Characterization and metabolism of free fatty alcohols from<i>Escherichia coli</i>

Naccarato, William F.; Gelman, Rose A.; Kawalek, Joseph C.; Gilbertson, John R.

doi:10.1007/bf02532644

Cited by 33 publications

(17 citation statements)

References 21 publications

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“…Further investigations are necessary to verify this, and to explore the extent to which waxes occur in bacteria. The presence of fatty alcohols in the Gram-negative Serratia rnarcescens (Kates, Adams & Martin, 1964) and Escherichia coli (Naccarato et al, 1972(Naccarato et al, , 1974 and in the Gram-positive Bacillus cereus (Kates, Kushner & James, 1962)~ indicates that true waxes may be more widely distributed among bacteria than has previously been recognized.…”

Section: Discussionmentioning

confidence: 95%

Occurrence and Patterns of Waxes in Neisseriaceae

Bryn¹,

Jantzen²,

Bøvre

1977

Journal of General Microbiology

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Forty-five strains classified in the family Neisseriaceae were analysed for wax esters by gas-liquid chromatography. The amounts and types of waxes varied between the taxa. Waxes were not detected in 16 strains of 'true neisseriae' (genus Neisseria) or in two strains of Kingella, but they were found in all 'false neisseriae', in all species of Moraxella except Moraxellaphenylpyrouvica, in five out of 10 strains of Acinetobacter, and in all strains of a group of psychrophilic, oxidase-positive organisms. The chain lengths of the wax esters ranged from Cz4 to C4*, with CS6 predominating. In all taxa, esters with even numbers of carbon atoms constituted 70 to roo % of the total. Saturated, mono-unsaturated and diunsaturated waxes were found. Acinetobacter strains were characterized by large amounts (30 to 98 %) of di-unsaturated wax esters; such waxes did not exceed 8 % in the 'false neisseriae ' or Moraxella spp. Waxes of strains belonging to the psychrophilic, oxidasepositive group generally resembled those found in Moraxella. Wax esters with odd numbers of carbon atoms were abundant in M. lacunata (29 %), M. atlantae (15 %) and in the psychrophilic group (19 to 28 %); long-chain esters (C40 or above) were characteristic of M . atlantae (30 %) and one strain of M . osloensis (26 %).

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Section: Discussionmentioning

confidence: 95%

Occurrence and Patterns of Waxes in Neisseriaceae

Bryn¹,

Jantzen²,

Bøvre

1977

Journal of General Microbiology

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“…The mycoplasmas for this study were Purity of long-chain alcohols was assessed by thinlayer and gas-liquid chromatographies (10). In each instance, these alcohols were only one compound on thin-layer chromatography and were greater than 95% one moiety as judged by gas-liquid chromatography.…”

Section: Methodsmentioning

confidence: 99%

Inactivation of mycoplasmas by long-chain alcohols

Fletcher¹,

Gilbertson²,

Albers³

et al. 1981

Antimicrob Agents Chemother

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In this report, we describe the inhibitory activity of long-chain alcohols on the growth of Mycoplasma gallisepticum and Mycoplasma pneumoniae. Peak inhibition was recorded with saturated primary alcohols (64 ,uM) varying in chain length from 16 to 19 carbon atoms. The unsaturated alcohols (oleyl, linoleyl, and linolenyl) and the secondary alcohol (pentadecan-2-ol), when employed in the same test conditions, were considerably less effective growth inhibitors than the primary saturated alcohols. Stearic and palmitic acids were also ineffective as growth inhibitors of M. pneumoniae and M. gallisepticum at a 128 ,uM concentration. Because these antimycoplasma agents are fatty alcohols and cholesterol is known to be required for the growth of some mycoplasmas, additional cholesterol was added in an attempt to reverse the inhibition observed with these agents. Cholesterol at a 128 ,uM concentration did not significantly relieve the growth inhibition observed with stearyl alcohol at a 48 ,uM concentration. Mammalian cell cultures were found to be significantly more resistant to the effects of these inhibitory alcohols than were the mycoplasmas. Electron micrographs showed that inclusion of stearyl alcohol in the culture medium produced changes in the cellular morphology of the treated mycoplasmas.In previous studies, it has been shown that inhibition of the biosynthesis of primary longchain alcohols in mammalian and some bacterial cells is associated with a decrease in growth rate (4,5,11). In regard to the long-chain alcohols, it was reported by Snipes et al. (16) that saturated primary alcohols, 10 and 11 carbon atoms in chain length, inhibit the growth of lipid-containing viruses. Subsequently, Sands et al. (15) demonstrated even greater viricidal activity with long-chain unsaturated monoglycerides and primary alcohols. These reports stimulated our interest in the effect of long-chain alcohols on the growth of mycoplasmas. The results presented in this manuscript demonstrate that inclusion of small concentrations (64 ,uM) of certain saturated long-chain primary alcohols in the culture medium inhibits the growth of Mycoplasma pneumoniae and Mycoplasma gallisepticum. MATERIALS AND METHODSThe mycoplasmas for this study were obtained as follows-M. pnesmoniae (15293) from the American Type Culture Colleetion and M. gallisepticum (K781-4) from S. H. lieven. These microorganisms were grown in mycoplasma broth (Difco Laboratories) with supplements (2).Purity of long-chain alcohols was assessed by thinlayer and gas-liquid chromatographies (10). In each instance, these alcohols were only one compound on thin-layer chromatography and were greater than 95% one moiety as judged by gas-liquid chromatography.Because the long-chain alcohols are insoluble in water, they were dissolved in 95% ethanol and added in microliter portions to the supplemented mycoplasma medium. The final concentration of ethanol in the cultures was less than 1% (vol/vol), and this percentage of ethanol was not toxic for the species of Mycoplasma studied....

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“…Only some bacteria of the genera Mycobacterium (6), Streptomyces (29), and Rhodococcus (3,5,50) accumulate triacylglycerols. Wax esters, which are trace constituents of numerous bacteria (e.g., Escherichia coli [28], Serratia marcescens, Bacillus cereus [22], Nocardia sp. [21], and Thiobacillus thioparus [15]), are generally considered as widespread energy storage components in the genus Acinetobacter (18).…”

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confidence: 99%

Production of a Polyunsaturated Isoprenoid Wax Ester during Aerobic Metabolism of Squalene by Marinobacter squalenivorans sp. nov

Rontani¹,

Mouzdahir

Michotey³

et al. 2003

Appl Environ Microbiol

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This paper describes the production of 5,9,13-trimethyltetradeca-4E,8E,12-trienyl-5,9,13-trimethyltetradeca-4E,8E,12-trienoate during the aerobic degradation of squalene by a Marinobacter strain, 2Asq64, isolated from the marine environment. A pathway involving initial cleavage of the C 10 -C 11 or C 14 -C 15 double bonds of the squalene molecule is proposed to explain the formation of this polyunsaturated isoprenoid wax ester. The isoprenoid wax ester content reached 1.1% of the degraded squalene at the mid-exponential growth phase and then decreased during the stationary phase. The wax ester content increased by approximately threefold in N-limited cultures, in which the ammonium concentration corresponds to conditions often found in marine sediments. This suggests that the bacterial formation of isoprenoid wax esters might be favored in such environments. The bacterial strain is then characterized as a member of a new species, for which we propose the name Marinobacter squalenivorans sp. nov.The microbial communities of marine environments are often exposed to fluctuating conditions such as the availability of nutrients. Microorganisms have developed a variety of strategies that allow them to survive in these variable environments; the accumulation of storage lipids is only one of them (4). Storage compounds occur normally as intracellular inclusions in bacteria (42). While the accumulation of triacylglycerols occurs preferentially in eukaryotic organisms, triacylglycerols are not frequently found as storage compounds in bacteria (4). Bacteria usually accumulate specialized lipids such as poly(3-hydroxybutyric acid) or other polyhydroxyalkanoic acids (31,44,45). Only some bacteria of the genera Mycobacterium (6), Streptomyces (29), and Rhodococcus (3, 5, 50) accumulate triacylglycerols. Wax esters, which are trace constituents of numerous bacteria (e.g., Escherichia coli [28], Serratia marcescens, Bacillus cereus [22], Nocardia sp. [21], and Thiobacillus thioparus [15]), are generally considered as widespread energy storage components in the genus Acinetobacter (18). In fact, it was previously demonstrated that different strains of A. calcoaceticus increased their wax ester contents in N-limited cultures and that the accumulated wax esters were degraded to water-soluble molecules and CO 2 during C starvation (18). These results showed that these compounds may serve as an ATP-generating substrate during starvation.We previously observed the production of several isoprenoid wax esters during the aerobic degradation of 6,10,14-trimethylpentadecan-2-one and phytol by four bacteria (Acinetobacter sp. strain PHY9, Pseudomonas nautica [IP85/617], Marinobacter sp. strain CAB [DSMZ11874], and Marinobacter hydrocarbonoclasticus [ATCC49840]) isolated from the marine environment (33). The amount of these esters increased considerably in N-limited cultures, in which the ammonium concentration corresponds to conditions often found in marine sediments. Similar isoprenoid wax esters have also been detected during the degrada...

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Characterization and metabolism of free fatty alcohols fromEscherichia coli

Cited by 33 publications

References 21 publications

Occurrence and Patterns of Waxes in Neisseriaceae

Occurrence and Patterns of Waxes in Neisseriaceae

Inactivation of mycoplasmas by long-chain alcohols

Production of a Polyunsaturated Isoprenoid Wax Ester during Aerobic Metabolism of Squalene by Marinobacter squalenivorans sp. nov

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