Significance and taxonomic value of iso and anteiso monoenoic fatty acids and branded beta-hydroxy acids in Desulfovibrio desulfuricans

The fatty acids obtained from extractable lipids of the anaerobic sulfate bacterium Desulfovibrio desulfuricans were identified. Saturated and monoenoic iso (C15-C19) and anteiso (C15, C17) fatty acids and saturated normal (C14-C18) and monoenoic normal (C16, C18) fatty acids were shown to be shown to be present by capillary gas chromatography-mass spectrometry. Iso and anteiso beta-hydroxy fatty acids were analyzed as trimethylsilyl ethers in the same way. The position of methyl branches in the monoenoic fatty acids was determined from characteristic fragment ions in the mass spectra of their methyl esters. Disilyloxy methyl esters, prepared by derivatization of the mono unsaturated methyl esters and analyzed by capillary gas chromatography-mass spectrometry, provided the position of double bonds. The monoenoic fatty acids identified in this way were normal (delta7-C16:1, delta9-C16:1, delta9-C18:1, delta11-C18:1), iso (delta7-C15:1, delta9-C16:1, delta9-C17:1, delta11-C18:1, delta11-C19:1), and anteiso (delta7-C15:1, delta9-C17:1). Iso delta9-C17:1 fatty acid is present as the major component. The occurrence of these monoenoic fatty acids in this bacterium is of taxonomical importance.

[1]  J. Boon,et al.  Organic geochemistry of Walvis Bay diatomaceous ooze—I. Occurrence and significance of the fatty acids , 1975 .

[2]  W. Finnerty,et al.  Phospholipid Composition of Desulfovibrio Species , 1974, Journal of bacteriology.

[3]  T. Kaneda Positional preference of fatty acids in phospholipids of Bacillus cereus and its relation to growth temperature. , 1972, Biochimica et biophysica acta.

[4]  K. Karlsson,et al.  The structure of sphingomyelin of the honey bee (Apis mellifera). , 1972, Biochimica et biophysica acta.

[5]  G. M. Helmkamp,et al.  Beta-hydroxydecanoyl thioester dehydrase. Studies on molecular structure and active site. , 1969, The Journal of biological chemistry.

[6]  J. Shoji,et al.  Studies on tsushimycin. II. The structures of constituent fatty acids. , 1969, The Journal of antibiotics.

[7]  K. Bloch Enzymic synthesis of monounsaturated fatty acids , 1969 .

[8]  A. Fulco The biosynthesis of unsaturated fatty acids by bacilli. I. Temperature induction of the desaturation reaction. , 1969, The Journal of biological chemistry.

[9]  P. Capella,et al.  Determination of double bond position in monounsaturated fatty acid esters by mass spectrometry of their trimethylsilyloxy derivatives , 1968 .

[10]  G. Gottschalk The stereospecificity of the citrate synthase in sulfate-reducing and photosynthetic bacteria. , 1968, European journal of biochemistry.

[11]  D. Hunneman,et al.  Gas chromatographic—mass spectrometric studies of long chain hydroxy acids.—III.1 The mass spectra of the methyl esters trimethylsilyl ethers of aliphatic hydroxy acids. A facile method of double bond location , 1968 .

[12]  K. Bloch,et al.  Beta-hydroxydecanoyl thioester dehydrase. II. Mode of action. , 1967, The Journal of biological chemistry.

[13]  J. Postgate,et al.  Classification of Desulfovibrio species, the nonsporulating sulfate-reducing bacteria. , 1966, Bacteriological reviews.

[14]  A. T. James,et al.  The lipids and fatty acid metabolism of photosynthetic bacteria. , 1965, Biochimica et biophysica acta.

[15]  V. P. Skipski,et al.  Separation of lipid classes by thin-layer chromatography. , 1965, Biochimica et biophysica acta.

[16]  K. Bloch,et al.  Unsaturated fatty acids in microorganisms. , 1962, The Journal of biological chemistry.

[17]  R. Ryhage,et al.  Mass spectrometry in lipid research. , 1960, Journal of lipid research.

[18]  W. J. Dyer,et al.  A rapid method of total lipid extraction and purification. , 1959, Canadian journal of biochemistry and physiology.

[19]  Richard E. Dickerson,et al.  7 Cytochromes c , 1975 .

[20]  D. Zakim,et al.  Membrane fluidity and the regulation of membrane-bound enzymes. , 1974, Horizons in biochemistry and biophysics.

[21]  N Shaw,et al.  Lipid composition as a guide to the classification of bacteria. , 1974, Advances in applied microbiology.

[22]  V. Braun,et al.  Biochemistry of bacterial cell envelopes. , 1974, Annual review of biochemistry.

[23]  J. Postgate,et al.  The Physiology of Sulphate-Reducing Bacteria , 1973 .

[24]  J. Erwin Lipids and biomembranes of eukaryotic microorganisms , 1973 .

[25]  J. Erwin CHAPTER 2 – Comparative Biochemistry of Fatty Acids in Eukaryotic Microorganisms , 1973 .

[26]  K. Mogi,et al.  CELLULAR FATTY ACID SPECTRA OF PEDIOCOCCUS SPECIES IN RELATION TO THEIR TAXONOMY , 1972 .

[27]  Vosjan Jh ATP generation by electron transport in Desulfovibrio desulfuricans. , 1970 .

[28]  J. Vosjan ATP generation by electron transport in Desulfovibrio desulfuricans. , 1970, Antonie van Leeuwenhoek.

[29]  J. McCloskey,et al.  Characterization of unsaturated hydrocarbons by mass spectrometry , 1966 .

[30]  EDWIN C. Webb The Enzymes , 1961, Nature.

[31]  D. Barton,et al.  408. Colombo root bitter principles. Part I. The functional groups of Columbin , 1956 .

[32]  R. Criegee Osmiumsäure‐ester als Zwischenprodukte bei Oxydationen , 1936 .

[33]  B. Nori Antagonistic Effects of Myxococcus xanthus on Fungi: II. Isolation and Characterization of Inhibitory Lipid Factors , 2022 .