13,16-Dimethyl octacosanedioic acid (iso-Diabolic Acid), a common membrane-spanning lipid of Acidobacteria subdivisions 1 and 3

Applied and Environmental Microbiology

Volumn 77, Issue 12, 2011, Pages 4147-4154

  Sinninghe Damsté, Jaap S ^a,b   Rijpstra, W Irene C ^a   Hopmans, Ellen C ^a   Weijers, Johan W H ^b   Foesel, Bärbel U ^c   Overmann, Jörg ^c   Dedysh, Svetlana N ^d  

^a ROYAL NETHERLANDS INSTITUTE FOR SEA RESEARCH   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c LEIBNIZ INSTITUTE DSMZ GERMAN COLLECTION OF MICROORGANISMS AND CELL CULTURES   (Germany)

^d WINOGRADSKY INSTITUTE OF MICROBIOLOGY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; CELL MATERIALS; DIRECT ANALYSIS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MEMBRANE LIPIDS; POLAR LIPIDS;

BACTERIA; BACTERIOLOGY; ETHERS; GAS CHROMATOGRAPHY; GLYCEROL; HYDROLYSIS; LIPIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SOILS;

FATTY ACIDS;

DIABOLIC ACIDS; DICARBOXYLIC ACID;

BACTERIUM; BIOCHEMICAL COMPOSITION; GAS CHROMATOGRAPHY; HYDROLYSIS; LIPID; MASS SPECTROMETRY; MEMBRANE; ORGANIC ACID; PEAT; TAXONOMY;

ARTICLE; BACTERIUM; CELL MEMBRANE; CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY;

BACTERIA; CELL MEMBRANE; CHROMATOGRAPHY, LIQUID; DICARBOXYLIC ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY;

ACIDOBACTERIA; BACTERIA (MICROORGANISMS); THERMOANAEROBACTER;

EID: 79960096438     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.00466-11     Document Type: Article

References (54)

1. Angle, J. S., S. P. Mcgrath, and R. L. Chaney. 1991. New culture-medium containing ionic concentrations of nutrients similar to concentrations found in the soil solution. Appl. Environ. Microbiol. 57:3674-3676.
2. Balch, W. E., G. E. Fox, L. J. Magrum, C. R. Woese, and R. S. Wolfe. 1979. Methanogens-re-evaluation of a unique biological group. Microbiol. Rev. 43:260-296.
3. Balk, M., et al. 2009. Isolation and characterization of a new CO-utilizing strain, Thermoanaerobacter thermohydrosulfuricus subsp. carboxydovorans, isolated from a geothermal spring in Turkey. Extremophiles 13:885-894.
4. Barns, S. M., E. C. Cain, L. Sommerville, and C. R. Kuske. 2007. Acidobacteria phylum sequences in uranium-contaminated subsurface sediments greatly expand the known diversity within the phylum. Appl. Environ. Microbiol. 73:3113-3116.
5. Bligh E. G., and W. J. Dyer. 1959. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37:911-917.
6. Clarke, N. G., G. P. Hazlewood, and R. M. C. Dawson. 1980. Structure of diabolic acid-containing phospholipids isolated from Butyrivibrio sp. Biochem. J. 191:561-569.
7. Coates, J. D., D. J. Ellis, C. V. Gaw, and D. R. Lovley. 1999. Geothrix fermentans gen. nov., sp nov., a novel Fe(III)-reducing bacterium from a hydrocarbon-contaminated aquifer. Int. J. Syst. Bacteriol. 49:1615-1622.
8. Damsté, J. S. S., et al. 2007. Structural characterization of diabolic acidbased tetraester, tetraether and mixed ether/ester, membrane-spanning lipids of bacteria from the order Thermotogales. Arch. Microbiol. 188:629-641.
9. Dedysh, S. N., et al. Bryocella elongata gen. nov., sp. nov., a novel member of subdivision 1 of the Acidobacteria isolated from a methanotrophic enrichment culture. Int. J. Syst. Evol. Microbiol., in press.
10. Dedysh, S. N., T. A. Pankratov, S. E. Belova, I. S. Kulichevskaya, and W. Liesack. 2006. Phylogenetic analysis and in situ identification of Bacteria community composition in an acidic Sphagnum peat bog. Appl. Environ. Microbiol. 72:2110-2117.
11. DeRosa, M., et al. 1988. A new 15,16-dimethyl-30-glyceryloxytriacontanoic acid from lipids of Thermotoga maritima. J. Chem. Soc. hem. Commun. 1988:1300-1301.
12. Eichorst, S. A., J. A. Breznak, and T. M. Schmidt. 2007. Isolation and characterization of soil bacteria that define Terriglobus gen. nov., in the phylum Acidobacteria. Appl. Environ. Microbiol. 73:2708-2717.
13. Faoro, H., et al. 2010. Influence of soil characteristics on the diversity of bacteria in the Southern Brazilian Atlantic Forest. Appl. Environ. Microbiol. 76:4744-4749.
14. Fierer, N., M. A. Bradford, and R. B. Jackson. 2007. Toward an ecological classification of soil bacteria. Ecology 88:1354-1364.
15. Fitz, W., and D. Arigoni. 1992. Biosynthesis of 15,16-dimethyltriacontanedioic acid (diabolic acid) from [16-(H-2)3]- and [14-(H-2)2]-almitic acids. J. Chem. Soc. Chem. Commun. 1992:1533-1534.
16. Fukunaga, Y., M. Kurahashi, K. Yanagi, A. Yokota, and S. Harayama. 2008. Acanthopleuribacter pedis gen. nov., sp. nov., a marine bacterium isolated from a chiton, and description of Acanthopleuribacteraceae fam. nov., Acanthopleuribacterales ord. nov., Holophagaceae fam. nov., Holophagales ord. nov. and Holophagae classis nov. in the phylum 'Acidobacteria'. Int. J. Syst. Evol. Microbiol. 58:2597-2601.
17. Hopmans, E. C., S. Schouten, R. D. Pancost, M. T. J. Van der Meer, and J. S. Sinninghe Damsté. 2000. Analysis of intact tetraether lipids in archaeal cell material and sediments by high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. Rapid Commun. Mass Spectrom. 14:585-589.
18. Huber, R., et al. 1986. Thermotoga maritima sp. nov. represents a new genus of unique extremely thermophilic eubacteria growing up to 90°C. Arch. Microbiol. 144:324-333.
19. Janssen, P. H. 2006. Identifying the dominant soil bacterial taxa in libraries of 16S rRNA and 16S rRNA genes. Appl. Environ. Microbiol. 72:1719-1728.
20. Jeanthon, C., et al. 1995. Thermotoga subterranea sp. nov., a new thermophilic bacterium isolated from a continental oil reservoir. Arch. Microbiol. 164:91-97.
21. Jones, R. T., et al. 2009. A comprehensive survey of soil acidobacterial diversity using pyrosequencing and clone library analyses. ISME J. 3:442-453.
22. Jung, S., and R. I. Hollingsworth. 1994. Structures and stereochemistry of the very long,α,ω-bifunctional alkyl species in the membrane of Sarcina ventriculi indicate that they are formed by tail-to-tail coupling of normal fatty acids. J. Lipid Res. 35:1932-1945.
23. Jung, S., S. E. Lowe, R. I. Hollingsworth, and J. G. Zeikus. 1993. Sarcina ventriculi synthesizes very long chain dicarboxylic acids in response to different forms of environmental stress. J. Biol. Chem. 268:2828-2835.
24. Jung, S., J. G. Zeikus, and R. I. Hollingsworth. 1994. A new family of very long chain,α,ω-dicarboxylic acids is a major structural fatty acyl component of the membrane lipids of Thermoanaerobacter ethanolicus 39E. J. Lipid Res. 35:1057-1065.
25. Kishimoto, N., Y. Kosako, and T. Tano. 1991. Acidobacterium capsulatum gen. nov., sp. nov., an acidophilic chemoorganotrophic bacterium containing menaquinone from acidic mineral environment. Curr. Microbiol. 22:1-7.
26. Koch, I. H., F. Gich, P. F. Dunfield, and J. Overmann. 2008. Edaphobacter modestus gen. nov., sp. nov., and Edaphobacter aggregans sp. nov., acidobacteria isolated from alpine and forest soils. Int. J. Syst. Evol. Microbiol. 58:1114-1122.
27. Koga, Y., M. Nishihara, H. Morii, and M. Akagawa-Matsushita. 1993. Ether polar lipids of methanogenic bacteria: structures, comparative aspects, and biosyntheses. Microbiol. Rev. 57:164-182.
28. Kon, T., N. Nemoto, T. Oshima, and A. Yamagishi. 2002. Effects of a squalene epoxidase inhibitor, terbinafine, on ether lipid biosyntheses in a thermoacidophilic archaeon, Thermoplasma acidophilum. J. Bacteriol. 184: 1395-1401.
29. Kraigher, B., et al. 2006. Microbial activity and community structure in two drained fen soils in the Ljubljana Marsh. Soil Biol. Biochem. 38:2762-2771.
30. Kulichevskaya, I. S., N. E. Suzina, W. Liesack, and S. N. Dedysh. 2010. Bryobacter aggregatus gen. nov., sp. nov., a peat-inhabiting, aerobic chemoorganotroph from subdivision 3 of the Acidobacteria. Int. J. Syst. Evol. Microbiol. 60:301-306.
31. Lauber, C. L., M. Hamady, R. Knight, and N. Fierer. 2009. Pyrosequencingbased assessment of soil pH as a predictor of soil bacterial community structure at the continental scale. Appl. Environ. Microbiol. 75:5111-5120.
32. Lee, S., S. Kang, J. N. Kim, and S. Jung. 2002. Structural analyses of the novel phosphoglycolipids containing the unusual very long bifunctional acyl chain,α,ω-13,16-dimethyloctacosanedioate in Thermoanaerobacter ethanolicus. Bull. Korean Chem. Soc. 23:1778-1784.
33. Liesack, W., F. Bak, J.-U. Kreft, and E. Stackebrandt. 1994. Holophaga foetida gen. nov., sp. nov., a new, homoacetogenic bacterium degrading methoxylated aromatic compounds. Arch. Microbiol. 162:85-90.
34. Morales, S. E., et al. 2006. Comparison of bacterial communities in New England Sphagnum bogs using terminal restriction fragment length polymorphism (T-RFLP). Microb. Ecol. 52:34-44.
35. Nichols, P. D., J. B. Guckert, and D. C. White. 1986. Determination of monounsaturated fatty acid double-bond position and geometry for microbial monocultures and complex consortia by capillary GC-MS of their dimethyl disulphide adducts. J. Microbiol. Methods 5:49-55.
36. Nishihara, M., H. Morii, and Y. Koga. 1989. Heptads of polar ether lipids of an archaebacterium, Methanobacterium thermoautotrophicum: structure and biosynthetic relationship. Biochemistry 28:95-102.
37. 2 vent. Geochim. Cosmochim. Acta 74:2697-2716.
38. Pancost, R. D., and J. S. Sinninghe Damsté. 2003. Carbon isotopic compositions of prokaryotic lipids as tracers of carbon cycling in diverse settings. Chem. Geol. 195:29-58.
39. Pankratov, T. A., S. E. Belova, and S. N. Dedysh. 2005. Evaluation of the phylogenetic diversity of prokaryotic microorganisms in Sphagnum peat bogs by means of fluorescence in situ hybridization (FISH). Microbiology 74:722-728.
40. Pankratov, T. A., and S. N. Dedysh. 2010. Granulicella paudicola gen. nov., sp. nov., Granulicella pectinivorans sp. nov., Granulicella aggregans sp. nov. and Granulicella rosea sp. nov., acidophilic, polymers-degrading Acidobacteria from Sphagnum peat bogs. Int. J. Syst. Evol. Microbiol. 60:2951-2959.
41. Pankratov, T. A., Y. M. Serkebaeva, I. S. Kulichevskaya, W. Liesack, and S. N. Dedysh. 2008. Substrate-induced growth and isolation of Acidobacteria from acidic Sphagnum peat. ISME J. 2:551-560.
42. Pitcher, A., E. C. Hopmans, S. Schouten, and J. S. Sinninghe Damsté. 2009. Separation of core and intact polar archaeal tetraether lipids using silica columns: insights into living and fossil biomass contributions. Org. Geochem. 40:12-19.
43. Ring, M. W., et al. 2006. Novel iso-branched ether lipids as specific markers of developmental sporulation in the myxobacterium Myxococcus xanthus. J. Biol. Chem. 281:36691-36700.
44. 86 paleothermometry by high-performance liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry. Anal. Chem. 9:2940-2944.
45. Sinninghe Damsté, J. S., E. C. Hopmans, R. D. Pancost, S. Schouten, and J. A. J. Geenevasen. 2000. Newly discovered non-isoprenoid glycerol dialkyl glycerol tetraether lipids in sediments. J. Chem. Soc. Chem. Commun. 2000: 1683-1684.
46. Sturt, H. F., R. E. Summons, K. Smith, M. Elvert, and K.-U. Hinrichs. 2004. Intact polar membrane lipids in prokaryotes and sediments deciphered by high-performance liquid chromatography/electrospray ionization multistage mass spectrometry-new biomarkers for biogeochemistry and microbial ecology. Rapid Commun. Mass Spectrom. 18:617-628.
47. Tschech, A., and N. Pfennig. 1984. Growth-yield increase linked to caffeate reduction in Acetobacterium woodii. Arch. Microbiol. 37:163-167.
48. Ward, N. L., et al. 2009. Three genomes from the phylum Acidobacteria provide insight into the lifestyles of these microorganisms in soils. Appl. Environ. Microbiol. 75:2046-2056.
49. Weijers, J. W. H., et al. 2009. Constraints on the biological source(s) of the orphan branched tetraether membrane lipids. Geomicrobiol. J. 26:402-414.
50. Weijers, J. W. H., et al. 2006. Membrane lipids of mesophilic anaerobic bacteria thriving in peats have typical archaeal traits. Environ. Microbiol. 8:648-657.
51. 86 proxy and the BIT index. Org. Geochem. 37:1680-1693.
52. Weijers, J. W. H., S. Schouten, J. C. van den Donker, E. C. Hopmans, and J. S. Sinninghe Damsté. 2007. Environmental controls on bacterial tetraether membrane lipid distribution in soils. Geochim. Cosmochim. Acta 71: 703-713.
53. Weijers, J. W. H., G. L. B. Wiesenberg, R. Bol, E. C. Hopmans, and R. D. Pancost. 2010. Carbon isotopic composition of branched tetraether membrane lipids in soils suggest a rapid turnover and a heterotrophic life style of their source organism(s). Biogeosciences 7:2959-973.
54. Windberger, E., R. Huber, A. Trincone, H. Fricke, and K. O. Stetter. 1989. Thermotoga thermarum sp. nov. and Thermotoga neapolitana occurring in African continental solfataric springs. Arch. Microbiol. 151:506-512.