisotzkey JD, Jurtshuk P Jr, Fox GE, Deinhard G, Poralla K (1992) Comparative sequence analyses on the 16S rRNA (rDNA) of Bacillus acidocaldarius, Bacillus acidoterrestris, and Bacillus cycloheptanicus and proposal for creation of a new genus, Alicyclobacillus gen. nov. Int J Syst Bacteriol 42:263–269

    Article  CAS  PubMed  Google Scholar 

  • Ye C, Qiao W, Yu X, Ji X, Huang H, Collier JL, Liu L (2015) Reconstruction and analysis of the genome-scale metabolic model of Schizochytrium limacinum SR21 for docosahexaenoic acid production. BMC Genomics 16:799

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Yoshida K, Hashimoto M, Hori R, Adachi T, Okuyama H, Orikasa Y, Nagamine T, Shimizu S, Ueno A, Morita N (2016) Bacterial long-chain polyunsaturated fatty acids: their biosynthetic genes, functions, and practical use. Mar Drugs 14:94

    Article  PubMed Central  Google Scholar 

  • Yu X, Liu T, Zhu F, Khosla C (2011) In vitro reconstitution and steady-state analysis of the fatty acid synthase from Escherichia coli. Proc Natl Acad Sci U S A 108:18643–18648

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Synthetic Genomics, Inc., La Jolla, CA, 92037, USA

    Eric R. Moellering

  2. Department of Family and Preventive Medicine, University of Utah School of Medicine, Salt Lake City, UT, 84132, USA

    Victoria L. Prince

  3. Stonybrook Apiary, Pittstown, NJ, 08867, USA

    Roger C. Prince

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  1. Eric R. Moellering
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  2. Victoria L. Prince
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  3. Roger C. Prince
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Correspondence to Roger C. Prince .

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  1. Centro de Ciencias Genomicas, Universidad Nacional Autonoma de Mexico Centro de Ciencias Genomicas, Cuernavaca, Morelos, Mexico

    Otto Geiger

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Moellering, E.R., Prince, V.L., Prince, R.C. (2016). Fatty Acids: Introduction. In: Geiger, O. (eds) Biogenesis of Fatty Acids, Lipids and Membranes. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-43676-0_2-1

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  • DOI: https://doi.org/10.1007/978-3-319-43676-0_2-1

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