Ornithine lipid of Mycobacterium tuberculosis: its distribution in some slow- and fast-growing mycobacteria

Lanéelle, Marie‐Antoinette; Promé, Danièlle; Lanéelle, Gilbert; Promé, Jean‐Claude

doi:10.1099/00221287-136-4-773

Cited by 30 publications

(16 citation statements)

References 15 publications

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“…It exists widely in outer (mainly) and inner cell membranes (Wilkinson et al. 1982; Laneelle et al. 1990), with the exception of the strain Myroides sp.…”

Section: Discussionmentioning

confidence: 99%

Isolation and characterization of a novel biosurfactant produced by hydrocarbon-degrading bacteriumAlcanivorax dieseloleiB-5

Qiao

Shao

2010

Journal of Applied Microbiology

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Aims: Our goal was to identify a novel biosurfactant produced by a marine oil‐degrading bacterium. Methods and Results: Biosurfactants were produced by Alcanivorax dieselolei strain B‐5T growing with diesel oil as the sole carbon and energy source. Culture supernatant was first extracted with chloroform/methanol (1 : 1, v/v), then further purified step by step with a normal phase silica gel column, a Sephadex LH20 gel column and a preparative thin layer plate. The main component was determined to be a lipopeptide; it was chemically characterized with nuclear magnetic resonance, liquid chromatography‐quadrupole ion‐trap mass spectrometry, amino acid analysis and GC–MS and was found to be a mixture of proline lipids. The monomers of the proline lipids were composed of a proline residue and a fatty acid (C14:0, C16:0 or C18:0). The critical micelle concentration of the mixed proline lipids was determined to be 40 mg l−1. Moreover, activity variations in ranges of pH, temperature and salinity were also detected and showed reasonable stability. Conclusions: Alcanivorax dieselolei B‐5 produced a novel linear lipoamino biosurfactant, characterized as a proline lipid. Significance and Impact of the Study: A proline lipid was characterized for the first time as a bacterial biosurfactant. This product has potential in both environmental and industrial applications.

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“…It exists widely in outer (mainly) and inner cell membranes (Wilkinson et al. 1982; Laneelle et al. 1990), with the exception of the strain Myroides sp.…”

Section: Discussionmentioning

confidence: 99%

Isolation and characterization of a novel biosurfactant produced by hydrocarbon-degrading bacteriumAlcanivorax dieseloleiB-5

Qiao

Shao

2010

Journal of Applied Microbiology

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“…Similar to betaines and sulfolipids, OLs are formed under conditions of phosphorous stress (Minnikin et al, 1972). It now appears that OLs are widespread phylogenetically in bacteria, appearing in Firmicutes, Mycobacteria, a variety of Proteobacteria, and perhaps other phyla (Kawai et al, 1988;Laneelle et al, 1990;Lopez-Lara et al, 2003). It now appears that OLs are widespread phylogenetically in bacteria, appearing in Firmicutes, Mycobacteria, a variety of Proteobacteria, and perhaps other phyla (Kawai et al, 1988;Laneelle et al, 1990;Lopez-Lara et al, 2003).…”

Section: Polar Head Groupsmentioning

confidence: 99%

Lipidomics for Geochemistry

Pearson

2014

Treatise on Geochemistry

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“…The 3-OH-FAs were composed of 3-OH-C 16 , 3-OH-C 18 and 3-OH-C 20 ; small amounts of 3-OH-C 22 were also detected. It has to be noted that in the mycobacterial world straight-chain 3-OH-FAs have been previously described only, in an amide-linked form, in ornithine-containing lipids (19) and C-mycoside type glycopeptidolipids of some mycobacterial species (8). To the best of our knowledge, the present study is the first report of the presence of an esterlinked straight-chain 3-OH-FA-containing lipid in mycobacteria.…”

Section: Vol 177 1995 Notes 4567mentioning

confidence: 99%

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

et al. 1995

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In a previous study (S. Alugupalli, F. Portaels, and L. Larsson, J. Bacteriol. 176:2962-2969, 1994), we reported the occurrence of 21 3-hydroxy fatty acids (3-OH-FAs) in the methanolysis products of different mycobacterial species. The present study was undertaken in order to chemically characterize the ester-linked complex native forms of these acids in Mycobacterium tuberculosis. Three 3-OH-FA-containing lipids were purified by chromatography and analyzed by one-and two-dimensional nuclear magnetic resonance spectroscopy, by fast atom bombardment-mass spectrometry, and by various conventional chemical analysis techniques. 3-OH-2,4,6-trimethyl-FAs were found in 2,3-diacyl trehalose and 2,3,6,6 -tetra-acyl-2 -sulfate trehalose (sulfatide I), two specific glycolipids of the tubercle bacillus, explaining the specific occurrence of these fatty acids in the methanolysis products of virulent strains of M. tuberculosis. Straight-chain 3-OH-FAs were localized in phosphatidyl ethanolamine but not in the other phospholipids, suggesting a possible role of this class of phospholipids in the metabolism of fatty acids in actinomycetes.Tuberculosis remains the leading cause of death in the world from a single pathogen (7,18). The slow growth of the tubercle bacillus and the lack of easy and reliable tests for detecting the disease at an early stage also limit the program of control and eradication of tuberculosis. In this context, recent efforts have been devoted to more knowledge of the disease and its pathogen.Most of the unique features of mycobacteria, such as their mold-like growth pattern and their resistance to chemical agents, as well as many of their biologic activities have been attributed to their high lipid content (17). Detailed chemical studies demonstrated the diversity and the complexity of the mycobacterial fatty acids, which have been used in chemotaxonomy in order to discriminate among mycobacterial species (4,8,24). These compounds include 2-alkyl branched, 3-hydroxylated long chain fatty acids (up to 90 carbon atoms), the so-called mycolic acids, multi-methyl (Me) branched-chain fatty acids having chiral centers with an L or D configuration, and ␣,␤-unsaturated compounds. We recently characterized 21 3-hydroxy fatty acids (3-OH-FAs), i.e., straight-chain and 2-Me and 2,4,6-tri-Me branched-chain fatty acids, in 27 strains belonging to 12 mycobacterial species (2). According to their 3-OH-FA patterns, the mycobacterial species could be subdivided into six groups, suggesting a taxonomic interest for these fatty acids. Virulent strains of Mycobacterium tuberculosis exhibited an unique pattern of 3-OH-FAs in that they contain multi-Me branched long chain hydroxy fatty acids, the potential precursors of fatty acids found in the biologically important mycobacterial lipids (4, 24). The present study was undertaken in order to chemically characterize the ester-linked native forms of straight-and Me branched-chain 3-OH-FAs in M. tuberculosis.M. tuberculosis H37Rv was grown for 4 weeks on Sauton's medium (26) as sur...

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Ornithine lipid of Mycobacterium tuberculosis: its distribution in some slow- and fast-growing mycobacteria

Cited by 30 publications

References 15 publications

Isolation and characterization of a novel biosurfactant produced by hydrocarbon-degrading bacteriumAlcanivorax dieseloleiB-5

Isolation and characterization of a novel biosurfactant produced by hydrocarbon-degrading bacteriumAlcanivorax dieseloleiB-5

Lipidomics for Geochemistry

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

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