13-methyltetradecanoic Acid Research Articles

Acidobacterium capsulatum gen. nov., sp. nov.: An acidophilic chemoorganotrophic bacterium containing menaquinone from acidic mineral environment

Acidobacterium is proposed as a new genus for the acidophilic, chemoorganotrophic bacteria containing menaquinone isolated from acidic mineral environments.Acidobacterium capsulatum is proposed for the singleAcidobacterium species which consists of eight strains (Biogroup 5). The members of this species are gram-negative, aerobic, mesophilic, non-spore-forming, capsulated, saccharolytic, and rod-shaped bacteria. They are motile by peritrichous flagella. They can grow between pH 3.0 and 6.0, but not at pH 6.5. They give positive results in tests for esculin hydrolysis, catalase, and β-galactosidase. Oxidase and urease are negative. They can use glucose, cellobiose, starch, maltose, or β-gentiobiose as a sole carbon source, but cannot use elemental sulfur and ferrous iron as an energy source. The DNA base composition is 59.7–60.8 guanine plus cytosine (G+C) mol%. The major isoprenoid quinone is menaquinone with eight isoprene units (MK-8). The major fatty acid is 13-methyltetradecanoic acid. DNA relatedness between this species and the species ofAcidiphilium, Acidomonas, andDeinobacter was 18 to 2%. From phenotypic and chemotaxonomic characters, these member do not belong to any known taxa of gram-negative bacteria. A culture of the type strain (strain 161) has been deposited in the Japan Collection of Microorganisms as JCM 7670.

Fatty Acid Composition of Propionibacterium propionicum (Arachnia propionica)

The cellular fatty acids of Arachnia propionica are largely 13-methyltetradecanoic acid (Ci15:0) and 12-methyltetradecanoic acid (Ca15:0); thus, the fatty acid pattern of this organism resembles the pattern found in propionibacteria. This finding supports the transfer of members of the genus Arachnia to the genus Propionibacterium.

Mixed monolayers of straight and branched chain fatty acids Part 1: Mixed monolayers of n-tridecanoic, n-tetradecanoic and n-pentadecanoic acids with the iso-fatty acids 13-methyltetradecanoic acid, 14-methylpentadecanoic acid, 15-methylhexadecanoic acid, 16-methylheptadecanoic acid and 17-methyloctadecanoic acid

A study has been initiated to investigate the behavior of mixed straight-chain/iso-branched-chain fatty acid monolayer systems. In this publication we examine the effects of changing the iso-branched chain length while maintaining the chain-length of the straight-chain fatty acid constant. Three straight-chain fatty acids were selected: n-tridecanoic, n-tetradecanoic and n-pentadecanoic acid. The second component, iso-branched fatty acids selected were 13-methyltetradecanoic, 14-methylpentadecanoic, 15-methylhexadecanoic, 16-methylheptadecanoic and 17-methyloctadecanoic. The behavior of these systems is characterized primarily in terms of the shift of the liquid expanded/liquid condensed phase transition of the straight-chain acid produced by the addition of the iso-branched acids. The shifts are compared in terms of a relative chain-length number which is defined as the number of carbon atoms by which the pentadecanoic acid exceeds, or falls short of the branching carbon atom of the iso-branched acid. The shifts of the straight-chain acid phase change were found to range from large positive to smaller negative surface pressure changes as the relative chain-length number changed from +2 to −2. The two phase region width showed a corresponding dependency. Finally, it was found that, in spite of compensatory factors, the internal energies of the liquid expanded/liquid condensed phase change for iso-branched acids are much smaller than those of the corresponding straight-chain acids and for the mixed systems the (negative) values of the internal energy change increase as the iso-branched chain increases in length. This latter observation shows that the effects of chain branching decrease with an increase in the overall branched chain length or a decrease in the relative chain-length number.

Polar Lipids, Fatty Acids, and Isoprenoid Quinones of Alteromonas putrefaciens ( Shewanella putrefaciens)

The polar lipids, fatty acids, and isoprenoid quinones of eight strains of Alteromonas putrefaciens (Shewanella putrefaciens) representing different phenotypes and genotypes have been analysed. The polar lipids consisted almost entirely of phosphatidylethanolamine and phosphatidylglycerol, with variable proportions of their lyso derivatives (such derivatives were most prominent in extracts from strains of relatively high mol % G+C). In contrast to the results of previous studies, ornithine amide lipids and glycolipids were not encountered. Fatty acid profiles were complex, usually with 13-methyltetradecanoic acid, pentadecanoic acid, cis-hexadec-9-enoic acid, and ds-heptadec-9-enoic acid as the major components. All strains contained ubiquinone-8 and ubiquinone-7, with the former preponderant in all strains but one. In addition all strains contained menaquinone-7 (a trace only in one strain) and its methyl derivative thermoplasmaquinone-7 (traces only in two strains). Thus, rather diverse strains of A. putrefaciens share an overall lipid profile highly unusual for a Gram-negative bacterium, and distinctively different from that of recognized Alteromonas species. The classification of the organism as Shewanella putrefaciens within Vibrionaceae does not eliminate this chemotaxonomic problem.

Lipid and Wall Amino Acid Composition in the Classification and Identification of Arachnia propionica

Two strains of Arachnia propionica and two Arachnia-like isolates were degraded by alkaline methanolysis and the non-hydroxylated fatty acid esters released were examined by thin-layer and gas chromatography. The fatty acid profiles obtained were both qualitatively and quantitatively similar and were comprised of iso-, anteiso- and straight chain saturated fatty acids with 13-methyltetradecanoic acid ( i-15) and 12-methyltetradecanoic acid ( ai-15) as major components. One of the Arachnia-like strains (HIK 288) had, in addition to i-15 and ai-15, major amounts of pentadecanoic acid (15:0). All of the strains gave characteristic polar lipid patterns consisting of diphosphatidylglycerol, phosphatidylglycerol and two incompletely characterised glycolipids. Analyses of wall amino acid preparations by gas and thin-layer chromatography showed that Arachnia propionica strains contain major amounts of alanine, glycine, glutamic acid and LL-diaminopimelic acid. The chemical data support the integrity of Arachnia propionica and provide a valuable means of differentiating it from morphologically and physiologically similar strains of Actinomyces israelii.

Difference in packing properties between iso and anteiso methyl-branched fatty acids as revealed by incorporation into the membrane lipids of Acholeplasma laidlawii strain A

Acholeplasma laidlawii strain A was grown on the long-chain, branched, saturated fatty acids 12-methyltetradecanoic acid (anteiso-C 15), 14-methylhexadecanoic acid (anteiso-C 17), 13-methyltetradecanoic acid (iso-C 15) and 15-methylhexadecanoic acid (iso-C 17), and on the branched-chain fatty acid precursors 2-methylbutanoic acid (anteiso-C 5) and 3-methylbutanoic acid (iso-C 5). The membrane lipid composition as a function of the fatty acid supplement and the growth temperature was determined: (1) The ratio between the two dominating lipids, monoglucosyldiacylglycerol and diglucosyldiacylglycerol, is decreased when anteiso acyl chains replace iso acyl chains in the lipids, and when the acyl chains are elongated from 15 to 17 carbon atoms; (2) the ratio iso / anteiso acyl chains is reduced when the growth temperature is decreased; (3) the average length of the de novo synthesized branched fatty acids is decreased when the growth temperature is lowered, and when anteiso-C 5 is exchanged for iso-C 5 in the growth medium. The lipid regulation mechanisms are interpreted in terms of lipid molecular geometry and self-assembly of lipid molecules. It is concluded that iso and anteiso fatty acids have distinctively different packing properties in a biological membrane, and they mimic straight-chain saturated and cis-monounsaturated fatty acids, respectively, as seen by the way they affect the physicochemical properties of membrane lipids and by the way they are used in lipid regulation mechanisms.

Cellular Fatty Acid Compositions of Moraxella anatipestifer and Legionella pneumophila

In contrast to results from a recent study, we found the fatty acid composition of Legionella pneumophila to be distinct from the fatty acid composition of Moraxella anatipestifer. M. anatipestifer contained large amounts (50%) of 13-methyltetradecanoic acid and smaller amounts (5 to 22%) of branched-chain hydroxy acids, whereas L. pneumophila contained 14-methylpentadecanoic acid as the major component (30%), with no or trace amounts (<1%) of 13-methyltetradecanoic and hydroxy acids. Similar fatty acid results were obtained on two different growth media.

Differentiation of actinobacillus actinomycetemcomitans from haemophilus aphrophilus by gas chromatography of hexane extracts from whole cells

In the present study, differentiation of the closely related bacteria Actinobacillus actinomycetemcomitans and Haemophilus aphrophilus has been made possible through gas chromatography of hexane extracts from their whole cells. While the investigated strains of H. aphrophilus were homogeneous, A. actinomycetemcomitans could be divided into three clusters of strains according to their gas chromatographic fingerprints. Myristic, palmitic and palmitoleic acid were major fatty acids in both A. actinomycetemcomitans and H. aphrophilus. In strain cluster III of A. actinomycetemcomitans, 13-methyltetradecanoic acid occurred as a fourth major fatty acid. Essentially no minor components were detected in cluster I of A. actinomycetemcomitans and in H. aphrophilus. In cluster II, the presence of minor components was moderate, in cluster III, marked.

Lipids in the classification of Nocardioides: reclassification of Arthrobacter simplex (Jensen) lochhead in the genus Nocardioides (Prauser) emend. O'Donnell et al. as Nocardioides simplex comb. nov.

Representative strains of Nocardioides, Arthrobacter simplex and Arthrobacter tumescens were degraded by acid methanolysis and the fatty acid esters released examined by thin-layer and gas chromatography. Branched-chain 14-methylpentadecanoic acid (iso-16) was the predominant component in all but one of the Nocardioides strains. Arthrobacter simplex also contained major amounts of this acid whereas A. tumescens had only minor amounts. All of the test strains possessed 15 and 17 carbon straight chain acids, tuberculostearic acid (10-methyloctadecanoic acid) and its 17 and 18-carbon homologues. The fatty acid profiles of Nocardioides strains lacked 13-methyltetradecanoic and heptadecanoic acids which were both present in Arthrobacter simplex and Arthrobacter tumescens. The profiles of these latter organisms were quantitatively different from each other. The polar lipids of the test strains all contained diphosphatidylglycerol and phosphatidylglycerol but only Arthrobacter tumescens contained phosphatidylinositol and three unidentified polar lipids. Nocardioides and Arthrobacter simplex strains all contained two very characteristic closely related polar lipids. All of the test strains contained tetrahydrogenated menaquinones with eight isoprene units as the major isoprenologue. The results of the present study support the integrity of the genus Nocardioides and provide a reliable way of distinguishing it from other actinomycetes, such as Streptomyces, which also have LL-diaminopimelic acid and glycine in the peptidoglycan. The lipid data, together with results from chemical, genetic and phage host range studies, provide sufficient grounds for the transfer of Arthrobacter simplex to Nocardioides as Nocardioides simplex comb. nov. An emended description of the genus Nocarioides is given.

The use of 13-methyltetradecanoic acid as an indicator of adipose tissue turnover.

We show in this paper that 13-methyltetradecanoic acid (13-MTD) can be used as a structually labeled marker for investigating the mobility of fatty acyl chains in adipose tissue in the rat. The presence of an omega-1 methyl group allows easy quantitation by gas liquid chromatography (GLC) and permits an assessment to be made of any oxidation and chain elongation reactions with reincorporation of the label into the adipose tissue, since the iso-acyl chain is well resolved from odd or even-numbered homologous fatty acids with straight chains. The kinetics of uptake and loss of the structural label were different for adipose tissue taken from the various sites which were sampled, namely post abdominal, mesenteric, perirenal, pericardiac and subcutaneous adipose tissue as well as the epidydimal fat pads. We also report preliminary results in man which confirm that the method is applicable to human clinical studies and that 13-MTD kinetics differ for adipose tissue taken from the 3 different subcutaneous sites--waist, arm and thigh.

Occurrence of 2‐ and 3‐hydroxy fatty acids in high concentrations in the extractable and bound lipids ofFlavobacterium meningosepticum andFlavobacterium IIb

The major hydroxy fatty acids of cellular lipids in Flavobacterium meningosepticum and Flavobacterium sp. King's group UUb were identified as 2-hydroxy 13-methyltetradecanoic, 3-hydroxy 13-methyltetradecanoic, 3-hydroxy palmitic, and 3-hydroxy 15-methylhexadecanoic acids using gas chromatography-mass spectrometry and GC-mass fragmentography. The concentration of these hydroxy fatty acids comprised up to 30-40% of the total extractable and 20-30% of the bound lipid fatty acids, respectively. From the stability for mild alkaline hydrolysis, 2-hydroxy fatty acids seemed to be attached with ester linkage, and 3-hydroxy fatty acids with amide linkage.

Occurrence of positional isomers of octadecenoic and hexadecenoic acids in human depot fat

Positional isomers of hexadecenoic aud octadecenoic acids of human adipose tissue have been separated by gas-liquid chromatography and their amounts determined by oxidative cleavage (MnO(4) and IO(4)). The following isomeric octadecenoic acids were present: 7-octadecenoic acid (0.4%), 8- (1.9%), 9- (73.0%), 10- (2.5%), 11- (19.0%) and 12- (3.2%). The hexadecenoic acids have also been shown to be a mixture of positional isomers, in which the cis-9-isomer predominates. 10-Hexadecenoic and 12-octadecenoic acids could conceivably be precursors of linoleic acid. The following branched fatty acids have also been determined in human depot fat: 13-methyltetradecanoic, 12-methyltetradecanoic, 14-methylpentadecanoic, 14-methylhexadecanoic, and 16-methylheptadecanoic acid. They were present in percentages of 0.02-0.6% and their identification rests solely on comparison of their gas-liquid chromatographic retention times with those of synthetic compounds.

Biosynthesis of branched-chain fatty acids. IV. Factors affecting relative abundance of fatty acids produced by Bacillus subtilis.

The fatty acids produced by Bacillus subtilis may be grouped into four pairs: 12-methyltetradecanoic and 14-methylhexadecanoic acids (anteiso-C15and anteiso-C17), 13-methyltetradecanoic and 15-methylhexadecanoic acids (iso-C15and iso-C17), 12-methyltridecanoic and 14-methylpentadecanoic acids (iso-C14and iso-C16), and myristic and palmitic acids (n-C14and n-C16). Any one of the branched-chain amino acids, L-isoleucine, L-leucine, or L-valine, or of the branched short-chain fatty acids, α-methylbutyrate, isovalerate, or isobutyrate, added to the glucose – yeast extract medium increased the synthesis of the specific pairs of fatty acids structurally related to the added substrate and decreased the synthesis of other fatty acids. This indicates that the relative abundance of branched-chain fatty acids in B. subtilis is a function of the relative availability of the precursors of the terminal portions of the fatty acids, presumably α-methylbutyryl-CoA, isovaleryl-CoA, and isobutyryl-CoA. This mechanism is consistent with the relative abundances of branched-chain fatty acids found in mutants of B. subtilis which require particular branched-chain amino acids. The biotin content of the culture medium and the length of incubation time also affected the relative abundance of the fatty acids.

The branched-chain fatty acids of butterfat. IV. The isolation of (+)-12-methyltetradecanoic acid and of 13-methyltetradecanoic acid.

Research Article| June 01 1954 The branched-chain fatty acids of butterfat. 4. The isolation of (+)-12-methyltetradecanoic acid and of 13-methyltetradecanoic acid R. P. Hansen; R. P. Hansen 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar F. B. Shorland; F. B. Shorland 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar N. June Cooke N. June Cooke 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar Biochem J (1954) 57 (2): 297–301. https://doi.org/10.1042/bj0570297 Views Icon Views Article contents Figures & tables Video Audio Supplementary Data Peer Review Share Icon Share Facebook Twitter LinkedIn MailTo Cite Icon Cite Get Permissions Citation R. P. Hansen, F. B. Shorland, N. June Cooke; The branched-chain fatty acids of butterfat. 4. The isolation of (+)-12-methyltetradecanoic acid and of 13-methyltetradecanoic acid. Biochem J 1 June 1954; 57 (2): 297–301. doi: https://doi.org/10.1042/bj0570297 Download citation file: Ris (Zotero) Reference Manager EasyBib Bookends Mendeley Papers EndNote RefWorks BibTex toolbar search Search Dropdown Menu toolbar search search input Search input auto suggest filter your search All ContentAll JournalsBiochemical Journal Search Advanced Search This content is only available as a PDF. © 1954 CAMBRIDGE UNIVERSITY PRESS1954 Article PDF first page preview Close Modal You do not currently have access to this content.

The branched-chain fatty acids of mutton fat. II. The isolation of (+)-12-methyltetradecanoic acid and the 13-methyltetradecanoic acid.

The branched-chain fatty acids of mutton fat. II. The isolation of (+)-12-methyltetradecanoic acid and the 13-methyltetradecanoic acid.