Bacterial membrane lipids: Diversity in structures and pathways

FEMS Microbiology Reviews

Volumn 40, Issue 1, 2015, Pages 133-159

  Sohlenkamp, Christian ^a   Geiger, Otto ^a  

^a INSTITUTO DE CIENCIAS FÍSICAS   (Mexico)

Author keywords

Cardiolipin; Hopanoids; Ornithine lipid; Phosphatidylcholine; Phosphatidylethanolamine; Phosphatidylinositol; Phospholipid

Indexed keywords

BACTERIAL ENZYME; CYTIDINE DIPHOSPHATE DIGLYCERIDE; DIACYLGLYCEROL; DIACYLGLYCERYL HOMOSERINE; GLYCOLIPID; HOPANOID; MEMBRANE LIPID; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLINOSITOLMANNOSIDE; PHOSPHOLIPID; PHOSPHORUS; SPHINGOLIPID; SULFONOLIPID; SULFOQUINOVOSYL DIACYLGLYCEROL; UNCLASSIFIED DRUG;

BACTERIAL MEMBRANE; ESCHERICHIA COLI; LIPID COMPOSITION; LIPID METABOLISM; MEMBRANE STRUCTURE; NONHUMAN; PHOSPHOLIPID SYNTHESIS; REVIEW; TAXONOMY; BACTERIAL PHENOMENA AND FUNCTIONS; CELL MEMBRANE; CHEMISTRY; ENVIRONMENT; METABOLISM; PHYSIOLOGY; SPECIES DIFFERENCE;

BACTERIAL PHYSIOLOGICAL PHENOMENA; CELL MEMBRANE; ENVIRONMENT; ESCHERICHIA COLI; MEMBRANE LIPIDS; METABOLIC NETWORKS AND PATHWAYS; SPECIES SPECIFICITY;

EID: 84962018311     PISSN: 01686445     EISSN: 15746976     Source Type: Journal    
DOI: 10.1093/femsre/fuv008     Document Type: Review

References (306)

1. Abbanat DR, Leadbetter ER, Godchaux W, et al. Sulfonolipids are molecular determinants of gliding motility. Nature 1986;324:367-9.
2. Aktas M, Danne L, Möller P, et al. Membrane lipids in Agrobacterium tumefaciens: biosynthetic pathways and importance for pathogenesis. Front Plant Sci 2014;5:109.
3. Ames GF. Lipids of Salmonella typhimurium and Escherichia coli: structure and metabolism. J Bacteriol 1968;95:833-43.
4. Anders H, Power JF, MacKenzie AD, et al. Limisphaera ngatamarikiensis gen. nov. sp. nov., a thermophilic, pink-pigmented coccus isolated from subaqueous mud of a geothermal hotspring in New Zealand. Int J Syst Evol Micr 2015, doi:10.1099/ijs.0.00006310.1099/ijs.0.000063.
5. Anderson R, Hansen K. Structure of a novel phosphoglycolipid from Deinococcus radiodurans. J Biol Chem 1985;260:12219-23.
6. Antonsson B. Phosphatidylinositol synthase from mammalian tissues. Biochim Biophys Acta 1997;1348:179-86.
7. Arendt W, Groenewold MK, Hebecker S, et al. Identification and characterization of a periplasmic aminoacylphosphatidylglycerol hydrolase responsible for Pseudomonas aeruginosa lipid homeostasis. J Biol Chem 2013;288:24717-30.
8. Arendt W, Hebecker S, Jäger S, et al. Resistance phenotypes mediated by aminoacyl-phosphatidylglycerol synthases. J Bacteriol 2012;194:1401-16.
9. Arondel V, Benning C, Somerville CR. Isolation and functional expression in Escherichia coli of a gene encoding phosphatidylethanolamine methyltransferase (EC 2.1.1.17) from Rhodobacter sphaeroides. J Biol Chem 1993;268:16002-8.
10. Babinski KJ, Kanjilal SJ, Raetz CR. Accumulation of the lipid A precursor UDP-2,3-diacylglucosamine in an Escherichia coli mutant lacking the lpxH gene. J Biol Chem 2002a;277:25947-56.
11. Babinski KJ, Ribeiro AA, Raetz CR. The Escherichia coli gene encoding the UDP-2,3-diacylglucosamine pyrophosphatase of lipid A biosynthesis. J Biol Chem 2002b;277:25937-46.
12. Barridge JK, Shively JM. Phospholipids of the thiobacilli. J Bacteriol 1968;95:2182-5.
13. Batrakov SG, Nikitin DI, Mosezhnyi AE, et al. A glycine-containing phosphorus-free lipoaminoacid from the gram-negative marine bacterium Cyclobacterium marinus WH. Chem Phys Lipids 1999;99:139-43.
14. Benning C. Biosynthesis and function of the sulfolipid sulfoquinovosyl diacylglycerol. Annu Rev Plant Phys 1998;49: 53-75.
15. Benning C, Beatty JT, Prince RC, et al. The sulfolipid sulfoquinovosyldiacylglycerol is not required for photosynthetic electron transport in Rhodobacter sphaeroides but enhances growth under phosphate limitation. P Natl Acad Sci USA 1993;90:1561-5.
16. Benning C, Huang ZH, Gage DA. Accumulation of a novel glycolipid and a betaine lipid in cells of Rhodobacter sphaeroides grown under phosphate limitation. Arch Biochem Biophys 1995;317:103-11.
17. Benning C, Somerville CR. Identification of an operon involved in sulfolipid biosynthesis in Rhodobacter sphaeroides. J Bacteriol 1992a;174:6479-87.
18. Benning C, Somerville CR. Isolation and genetic complementation of a sulfolipid-deficient mutant of Rhodobacter sphaeroides. J Bacteriol 1992b;174:2352-60.
19. Berg S, Kaur D, Jackson M, et al. The glycosyltransferases of Mycobacterium tuberculosis-roles in the synthesis of arabinogalactan, lipoarabinomannan, and other glycoconjugates. Glycobiology 2007;17:35-56R.
20. Berg S, Wieslander A. Purification of a phosphatase which hydrolyzes phosphatidic acid, a key intermediate in glucolipid synthesis in Acholeplasma laidlawii A membranes. Biochim Biophys Acta 1997;1330:225-32.
21. Blumenberg M, Oppermann BI, Guyoneaud R, et al. Hopanoid production by Desulfovibrio bastinii isolated from oilfield formation water. FEMS Microbiol Lett 2009;293:73-8.
22. Bode HB, Zeggel B, Silakowski B, et al. Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca. Mol Microbiol 2003;47:471-81.
23. Bondoso J, Albuquerque L, Lobo-da-Cunha A, et al. Rhodopirellula lusitana sp. nov. and Rhodopirellula rubra sp. nov., isolated from the surface of macroalgae. Syst Appl Microbiol 2014;37:157-64.
24. Bosak T, Losick RM, Pearson A. A polycyclic terpenoid that alleviates oxidative stress. P Natl Acad Sci USA 2008;105:6725-9.
25. Boumann HA, Hopmans EC, vande Leemput I, et al. Ladderane phospholipids in anammox bacteria comprise phosphocholine and phosphoethanolamine headgroups. FEMS Microbiol Lett 2006;258:297-304.
26. Bradley AS, Pearson A, Saenz JP, et al. Adenosylhopane: the first intermediate in hopanoid side chain biosynthesis. Org Geochem 2010;41:1075-81.
27. Bravo JM, Perzl M, Hartner T, et al. Novel methylated triterpenoids of the gammacerane series fromthe nitrogen-fixing bacterium Bradyrhizobium japonicum USDA 110. Eur J Biochem 2001;268:1323-31.
28. Brito JA, Borges N, Vonrhein C, et al. Crystal structure of Archaeoglobus fulgidus CTP:inositol-1-phosphate cytidylyltransferase, a key enzyme for di-myo-inositol-phosphate synthesis in (hyper)thermophiles. J Bacteriol 2011;193:2177-85.
29. Bukata L, Altabe S, de Mendoza D, et al. Phosphatidylethanolamine synthesis is required for optimal virulence of Brucella abortus. J Bacteriol 2008;190:8197-203.
30. Caillon E, Lubochinsky B, Rigomier D. Occurrence of dialkyl ether phospholipids in Stigmatella aurantiaca DW4. J Bacteriol 1983;153:1348-51.
31. Campbell HA, Kent C. The CTP:phosphocholine cytidylyltransferase encoded by the licC gene of Streptococcus pneumoniae: cloning, expression, purification, and characterization. Biochim Biophys Acta 2001;1534:85-95.
32. Carman GM. Phosphatidate phosphatases and diacylglycerol pyrophosphate phosphatases in Saccharomyces cerevisiae and Escherichia coli. Biochim Biophys Acta 1997;1348:45-55.
33. Catucci L, Depalo N, Lattanzio VM, et al. Neosynthesis of cardiolipin in Rhodobacter sphaeroides under osmotic stress. Biochemistry 2004;43:15066-72.
34. Coleman J. Characterization of Escherichia coli cells deficient in 1-acyl-sn-glycerol-3- phosphate acyltransferase activity. J Biol Chem 1990;265:17215-21.
35. Coleman J. Characterization of the Escherichia coli gene for 1-acylsn-glycerol-3-phosphate acyltransferase (plsC). Mol Gen Genet 1992;232:295-303.
36. Comba S, Menendez-Bravo S, Arabolaza A, et al. Identification and physiological characterization of phosphatidic acid phosphatase enzymes involved in triacylglycerol biosynthesis in Streptomyces coelicolor. Microb Cell Fact 2013;12:9.
37. Comerci DJ, Altabe S, de Mendoza D, et al. Brucella abortus synthesizes phosphatidylcholine from choline provided by the host. J Bacteriol 2006;188:1929-34.
38. Conde-Alvarez R, Grilló MJ, Salcedo SP, et al. Synthesis of phosphatidylcholine, a typical eukaryotic phospholipid, is necessary for full virulence of the intracellular bacterial parasite Brucella abortus. Cell Microbiol 2006;8:1322-35.
39. Conover GM, Martínez-Morales F, Heidtman MI, et al. Phosphatidylcholine synthesis is required for optimal function of Legionella pneumophila virulence determinants. Cell Microbiol 2008;10:514-28.
40. Contreras I, Shapiro L, Henry S. Membrane phospholipid composition of Caulobacter crescentus. J Bacteriol 1978;135:1130-6.
41. Cooper CL, Jackowski S, Rock CO. Fatty acid metabolism in snglycerol-3-phosphate acyltransferase (plsB) mutants. J Bacteriol 1987;169:605-11.
42. Damsté JS, Rijpstra WI, Hopmans EC, et al. Structural characterization of diabolic acid-based tetraester, tetraether and mixed ether/ester, membrane-spanning lipids of bacteria from the order Thermotogales. Arch Microbiol 2007;188:629-41.
43. Dare K, Shepherd J, Roy H, et al. LysPGS formation in Listeria monocytogenes has broad roles in maintaining membrane integrity beyond antimicrobial peptide resistance. Virulence 2014;5:534-46.
44. de Rudder KE, López-Lara IM, Geiger O. Inactivation of the gene for phospholipid N-methyltransferase in Sinorhizobium meliloti: phosphatidylcholine is required for normal growth. Mol Microbiol 2000;37:763-72.
45. de Rudder KE, Sohlenkamp C, Geiger O. Plant-exuded choline is used for rhizobial membrane lipid biosynthesis by phosphatidylcholine synthase. J Biol Chem 1999;274:20011-6.
46. De Siervo AJ, Homola AD. Analysis of Caulobacter crescentus lipids. J Bacteriol 1980;143:1215-22.
47. DeChavigny A, Heacock PN, Dowhan W. Sequence and inactivation of the pss gene of Escherichia coli. Phosphatidylethanolamine may not be essential for cell viability. J Biol Chem 1991;266:5323-32.
48. Dees C, Shively JM. Localization of quantitation of the ornithine lipid of Thiobacillus thiooxidans. J Bacteriol 1982;149:798-9.
49. den Kamp JA, Redai I, van Deenen LL. Phospholipid composition of Bacillus subtilis. J Bacteriol 1969;99:298-303.
50. Devers EA, Wewer V, Dombrink I, et al. A processive glycosyltransferase involved in glycolipid synthesis during phosphate deprivation in Mesorhizobium loti. J Bacteriol 2011;193:1377-84.
51. Dickson RC. Roles for sphingolipids in Saccharomyces cerevisiae. Adv Exp Med Biol 2010;688:217-31.
52. Diercks H, Semeniuk A, Gisch N, et al. Accumulation of novel glycolipids and ornithine Lipids in Mesorhizobium loti under phosphate deprivation. J Bacteriol 2015;197:497-509.
53. Doughty DM, Coleman ML, Hunter RC, et al. The RND-family transporter, HpnN, is required for hopanoid localization to the outer membrane of Rhodopseudomonas palustris TIE-1. P Natl Acad Sci USA 2011;108:E1045-51.
54. Doughty DM, Hunter RC, Summons RE, et al. 2-Methylhopanoids are maximally produced in akinetes of Nostoc punctiforme: geobiological implications. Geobiology 2009;7:524-32.
55. Dowhan W. A retrospective: use of Escherichia coli as a vehicle to study phospholipid synthesis and function. Biochim Biophys Acta 2013;1831:471-94.
56. Eckau H, Dill D, Budzikiewicz H. Novel ceramides from Cystobacter fuscus (Myxobacterales). Z Naturforsch C 1984;39:1-9.
57. Ernst CM, Staubitz P, Mishra NN, et al. The bacterial defensin resistance proteinMprF consists of separable domains for lipid lysinylation and antimicrobial peptide repulsion. PLoS Pathog 2009;5:e1000660.
58. Evans RI, McClure PJ, Gould GW, et al. The effect of growth temperature on the phospholipid and fatty acyl compositions of non-proteolytic Clostridium botulinum. Int J Food Microbiol 1998;40:159-67.
59. Fang J, Barcelona MJ, Semrau JD. Characterization of methanotrophic bacteria on the basis of intact phospholipid profiles. FEMS Microbiol Lett 2000;189:67-72.
60. Fiedler W, Rotering H. Characterization of an Escherichia coli mdoB mutant strain unable to transfer sn-1-phosphoglycerol to membrane-derived oligosaccharides. J Biol Chem 1985;260:4799-806.
61. Fischer W, Leopold K. Polar lipids of four Listeria species containing L-lysylcardiolipin, a novel lipid structure, and other unique phospholipids. Int J Syst Bacteriol 1999;49(Pt 2): 653-62.
62. Fuerst JA, Sagulenko E. Beyond the bacterium: planctomycetes challenge our concepts of microbial structure and function. Nat Rev Microbiol 2011;9:403-13.
63. Fujishiro T, Shoji O, Nagano S, et al. Crystal structure of H2O2-dependent cytochrome P450SPα with its bound fatty acid substrate. J Biol Chem 2011;286:29941-50.
64. Gao JL, Weissenmayer B, Taylor AM, et al. Identification of a gene required for the formation of lyso-ornithine lipid, an intermediate in the biosynthesis of ornithine-containing lipids. Mol Microbiol 2004;53:1757-70.
65. Ge Z, Taylor DE. The Helicobacter pylori gene encoding phosphatidylserine synthase: sequence, expression, and insertional mutagenesis. J Bacteriol 1997;179:4970-6.
66. Geiger O, Gónzalez-Silva N, López-Lara IM, et al. Amino acidcontaining membrane lipids in bacteria. Prog Lipid Res 2010;49:46-60.
67. Geiger O, López-Lara IM, Sohlenkamp C. Phosphatidylcholine biosynthesis and function in bacteria. Biochim Biophys Acta 2013;1831:503-13.
68. Geiger O, Röhrs V, Weissenmayer B, et al. The regulator gene phoB mediates phosphate stress-controlled synthesis of the membrane lipid diacylglyceryl-N,N,N-trimethylhomoserine in Rhizobium (Sinorhizobium) meliloti. Mol Microbiol 1999;32: 63-73.
69. Geske T, Vom Dorp K, Dörmann P, et al. Accumulation of glycolipids and other non-phosphorous lipids in Agrobacterium tumefaciens grown under phosphate deprivation. Glycobiology 2013;23:69-80.
70. Gibbons HS, Lin S, Cotter RJ, et al. Oxygen requirement for the biosynthesis of the S-2-hydroxymyristate moiety in Salmonella typhimurium lipid A. J Biol Chem 2000;275: 32940-9.
71. Gibbons HS, Reynolds CM, Guan Z, et al. An inner membrane dioxygenase that generates the 2-hydroxymyristate moiety of Salmonella lipid A. Biochemistry 2008;47:2814-25.
72. Gidden J, Denson J, Liyanage R, et al. Lipid compositions in Escherichia coli and Bacillus subtilis during growth as determined by MALDI-TOF and TOF/TOF mass spectrometry. Int J Mass Spectrom 2009;283:178-84.
73. Giles DK, Hankins JV, Guan Z, et al. Remodelling of the Vibrio cholerae membrane by incorporation of exogenous fatty acids from host and aquatic environments. Mol Microbiol 2011;79:716-28.
74. Goldfine H. The appearance, disappearance and reappearance of plasmalogens in evolution. Prog Lipid Res 2010;49:493-8.
75. Goldfine H, Ellis ME. N-methyl groups in bacterial lipids. J Bacteriol 1964;87:8-15.
76. González-Silva N, López-Lara IM, Reyes-Lamothe R, et al. The dioxygenase-encoding olsD gene from Burkholderia cenocepacia causes the hydroxylation of the amide-linked fatty acyl moiety of ornithine-containing membrane lipids. Biochemistry 2011;50:6396-408.
77. Gould RM, Lennarz WJ. Biosynthesis of aminoacyl derivatives of phosphatidylglycerol. Biochem Bioph Res Co 1967;26:512-5.
78. Guerin ME, Kaur D, Somashekar BS, et al. New insights into the early steps of phosphatidylinositol mannoside biosynthesis in mycobacteria: PimB' is an essential enzyme of Mycobacterium smegmatis. J Biol Chem 2009;284:25687-96.
79. Guerin ME, Kordulakova J, Alzari PM, et al. Molecular basis of phosphatidyl-myo-inositol mannoside biosynthesis and regulation in mycobacteria. J Biol Chem 2010;285:33577-83.
80. Güler S, Essigmann B, Benning C. A cyanobacterial gene, sqdX, required for biosynthesis of the sulfolipid sulfoquinovosyldiacylglycerol. J Bacteriol 2000;182:543-5.
81. Güler S, Seeliger A, Härtel H, et al. A nullmutant of Synechococcus sp. PCC7942 deficient in the sulfolipid sulfoquinovosyl diacylglycerol. J Biol Chem 1996;271:7501-7.
82. Guo D, Tropp BE. A second Escherichia coli protein with CL synthase activity. Biochim Biophys Acta 2000;1483:263-74.
83. Hachmann AB, Angert ER, Helmann JD. Genetic analysis of factors affecting susceptibility of Bacillus subtilis to daptomycin. Antimicrob Agents Ch 2009;53:1598-609.
84. Hacker S, Sohlenkamp C, Aktas M, et al. Multiple phospholipid Nmethyltransferases with distinct substrate specificities are encoded in Bradyrhizobium japonicum. J Bacteriol 2008;190:571-80.
85. Hagen PO. Lipids of Sphaerophorus ridiculosis: plasmalogen composition. J Bacteriol 1974;119:643-5.
86. Hagio M, Gombos Z, Varkonyi Z, et al. Direct evidence for requirement of phosphatidylglycerol in photosystem II of photosynthesis. Plant Physiol 2000;124:795-804.
87. Hatch GM, McClarty G. Phospholipid composition of purified Chlamydia trachomatis mimics that of the eucaryotic host cell. Infect Immun 1998;66:3727-35.
88. Hebecker S, Arendt W, Heinemann IU, et al. Alanylphosphatidylglycerol synthase: mechanism of substrate recognition during tRNA-dependent lipid modification in Pseudomonas aeruginosa. Mol Microbiol 2011;80:935-50.
89. Hill DL, Ballou CE. Biosynthesis of mannophospholipids by Mycobacterium phlei. J Biol Chem 1966;241:895-902.
90. Hölzl G, Dörmann P. Structure and function of glycoglycerolipids in plants and bacteria. Prog Lipid Res 2007;46:225-43.
91. Hölzl G, Leipelt M, Ott C, et al. Processive lipid galactosyl/glucosyltransferases from Agrobacterium tumefaciens and Mesorhizobium loti display multiple specificities. Glycobiology 2005;15:874-86.
92. Huang HD, Wang W, Ma T, et al. Sphingomonas sanxanigenens sp. nov., isolated from soil. Int J Syst Evol Micr 2009;59:719-23.
93. Huang Y, Anderson R. Structure of a novel glucosaminecontaining phosphoglycolipid from Deinococcus radiodurans. J Biol Chem 1989;264:18667-72.
94. Huang Y, Anderson R. Glucosyl diglyceride lipid structures in Deinococcus radiodurans. J Bacteriol 1995;177:2567-71.
95. Huber R, Langworthy TA, Konig H, et al. Thermotoga-maritima sp-nov represents a new genus of unique extremely thermophilic eubacteria growing up to 90-degrees-C. Arch Microbiol 1986;144:324-33.
96. Ikushiro H, Islam MM, Okamoto A, et al. Structural insights into the enzymatic mechanism of serine palmitoyltransferase from Sphingobacterium multivorum. J Biochem 2009;146:549-62.
97. Iwamori M, Sakai A, Minamimoto N, et al. Characterization of novel glycolipid antigens with an α-galactose epitope in lactobacilli detected with rabbit anti-Lactobacillus antisera and occurrence of antibodies against them in human sera. J Biochem 2011;150:515-23.
98. Jackson BJ, Bohin JP, Kennedy EP. Biosynthesis of membranederived oligosaccharides: characterization of mdoB mutants defective in phosphoglycerol transferase I activity. J Bacteriol 1984;160:976-81.
99. Jackson M, Crick DC, Brennan PJ. Phosphatidylinositol is an essential phospholipid of mycobacteria. J Biol Chem 2000;275:30092-9.
100. Jahnke LL, Eder W, Huber R, et al. Signature lipids and stable carbon isotope analyses of Octopus Spring hyperthermophilic communities compared with those of Aquificales representatives. Appl Environ Microb 2001;67:5179-89.
101. Johnston NC, Baker JK, Goldfine H. Phospholipids of Clostridium perfringens: a reexamination. FEMS Microbiol Lett 2004;233: 65-8.
102. Jones DE, Smith JD. Phospholipids of the differentiating bacterium Caulobacter crescentus. Can J Biochem 1979;57:424-8.
103. Jones DS, Albrecht HL, Dawson KS, et al. Community genomic analysis of an extremely acidophilic sulfur-oxidizing biofilm. ISME J 2012;6:158-70.
104. Jorasch P, Wolter FP, Zahringer U, et al. A UDP glucosyltransferase from Bacillus subtilis successively transfers up to four glucose residues to 1,2-diacylglycerol: expression of ypfP in Escherichia coli and structural analysis of its reaction products. Mol Microbiol 1998;29:419-30.
105. Jorge CD, Borges N, Santos H. A novel pathway for the synthesis of inositol phospholipids uses CDP-inositol as donor of the polar head group. Environ Microbiol 2014, DOI:10.1111/1462-2920.12734.
106. Jyothikumar V, Klanbut K, Tiong J, et al. Cardiolipin synthase is required for Streptomyces coelicolor morphogenesis. Mol Microbiol 2012;84:181-97.
107. Kaneshiro T, Law JH. Phosphatidylcholine synthesis in Agrobacterium tumefaciens. I. Purification and properties of a phosphatidylethanolamine N-methyltransferase. J Biol Chem 1964;239:1705-13.
108. Kanipes MI, Henry SA. The phospholipid methyltransferases in yeast. Biochim Biophys Acta 1997;1348:134-41.
109. Kannenberg EL, Poralla K. Hopanoid biosynthesis and function in bacteria. Naturwissenschaften 1999;86:168-76.
110. Karnezis T, Fisher HC, Neumann GM, et al. Cloning and characterization of the phosphatidylserine synthase gene of Agrobacterium sp. strain ATCC 31749 and effect of its inactivation on production of high-molecular-mass (1->3)-beta-D-glucan (curdlan). J Bacteriol 2002;184:4114-23.
111. Kato M, Sakai M, Adachi K, et al. Distribution of betaine lipids in marine algae. Phytochemistry 1996;42:1341-45.
112. Kaur D, Guerin ME, Skovierova H, et al. Chapter 2: biogenesis of the cell wall and other glycoconjugates of Mycobacterium tuberculosis. Adv Appl Microbiol 2009;69:23-78.
113. Kawahara K, Kuraishi H, Zähringer U. Chemical structure and function of glycosphingolipids of Sphingomonas spp and their distribution among members of the α-4 subclass of Proteobacteria. J Ind Microbiol Biot 1999;23:408-13.
114. Kawahara K, Lindner B, Isshiki Y, et al. Structural analysis of a new glycosphingolipid from the lipopolysaccharide-lacking bacterium Sphingomonas adhaesiva. Carbohyd Res 2001;333: 87-93.
115. Kawahara K, Moll H, Knirel YA, et al. Structural analysis of two glycosphingolipids from the lipopolysaccharide-lacking bacterium Sphingomonas capsulata. Eur J Biochem 2000;267: 1837-46.
116. Kawai Y, Moribayashi A. Characteristic lipids of Bordetella pertussis: simple fatty acid composition, hydroxy fatty acids, and an ornithine-containing lipid. J Bacteriol 1982;151:996-1005.
117. Kawai Y, Moribayashi A, Yano I. Ornithine-containing lipid of Bordetella pertussis that carries hemagglutinating activity. J Bacteriol 1982;152:907-10.
118. Kawai Y, Yano I, Kaneda K. Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium-their structures and biological activities on erythrocytes. Eur J Biochem 1988;171:73-80.
119. Kawazoe R, Okuyama H, Reichardt W, et al. Phospholipids and a novel glycine-containing lipoamino acid in Cytophaga johnsonae Stanier strain C21. J Bacteriol 1991;173:5470-5.
120. Keck M, Gisch N, Moll H, et al. Unusual outer membrane lipid composition of the gram-negative, lipopolysaccharidelacking myxobacterium Sorangium cellulosum So ce56. J Biol Chem 2011;286:12850-9.
121. Kent C, Gee P, Lee SY, et al. A CDP-choline pathway for phosphatidylcholine biosynthesis in Treponema denticola. Mol Microbiol 2004;51:471-81.
122. Kenyon CN, Gray AM. Preliminary analysis of lipids and fatty acids of green bacteria and Chloroflexus aurantiacus. J Bacteriol 1974;120:131-8.
123. Khuller GK, Brennan PJ. The polar lipids of some species of Nocardia. J Gen Microbiol 1972;73:409-12.
124. Khuller GK, Taneja R, Kaur S, et al. Lipid composition and virulence of Mycobacterium tuberculosis H37Rv. Aust J Exp Biol Med 1982;60(Pt 5):541-7.
125. Kikuchi S, Shibuya I, Matsumoto K. Viability of an Escherichia coli pgsA nullmutant lacking detectable phosphatidylglycerol and cardiolipin. J Bacteriol 2000;182:371-6.
126. Kim KS, Manasherob R, Cohen SN. YmdB: a stress-responsive ribonuclease-binding regulator of E. coli RNase III activity. Gene Dev 2008;22:3497-508.
127. Klein S, Lorenzo C, Hoffmann S, et al. Adaptation of Pseudomonas aeruginosa to various conditions includes tRNAdependent formation of alanyl-phosphatidylglycerol. MolMicrobiol 2009;71:551-65.
128. Klug RM, Benning C. Two enzymes of diacylglyceryl-O-4'-(N,N,N,-trimethyl)homoserine biosynthesis are encoded by btaA and btaB in the purple bacterium Rhodobacter sphaeroides. P Natl Acad Sci USA 2001;98:5910-5.
129. Kobayashi T, Nishijima M, Tamori Y, et al. Acyl phosphatidylglycerol of Escherichia coli. Biochim Biophys Acta 1980;620:356-63.
130. Kodaki T, Yamashita S. Yeast phosphatidylethanolamine methylation pathway. Cloning and characterization of two distinct methyltransferase genes. J Biol Chem 1987;262: 15428-35.
131. Komaniecka I, Choma A, Mazur A, et al. Occurrence of an unusual hopanoid-containing lipid A among lipopolysaccharides from Bradyrhizobium species. J Biol Chem 2014;289:35644-55.
132. Kontnik R, Bosak T, Butcher RA, et al. Sporulenes, heptaprenyl metabolites from Bacillus subtilis spores. Org Lett 2008;10:3551-4.
133. Kordulakova J, Gilleron M, Puzo G, et al. Identification of the required acyltransferase step in the biosynthesis of the phosphatidylinositol mannosides ofmycobacterium species. J Biol Chem 2003;278:36285-95.
134. Kornspan JD, Rottem S. The phospholipid profile of mycoplasmas. J Lipids 2012;2012:640762.
135. Kwak BY, Zhang YM, Yun M, et al. Structure and mechanism of CTP:phosphocholine cytidylyltransferase (LicC) from Streptococcus pneumoniae. J Biol Chem 2002;277: 4343-50.
136. Lagier JC, Armougom F, Million M, et al. Microbial culturomics: paradigm shift in the human gut microbiome study. Clin Microbiol Infec 2012;18:1185-93.
137. Lagutin K, MacKenzie A, Houghton KM, et al. The identification and quantification of phospholipids fromthermus and meiothermus bacteria. Lipids 2014;49:1133-41.
138. Lamb DC, Jackson CJ, Warrilow AG, et al. Lanosterol biosynthesis in the prokaryote Methylococcus capsulatus: insight into the evolution of sterol biosynthesis. Mol Biol Evol 2007;24: 1714-21.
139. Lanéelle MA, Promé D, Lanéelle G, et al. Ornithine lipid of Mycobacterium tuberculosis: its distribution in some slow- and fast-growing mycobacteria. J Gen Microbiol 1990;136:773-8.
140. Lata P, Lal D, Lal R. Flavobacterium ummariense sp. nov., isolated from hexachlorocyclohexane-contaminated soil, and emended description of Flavobacterium ceti Vela et al. 2007. Int J Syst Evol Micr 2012;62:2674-9.
141. Leach S, Harvey P, Wait R. Changes with growth rate in the membrane lipid composition of and amino acid utilization by continuous cultures of Campylobacter jejuni. J Appl Microbiol 1997;82:631-40.
142. Lennarz WJ, Bonsen PP, van Deenen LL. Substrate specificity of O-L-lysylphosphatidylglycerol synthetase. Enzymatic studies on the structure of O-L-lysylphosphatidylglycerol. Biochemistry 1967;6:2307-12.
143. Lewenza S, Falsafi R, Bains M, et al. The olsA gene mediates the synthesis of an ornithine lipid in Pseudomonas aeruginosa during growth under phosphate-limiting conditions, but is not involved in antimicrobial peptide susceptibility. FEMS Microbiol Lett 2011;320:95-102.
144. Li QX, Dowhan W. Structural characterization of Escherichia coli phosphatidylserine decarboxylase. J Biol Chem 1988;263:11516-22.
145. Li Y, Wang X, Ernst RK. A rapid one-step method for the characterization of membrane lipid remodeling in Francisella using matrix-assisted laser desorption ionization time-offlight tandem mass spectrometry. Rapid Commun Mass Sp 2011;25:2641-8.
146. Lightner VA, Larson TJ, Tailleur P, et al. Membrane phospholipid synthesis in Escherichia coli. Cloning of a structural gene (plsB) of the sn-glycerol-3-phosphate acyltransferase. J Biol Chem 1980;255:9413-20.
147. Liscovitch M, Czarny M, Fiucci G, et al. Phospholipase D: molecular and cell biology of a novel gene family. Biochem J 2000;345(Pt 3):401-15.
148. Liu W, Sakr E, Schaeffer P, et al. Ribosylhopane, a novel bacterial hopanoid, as precursor of C35 bacteriohopanepolyols in Streptomyces coelicolor A3(2). Chembiochem 2014;15:2156-61.
149. Livermore BP, Johnson RC. Lipids of the Spirochaetales: comparison of the lipids of several members of the genera Spirochaeta, Treponema, and Leptospira. J Bacteriol 1974;120:1268-73.
150. López-Lara IM, Gao JL, Soto MJ, et al. Phosphorus-free membrane lipids of Sinorhizobium meliloti are not required for the symbiosis with alfalfa but contribute to increased cell yields under phosphorus-limiting conditions of growth. Mol Plant Microbe In 2005;18:973-82.
151. López-Lara IM, Sohlenkamp C, Geiger O. Membrane lipids in plant-associated bacteria: their biosyntheses and possible functions. Mol Plant Microbe In 2003;16:567-79.
152. Lorenzen W, Bozhuyuk KA, Cortina NS, et al. A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC ESI-MS. J Lipid Res 2014;55:2620-33.
153. Lowther J, Charmier G, Raman MC, et al. Role of a conserved arginine residue during catalysis in serine palmitoyltransferase. FEBS Lett 2011;585:1729-34.
154. Lowther J, Naismith JH, Dunn TM, et al. Structural, mechanistic and regulatory studies of serine palmitoyltransferase. Biochem Soc T 2012;40:547-54.
155. Lu YH, Guan Z, Zhao J, et al. Three phosphatidylglycerolphosphate phosphatases in the inner membrane of Escherichia coli. J Biol Chem 2011;286:5506-18.
156. Lu YJ, Zhang YM, Grimes KD, et al. Acyl-phosphates initiate membrane phospholipid synthesis in Gram-positive pathogens. Mol Cell 2006;23:765-72.
157. Makarova KS, Aravind L, Wolf YI, et al. Genome of the extremely radiation-resistant bacterium Deinococcus radiodurans viewed from the perspective of comparative genomics. Microbiol Mol Biol R 2001;65:44-79.
158. Makula RA, Finnerty WR. Phospholipid composition of Desulfovibrio species. J Bacteriol 1974;120:1279-83.
159. Makula RA, Finnerty WR. Isolation and characterization of an ornithine-containing lipid from Desulfovibrio gigas. J Bacteriol 1975;123:523-9.
160. Malott RJ, Steen-Kinnaird BR, Lee TD, et al. Identification of hopanoid biosynthesis genes involved in polymyxin resistance in Burkholderia multivorans. Antimicrob Agents Ch 2012;56:464-71.
161. Manca MC, Nicolaus B, Lanzotti V, et al. Glycolipids from Thermotoga maritima, a hyperthermophilic microorganism belonging to Bacteria domain. Biochim Biophys Acta 1992;1124: 249-52.
162. Marr AG, Ingraham JL. Effect of temperature on the composition of fatty acids in Escherichia coli. J Bacteriol 1962;84: 1260-7.
163. Mastronicolis SK, Arvanitis N, Karaliota A, et al. Coordinated regulation of cold-induced changes in fatty acids with cardiolipin and phosphatidylglycerol composition among phospholipid species for the food pathogen Listeria monocytogenes. Appl Environ Microb 2008;74:4543-9.
164. Matsumoto K. Phosphatidylserine synthase from bacteria. Biochim Biophys Acta 1997;1348:214-27.
165. Matsumoto K. Dispensable nature of phosphatidylglycerol in Escherichia coli: dual roles of anionic phospholipids. Mol Microbiol 2001;39:1427-33.
166. Matsumoto K, Okada M, Horikoshi Y, et al. Cloning, sequencing, and disruption of the Bacillus subtilis psd gene coding for phosphatidylserine decarboxylase. J Bacteriol 1998;180: 100-6.
167. Matsunaga I, Yokotani N, Gotoh O, et al. Molecular cloning and expression of fatty acid α-hydroxylase from Sphingomonas paucimobilis. J Biol Chem 1997;272:23592-6.
168. Meiers M, Volz C, Eisel J, et al. Altered lipid composition in Streptococcus pneumoniae cpoA mutants. BMC Microbiol 2014;14:12.
169. Minder AC, de Rudder KE, Narberhaus F, et al. Phosphatidylcholine levels in Bradyrhizobium japonicum membranes are critical for an efficient symbiosis with the soybean host plant. Mol Microbiol 2001;39:1186-98.
170. Miyazaki C, Kuroda M, Ohta A, et al. Genetic manipulation of membrane phospholipid composition in Escherichia coli: pgsA mutants defective in phosphatidylglycerol synthesis. P Natl Acad Sci USA 1985;82:7530-4.
171. Mizoguchi T, Harada J, Yoshitomi T, et al. A variety of glycolipids in green photosynthetic bacteria. Photosynth Res 2013;114:179-88.
172. Moore EK, Hopmans EC, Rijpstra WI, et al. Novel mono-, di-, and trimethylornithine membrane lipids in northern wetland planctomycetes. Appl Environ Microb 2013;79:6874-84.
173. Moribayashi A, Goto N, Arimitsu Y, et al. Lipids and fatty-acids of Leptospira interrogans serovar copenhageni virulent-strain Shibaura. Jpn J Med Sci Biol 1991;44:87-97.
174. Morii H, Ogawa M, Fukuda K, et al. A revised biosynthetic pathway for phosphatidylinositol in Mycobacteria. J Biochem 2010;148:593-602.
175. Morii H, Ogawa M, Fukuda K, et al. Ubiquitous distribution of phosphatidylinositol phosphate synthase and archaetidylinositol phosphate synthase in Bacteria and Archaea, which contain inositol phospholipid. Biochem Bioph Res Co 2014;443:86-90.
176. Moser R, Aktas M, Fritz C, et al. Discovery of a bifunctional cardiolipin/phosphatidylethanolamine synthase in bacteria. Mol Microbiol 2014a;92:959-72.
177. Moser R, Aktas M, Narberhaus F. Phosphatidylcholine biosynthesis in Xanthomonas campestris via a yeast-like acylation pathway. Mol Microbiol 2014b;91:736-50.
178. Müller FD, Beck S, Strauch E, et al. Bacterial predators possess unique membrane lipid structures. Lipids 2011;46:1129-40.
179. Nahaie MR, Goodfellow M, Minnikin DE, et al. Polar lipid and isoprenoid quinone composition in the classification of Staphylococcus. J Gen Microbiol 1984;130:2427-37.
180. Nakashima A, Hosaka K, Nikawa J. Cloning of a human cDNA for CTP-phosphoethanolamine cytidylyltransferase by complementation in vivo of a yeast mutant. J Biol Chem 1997;272:9567-72.
181. Nampoothiri KM, Hoischen C, Bathe B, et al. Expression of genes of lipid synthesis and altered lipid composition modulates L-glutamate efflux of Corynebacterium glutamicum. Appl Microbiol Biot 2002;58:89-96.
182. Nesbitt JA, 3rd, Lennarz WJ. Participation of aminoacyl transfer ribonucleic acid in aminoacyl phosphatidylglycerol synthesis. I. Specificity of lysyl phosphatidylglycerol synthetase. J Biol Chem 1968;243:3088-95.
183. Neunlist S, Rohmer M. Novel hopanoids from the methylotrophic bacteria Methylococcus capsulatus and Methylomonas methanica. (22S)-35-aminobacteriohopane-30,31,32,33,34-pentol and (22S)-35-amino-3 beta-methylbacteriohopane-30,31,32,33,34-pentol. Biochem J 1985;231:635-9.
184. Nguyen NA, Sallans L, Kaneshiro ES. The major glycerophospholipids of the predatory and parasitic bacterium Bdellovibrio bacteriovorus HID5. Lipids 2008;43:1053-63.
185. Nichols FC, Riep B, Mun J, et al. Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis. J Lipid Res 2004;45:2317-30.
186. Nichols FC, Riep B, Mun J, et al. Structures and biological activities of novel phosphatidylethanolamine lipids of Porphyromonas gingivalis. J Lipid Res 2006;47:844-53.
187. Nichols FC, Rojanasomsith K. Porphyromonas gingivalis lipids and diseased dental tissues. Oral Microbiol Immun 2006;21:84-92.
188. Niederweis M, Danilchanka O, Huff J, et al. Mycobacterial outer membranes: in search of proteins. Trends Microbiol 2010;18:109-16.
189. Nikaido H. Molecular basis of bacterial outer membrane permeability revisited. Microbiol Mol Biol R 2003;67:593-656.
190. Nikawa J, Yamashita S. Phosphatidylinositol synthase from yeast. Biochim Biophys Acta 1997;1348:173-8.
191. Nishi H, Komatsuzawa H, Fujiwara T, et al. Reduced content of lysyl-phosphatidylglycerol in the cytoplasmic membrane affects susceptibility to moenomycin, as well as vancomycin, gentamicin, and antimicrobial peptides, in Staphylococcus aureus. Antimicrob Agents Ch 2004;48:4800-7.
192. Nishijima S, Asami Y, Uetake N, et al. Disruption of the Escherichia coli cls gene responsible for cardiolipin synthesis. J Bacteriol 1988;170:775-80.
193. Nogly P, Gushchin I, Remeeva A, et al. X-ray structure of a CDPalcohol phosphatidyltransferase membrane enzyme and insights into its catalytic mechanism. Nat Commun 2014;5: 4169.
194. Okada M, Matsuzaki H, Shibuya I, et al. Cloning, sequencing, and expression in Escherichia coli of the Bacillus subtilis gene for phosphatidylserine synthase. J Bacteriol 1994;176:7456-61.
195. Oku Y, Kurokawa K, Ichihashi N, et al. Characterization of the Staphylococcus aureus mprF gene, involved in lysinylation of phosphatidylglycerol. Microbiology 2004;150:45-51.
196. Olofsson A, Vallstrom A, Petzold K, et al. Biochemical and functional characterization of Helicobacter pylori vesicles. Mol Microbiol 2010;77:1539-55.
197. Olsen RW, Ballou CE. Acyl phosphatidylglycerol. A new phospholipid from Salmonella typhimurium. J Biol Chem 1971;246: 3305-13.
198. Ostafin M, Haber J, Doronina NV, et al. Methylobacterium extorquens strain P14, a new methylotrophic bacteria producing poly-beta-hydroxybutyrate (PHB). Acta Microbiol Pol 1999;48:39-51.
199. Ostberg Y, Berg S, Comstedt P, et al. Functional analysis of a lipid galactosyltransferase synthesizing the major envelope lipid in the Lyme disease spirochete Borrelia burgdorferi. FEMS Microbiol Lett 2007;272:22-9.
200. Ourisson G, Rohmer M, Poralla K. Prokaryotic hopanoids and other polyterpenoid sterol surrogates. Annu Rev Microbiol 1987;41:301-33.
201. Palacios-Chaves L, Conde-Álvarez R, Gil-Ramírez Y, et al. Brucella abortus ornithine lipids are dispensable outer membrane components devoid of a marked pathogen-associated molecular pattern. PLoS One 2011;6:e16030.
202. Parsons JB, Rock CO. Bacterial lipids: metabolism and membrane homeostasis. Prog Lipid Res 2013;52:249-76.
203. Pata MO, Hannun YA, Ng CK. Plant sphingolipids: decoding the enigma of the Sphinx. New Phytol 2010;185:611-30.
204. Pérez-Gil J, Rodríguez-Concepción M. Metabolic plasticity for isoprenoid biosynthesis in bacteria. Biochem J 2013;452:19-25.
205. Perzl M, Muller P, Poralla K, et al. Squalene-hopene cyclase from Bradyrhizobium japonicum: cloning, expression, sequence analysis and comparison to other triterpenoid cyclases. Microbiology 1997;143(Pt 4):1235-42.
206. Peschel A, Jack RW, Otto M, et al. Staphylococcus aureus resistance to human defensins and evasion of neutrophil killing via the novel virulence factor MprF is based on modification of membrane lipids with L-lysine. J Exp Med 2001;193: 1067-76.
207. Peter-Katalinic J, Fischer W. α-D-glucopyranosyl-, D-alanyl- and L-lysylcardiolipin from gram-positive bacteria: analysis by fast atom bombardment mass spectrometry. J Lipid Res 1998;39:2286-92.
208. Pitta TP, Leadbetter ER, Godchaux W, 3rd. Increase of ornithine amino lipid content in a sulfonolipid-deficientmutant of Cytophaga johnsonae. J Bacteriol 1989;171:952-7.
209. Pramanik BN, Zechman JM, Das PR, et al. Bacterial phospholipid analysis by fast atom bombardment mass spectrometry. Biomed Environ Mass 1990;19:164-70.
210. Raetz CR, Dowhan W. Biosynthesis and function of phospholipids in Escherichia coli. J Biol Chem 1990;265:1235-8.
211. Raetz CR, Reynolds CM, Trent MS, et al. Lipid A modification systems in gram-negative bacteria. Annu Rev Biochem 2007;76:295-329.
212. Raetz CR, Whitfield C. Lipopolysaccharide endotoxins. Annu Rev Biochem 2002;71:635-700.
213. Rahman MM, Kolli VS, Kahler CM, et al. The membrane phospholipids of Neisseria meningitidis and Neisseria gonorrhoeae as characterized by fast atom bombardment mass spectrometry. Microbiology 2000;146(Pt 8):1901-11.
214. Raman MC, Johnson KA, Clarke DJ, et al. The serine palmitoyltransferase from Sphingomonas wittichii RW1: an interesting link to an unusual acyl carrier protein. Biopolymers 2010;93:811-22.
215. Ramana VV, Chakravarthy SK, Raj PS, et al. Descriptions of Rhodopseudomonas parapalustris sp. nov., Rhodopseudomonas harwoodiae sp. nov. and Rhodopseudomonas pseudopalustris sp. nov., and emended description of Rhodopseudomonas palustris. Int J Syst Evol Micr 2012;62: 1790-8.
216. Ratledge C, Wilkinson SG. Microbial Lipids. London, San Diego: Academic Press, 1988.
217. Reichmann NT, Gründling A. Location, synthesis and function of glycolipids and polyglycerolphosphate lipoteichoic acid in Gram-positive bacteria of the phylum Firmicutes. FEMS Microbiol Lett 2011;319:97-105.
218. Ricci JN, Coleman ML, Welander PV, et al. Diverse capacity for 2-methylhopanoid production correlates with a specific ecological niche. ISME J 2014;8:675-84.
219. Riekhof WR, Andre C, Benning C. Two enzymes, BtaA and BtaB, are sufficient for betaine lipid biosynthesis in bacteria. Arch Biochem Biophys 2005a;441:96-105.
220. Riekhof WR, Naik S, Bertrand H, et al. Phosphate starvation in fungi induces the replacement of phosphatidylcholine with the phosphorus-free betaine lipid diacylglyceryl-N,N,N-trimethylhomoserine. Eukaryot Cell 2014;13: 749-57.
221. Riekhof WR, Sears BB, Benning C. Annotation of genes involved in glycerolipid biosynthesis in Chlamydomonas reinhardtii: discovery of the betaine lipid synthase BTA1Cr. Eukaryot Cell 2005;4:242-52.
222. Ring MW, Schwar G, Bode HB. Biosynthesis of 2-hydroxy and isoeven fatty acids is connected to sphingolipid formation in myxobacteria. Chembiochem 2009;10:2003-10.
223. Rock CO, Heath RJ, Park HW, et al. The licC gene of Streptococcus pneumoniae encodes a CTP:phosphocholine cytidylyltransferase. J Bacteriol 2001;183:4927-31.
224. Roh SW, Lee HW, Yim KJ, et al. Rhodopirellula rosea sp. nov., a novel bacterium isolated from an ark clam Scapharca broughtonii. J Microbiol 2013;51:301-4.
225. Rojas-Jiménez K, Sohlenkamp C, Geiger O, et al. A ClC chloride channel homolog and ornithine-containing membrane lipids of Rhizobium tropici CIAT899 are involved in symbiotic efficiency and acid tolerance. Mol Plant Microbe In 2005;18:1175-85.
226. Romantsov T, Guan Z, Wood JM. Cardiolipin and the osmotic stress responses of bacteria. Biochim Biophys Acta 2009;1788:2092-100.
227. Romantsov T, Helbig S, Culham DE, et al. Cardiolipin promotes polar localization of osmosensory transporter ProP in Escherichia coli. Mol Microbiol 2007;64:1455-65.
228. Romantsov T, Stalker L, Culham DE, et al. Cardiolipin controls the osmotic stress response and the subcellular location of transporter ProP in Escherichia coli. J Biol Chem 2008;283: 12314-23.
229. Rossak M, Schafer A, Xu N, et al. Accumulation of sulfoquinovosyl-1-O-dihydroxyacetone in a sulfolipiddeficient mutant of Rhodobacter sphaeroides inactivated in sqdC. Arch Biochem Biophys 1997;340:219-30.
230. Rossak M, Tietje C, Heinz E, et al. Accumulation of UDPsulfoquinovose in a sulfolipid-deficient mutant of Rhodobacter sphaeroides. J Biol Chem 1995;270:25792-7.
231. Rowe NJ, Tunstall J, Galbraith L, et al. Lipid composition and taxonomy of [Pseudomonas] echinoides: transfer to the genus Sphingomonas. Microbiology 2000;146(Pt 11):3007-12.
232. Roy H, Dare K, Ibba M. Adaptation of the bacterial membrane to changing environments using aminoacylated phospholipids. Mol Microbiol 2009;71:547-50.
233. Roy H, Ibba M. RNA-dependent lipid remodeling by bacterial multiple peptide resistance factors. P Natl Acad Sci USA 2008;105:4667-72.
234. Roy H, Ibba M. Broad range amino acid specificity of RNAdependent lipid remodeling by multiple peptide resistance factors. J Biol Chem 2009;284:29677-83.
235. Ruzin A, Severin A, Moghazeh SL, et al. Inactivation of mprF affects vancomycin susceptibility in Staphylococcus aureus. Biochim Biophys Acta 2003;1621:117-21.
236. Saenz JP, Sezgin E, Schwille P, et al. Functional convergence of hopanoids and sterols in membrane ordering. P Natl Acad Sci USA 2012a;109:14236-40.
237. Saenz JP, Waterbury JB, Eglinton TI, et al. Hopanoids in marine cyanobacteria: probing their phylogenetic distribution and biological role. Geobiology 2012b;10:311-9.
238. Salzberg LI, Helmann JD. Phenotypic and transcriptomic characterization of Bacillus subtilis mutants with grossly altered membrane composition. J Bacteriol 2008;190:7797-807.
239. Sandoval-Calderón M, Geiger O, Guan Z, et al. A eukaryote-like cardiolipin synthase is present in Streptomyces coelicolor and in most actinobacteria. J Biol Chem 2009;284:17383-90.
240. Sauvageau J, Ryan J, Lagutin K, et al. Isolation and structural characterisation of the major glycolipids from Lactobacillus plantarum. Carbohyd Res 2012;357:151-6.
241. Schmerk CL, Bernards MA, Valvano MA. Hopanoid production is required for low-pH tolerance, antimicrobial resistance, and motility in Burkholderia cenocepacia. J Bacteriol 2011;193: 6712-23.
242. Schmerk CL, Welander PV, Hamad MA, et al. Elucidation of the Burkholderia cenocepacia hopanoid biosynthesis pathway uncovers functions for conserved proteins in hopanoid-producing bacteria. Environ Microbiol 2015;17: 735-50.
243. Seipke RF, Loria R. Hopanoids are not essential for growth of Streptomyces scabies 87-22. J Bacteriol 2009;191:5216-23.
244. Semeniuk A, Sohlenkamp C, Duda K, et al. A bifunctional glycosyltransferase from Agrobacterium tumefaciens synthesizes monoglucosyl and glucuronosyl diacylglycerol under phosphate deprivation. J Biol Chem 2014;289:10104-14.
245. Senff LM, Wegener WS, Brooks GF, et al. Phospholipid composition and phospholipase A activity of Neisseria gonorrhoeae. J Bacteriol 1976;127:874-80.
246. Serricchio M, Butikofer P. An essential bacterial-type cardiolipin synthase mediates cardiolipin formation in a eukaryote. P Natl Acad Sci USA 2012;109:E954-61.
247. Shi W, Bogdanov M, Dowhan W, et al. The pss and psd genes are required for motility and chemotaxis in Escherichia coli. J Bacteriol 1993;175:7711-4.
248. Shimizu T, Ohtani K, Hirakawa H, et al. Complete genome sequence of Clostridium perfringens, an anaerobic flesh-eater. P Natl Acad Sci USA 2002;99:996-1001.
249. Shimojima M. Biosynthesis and functions of the plant sulfolipid. Prog Lipid Res 2011;50:234-9.
250. Silipo A, Vitiello G, Gully D, et al. Covalently linked hopanoidlipid A improves outer-membrane resistance of a Bradyrhizobium symbiont of legumes. Nat Commun 2014;5:5106.
251. Sinninghe Damsté JS, Rijpstra WI, Geenevasen JA, et al. Structural identification of ladderane and other membrane lipids of planctomycetes capable of anaerobic ammonium oxidation (anammox). FEBS J 2005;272:4270-83.
252. Smith RD, Salyers AA. Incorporation of leucine into phospholipids of Bacteroides thetaiotaomicron. J Bacteriol 1981;145:8-13.
253. Sohlenkamp C, de Rudder KE, Geiger O. Phosphatidylethanolamine is not essential for growth of Sinorhizobium meliloti on complex culture media. J Bacteriol 2004;186:1667-77.
254. Sohlenkamp C, de Rudder KE, Röhrs VV, et al. Cloning and characterization of the gene for phosphatidylcholine synthase. J Biol Chem 2000;275:27500.
255. Sohlenkamp C, Galindo-Lagunas KA, Guan Z, et al. The lipid lysyl-phosphatidylglycerol is present in membranes of Rhizobium tropici CIAT899 and confers increased resistance to polymyxin B under acidic growth conditions. Mol Plant Microbe In 2007;20:1421-30.
256. Sohlenkamp C, López-Lara IM, Geiger O. Biosynthesis of phosphatidylcholine in bacteria. Prog Lipid Res 2003;42:115-62.
257. Solís-Oviedo RL, Martínez-Morales F, Geiger O, et al. Functional and topological analysis of phosphatidylcholine synthase from Sinorhizobium meliloti. Biochim Biophys Acta 2012;1821:573-81.
258. Sorensen PG, Cox RP, Miller M. Chlorosome lipids from Chlorobium tepidum: characterization and quantification of polar lipids and wax esters. Photosynth Res 2008;95:191-6.
259. Stalberg K, Neal AC, Ronne H, et al. Identification of a novel GPCAT activity and a new pathway for phosphatidylcholine biosynthesis in S. cerevisiae. J Lipid Res 2008;49:1794-806.
260. Stein J, Budzikiewicz H. Bacterial Components .36. Ceramide-1-Phosphoethanolamines from Myxococcus stipitatus. Z Naturforsch B 1988;43:1063-7.
261. Steiner S, Conti SF, Lester RL. Occurrence of phosphonosphingolipids in Bdellovibrio bacteriovorus strain UKi2. J Bacteriol 1973;116:1199-211.
262. Sturt HF, Summons RE, Smith K, et al. Intact polar membrane lipids in prokaryotes and sediments deciphered by highperformance liquid chromatography/electrospray ionization multistage mass spectrometry-new biomarkers for biogeochemistry and microbial ecology. Rapid Commun Mass Sp 2004;18:617-28.
263. Sud IJ, Feingold DS. Phospholipids and fatty acids of Neisseria gonorrhoeae. J Bacteriol 1975;124:713-7.
264. Svetlikova Z, Barath P, Jackson M, et al. Purification and characterization of the acyltransferase involved in biosynthesis of the major mycobacterial cell envelope glycolipid-monoacylated phosphatidylinositol dimannoside. Protein Expres Purif 2014;100:33-9.
265. Tahara Y, Kameda M, Yamada Y, et al. New lipid-ornithine and taurine-containing cerilipin. Agr Biol Chem 1976;40:243-4.
266. Tan BK, Bogdanov M, Zhao J, et al. Discovery of a cardiolipin synthase utilizing phosphatidylethanolamine and phosphatidylglycerol as substrates. P Natl Acad Sci USA 2012;109:16504-9.
267. Tannaes T, Bukholm IK, Bukholm G. High relative content of lysophospholipids of Helicobacter pylori mediates increased risk for ulcer disease. FEMS Immunol Med Mic 2005;44:17-23.
268. Tannaes T, Grav HJ, Bukholm G. Lipid profiles of Helicobacter pylori colony variants. APMIS 2000;108:349-56.
269. Tavana AM, Korachi M, Boote V, et al. Phospholipid analogues of Porphyromonas gingivalis. J Appl Microbiol 2000;88:791-9.
270. Taylor CJ, Anderson AJ, Wilkinson SG. Phenotypic variation of lipid composition in Burkholderia cepacia: a response to increased growth temperature is a greater content of 2-hydroxy acids in phosphatidylethanolamine and ornithine amide lipid. Microbiology 1998;144:1737-45.
271. Thedieck K, Hain T, Mohamed W, et al. The MprF protein is required for lysinylation of phospholipids in listerial membranes and confers resistance to cationic antimicrobial peptides (CAMPs) on Listeria monocytogenes. Mol Microbiol 2006;62:1325-39.
272. Thiele OW, Schwinn G. The free lipids of Brucella melitensis and Bordetella pertussis. Eur J Biochem 1973;34:333-44.
273. Tornabene TG. Lipid composition of selected strains of Yersinia pestis and Yersinia pseudotuberculosis. Biochim Biophys Acta 1973;306:173-85.
274. Trana AK, Khuller GK, Subrahmanyam D. Metabolism of phospholipids in Nocardia polychromogenes. J Gen Microbiol 1980;116:89-92.
275. Trombé MC, Lanéelle MA, Lanéelle G. Lipid composition of aminopterin-resistant and sensitive strains of Streptococcus pneumoniae. Effect of aminopterin inhibition. Biochim Biophys Acta 1979;574:290-300.
276. Tsatskis Y, Khambati J, Dobson M, et al. The osmotic activation of transporter ProP is tuned by both its C-terminal coiled-coil and osmotically induced changes in phospholipid composition. J Biol Chem 2005;280:41387-94.
277. Vences-Guzmán MA, Geiger O, Sohlenkamp C. Sinorhizobium meliloti mutants deficient in phosphatidylserine decarboxylase accumulate phosphatidylserine and are strongly affected during symbiosis with alfalfa. J Bacteriol 2008;190:6846-56.
278. Vences-Guzmán MA, Geiger O, Sohlenkamp C. Ornithine lipids and their structural modifications: from A to E and beyond. FEMS Microbiol Lett 2012;335:1-10.
279. Vences-Guzmán MA, Guan Z, Bermúdez-Barrientos JR, et al. Agrobacteria lacking ornithine lipids induce more rapid tumour formation. Environ Microbiol 2013;15:895-906.
280. Vences-Guzmán MA, Guan Z, Escobedo-Hinojosa WI, et al. Discovery of a bifunctional acyltransferase responsible for ornithine lipid synthesis in Serratia proteamaculans. Environ Microbiol 2014, DOI:10.1111/1462-2920.12562.
281. Vences-Guzmán MA, Guan Z, Ormeno-Orrillo E, et al. Hydroxylated ornithine lipids increase stress tolerance in Rhizobium tropici CIAT899. Mol Microbiol 2011;79:1496-514.
282. Vinuesa P, Neumann-Silkow F, Pacios-Bras C, et al. Genetic analysis of a pH-regulated operon from Rhizobium tropici CIAT899 involved in acid tolerance and nodulation competitiveness. Mol Plant Microbe In 2003;16:159-68.
283. Wang XG, Scagliotti JP, Hu LT. Phospholipid synthesis in Borrelia burgdorferi: BB0249 and BB0721 encode functional phosphatidylcholine synthase and phosphatidylglycerolphosphate synthase proteins. Microbiology 2004;150:391-7.
284. Weiser JN, Love JM, Moxon ER. The molecular mechanism of phase variation of H. influenzae lipopolysaccharide. Cell 1989;59:657-65.
285. Weissenmayer B, Gao JL, López-Lara IM, et al. Identification of a gene required for the biosynthesis of ornithine-derived lipids. Mol Microbiol 2002;45:721-33.
286. Weissenmayer B, Geiger O, Benning C. Disruption of a gene essential for sulfoquinovosyldiacylglycerol biosynthesis in Sinorhizobium meliloti has no detectable effect on root nodule symbiosis. Mol Plant Microbe In 2000;13:666-72.
287. Welander PV, Coleman ML, Sessions AL, et al. Identification of a methylase required for 2-methylhopanoid production and implications for the interpretation of sedimentary hopanes. P Natl Acad Sci USA 2010;107:8537-42.
288. Welander PV, Doughty DM, Wu CH, et al. Identification and characterization of Rhodopseudomonas palustris TIE-1 hopanoid biosynthesis mutants. Geobiology 2012;10: 163-77.
289. Welander PV, Hunter RC, Zhang L, et al. Hopanoids play a role in membrane integrity and pH homeostasis in Rhodopseudomonas palustris TIE-1. J Bacteriol 2009;191: 6145-56.
290. Welander PV, Summons RE. Discovery, taxonomic distribution, and phenotypic characterization of a gene required for 3-methylhopanoid production. P Natl Acad Sci USA 2012;109:12905-10.
291. Wessel M, Klüsener S, Gödeke J, et al. Virulence of Agrobacterium tumefaciens requires phosphatidylcholine in the bacterial membrane. Mol Microbiol 2006;62:906-15.
292. White DC, Frerman FE. Extraction, characterization, and cellular localization of the lipids of Staphylococcus aureus. J Bacteriol 1967;94:1854-67.
293. White RH. Biosynthesis of the sulfonolipid 2-amino-3-hydroxy-15-methylhexadecane-1-sulfonic acid in the gliding bacterium Cytophaga johnsonae. J Bacteriol 1984;159:42-6.
294. Wilderman PJ, Vasil AI, Martin WE, et al. Pseudomonas aeruginosa synthesizes phosphatidylcholine by use of the phosphatidylcholine synthase pathway. J Bacteriol 2002;184:4792-9.
295. Williams JG, McMaster CR. Scanning alanine mutagenesis of the CDP-alcohol phosphotransferase motif of Saccharomyces cerevisiae cholinephosphotransferase. J Biol Chem 1998;273:13482-7.
296. Xue HW, Hosaka K, Plesch G, et al. Cloning of Arabidopsis thaliana phosphatidylinositol synthase and functional expression in the yeast pis mutant. Plant Mol Biol 2000;42:757-64.
297. Yabuuchi E, Kosako Y, Yano I, et al. Transfer of two Burkholderia and an Alcaligenes species to Ralstonia gen. Nov.: Proposal of Ralstonia pickettii (Ralston, Palleroni and Doudoroff 1973) comb. Nov., Ralstonia solanacearum (Smith 1896) comb. Nov. and Ralstonia eutropha (Davis 1969) comb. Nov. Microbiol Immunol 1995;39:897-904.
298. Yao J, Abdelrahman YM, Robertson RM, et al. Type II fatty acid synthesis is essential for the replication of Chlamydia trachomatis. J Biol Chem 2014;289:22365-76.
299. Yard BA, Carter LG, Johnson KA, et al. The structure of serine palmitoyltransferase; gateway to sphingolipid biosynthesis. J Mol Biol 2007;370:870-86.
300. Yuzawa Y, Shimojima M, Sato R, et al. Cyanobacterial monogalactosyldiacylglycerol-synthesis pathway is involved in normal unsaturation of galactolipids and lowtemperature adaptation of Synechocystis sp. PCC 6803. Biochim Biophys Acta 2014;1841:475-83.
301. Zavaleta-Pastor M, Sohlenkamp C, Gao JL, et al. Sinorhizobium meliloti phospholipase C required for lipid remodeling during phosphorus limitation. P Natl Acad Sci USA 2010;107:302-7.
302. Zhang JR, Idanpaan-Heikkila I, Fischer W, et al. Pneumococcal licD2 gene is involved in phosphorylcholine metabolism. Mol Microbiol 1999;31:1477-88.
303. Zhang X, Ferguson-Miller SM, Reid GE. Characterization of ornithine and glutamine lipids extracted from cell membranes of Rhodobacter sphaeroides. J Am Soc Mass Spectr 2009;20: 198-212.
304. Zhang Y, Yang Z, Huang X, et al. Cloning, expression, and characterization of a thermostable PAP2L2, a new member of the type-2 phosphatidic acid phosphatase family from Geobacillus toebii T-85. Biosci Biotechnol Biochem 2008;72: 3134-41.
305. Zhang YQ, Chen YG, Li WJ, et al. Sphingomonas yunnanensis sp. nov., a novel gram-negative bacterium from a contaminated plate. Int J Syst Evol Mic 2005;55:2361-4.
306. Zhou P, Hu R, Chandan V, et al. Simultaneous analysis of cardiolipin and lipid A from Helicobacter pylori by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Mol Biosyst 2012;8:720-5.