scholarly journals Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

2003 ◽  
Vol 69 (7) ◽  
pp. 3892-3900 ◽  
Author(s):  
Chi Ming So ◽  
Craig D. Phelps ◽  
L. Y. Young
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Degradation Mechanism ◽  
Acyl Chain ◽  
Chain Elongation ◽  
Initial Attack ◽  
Alkane Degradation ◽  
Sulfate Reducing ◽  
Bacterium Strain ◽  
Alkane Chain

ABSTRACT Strain Hxd3, an alkane-degrading sulfate reducer previously isolated and described by Aeckersberg et al. (F. Aeckersberg, F. Bak, and F. Widdel, Arch. Microbiol. 156:5-14, 1991), was studied for its alkane degradation mechanism by using deuterium and 13C-labeled compounds. Deuterated fatty acids with even numbers of C atoms (C-even) and 13C-labeled fatty acids with odd numbers of C atoms (C-odd) were recovered from cultures of Hxd3 grown on perdeuterated pentadecane and [1,2-13C2]hexadecane, respectively, underscoring evidence that C-odd alkanes are transformed to C-even fatty acids and vice versa. When Hxd3 was grown on unlabeled hexadecane in the presence of [13C]bicarbonate, the resulting 15:0 fatty acid, which was one carbon shorter than the alkane, incorporated a 13C label to form its carboxyl group. The same results were observed when tetradecane, pentadecane, and perdeuterated pentadecane were used as the substrates. These observations indicate that the initial attack of alkanes includes both carboxylation with inorganic bicarbonate and the removal of two carbon atoms from the alkane chain terminus, resulting in a fatty acid one carbon shorter than the original alkane. The removal of two terminal carbon atoms is further evidenced by the observation that the [1,2-13C2]hexadecane-derived fatty acids contained either two 13C labels located exclusively at their acyl chain termini or none at all. Furthermore, when perdeuterated pentadecane was used as the substrate, the 14:0 and 16:0 fatty acids formed both carried the same numbers of deuterium labels, while the latter was not deuterated at its carboxyl end. These observations provide further evidence that the 14:0 fatty acid was initially formed from perdeuterated pentadecane, while the 16:0 fatty acid was produced after chain elongation of the former fatty acid with nondeuterated carbon atoms. We propose that strain Hxd3 anaerobically transforms an alkane to a fatty acid through a mechanism which includes subterminal carboxylation at the C-3 position of the alkane and elimination of the two adjacent terminal carbon atoms.

In vivo study of the biosynthesis of long-chain fatty acids using deuterated water

1995 ◽  
Vol 269 (2) ◽  
pp. E247-E252 ◽  
Author(s):  
H. O. Ajie ◽  
M. J. Connor ◽  
W. N. Lee ◽  
S. Bassilian ◽  
E. A. Bergner ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
De Novo ◽  
Chain Elongation ◽  
Deuterated Water ◽  
De Novo Synthesis ◽  
Isotopomer Distribution ◽  
Long Chain ◽  
Mass Isotopomer

To determine the contributions of preexisting fatty acid, de novo synthesis, and chain elongation in long-chain fatty acid (LCFA) synthesis, the synthesis of LCFAs, palmitate (16:0), stearate (18:0), arachidate (20:0), behenate (22:0), and lignocerate (24:0), in the epidermis, liver, and spinal cord was determined using deuterated water and mass isotopomer distribution analysis in hairless mice and Sprague-Dawley rats. Animals were given 4% deuterated water for 5 days or 8 wk in their drinking water. Blood was withdrawn at the end of these times for the determination of deuterium enrichment, and the animals were killed to isolate the various tissues for lipid extraction for the determination of the mass isotopomer distributions. The mass isotopomer distributions in LCFA were incompatible with synthesis from a single pool of primer. The synthesis of palmitate, stearate, arachidate, behenate, and lignocerate followed the expected biochemical pathways for the synthesis of LCFAs. On average, three deuterium atoms were incorporated for every addition of an acetyl unit. The isotopomer distribution resulting from chain elongation and de novo synthesis can be described by the linear combination of two binomial distributions. The proportions of preexisting, chain elongation, and de novo-synthesized fatty acids as a percentage of the total fatty acids were determined using multiple linear regression analysis. Fractional synthesis was found to vary, depending on the tissue type and the fatty acid, from 47 to 87%. A substantial fraction (24-40%) of the newly synthesized molecules was derived from chain elongation of unlabeled (recycled) palmitate.

The composition and metabolism of fatty acids in Ips paraconfusus Lanier (Coleoptera: Scolytidae)

1972 ◽  
Vol 50 (10) ◽  
pp. 1263-1267 ◽  
Author(s):  
K. R. Penner ◽  
J. S. Barlow
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Sexual Dimorphism ◽  
Acid Composition ◽  
De Novo ◽  
Monounsaturated Fatty Acids ◽  
Ips Paraconfusus ◽  
Chain Elongation ◽  
De Novo Synthesis

The fatty acid composition of newly emerged Ips paraconfusus Lanier shows no sexual dimorphism and is approximately as follows: C14:0, 0.5%; C16:0, 23.0%; C16:1, 6%; C18:0, 3%; C18:1, 55%; C18:2, 9%; C18:3, 2%. Both sexes, but particularly the female, use up fatty acids, particularly the monounsaturated acids, during reproduction. Isotope from 1-14C-acetate injected into newly emerged females appeared in all saturated and monounsaturated fatty acids within 30 min. There was evidence of de novo synthesis of C14:0 and C16:0, chain elongation of C16:0 to C18:0, and desaturation of C16:0 and C18:0 to yield C16:1 and C18:1 respectively.

TetR-family transcriptional repressor Thermus thermophilus FadR controls fatty acid degradation

Microbiology ◽  
2011 ◽  
Vol 157 (6) ◽  
pp. 1589-1601 ◽  
Author(s):  
Yoshihiro Agari ◽  
Kazuko Agari ◽  
Keiko Sakamoto ◽  
Seiki Kuramitsu ◽  
Akeo Shinkai
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Target Genes ◽  
Thermus Thermophilus ◽  
Acyl Chain ◽  
Metabolic Energy ◽  
Straight Chain ◽  
Fatty Acid Degradation ◽  
Acid Degradation

In the extremely thermophilic bacterium Thermus thermophilus HB8, one of the four TetR-family transcriptional regulators, which we named T. thermophilus FadR, negatively regulated the expression of several genes, including those involved in fatty acid degradation, both in vivo and in vitro. T. thermophilus FadR repressed the expression of the target genes by binding pseudopalindromic sequences covering the predicted −10 hexamers of their promoters, and medium-to-long straight-chain (C10–18) fatty acyl-CoA molecules were effective for transcriptional derepression. An X-ray crystal structure analysis revealed that T. thermophilus FadR bound one lauroyl (C12)-CoA molecule per FadR monomer, with its acyl chain moiety in the centre of the FadR molecule, enclosed within a tunnel-like substrate-binding pocket surrounded by hydrophobic residues, and the CoA moiety interacting with basic residues on the protein surface. The growth of T. thermophilus HB8, with palmitic acid as the sole carbon source, increased the expression of FadR-regulated genes. These results indicate that in T. thermophilus HB8, medium-to-long straight-chain fatty acids can be used for metabolic energy under the control of FadR, although the major fatty acids found in this strain are iso- and anteiso-branched-chain (C15 and 17) fatty acids.

scholarly journals The synthesis of medium-chain fatty acids by lactating-rabbit mammary gland studied in vitro (Short Communication)

1973 ◽  
Vol 132 (1) ◽  
pp. 121-123 ◽  
Author(s):  
Christopher R. Strong ◽  
Eric M. Carey ◽  
Raymond Dils
Keyword(s):  
Fatty Acids ◽  
Molecular Weight ◽  
Mammary Gland ◽  
Fatty Acid ◽  
Short Communication ◽  
Acyl Chain ◽  
Fatty Acid Synthetase ◽  
Supernatant Fraction ◽  
Weight Factor

The proportion of C8:0 and C10:0 fatty acids synthesized by the microsomal plus particle-free supernatant fraction from lactating rabbit mammary gland is enhanced at high protein concentrations. This fraction appears to contain a soluble high-molecular-weight factor that modifies the specificity of the fatty acid synthetase complex for termination of the growing acyl chain.

scholarly journals The elongation of exogenous fatty acids and the control of phospholipid acyl chain length in Micrococcus cryophilus

1980 ◽  
Vol 188 (3) ◽  
pp. 585-592 ◽  
Author(s):  
S P Sandercock ◽  
N J Russell
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Chain Length ◽  
De Novo ◽  
Acyl Chain ◽  
Psychrophilic Bacterium ◽  
Fatty Acid Elongation ◽  
Acyl Chain Length ◽  
Acyl Chains ◽  
Phospholipid Acyl Chain

The synthesis of fatty acids de novo from acetate and the elongation of exogenous satuated fatty acids (C12-C18) by the psychrophilic bacterium Micrococcus cryophilus (A.T.C.C. 15174) grown at 1 or 20 degrees C was investigated. M. cryophilus normally contains only C16 and C18 acyl chains in its phospholipids, and the C18/C16 ratio is altered by changes in growth temperature. The bacterium was shown to regulate strictly its phospholipid acyl chain length and to be capable of directly elongating myristate and palmitate, and possibly laurate, to a mixture of C16 and C18 acyl chains. Retroconversion of stearate into palmitate also occurred. Fatty acid elongation could be distinguished from fatty acid synthesis de novo by the greater sensitivity of fatty acid elongation to inhibition by NaAsO2 under conditions when the supply of ATP and reduced nicotinamide nucleotides was not limiting. It is suggested that phospholipid acyl chain length may be controlled by a membrane-bound elongase enzyme, which interconverts C16 and C18 fatty acids via a C14 intermediate; the activity of the enzyme could be regulated by membrane lipid fluidity.

scholarly journals The Transcriptional Repressor FarR Is Not Involved in Meningococcal Fatty Acid Resistance Mediated by the FarAB Efflux Pump and Dependent on Lipopolysaccharide Structure

2010 ◽  
Vol 76 (10) ◽  
pp. 3160-3169 ◽  
Author(s):  
Stephanie Schielke ◽  
Corinna Schmitt ◽  
Carolin Spatz ◽  
Matthias Frosch ◽  
Alexandra Schubert-Unkmeir ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Lipid A ◽  
Efflux Pump ◽  
Acyl Chain ◽  
Acid Resistance ◽  
Transcriptional Regulator ◽  
Permeability Barrier ◽  
Membrane Anchor ◽  
Pump System

ABSTRACT Free fatty acids are important antimicrobial substances regulating the homeostasis of colonizing bacteria on epithelial surfaces. Here, we show that meningococci express a functional farAB efflux pump, which is indispensable for fatty acid resistance. However, other than in Neisseria gonorrhoeae, the transcriptional regulator FarR is not involved in regulation of this operon in Neisseria meningitidis. We tested the susceptibility of 23 meningococcal isolates against saturated and unsaturated long-chain fatty acids, proving that meningococci are generally highly resistant, with the exception of serogroup Y strains belonging to sequence type 23. Using genetically determined lipopolysaccharide (LPS)-truncated mutant strains, we show that addition of the LPS core oligosaccharide and hexa-acylation of its membrane anchor lipid A are imperative for fatty acid resistance of meningococci. The sensitivity of the serogroup Y strains is due to naturally occurring mutations within the lpxL1 gene, which is responsible for addition of the sixth acyl chain on the LPS membrane anchor lipid A. Therefore, fatty acid resistance in meningococci is provided by both the active efflux pump FarAB and by the natural permeability barrier of the Gram-negative outer membrane. The transcriptional regulator FarR is not implicated in fatty acid resistance in meningococci, possibly giving rise to a constitutively active FarAB efflux pump system and thus revealing diverse mechanisms of niche adaptation in the two closely related Neisseria species.

scholarly journals Fatty acid elongation by a particulate fraction from germinating pea

1980 ◽  
Vol 191 (3) ◽  
pp. 791-797 ◽  
Author(s):  
B R Jordan ◽  
J L Harwood
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Fatty Acid Synthesis ◽  
High Speed ◽  
Saturated Fatty Acids ◽  
Acyl Chain ◽  
Fatty Acid Synthetase ◽  
Acid Synthesis ◽  
Particulate Fraction

The synthesis of fatty acids from [14C]malonyl-CoA was studied with a high-speed particulate fraction from germinating pea (Pisum sativum). The variety used (Feltham First) produced mainly saturated fatty acids with palmitate (30–40%) and stearate (40–60%) predominating. Several palmitate-containing lipids stimulated overall synthesis and, in addition, increased the percentage of label in stearate. The production of stearate was severely inhibited by preincubation of the microsomal fraction with snake venom phospholipase A2 or by incubation with Rhizopus arrhizus lipase. Addition of a series of di-saturated phosphatidylcholines, with different acyl constituents, resulted in stimulation of overall fatty acid synthesis as well as an increase in the radiolabelling of the fatty acid two carbon atoms longer than the acyl chain added. This chain lengthening of fatty acids donated from phosphatidylcholine was due to the action of both fatty acid synthetase and palmitate elongase. The latter would utilize dipalmitoyl phosphatidylcholine and was sensitive to arsenite whereas fatty acid synthetase would use dilauroyl phosphatidylcholine and was sensitive to cerulenin. The results are discussed in relation to previous data obtained in vivo on plant fatty acid synthesis and current suggestions for the role of phosphatidylcholine in this process.

Fatty Acids: Evolution in Relation to Neurobiology

1993 ◽  
Vol 71 (9) ◽  
pp. 683-683 ◽  
Author(s):  
M. T. Clandinin
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Acid Content ◽  
Essential Fatty Acids ◽  
Fatty Acid Content ◽  
Chain Elongation ◽  
Brain Membrane ◽  
The Impact ◽  
Long Chain

Metabolism of long-chain polyunsaturated fatty acids derived from 18:2ω−6 and 18:3ω−3 by chain elongation – desaturation is essential for synthesis of complex structural lipids, leukotrienes, thromboxanes, and prostaglandins. These essential fatty acids are required for normal function in developing tissues and appropriate maturation of a wide variety of physiological processes. During development, fetal accretion of long-chain metabolites of ω−6 and ω−3 fatty acids may result from maternal or placental synthesis and transfer or, alternatively, from the metabolism of 18:2ω−6 and 18:3ω−3 to longer chain homologues by the fetus. After birth the infant must synthesize or be fed the very long chain polyunsaturated fatty acids of C20 and C22 type derived from 18:2ω−6 and 18:3ω−3.Metabolism of ω−6 and ω−3 fatty acids utilizes the same enzyme system and is competitive. When levels of dietary ω−3 and ω−6 C18 fatty acids are altered, the levels of metabolites of these precursor fatty acids change in specific brain membranes, influencing membrane lipid dependent functions. For example, a diet unbalanced in very long chain ω−3 and ω−6 fatty acids may increase brain membrane ω−3 fatty acid content when 20:5ω−3 is fed, while decreasing membrane fatty acid content of the ω−6 series of competing fatty acids. As 20:4ω−6 is quantitatively and qualitatively important to brain phospholipid, significant reduction in brain levels of 20:4ω−6 may be less than optimal. The impact of these compositional changes on brain function is not yet clear.The authors in this symposium address how this general area of essential fatty acid metabolism is relevant to the evolution of man, growth and development of fish, function of the retina and neural tissue, cognitive development of infants, and infant nutrition.

Factors Controlling Medium-Chain Fatty Acid Synthesis in Plastids from Maturing Cuphea Embryos

1993 ◽  
Vol 48 (7-8) ◽  
pp. 616-622 ◽  
Author(s):  
Jochen Fuhrmann ◽  
Klaus-Peter Heise
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Fatty Acid Synthesis ◽  
Lauric Acid ◽  
Capric Acid ◽  
Acid Synthesis ◽  
Pyridine Nucleotide ◽  
Chain Elongation ◽  
Medium Chain ◽  
Chain Fatty Acids

Abstract The colorless embryos of Cuphea wrightii A. Gray accumulate capric (about 30%) and lauric acid (about 50%) in their storage lipids. Fractionation studies show that the capacities for the synthesis of these medium-chain fatty acids (MCFA) from [1-14C]acetate were strictly bound to intact plastids. These, in turn, obligately required the addition of ATP. ATP could partially be substituted by ADP. Reduction of the pyridine nucleotide pool, required for opti­mum MCFA formation within the plastids, was driven by glucose 6-phosphate. Under these conditions the plastids were capable of synthesizing MCFA like the intact tissue. The presence of CoA in the incubation medium induced acyl-CoA formation. The observed accumulation of unesterified capric and lauric acid in the absence of CoA suggests that acyl-ACP thioesterase activity is involved in the chain termination. Treatment with cerulenin led to an unexpectedly small reduction of total fatty acid synthesis while the chain elongation of capric acid was clearly inhibited. A similar accumulation of capric acid at the expense of longer chain fatty acids has been observed after replacing ATP by ADP. These findings implicate that even the condensing enzymes are involved in the control of chain ter­mination.

scholarly journals Molecular cloning and characterisation of an acyl carrier protein thioesterase gene (CocoFatB1) expressed in the endosperm of coconut (Cocos nucifera) and its heterologous expression in Nicotiana tabacum to engineer the accumulation of different fatty acids

2014 ◽  
Vol 41 (1) ◽  
pp. 80 ◽  
Author(s):  
Yijun Yuan ◽  
Yinhua Chen ◽  
Shan Yan ◽  
Yuanxue Liang ◽  
Yusheng Zheng ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Amino Acid ◽  
Nicotiana Tabacum ◽  
Acyl Carrier Protein ◽  
Cocos Nucifera ◽  
Chain Elongation ◽  
Carrier Protein ◽  
Medium Chain ◽  
Tobacco Seeds

Coconut (Cocos nucifera L.) contains large amounts of medium chain fatty acids, which mostly recognise acyl-acyl carrier protein (ACP) thioesterases that hydrolyse acyl-ACP into free fatty acids to terminate acyl chain elongation during fatty acid biosynthesis. A full-length cDNA of an acyl-ACP thioesterase, designated CocoFatB1, was isolated from cDNA libraries prepared from coconut endosperm during fruit development. The gene contained an open reading frame of 1254 bp, encoding a 417-amino acid protein. The amino acid sequence of the CocoFatB1 protein showed 100% and 95% sequence similarity to CnFatB1 and oil palm (Elaeis guineensis Jacq.) acyl-ACP thioesterases, respectively. Real-time fluorescent quantitative PCR analysis indicated that the CocoFatB1 transcript was most abundant in the endosperm from 8-month-old coconuts; the leaves and endosperm from 15-month-old coconuts had ~80% and ~10% of this level. The CocoFatB1 coding region was overexpressed in tobacco (Nicotiana tabacum L.) under the control of the seed-specific napin promoter following Agrobacterium tumefaciens-mediated transformation. CocoFatB1 transcript expression varied 20-fold between different transgenic plants, with 21 plants exhibiting detectable levels of CocoFatB1 expression. Analysis of the fatty acid composition of transgenic tobacco seeds showed that the levels of myristic acid (14 : 0), palmitic acid (16 : 0) and stearic acid (18 : 0) were increased by 25%, 34% and 17%, respectively, compared with untransformed plants. These results indicated that CocoFatB1 acts specifically on 14 : 0-ACP, 16 : 0-ACP and 18 : 0-ACP, and can increase medium chain saturated fatty acids. The gene may valuable for engineering fatty acid metabolism in crop improvement programmes.

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