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Sample records for ethyl fatty acid

  1. 40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

  2. 40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

  3. 40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates (salts). 721.3152 Section 721... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

  4. Impact of Association Colloids on Lipid Oxidation in Triacylglycerols and Fatty Acid Ethyl Esters.

    PubMed

    Homma, Rika; Suzuki, Karin; Cui, Leqi; McClements, David Julian; Decker, Eric A

    2015-11-25

    The impact of association colloids on lipid oxidation in triacylglycerols and fatty acid ethyl esters was investigated. Association colloids did not affect lipid oxidation of high oleic safflower and high linoleic safflower triacylglycerols, but were prooxidative in fish triacylglycerols. Association colloids retarded aldehyde formation in stripped ethyl oleate, linoleate, and fish oil ethyl esters. Interfacial tension revealed that lipid hydroperoxides were surface active in the presence of the surfactants found in association colloids. The lipid hydroperoxides from ethyl esters were less surface active than triacylglycerol hydroperoxides. Stripping decreased iron and copper concentrations in all oils, but more so in fatty acid ethyl esters. The combination of lower hydroperoxide surface activity and low metal concentrations could explain why association colloids inhibited lipid oxidation in fatty acid ethyl esters. This research suggests that association colloids could be used as an antioxidant technology in fatty acid ethyl esters.

  5. Determination of ethyl glucuronide and fatty acid ethyl esters in hair samples.

    PubMed

    Oppolzer, David; Barroso, Mário; Passarinha, Luís; Gallardo, Eugenia

    2017-04-01

    Hair testing for alcohol biomarkers is an important tool for monitoring alcohol consumption. We propose two methods for assessing alcohol exposure through combined analysis of ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) species (ethyl myristate, palmitate, stearate and oleate) in hair (30 mg). EtG was analysed by liquid chromatography-tandem mass spectrometry, while FAEEs were analysed by gas chromatography-tandem mass spectrometry using electron impact ionization. Both methods were validated according to internationally accepted guidelines. Linearity was proven between 3 and 500 pg/mg for EtG and 30-5000 pg/mg for FAEEs, and the limits of quantification were 3 pg/mg for EtG and 30 pg/mg for each of the four FAEEs. Precision and accuracy were considered adequate, processed EtG samples were found to be stable for up to 96 h left in the injector and processed FAEEs samples for up to 24 h. Matrix effects were not significant. Both methods were applied to the analysis of 15 authentic samples, using the cut-off values proposed by the Society of Hair Testing for interpretation. The results agreed well with the self-reported alcohol consumption in most cases, and demonstrated the suitability of the methods to be applied in routine analysis of alcohol biomarkers, allowing monitoring consumption using low sample amounts.

  6. Fatty Acid Ethyl Esters Are Less Toxic Than Their Parent Fatty Acids Generated during Acute Pancreatitis

    PubMed Central

    Patel, Krutika; Durgampudi, Chandra; Noel, Pawan; Trivedi, Ram N.; de Oliveira, Cristiane; Singh, Vijay P.

    2017-01-01

    Although ethanol causes acute pancreatitis (AP) and lipolytic fatty acid (FA) generation worsens AP, the contribution of ethanol metabolites of FAs, ie, FA ethyl esters (FAEEs), to AP outcomes is unclear. Previously, pancreata of dying alcoholics and pancreatic necrosis in severe AP, respectively, showed high FAEEs and FAs, with oleic acid (OA) and its ethyl esters being the most abundant. We thus compared the toxicities of FAEEs and their parent FAs in severe AP. Pancreatic acini and peripheral blood mononuclear cells were exposed to FAs or FAEEs in vitro. The triglyceride of OA (i.e., glyceryl tri-oleate) or OAEE was injected into the pancreatic ducts of rats, and local and systemic severities were studied. Unsaturated FAs at equimolar concentrations to FAEEs induced a larger increase in cytosolic calcium, mitochondrial depolarization, and necro-apoptotic cell death. Glyceryl tri-oleate but not OAEE resulted in 70% mortality with increased serum OA, a severe inflammatory response, worse pancreatic necrosis, and multisystem organ failure. Our data show that FAs are more likely to worsen AP than FAEEs. Our observations correlate well with the high pancreatic FAEE concentrations in alcoholics without pancreatitis and high FA concentrations in pancreatic necrosis. Thus, conversion of FAs to FAEE may ameliorate AP in alcoholics. PMID:26878214

  7. 40 CFR 721.3152 - Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethanaminium, N-ethyl-2-hydroxy-N,N... Ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates... ethanaminium, N-ethyl-2-hydroxy-N,N-bis(2-hydroxyethyl)-, diester with C12-18 fatty acids, ethyl sulfates...

  8. Testing for ethanol markers in hair: discrepancies after simultaneous quantification of ethyl glucuronide and fatty acid ethyl esters.

    PubMed

    Kintz, P; Nicholson, D

    2014-10-01

    The hair of 97 cases were analysed for ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEE, including ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate) according to the Society of Hair Testing guidelines to examine the role of both tests in documenting chronic excessive alcohol drinking, particularly when the results are in contradiction. 27 (27.8%) results were EtG negative and FAEE positive, when applying the SoHT cut-offs, probably due to the use of alcohol-containing hair products. Four cases (4.1%) were EtG positive and FAEE negative that were attributed to the use of herbal lotions containing EtG.

  9. Examination of sex differences in fatty acid ethyl ester and ethyl glucuronide hair analysis.

    PubMed

    Gareri, Joey; Rao, Chitra; Koren, Gideon

    2014-06-01

    Clinical studies examining performance of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in identifying excessive alcohol consumption have been primarily conducted in male populations. An impact of hair cosmetics in producing both false-negative EtG results and false-positive FAEE results has been demonstrated, suggesting a possible bias in female populations. This study evaluates FAEE-positive hair samples (>0.50 ng/mg) from n = 199 female and n = 73 male subjects for EtG. Higher FAEE/EtG concordance was observed amongst male over female subjects. Performance of multiple proposed EtG cut-off levels were assessed; amongst female samples, FAEE/EtG concordance was 36.2% (30 pg/mg), 36.7% (27 pg/mg), and 43.7% (20 pg/mg). Non-coloured hair demonstrated a two-fold increase in concordance (41.8 v. 20.8%) over coloured hair in the female cohort. FAEE levels did not differ between male and female subjects; however they were lower in coloured samples (p = 0.046). EtG was lower in female subjects (p = 0.019) and coloured samples (p = 0.026). A total of n = 111 female samples were discordant. Amongst discordant samples (EtG-negative), 26% had evidence of recent alcohol use including consultation histories (n = 20) and detectable cocaethylene (n = 9); 29% of discordant samples were coloured. False-negative risk with ethyl glucuronide analysis in females was mediated by cosmetic colouring. These findings suggest that combined analysis of FAEE and EtG is optimal when assessing a female population and an EtG cut-off of 20 pg/mg is warranted when using combined analysis. While concordant FAEE/EtG-positive findings constitute clear evidence, discordant FAEE/EtG findings should still be considered suggestive evidence of chronic excessive alcohol consumption.

  10. Fatty Acid Ethyl Esters in Meconium: Are They Biomarkers of Fetal Alcohol Exposure and Effect?

    PubMed Central

    Ostrea, Enrique M.; Hernandez, Joel D.; Bielawski, Dawn M.; Kan, Jack M.; Leonardo, Gregorio M.; Abela, Michelle Buda; Church, Michael W.; Hannigan, John H.; Janisse, James J.; Ager, Joel W.; Sokol, Robert J.

    2011-01-01

    Background Biomarkers of fetal exposure to alcohol are important to establish so that early detection and intervention can be made on these infants to prevent undesirable outcomes. The aim of this study was to analyze long-chain fatty acid ethyl esters (FAEEs) in meconium as potential biomarkers of fetal alcohol exposure and effect. Methods Fatty acid ethyl esters were analyzed in the meconium of 124 singleton infants by positive chemical ionization gas chromatography/mass spectrometry (GC/MS) and correlated to maternal ethanol use. Results A total of 124 mother/infant dyads were enrolled in the study: 31 were in the control group and 93 were in the alcohol-exposed group. The incidence (28% vs 9.7%, p=0.037) of ethyl linoleate detected in meconium was significantly higher in the alcohol-exposed groups than the control groups. Similarly, when the concentrations of ethyl linoleate in meconium were grouped (trichotomized), there was a significant linear by linear association between alcohol exposure and group concentrations of ethyl linoleate (p=0.013). Furthermore, only alcohol-exposed infants were found in the group with the highest ethyl linoleate concentration. The sensitivity of ethyl linoleate in detecting prenatal alcohol exposure was only 26.9%, and its specificity and positive predictive value were 96.8 and 96.2%, respectively. There was no significant correlation between the concentration of ethyl linoleate in meconium and absolute alcohol consumed (oz) per drinking day across pregnancy, although a trend toward a positive correlation is seen at lower amounts of alcohol consumed. Among the polyunsaturated, long-chain FAEEs, there was weak evidence that the incidence (21.5% vs 6.5%, p=0.057) and concentration (p=0.064) of ethyl arachidonate (AA) were significantly higher in the alcohol-exposed groups than the control groups. Ethyl linolenate and ethyl docosahexanoate (DHA) in meconium were found only in the alcohol group, although not at statistically

  11. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to...

  12. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  13. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  14. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

  15. Synthesis of medium chain length fatty acid ethyl esters in engineered Escherichia coli using endogenously produced medium chain fatty acids.

    PubMed

    Fan, Liping; Liu, Junfeng; Nie, Kaili; Liu, Luo; Wang, Fang; Tan, Tianwei; Deng, Li

    2013-07-10

    Microbial biosynthesis of fatty acid-derived biofuels from renewable carbon sources has attracted significant attention in recent years. Free fatty acids (FFAs) can be used as precursors for the production of micro-diesel. The expression of codon optimized two plants (Umbellularia californica and Cinnamomum camphora) medium-chain acyl-acyl carrier protein (ACP) thioesterase genes (ucFatB and ccFatB) in Escherichia coli resulted in a very high level of extractable medium-chain-specific hydrolytic activity and caused large accumulation of medium-chain free fatty acids. By heterologous co-expression of acyl-coenzyme A:diacylglycerol acyltransferase from Acinetobacter baylyi ADP1, specific plant thioesterases in E. coli, with supplementation of exogenous ethanol, resulted in drastic changes in fatty acid ethyl esters (FAEEs) composition ranging from 12:0 to 18:1. Through an optimized microbial shake-flask fermentation of two modified E. coli strains, yielded FFAs and FAEEs in the concentration of approximately 500 mg L(-1)/250 mg L(-1) and 2.01 mg g(-1)/1.99 mg g(-1), respectively. The optimal ethanol level for FAEEs yield in the two recombinant strains was reached at the 3% ethanol concentration, which was about 5.4-fold and 1.93-fold higher than that of 1% ethanol concentration. Copyright © 2013 Elsevier Inc. All rights reserved.

  16. Headspace solid-phase microextraction of higher fatty acid ethyl esters in white rum aroma.

    PubMed

    Pino, J; Martí, M P; Mestres, M; Pérez, J; Busto, O; Guasch, J

    2002-04-19

    Fatty acid ethyl esters are the main components of rum aroma and play an important sensorial impact in these distilled alcoholic beverages. Herein, a method for analysing these volatile compounds is described. It involves a separation and concentration step using headspace solid-phase microextraction and determination by capillary gas chromatography using flame ionisation detection. The influence of different parameters related to the isolation and concentration step, such as ethanol concentration, ionic strength, sample volume, time and temperature of extraction, was studied. The developed method enabled recoveries >91% for the analyzed compounds with limits of detection between 0.007 and 0.027 mg/l, all of them lower than the range of concentrations found in rum samples. The method was successfully applied to the analysis of fatty acid ethyl esters in different commercial white rums.

  17. Differentiating prescription omega-3-acid ethyl esters (P-OM3) from dietary-supplement omega-3 fatty acids.

    PubMed

    Brunton, Stephen; Collins, Nancy

    2007-05-01

    A reliable means of treating hyper-triglyceridemia is the use of large doses of the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Modest levels of EPA and DHA may be obtained from food, particularly fatty fish. This article is intended to review clinically relevant differences between dietary-supplement omega-3 fatty acids and prescription omega-3-acid ethyl esters (P-OM3). PubMed and the Food and Drug Administration (FDA) Website were searched for articles published between 1995 and 2007 that contained the terms fish oil, fatty acids, n-3 fatty acids, omega fatty acids, docosahexaenoic acid, or eicosapentaenoic acid. Articles discussing sources, recommended intake, and differences among various formulations of omega-3 fatty acids were selected for review. A limitation to this review is the lack of head-to-head clinical trials using P-OM3 and dietary-supplement omega-3 fatty acids. Many types of nonprescription dietary supplements of omega-3 fatty acids are available; however, the efficacy, quality, and safety of these products are open to question because they are not regulated by the same standards as pharmaceutical agents. P-OM3 is the only omega-3 fatty acid product (Omacor capsules) approved by the US FDA available in the United States as an adjunct to diet to reduce very high (> or = 500 mg/dL) triglyceride levels in adult patients. P-OM3 can be used with confidence by practitioners who want to provide therapeutic doses of omega-3 fatty acids in a preparation that has been documented to be both safe and effective.

  18. Metabolic pathway engineering for fatty acid ethyl ester production in Saccharomyces cerevisiae using stable chromosomal integration.

    PubMed

    de Jong, Bouke Wim; Shi, Shuobo; Valle-Rodríguez, Juan Octavio; Siewers, Verena; Nielsen, Jens

    2015-03-01

    Fatty acid ethyl esters are fatty acid derived molecules similar to first generation biodiesel (fatty acid methyl esters; FAMEs) which can be produced in a microbial cell factory. Saccharomyces cerevisiae is a suitable candidate for microbial large scale and long term cultivations, which is the typical industrial production setting for biofuels. It is crucial to conserve the metabolic design of the cell factory during industrial cultivation conditions that require extensive propagation. Genetic modifications therefore have to be introduced in a stable manner. Here, several metabolic engineering strategies for improved production of fatty acid ethyl esters in S. cerevisiae were combined and the genes were stably expressed from the organisms' chromosomes. A wax ester synthase (ws2) was expressed in different yeast strains with an engineered acetyl-CoA and fatty acid metabolism. Thus, we compared expression of ws2 with and without overexpression of alcohol dehydrogenase (ADH2), acetaldehyde dehydrogenase (ALD6) and acetyl-CoA synthetase (acs SE (L641P) ) and further evaluated additional overexpression of a mutant version of acetyl-CoA decarboxylase (ACC1 (S1157A,S659A) ) and the acyl-CoA binding protein (ACB1). The combined engineering efforts of the implementation of ws2, ADH2, ALD6 and acs SE (L641P) , ACC1 (S1157A,S659A) and ACB1 in a S. cerevisiae strain lacking storage lipid formation (are1Δ, are2Δ, dga1Δ and lro1Δ) and β-oxidation (pox1Δ) resulted in a 4.1-fold improvement compared with sole expression of ws2 in S. cerevisiae.

  19. Enzymatic synthesis of fatty acid ethyl esters by utilizing camellia oil soapstocks and diethyl carbonate.

    PubMed

    Wang, Yingying; Cao, Xuejun

    2011-11-01

    This study was reported on a novel process for fatty acid ethyl esters preparation by transesterification and esterification from renewable low-cost feedstock camellia oil soapstocks and friendly acyl acceptor diethyl carbonate. The main components of product were 83.9% ethyl oleate, 8.9% ethyl palmitate, 4.7% ethyl linoleate and 2.1% ethyl stearate, which could be used as eco-friendly renewable resources or additives of industrial solvent and fossil fuel. The effects of molar ratio of diethyl carbonate to soapstocks oil, lipases, organic solvent, reaction temperature and time were investigated, and process conditions were optimized. The yield was up to 98.4% in solvent-free system with molar ratio of diethyl carbonate to soapstocks oil 3:1 and 5% Novozym 435 (based on the weight of soapstocks oil) at 50 °C and 180 rpm for 24 h. Moreover, there was no obvious loss in the yield after lipases were reused for 10 batches without treatment under optimized conditions. Copyright © 2011 Elsevier Ltd. All rights reserved.

  20. Physiological and transcriptional characterization of Saccharomyces cerevisiae engineered for production of fatty acid ethyl esters.

    PubMed

    de Jong, Bouke Wim; Siewers, Verena; Nielsen, Jens

    2016-02-01

    Saccharomyces cerevisiae has previously been engineered to become a cell factory for the production of fatty acid ethyl esters (FAEEs), molecules suitable for crude diesel replacement. To find new metabolic engineering targets for the improvement of FAEE cell factories, three different FAEE-producing strains of S. cerevisiae, constructed previously, were compared and characterized by quantification of key fluxes and genome-wide transcription analysis. From both the physiological and the transcriptional data, it was indicated that strain CB2I20, with high expression of a heterologous wax ester synthase gene (ws2) and strain BdJ15, containing disruptions of genes DGA1, LRO1, ARE1, ARE2 and POX1, which prevent the conversion of acyl-CoA to sterol esters, triacylglycerides and the degradation to acetyl-CoA, triggered oxidative stress that consequently influenced cellular growth. In the latter strain, stress was possibly triggered by disabling the buffering capacity of lipid droplets in encapsulating toxic fatty acids such as oleic acid. Additionally, it was indicated that there was an increased demand for NADPH required for the reduction steps in fatty acid biosynthesis. In conclusion, our analysis clearly shows that engineering of fatty acid biosynthesis results in transcriptional reprogramming and has a significant effect on overall cellular metabolism.

  1. Fatty acid ethyl ester synthesis in the preparation of scotch whiskey.

    PubMed

    Goss, K A; Alharethi, R; Laposata, M

    1999-04-01

    Fatty acid ethyl esters (FAEE), nonoxidative ethanol metabolites present in human organs commonly damaged by ethanol abuse, have been implicated as mediators of organ damage. FAEE are additives in various foods and beverages to provide flavor or fragrance, and therefore are common dietary lipid constituents. We hypothesized that FAEE could be generated during alcoholic beverage production because fatty acids are present within microorganisms and ethanol is generated during the fermentation process. In this report, we demonstrate that FAEE are present in commercially available scotch beverages, and that in the preparation of scotch, FAEE can be produced during the fermentation reaction as a result of FAEE synthase activity in the yeast. Following ingestion of scotch, preformed FAEE are delivered to GI tract. The consequences of ingestion of FAEE in scotch, if any, remain to be determined.

  2. Stability studies on methyl and ethyl fatty acid esters of sunflower seed oil

    SciTech Connect

    Du Plessis, L.M.; De Villiers, J.B.M.; Van der Walt, W.H.

    1985-04-01

    Fatty acid esters, high in linoleic acid, were prepared and stored for long-term engine tests. Storage tests were undertaken to obtain data on optimal storage requirements and general stability characteristics. Samples were kept at three temperature levels (20 C, 30C and fluctuating around 50 C) for a 90-day period and were removed at regular intervals for chemical and physical analysis. The influence of air, temperature, light, TBHQ and contact with mild steel was evaluated by comparing the free fatty acid, peroxide, anisidine, ultraviolet absorption, viscosity and inducation periods. A statistical model was used to evaluate the data and to reduce the data points to comparable curves. Storage of esters in contact with air, especially at a temperature above 30 C, resulted in significant increases in peroxide, ultraviolet absorption, free fatty acid, viscosity and anisidine values. Exclusion of air retarded oxidation at all temperature levels. A direct relationship between viscosity increases and oxidation parameters was evident. Exposure to light caused a small increase in the oxidation parameters of esters stored at the highest temperature level. Addition of TBHQ prevented oxidation of samples stored under moderate conditions. Under unfavorable storage conditions the anti-oxidant was no longer effective. Mild steel had very little effect on the oxidation parameters. The anisidine values of samples stored at the highest temperature level were slightly increased. Methyl esters performed slightly better than ethyl esters during the storage test. The recommended guidelines for storage of fatty acid ester fuels are: (1) airtight containers should be used, (2) the storage temperature should be less than 30 C, (3) mild steel (rust free) containers may be used, and (4) TBHQ has a beneficial effect on oxidation stability. 13 references.

  3. Enhancing fatty acid ethyl ester production in Saccharomyces cerevisiae through metabolic engineering and medium optimization.

    PubMed

    Thompson, R Adam; Trinh, Cong T

    2014-11-01

    Biodiesels in the form of fatty acyl ethyl esters (FAEEs) are a promising next generation biofuel due to their chemical properties and compatibility with existing infrastructure. It has recently been shown that expression of a bacterial acyl-transferase in the established industrial workhorse Saccharomyces cerevisiae can lead to production of FAEEs by condensation of fatty acyl-CoAs and ethanol. In contrast to recent strategies to produce FAEEs in S. cerevisiae through manipulation of de novo fatty acid biosynthesis or a series of arduous genetic manipulations, we introduced a novel genetic background, which is comparable in titer to previous reports with a fraction of the genetic disruption by aiming at increasing the fatty acyl-CoA pools. In addition, we combined metabolic engineering with modification of culture conditions to produce a maximum titer of over 25 mg/L FAEEs, a 40% improvement over previous reports and a 17-fold improvement over our initial characterizations. Biotechnol. Bioeng. 2014;111: 2200-2208. © 2014 Wiley Periodicals, Inc. © 2014 Wiley Periodicals, Inc.

  4. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the following prescribed conditions: (a)...

  5. Clinical sensitivity and specificity of meconium fatty acid ethyl ester, ethyl glucuronide, and ethyl sulfate for detecting maternal drinking during pregnancy.

    PubMed

    Himes, Sarah K; Dukes, Kimberly A; Tripp, Tara; Petersen, Julie M; Raffo, Cheri; Burd, Larry; Odendaal, Hein; Elliott, Amy J; Hereld, Dale; Signore, Caroline; Willinger, Marian; Huestis, Marilyn A

    2015-03-01

    We investigated agreement between self-reported prenatal alcohol exposure (PAE) and objective meconium alcohol markers to determine the optimal meconium marker and threshold for identifying PAE. Meconium fatty acid ethyl esters (FAEE), ethyl glucuronide (EtG), and ethyl sulfate (EtS) were quantified by LC-MS/MS in 0.1 g meconium from infants of Safe Passage Study participants. Detailed PAE information was collected from women with a validated timeline follow-back interview. Because meconium formation begins during weeks 12-20, maternal self-reported drinking at or beyond 19 weeks was our exposure variable. Of 107 women, 33 reported no alcohol consumption in pregnancy, 16 stopped drinking by week 19, and 58 drank beyond 19 weeks (including 45 third-trimester drinkers). There was moderate to substantial agreement between self-reported PAE at ≥19 weeks and meconium EtG ≥30 ng/g (κ = 0.57, 95% CI 0.41-0.73). This biomarker and associated cutoff was superior to a 7 FAEE sum ≥2 nmol/g and all other individual and combination marker cutoffs. With meconium EtG ≥30 ng/g as the gold standard condition and maternal self-report at ≥19 weeks' gestation as the test condition, 82% clinical sensitivity (95% CI 71.6-92.0) and 75% specificity (95% CI 63.2-86.8) were observed. A significant dose-concentration relationship between self-reported drinks per drinking day and meconium EtG ≥30 ng/g also was observed (all P < 0.01). Maternal alcohol consumption at ≥19 weeks was better represented by meconium EtG ≥30 ng/g than currently used FAEE cutoffs. © 2014 American Association for Clinical Chemistry.

  6. Clinical Sensitivity and Specificity of Meconium Fatty Acid Ethyl Esters, Ethyl Glucuronide, and Ethyl Sulfate for Detecting Maternal Drinking During Pregnancy

    PubMed Central

    Himes, Sarah K.; Dukes, Kimberly A.; Tripp, Tara; Petersen, Julie M.; Raffo, Cheri; Burd, Larry; Odendaal, Hein; Elliott, Amy J.; Hereld, Dale; Signore, Caroline; Willinger, Marian; Huestis, Marilyn A.

    2015-01-01

    Background We investigated agreement between self-reported prenatal alcohol exposure (PAE) and objective meconium alcohol markers to determine the optimal meconium marker and threshold for identifying PAE. Methods Meconium fatty acid ethyl esters (FAEE), ethyl glucuronide (EtG), and ethyl sulfate (EtS) were quantified by liquid chromatography-tandem mass spectrometry in 0.1 g meconium from infants of Safe Passage Study participants. Detailed PAE information was collected from women with a validated timeline follow-back interview. As meconium formation begins during weeks 12-20, maternal self-reported drinking at or beyond 19 weeks was our exposure variable. Results Of 107 women, 33 reported no alcohol consumption in pregnancy, 16 stopped drinking by week 19, and 58 drank beyond 19 weeks (including 45 3rd trimester drinkers). There was moderate-substantial agreement between self-reported PAE ≥19 weeks and meconium EtG ≥30 ng/g (kappa: 0.57, 95% CI 0.41-0.73). This biomarker and associated cutoff was superior to a 7 FAEE sum ≥2 nmol/g and all other individual and combination marker cutoffs. With meconium EtG ≥30 ng/g as the gold-standard condition and maternal self-report ≥19 weeks gestation as the test condition, 82% sensitivity (95% CI: 71.6-92.0) and 75% specificity (95% CI: 63.2-86.8) were observed. A significant dose-concentration relationship between self-reported drinks per drinking day and meconium EtG ≥30 ng/g also was observed (P<0.01). Conclusions We assessed meconium EtG, EtS, and FAEE concentrations in the same meconium sample and compared concentrations to detailed self-reported PAE data. Maternal alcohol consumption ≥19 weeks was better represented by meconium EtG ≥30 ng/g compared to current FAEE cutoffs. PMID:25595440

  7. Treatment with omega-3 fatty acid ethyl-ester alters fatty acid composition of lipoproteins in overweight or obese adults with insulin resistance.

    PubMed

    Augustine, Alicia H; Lowenstein, Lisa M; Harris, William S; Shearer, Gregory C; Block, Robert C

    2014-01-01

    The effects of dietary fatty acid supplementation on lipoprotein fatty acid composition have rarely been described. Sixty-one overweight and obese adults with dyslipidemia and insulin resistance were randomized to placebo, 2g/day extended-release nicotinic acid (ERN), 4g/day prescription omega-3 fatty acid ethyl ester (P-OM3), or combination therapy for 16 weeks. Lipoprotein fatty acid composition was analyzed by gas chromatography pre- and post-treatment. Treatment with P-OM3 or combination, but not ERN, increased proportions of eicosapentaenoic acid, docosahexaenoic acid, and docosapentaenoic acid, and reduced those for arachidonic acid in all lipoprotein fractions, with greatest impact in the high-density lipoprotein fraction. P-OM3-induced changes in eicosapentaenoic acid within low-density lipoproteins and very low-density lipoproteins were associated with beneficial effects on mean arterial pressure and pulse pressure. P-OM3 supplementation, with or without ERN, was associated with differentially altered lipoprotein fatty acid composition and improved blood pressure parameters. Copyright © 2013 Elsevier Ltd. All rights reserved.

  8. Combined use of fatty acid ethyl esters and ethyl glucuronide in hair for diagnosis of alcohol abuse: interpretation and advantages.

    PubMed

    Pragst, F; Rothe, M; Moench, B; Hastedt, M; Herre, S; Simmert, D

    2010-03-20

    In this study the combined use of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) for diagnoses of chronically excessive alcohol abuse is investigated at 174 hair samples from driving ability examination, workplace testing and child custody cases for family courts and evaluated with respect to the basics of interpretation. Using the cut-off values of 0.50 ng/mg for FAEE and 25 pg/mg for EtG, both markers were in agreement in 75% of the cases with 103 negative and 28 positive results and there were 30 cases with FAEE positive and EtG negative and 13 cases with FAEE negative and EtG positive. As the theoretical basis of interpretation, the pharmacokinetics of FAEE and EtG is reviewed for all steps between drinking of ethanol to incorporation in hair with particular attention to relationships between alcohol dose and concentrations in hair. It is shown that the concentrations of both markers are essentially determined by the area under the ethanol concentration in blood vs. time curve AUC(EtOH), despite large inter-individual variations. It is demonstrated by calculation of AUC(EtOH) on monthly basis for moderate, risky and heavy drinking that AUC(EtOH) increases very strongly in the range between 60 and 120 g ethanol per day. This specific feature which is caused by the zero-order elimination of ethanol is a favorable prerequisite for a high discrimination power of the hair testing for alcohol abuse. From the consideration of the different profiles of FAEE and EtG along the hair and in agreement with the literature survey, a standardized hair segment 0-3 cm is proposed with cut-off values of 0.5 ng/mg for FAEE and 30 pg/mg for EtG. This improves also the agreement between FAEE and EtG results in the cases of the present study. A scheme for combined interpretation of FAEE and EtG is proposed which uses the levels of abstinence and the double of the cut-off values as criteria in addition to the cut-off's. Considering the large variations in the relationship

  9. Photosynthetic CO2 Conversion to Fatty Acid Ethyl Esters (FAEEs) Using Engineered Cyanobacteria.

    PubMed

    Lee, Hyun Jeong; Choi, Jaeyeon; Lee, Sun-Mi; Um, Youngsoon; Sim, Sang Jun; Kim, Yunje; Woo, Han Min

    2017-02-15

    Metabolic engineering of cyanobacteria has received attention as a sustainable strategy to convert carbon dioxide to fatty acid-derived chemicals that are widely used in the food and chemical industries. Herein, Synechococcus elongatus PCC 7942, a model cyanobacterium, was engineered for the first time to produce fatty acid ethyl esters (FAEEs) from CO2. Due to the lack of an endogenous ethanol production pathway and wax ester synthase (AftA) activity in the wild-type cyanobacterium, we metabolically engineered S. elongatus PCC 7942 by expressing heterologous AftA and introducing the ethanol pathway, resulting in detectable peaks of FAEEs. To enhance FAEE production, a heterologous phosphoketolase pathway was introduced in the FAEE-producing strain to supply acetyl-CoA. Subsequent optimization of the cyanobacterial culture with a hexadecane overlay resulted in engineered S. elongatus PCC 7942 that produced photosynthetic FAEEs (10.0 ± 0.7 mg/L/OD730) from CO2. This paper is the first report of photosynthetic production of FAEEs from CO2 in cyanobacteria.

  10. In heavy drinkers, fatty acid ethyl esters remain elevated for up to 99 hours.

    PubMed

    Borucki, K; Dierkes, J; Wartberg, J; Westphal, S; Genz, A; Luley, C

    2007-03-01

    Both medical and forensic needs require reliable detection of earlier ethanol intake after the disappearance of ethanol from blood. The esters of ethanol with free fatty acids (FAEEs) are candidate markers of this kind. However, it is unknown whether FAEEs can serve as a marker for a single prior ethanol intake. In addition, the period for which FAEEs are elevated is unknown. Therefore, we measured FAEEs in heavy drinkers admitted to detoxification, and in healthy subjects after a drinking experiment. Blood from 30 heavy drinkers was obtained for up to 5 days during a detoxification period in a psychiatric hospital. In addition, 17 healthy subjects who participated in a drinking experiment and who were abstinent thereafter gave blood during a similar time period for analysis of FAEEs. Fatty acid ethyl esters were measured by gas chromatography-mass spectroscopy. Heavy drinkers had much higher ethanol and FAEEs concentrations than healthy subjects; however, in both groups, FAEEs decreased rapidly during the first day. Only in heavy drinkers, elevated concentrations of FAEEs were observed at days 2 to 4. Concentrations of FAEEs were not associated with serum triglycerides or patients' body mass index. It is concluded that kinetics of FAEEs are different in heavy drinkers compared with healthy subjects and that FAEEs are of limited value for the detection of prior single ethanol intake.

  11. Ethanol contamination leads to Fatty acid ethyl esters in hair samples.

    PubMed

    De Giovanni, Nadia; Donadio, Giuseppe; Chiarotti, Marcello

    2008-03-01

    The diagnosis of alcoholism is a topical subject of discussion; in fact, many studies have been published on the determination of biochemical markers useful to this target. Fatty acid ethyl esters (FAEE) are minor metabolites of ethanol, and their usefulness has been demonstrated by their detection in hair using a headspace solid-phase microextraction-gas chromatographic-mass spectrometric technique. Environmental contamination in the analysis of drugs of abuse is a well-known focus of discussion between scientists. In the same way, interference from the surroundings could be hypothesized in FAEE detection. To assess the influence of ethanol contamination, an in vitro experiment was performed, leaving hair in an atmosphere saturated with ethanol vapors for 15 days. The spontaneous production of FAEE was demonstrated by analyzing hair day by day. In fact, we observed a constant increase of ethyl myristate, palmitate, and stearate that reached very high concentrations at the end of the investigation. Although the experiment was managed in a stressed way and could not represent real life, its purpose was to focus the attention of researchers on the problem of hair contamination that can occur, for example, with ethanol-containing cosmetics. Therefore, care in interpretation must be taken into account, especially with such a volatile molecule.

  12. Elevated fatty acid ethyl esters in meconium of sheep fetuses exposed in utero to ethanol--a new animal model.

    PubMed

    Littner, Yoav; Cudd, Timothy A; O'Riordan, Mary A; Cwik, Andrew; Bearer, Cynthia F

    2008-02-01

    Specific fatty acid ethyl esters (FAEE) in meconium of newborns have been shown to correlate with maternal ethanol exposure. An animal model is needed to assess the validity of this biomarker. We hypothesized that the pregnant/fetal sheep is a feasible animal model for validating FAEE as a biomarker of prenatal ethanol exposure. Nine pregnant ewes were treated during the third trimester with different i.v. ethanol doses. The control group consisted of 14 pregnant ewes exposed to similar volumes of saline. On gestational d 133, the fetuses were delivered and meconium samples removed. FAEEs were quantified by gas chromatography-flame ionization detection. FAEEs were found in both control and ethanol exposed fetuses. Ethyl oleate, ethyl linoleate, and ethyl arachidonate levels were significantly higher in the ethanol-exposed sheep. Ethyl oleate was the FAEE that correlated most strongly with alcohol ingestion during pregnancy and had the greatest area under the curve (0.94). Using a cut-off value of 131 ng/g ethyl oleate dry weight, sensitivity was 89% and specificity was 100%. In conclusion, pregnant ewes are a feasible model for validating biomarkers of prenatal ethanol exposure. Ethyl oleate, ethyl linoleate, and ethyl arachidonate may be useful biomarkers of prenatal alcohol exposure.

  13. Fatty acid ethyl esters disrupt neonatal alveolar macrophage mitochondria and derange cellular functioning.

    PubMed

    Mohan, Sowmya S; Ping, Xiao Du; Harris, Frank L; Ronda, Necol J; Brown, Lou Ann S; Gauthier, Theresa W

    2015-03-01

    Chronic alcohol exposure alters the function of alveolar macrophages (AM), impairing immune defenses in both adult and neonatal lungs. Fatty acid ethyl esters (FAEEs) are biological markers of prenatal alcohol exposure in newborns. FAEEs contribute to alcohol-induced mitochondrial (MT) damage in multiple organs. We hypothesized that in utero ethanol exposure would increase FAEEs in the neonatal lung and that direct exposure of neonatal AM to FAEEs would contribute to MT injury and cellular dysfunction. FAEEs were measured in neonatal guinea pig lungs after ± in utero ethanol exposure via gas chromatography/mass spectrometry. The NR8383 cell line and freshly isolated neonatal guinea pig AM were exposed to ethyl oleate (EO) in vitro. MT membrane potential, MT reactive oxygen species generation (mROS), phagocytosis, and apoptosis were evaluated after exposure to EO ± the MT-specific antioxidant mito-TEMPO (mitoT) or ± the pan-caspase inhibitor Z-VAD-FMK. Whole lung FAEEs were compared using the Mann-Whitney U-test. Cellular results were analyzed using 1-way analysis of variance, followed by the Student-Newman-Keuls Method for post hoc comparisons. In utero ethanol significantly increased ethyl linoleate and the combinations of ethyl oleate + linoleate + linolenate (OLL), and OLL + stearate in the neonatal lung. In vitro EO caused significant MT dysfunction in both NR8383 and primary neonatal AM, as indicated by increased mROS and loss of MT membrane potential. Impaired phagocytosis and apoptosis were significantly increased in both the cell line and primary AM after EO exposure. MitoT conferred significant but only partial protection against EO-induced MT injury, as did caspase inhibition with Z-VAD-FMK. In utero ethanol exposure increased FAEEs in the neonatal guinea pig lung. Direct exposure to the FAEE EO significantly contributed to AM dysfunction, in part via oxidant injury to the MT and in part via secondary apoptosis. Copyright © 2015 The Authors

  14. Fatty Acid Ethyl Esters Disrupt Neonatal Alveolar Macrophage Mitochondria and Derange Cellular Functioning

    PubMed Central

    Mohan, Sowmya S; Ping, Xiao Du; Harris, Frank L; Ronda, Necol J; Brown, Lou Ann S; Gauthier, Theresa W

    2015-01-01

    Background Chronic alcohol exposure alters the function of alveolar macrophages (AM), impairing immune defenses in both adult and neonatal lungs. Fatty acid ethyl esters (FAEEs) are biological markers of prenatal alcohol exposure in newborns. FAEEs contribute to alcohol-induced mitochondrial (MT) damage in multiple organs. We hypothesized that in utero ethanol exposure would increase FAEEs in the neonatal lung and that direct exposure of neonatal AM to FAEEs would contribute to MT injury and cellular dysfunction. Methods FAEEs were measured in neonatal guinea pig lungs after ± in utero ethanol exposure via gas chromatography/mass spectrometry. The NR8383 cell line and freshly isolated neonatal guinea pig AM were exposed to ethyl oleate (EO) in vitro. MT membrane potential, MT reactive oxygen species generation (mROS), phagocytosis, and apoptosis were evaluated after exposure to EO ± the MT-specific antioxidant mito-TEMPO (mitoT) or ± the pan-caspase inhibitor Z-VAD-FMK. Whole lung FAEEs were compared using the Mann–Whitney U-test. Cellular results were analyzed using 1-way analysis of variance, followed by the Student–Newman–Keuls Method for post hoc comparisons. Results In utero ethanol significantly increased ethyl linoleate and the combinations of ethyl oleate + linoleate + linolenate (OLL), and OLL + stearate in the neonatal lung. In vitro EO caused significant MT dysfunction in both NR8383 and primary neonatal AM, as indicated by increased mROS and loss of MT membrane potential. Impaired phagocytosis and apoptosis were significantly increased in both the cell line and primary AM after EO exposure. MitoT conferred significant but only partial protection against EO-induced MT injury, as did caspase inhibition with Z-VAD-FMK. Conclusions In utero ethanol exposure increased FAEEs in the neonatal guinea pig lung. Direct exposure to the FAEE EO significantly contributed to AM dysfunction, in part via oxidant injury to the MT and in part via secondary

  15. Quantification of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in meconium for detection of alcohol abuse during pregnancy: Correlation study between both biomarkers.

    PubMed

    Cabarcos, Pamela; Tabernero, María Jesús; Otero, José Luís; Míguez, Martha; Bermejo, Ana María; Martello, Simona; De Giovanni, Nadia; Chiarotti, Marcello

    2014-11-01

    This article presents results from 47 meconium samples, which were analyzed for fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) for detection of gestational alcohol consumption. A validated microwave assisted extraction (MAE) method in combination with GC-MS developed in the Institute of Forensic Science (Santiago de Compostela) was used for FAEE and the cumulative concentration of ethyl myristate, ethyl palmitate and ethyl stearate with a cut-off of 600ng/g was applied for interpretation. A simple method for identification and quantification of EtG has been evaluated by ultrasonication followed solid phase extraction (SPE). Successful validation parameters were obtained for both biochemical markers of alcohol intake. FAEE and EtG concentrations in meconium ranged between values lower than LOD and 32,892ng/g or 218ng/g respectively. We have analyzed FAEE and EtG in the same meconium aliquot, enabling comparison of the efficiency of gestational ethanol exposure detection. Certain agreement between the two biomarkers was found as they are both a very specific alcohol markers, making it a useful analysis for confirmation. Copyright © 2014 Elsevier B.V. All rights reserved.

  16. ω-3 Fatty Acid Ethyl Esters Diminish Postprandial Lipemia in Familial Hypercholesterolemia.

    PubMed

    Chan, Dick C; Pang, Jing; Barrett, P Hugh R; Sullivan, David R; Burnett, John R; van Bockxmeer, Frank M; Watts, Gerald F

    2016-10-01

    Impaired postprandial chylomicron metabolism induces hypertriglyceridemia and may increase the risk of atherosclerotic cardiovascular disease. Omega-3 fatty acid ethyl ester (ω-3 FAEE) supplementation decreases plasma triglycerides. However, its effect on postprandial chylomicron metabolism in familial hypercholesterolemia (FH) has not yet been investigated. We aimed to examine the effect of ω-3 FAEE supplementation on postprandial responses in plasma triglycerides, very-low-density lipoprotein (VLDL) apolipoprotein B (apoB)-100, and apoB-48 in FH patients receiving standard cholesterol-lowering treatment. We carried out an 8-week open-label, randomized, crossover intervention trial to test the effect of oral supplementation with 4 g/d ω-3 FAEE (46% eicosapentaenoic acid and 38% docosahexaenoic acid) on postprandial triglyceride, VLDL-apoB-100, and apoB-48 responses in FH patients after ingestion of an oral fat load. Plasma total and incremental triglyceride, VLDL-apoB-100, and apoB-48 0- to 10-hour area under the curve (AUC). ω-3 FAEE supplementation significantly (P < .05 in all) reduced concentrations of fasting plasma triglyceride (-20%), apoB (-8%), VLDL-apoB-100 (-26%), and apoB-48 (-36%); as well as systolic blood pressure (-6%) and diastolic blood pressure (-6%). Postprandial triglyceride and VLDL-apoB-100 total AUCs (-19% and -26%, respectively; P < .01) and incremental AUCs (-18% and -35%, respectively; P < .05), as well as postprandial apoB-48 total AUC (-30%; P < .02) were significantly reduced by ω-3 FAEE supplementation. Supplementation with ω-3 FAEEs improves postprandial lipemia in FH patients receiving standard care; this may have implications for further reducing atherosclerotic cardiovascular disease in this high-risk patient group.

  17. Modulation of lipid peroxidation and antioxidant enzymes in murine salivary gland by dietary fatty acid ethyl esters.

    PubMed

    Avula, C P; Fernandes, G

    1999-01-01

    The present study was undertaken to investigate the effect of n-9, n-6, and n-3 dietary fatty acid ethyl esters on basal (uninduced) and Fe2+/ascorbate (induced) lipid peroxidation (LPO) in salivary gland (SG) of mice. Feeding n-3 ethyl ester polyunsaturated fatty acids (PUFA) increased the uninduced and induced LPO in SG homogenates. In contrast, feeding olive oil ethyl esters (n-9) significantly lowered the induced and uninduced LPO in SG tissue. Salivary gland susceptibility to LPO increased in the order of: olive oil < corn oil < safflower oil < n-3 ethyl esters. Olive oil esters in the diet increased primarily the 18:1 levels in SG tissue. Whereas feeding n-3 PUFA notably increased the superoxide dismutase (SOD) and catalase activities in SG homogenates, no significant changes were seen between n-9 and n-6 PUFA-fed mice. Lower levels of Vitamin E (Vit E) in the tissues of n-3 PUFA-fed mice indicate that the higher the dietary lipid unsaturation, the higher the requirement for Vit E in the diet. Our results indicate that, similar to other organs, salivary gland susceptibility to uninduced or induced oxidation depends on the source of dietary PUFA. In conclusion, feeding olive oil increases the resistance of SGs to induced and uninduced LPO.

  18. Production and Characterization of Ethyl Ester from Crude Jatropha curcas Oil having High Free Fatty Acid Content

    NASA Astrophysics Data System (ADS)

    Kumar, Rajneesh; Dixit, Anoop; Singh, Shashi Kumar; Singh, Gursahib; Sachdeva, Monica

    2015-09-01

    The two step process was carried out to produce biodiesel from crude Jatropha curcas oil. The pretreatment process was carried out to reduce the free fatty acid content by (≤2 %) acid catalyzed esterification. The optimum reaction conditions for esterification were reported to be 5 % H2SO4, 20 % ethanol and 1 h reaction time at temperature of 65 °C. The pretreatment process reduced the free fatty acid of oil from 7 to 1.85 %. In second process, alkali catalysed transesterification of pretreated oil was carried and the effects of the varying concentrations of KOH and ethanol: oil ratios on percent ester recovery were investigated. The optimum reaction conditions for transesterification were reported to be 3 % KOH (w/v of oil) and 30 % (v/v) ethanol: oil ratio and reaction time 2 h at 65 °C. The maximum percent recovery of ethyl ester was reported to be 60.33 %.

  19. Agreement between the fatty acid ethyl ester hair test for alcohol and social workers' reports.

    PubMed

    Kulaga, Vivian; Gareri, Joey; Fulga, Netta; Koren, Gideon

    2010-06-01

    The purpose of this study was to examine the relationship between social worker reports and the fatty acid ethyl ester (FAEE) test as a biomarker for heavy alcohol use. In 2005, a diagnostic program to detect excessive alcohol use by FAEE hair analysis in parents at high risk of having children with fetal alcohol spectrum disorders was established. All cases submitted by Child Protective Services between May and December of 2007 (n = 172) were included comparing social worker reports with FAEE test outcome by odds ratio analysis. A subanalysis of mothers (n = 119), excluding fathers, was also performed. Factors associated with testing positive for hair FAEE in parents, and mothers alone, were: knowledge of a specific instance of problem drinking within the past 6 months (odds ratio [OR] = 5.11, 2.57-10.16 and OR = 8.51, 3.59-20.18, respectively) and third party reports alleging alcohol abuse (OR = 3.31, 1.69-6.46 and OR = 3.30, 1.45-7.50, respectively). Mothers who admitted to heavy drinking were also seven times more likely to test positive for hair FAEE (OR = 6.74, 1.50-30.38) than those who did not. Factors negatively associated with testing positive for hair FAEE in parents, and mothers alone, were: social workers testing for FAEE without the suspicion of alcohol use but rather as a measure to "cover all bases" (OR = 0.09, 0.02-0.40 and (OR = 0.13, 0.03-0.58, respectively) or because of a history/suspicion of illicit drug use (OR = 0.2, 0.07-0.55 and OR = 0.26, 0.08-0.80, respectively). Eleven of 15 reports, indicating levels of consumption, were also in clinical agreement with FAEE test outcome. The FAEE hair test is being applied for the first time in the present context. Our results show the test corroborates well with social workers' suspicion of alcohol use. Reported factors directly related to alcohol use were significantly associated with testing positive for excessive alcohol use, whereas factors not directly related to alcohol use were negatively

  20. Identification and quantification of ethyl carbamate occurring in urea complexation processes commonly utilized for polyunsaturated fatty acid concentration.

    PubMed

    Vázquez, Luis; Prados, Isabel M; Reglero, Guillermo; Torres, Carlos F

    2017-08-15

    The concentration of polyunsaturated fatty acids by formation of urea adducts from three different sources was studied to elucidate the formation of ethyl carbamates in the course of these procedures. Two different methodologies were performed: with ethanol at high temperature and with hexane/ethanol mixtures at room temperature. It was proved that the amount of urethanes generated at high temperature was higher than at room temperature. Besides, subsequent washing steps of the PUFA fraction with water were efficient to remove the urethanes from the final products. The methodology at room temperature with 0.4mL ethanol and 3g urea provided good relationship between concentration and yield of the main bioactive PUFA, with the lowest formation of ethyl carbamates in the process. Copyright © 2017 Elsevier Ltd. All rights reserved.

  1. Quantification of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in meconium from newborns for detection of alcohol abuse in a maternal health evaluation study.

    PubMed

    Bakdash, Abdulsallam; Burger, Pascal; Goecke, Tamme W; Fasching, Peter A; Reulbach, Udo; Bleich, Stefan; Hastedt, Martin; Rothe, Michael; Beckmann, Matthias W; Pragst, Fritz; Kornhuber, Johannes

    2010-04-01

    Fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) were determined in 602 meconium samples in a maternal health evaluation study for detection of gestational alcohol consumption. A validated headspace solid phase microextraction method in combination with GC-MS was used for FAEE and the cumulative concentration of ethyl palmitate, ethyl linoleate, ethyl oleate, and ethyl stearate with a cut-off of 500 ng/g was applied for interpretation. A new and simple method was developed and validated for quantification of EtG from 10-20 mg meconium with D(5)-EtG as internal standard consisting of 30 min. extraction with methanol/water (1:1, v/v), evaporation of methanol, filtration of the aqueous solution through a cellulose filter and injection into LC-MS-MS. The limits of detection and quantification for EtG were 10 and 30 ng/g, the recovery 86.6 to 106.4% and the standard deviation of the concentrations ranged from 13% at 37 ng/g to 5% at 46,700 ng/g (N = 6). FAEE above the cut-off were found in 43 cases (7.1%) with cumulative concentrations between 507 and 22,580 ng/g and with one outlier of about 150,000 ng/g (EtG not detected). EtG was detected in 97 cases (16.3%) and concentrations between LOD and 10,200 ng/g with another outlier of 82,000 ng/g (FAEE 10,500 ng/g). Optimal agreement between the two markers was obtained with a cut-off for EtG of 274 ng/g and 547 cases with both FAEE- and EtG-negative, 33 cases with both FAEE- and EtG-positive, nine cases with FAEE-positive and EtG-negative, and seven cases with FAEE-negative and EtG-positive. Differences in physical, chemical, and biochemical properties and in the pharmacokinetic behavior are discussed as reasons for the deviating cases. In none of the 602 cases, serious alcohol consumption was reported by the mothers and no evidence for gestational ethanol exposure was observed in the medical investigation of the newborns. It is concluded that the combined use of FAEE and EtG in meconium as markers for fetal

  2. Biomarkers for detection of prenatal alcohol exposure: a critical review of fatty acid ethyl esters in meconium.

    PubMed

    Burd, Larry; Hofer, Ryan

    2008-07-01

    The objective of this study was a review of published studies utilizing measurement of fatty acid ethyl esters (FAEE) in meconium as biomarkers for prenatal alcohol exposure. We completed a literature search of PubMed using the terms meconium, fatty acid ethyl esters, biomarkers, and prenatal alcohol exposure. We included only peer reviewed studies utilizing analysis of meconium for the presence of FAEE in humans through the year 2007. We found 10 articles reporting on original research examining the relationship of FAEE from meconium and prenatal alcohol exposure (PAE). The 10 articles used six different PAE assessment strategies and four different analytical techniques for determining FAEE endpoints. The articles included 2,221 subjects (range 4 to 725) with 455 (20.5%) subjects identified as exposed using the methods stated in the articles. FAEE levels above the studies' respective cutoffs were reported for 502 (22.6%) subjects. The accurate identification of alcohol-exposed pregnancies represents a significant challenge in the development of FAEE detection cutoffs to maximize the sensitivity and specificity of the test. We present several options for the improvement of exposure assessment in future studies of FAEE as biomarkers for PAE. (c) 2008 Wiley-Liss, Inc.

  3. Raman Spectroscopy of Fish Oil Capsules: Polyunsaturated Fatty Acid Quantitation Plus Detection of Ethyl Esters and Oxidation.

    PubMed

    Killeen, Daniel P; Marshall, Susan N; Burgess, Elaine J; Gordon, Keith C; Perry, Nigel B

    2017-05-03

    Fish oils are the primary dietary source of ω-3 polyunsaturated fatty acids (PUFA), but these compounds are prone to oxidation, and commercial fish oil supplements sometimes contain less PUFA than claimed. These supplements are predominantly sold in softgel capsules. In this work, we show that Fourier transform (FT)-Raman spectra of fish oils (n = 5) and ω-3 PUFA concentrates (n = 6) can be acquired directly through intact softgel (gelatin) capsules. These spectra could be used to rapidly distinguish supplements containing ethyl esters from those containing triacylglyceride oils. Raman spectroscopy calibrated with partial least-squares regression against traditional fatty acid methyl ester analyses by gas chromatography-mass spectrometry could be used to rapidly and nondestructively quantitate PUFA and other fatty acid classes directly though capsules. We also show that FT-Raman spectroscopy can noninvasively detect oxidation with high sensitivity. Oils with peroxide values of as low as 10 mequiv kg(-1), which are on the cusp of falling outside of specification, could be readily distinguished from oils that were within specification (7 mequiv kg(-1)).

  4. Detecting alcohol abuse: traditional blood alcohol markers compared to ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) measurement in hair.

    PubMed

    Hastedt, Martin; Büchner, Mara; Rothe, Michael; Gapert, René; Herre, Sieglinde; Krumbiegel, Franziska; Tsokos, Michael; Kienast, Thorsten; Heinz, Andreas; Hartwig, Sven

    2013-12-01

    Alcohol abuse is a common problem in society; however, the technical capabilities of evaluating individual alcohol consumption using objective biomarkers are rather limited at present. In recent years research has focused on alcohol markers using hair analysis but data on performance and reliable cut-off values are still lacking. In this study 169 candidates were tested to compare traditional biomarkers, such as carbohydrate-deficient-transferrin (CDT), gamma glutamyl transferase (GGT), aspartate amino transferase, alanine amino transferase and the mean corpuscular volume of the erythrocytes, with alcohol markers detectable in hair such as ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs). This study revealed that EtG, GGT and CDT showed the best results, demonstrating areas under the curve calculated from receiver operating characteristics of 0.941, 0.943 and 0.899 respectively. The lowest false-negative and false-positive rates were obtained by using a combined interpretation system for hair EtG and FAEEs. All markers demonstrated only low to moderate correlations. Optimum cut-off values for differentiation between social and chronic excessive drinking calculated for hair EtG and FAEEs were 28 pg/mg and 0.675 ng/mg, respectively. The critical values published in the "Consensus on Alcohol Markers 2012" by the Society of Hair Testing were confirmed.

  5. Effect of supplementation with docosahexaenoic acid ethyl ester and sn-2 docosahexaenyl monoacylglyceride on plasma and erythrocyte fatty acids in rats.

    PubMed

    Valenzuela, Alfonso; Valenzuela, Viviana; Sanhueza, Julio; Nieto, Susana

    2005-01-01

    Docosahexaenoic acid (C22:6, DHA) is an omega-3 fatty acid required for the normal development of the mammalian nervous and visual system. DHA is provided by the mother during pregnancy and lactating period. Mother's DHA supplementation during pregnancy, and even before pregnancy, has been suggested. DHA can be provided by marine oils, egg's yolk phospholipids, single cell algae oils, the pure fatty acid, or by the ethyl ester derivative (DHA-EE). Another way to provide DHA can be by sn-2 docosahexaenyl monoacylglyceride (DHA-MG), obtained by the treatment of fish oil with stereospecific lipases. sn-2 Fatty acid monoacylglycerides can be more easily absorbed at the intestine than other fatty acid derivatives. Female rats fed with a synthetic, which provided essentially no DHA, received a 40-day supplementation of either DHA-EE or DHA-MG. Plasma and erythrocyte fatty acid composition were assessed by gas chromatography at day 0 and 40 of supplementation. DHA-EE increased plasma and erythrocyte DHA by 15 and 11.9%, respectively, with no modification of arachidonic acid (AA) content. DHA-MG supplementation increased plasma and erythrocyte DHA by 24 and 23.8%, respectively, but reduced AA by 5.5 and 3%, respectively. We conclude that in the rat, DHA-MG supplementation allows a higher plasma and erythrocyte DHA content than DHA-EE with minor modification of AA content. Copyright 2005 S. Karger AG, Basel.

  6. An improved method for rapidly quantifying fatty acid ethyl esters in meconium suitable for prenatal alcohol screening.

    PubMed

    Hutson, Janine R; Rao, Chitra; Fulga, Netta; Aleksa, Katarina; Koren, Gideon

    2011-03-01

    Fatty acid ethyl esters (FAEEs) are nonoxidative metabolites of ethanol, and elevated levels of FAEE in meconium are a useful biomarker for heavy prenatal alcohol exposure. FAEE in meconium has been recommended as useful and cost-effective for universal screening for prenatal alcohol exposure. To support an efficient universal screening program, an analytical method to detect and quantify FAEE in meconium needs to be accurate, inexpensive, and rapid. The purpose of this study was to develop an analytical method that would satisfy these criteria and to validate this method using established laboratory guidelines. A method was developed and validated to detect and quantify four FAEEs (ethyl palmitate, ethyl linoleate, ethyl oleate, and ethyl stearate) from 0.5 g of meconium using d(5)-ethyl esters as internal standards. The sample undergoes liquid-liquid extraction with heptane:acetone, the heptane layer is isolated and evaporated, and then, the resulting residue undergoes headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry. The detection limits of the four FAEEs ranged from 0.020 to 0.042 nmol/g and are 6- to 25-fold lower than the individual FAEE threshold concentrations (0.5 nmol/g). This method also has good precision with the coefficient of variation ranging from 2.6 to 19.4% for concentrations of individual FAEE between 0.5 and 2.62 nmol/g meconium (n=4). Calculated concentrations of FAEE that underwent extraction from meconium were 100-101% of the expected concentration, demonstrating the accuracy of the method. The peak shape and retention time of each FAEE were unaffected by the presence of the matrix, and there is no carryover at clinically relevant concentrations. This method was also able to produce clean chromatograms from meconium samples that could not be quantified using a previous method because of high chromatographic background. This method provides an optimal approach to detecting and quantifying FAEE in

  7. Two-step synthesis of fatty acid ethyl ester from soybean oil catalyzed by Yarrowia lipolytica lipase

    PubMed Central

    2011-01-01

    Background Enzymatic biodiesel production by transesterification in solvent media has been investigated intensively, but glycerol, as a by-product, could block the immobilized enzyme and excess n-hexane, as a solution aid, would reduce the productivity of the enzyme. Esterification, a solvent-free and no-glycerol-release system for biodiesel production, has been developed, and two-step catalysis of soybean oil, hydrolysis followed by esterification, with Yarrowia lipolytica lipase is reported in this paper. Results First, soybean oil was hydrolyzed at 40°C by 100 U of lipase broth per 1 g of oil with approximately 30% to 60% (vol/vol) water. The free fatty acid (FFA) distilled from this hydrolysis mixture was used for the esterification of FFA to fatty acid ethyl ester by immobilized lipase. A mixture of 2.82 g of FFA and equimolar ethanol (addition in three steps) were shaken at 30°C with 18 U of lipase per 1 gram of FFA. The degree of esterification reached 85% after 3 hours. The lipase membranes were taken out, dehydrated and subjected to fresh esterification so that over 82% of esterification was maintained, even though the esterification was repeated every 3 hours for 25 batches. Conclusion The two-step enzymatic process without glycerol released and solvent-free demonstrated higher efficiency and safety than enzymatic transesterification, which seems very promising for lipase-catalyzed, large-scale production of biodiesel, especially from high acid value waste oil. PMID:21366905

  8. An evaluation of washing and extraction techniques in the analysis of ethyl glucuronide and fatty acid ethyl esters from hair samples.

    PubMed

    Bossers, L C A M; Paul, R; Berry, A J; Kingston, R; Middendorp, C; Guwy, A J

    2014-03-15

    Ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) are alcohol metabolites measured in hair and are after a decade of research thought to be the best markers in hair to indicate alcoholism and abstinence Forensic Sci. Int. 218 (2012) 2. A great body of work concerning EtG and FAEEs detection in hair has been performed. However, no recent extensive comparison has been made concerning washing and extraction procedures. This work shows that the washing procedure of dichloromethane followed by a methanol rinse of the hair sample removes more than 16% of the FAEEs and 50% of the total EtG that is present in and on the hair. A review of ten washing protocols (where the removal is categorised: high, medium or low) showed that a relatively high percentage of FAEEs was removed and "medium" amount of EtG compared to the other washing protocols. This work shows promising results for the extraction of the FAEEs and the combined extraction of FAEEs and EtG by using 30min of sonication with methanol. More FAEEs were recovered from hair with methanol than with any other extraction solvent including the commonly used dimethyl sulfoxide/heptane mixture. When the sonication time was increased a higher percentage of transesterification of the FAEEs was observed, the extraction was "dirtier" as solids and a colour change was observed whereas the extraction efficiency did not increase. Therefore, washing the hair sample with dichloromethane and methanol followed by an addition of 1ml of methanol and sonication for 30min to extract the FAEEs and EtG from hair is recommended for FAEEs as well as for the combined analysis of EtG and FAEEs. A linear calibration curve (r(2)>0.99) was obtained for all analytes. Copyright © 2014 Elsevier B.V. All rights reserved.

  9. Synthesis of fatty acid ethyl esters in mammalian tissues after ethanol exposure: a systematic review of the literature.

    PubMed

    Zelner, Irene; Matlow, Jeremy N; Natekar, Aniket; Koren, Gideon

    2013-08-01

    The ability to undergo non-oxidative metabolism from ethanol to fatty acid ethyl esters (FAEEs) varies greatly among tissues and organs. To gain a greater understanding of non-oxidative ethanol metabolism to FAEE, we aimed to collect all published data on FAEE synthesis in mammalian organs and tissues to identify all tissues, organs, and enzymes that are known to, or likely possess FAEE-synthetic activity. A systematic search for relevant papers was performed and two independent reviewers examined potentially relevant abstracts (articles on FAEEs that pertain to ethanol exposure) to determine whether they met the inclusion criteria. Information on FAEE synthesis was retrieved from papers meeting the inclusion/exclusion criteria and summarized by organ/tissue/matrix examined. The systematic search through four databases yielded 78 articles that investigated FAEE synthesis by tissues, tissue fractions and cell lines, and 29 articles that attempted to purify and/or characterize the enzymes involved in FAEE synthesis. Two enzyme activities have been studied: FAEE synthase (FAEES, which conjugates ethanol and free fatty acid) and acyl-CoA: ethanol O-acyltransferase (AEAT, which conjugates ethanol and fatty acyl-CoA). Both activities are expressed by a variety of different enzymes. FAEES activity is the most widely studied and has been purified from several tissues and shown to be associated with several well-known enzymes, while the identity of enzymes possessing AEAT activity remains unknown. The organs and tissues that have been shown to synthesize FAEEs are discussed, with special emphasis on the studies that attempted to elucidate the enzymology of FAEE synthesis in those tissues.

  10. Validation of a novel method to identify in utero ethanol exposure: simultaneous meconium extraction of fatty acid ethyl esters, ethyl glucuronide, and ethyl sulfate followed by LC-MS/MS quantification

    PubMed Central

    Himes, Sarah K.; Concheiro, Marta; Scheidweiler, Karl B.

    2015-01-01

    Presence of fatty acid ethyl esters (FAEE), ethyl glucuronide (EtG), and ethyl sulfate (EtS) in meconium, the first neonatal feces, identifies maternal alcohol consumption during pregnancy. Current meconium alcohol marker assays require separate analyses for FAEE and EtG/EtS. We describe development and validation of the first quantitative liquid chromatography tandem mass spectrometry assay for 9 FAEEs, EtG, and EtS in 100 mg meconium. For the first time, these alcohol markers are analyzed in the same meconium aliquot, enabling comparison of the efficiency of gestational ethanol exposure detection. 100 mg meconium was homogenized in methanol and centrifuged. The supernatant was divided, and applied to two different solid phase extraction columns for optimized analyte recovery. Limits of quantification for ethyl laurate, myristate, linolenate, palmitoleate, arachidonate, linoleate, palmitate, oleate, and stearate ranged from 25–50 ng/g, with calibration curves to 2,500–5,000 ng/g. EtG and EtS linear dynamic ranges were 5–1,000 and 2.5–500 ng/g, respectively. Mean bias and between-day imprecision were <15 %. Extraction efficiencies were 51.2–96.5 %. Matrix effects ranged from −84.7 to 16.0 %, but were compensated for by matched deuterated internal standards when available. All analytes were stable (within ±20 % change from baseline) in 3 authentic positive specimens, analyzed in triplicate, after 3 freeze/thaw cycles (−20 °C). Authentic EtG and EtS also were stable after 12 h at room temperature and 72 h at 4 °C; some FAEE showed instability under these conditions, although there was large inter-subject variability. This novel method accurately detects multiple alcohol meconium markers and enables comparison of markers for maternal alcohol consumption. PMID:24408304

  11. Validation of a novel method to identify in utero ethanol exposure: simultaneous meconium extraction of fatty acid ethyl esters, ethyl glucuronide, and ethyl sulfate followed by LC-MS/MS quantification.

    PubMed

    Himes, Sarah K; Concheiro, Marta; Scheidweiler, Karl B; Huestis, Marilyn A

    2014-03-01

    Presence of fatty acid ethyl esters (FAEE), ethyl glucuronide (EtG), and ethyl sulfate (EtS) in meconium, the first neonatal feces, identifies maternal alcohol consumption during pregnancy. Current meconium alcohol marker assays require separate analyses for FAEE and EtG/EtS. We describe development and validation of the first quantitative liquid chromatography tandem mass spectrometry assay for 9 FAEEs, EtG, and EtS in 100 mg meconium. For the first time, these alcohol markers are analyzed in the same meconium aliquot, enabling comparison of the efficiency of gestational ethanol exposure detection. 100 mg meconium was homogenized in methanol and centrifuged. The supernatant was divided, and applied to two different solid phase extraction columns for optimized analyte recovery. Limits of quantification for ethyl laurate, myristate, linolenate, palmitoleate, arachidonate, linoleate, palmitate, oleate, and stearate ranged from 25-50 ng/g, with calibration curves to 2,500-5,000 ng/g. EtG and EtS linear dynamic ranges were 5-1,000 and 2.5-500 ng/g, respectively. Mean bias and between-day imprecision were <15 %. Extraction efficiencies were 51.2-96.5 %. Matrix effects ranged from -84.7 to 16.0 %, but were compensated for by matched deuterated internal standards when available. All analytes were stable (within ±20 % change from baseline) in 3 authentic positive specimens, analyzed in triplicate, after 3 freeze/thaw cycles (-20 °C). Authentic EtG and EtS also were stable after 12 h at room temperature and 72 h at 4 °C; some FAEE showed instability under these conditions, although there was large inter-subject variability. This novel method accurately detects multiple alcohol meconium markers and enables comparison of markers for maternal alcohol consumption.

  12. Fatty acid ethyl ester synthase inhibition ameliorates ethanol-induced Ca2+-dependent mitochondrial dysfunction and acute pancreatitis.

    PubMed

    Huang, Wei; Booth, David M; Cane, Matthew C; Chvanov, Michael; Javed, Muhammad A; Elliott, Victoria L; Armstrong, Jane A; Dingsdale, Hayley; Cash, Nicole; Li, Yan; Greenhalf, William; Mukherjee, Rajarshi; Kaphalia, Bhupendra S; Jaffar, Mohammed; Petersen, Ole H; Tepikin, Alexei V; Sutton, Robert; Criddle, David N

    2014-08-01

    Non-oxidative metabolism of ethanol (NOME) produces fatty acid ethyl esters (FAEEs) via carboxylester lipase (CEL) and other enzyme action implicated in mitochondrial injury and acute pancreatitis (AP). This study investigated the relative importance of oxidative and non-oxidative pathways in mitochondrial dysfunction, pancreatic damage and development of alcoholic AP, and whether deleterious effects of NOME are preventable. Intracellular calcium ([Ca(2+)](C)), NAD(P)H, mitochondrial membrane potential and activation of apoptotic and necrotic cell death pathways were examined in isolated pancreatic acinar cells in response to ethanol and/or palmitoleic acid (POA) in the presence or absence of 4-methylpyrazole (4-MP) to inhibit oxidative metabolism. A novel in vivo model of alcoholic AP induced by intraperitoneal administration of ethanol and POA was developed to assess the effects of manipulating alcohol metabolism. Inhibition of OME with 4-MP converted predominantly transient [Ca(2+)](C) rises induced by low ethanol/POA combination to sustained elevations, with concurrent mitochondrial depolarisation, fall of NAD(P)H and cellular necrosis in vitro. All effects were prevented by 3-benzyl-6-chloro-2-pyrone (3-BCP), a CEL inhibitor. 3-BCP also significantly inhibited rises of pancreatic FAEE in vivo and ameliorated acute pancreatic damage and inflammation induced by administration of ethanol and POA to mice. A combination of low ethanol and fatty acid that did not exert deleterious effects per se became toxic when oxidative metabolism was inhibited. The in vitro and in vivo damage was markedly inhibited by blockade of CEL, indicating the potential for development of specific therapy for treatment of alcoholic AP via inhibition of FAEE generation. Published by the BMJ Publishing Group Limited. For permission to use (where not already granted under a licence) please go to http://group.bmj.com/group/rights-licensing/permissions.

  13. Practical experiences in application of hair fatty acid ethyl esters and ethyl glucuronide for detection of chronic alcohol abuse in forensic cases.

    PubMed

    Suesse, S; Pragst, F; Mieczkowski, T; Selavka, C M; Elian, A; Sachs, H; Hastedt, M; Rothe, M; Campbell, J

    2012-05-10

    This article presents results from 1872 hair samples, which were analyzed for fatty acid ethyl esters (FAEEs) and ethyl glucuronide (EtG). The results were evaluated in the context of self-reported drinking behavior, the use of hair cosmetics, the gender of the sample donors and hair sample length. For comparison, CDT and GGT in serum were available in 477 and 454 cases, respectively. A number of alcohol abstainers or low moderate drinkers and excessive drinkers were selected for assessment of cut-offs for FAEEs in the proximal 6cm hair segments and for EtG in the proximal 3cm hair segments. Cut-off values were assessed by ROC analysis. It was found that the cut-offs of 1.0ng/mg FAEE and 30pg/mg EtG presently used for excessive drinking lead to a low portion of false positives (4% and 3% respectively) but to a higher portion of false negatives (23% and 25% respectively). Comparison of the mean and medium concentrations in samples without any reported hair cosmetics (N=1079) and in samples with reported use of hair spray (N=79) showed an increase by the factor of about two for FAEE but no significant difference for EtG. Mean values of EtG were decreased by 80% in bleached samples (N=164) and by 63% in dyed samples (N=96). There was no significant effect of bleaching and dyeing on FAEE. Hair gel and hair wax, oil or grease showed no significant effect on both FAEE and EtG. With respect to gender and investigated hair length ambiguous results were obtained because of major differences in the compared subpopulations of male with higher alcohol consumption and mainly shorter hair, and less drinking female with longer hair. For excessive drinkers FAEEs in the 0-6cm hair segment and EtG in the 0-3cm segment decreased with increasing time of reported abstinence before sample collection. These drinkers attain the level of teetotalers only after more than 10 months of abstinence. In comparison to scalp hair, FAEEs recovered from armpit hair and leg hair were lower and from

  14. Fatty acids - trans fatty acids

    USDA-ARS?s Scientific Manuscript database

    The data supporting a negative effect of dietary trans fatty acids on cardiovascular disease risk is consistent. The primary dietary sources of trans fatty acids include partially hydrogenated fat and rudiment fat. The adverse effect of trans fatty acids on plasma lipoprotein profiles is consisten...

  15. Effect of omega-3 fatty acid ethyl esters on the oxylipin composition of lipoproteins in hypertriglyceridemic, statin-treated subjects.

    PubMed

    Newman, John W; Pedersen, Theresa L; Brandenburg, Verdayne R; Harris, William S; Shearer, Gregory C

    2014-01-01

    Oxylipins mediate inflammation, vascular tension, and more. Their presence in lipoproteins could explain why lipoproteins mediate nearly identical activities. To determine how oxylipins are distributed in the lipoproteins of hypertriglyceridemic subjects, and whether omega-3 fatty acids alter them in a manner consistent with improved cardiovascular health, we recruited 15 dyslipidemic subjects whose levels of low density lipoprotein cholesterol (LDL-C) were at goal but who remained hypertriglyceridemic (200-499 mg/dL). They were treated them with the indicated dose of 4 g/d omega-3 acid ethyl esters (P-OM3) for 8 weeks. Measured oxylipins included mid-chain alcohols (HETEs, HEPEs and HDoHEs), ketones (KETEs), epoxides (as EpETrEs, EpETEs, and EpDPEs). At baseline, arachidonate-oxylipins (HETEs, KETEs, and EpETrEs) were most abundant in plasma with the greatest fraction of total abundance (mean |95% CI|) being carried in high density lipoproteins (HDL); 42% |31, 57| followed by very low density lipoproteins (VLDL); 27% |20, 36|; and LDL 21% |16, 28|. EPA- and DHA-derived oxylipins constituted less than 11% of total. HDL carried alcohols and epoxides but VLDL was also rich in ketones. Treatment decreased AA-derived oxylipins across lipoprotein classes (-23% |-33, -12|, p = 0.0003), and expanded EPA-(322% |241, 422|, p<0.0001) and DHA-derived oxylipins (123% |80, 176|, p<0.0001). Each lipoprotein class carries a unique oxylipin complement. P-OM3 treatment alters the oxylipin content of all classes, reducing pro-inflammatory and increasing anti-inflammatory species, consistent with the improved inflammatory and vascular status associated with the treatment. ClinicalTrials.gov NCT00959842.

  16. Effect of Omega-3 Fatty Acid Ethyl Esters on the Oxylipin Composition of Lipoproteins in Hypertriglyceridemic, Statin-Treated Subjects

    PubMed Central

    Newman, John W.; Pedersen, Theresa L.; Brandenburg, Verdayne R.; Harris, William S.; Shearer, Gregory C.

    2014-01-01

    Background Oxylipins mediate inflammation, vascular tension, and more. Their presence in lipoproteins could explain why lipoproteins mediate nearly identical activities. Methods To determine how oxylipins are distributed in the lipoproteins of hypertriglyceridemic subjects, and whether omega-3 fatty acids alter them in a manner consistent with improved cardiovascular health, we recruited 15 dyslipidemic subjects whose levels of low density lipoprotein cholesterol (LDL-C) were at goal but who remained hypertriglyceridemic (200–499 mg/dL). They were treated them with the indicated dose of 4 g/d omega-3 acid ethyl esters (P-OM3) for 8 weeks. Measured oxylipins included mid-chain alcohols (HETEs, HEPEs and HDoHEs), ketones (KETEs), epoxides (as EpETrEs, EpETEs, and EpDPEs). Results At baseline, arachidonate-oxylipins (HETEs, KETEs, and EpETrEs) were most abundant in plasma with the greatest fraction of total abundance (mean |95% CI|) being carried in high density lipoproteins (HDL); 42% |31, 57| followed by very low density lipoproteins (VLDL); 27% |20, 36|; and LDL 21% |16, 28|. EPA- and DHA-derived oxylipins constituted less than 11% of total. HDL carried alcohols and epoxides but VLDL was also rich in ketones. Treatment decreased AA-derived oxylipins across lipoprotein classes (−23% |−33, −12|, p = 0.0003), and expanded EPA−(322% |241, 422|, p<0.0001) and DHA-derived oxylipins (123% |80, 176|, p<0.0001). Conclusions Each lipoprotein class carries a unique oxylipin complement. P-OM3 treatment alters the oxylipin content of all classes, reducing pro-inflammatory and increasing anti-inflammatory species, consistent with the improved inflammatory and vascular status associated with the treatment. Trial Registration ClinicalTrials.gov NCT00959842 PMID:25393536

  17. One-step enzymatic production of fatty acid ethyl ester from high-acidity waste feedstocks in solvent-free media.

    PubMed

    Véras, Ilvania C; Silva, Frederico A L; Ferrão-Gonzales, Astria D; Moreau, Vitor Hugo

    2011-10-01

    This work aims to demonstrate the enzymatic production of fatty acid ethyl ester biodiesel from highly acidic feedstock in a single-step reaction, without co-solvents and avoiding the inhibition of the enzyme by ethanol and glycerol. Additionally, an empirical equation is proposed to predict the kinetics of the production reaction as a function of the used feedstock and catalyst concentration. Biodiesel production from highly acidic feedstock perform via simultaneous esterification of free fatty acids and transesterification of triacylglycerols. Enzymatic catalysis is one of the most promising alternative technologies for the biodiesel production. Increasing of the enzymatic bioactivity is crucial for the success of such process in industrial scale. Currently, stepwise addition of the alcohol or the use of co-solvents have been proposed to avoid enzyme inhibition, such strategies add downstream processes to the production. These results can be applied to the development economical-viable enzymatic production of biodiesel in industrial scale. Copyright © 2011 Elsevier Ltd. All rights reserved.

  18. Engineering of chromosomal wax ester synthase integrated Saccharomyces cerevisiae mutants for improved biosynthesis of fatty acid ethyl esters.

    PubMed

    Shi, Shuobo; Valle-Rodríguez, Juan Octavio; Siewers, Verena; Nielsen, Jens

    2014-09-01

    In recent years, significant advances have been made to engineer robust microbes for overproducing biochemical products from renewable resources. These accomplishments have to a large extend been based on plasmid based methods. However, plasmid maintenance may cause a metabolic burden on the host cell and plasmid-based overexpression of genes can result in genetically unstable strains, which contributes to loss in productivity. Here, a chromosome engineering method based on delta integration was applied in Saccharomyces cerevisiae for the production of fatty acid ethyl esters (FAEEs), which can be directly used as biodiesel and would be a possible substitute for conventional petroleum-based diesel. An integration construct was designed and integrated into chromosomal delta sequences by repetitive transformation, which resulted in 1-6 copies of the integration construct per genome. The corresponding FAEE production increased up to 34 mg/L, which is an about sixfold increase compared to the equivalent plasmid-based producer. The integrated cassette in the yeast genome was stably maintained in nonselective medium after deletion of RAD52 which is essential for efficient homologous recombination. To obtain a further increase of FAEE production, genes encoding endogenous acyl-CoA binding protein (ACB1) and a bacterial NADP(+)-dependent glyceraldehyde-3-phosphate dehydrogenase (gapN) were overexpressed in the final integration strain, which resulted in another 40% percent increase in FAEE production. Our integration strategy enables easy engineering of strains with adjustable gene copy numbers integrated into the genome and this allows for an easy evaluation of the effect of the gene copy number on pathway flux. It therefore represents a valuable tool for introducing and expressing a heterologous pathway in yeast.

  19. Omega-3 fatty acid ethyl ester supplementation decreases very-low-density lipoprotein triacylglycerol secretion in obese men.

    PubMed

    Wong, Annette T Y; Chan, Dick C; Ooi, Esther M M; Ng, Theodore W K; Watts, Gerald F; Barrett, P Hugh R

    2013-03-13

    Dysregulated VLDL-TAG (very-low-density lipoprotein triacylglycerol) metabolism in obesity may account for hypertriacylglycerolaemia and increased cardiovascular disease. ω-3 FAEEs (omega-3 fatty acid ethyl esters) decrease plasma TAG and VLDL concentrations, but the mechanisms are not fully understood. In the present study, we carried out a 6-week randomized, placebo-controlled study to examine the effect of high-dose ω-3 FAEE supplementation (3.2 g/day) on the metabolism of VLDL-TAG in obese men using intravenous administration of d5-glycerol. We also explored the relationship of VLDL-TAG kinetics with the metabolism of VLDL-apo (apolipoprotein) B-100 and HDL (high-density lipoprotein)-apoA-I. VLDL-TAG isotopic enrichment was measured using gas chromatography-mass spectrometry. Kinetic parameters were derived using a multicompartmental model. Compared with placebo, ω-3 FAEE supplementation significantly lowered plasma concentrations of total (-14%, P<0.05) and VLDL-TAG (-32%, P<0.05), as well as hepatic secretion of VLDL-TAG (-32%, P<0.03). The FCR (fractional catabolic rate) of VLDL-TAG was not altered by ω-3 FAEEs. There was a significant association between the change in secretion rates of VLDL-TAG and VLDL-apoB-100 (r=0.706, P<0.05). However, the change in VLDL-TAG secretion rate was not associated with change in HDL-apoA-I FCR (r=0.139, P>0.05). Our results suggest that the TAG-lowering effect of ω-3 FAEEs is associated with the decreased VLDL-TAG secretion rate and hence lower plasma VLDL-TAG concentration in obesity. The changes in VLDL-TAG and apoB-100 kinetics are closely coupled.

  20. Direct quantitative gas chromatographic separation of C2-C6 fatty acids, methanol, and ethyl alcohol in aqueous microbial fermentation media.

    PubMed

    Rogosa, M; Love, L L

    1968-02-01

    A method is described for the direct quantitative gas chromatographic separation of C(2)-C(6) lower fatty acid homologues, methanol, and ethyl alcohol in aqueous microbial fermentation media. A hydrogen flame detector and a single-phase solid column packing, comprising beads of a polyaromatic resin (polystyrene cross-linked with divinyl benzene), were employed. Direct injections of 1 to 10 muliters of aqueous culture supernatant fluids were made. Quantitative recoveries of C(2)-C(6) acids added to culture supernatant fluids were obtained.

  1. Direct Quantitative Gas Chromatographic Separation of C2-C6 Fatty Acids, Methanol, and Ethyl Alcohol in Aqueous Microbial Fermentation Media

    PubMed Central

    Rogosa, M.; Love, L. L.

    1968-01-01

    A method is described for the direct quantitative gas chromatographic separation of C2-C6 lower fatty acid homologues, methanol, and ethyl alcohol in aqueous microbial fermentation media. A hydrogen flame detector and a single-phase solid column packing, comprising beads of a polyaromatic resin (polystyrene cross-linked with divinyl benzene), were employed. Direct injections of 1 to 10 μliters of aqueous culture supernatant fluids were made. Quantitative recoveries of C2-C6 acids added to culture supernatant fluids were obtained. PMID:5645415

  2. Increase of medium-chain fatty acid ethyl ester content in mixed H. uvarum/S. cerevisiae fermentation leads to wine fruity aroma enhancement.

    PubMed

    Hu, Kai; Jin, Guo-Jie; Mei, Wen-Chao; Li, Ting; Tao, Yong-Sheng

    2018-01-15

    Medium-chain fatty acid (MCFA) ethyl esters, as yeast secondary metabolites, significantly contribute to the fruity aroma of foods and beverages. To improve the MCFA ethyl ester content of wine, mixed fermentations with Hanseniaspora uvarum Yun268 and Saccharomyces cerevisiae were performed. Final volatiles were analyzed by gas solid phase microextraction-chromatography-mass spectrometry, and aroma characteristics were quantitated by sensory analysis. Results showed that mixed fermentation increased MCFA ethyl ester content by 37% in Cabernet Gernischt wine compared to that obtained by pure fermentation. Partial least-squares regression analysis further revealed that the improved MCFA ethyl esters specifically enhanced the temperate fruity aroma of wine. The enhancement of MCFA ethyl esters was attributed to the increased contents of MCFAs that could be induced by the presence of H. uvarum Yun268 in mixed fermentation. Meanwhile, the timing of yeast inoculations significantly affected the involving biomass of each strain and the dynamics of ethanol accumulation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. Effect of hair care and hair cosmetics on the concentrations of fatty acid ethyl esters in hair as markers of chronically elevated alcohol consumption.

    PubMed

    Hartwig, Sven; Auwärter, Volker; Pragst, Fritz

    2003-01-28

    Fatty acid ethyl esters (FAEE) can be used as alcohol markers in hair. It was investigated in this study whether this diagnostic method is disturbed by hair care and hair cosmetics. Traces of ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate were detected in all of 49 frequently applied hair care products by headspace solid phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS). The highest concentration was 0.003% in a hair wax. From experiments with separated hair samples of alcoholics as well as from the evaluation of the FAEE concentrations and the data about hair care of 75 volunteers (alcoholics, social drinkers and teetotalers) follows that usual shampooing, permanent wave, dyeing, bleaching or shading are of minor importance as compared to the drinking amount and other individual features. However, false positive results were found after daily treatment with a hair lotion containing 62.5% ethanol, with a deodorant and with a hair spray. As an explanation, it is assumed that FAEE are formed in the sebum glands also after regular topical application of products with a higher ethanol content.

  4. Determination of fatty acid ethyl esters in dried blood spots by LC-MS/MS as markers for ethanol intake: application in a drinking study.

    PubMed

    Luginbühl, Marc; Schröck, Alexandra; König, Stefan; Schürch, Stefan; Weinmann, Wolfgang

    2016-05-01

    The forensic utility of fatty acid ethyl esters (FAEEs) in dried blood spots (DBS) as short-term confirmatory markers for ethanol intake was examined. An LC-MS/MS method for the determination of FAEEs in DBS was developed and validated to investigate FAEE formation and elimination in a drinking study, whereby eight subjects ingested 0.66-0.84 g/kg alcohol to reach blood alcohol concentrations (BAC) of 0.8 g/kg. Blood was taken every 1.5-2 h, BAC was determined, and dried blood spots were prepared, with 50 μL of blood, for the determination of FAEEs. Lower limits of quantitation (LLOQ) were between 15 and 37 ng/mL for the four major FAEEs. Validation data are presented in detail. In the drinking study, ethyl palmitate and ethyl oleate proved to be the two most suitable markers for FAEE determination. Maximum FAEE concentrations were reached in samples taken 2 or 4 h after the start of drinking. The following mean peak concentrations (c̅(max)) were reached: ethyl myristate 14 ± 4 ng/mL, ethyl palmitate 144 ± 35 ng/mL, ethyl oleate 125 ± 55 ng/mL, ethyl stearate 71 ± 21 ng/mL, total FAEEs 344 ± 91 ng/mL. Detectability of FAEEs was found to be on the same time scale as BAC. In liquid blood samples containing ethanol, FAEE concentrations increase post-sampling. This study shows that the use of DBS fixation prevents additional FAEE formation in blood samples containing ethanol. Positive FAEE results obtained by DBS analysis can be used as evidence for the presence of ethanol in the original blood sample.

  5. Alteration of seed fatty acid composition by an ethyl methanesulfonate-induced mutation in Arabidopsis thaliana affecting diacylglycerol acyltransferase activity.

    PubMed Central

    Katavic, V; Reed, D W; Taylor, D C; Giblin, E M; Barton, D L; Zou, J; Mackenzie, S L; Covello, P S; Kunst, L

    1995-01-01

    In characterizing the enzymes involved in the formation of very long-chain fatty acids (VLCFAs) in the Brassicaceae, we have generated a series of mutants of Arabidopsis thaliana that have reduced VLCFA content. Here we report the characterization of a seed lipid mutant, AS11, which, in comparison to wild type (WT), has reduced levels of 20:1 and 18:1 and accumulates 18:3 as the major fatty acid in triacylglycerols. Proportions of 18:2 remain similar to WT. Genetic analyses indicate that the fatty acid phenotype is caused by a semidominant mutation in a single nuclear gene, designated TAG1, located on chromosome 2. Biochemical analyses have shown that the AS11 phenotype is not due to a deficiency in the capacity to elongate 18:1 or to an increase in the relative delta 15 or delta 12 desaturase activities. Indeed, the ratio of desaturase/elongase activities measured in vitro is virtually identical in developing WT and AS11 seed homogenates. Rather, the fatty acid phenotype of AS11 is the result of reduced diacylglycerol acyltransferase activity throughout development, such that triacylglycerol biosynthesis is reduced. This leads to a reduction in 20:1 biosynthesis during seed development, leaving more 18:1 available for desaturation. Thus, we have demonstrated that changes to triacylglycerol biosynthesis can result in dramatic changes in fatty acid composition and, in particular, in the accumulation of VLCFAs in seed storage lipids. PMID:7784510

  6. Squalene in hair--a natural reference substance for the improved interpretation of fatty acid ethyl ester concentrations with respect to alcohol misuse.

    PubMed

    Auwärter, V; Kiessling, B; Pragst, F

    2004-10-29

    Fatty acid ethyl esters (FAEE) are incorporated into hair mainly from sebum. For this reason, the use of their concentration CFAEE as marker of excessive alcohol consumption is complicated by interindividual differences of the activity of the sebum glands and of elimination by hair care and hair cosmetics. Furthermore, an influence of the investigated hair length due to increasing accumulation from proximal to distal was found. Therefore, it was examined whether these sources of error can be avoided if in addition to CFAEE the relative FAEE concentrations CFAEE/CSQ related to squalene SQ as a natural reference compound were used for interpretation. Sebum contains about 10-20% SQ. A sensitive and reliable method for the determination of SQ in addition to FAEE from the same hair extracts by high performance liquid chromatography with photo diode array detector (HPLC-DAD) was developed. The concentrations of ethyl myristate, ethyl palmitate, ethyl oleate, ethyl stearate and squalene were determined and CFAEE/CSQ was calculated for 13 teetotallers, 16 social drinkers, 12 fatalities with excessive alcohol abuse at life time and 9 cases with unclear alcohol anamnesis. CSQ ranged from 0.02 to 1.97 microg/mg (mean 0.67 microg/mg). From the results follows that squalene enables a control of the lipid content of hair and a correction of CFAEE in cases with deviations from the usual lipid content in a similar way as creatinine in urine. Preliminary values of CFAEE/CSQ were suggested for the upper limit for teetotallers (< 0.6 ng/microg) and the lower limit for excessive alcohol abuse (> 1.5 ng/microg). However, the relative concentration CFAEE/CSQ cannot completely replace the absolute concentration CFAEE, and both should regularly be used for an improved interpretation with respect to alcohol abuse.

  7. Fatty acid ethyl esters in hair: correlation with self-reported ethanol intake in 160 subjects and influence of estroprogestin therapy.

    PubMed

    Bertol, Elisabetta; Del Bravo, Ester; Vaiano, Fabio; Mari, Francesco; Favretto, Donata

    2014-09-01

    Fatty acid ethyl esters (FAEEs) are minor ethanol metabolites that can accumulate in hair. The performance of hair FAEEs as a biomarker that can discriminate null or moderate drinking from risky, excessive drinking was verified by evaluating the relationship between self-reported daily alcohol intake and FAEE concentration in hair. The study subjects were 160 healthy volunteers (52% female) that included teetotallers, moderate/social drinkers (< 60 g of ethanol per day), and heavy drinkers (≥ 60 g/day).The estimated daily alcohol intake (EDAI) was assessed by a specific written questionnaire aimed at estimating the measure and the frequency of alcohol drinking and at excluding confounding factors. FAEEs (ethyl myristate, ethyl palmitate, ethyl oleate, and ethyl stearate) were extracted from the hair matrix by overnight incubation in n-hexane/dimethylsulphoxide, purified by solid-phase extraction (SPE) and analyzed by gas chromatography-mass spectrometry (GC-MS) in selected ion monitoring and Electron ionization (EI) mode, using pentadeuterated internal standards. Hair samples exhibited FAEE concentrations (expressed as the sum of the four esters, CFAEE ) ranging from 0.01 to 10.78 ng/mg (average 1.16 and median 0.60 ng/mg). The EDAI was from 0 to 246 g of ethanol per day, average 28 g/day and median 15 g/day. A cut-off of 0.5 ng/mg in 3 cm of a proximal hair segment was adopted to discriminate social drinking from excessive ethanol consumption. False positive samples were identified in subjects using ethanol-containing hair lotions and women on estroprogestin therapy. Specificity of 87% was reached when the identified false positives were excluded from data elaboration. CFAEE in hair at a predetermined cut-off can be used to discriminate between moderate and excessive drinking only when confounding factors are meticulously removed. Copyright © 2014 John Wiley & Sons, Ltd.

  8. Toxic fluorine compounds. The use of the ω-fluorine atom in the study of the metabolism of fatty acids containing ethyl, n-propyl and isopropyl branches

    PubMed Central

    Pattison, F. L. M.; Peters, D. A. V.

    1966-01-01

    1. Some ω-fluoroalkanoic acids containing a branched ethyl, n-propyl or isopropyl group in the α- or β-position have been prepared. 2. A study of the toxicity of these acids revealed that the ethyl group partially inhibited, and the n-propyl and isopropyl groups completely inhibited, the normal processes of oxidative degradation. PMID:5911518

  9. ω-3 Fatty Acids Ethyl Esters Suppress Cerebral Vasospasm and Improve Clinical Outcome Following Aneurysmal Subarachnoid Hemorrhage.

    PubMed

    Nakagawa, Ichiro; Yokoyama, Shohei; Omoto, Koji; Takeshima, Yasuhiro; Matsuda, Ryosuke; Nishimura, Fumihiko; Yamada, Shuichi; Yokota, Hiroshi; Motoyama, Yasushi; Park, Young-Su; Nakase, Hiroyuki

    2017-03-01

    Occurrence of cerebral vasospasm after onset of aneurysmal subarachnoid hemorrhage (SAH) is a critical factor determining clinical prognosis. Eicosapentaenoic acid and docosahexaenoic acid, both ω-3 fatty acids (ω-3FA), can suppress cerebral vasospasm, and docosahexaenoic acid can relax vessel vasoconstriction and have neuroprotective effects. We investigated whether administration of ω-3FA prevented cerebral vasospasm occurrence and improved clinical outcomes after aneurysmal SAH. From 2012 to 2015, 100 consecutive patients with aneurysmal SAH were divided into 2 periods. Between 2012 and 2013 (control period), 45 patients received standard management. Between 2014 and 2015 (ω-3FA period), 55 patients were prospectively treated with additional ω-3FA. Occurrence of cerebral vasospasm, occurrence of cerebral infarction caused by vasospasm, and modified Rankin Scale scores at 30 days and 90 days after onset of SAH for each period were evaluated and compared. The frequency of angiographic cerebral vasospasm in the ω-3FA period was significantly lower than in the control period (12 patients vs. 23 patients, P = 0.004). The frequency of new infarction caused by vasospasm in the ω-3FA period was also significantly lower than in the control period (5 patients vs. 14 patients, P = 0.011). There was a significant difference in modified Rankin Scale scores at 90 days after onset of SAH between the groups (P = 0.031). No adverse events were associated with ω-3FA administration. Administration of ω-3FA after aneurysmal SAH may reduce the frequency of cerebral vasospasm and may improve clinical outcomes. Copyright © 2016 Elsevier Inc. All rights reserved.

  10. Fatty Acid Oxidation Disorders

    MedlinePlus

    ... other health conditions > Fatty acid oxidation disorders Fatty acid oxidation disorders E-mail to a friend Please ... these disorders, go to genetests.org . What fatty acid oxidation disorders are tested for in newborn screening? ...

  11. Meconium fatty acid ethyl esters as biomarkers of late gestational ethanol exposure and indicator of ethanol-induced multi-organ injury in fetal sheep.

    PubMed

    Zelner, Irene; Kenna, Kelly; Brien, James F; Bocking, Alan; Harding, Richard; Walker, David; Koren, Gideon

    2013-01-01

    Meconium fatty acid ethyl esters (FAEE) constitute a biomarker of heavy fetal ethanol exposure. Our objective was to measure meconium FAEE in fetal sheep following daily, relatively moderate-dose ethanol exposure in late gestation, and to evaluate their utility in identifying fetal organ-system injury. Pregnant ewes received ethanol (0.75 g/kg; n = 14) or saline (n = 8) via 1-h i.v. infusion daily during the third trimester equivalent, while additional pregnant sheep served as untreated controls (n = 6). The daily ethanol regimen produced similar maximal maternal and fetal plasma ethanol concentrations of 0.11-0.12 g/dL. Ewes and fetuses were euthanized shortly before term, and meconium was collected and analyzed for FAEE (ethyl palmitate, stearate, linoleate, and oleate). Meconium total FAEE concentration was significantly higher in ethanol-exposed fetuses compared with controls, and a positive cut-off of 0.0285 nmol total FAEE/g meconium had 93.3% sensitivity and specificity for detecting fetal ethanol exposure. When the studied animals (ethanol-exposed and controls) were classified according to meconium FAEE concentration, FAEE-positive and FAEE-negative groups frequently differed with respect to previously examined pathological endpoints, including nephron endowment, lung collagen deposition, cardiomyocyte maturation, and tropoelastin gene expression in cerebral vessels. Furthermore, in all studied animals as a group (ethanol-exposed and controls combined), meconium FAEE concentration was correlated with many of these pathological endpoints in fetal organs. We conclude that, in fetal sheep, meconium FAEE could serve as a biomarker of daily ethanol exposure in late gestation and could identify fetuses with subtle ethanol-induced toxic effects in various organs. This study illustrates the potential for using meconium FAEE to identify neonates at risk for dysfunction of major organs following in-utero ethanol exposure that does not result in overt

  12. Fetal exposure to alcohol as evidenced by fatty acid ethyl esters in meconium in the absence of maternal drinking history in pregnancy.

    PubMed

    Chan, Daphne; Klein, Julia; Karaskov, Tatyana; Koren, Gideon

    2004-10-01

    The detection of fatty acid ethyl esters (FAEE) in neonatal meconium has been proposed as a novel screening method for intrauterine exposure to alcohol. We investigated the potential use of meconium FAEE screening in a high-risk neonatal population in the absence of maternal drinking history. One hundred forty-two meconium samples of neonates suspected of intrauterine illicit substance exposure and referred to the Motherisk Laboratory were analyzed for the existence of drugs by enzyme-linked immunosorbent assay (ELISA) and FAEE by gas chromatography-flame ionization detection (GC-FID). A positive FAEE test was previously defined as a cumulative measurement of 7 individual FAEE > or = 2 nmol/g. Seventy-one percent of the samples tested positive for at least 1 illicit drug, with cannabis being the most prevalent (52.3%). Fourteen percent of all samples tested positive for prenatal alcohol exposure, as evidenced by cumulative meconium FAEE > or = 2 nmol/g. Ethyl oleate, linoleate, palmitate, and arachidonate were detected most often and at the highest levels. At least 3 individual FAEE were detected in 95% of all positive samples, and none could be identified by the use of 1 selected FAEE. Significantly elevated levels of FAEE above the baseline and the presence of multiple FAEE species in meconium are exclusive to neonates who have likely been exposed to excessive amounts of alcohol in utero. Babies born to mothers who are suspected to use illicit drugs in pregnancy are at elevated risk for exposure also to alcohol in utero. Meconium FAEE are emerging biologic markers that can potentially facilitate earlier diagnosis and intervention for less apparent forms of alcohol-related disabilities that cannot be confirmed in the absence of maternal drinking history.

  13. Meconium Fatty Acid Ethyl Esters as Biomarkers of Late Gestational Ethanol Exposure and Indicator of Ethanol-Induced Multi-Organ Injury in Fetal Sheep

    PubMed Central

    Zelner, Irene; Kenna, Kelly; Brien, James F.; Bocking, Alan; Harding, Richard; Walker, David; Koren, Gideon

    2013-01-01

    Background Meconium fatty acid ethyl esters (FAEE) constitute a biomarker of heavy fetal ethanol exposure. Our objective was to measure meconium FAEE in fetal sheep following daily, relatively moderate-dose ethanol exposure in late gestation, and to evaluate their utility in identifying fetal organ-system injury. Methods Pregnant ewes received ethanol (0.75 g/kg; n = 14) or saline (n = 8) via 1-h IV infusion daily during the third trimester equivalent, while additional pregnant sheep served as untreated controls (n = 6). The daily ethanol regimen produced similar maximal maternal and fetal plasma ethanol concentrations of 0.11–0.12 g/dL. Ewes and fetuses were euthanized shortly before term, and meconium was collected and analyzed for FAEE (ethyl palmitate, stearate, linoleate, and oleate). Results Meconium total FAEE concentration was significantly higher in ethanol-exposed fetuses compared with controls, and a positive cut-off of 0.0285 nmol total FAEE/g meconium had 93.3% sensitivity and specificity for detecting fetal ethanol exposure. When the studied animals (ethanol-exposed and controls) were classified according to meconium FAEE concentration, FAEE-positive and FAEE-negative groups frequently differed with respect to previously examined pathological endpoints, including nephron endowment, lung collagen deposition, cardiomyocyte maturation, and tropoelastin gene expression in cerebral vessels. Furthermore, in all studied animals as a group (ethanol-exposed and controls combined), meconium FAEE concentration was correlated with many of these pathological endpoints in fetal organs. Conclusions We conclude that, in fetal sheep, meconium FAEE could serve as a biomarker of daily ethanol exposure in late gestation and could identify fetuses with subtle ethanol-induced toxic effects in various organs. This study illustrates the potential for using meconium FAEE to identify neonates at risk for dysfunction of major organs following in-utero ethanol

  14. Production of Omega-3 Fatty Acid Ethyl Esters from Menhaden Oil Using Proteus vulgaris Lipase-Mediated One-Step Transesterification and Urea Complexation.

    PubMed

    Kim, Soo-Jin; Kim, Hyung Kwoun

    2016-05-01

    An organic solvent-stable lipase from Proteus vulgaris K80 was used to produce the omega-3 polyunsaturated fatty acid ethyl esters (ω-3 PUFA EEs). First, the lyophilized recombinant lipase K80 (LyoK80) was used to perform the transesterification reaction of menhaden oil and ethanol. LyoK80 produced the ω-3 PUFA EEs with a conversion yield of 82 % in the presence of 20 % water content via a three-step ethanol-feeding process; however, in a non-aqueous condition, LyoK80 produced only a slight amount of the ω-3 PUFA EEs. To enhance its reaction properties, the lipase K80 was immobilized on a hydrophobic bead to derive ImmK80; the biochemical properties and substrate specificity of ImmK80 are similar to those of LyoK80. ImmK80 was then used to produce ω-3 PUFA EEs in accordance with the same transesterification reaction. Unlike LyoK80, ImmK80 achieved a high ω-3 PUFA EE conversion yield of 86 % under a non-aqueous system via a one-step ethanol-feeding reaction. The ω-3 PUFA EEs were purified up to 92 % using a urea complexation method.

  15. Dose-response and time-response analysis of total fatty acid ethyl esters in meconium as a biomarker of prenatal alcohol exposure.

    PubMed

    Kwak, Ho-Seok; Han, Jung-Yeol; Choi, June-Seek; Ahn, Hyun-Kyong; Kwak, Dong-Wook; Lee, Yeon-Kyung; Koh, Sun-Young; Jeong, Go-Un; Velázquez-Armenta, E Yadira; Nava-Ocampo, Alejandro A

    2014-09-01

    Little is known on how the dose and timing of exposure co-influence the cumulative concentration of fatty acid ethyl esters (FAEEs) in meconium. The objective of the study was to assess the cumulative concentration of FAEEs in meconium as a biomarker of light, moderate, or heavy prenatal alcohol exposure occurring at either first, second, or third trimesters of pregnancy. History of prenatal alcohol exposure was obtained in the 34th week of gestation from 294 pregnant women. Meconium was collected from their babies within the first 6 to 12 h after birth and examined for the presence of nine FAEEs. No significant differences were identified between the cumulative levels of FAEEs in the meconium from the babies born to abstainers and those born to mothers with history of light-to-moderate prenatal alcohol exposure during their pregnancy. Light-to-moderate prenatal alcohol exposure cannot be reliably predicted by the cumulative FAEE concentrations in meconium of exposed babies. A cumulative FAEE level of >10 nmol/g would be required to consider that prenatal alcohol exposure during the second to third trimesters occurred at risky levels in the absence of reliable maternal history of ethanol exposure. © 2014 John Wiley & Sons, Ltd.

  16. Fatty acid ethyl esters (FAEEs) as markers for alcohol in meconium: method validation and implementation of a screening program for prenatal drug exposure.

    PubMed

    Hastedt, Martin; Krumbiegel, Franziska; Gapert, René; Tsokos, Michael; Hartwig, Sven

    2013-09-01

    Alcohol consumption during pregnancy is a widespread problem and can cause severe fetal damage. As the diagnosis of fetal alcohol syndrome is difficult, the implementation of a reliable marker for alcohol consumption during pregnancy into meconium drug screening programs would be invaluable. A previously published gas chromatography mass spectrometry method for the detection of fatty acid ethyl esters (FAEEs) as alcohol markers in meconium was optimized and newly validated for a sample size of 50 mg. This method was applied to 122 cases from a drug-using population. The meconium samples were also tested for common drugs of abuse. In 73 % of the cases, one or more drugs were found. Twenty percent of the samples tested positive for FAEEs at levels indicating significant alcohol exposure. Consequently, alcohol was found to be the third most frequently abused substance within the study group. This re-validated method provides an increase in testing sensitivity, is reliable and easily applicable as part of a drug screening program. It can be used as a non-invasive tool to detect high alcohol consumption in the last trimester of pregnancy. The introduction of FAEEs testing in meconium screening was found to be of particular use in a drug-using population.

  17. Linear Versus Non-Linear Dose-Response Relationship Between Prenatal Alcohol Exposure and Meconium Concentration of Nine Different Fatty Acid Ethyl Esters

    PubMed Central

    Yang, J.Y.; Kwak, H.S.; Choi, J.S.; Ahn, H.K.; Oh, Y.J.; Velázquez-Armenta, E.Y.; Nava-Ocampo, A.A.

    2015-01-01

    Presence of individual fatty acid ethyl esters (FAEEs) in meconium is considered to be a reliable biomarker of prenatal alcohol exposure, and their concentration has been found to be linearly associated with poor postnatal development, supporting the widely extended idea that ethanol is a non-threshold teratogen. However, a growing number of epidemiological studies have consistently found a lack of adverse short- and long-term fetal outcomes at low exposure levels. We therefore aimed to investigate the relationship between the concentration of individual FAEEs and prenatal alcohol exposure in meconium samples collected within the first 6 to 12?h after birth from 182 babies born to abstainer mothers and from 54 babies born to women who self-reported either light or moderate alcohol ingestion in the second or third trimester of pregnancy. In most cases, the individual FAEE concentrations were negligible and not significantly different (P >0.05) between exposed and control babies. The concentrations appeared to increase linearly with the dose only in the few babies born to mothers who reported >3 drinks/week. These results provide evidence that the correlation between prenatal alcohol exposure and individual FAEE concentrations in meconium is non-linear shape, with a threshold probably at 3 drinks/week. PMID:26691866

  18. Improved production of fatty acid ethyl esters in Saccharomyces cerevisiae through up-regulation of the ethanol degradation pathway and expression of the heterologous phosphoketolase pathway.

    PubMed

    de Jong, Bouke Wim; Shi, Shuobo; Siewers, Verena; Nielsen, Jens

    2014-03-12

    Due to an increasing demand of transportation fuels, a lower availability of cheap crude oil and a lack of sustainability of fossil fuels, a gradual shift from petroleum based fuels towards alternative and renewable fuel resources will be required in the near future. Fatty acid ethyl esters (FAEEs) have properties similar to current crude diesel and could therefore form an important contribution to the development of sustainable transportation fuels in future. It is important to develop novel cell factories for efficient production of FAEEs and their precursors. Here, a Saccharomyces cerevisiae cell factory expressing a heterologous wax ester synthase (ws2) from Marinobacter hydrocarbonoclasticus was used to produce FAEEs from ethanol and acyl-coenzyme A (acyl-CoA). The production of acyl-CoA requires large amounts of NADPH and acetyl-CoA. Therefore, two metabolic engineering strategies for improved provision of NADPH and acetyl-CoA were evaluated. First, the ethanol degradation pathway was employed to re-channel carbon flow towards the synthesis of acetyl-CoA. Therefore, ADH2 and ALD6 encoding, respectively, alcohol dehydrogenase and acetaldehyde dehydrogenase were overexpressed together with the heterologous gene acsSEL641P encoding acetyl-CoA synthetase. The co-overexpression of ADH2, ALD6 and acsSEL641P with ws2 resulted in 408 ± 270 μg FAEE gCDW-1, a 3-fold improvement. Secondly, for the expression of the PHK pathway two genes, xpkA and ack, both descending from Aspergillus nidulans, were co-expressed together with ws2 to catalyze, respectively, the conversion of xylulose-5-phosphate to acetyl phosphate and glyceraldehyde-3-phosphate and acetyl phosphate to acetate. Alternatively, ack was substituted with pta from Bacillus subtilis, encoding phosphotransacetylase for the conversion of acetyl phosphate to acetyl-CoA. Both PHK pathways were additionally expressed in a strain with multiple chromosomally integrated ws2 gene, which resulted in respectively

  19. Improved production of fatty acid ethyl esters in Saccharomyces cerevisiae through up-regulation of the ethanol degradation pathway and expression of the heterologous phosphoketolase pathway

    PubMed Central

    2014-01-01

    Background Due to an increasing demand of transportation fuels, a lower availability of cheap crude oil and a lack of sustainability of fossil fuels, a gradual shift from petroleum based fuels towards alternative and renewable fuel resources will be required in the near future. Fatty acid ethyl esters (FAEEs) have properties similar to current crude diesel and could therefore form an important contribution to the development of sustainable transportation fuels in future. It is important to develop novel cell factories for efficient production of FAEEs and their precursors. Results Here, a Saccharomyces cerevisiae cell factory expressing a heterologous wax ester synthase (ws2) from Marinobacter hydrocarbonoclasticus was used to produce FAEEs from ethanol and acyl-coenzyme A (acyl-CoA). The production of acyl-CoA requires large amounts of NADPH and acetyl-CoA. Therefore, two metabolic engineering strategies for improved provision of NADPH and acetyl-CoA were evaluated. First, the ethanol degradation pathway was employed to re-channel carbon flow towards the synthesis of acetyl-CoA. Therefore, ADH2 and ALD6 encoding, respectively, alcohol dehydrogenase and acetaldehyde dehydrogenase were overexpressed together with the heterologous gene acsSEL641P encoding acetyl-CoA synthetase. The co-overexpression of ADH2, ALD6 and acsSEL641P with ws2 resulted in 408 ± 270 μg FAEE gCDW−1, a 3-fold improvement. Secondly, for the expression of the PHK pathway two genes, xpkA and ack, both descending from Aspergillus nidulans, were co-expressed together with ws2 to catalyze, respectively, the conversion of xylulose-5-phosphate to acetyl phosphate and glyceraldehyde-3-phosphate and acetyl phosphate to acetate. Alternatively, ack was substituted with pta from Bacillus subtilis, encoding phosphotransacetylase for the conversion of acetyl phosphate to acetyl-CoA. Both PHK pathways were additionally expressed in a strain with multiple chromosomally integrated ws2 gene, which

  20. Plant fatty acid hydroxylases

    DOEpatents

    Somerville, Chris; Broun, Pierre; van de Loo, Frank

    2001-01-01

    This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants. In addition, the use of genes encoding fatty acid hydroxylases or desaturases to alter the level of lipid fatty acid unsaturation in transgenic plants is described.

  1. Omega-6 Fatty Acids

    MedlinePlus

    ... types of fats. Some types are found in vegetable oils, including corn, evening primrose seed, safflower, and soybean ... from studying specific omega-6 fatty acids or plant oils containing omega-6 fatty acids. See the separate ...

  2. Fatty acid analogs

    DOEpatents

    Elmaleh, David R.; Livni, Eli

    1985-01-01

    In one aspect, a radioactively labeled analog of a fatty acid which is capable of being taken up by mammalian tissue and which exhibits an in vivo beta-oxidation rate below that with a corresponding radioactively labeled fatty acid.

  3. Omega-3 fatty acids

    PubMed Central

    Schwalfenberg, Gerry

    2006-01-01

    OBJECTIVE To examine evidence for the role of omega-3 fatty acids in cardiovascular disease. QUALITY OF EVIDENCE PubMed was searched for articles on the role of omega-3 fatty acids in cardiovascular disease. Level I and II evidence indicates that omega-3 fatty acids are beneficial in improving cardiovascular outcomes. MAIN MESSAGE Dietary intake of omega-3 fatty acids has declined by 80% during the last 100 years, while intake of omega-6 fatty acids has greatly increased. Omega-3 fatty acids are cardioprotective mainly due to beneficial effects on arrhythmias, atherosclerosis, inflammation, and thrombosis. There is also evidence that they improve endothelial function, lower blood pressure, and significantly lower triglycerides. CONCLUSION There is good evidence in the literature that increasing intake of omega-3 fatty acids improves cardiac outcomes. Physicians need to integrate dietary recommendations for consumption of omega-3 fatty acids into their usual cardiovascular care. PMID:16812965

  4. Fatty acid ethyl esters in hair as alcohol markers: estimating a reliable cut-off point by evaluation of 1,057 autopsy cases.

    PubMed

    Hastedt, Martin; Bossers, Lydia; Krumbiegel, Franziska; Herre, Sieglinde; Hartwig, Sven

    2013-06-01

    Alcohol abuse is a widespread problem, especially in Western countries. Therefore, it is important to have markers of alcohol consumption with validated cut-off points. For many years research has focused on analysis of hair for alcohol markers, but data on the performance and reliability of cut-off values are still lacking. Evaluating 1,057 cases from 2005 to 2011, included a large sample group for the estimation of an applicable cut-off value when compared to earlier studies on fatty acid ethyl esters (FAEEs) in hair. The FAEEs concentrations in hair, police investigation reports, medical history, and the macroscopic and microscopic alcohol-typical results from autopsy, such as liver, pancreas, and cardiac findings, were taken into account in this study. In 80.2 % of all 1,057 cases pathologic findings that may be related to alcohol abuse were reported. The cases were divided into social drinkers (n = 168), alcohol abusers (n = 502), and cases without information on alcohol use. The median FAEEs concentration in the group of social drinkers was 0.302 ng/mg (range 0.008-14.3 ng/mg). In the group of alcohol abusers a median of 1.346 ng/mg (range 0.010-83.7 ng/mg) was found. Before June 2009 the hair FAEEs test was routinely applied to a proximal hair segment of 0-6 cm, changing to a routinely investigated hair length of 3 cm after 2009, as proposed by the Society of Hair Testing (SoHT). The method showed significant differences between the groups of social drinkers and alcoholics, leading to an improvement in the postmortem detection of alcohol abuse. Nevertheless, the performance of the method was rather poor, with an area under the curve calculated from receiver operating characteristic (ROC curve AUC) of 0.745. The optimum cut-off value for differentiation between social and chronic excessive drinking calculated for hair FAEEs was 1.08 ng/mg, with a sensitivity of 56 % and a specificity of 80 %. In relation to the "Consensus on Alcohol Markers 2012

  5. New Bioactive Fatty Acids

    USDA-ARS?s Scientific Manuscript database

    Many oxygenated fatty acids are bioactive compounds. Nocardia cholesterolicum and Flavobacterium DS5 convert oleic acid to 10 hydroxy stearic acid and linoleic acid to 10-hydroxy-12(Z)-octadecanoic acid. Pseudomonas aeruginosa PR3 converts oleic acid to new compounds, 7,10-dihydroxy-8(E)-octadecen...

  6. New bioactive fatty acids

    USDA-ARS?s Scientific Manuscript database

    Many oxygenated fatty acids are bioactive compounds. Nocardia cholesterolicum and Flavobacterium DS5 convert oleic acid to 10 hydroxy stearic acid and linoleic acid to 10-hydroxy-12(Z)-octadecanoic acid. Pseudomonas aeruginosa PR3 converts oleic acid to the new compounds, 7,10-dihydroxy-8(E)-octad...

  7. Omega-3 Fatty Acids

    MedlinePlus

    Omega-3 fatty acids are used together with lifestyle changes (diet, weight-loss, exercise) to reduce the amount of triglycerides (a fat-like ... people with very high triglycerides. Omega-3 fatty acids are in a class of medications called antilipemic ...

  8. History of fatty acids

    USDA-ARS?s Scientific Manuscript database

    Fatty acids are basic renewable chemical building blocks that can be used as intermediates for a multitude of products. Today the global value of fatty acids exceeds 18 billion dollars and is expected to increase to nearly 26 billion over the period from 2014-2019. From it auspicious beginnings, the...

  9. Mutant fatty acid desaturase

    DOEpatents

    Shanklin, John; Cahoon, Edgar B.

    2004-02-03

    The present invention relates to a method for producing mutants of a fatty acid desaturase having a substantially increased activity towards fatty acid substrates with chains containing fewer than 18 carbons relative to an unmutagenized precursor desaturase having an 18 carbon atom chain length substrate specificity. The method involves inducing one or more mutations in the nucleic acid sequence encoding the precursor desaturase, transforming the mutated sequence into an unsaturated fatty acid auxotroph cell such as MH13 E. coli, culturing the cells in the absence of supplemental unsaturated fatty acids, thereby selecting for recipient cells which have received and which express a mutant fatty acid desaturase with an elevated specificity for fatty acid substrates having chain lengths of less than 18 carbon atoms. A variety of mutants having 16 or fewer carbon atom chain length substrate specificities are produced by this method. Mutant desaturases produced by this method can be introduced via expression vectors into prokaryotic and eukaryotic cells and can also be used in the production of transgenic plants which may be used to produce specific fatty acid products.

  10. Trans Fatty Acids

    NASA Astrophysics Data System (ADS)

    Doyle, Ellin

    1997-09-01

    Fats and their various fatty acid components seem to be a perennial concern of nutritionists and persons concerned with healthful diets. Advice on the consumption of saturated, polyunsaturated, monounsaturated, and total fat bombards us from magazines and newspapers. One of the newer players in this field is the group of trans fatty acids found predominantly in partially hydrogenated fats such as margarines and cooking fats. The controversy concerning dietary trans fatty acids was recently addressed in an American Heart Association (AHA) science advisory (1) and in a position paper from the American Society of Clinical Nutrition/American Institute of Nutrition (ASCN/AIN) (2). Both reports emphasize that the best preventive strategy for reducing risk for cardiovascular disease and some types of cancer is a reduction in total and saturated fats in the diet, but a reduction in the intake of trans fatty acids was also recommended. Although the actual health effects of trans fatty acids remain uncertain, experimental evidence indicates that consumption of trans fatty acids adversely affects serum lipid levels. Since elevated levels of serum cholesterol and triacylglycerols are associated with increased risk of cardiovascular disease, it follows that intake of trans fatty acids should be minimized.

  11. Comparison of different solid-phase-extraction cartridges for a fatty acid cleanup of the ethyl acetate/cyclohexane based multi-pesticide residue method EN 12393.

    PubMed

    Steinbach, Philipp; Schwack, Wolfgang

    2014-01-03

    SPE cartridges of different anion exchange materials and florisil were compared regarding their efficiency to remove free fatty acids from ethylacetate/cyclohexane (1:1) extracts, their elution profiles and recovery rates for 38 representative pesticides, their contribution to an elevated background during gas chromatography-mass spectrometry (GC-MS), and on possible matrix effects caused by the cartridge material itself. From the seven tested cartridges, only Varian PSA (PSA) and Silicycle SiliaPrep Diamine (SPD) were very well able to retain fatty acids from ethylacetate/cyclohexane solutions and provided satisfying recoveries and elution profiles for the tested pesticides. Thus, with both cartridges a fast and simple cleanup was developed and tested with 86 pesticides as well as with EN 12393 GPC extracts of oat flour. The SPE cleanup clearly improved the identification of pesticides and reduced false negative findings due to retention time shifts and superimpositions of quantifier and/or qualifier ions. As compared with dispersive SPE it was shown, that depending on the amount of sorbent the cleanup efficiency was comparable, but recoveries were generally better for cartridge SPE procedures.

  12. Wipe-test and patch-test for alcohol misuse based on the concentration ratio of fatty acid ethyl esters and squalene CFAEE/CSQ in skin surface lipids.

    PubMed

    Pragst, F; Auwärter, V; Kiessling, B; Dyes, C

    2004-07-16

    Fatty acid ethyl esters (FAEE) are known to be formed in blood and almost all human tissues after alcohol consumption and to be incorporated from sebum into hair where they can be used as long-term markers for excessive alcohol consumption. In order to examine whether skin surface lipids which consist mainly of sebum are an equally useful matrix for measurement of FAEE as alcohol abuse markers, samples were collected by a wipe-test from the forehead of 13 teetotallers, 16 social drinkers, 10 death cases with known recent alcohol misuse and five death cases without indications of alcohol misuse. The samples were analysed by headspace solid-phase microextraction and gas chromatography-mass spectrometry for ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate and by high performance liquid chromatography with photodiode array detector for squalene, (SQ), as a natural reference substance which the FAEE concentrations were related to. The ratio mFAEE/mSQ ranged between 0.16 and 1.12 ng/microg (mean 0.34 ng/microg) for the teetotallers and between 0.08 and 0.94 ng/microg (mean 0.37 ng/microg) for the social drinkers with no significant difference between both groups. For the alcoholics 2.4-24.2 ng/microg (mean 13.1 ng/microg) were found. For two volunteers the course of mFAEE/mSQ 2 weeks before and 3 weeks after a single high alcohol dose was pursued by daily wipe tests. A strong increase of mFAEE/mSQ occurred between 7 and 12 days after the drinking event. This delay can be explained by the transition time of about 8 days between sebum production and its appearance on the skin surface known from literature. For seven social drinkers skin surface lipid samples were also collected using drug of abuse patches of the firm PharmCheck. The ratios mFAEE/mSQ in these samples were in the same range as from the wipe-test. The comparison with the self-reported ethanol amounts consumed the week before and during the test gave no good correlation (R2 = 0.42). It can be

  13. Discovery of essential fatty acids

    PubMed Central

    Spector, Arthur A.; Kim, Hee-Yong

    2015-01-01

    Dietary fat was recognized as a good source of energy and fat-soluble vitamins by the first part of the 20th century, but fatty acids were not considered to be essential nutrients because they could be synthesized from dietary carbohydrate. This well-established view was challenged in 1929 by George and Mildred Burr who reported that dietary fatty acid was required to prevent a deficiency disease that occurred in rats fed a fat-free diet. They concluded that fatty acids were essential nutrients and showed that linoleic acid prevented the disease and is an essential fatty acid. The Burrs surmised that other unsaturated fatty acids were essential and subsequently demonstrated that linolenic acid, the omega-3 fatty acid analog of linoleic acid, is also an essential fatty acid. The discovery of essential fatty acids was a paradigm-changing finding, and it is now considered to be one of the landmark discoveries in lipid research. PMID:25339684

  14. Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings

    SciTech Connect

    Uranga, Carla C.; Beld, Joris; Mrse, Anthony; Córdova-Guerrero, Iván; Burkart, Michael D.; Hernández-Martínez, Rufina

    2016-04-01

    The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. - Highlights: • Lasiodiplodia theobromae produces a wide variety of fatty acid esters in natural substrates. • Ethyl stearate and ethyl linoleate inhibit tobacco germination at 0.2 mg/mL. • Ethyl stearate and ethyl linoleate induce tobacco germination at 98 ng/mL. • Tobacco growth increase in ethyl stearate and ethyl linoleate parallels gibberellic acid. • A role as plant growth regulators is proposed for fatty acid esters.

  15. [Omega-3 fatty acids].

    PubMed

    Huyghebaert, C

    2007-01-01

    Omega-3 fatty acids have been drawing the interest of researchers for quite a number of years. The study of the impact of fish consumption on health and particularly on a cardiovascular level is the subject of much research. Some encouraging results have led to the study of omega-3 fatty acids in various other diseases. The interest in 'omega-3' has been widely relayed by the media and a huge market has developed with several allegations in its favour. This article is an attempt to shed light on these health claims, based on currently available scientific data.

  16. Omega-3 fatty acids (image)

    MedlinePlus

    Omega-3 fatty acids are a form of polyunsaturated fat that the body derives from food. Omega-3s (and omega-6s) are known as essential fatty acids (EFAs) because they are important for good health. ...

  17. Influence of iron solubility and charged surface-active compounds on lipid oxidation in fatty acid ethyl esters containing association colloids.

    PubMed

    Homma, Rika; Johnson, David R; McClements, D Julian; Decker, Eric A

    2016-05-15

    The impact of iron compounds with different solubilities on lipid oxidation was studied in the presence and absence of association colloids. Iron (III) sulfate only accelerated lipid oxidation in the presence of association colloids while iron (III) oleate accelerated oxidation in the presence and absence of association colloids. Further, iron (III) oxide retarded lipid oxidation both with and without association colloids. The impact of charged association colloids on lipid oxidation in ethyl oleate was also investigated. Association colloids consisting of the anionic surface-active compound dodecyl sulphosuccinate sodium salt (AOT), cationic surface-active compound hexadecyltrimethylammonium bromide (CTAB), and nonionic surface-active compound 4-(1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol (Triton X-100) retarded, promoted, and had no effect on lipid oxidation rates, respectively. These results indicate that the polarity of metal compounds and the charge of association colloids play a big role in lipid oxidation. Copyright © 2015 Elsevier Ltd. All rights reserved.

  18. (Radioiodinated free fatty acids)

    SciTech Connect

    Knapp, Jr., F. F.

    1987-12-11

    The traveler participated in the Second International Workshop on Radioiodinated Free Fatty Acids in Amsterdam, The Netherlands where he presented an invited paper describing the pioneering work at the Oak Ridge National Laboratory (ORNL) involving the design, development and testing of new radioiodinated methyl-branched fatty acids for evaluation of heart disease. He also chaired a technical session on the testing of new agents in various in vitro and in vivo systems. He also visited the Institute for Clinical and Experimental Nuclear Medicine in Bonn, West Germany, to review, discuss, plan and coordinate collaborative investigations with that institution. In addition, he visited the Cyclotron Research Center in Liege, Belgium, to discuss continuing collaborative studies with the Osmium-191/Iridium-191m radionuclide generator system, and to complete manuscripts and plan future studies.

  19. Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings.

    PubMed

    Uranga, Carla C; Beld, Joris; Mrse, Anthony; Córdova-Guerrero, Iván; Burkart, Michael D; Hernández-Martínez, Rufina

    2016-04-01

    The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. Copyright © 2016 Elsevier Inc. All rights reserved.

  20. Effect of ω-3 fatty acid ethyl esters on apolipoprotein B-48 kinetics in obese subjects on a weight-loss diet: a new tracer kinetic study in the postprandial state.

    PubMed

    Wong, Annette T Y; Chan, Dick C; Barrett, P Hugh R; Adams, Leon A; Watts, Gerald F

    2014-08-01

    Dysregulated chylomicron metabolism may account for hypertriglyceridemia and increased risk of cardiovascular disease in obese subjects. Supplementation with ω-3 fatty acid ethyl ester (FAEE) decreases plasma triglyceride. However, its effect on postprandial chylomicron metabolism in obese subjects on a weight-loss diet has not yet been investigated. We aimed to examine the effect of ω-3 FAEE supplementation on apolipoprotein (apo) B-48 kinetics in obese subjects on a weight-loss diet. We carried out a 12-week, randomized trial of a hypocaloric diet plus 4 g/d ω-3 FAEE supplementation (46% eicosapentaenoic acid and 38% docosahexaenoic acid) (n = 13) compared with a hypocaloric diet alone (n = 12) on postprandial apoB-48 kinetics in obese subjects after ingestion of an oral load. The apoB-48 kinetics were determined using stable isotope tracer kinetics and multicompartmental modeling. We evaluated plasma total and incremental apoB-48 0- to 10-hour area under the curves (AUCs) as well as apoB-48 secretion and fractional catabolic rate. Weight loss with or without ω-3 FAEE supplementation significantly reduced body weight, total fat mass, homeostasis model assessment score, fasting triglyceride concentration, postprandial triglyceride AUC, and increased plasma high-density lipoprotein cholesterol concentration (P < .05 in all). Compared with weight loss alone, weight loss plus ω-3 FAEE significantly (all P < .05) decreased fasting triglyceride (-11%), apoB-48 (-36%) concentrations, postprandial triglyceride (-21%), and apoB-48 (-22%) total AUCs, as well as incremental postprandial triglyceride AUCs (-32%). The ω-3 FAEE also significantly decreased apoB-48 secretion in the basal state, without a significant effect during the postprandial period (3-6 hours). The fractional catabolic rate of apoB-48 increased with both interventions with no significant independent effect of ω-3 FAEE supplementation. Addition of ω-3 FAEE supplementation to a moderate weight

  1. Fatty acid-producing hosts

    DOEpatents

    Pfleger, Brian F; Lennen, Rebecca M

    2013-12-31

    Described are hosts for overproducing a fatty acid product such as a fatty acid. The hosts include an exogenous nucleic acid encoding a thioesterase and, optionally, an exogenous nucleic acid encoding an acetyl-CoA carboxylase, wherein an acyl-CoA synthetase in the hosts are functionally delected. The hosts prefereably include the nucleic acid encoding the thioesterase at an intermediate copy number. The hosts are preferably recominantly stable and growth-competent at 37.degree. C. Methods of producing a fatty acid product comprising culturing such hosts at 37.degree. C. are also described.

  2. Detection of fatty acid ethyl esters in skin surface lipids as biomarkers of ethanol consumption in alcoholics, social drinkers, light drinkers, and teetotalers using a methodology based on microwave-assisted extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry.

    PubMed

    González-Illán, Fernando; Ojeda-Torres, Geovannie; Díaz-Vázquez, Liz M; Rosario, Osvaldo

    2011-05-01

    Fatty acid ethyl esters (FAEE) are known to be a direct alcohol marker and are mainly investigated in hair samples for their ability to be incorporated into this matrix from sebum. The present study used an already developed methodology to provide and confirm information about the use of FAEEs in skin surface lipids as markers of alcohol consumption. The skin surface lipids were collected with Sebutapes(®) from the foreheads of teetotalers, light drinkers, social drinkers, and alcoholics. The samples were analyzed by direct solid-phase microextraction and gas chromatography-mass spectrometry for ethyl myristate, ethyl palmitate, ethyl oleate, and ethyl stearate. Relative FAEE/sebum allowed an evaluation of alcohol consumption. The ranges obtained for relative FAEEs in each category were as follows, teetotalers (0-13.85 pg/mg), light drinkers (11.10-26.80 pg/mg), social drinkers (20.55-86.55 pg/mg), and alcoholics (109.00-1243.40 pg/mg). A social drinker volunteer was monitored during a period of two months. The highest m(FAEE)/m(sebum) were generally detected 7-9 days after the days of high alcohol consumption. From these results, a clear distinction of teetotalers, social drinkers, and alcoholics could be established with the methodology used.

  3. High yielding synthesis of N-ethyl dehydroamino acids.

    PubMed

    Monteiro, Luís S; Suárez, Ana S

    2012-10-01

    Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain N-ethyl-α, β-dehydroamino acid derivatives. The application of this N-alkylation procedure to several methyl esters of β,β-dibromo and β-bromo, β-substituted dehydroamino acids protected with standard amine protecting groups was subsequently reported. The corresponding N-ethyl, β-bromo dehydroamino acid derivatives were obtained in fair to high yields and some were used as substrates in Suzuki cross-coupling reactions to give N-ethyl, β,β-disubstituted dehydroalanine derivatives. Herein, we further explore N-ethylation of β-halo dehydroamino acid derivatives using triethyloxonium tetrafluoroborate as alkylating agent, but substituting N,N-diisopropylethylamine for potassium tert-butoxide as auxiliary base. In these conditions, for all β-halo dehydroamino acid derivatives, reactions were complete and the N-ethylated derivative could be isolated in high yield. This method was also applied for N-ethylation of non-halogenated dehydroamino acids. Again, with all compounds the reactions were complete and the N-ethyl dehydroamino acid derivatives could be isolated in high yields. Some of these N-ethyl dehydroamino acid methyl ester derivatives were converted in high yields to their corresponding acids and coupled to an amino acid methyl ester to give N-ethyl dehydrodipeptide derivatives in good yields. Thus, this method constitutes a general procedure for high yielding synthesis of N-ethylated dehydroamino acids, which can be further applied in peptide synthesis.

  4. 40 CFR 721.10244 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, 2-[bis(2- chloroethoxy)phosphinyl]ethyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphonic acid, P- ethyl]-, 2- ethyl... New Uses for Specific Chemical Substances § 721.10244 Phosphonic acid, P- ethyl]-, 2- ethyl 2... substance identified as phosphonic acid, P- ethyl]-, 2- ethyl 2-chloroethyl ester (PMN P-09-195; CAS No...

  5. 40 CFR 721.10244 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, 2-[bis(2- chloroethoxy)phosphinyl]ethyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphonic acid, P- ethyl]-, 2- ethyl... New Uses for Specific Chemical Substances § 721.10244 Phosphonic acid, P- ethyl]-, 2- ethyl 2... substance identified as phosphonic acid, P- ethyl]-, 2- ethyl 2-chloroethyl ester (PMN P-09-195; CAS No...

  6. 40 CFR 721.10244 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, 2-[bis(2- chloroethoxy)phosphinyl]ethyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phosphonic acid, P- ethyl]-, 2- ethyl... New Uses for Specific Chemical Substances § 721.10244 Phosphonic acid, P- ethyl]-, 2- ethyl 2... substance identified as phosphonic acid, P- ethyl]-, 2- ethyl 2-chloroethyl ester (PMN P-09-195; CAS No...

  7. Treatment of Fatty Acid Oxidation Disorders

    MedlinePlus

    ... of fatty acid oxidation disorders Treatment of fatty acid oxidation disorders E-mail to a friend Please ... page It's been added to your dashboard . Fatty acid oxidation disorders are rare health conditions that affect ...

  8. Overview of Omega-3 Fatty Acid Therapies

    PubMed Central

    Bradberry, J. Chris; Hilleman, Daniel E.

    2013-01-01

    The triglyceride (TG)-lowering benefits of the very-long-chain omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are well documented. Available as prescription formulations and dietary supplements, EPA and DHA are recommended by the American Heart Association for patients with coronary heart disease and hypertriglyceridemia. Dietary supplements are not subject to the same government regulatory standards for safety, efficacy, and purity as prescription drugs are; moreover, supplements may contain variable concentrations of EPA and DHA and possibly other contaminants. Reducing low-density lipoprotein-cholesterol (LDL-C) levels remains the primary treatment goal in the management of dyslipidemia. Dietary supplements and prescription formulations that contain both EPA and DHA may lower TG levels, but they may also increase LDL-C levels. Two prescription formulations of long-chain omega-3 fatty acids are available in the U.S. Although prescription omega-3 acid ethyl esters (OM-3-A EEs, Lovaza) contain high-purity EPA and DHA, prescription icosapent ethyl (IPE, Vascepa) is a high-purity EPA agent. In clinical trials of statin-treated and non–statin-treated patients with hypertriglyceridemia, both OM-3-A EE and IPE lowered TG levels and other atherogenic markers; however, IPE did not increase LDL-C levels. Results of recent outcomes trials of long-chain omega-3 fatty acids, fibrates, and niacin have been disappointing, failing to show additional reductions in adverse cardiovascular events when combined with statins. Therefore, the REDUCE–IT study is being conducted to evaluate the effect of the combination of IPE and statins on cardiovascular outcomes in high-risk patients. The results of this trial are eagerly anticipated. PMID:24391388

  9. Gas chromatographic analysis of infant formulas for total fatty acids, including trans fatty acids.

    PubMed

    Satchithanandam, Subramaniam; Fritsche, Jan; Rader, Jeanne I

    2002-01-01

    Twelve powdered and 13 liquid infant formulas were analyzed by using an extension of AOAC Official Method 996.01 for fat analysis in cereal products. Samples were hydrolyzed with 8 N HCl and extracted with ethyl and petroleum ethers. Fatty acid methyl esters were prepared by refluxing the mixed ether extracts with methanolic sodium hydroxide in the presence of 14% boron trifluoride in methanol. The extracts were analyzed by gas chromatography. In powdered formulas, saturated fatty acid (SFA) content (mean +/- SD; n = 12) was 41.05 +/- 3.94%, monounsaturated fatty acid (MUFA) content was 36.97 +/- 3.38%, polyunsaturated fatty acid (PUFA) content was 20.07 +/- 3.08%, and total trans fatty acid content was 1.30 +/- 1.27%. In liquid formulas, SFA content (mean +/- SD; n = 13) was 42.29 +/- 2.98%, MUFA content was 36.05 +/- 2.47%, PUFA content was 20.65 +/- 2.40%, and total trans fatty acid content was 0.88 +/- 0.54%. Total fat content in powdered formulas ranged from 4.4 to 5.5 g/100 kcal and linoleic acid content ranged from 868 to 1166 mg/100 kcal. In liquid formulas, total fat content ranged from 4.1 to 5.1 g/100 kcal and linoleic acid content ranged from 820 to 1100 mg/100 kcal. There were no significant differences between powdered and liquid infant formulas in concentrations of total fat, SFA, MUFA, PUFA, or trans fatty acids.

  10. Fatty Acid Desaturases, Polyunsaturated Fatty Acid Regulation, and Biotechnological Advances

    PubMed Central

    Lee, Je Min; Lee, Hyungjae; Kang, SeokBeom; Park, Woo Jung

    2016-01-01

    Polyunsaturated fatty acids (PUFAs) are considered to be critical nutrients to regulate human health and development, and numerous fatty acid desaturases play key roles in synthesizing PUFAs. Given the lack of delta-12 and -15 desaturases and the low levels of conversion to PUFAs, humans must consume some omega-3 and omega-6 fatty acids in their diet. Many studies on fatty acid desaturases as well as PUFAs have shown that fatty acid desaturase genes are closely related to different human physiological conditions. Since the first front-end desaturases from cyanobacteria were cloned, numerous desaturase genes have been identified and animals and plants have been genetically engineered to produce PUFAs such as eicosapentaenoic acid and docosahexaenoic acid. Recently, a biotechnological approach has been used to develop clinical treatments for human physiological conditions, including cancers and neurogenetic disorders. Thus, understanding the functions and regulation of PUFAs associated with human health and development by using biotechnology may facilitate the engineering of more advanced PUFA production and provide new insights into the complexity of fatty acid metabolism. PMID:26742061

  11. Role of bioactive fatty acids in nonalcoholic fatty liver disease.

    PubMed

    Juárez-Hernández, Eva; Chávez-Tapia, Norberto C; Uribe, Misael; Barbero-Becerra, Varenka J

    2016-08-02

    Nonalcoholic fatty liver disease (NAFLD) is characterized by fat deposition in hepatocytes, and a strong association with nutritional factors. Dietary fatty acids are classified according to their biochemical properties, which confer their bioactive roles. Monounsaturated fatty acids have a dual role in various human and murine models. In contrast, polyunsaturated fatty acids exhibit antiobesity, anti steatosic and anti-inflammatory effects. The combination of these forms of fatty acids-according to dietary type, daily intake and the proportion of n-6 to n-3 fats-can compromise hepatic lipid metabolism. A chemosensory rather than a nutritional role makes bioactive fatty acids possible biomarkers for NAFLD. Bioactive fatty acids provide health benefits through modification of fatty acid composition and modulating the activity of liver cells during liver fibrosis. More and better evidence is necessary to elucidate the role of bioactive fatty acids in nutritional and clinical treatment strategies for patients with NAFLD.

  12. Fatty acids and lymphocyte functions.

    PubMed

    Calder, P C; Yaqoob, P; Thies, F; Wallace, F A; Miles, E A

    2002-01-01

    The immune system acts to protect the host against pathogenic invaders. However, components of the immune system can become dysregulated such that their activities are directed against host tissues, so causing damage. Lymphocytes are involved in both the beneficial and detrimental effects of the immune system. Both the level of fat and the types of fatty acid present in the diet can affect lymphocyte functions. The fatty acid composition of lymphocytes, and other immune cells, is altered according to the fatty acid composition of the diet and this alters the capacity of those cells to produce eicosanoids, such as prostaglandin E2, which are involved in immunoregulation. A high fat diet can impair lymphocyte function. Cell culture and animal feeding studies indicate that oleic, linoleic, conjugated linoleic, gamma-linolenic, dihomo-gamma-linolenic, arachidonic, alpha-linolenic, eicosapentaenoic and docosahexaenoic acids can all influence lymphocyte proliferation, the production of cytokines by lymphocytes, and natural killer cell activity. High intakes of some of these fatty acids are necessary to induce these effects. Among these fatty acids the long chain n-3 fatty acids, especially eicosapentaenoic acid, appear to be the most potent when included in the human diet. Although not all studies agree, it appears that fish oil, which contains eicosapentaenoic acid, down regulates the T-helper 1-type response which is associated with chronic inflammatory disease. There is evidence for beneficial effects of fish oil in such diseases; this evidence is strongest for rheumatoid arthritis. Since n-3 fatty acids also antagonise the production of inflammatory eicosanoid mediators from arachidonic acid, there is potential for benefit in asthma and related diseases. Recent evidence indicates that fish oil may be of benefit in some asthmatics but not others.

  13. Abiotic synthesis of fatty acids

    NASA Technical Reports Server (NTRS)

    Leach, W. W.; Nooner, D. W.; Oro, J.

    1978-01-01

    The formation of fatty acids by Fischer-Tropsch-type synthesis was investigated with ferric oxide, ammonium carbonate, potassium carbonate, powdered Pueblito de Allende carbonaceous chondrite, and filings from the Canyon Diablo meteorite used as catalysts. Products were separated and identified by gas chromatography and mass spectrometry. Iron oxide, Pueblito de Allende chondrite, and Canyon Diablo filings in an oxidized catalyst form yielded no fatty acids. Canyon Diablo filings heated overnight at 500 C while undergoing slow purging by deuterium produced fatty acids only when potassium carbonate was admixed; potassium carbonate alone also produced these compounds. The active catalytic combinations gave relatively high yields of aliphatic and aromatic hydrocarbons; substantial amounts of n-alkenes were almost invariably observed when fatty acids were produced; the latter were in the range C6 to C18, with maximum yield in C9 or 10.

  14. Abiotic synthesis of fatty acids

    NASA Technical Reports Server (NTRS)

    Leach, W. W.; Nooner, D. W.; Oro, J.

    1978-01-01

    The formation of fatty acids by Fischer-Tropsch-type synthesis was investigated with ferric oxide, ammonium carbonate, potassium carbonate, powdered Pueblito de Allende carbonaceous chondrite, and filings from the Canyon Diablo meteorite used as catalysts. Products were separated and identified by gas chromatography and mass spectrometry. Iron oxide, Pueblito de Allende chondrite, and Canyon Diablo filings in an oxidized catalyst form yielded no fatty acids. Canyon Diablo filings heated overnight at 500 C while undergoing slow purging by deuterium produced fatty acids only when potassium carbonate was admixed; potassium carbonate alone also produced these compounds. The active catalytic combinations gave relatively high yields of aliphatic and aromatic hydrocarbons; substantial amounts of n-alkenes were almost invariably observed when fatty acids were produced; the latter were in the range C6 to C18, with maximum yield in C9 or 10.

  15. Metabolic engineering of yeast to produce fatty acid-derived biofuels: bottlenecks and solutions

    PubMed Central

    Sheng, Jiayuan; Feng, Xueyang

    2015-01-01

    Fatty acid-derived biofuels can be a better solution than bioethanol to replace petroleum fuel, since they have similar energy content and combustion properties as current transportation fuels. The environmentally friendly microbial fermentation process has been used to synthesize advanced biofuels from renewable feedstock. Due to their robustness as well as the high tolerance to fermentation inhibitors and phage contamination, yeast strains such as Saccharomyces cerevisiae and Yarrowia lipolytica have attracted tremendous attention in recent studies regarding the production of fatty acid-derived biofuels, including fatty acids, fatty acid ethyl esters, fatty alcohols, and fatty alkanes. However, the native yeast strains cannot produce fatty acids and fatty acid-derived biofuels in large quantities. To this end, we have summarized recent publications in this review on metabolic engineering of yeast strains to improve the production of fatty acid-derived biofuels, identified the bottlenecks that limit the productivity of biofuels, and categorized the appropriate approaches to overcome these obstacles. PMID:26106371

  16. The enrichment of n-3 polyunsaturated fatty acids using aminopropyl solid phase extraction columns.

    PubMed

    Wilson, R; James Henderson, R; Burkow, I C; Sargent, J R

    1993-01-01

    A rapid, simple and reliable method is described for the preparation of concentrates of methyl or ethyl esters of n-3 polyunsaturated fatty acids by solid phase extraction using aminopropyl bonded silica columns. After applying mixtures of fatty acid esters in hexane, saturated and monounsaturated fatty acid esters are preferentially eluted with hexane whereas polyunsaturated fatty acids (PUFA) can subsequently be eluted with dichloromethane. Concentrates containing 80-90% n-3 PUFA can thus be obtained using fish oil fatty acids esters as a starting material.

  17. Changes in Esters of Fatty Acids of Rhizopus arrhizus During Germination and Growth

    PubMed Central

    Hess, S. L.; Weber, D. J.; Gunasekaran, M.

    1972-01-01

    Natural esters of fatty acids of Rhizopus arrhizus Fischer increased during the first 48 hr of growth. During the 48- to 72-hr period, there was a shift in concentration from the methyl esters to the ethyl esters of fatty acids. PMID:5079078

  18. A comprehensive evaluation of the density of neat fatty acids and esters

    USDA-ARS?s Scientific Manuscript database

    Density is one of the most important physical properties of a chemical compound, affecting numerous applications. An application in the case of fatty acid esters (biodiesel) is that density is specified in some biodiesel standards. In the present work, the density of fatty acid methyl, ethyl, propyl...

  19. Analysis of mixtures of fatty acids and fatty alcohols in fermentation broth.

    PubMed

    Liu, Yilan; Chen, Ting; Yang, Maohua; Wang, Caixia; Huo, Weiyan; Yan, Daojiang; Chen, Jinjin; Zhou, Jiemin; Xing, Jianmin

    2014-01-03

    Microbial production of fatty acids and fatty alcohols has attracted increasing concerns because of energy crisis and environmental impact of fossil fuels. Therefore, simple and efficient methods for the extraction and quantification of these compounds become necessary. In this study, a high-performance liquid chromatography-refractive index detection (HPLC-RID) method was developed for the simultaneous quantification of fatty acids and fatty alcohols in these samples. The optimum chromatographic conditions are C18 column eluted with methanol:water:acetic acid (90:9.9:0.1, v/v/v); column temperature, 26°C; flow rate, 1.0mL/min. Calibration curves of all selected analytes showed good linearity (r(2)≥0.9989). The intra-day and inter-day relative standard deviations (RSDs) of the 10 compounds were less than 4.46% and 5.38%, respectively, which indicated that the method had good repeatability and precision. Besides, a method for simultaneous extraction of fatty acids and fatty alcohols from fermentation broth was optimized by orthogonal design. The optimal extraction conditions were as follows: solvent, ethyl acetate; solvent to sample ratio, 0.5:1; rotation speed, 2min at 260rpm; extraction temperature, 10°C. This study provides simple and fast methods to simultaneously extract and quantify fatty acids and fatty alcohols for the first time. It will be useful for the study of microbial production of these products. Copyright © 2013 Elsevier B.V. All rights reserved.

  20. Kinetics of Ethyl Acetate Synthesis Catalyzed by Acidic Resins

    ERIC Educational Resources Information Center

    Antunes, Bruno M.; Cardoso, Simao P.; Silva, Carlos M.; Portugal, Ines

    2011-01-01

    A low-cost experiment to carry out the second-order reversible reaction of acetic acid esterification with ethanol to produce ethyl acetate is presented to illustrate concepts of kinetics and reactor modeling. The reaction is performed in a batch reactor, and the acetic acid concentration is measured by acid-base titration versus time. The…

  1. Kinetics of Ethyl Acetate Synthesis Catalyzed by Acidic Resins

    ERIC Educational Resources Information Center

    Antunes, Bruno M.; Cardoso, Simao P.; Silva, Carlos M.; Portugal, Ines

    2011-01-01

    A low-cost experiment to carry out the second-order reversible reaction of acetic acid esterification with ethanol to produce ethyl acetate is presented to illustrate concepts of kinetics and reactor modeling. The reaction is performed in a batch reactor, and the acetic acid concentration is measured by acid-base titration versus time. The…

  2. Fatty acid biosynthesis in actinomycetes

    PubMed Central

    Gago, Gabriela; Diacovich, Lautaro; Arabolaza, Ana; Tsai, Shiou-Chuan; Gramajo, Hugo

    2011-01-01

    All organisms that produce fatty acids do so via a repeated cycle of reactions. In mammals and other animals, these reactions are catalyzed by a type I fatty acid synthase (FAS), a large multifunctional protein to which the growing chain is covalently attached. In contrast, most bacteria (and plants) contain a type II system in which each reaction is catalyzed by a discrete protein. The pathway of fatty acid biosynthesis in Escherichia coli is well established and has provided a foundation for elucidating the type II FAS pathways in other bacteria (White et al., 2005). However, fatty acid biosynthesis is more diverse in the phylum Actinobacteria: Mycobacterium, possess both FAS systems while Streptomyces species have only the multi-enzyme FAS II system and Corynebacterium species exclusively FAS I. In this review we present an overview of the genome organization, biochemical properties and physiological relevance of the two FAS systems in the three genera of actinomycetes mentioned above. We also address in detail the biochemical and structural properties of the acyl-CoA carboxylases (ACCases) that catalyzes the first committed step of fatty acid synthesis in actinomycetes, and discuss the molecular bases of their substrate specificity and the structure-based identification of new ACCase inhibitors with anti-mycobacterial properties. PMID:21204864

  3. Polyunsaturated Fatty Acids in Children

    PubMed Central

    2013-01-01

    Polyunsaturated fatty acids (PUFAs) are the major components of brain and retina, and are the essential fatty acids with important physiologically active functions. Thus, PUFAs should be provided to children, and are very important in the brain growth and development for fetuses, newborn infants, and children. Omega-3 fatty acids decrease coronary artery disease and improve blood flow. PUFAs have been known to have anti-inflammatory action and improved the chronic inflammation such as auto-immune diseases or degenerative neurologic diseases. PUFAs are used for metabolic syndrome related with obesity or diabetes. However, there are several considerations related with intake of PUFAs. Obsession with the intake of unsaturated fatty acids could bring about the shortage of essential fatty acids that are crucial for our body, weaken the immune system, and increase the risk of heart disease, arrhythmia, and stroke. In this review, we discuss types, physiologic mechanism of action of PUFAs, intake of PUFAs for children, recommended intake of PUFAs, and considerations for the intake of PUFAs. PMID:24224148

  4. 21 CFR 172.860 - Fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Fatty acids. 172.860 Section 172.860 Food and Drugs... Multipurpose Additives § 172.860 Fatty acids. The food additive fatty acids may be safely used in food and in... food additive consists of one or any mixture of the following straight-chain monobasic carboxylic acids...

  5. 21 CFR 172.860 - Fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Fatty acids. 172.860 Section 172.860 Food and... Multipurpose Additives § 172.860 Fatty acids. The food additive fatty acids may be safely used in food and in... food additive consists of one or any mixture of the following straight-chain monobasic carboxylic acids...

  6. 21 CFR 172.860 - Fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Fatty acids. 172.860 Section 172.860 Food and... Multipurpose Additives § 172.860 Fatty acids. The food additive fatty acids may be safely used in food and in... food additive consists of one or any mixture of the following straight-chain monobasic carboxylic acids...

  7. 21 CFR 172.860 - Fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Fatty acids. 172.860 Section 172.860 Food and... Multipurpose Additives § 172.860 Fatty acids. The food additive fatty acids may be safely used in food and in... food additive consists of one or any mixture of the following straight-chain monobasic carboxylic acids...

  8. Conjugated Fatty Acid Synthesis

    PubMed Central

    Rawat, Richa; Yu, Xiao-Hong; Sweet, Marie; Shanklin, John

    2012-01-01

    Conjugated linolenic acids (CLNs), 18:3 Δ9,11,13, lack the methylene groups found between the double bonds of linolenic acid (18:3 Δ9,12,15). CLNs are produced by conjugase enzymes that are homologs of the oleate desaturases FAD2. The goal of this study was to map the domain(s) within the Momordica charantia conjugase (FADX) responsible for CLN formation. To achieve this, a series of Momordica FADX-Arabidopsis FAD2 chimeras were expressed in the Arabidopsis fad3fae1 mutant, and the transformed seeds were analyzed for the accumulation of CLN. These experiments identified helix 2 and the first histidine box as a determinant of conjugase product partitioning into punicic acid (18:3 Δ9cis,11trans,13cis) or α-eleostearic acid (18:3 Δ9cis,11trans,13trans). This was confirmed by analysis of a FADX mutant containing six substitutions in which the sequence of helix 2 and first histidine box was converted to that of FAD2. Each of the six FAD2 substitutions was individually converted back to the FADX equivalent identifying residues 111 and 115, adjacent to the first histidine box, as key determinants of conjugase product partitioning. Additionally, expression of FADX G111V and FADX G111V/D115E resulted in an approximate doubling of eleostearic acid accumulation to 20.4% and 21.2%, respectively, compared with 9.9% upon expression of the native Momordica FADX. Like the Momordica conjugase, FADX G111V and FADX D115E produced predominantly α-eleostearic acid and little punicic acid, but the FADX G111V/D115E double mutant produced approximately equal amounts of α-eleostearic acid and its isomer, punicic acid, implicating an interactive effect of residues 111 and 115 in punicic acid formation. PMID:22451660

  9. 40 CFR 721.10109 - Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane. 721.10109 Section 721.10109 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10109 Hexanoic acid, 2-ethyl-, mixed...

  10. 40 CFR 721.10109 - Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane. 721.10109 Section 721.10109 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10109 Hexanoic acid, 2-ethyl-, mixed...

  11. 40 CFR 721.10109 - Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane. 721.10109 Section 721.10109 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10109 Hexanoic acid, 2-ethyl-, mixed...

  12. 40 CFR 721.10109 - Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Hexanoic acid, 2-ethyl-, mixed triesters with benzoic acid and trimethylolpropane. 721.10109 Section 721.10109 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10109 Hexanoic acid, 2-ethyl-, mixed...

  13. Omega-3 Fatty Acids during Pregnancy

    MedlinePlus

    OMEGA-3 FATTY ACIDS DURING PREGNANCY S HARE W ITH W OMEN OMEGA-3 FATTY ACIDS DURING PREGNANCY During pregnancy, your baby gets most ... eat and vitamins you take. Omega-3 fatty acids (omega-3s) are an important family of building ...

  14. Investigation of fatty acid esters to replace isopropyl myristate in the sterility test for ophthalmic ointments.

    PubMed

    Cardoso, Valéria Macedo; Solano, Ana Gabriela Reis; Prado, Maria Auxiliadora Fontes; Nunan, Elzíria de Aguiar

    2006-11-16

    Several pharmacopoeias recommend the membrane filtration method for the sterility test of ophthalmic ointments. Isopropyl myristate, a fatty acid ester that exhibits high toxicity mainly against Gram-negative microorganisms, is indicated as a solvent for ointments. In this study, six fatty acid esters (diethyl adipate, diisopropyl adipate, ethyl laurate, ethyl myristate, methyl caprylate and isopropyl palmitate) were evaluated as solvents to replace isopropyl myristate in the sterility test for ophthalmic ointments. The logarithm of the partition coefficient (logP) of the fatty acid esters was calculated from the sum of the substituent hydrophobicity constants (pi) of the functional groups present in their molecules. The ability of the solvents to dissolve an ophthalmic ointment base was investigated. The D-value method was used to assess the antimicrobial activity of isopropyl palmitate, ethyl myristate, ethyl laurate and isopropyl myristate against Pseudomonas aeruginosa. Isopropyl palmitate was the least toxic solvent to this microorganism, since it had the highest D-value (171.1 min). No significant difference was observed between the D-values of ethyl myristate (89.4 min) and isopropyl myristate (92.5 min). Ethyl laurate exhibited the lowest D-value (27.2 min). Using gas chromatography coupled to mass spectrometry, other fatty acid esters were detected as the predominant impurities in the solvents, as well as acid contaminants in low or insignificant amounts.

  15. Plant fatty acid hydroxylase

    DOEpatents

    Somerville, Chris; van de Loo, Frank

    2000-01-01

    The present invention relates to the identification of nucleic acid sequences and constructs, and methods related thereto, and the use of these sequences and constructs to produce genetically modified plants for the purpose of altering the composition of plant oils, waxes and related compounds.

  16. Omacor (prescription omega-3-acid ethyl esters 90): From severe rhythm disorders to hypertriglyceridemia.

    PubMed

    Rupp, Heinz

    2009-07-01

    Despite progress made in post-myocardial infarction (MI) revascularization and background therapy for the failing heart, the prevention of adverse cardiac remodeling associated with severe rhythm disorders remains an important drug target. Part of the remodeling can be counteracted by modulating the activity of ion channels and exchangers by omega-3 acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). In the GISSI-Prevenzione and GISSI-HF trials, omega-3 fatty acids were administered as ethyl esters (Omacor Solvay Pharmaceuticals) and not as triglycerides present in fish oil. Ethyl esters result in a sustained intestinal absorption of EPA and DHA and require various purification steps during production, thereby minimizing the content of environmental toxins. Also the rather high (38%) DHA content of Omacor should not be ignored since in rats with low dose intake of omega-3 acids, DHA but not EPA inhibited ischemia-induced arrhythmias. In patients on multiple tablets, 840 mg EPA+DHA in one capsule is preferred to increase compliance. It is not justified to refer to Omacor as "n-3 polyunsaturated fatty acid supplementation" or even "fish oil" and, based on controlled clinical trials, there is no evidence that fish oil could be a substitute of Omacor. To avoid further confusion, guidelines should be precise and refer to the medication, eg, as in NICE guideline CG48: "Omega-3-acid ethyl esters treatment licensed for secondary prevention post-MI." The anti-arrhythmogenic action of Omacor should be seen in the context of implantable cardioverter-defibrillator trials (DINAMIT, IRIS) where non-sudden death was increased and total mortality unaltered. However, Omacor administered in the GISSI-HF trial reduced the incidence of severe arrhythmic events and mortality. Also in the GISSI-Prevenzione trial, arrhythmic death and mortality were reduced. At higher dosages (daily, 3-4 g) Omacor exhibits more pronounced cardiovascular benefits and, as a licensed

  17. Nitrated fatty acids: Synthesis and measurement

    PubMed Central

    Woodcock, Steven R.; Bonacci, Gustavo; Gelhaus, Stacy L.; Schopfer, Francisco J.

    2012-01-01

    Nitrated fatty acids are the product of nitrogen dioxide reaction with unsaturated fatty acids. The discovery of peroxynitrite and peroxidase-induced nitration of biomolecules led to the initial reports of endogenous nitrated fatty acids. These species increase during ischemia reperfusion, but concentrations are often at or near the limits of detection. Here, we describe multiple methods for nitrated fatty acid synthesis, sample extraction from complex biological matrices, and a rigorous method of qualitative and quantitative detection of nitrated fatty acids by LC-MS. In addition, optimized instrument conditions and caveats regarding data interpretation are discussed. PMID:23200809

  18. Nitrated fatty acids: synthesis and measurement.

    PubMed

    Woodcock, Steven R; Bonacci, Gustavo; Gelhaus, Stacy L; Schopfer, Francisco J

    2013-06-01

    Nitrated fatty acids are the product of nitrogen dioxide reaction with unsaturated fatty acids. The discovery of peroxynitrite and peroxidase-induced nitration of biomolecules led to the initial reports of endogenous nitrated fatty acids. These species increase during ischemia/reperfusion, but concentrations are often at or near the limits of detection. Here, we describe multiple methods for nitrated fatty acid synthesis and sample extraction from complex biological matrices and a rigorous method of qualitative and quantitative detection of nitrated fatty acids by liquid chromatography-mass spectrometry. In addition, optimized instrument conditions and caveats regarding data interpretation are discussed.

  19. New radiohalogenated alkenyl tellurium fatty acids

    SciTech Connect

    Srivastava, P.C.; Knapp, F.F. Jr.; Kabalka, G.W.

    1987-01-01

    Radiolabeled long-chain fatty acids have diagnostic value as radiopharmaceutical tools in myocardial imaging. Some applications of these fatty acids are limited due to their natural metabolic degradation in vivo with subsequent washout of the radioactivity from the myocardium. The identification of structural features that will increase the myocardial residence time without decreasing the heart uptake of long-chain fatty acids is of interest. Fatty acids containing the tellurium heteroatom were the first modified fatty acids developed that show unique prolonged myocardial retention and low blood levels. Our detailed studies with radioiodinated vinyliodide substituted tellurium fatty acids demonstrate that heart uptake is a function of the tellurium position. New techniques of tellurium and organoborane chemistry have been developed for the synthesis of a variety of radioiodinated iodoalkenyl tellurium fatty acids. 9 refs., 3 figs., 2 tabs.

  20. Essential fatty acid requirement of juvenile red drum (Sciaenops ocellatus).

    PubMed

    Lochmann, R T; Gatlin, D M

    1993-10-01

    Feeding experiments and laboratory analyses were conducted to establish the essential fatty acid (EFA) requirement of red drum (Sciaenops ocellatus). Juvenile red drum were maintained in aquaria containing brackish water (5 ± 2‰ total dissolved solids) for two 6-week experiments. Semipurified diets contained a total of 70% lipid consisting of different combinations of tristearin [predominantly 18:0] and the following fatty acid ethyl esters: oleate, linoleate, linolenate, and a mixture of highly unsaturated fatty acids (HUFA) containing approximately 60% eicosapentaenoate plus docosahexaenoate. EFA-deficient diets (containing only tristearin or oleate) rapidly reduced fish growth and feed efficiency, and increased mortality. Fin erosion and a "shock syndrome" also occurred in association with EFA deficiency. Of the diets containing fatty acid ethyl esters, those with 0.5-1% (n-3) HUFA (0.3-0.6% eicosapentaenoate plus docosahexaenoate) promoted the best growth, survival, and feed efficiency; however, the control diet containing 7% menhaden fish oil provided the best performance. Excess (n-3) HUFA suppressed fish weight gain; suppression became evident at 1.5% (n-3) HUFA, and was pronounced at 2.5%. Fatty acid compositions of whole-body, muscle and liver tissues from red drum fed the various diets generally reflected dietary fatty acids, but modifications of these patterns also were evident. Levels of saturated fatty acids appeared to be regulated independent of diet. In fish fed EFA-deficient diets (containing only tristearin or oleate), monoenes increased and (n-3) HUFA were preferentially conserved in polar lipid fractions. Eicosatrienoic acid [20:3(n-9)] was not elevated in EFA-deficient red drum, apparently due to their limited ability to transform fatty acids. Red drum exhibited some limited ability to elongate and desaturate linoleic acid [18:2(n-6)] and linolenic acid [18:3(n-3)]; however, metabolism of 18:3(n-3) did not generally result in increased

  1. Fatty acid uptake in normal human myocardium

    SciTech Connect

    Vyska, K.; Meyer, W.; Stremmel, W.; Notohamiprodjo, G.; Minami, K.; Machulla, H.J.; Gleichmann, U.; Meyer, H.; Koerfer, R. )

    1991-09-01

    Fatty acid binding protein has been found in rat aortic endothelial cell membrane. It has been identified to be a 40-kDa protein that corresponds to a 40-kDa fatty acid binding protein with high affinity for a variety of long chain fatty acids isolated from rat heart myocytes. It is proposed that this endothelial membrane fatty acid binding protein might mediate the myocardial uptake of fatty acids. For evaluation of this hypothesis in vivo, influx kinetics of tracer-labeled fatty acids was examined in 15 normal subjects by scintigraphic techniques. Variation of the plasma fatty acid concentration and plasma perfusion rate has been achieved by modulation of nutrition state and exercise conditions. The clinical results suggest that the myocardial fatty acid influx rate is saturable by increasing fatty acid plasma concentration as well as by increasing plasma flow. For analysis of these data, functional relations describing fatty acid transport from plasma into myocardial tissue in the presence and absence of an unstirred layer were developed. The fitting of these relations to experimental data indicate that the free fatty acid influx into myocardial tissue reveals the criteria of a reaction on a capillary surface in the vicinity of flowing plasma but not of a reaction in extravascular space or in an unstirred layer and that the fatty acid influx into normal myocardium is a saturable process that is characterized by the quantity corresponding to the Michaelis-Menten constant, Km, and the maximal velocity, Vmax, 0.24 {plus minus} 0.024 mumol/g and 0.37 {plus minus} 0.013 mumol/g(g.min), respectively. These data are compatible with a nondiffusional uptake process mediated by the initial interaction of fatty acids with the 40-kDa membrane fatty acid binding protein of cardiac endothelial cells.

  2. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false 2-Propenoic acid, 2- ethyl ester. 721... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2- ethyl ester (PMN P-04...

  3. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 2-Propenoic acid, 2- ethyl ester. 721... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2- ethyl ester (PMN P-04...

  4. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Propenoic acid, 2- ethyl ester. 721... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2- ethyl ester (PMN...

  5. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2-Propenoic acid, 2- ethyl ester. 721... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2- ethyl ester (PMN...

  6. Fatty acid composition of selected prosthecate bacteria.

    PubMed

    Carter, R N; Schmidt, J M

    1976-10-11

    The cellular fatty acid composition of 14 strains of Caulobacter speices and types, two species of Prosthecomicrobium, and two species of Asticcacaulis was determined by gas-liquid chromatography. In most of these bacteria, the major fatty acids were octadecenoic acid (C18:1), hexadecenoic acid (C16:1) and hexadecanoic acid (C16:0). Some cyclopropane and branched chain fatty acids were detected in addition to the straight chained acids. Hydroxytetradecanoic acid was an important component of P.enhydrum but significant amounts of hydroxy acids were not detected in other prosthecate bacteria examined.

  7. Uptake of Ethyl Alcohol Vapor in Sulfuric Acid Solutions

    NASA Astrophysics Data System (ADS)

    Leu, M.

    2002-12-01

    The uptake of ethyl alcohol vapor in liquid sulfuric acid has been investigated over the composition range of 40 - 80 wt % H2SO4 and between the temperatures of 193-273 K. Laboratory studies were performed using a flow-tube reactor coupled to an electron-impact ionization mass spectrometer for detection of ethanol and possible reaction products, ethyl hydrogen sulfate and diethyl sulfate. The uptake coefficients (gamma) have been measured and found to vary from 0.018 to 0.065, depending upon the acid composition and temperature. For example, at concentrated acids greater than 70 wt % and dilute solutions (<70 wt %) colder than 210 K, the gamma values are approaching ~ 0.06. Under other conditions, the gamma values are smaller. The adsorption and thermal desorption measurements have been used to distinguish the possible uptake mechanisms, either solubility or reactive uptake. The results suggest that reactive uptakes are greater than 50 % under all conditions. For dilute acids, we also determine the effective Henry's law constants (H*). We will compare the results with the uptake of gaseous methyl alcohol and acetone in H2SO4 determined previously in our laboratory. The potential implications to the budget of ethyl alcohol in the global troposphere will also be discussed.

  8. Aspirin increases mitochondrial fatty acid oxidation.

    PubMed

    Uppala, Radha; Dudiak, Brianne; Beck, Megan E; Bharathi, Sivakama S; Zhang, Yuxun; Stolz, Donna B; Goetzman, Eric S

    2017-01-08

    The metabolic effects of salicylates are poorly understood. This study investigated the effects of aspirin on fatty acid oxidation. Aspirin increased mitochondrial long-chain fatty acid oxidation, but inhibited peroxisomal fatty acid oxidation, in two different cell lines. Aspirin increased mitochondrial protein acetylation and was found to be a stronger acetylating agent in vitro than acetyl-CoA. However, aspirin-induced acetylation did not alter the activity of fatty acid oxidation proteins, and knocking out the mitochondrial deacetylase SIRT3 did not affect the induction of long-chain fatty acid oxidation by aspirin. Aspirin did not change oxidation of medium-chain fatty acids, which can freely traverse the mitochondrial membrane. Together, these data indicate that aspirin does not directly alter mitochondrial matrix fatty acid oxidation enzymes, but most likely exerts its effects at the level of long-chain fatty acid transport into mitochondria. The drive on mitochondrial fatty acid oxidation may be a compensatory response to altered mitochondrial morphology and inhibited electron transport chain function, both of which were observed after 24 h incubation of cells with aspirin. These studies provide insight into the pathophysiology of Reye Syndrome, which is known to be triggered by aspirin ingestion in patients with fatty acid oxidation disorders.

  9. Usefulness of Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester) in Women to Lower Triglyceride Levels (Results from the MARINE and ANCHOR Trials).

    PubMed

    Mosca, Lori; Ballantyne, Christie M; Bays, Harold E; Guyton, John R; Philip, Sephy; Doyle, Ralph T; Juliano, Rebecca A

    2017-02-01

    There are limited data on the efficacy and safety of triglyceride (TG)-lowering agents in women. We conducted subgroup analyses of the effects of icosapent ethyl (a high-purity prescription form of the ethyl ester of the omega-3 fatty acid, eicosapentaenoic acid) on TG levels (primary efficacy variable) and other atherogenic and inflammatory parameters in a total of 215 women with a broad range of TG levels (200-2000 mg/dl) enrolled in two 12-week placebo-controlled trials: MARINE (n = 18; placebo, n = 18) and ANCHOR (n = 91; placebo, n = 88). Icosapent ethyl 4 g/day significantly reduced TG levels from baseline to week 12 versus placebo in both MARINE (-22.7%; p = 0.0327) and ANCHOR (-21.5%; p <0.0001) without increasing low-density lipoprotein cholesterol levels. Significant improvements were also observed in non-high-density lipoprotein cholesterol levels in MARINE (-15.7%; p = 0.0082) and ANCHOR (-14.2%; p <0.0001) and total cholesterol levels in MARINE (-14.9%; p = 0.0023) and ANCHOR (-12.1%; p <0.0001), along with significant increases of >500% in eicosapentaenoic acid levels in plasma and red blood cells (all p <0.001). Icosapent ethyl was well tolerated, with adverse-event profiles comparable with findings in the overall studies. In conclusion, icosapent ethyl 4 g/day significantly reduced TG levels and other atherogenic parameters in women without increasing low-density lipoprotein cholesterol levels compared with placebo; the clinical implications of these findings are being evaluated in the REDUCtion of Cardiovascular Events With Eicosapentaenoic Acid [EPA]-Intervention Trial (REDUCE-IT) cardiovascular outcomes study.

  10. Fatty acid composition of frequently consumed foods in Turkey with special emphasis on trans fatty acids.

    PubMed

    Karabulut, Ihsan

    2007-12-01

    Fatty acid compositions of frequently consumed foods in Turkey were analyzed by capillary gas chromatography with particular emphasis on trans fatty acids. The survey was carried out on 134 samples that were categorized as meat products, chocolates, bakery products and others. The meat products except chicken-based foods have trans fatty acids, arising as a result of ruminant activity, with an average content of 1.45 g/100 g fatty acids. The conjugated linoleic acid content of meat and chicken doner kebabs were found higher than other meat products. Chocolate samples contained trans fatty acids less than 0.17 g/100 g fatty acids, with the exceptional national product of chocolate bars and hazelnut cocoa cream (2.03 and 3.68 g/100 g fatty acids, respectively). Bakery products have the highest trans fatty acid contents and ranged from 0.99 to 17.77 g/100 g fatty acids. The average trans fatty acid contents of infant formula and ice-cream, which are milk-based products, were 0.79 and 1.50 g/100 g fatty acids, respectively. Among the analyzed foods, it was found that coffee whitener and powdered whipped topping had the highest saturated fatty acid contents, with an average content of 98.71 g/100 g fatty acids.

  11. Omega-3 polyunsaturated fatty acids.

    PubMed

    Hull, Mark A

    2011-08-01

    Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are naturally occurring omega (ω)-3 long-chain polyunsaturated fatty acids (PUFAs), which are found in highest quantities in oily fish such as sardines and mackerel. Epidemiological studies of the association between fish intake, ω-3 PUFA intake or blood ω-3 PUFA levels and colorectal cancer (CRC) risk have not consistently suggested beneficial effects of ω-3 PUFAs on CRC (and other gastrointestinal cancer) risk. However, dietary administration of one or both of the main ω-3 PUFAs in rodent models of colorectal carcinogenesis has been demonstrated to reduce colorectal tumour size and multiplicity, compatible with CRC chemopreventative activity. EPA has now been demonstrated to reduce rectal polyp number and size in patients with familial adenomatous polyposis. A randomized polyp prevention trial of EPA is underway in order to test chemopreventative efficacy against 'sporadic' colorectal neoplasia. Copyright © 2011 Elsevier Ltd. All rights reserved.

  12. Omega-3 fatty acids and neuropsychiatric disorders.

    PubMed

    Young, Genevieve; Conquer, Julie

    2005-01-01

    Epidemiological evidence suggests that dietary consumption of the long chain omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), commonly found in fish or fish oil, may modify the risk for certain neuropsychiatric disorders. As evidence, decreased blood levels of omega-3 fatty acids have been associated with several neuropsychiatric conditions, including Attention Deficit (Hyperactivity) Disorder, Alzheimer's Disease, Schizophrenia and Depression. Supplementation studies, using individual or combination omega-3 fatty acids, suggest the possibility for decreased symptoms associated with some of these conditions. Thus far, however, the benefits of supplementation, in terms of decreasing disease risk and/or aiding in symptom management, are not clear and more research is needed. The reasons for blood fatty acid alterations in these disorders are not known, nor are the potential mechanisms by which omega-3 fatty acids may function in normal neuronal activity and neuropsychiatric disease prevention and/or treatment. It is clear, however, that DHA is the predominant n-3 fatty acid found in the brain and that EPA plays an important role as an anti-inflammatory precursor. Both DHA and EPA can be linked with many aspects of neural function, including neurotransmission, membrane fluidity, ion channel and enzyme regulation and gene expression. This review summarizes the knowledge in terms of dietary omega-3 fatty acid intake and metabolism, as well as evidence pointing to potential mechanisms of omega-3 fatty acids in normal brain functioning, development of neuropsychiatric disorders and efficacy of omega-3 fatty acid supplementation in terms of symptom management.

  13. Saturated Fatty Acid Requirer of Neurospora crassa

    PubMed Central

    Henry, Susan A.; Keith, Alec D.

    1971-01-01

    Dietary saturated fatty acids containing 12- to 18-carbon atoms satisfy growth requirements of Neurospora crassa mutant cel (previously named ol; Perkins et al., reference 11); unsaturated fatty acids are synthesized by direct desaturation when an appropriate saturate is available. Odd-chain saturates, 15 carbons and 17 carbons long, satisfy the requirement, and elaidic acid (18:1 Δ9trans) results in slow growth. Oleic acid and other cis-unsaturated fatty acids do not satisfy growth requirements; however, oleic acid plus elaidic acid result in growth at a faster rate than elaidate alone. The use of a spin-label fatty acid reveals that hyphae produced by cel during a slow basal level of growth have lipids that reflect a relatively rigid state of viscosity compared to wild type. cel Supplemented with fatty acids and wild type supplemented in the same way have lipids of the same viscosities as reflected by electron spin resonance. PMID:4323964

  14. Fatty acids of Pinus elliottii tissues.

    NASA Technical Reports Server (NTRS)

    Laseter, J. L.; Lawler, G. C.; Walkinshaw, C. H.; Weete, J. D.

    1973-01-01

    The total fatty constituents of slash pine (Pinus elliottii) tissue cultures, seeds, and seedlings were examined by GLC and MS. Qualitatively, the fatty acid composition of these tissues was found to be very similar to that reported for other pine species. The fatty acid contents of the tissue cultures resembled that of the seedling tissues. The branched-chain C(sub 17) acid reported for several other Pinus species was confirmed as the anteiso isomer.

  15. Fatty acids of Pinus elliottii tissues.

    NASA Technical Reports Server (NTRS)

    Laseter, J. L.; Lawler, G. C.; Walkinshaw, C. H.; Weete, J. D.

    1973-01-01

    The total fatty constituents of slash pine (Pinus elliottii) tissue cultures, seeds, and seedlings were examined by GLC and MS. Qualitatively, the fatty acid composition of these tissues was found to be very similar to that reported for other pine species. The fatty acid contents of the tissue cultures resembled that of the seedling tissues. The branched-chain C(sub 17) acid reported for several other Pinus species was confirmed as the anteiso isomer.

  16. Exogenous fatty acid metabolism in bacteria.

    PubMed

    Yao, Jiangwei; Rock, Charles O

    2017-10-01

    Bacterial type II fatty acid synthesis (FASII) is a target for novel antibiotic development. All bacteria encode for mechanisms to incorporate exogenous fatty acids, and some bacteria can use exogenous fatty acids to bypass FASII inhibition. Bacteria encode three different mechanisms for activating exogenous fatty acids for incorporation into phospholipid synthesis. Exogenous fatty acids are converted into acyl-CoA in Gammaproteobacteria such as E. coli. Acyl-CoA molecules constitute a separate pool from endogenously synthesized acyl-ACP. Acyl-CoA can be used for phospholipid synthesis or broken down by β-oxidation, but cannot be used for lipopolysaccharide synthesis. Exogenous fatty acids are converted into acyl-ACP in some Gram-negative bacteria. The resulting acyl-ACP undergoes the same fates as endogenously synthesized acyl-ACP. Exogenous fatty acids are converted into acyl-phosphates in Gram-positive bacteria, and can be used for phospholipid synthesis or become acyl-ACP. Only the order Lactobacillales can use exogenous fatty acids to bypass FASII inhibition. FASII shuts down completely in presence of exogenous fatty acids in Lactobacillales, allowing Lactobacillales to synthesize phospholipids entirely from exogenous fatty acids. Inhibition of FASII cannot be bypassed in other bacteria because FASII is only partially down-regulated in presence of exogenous fatty acid or FASII is required to synthesize essential metabolites such as β-hydroxyacyl-ACP. Certain selective pressures such as FASII inhibition or growth in biofilms can select for naturally occurring one step mutations that attenuate endogenous fatty acid synthesis. Although attempts have been made to estimate the natural prevalence of these mutants, culture-independent metagenomic methods would provide a better estimate. Copyright © 2017 Elsevier B.V. and Société Française de Biochimie et Biologie Moléculaire (SFBBM). All rights reserved.

  17. Fatty acid profile of kenaf seed oil

    USDA-ARS?s Scientific Manuscript database

    The fatty acid profile of kenaf (Hibiscus cannabinus L.) seed oil has been the subject of several previous reports in the literature. These reports vary considerably regarding the presence and amounts of specific fatty acids, notably epoxyoleic acid but also cyclic (cyclopropene and cyclopropane) fa...

  18. The linoleic acid and trans fatty acids of margarines.

    PubMed

    Beare-Rogers, J L; Gray, L M; Hollywood, R

    1979-09-01

    Fifty brands of margarine were analysed for cis-polyunsaturated acids by lipoxidase, for trans fatty acid by infared spectroscopy, and for fatty acid composition by gas-liquid chromatography. High concentrations of trans fatty acids tended to be associated with low concentrations of linoleic acid. Later analyses on eight of the brands, respresenting various proportions of linoleic to trans fatty acids, indicated that two of them contained still higher levels of trans fatty acids (greater than 60%) and negligible amounts of linoleic acid. It is proposed that margarine could be a vehicle for the distribution of some dietary linoleic acid and that the level of linoleic acid and the summation of the saturated plus trans fatty acids be known to ascertain nutritional characteristics.

  19. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...)-, ethyl ester. 721.7290 Section 721.7290 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to reporting...

  20. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...)-, ethyl ester. 721.7290 Section 721.7290 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to reporting...

  1. 40 CFR 721.10365 - Butanoic acid, 3-mercapto-2-methyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-, ethyl ester. 721.10365 Section 721.10365 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10365 Butanoic acid, 3-mercapto-2-methyl-, ethyl ester. (a) Chemical... acid, 3-mercapto-2-methyl-, ethyl ester (PMN P-10-56; CAS No. 888021-82-7) is subject to...

  2. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...)-, ethyl ester. 721.7290 Section 721.7290 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to...

  3. 40 CFR 721.10365 - Butanoic acid, 3-mercapto-2-methyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-, ethyl ester. 721.10365 Section 721.10365 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10365 Butanoic acid, 3-mercapto-2-methyl-, ethyl ester. (a) Chemical... acid, 3-mercapto-2-methyl-, ethyl ester (PMN P-10-56; CAS No. 888021-82-7) is subject to...

  4. 40 CFR 721.10365 - Butanoic acid, 3-mercapto-2-methyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-, ethyl ester. 721.10365 Section 721.10365 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10365 Butanoic acid, 3-mercapto-2-methyl-, ethyl ester. (a) Chemical... acid, 3-mercapto-2-methyl-, ethyl ester (PMN P-10-56; CAS No. 888021-82-7) is subject to...

  5. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...)-, ethyl ester. 721.7290 Section 721.7290 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to...

  6. Omega-3 Fatty Acid Formulations in Cardiovascular Disease: Dietary Supplements are Not Substitutes for Prescription Products.

    PubMed

    Fialkow, Jonathan

    2016-08-01

    Omega-3 fatty acid products are available as prescription formulations (icosapent ethyl, omega-3-acid ethyl esters, omega-3-acid ethyl esters A, omega-3-carboxylic acids) and dietary supplements (predominantly fish oils). Most dietary supplements and all but one prescription formulation contain mixtures of the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Products containing both EPA and DHA may raise low-density lipoprotein cholesterol (LDL-C). In clinical trials, the EPA-only prescription product, icosapent ethyl, did not raise LDL-C compared with placebo. To correct a common misconception, it is important to note that omega-3 fatty acid dietary supplements are not US FDA-approved over-the-counter drugs and are not required to demonstrate safety and efficacy prior to marketing. Conversely, prescription products are supported by extensive clinical safety and efficacy investigations required for FDA approval and have active and ongoing safety monitoring programs. While omega-3 fatty acid dietary supplements may have a place in the supplementation of diet, they generally contain lower levels of EPA and DHA than prescription products and are not approved or intended to treat disease. Perhaps due to the lack of regulation of dietary supplements, EPA and DHA levels may vary widely within and between brands, and products may also contain unwanted cholesterol or fats or potentially harmful components, including toxins and oxidized fatty acids. Accordingly, omega-3 fatty acid dietary supplements should not be substituted for prescription products. Similarly, prescription products containing DHA and EPA should not be substituted for the EPA-only prescription product, as DHA may raise LDL-C and thereby complicate the management of patients with dyslipidemia.

  7. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Sucrose fatty acid esters. 172.859 Section 172.859... CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified...) Sucrose fatty acid esters are the mono-, di-, and tri-esters of sucrose with fatty acids and are derived...

  8. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Sucrose fatty acid esters. 172.859 Section 172.859... CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified...) Sucrose fatty acid esters are the mono-, di-, and tri-esters of sucrose with fatty acids and are derived...

  9. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Sucrose fatty acid esters. 172.859 Section 172.859... CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified...) Sucrose fatty acid esters are the mono-, di-, and tri-esters of sucrose with fatty acids and are derived...

  10. 21 CFR 862.1290 - Fatty acids test system.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 8 2013-04-01 2013-04-01 false Fatty acids test system. 862.1290 Section 862.1290....1290 Fatty acids test system. (a) Identification. A fatty acids test system is a device intended to measure fatty acids in plasma and serum. Measurements of fatty acids are used in the diagnosis and...

  11. Antibacterial Targets in Fatty Acid Biosynthesis

    PubMed Central

    Wright, H. Tonie; Reynolds, Kevin A.

    2008-01-01

    Summary The fatty acid biosynthesis pathway is an attractive but still largely unexploited target for development of new anti-bacterial agents. The extended use of the anti-tuberculosis drug isoniazid and the antiseptic triclosan, which are inhibitors of fatty acid biosynthesis, validates this pathway as a target for anti-bacterial development. Differences in subcellular organization of the bacterial and eukaryotic multi-enzyme fatty acid synthase systems offer the prospect of inhibitors with host vs. target specificity. Platensimycin, platencin, and phomallenic acids, newly discovered natural product inhibitors of the condensation steps in fatty acid biosynthesis, represent new classes of compounds with antibiotic potential. An almost complete catalogue of crystal structures for the enzymes of the type II fatty acid biosynthesis pathway can now be exploited in the rational design of new inhibitors, as well as the recently published crystal structures of type I FAS complexes. PMID:17707686

  12. Antibacterial targets in fatty acid biosynthesis.

    PubMed

    Wright, H Tonie; Reynolds, Kevin A

    2007-10-01

    The fatty acid biosynthesis pathway is an attractive but still largely unexploited target for the development of new antibacterial agents. The extended use of the antituberculosis drug isoniazid and the antiseptic triclosan, which are inhibitors of fatty acid biosynthesis, validates this pathway as a target for antibacterial development. Differences in subcellular organization of the bacterial and eukaryotic multienzyme fatty acid synthase systems offer the prospect of inhibitors with host versus target specificity. Platensimycin, platencin, and phomallenic acids, newly discovered natural product inhibitors of the condensation steps in fatty acid biosynthesis, represent new classes of compounds with antibiotic potential. An almost complete catalog of crystal structures for the enzymes of the type II fatty acid biosynthesis pathway can now be exploited in the rational design of new inhibitors, as well as the recently published crystal structures of type I FAS complexes.

  13. Cellular Effects of Perfluorinated Fatty Acids.

    DTIC Science & Technology

    1985-01-01

    TCDD appeared to interfere with fatty acid metabolism leading to an increase in unsaturation. Furthermore, Andersen et al. (2) proposed that such an...increase in cellular unsaturated fatty acids may lead-to excessive membrane fluidity (as indicated by induced changes in red blood cell fragility) and...TASK WORK UNITELEMENT NO. NO. NO. NO. 11. TITLE (include Security Claificati on) ~/~. Cellular Effects of Perfluorinated Fatty Ac ds 12. PERSONAL

  14. [Effect of Gram-negative bacteria on fatty acids].

    PubMed

    Vuillemin, N; Dupeyron, C; Leluan, G; Bory, J

    1981-01-01

    The gram-negative bacteria investigated exert various effects on fatty acids. P. aeruginosa and A. calcoaceticus catabolize any of the fatty acids tested. S. marcescens is effective upon all fatty acids excepting butyric acid. The long chain fatty acids only are degraded by E. coli, meanwhile the other fatty acids present a bacteriostatic or bactericidal activity on it. The authors propose a simple and original method for testing the capability of degradation of fatty acids by some bacterial species.

  15. Physiological activities of hydroxyl fatty acids

    USDA-ARS?s Scientific Manuscript database

    In the search of value-added products from surplus soybean oil, we produced many new hydroxy fatty acids through microbial bioconversion. Hydroxy fatty acids are used in a wide range of industrial products, such as resins, waxes, nylons plastics, lubricants, cosmetics, and additives in coatings and...

  16. Fatty acids in an estuarine mangrove ecosystem.

    PubMed

    Alikunhi, Nabeel M; Narayanasamy, Rajendran; Kandasamy, Kathiresan

    2010-06-01

    Fatty acids have been successfully used to trace the transfer of organic matter in coastal and estuarine food webs. To delineate these web connections, fatty acid profiles were analyzed in species of microbes (Azotobacter vinelandii, and Lactobacillus xylosus), prawns (Metapenaeus monoceros and Macrobrachium rosenbergii) and finfish (Mugil cephalus), that are associated with decomposing leaves of two mangrove species, Rhizophora apiculata and Avicennia marina. The fatty acids, except long chain fatty acids, exhibit changes during decomposition of mangrove leaves with a reduction of saturated fatty acids and an increase of monounsaturated fatty acids. The branched fatty acids are absent in undecomposed mangrove leaves, but present significantly in the decomposed leaves and in prawns and finfish, representing an important source for them. This revealed that the microbes are dominant producers that contribute significantly to the fishes and prawns in the mangrove ecosystem. This work has proved the fatty acid biomarkers as an effective tool for identifying the trophic interactions among dominant producers and consumers in this mangrove.

  17. Nickel Inhibits Mitochondrial Fatty Acid Oxidation

    PubMed Central

    Uppala, Radha; McKinney, Richard W.; Brant, Kelly A.; Fabisiak, James P.; Goetzman, Eric S.

    2015-01-01

    Nickel exposure is associated with changes in cellular energy metabolism which may contribute to its carcinogenic properties. Here, we demonstrate that nickel strongly represses mitochondrial fatty acid oxidation—the pathway by which fatty acids are catabolized for energy—in both primary human lung fibroblasts and mouse embryonic fibroblasts. At the concentrations used, nickel suppresses fatty acid oxidation without globally suppressing mitochondrial function as evidenced by increased glucose oxidation to CO2. Pre-treatment with L-carnitine, previously shown to prevent nickel-induced mitochondrial dysfunction in neuroblastoma cells, did not prevent the inhibition of fatty acid oxidation. The effect of nickel on fatty acid oxidation occurred only with prolonged exposure (>5 hr), suggesting that direct inhibition of the active sites of metabolic enzymes is not the mechanism of action. Nickel is a known hypoxia-mimetic that activates hypoxia inducible factor-1α (HIF1α). Nickel-induced inhibition of fatty acid oxidation was blunted in HIF1α knockout fibroblasts, implicating HIF1α as one contributor to the mechanism. Additionally, nickel down-regulated the protein levels of the key fatty acid oxidation enzyme very long-chain acyl-CoA dehydrogenase (VLCAD) in a dose-dependent fashion. In conclusion, inhibition of fatty acid oxidation by nickel, concurrent with increased glucose metabolism, represents a form of metabolic reprogramming that may contribute to nickel-induced carcinogenesis. PMID:26051273

  18. Nickel inhibits mitochondrial fatty acid oxidation.

    PubMed

    Uppala, Radha; McKinney, Richard W; Brant, Kelly A; Fabisiak, James P; Goetzman, Eric S

    2015-08-07

    Nickel exposure is associated with changes in cellular energy metabolism which may contribute to its carcinogenic properties. Here, we demonstrate that nickel strongly represses mitochondrial fatty acid oxidation-the pathway by which fatty acids are catabolized for energy-in both primary human lung fibroblasts and mouse embryonic fibroblasts. At the concentrations used, nickel suppresses fatty acid oxidation without globally suppressing mitochondrial function as evidenced by increased glucose oxidation to CO2. Pre-treatment with l-carnitine, previously shown to prevent nickel-induced mitochondrial dysfunction in neuroblastoma cells, did not prevent the inhibition of fatty acid oxidation. The effect of nickel on fatty acid oxidation occurred only with prolonged exposure (>5 h), suggesting that direct inhibition of the active sites of metabolic enzymes is not the mechanism of action. Nickel is a known hypoxia-mimetic that activates hypoxia inducible factor-1α (HIF1α). Nickel-induced inhibition of fatty acid oxidation was blunted in HIF1α knockout fibroblasts, implicating HIF1α as one contributor to the mechanism. Additionally, nickel down-regulated the protein levels of the key fatty acid oxidation enzyme very long-chain acyl-CoA dehydrogenase (VLCAD) in a dose-dependent fashion. In conclusion, inhibition of fatty acid oxidation by nickel, concurrent with increased glucose metabolism, represents a form of metabolic reprogramming that may contribute to nickel-induced carcinogenesis.

  19. 21 CFR 172.860 - Fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Fatty acids. 172.860 Section 172.860 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.860 Fatty acids...

  20. Incorporation of Extracellular Fatty Acids by a Fatty Acid Kinase-Dependent Pathway in Staphylococcus aureus

    PubMed Central

    Parsons, Joshua B.; Frank, Matthew W.; Jackson, Pamela; Subramanian, Chitra; Rock, Charles O.

    2014-01-01

    Summary Acyl-CoA and acyl-acyl carrier protein (ACP) synthetases activate exogenous fatty acids for incorporation into phospholipids in Gram-negative bacteria. However, Gram-positive bacteria utilize an acyltransferase pathway for the biogenesis of phosphatidic acid that begins with the acylation of sn-glycerol-3-phosphate by PlsY using an acyl-phosphate (acyl-PO4) intermediate. PlsX generates acyl-PO4 from the acyl-ACP end-products of fatty acid synthesis. The plsX gene of Staphylococcus aureus was inactivated and the resulting strain was both a fatty acid auxotroph and required de novo fatty acid synthesis for growth. Exogenous fatty acids were only incorporated into the 1-position and endogenous acyl groups were channeled into the 2-position of the phospholipids in strain PDJ39 (ΔplsX). Extracellular fatty acids were not elongated. Removal of the exogenous fatty acid supplement led to the rapid accumulation of intracellular acyl-ACP and the abrupt cessation of fatty acid synthesis. Extracts from the ΔplsX strain exhibited an ATP-dependent fatty acid kinase activity, and the acyl-PO4 was converted to acyl-ACP when purified PlsX is added. These data reveal the existence of a novel fatty acid kinase pathway for the incorporation of exogenous fatty acids into S. aureus phospholipids. PMID:24673884

  1. Isolation and identification of fatty acid amides from Shengli coal

    SciTech Connect

    Ming-Jie Ding; Zhi-Min Zong; Ying Zong; Xiao-Dong Ou-Yang; Yao-Guo Huang; Lei Zhou; Feng Wang; Jiang-Pei Cao; Xian-Yong Wei

    2008-07-15

    Shengli coal, a Chinese brown coal, was extracted with carbon disulfide and the extract was gradiently eluted with n-hexane and ethyl acetate (EA)/n-hexane mixed solvents with different concentrations of EA in a silica gel-filled column. A series of fatty acid amides, including fourteen alkanamides (C{sub 15}-C{sub 28}) and three alkenamides (C{sub 18} and C{sub 22}), were isolated from the coal by this method and analyzed with a gas chromatography/mass spectrometry. 26 refs., 2 figs., 2 tabs.

  2. Consequences of Essential Fatty Acids

    PubMed Central

    Lands, Bill

    2012-01-01

    Essential fatty acids (EFA) are nutrients that form an amazingly large array of bioactive mediators that act on a large family of selective receptors. Nearly every cell and tissue in the human body expresses at least one of these receptors, allowing EFA-based signaling to influence nearly every aspect of human physiology. In this way, the health consequences of specific gene-environment interactions with these nutrients are more extensive than often recognized. The metabolic transformations have similar competitive dynamics for the n-3 and n-6 homologs when converting dietary EFA from the external environment of foods into the highly unsaturated fatty acid (HUFA) esters that accumulate in the internal environment of cells and tissues. In contrast, the formation and action of bioactive mediators during tissue responses to stimuli tend to selectively create more intense consequences for n-6 than n-3 homologs. Both n-3 and n-6 nutrients have beneficial actions, but many common health disorders are undesired consequences of excessive actions of tissue n-6 HUFA which are preventable. This review considers the possibility of preventing imbalances in dietary n-3 and n-6 nutrients with informed voluntary food choices. That action may prevent the unintended consequences that come from eating imbalanced diets which support excessive chronic actions of n-6 mediators that harm human health. The consequences from preventing n-3 and n-6 nutrient imbalances on a nationwide scale may be very large, and they need careful evaluation and implementation to avoid further harmful consequences for the national economy. PMID:23112921

  3. Omega-3 fatty acids and anorexia.

    PubMed

    Goncalves, Carolina G; Ramos, Eduardo J B; Suzuki, Susumu; Meguid, Michael M

    2005-07-01

    To review the mechanisms of action of omega-3 fatty acids and their role in the brain, as well as their therapeutic implications in anorexia. Recent studies have demonstrated that omega-3 fatty acids modulate changes in the concentrations and actions of several orexigenic and anorexigenic neuropeptides in the brain, including neuropeptide Y, alpha-melanocyte stimulating hormone and the neurotransmitters serotonin and dopamine. In patients with acute and chronic inflammatory conditions, low tissue concentrations of omega-3 fatty acids and high concentrations of proinflammatory cytokines are found, in association with anorexia and decreased food intake. The data suggest that omega-3 fatty acid supplementation suppresses proinflammatory cytokine production and improves food intake by normalizing hypothalamic orexigenic peptides and neurotransmitters. Based on current data, omega-3 fatty acid supplementation has a role in the treatment of anorexia by stimulating the production and release of orexigenic neurotransmitters in food intake regulatory nuclei in the hypothalamus.

  4. Design, synthesis and 64Cu labeling of fatty acid analogs containing dithiosemicarbazone chelate.

    PubMed

    Arano, Y; Magata, Y; Horiuchi, K; Matsumoto, K; Fujibayashi, Y; Ohmomo, Y; Tanaka, C; Saji, H; Yokoyama, A

    1989-01-01

    For the development of 62Cu labeled fatty acid analogs, two fatty acid analogs, containing dithiosemicarbazone (DTS) molecule as the 62Cu coordinating site, were designed and synthesized: a fatty acid analog containing DTS molecule at the omega-position, (a) the 12,13-dioxotetradecanoic acid di(N-methyl-thiosemicarbazone) (FA-DTS), and an omega-phenyl fatty acid analog containing DTS molecule at the para-position, (b) the p-carboxyundecylphenylglyoxal-di (N-methylthiosemicarbazone] (PFA-DTS). FA-DTS was synthesized by the reaction of ethyl diethoxyacetate with ethyl 11-bromonundecanate by successive decarboxylation and hydrolysis and final condensation with N-methylthiosemicarbazide. PFA-DTS was synthesized by the Friedel-Craft acylation of ethyl 11-phenylundecanate, selenium oxidation of the acetophenone derivative, followed by the condensation with N-methylthiosemicarbazide. Radiolabeling of FA-DTS and PFA-DTS with [64Cu]copper acetate was simple, rapid and quantitative. When injected into mice, both compounds were distributed and retained in the myocardium. These results offer a good basis for further development of 62Cu labeled fatty acid analogs.

  5. Occurrence of free fatty acids in the phloem sap of different citrus varieties.

    PubMed

    Valim, Maria Filomena; Killiny, Nabil

    2017-06-03

    Candidatus Liberibacter asiaticus is a phloem restricted bacterium that causes citrus greening disease or huanglongbing (HLB), a major treat to commercial citrus production in Florida. It is transmitted by the Asian citrus psyllid, a phloem sap-feeding insect. Studies conducted on the composition of citrus phloem sap revealed the presence amino acids, organic acids and sugars and of low amounts of free fatty acids. In the present study, the phloem sap of 12 citrus varieties with different degrees of tolerance to HLB were extracted with ethyl acetate and analyzed by GC-MS after derivatization with boron trifluoride, a fatty acid-specific reagent. Nine free fatty acids were detected in all varieties. Of the 9 fatty acids detected, only capric acid was significantly different among varieties.

  6. Relative irritancy of free fatty acids of different chain length.

    PubMed

    Stillman, M A; Maibach, H I; Shalita, A R

    1975-01-01

    Free fatty acids of human skin surface lipids have previously been implicated in the pathogenesis of acne vulgaris because of their apparent irritant and comedogenic properties. Prior studies on the relative irritancy of free fatty acids revealed the saturated C8 to C14 fatty acids and a C18 dienoic unsaturated fatty acid (linoleic) to be most irritating. Saturated free fatty acids from C3 to C18, and unsaturated C18 free fatty acids were applied daily under occlusive patch tests to human skin until detectable erythema appeared. The most irritating fatty acids were C8 through C12. Of the unsaturated fatty acids tested, only linoleic acid produced irritation.

  7. Bioequivalence Demonstration for Ω-3 Acid Ethyl Ester Formulations: Rationale for Modification of Current Guidance.

    PubMed

    Maki, Kevin C; Johns, Colleen; Harris, William S; Puder, Mark; Freedman, Steven D; Thorsteinsson, Thorsteinn; Daak, Ahmed; Rabinowicz, Adrian L; Sancilio, Frederick D

    2017-02-08

    The US Food and Drug Administration (FDA) draft guidance for establishing bioequivalence (BE) of ω-3 acid ethyl esters (containing both eicosapentaenoic acid [EPA] and docosahexaenoic acid [DHA] as ethyl esters), used to treat severe hypertriglyceridemia, recommends the conduct of 2 studies: one with participants in the fasting state and one with participants in the fed state. For the fasting study, the primary measures of BE are baseline-adjusted EPA and DHA levels in total plasma lipids. For the fed study, the primary measures of BE are EPA and DHA ethyl esters in plasma. This guidance differs from that established for icosapent ethyl (EPA ethyl esters) in which the primary measure of BE is baseline-adjusted total EPA in plasma lipids for both the fasting and fed states. The FDA guidance for ω-3 acid ethyl esters is not supported by their physiologic characteristics and triglyceride-lowering mechanisms because EPA and DHA ethyl esters are best characterized as pro-drugs. This article presents an argument for amending the FDA draft guidance for ω-3 acid ethyl esters to use baseline-adjusted EPA and DHA in total plasma lipids as the primary measures of BE for both fasting and fed conditions. This change would harmonize the approaches for demonstration of BE for ω-3 acid ethyl esters and icosapent ethyl (EPA ethyl esters) products for future development programs and is the most physiologically rational approach to BE testing.

  8. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  9. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  10. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  11. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylic esters of fatty acids. 172.848 Section 172... CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty acids... prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid...

  12. Historical overview of n-3 fatty acids and coronary heart disease.

    PubMed

    Leaf, Alexander

    2008-06-01

    The first evidence that fish oil fatty acids might have a beneficial effect on coronary heart disease came from the discovery that Greenland Eskimos, who have a diet high in n-3 fatty acids, have a lower mortality from coronary heart disease than do Danes and Americans. Long-chain polyunsaturated fatty acids are essential in our diets and can be classified in 2 groups: n-6 fatty acids found in plant seeds and n-3 fatty acids found in marine vertebrates. Further evidence of n-3 benefits to human health include a 1989 study demonstrating a 29% reduction in fatal cardiac arrhythmias among subjects with a recent myocardial infarction who had been advised to consume fish oil. The GISSI-Prevenzione Trial found a significant reduction in relative reduction of death, cardiac death, nonfatal myocardial infarction, and stroke in subjects consuming n-3 fatty acids. In a recent study, subjects with implanted cardiac defibrillators (ICDs) at high risk for fatal ventricular arrhythmias were randomly assigned to four 1-g capsules of either an ethyl ester concentrate of n-3 fatty acids or olive oil daily for 12 mo. Subjects receiving n-3 who thus had significantly higher levels of eicosapentaenoic acid and docosahexaenoic acid in their red blood cell membranes showed a longer time to first ICD events and had a significantly lower relative risk of having an ICD event or probable event (P = 0.033). These studies demonstrate that fish oil fatty acids have beneficial effects on coronary heart disease.

  13. [Omega-3 fatty acids and cognition].

    PubMed

    Hashimoto, Michio

    2014-04-01

    Docosahexaenoic acid, the most abundant omega3 fatty acid in the brain, plays a role in cognitive development, learning ability, neuronal membrane plasticity, synaptogenesis, and neurogenesis, all of which are involved in synaptic transmission and the well-being of normal brain functions, and search on the functionality is still in progress. Establishment of prevention and treatment of neuropsychiatric illnesses, such as dementia is not easy, but from numerous basic and epidemiological studies, increase of omega3 fatty acid dietary intake is reported likely to prevent the onset of dementia. This paper is outlined the relevance of cognitive function and omega3 fatty acids, especially docosahexaenoic acid, and the possibility of preventive effect of the fatty acid on dementia.

  14. Quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria by gas chromatography-mass spectrometry.

    PubMed

    Guan, Wenna; Zhao, Hui; Lu, Xuefeng; Wang, Cong; Yang, Menglong; Bai, Fali

    2011-11-11

    Simple and rapid quantitative determination of fatty-acid-based biofuels is greatly important for the study of genetic engineering progress for biofuels production by microalgae. Ideal biofuels produced from biological systems should be chemically similar to petroleum, like fatty-acid-based molecules including free fatty acids, fatty acid methyl esters, fatty acid ethyl esters, fatty alcohols and fatty alkanes. This study founded a gas chromatography-mass spectrometry (GC-MS) method for simultaneous quantification of seven free fatty acids, nine fatty acid methyl esters, five fatty acid ethyl esters, five fatty alcohols and three fatty alkanes produced by wild-type Synechocystis PCC 6803 and its genetically engineered strain. Data obtained from GC-MS analyses were quantified using internal standard peak area comparisons. The linearity, limit of detection (LOD) and precision (RSD) of the method were evaluated. The results demonstrated that fatty-acid-based biofuels can be directly determined by GC-MS without derivation. Therefore, rapid and reliable quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria can be achieved using the GC-MS method founded in this work.

  15. Interaction of Ethyl Alcohol Vapor with Sulfuric Acid Solutions

    NASA Technical Reports Server (NTRS)

    Leu, Ming-Taun

    2006-01-01

    We investigated the uptake of ethyl alcohol (ethanol) vapor by sulfuric acid solutions over the range approx.40 to approx.80 wt % H2SO4 and temperatures of 193-273 K. Laboratory studies used a fast flow-tube reactor coupled to an electron-impact ionization mass spectrometer for detection of ethanol and reaction products. The uptake coefficients ((gamma)) were measured and found to vary from 0.019 to 0.072, depending upon the acid composition and temperature. At concentrations greater than approx.70 wt % and in dilute solutions colder than 220 K, the values approached approx.0.07. We also determined the effective solubility constant of ethanol in approx.40 wt % H2SO4 in the temperature range 203-223 K. The potential implications to the budget of ethanol in the global troposphere are briefly discussed.

  16. Interaction of Ethyl Alcohol Vapor with Sulfuric Acid Solutions

    NASA Technical Reports Server (NTRS)

    Leu, Ming-Taun

    2006-01-01

    We investigated the uptake of ethyl alcohol (ethanol) vapor by sulfuric acid solutions over the range approx.40 to approx.80 wt % H2SO4 and temperatures of 193-273 K. Laboratory studies used a fast flow-tube reactor coupled to an electron-impact ionization mass spectrometer for detection of ethanol and reaction products. The uptake coefficients ((gamma)) were measured and found to vary from 0.019 to 0.072, depending upon the acid composition and temperature. At concentrations greater than approx.70 wt % and in dilute solutions colder than 220 K, the values approached approx.0.07. We also determined the effective solubility constant of ethanol in approx.40 wt % H2SO4 in the temperature range 203-223 K. The potential implications to the budget of ethanol in the global troposphere are briefly discussed.

  17. Fatty acid mobilization and comparison to milk fatty acid content in northern elephant seals.

    PubMed

    Fowler, Melinda A; Debier, Cathy; Mignolet, Eric; Linard, Clementine; Crocker, Daniel E; Costa, Daniel P

    2014-01-01

    A fundamental feature of the life history of true seals, bears and baleen whales is lactation while fasting. This study examined the mobilization of fatty acids from blubber and their subsequent partitioning into maternal metabolism and milk production in northern elephant seals (Mirounga angustirostris). The fatty acid composition of blubber and milk was measured in both early and late lactation. Proportions of fatty acids in milk and blubber were found to display a high degree of similarity both early and late in lactation. Seals mobilized an enormous amount of lipid (~66 kg in 17 days), but thermoregulatory fatty acids, those that remain fluid at low temperatures, were relatively conserved in the outer blubber layer. Despite the stratification, the pattern of mobilization of specific fatty acids conforms to biochemical predictions. Long chain (>20C) monounsaturated fatty acids (MUFAs) were the least mobilized from blubber and the only class of fatty acids that showed a proportional increase in milk in late lactation. Polyunsaturated fatty acids (PUFAs) and saturated fatty acids (SFAs) were more mobilized from the blubber, but neither proportion increased in milk at late lactation. These data suggest that of the long chain MUFA mobilized, the majority is directed to milk synthesis. The mother may preferentially use PUFA and SFA for her own metabolism, decreasing the availability for deposition into milk. The potential impacts of milk fatty acid delivery on pup diving development and thermoregulation are exciting avenues for exploration.

  18. Omega-3 fatty acids and cardiovascular disease.

    PubMed

    Jain, A P; Aggarwal, K K; Zhang, P-Y

    2015-01-01

    Cardioceuticals are nutritional supplements that contain all the essential nutrients including vitamins, minerals, omega-3-fatty acids and other antioxidants like a-lipoic acid and coenzyme Q10 in the right proportion that provide all round protection to the heart by reducing the most common risks associated with the cardiovascular disease including high low-density lipoprotein cholesterol and triglyceride levels and factors that contribute to coagulation of blood. Omega-3 fatty acids have been shown to significantly reduce the risk for sudden death caused by cardiac arrhythmias and all-cause mortality in patients with known coronary heart disease. Omega-3 fatty acids are also used to treat hyperlipidemia and hypertension. There are no significant drug interactions with omega-3 fatty acids. The American Heart Association recommends consumption of two servings of fish per week for persons with no history of coronary heart disease and at least one serving of fish daily for those with known coronary heart disease. Approximately 1 g/day of eicosapentaenoic acid plus docosahexaenoic acid is recommended for cardio protection. Higher dosages of omega-3 fatty acids are required to reduce elevated triglyceride levels (2-4 g/day). Modest decreases in blood pressure occur with significantly higher dosages of omega-3 fatty acids.

  19. Fatty acid synthesis is inhibited by inefficient utilization of unusual fatty acids for glycerolipid assembly

    PubMed Central

    Bates, Philip D.; Johnson, Sean R.; Cao, Xia; Li, Jia; Nam, Jeong-Won; Jaworski, Jan G.; Ohlrogge, John B.; Browse, John

    2014-01-01

    Degradation of unusual fatty acids through β-oxidation within transgenic plants has long been hypothesized as a major factor limiting the production of industrially useful unusual fatty acids in seed oils. Arabidopsis seeds expressing the castor fatty acid hydroxylase accumulate hydroxylated fatty acids up to 17% of total fatty acids in seed triacylglycerols; however, total seed oil is also reduced up to 50%. Investigations into the cause of the reduced oil phenotype through in vivo [14C]acetate and [3H]2O metabolic labeling of developing seeds surprisingly revealed that the rate of de novo fatty acid synthesis within the transgenic seeds was approximately half that of control seeds. RNAseq analysis indicated no changes in expression of fatty acid synthesis genes in hydroxylase-expressing plants. However, differential [14C]acetate and [14C]malonate metabolic labeling of hydroxylase-expressing seeds indicated the in vivo acetyl–CoA carboxylase activity was reduced to approximately half that of control seeds. Therefore, the reduction of oil content in the transgenic seeds is consistent with reduced de novo fatty acid synthesis in the plastid rather than fatty acid degradation. Intriguingly, the coexpression of triacylglycerol synthesis isozymes from castor along with the fatty acid hydroxylase alleviated the reduced acetyl–CoA carboxylase activity, restored the rate of fatty acid synthesis, and the accumulation of seed oil was substantially recovered. Together these results suggest a previously unidentified mechanism that detects inefficient utilization of unusual fatty acids within the endoplasmic reticulum and activates an endogenous pathway for posttranslational reduction of fatty acid synthesis within the plastid. PMID:24398521

  20. 40 CFR 721.7290 - Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Propanoic acid, 2-(trimethoxysilyl... Specific Chemical Substances § 721.7290 Propanoic acid, 2-(trimethoxysilyl)-, ethyl ester. (a) Chemical... acid, 2-(trimethoxysilyl)-, ethyl ester (PMN P-01-22; CAS No. 137787-41-8) is subject to reporting...

  1. Omega-3 fatty acids for cystic fibrosis.

    PubMed

    Oliver, Colleen; Jahnke, Nikki

    2011-08-10

    Studies suggest that a diet rich in omega-3 essential fatty acids may have beneficial anti-inflammatory effects for chronic conditions such as cystic fibrosis. To determine whether there is evidence that omega-3 polyunsaturated fatty acid supplementation reduces morbidity and mortality and to identify any adverse events associated with supplementation. We searched the Cochrane Cystic Fibrosis and Genetic Disorders Group's Trials Register comprising references identified from comprehensive electronic database searches and handsearches of relevant journals and abstract books of conference proceedings. Authors and persons interested in the subject of the review were contacted.Date of last search: 10 March 2011. Randomised controlled trials in people with cystic fibrosis comparing omega-3 fatty acid supplements with placebo. Two authors independently selected studies for inclusion, extracted data and assessed the risk of bias of the studies. The searches identified 13 studies; four studies with 91 participants were included. Two studies compared omega-3 fatty acids to olive oil for six weeks. One study compared a liquid dietary supplement containing omega-3 fatty acids to one without for six months. One study compared omega-3 fatty acids and omega-6 fatty acids to a control (capsules with customised fatty acid blends) for three months. Only one short-term study (19 participants) comparing omega-3 to placebo reported a significant improvement in lung function and Shwachman score and a reduction in sputum volume in the omega-3 group. Another study (43 participants) demonstrated a significant increase in serum phospholipid essential fatty acid content and a significant drop in the n-6/n-3 fatty acid ratio following omega-3 fatty acid supplementation compared to control. The longer-term study (17 participants) demonstrated a significant increase in essential fatty acid content in neutrophil membranes and a significant decrease in the leukotriene B4 to leukotriene B5 ratio

  2. PPARs: fatty acid sensors controlling metabolism.

    PubMed

    Poulsen, Lars la Cour; Siersbæk, Majken; Mandrup, Susanne

    2012-08-01

    The peroxisome proliferator activated receptors (PPARs) are nuclear receptors that play key roles in the regulation of lipid metabolism, inflammation, cellular growth, and differentiation. The receptors bind and are activated by a broad range of fatty acids and fatty acid derivatives and they thereby serve as major transcriptional sensors of fatty acids. Here we review the function, regulation, and mechanism of the different PPAR subtypes with special emphasis on their role in the regulation of lipid metabolism. Copyright © 2012 Elsevier Ltd. All rights reserved.

  3. Omega-3 Fatty Acid supplementation during pregnancy.

    PubMed

    Greenberg, James A; Bell, Stacey J; Ausdal, Wendy Van

    2008-01-01

    Omega-3 fatty acids are essential and can only be obtained from the diet. The requirements during pregnancy have not been established, but likely exceed that of a nonpregnant state. Omega-3 fatty acids are critical for fetal neurodevelopment and may be important for the timing of gestation and birth weight as well. Most pregnant women likely do not get enough omega-3 fatty acids because the major dietary source, seafood, is restricted to 2 servings a week. For pregnant women to obtain adequate omega-3 fatty acids, a variety of sources should be consumed: vegetable oils, 2 low-mercury fish servings a week, and supplements (fish oil or algae-based docosahexaenoic acid).

  4. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Lactylic esters of fatty acids. 172.848 Section... § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty acids may be safely used in food in accordance with the following prescribed conditions: (a) They are prepared from lactic acid and fatty acids...

  5. Polyunsaturated fatty acid supplementation reverses cystic fibrosis-related fatty acid abnormalities in CFTR-/- mice by suppressing fatty acid desaturases.

    PubMed

    Njoroge, Sarah W; Laposata, Michael; Boyd, Kelli L; Seegmiller, Adam C

    2015-01-01

    Cystic fibrosis patients and model systems exhibit consistent abnormalities in metabolism of polyunsaturated fatty acids that appear to play a role in disease pathophysiology. Recent in vitro studies have suggested that these changes are due to overexpression of fatty acid desaturases that can be reversed by supplementation with the long-chain polyunsaturated fatty acids docosahexaenoate and eicosapentaenoate. However, these findings have not been tested in vivo. The current study aimed to test these results in an in vivo model system, the CFTR(-/-) knockout mouse. When compared with wild-type mice, the knockout mice exhibited fatty acid abnormalities similar to those seen in cystic fibrosis patients and other model systems. The abnormalities were confined to lung, ileum and pancreas, tissues that are affected by the disease. Similar to in vitro models, these fatty acid changes correlated with increased expression of Δ5- and Δ6-desaturases and elongase 5. Dietary supplementation with high-dose free docosahexaenoate or a combination of lower-dose docosahexaenoate and eicosapentaenoate in triglyceride form corrected the fatty acid abnormalities and reduced expression of the desaturase and elongase genes in the ileum and liver of knockout mice. Only the high-dose docosahexaenoate reduced histologic evidence of disease, reducing mucus accumulation in ileal sections. These results provide in vivo support for the hypothesis that fatty acid abnormalities in cystic fibrosis result from abnormal expression and activity of metabolic enzymes in affected cell types. They further demonstrate that these changes can be reversed by dietary n-3 fatty acid supplementation, highlighting the potential therapeutic benefit for cystic fibrosis patients.

  6. Saturated Fatty Acid Mutant of Saccharomyces cerevisiae with an Intact Fatty Acid Synthetase

    PubMed Central

    Meyer, Karl H.; Schweizer, Eckhart

    1974-01-01

    A Saccharomyces cerevisiae conditional mutant, LK 181, is described which grows at 37 C only when supplemented with a saturated fatty acid of 12 to 14 carbon atoms chain length. At 22 C, however, no fatty acid supplementation is required for growth. The fatty acid concentration required for optimal growth at 37 C is about four times lower for LK 181 than for fatty acid synthetase-deficient mutants. In contrast to all fatty acid synthetase mutants so far examined, mutant LK 181 cannot grow with palmitic acid. The addition of palmitic, palmitoleic, or oleic acid to the culture medium prevents LK 181 growth at temperatures between 22 and 37 C. In vivo as well as in vitro, cellular de novo fatty acid biosynthesis from acetate is unimpaired in this mutant. It is suggested that endogenously synthesized fatty acids, due to their chain lengths of 16 and more carbon atoms, cannot supplement the mutant LK 181. It is concluded that the exogeneously supplied fatty acids act as allosteric effectors for a mutationally altered cellular protein to restore its biological function at elevated temperatures, rather than as a substitute for endogenously synthesized long-chain fatty acids. PMID:4590462

  7. Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

    PubMed Central

    Bruns, Hilke; Riclea, Ramona

    2011-01-01

    Summary The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω−1)-branched, (ω−2)-branched, α- and (ω−1)-branched, γ- and (ω−1)-branched, γ- and (ω−2)-branched, and γ- and (ω−3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). PMID:22238549

  8. Antisense technologies targeting fatty acid synthetic enzymes.

    PubMed

    Lin, Jinshun; Liu, Feng; Jiang, Yuyang

    2012-05-01

    Fatty acid synthesis is a coordinated process involving multiple enzymes. Overexpression of some of these enzymes plays important roles in tumor growth and development. Therefore, these enzymes are attractive targets for cancer therapies. Antisense agents provide highly specific inhibition of the expression of target genes and thus have served as powerful tools for gene functional studies and potential therapeutic agents for cancers. This article reviews different types of antisense agents and their applications in the modulation of fatty acid synthesis. Patents of antisense agents targeting fatty acid synthetic enzymes are introduced. In addition, miR-122 has been shown to regulate the expression of fatty acid synthetic enzymes, and thus antisense agent patents that inhibit miR-122 expression are also discussed.

  9. Introduction to fatty acids and lipids.

    PubMed

    Burdge, Graham C; Calder, Philip C

    2015-01-01

    The purpose of this article is to describe the structure, function and metabolism of fatty acids and lipids that are of particular importance in the context of parenteral nutrition. Lipids are a heterogeneous group of molecules that share the common property of hydrophobicity. Lipids range in structure from simple short hydrocarbon chains to more complex molecules, including triacylglycerols, phospholipids and sterols and their esters. Lipids within each class may differ structurally. Fatty acids are common components of complex lipids, and these differ according to chain length and the presence, number and position of double bonds in the hydrocarbon chain. Structural variation among complex lipids and among fatty acids gives rise to functional differences that result in different impacts upon metabolism and upon cell and tissue responses. Fatty acids and complex lipids exhibit a variety of structural variations that influence their metabolism and their functional effects.

  10. Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review.

    PubMed

    Milchert, Eugeniusz; Malarczyk, Kornelia; Kłos, Marlena

    2015-12-02

    The general subject of the review is analysis of the effect of technological parameters on the chemoenzymatic epoxidation processes of vegetable oils, fatty acids and alkyl esters of fatty acids. The technological parameters considered include temperature, concentration, amount of hydrogen peroxide relative to the number of unsaturated bonds, the amounts of enzyme catalysts, presence of solvent and amount of free fatty acids. Also chemical reactions accompanying the technological processes are discussed together with different technological options and significance of the products obtained.

  11. 21 CFR 172.863 - Salts of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Salts of fatty acids. 172.863 Section 172.863 Food... of fatty acids. The food additive salts of fatty acids may be safely used in food and in the... salts of the fatty acids conforming with § 172.860 and/or oleic acid derived from tall oil fatty acids...

  12. Dietary omega-3 fatty acids for women.

    PubMed

    Bourre, Jean-Marie

    2007-01-01

    This review details the specific needs of women for omega-3 fatty acids, including alpha linoleic acid (ALA) and the very long chain fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Omega-3 fatty acid (dietary or in capsules) ensures that a woman's adipose tissue contains a reserve of these fatty acids for the developing fetus and the breast-fed newborn infant. This ensures the optimal cerebral and cognitive development of the infant. The presence of large quantities of EPA and DHA in the diet slightly lengthens pregnancy, and improves its quality. Human milk contains both ALA and DHA, unlike that of other mammals. Conditions such as diabetes can alter the fatty acid profile of mother's milk, while certain diets, like those of vegetarians, vegans, or even macrobiotic diets, can have the same effect, if they do not include seafood. ALA, DHA and EPA, are important for preventing ischemic cardiovascular disease in women of all ages. Omega-3 fatty acids can help to prevent the development of certain cancers, particularly those of the breast and colon, and possibly of the uterus and the skin, and are likely to reduce the risk of postpartum depression, manic-depressive psychosis, dementias (Alzheimer's disease and others), hypertension, toxemia, diabetes and, to a certain extend, age-related macular degeneration. Omega-3 fatty acids could play a positive role in the prevention of menstrual syndrome and postmenopausal hot flushes. The normal western diet contains little ALA (less than 50% of the RDA). The only adequate sources are rapeseed oil (canola), walnuts and so-called "omega-3" eggs (similar to wild-type or Cretan eggs). The amounts of EPA and DHA in the diet vary greatly from person to person. The only good sources are fish and seafood, together with "omega-3" eggs.

  13. Fatty acid oxidation and ketogenesis in astrocytes

    SciTech Connect

    Auestad, N.

    1988-01-01

    Astrocytes were derived from cortex of two-day-old rat brain and grown in primary culture to confluence. The metabolism of the fatty acids, octanoate and palmitate, to CO{sub 2} in oxidative respiration and to the formation of ketone bodies was examined by radiolabeled tracer methodology. The net production of acetoacetate was also determined by measurement of its mass. The enzymes in the ketogenic pathway were examined by measuring enzymic activity and/or by immunoblot analyses. Labeled CO{sub 2} and labeled ketone bodies were produced from the oxidation of fatty acids labeled at carboxy- and {omega}-terminal carbons, indicating that fatty acids were oxidized by {beta}-oxidation. The results from the radiolabeled tracer studies also indicated that a substantial proportion of the {omega}-terminal 4-carbon unit of the fatty acids bypassed the {beta}-ketothiolase step of the {beta}-oxidation pathway. The ({sup 14}C)acetoacetate formed from the (1-{sup 14}C)labeled fatty acids, obligated to pass through the acetyl-CoA pool, contained 50% of the label at carbon 3 and 50% at carbon 1. In contrast, the ({sup 14}C)acetoacetate formed from the ({omega}-1)labeled fatty acids contained 90% of the label at carbon 3 and 10% at carbon 1.

  14. [Elimination of all trans fatty acids].

    PubMed

    Katan, M B

    2008-02-09

    At the start of the 20th century, the production of trans fatty acids was originally largely driven by the increasing demand for margarine. The two Dutch margarine firms Van den Bergh and Jurgens played an important role in this early development. In the early 1990s it was shown that trans fatty acids increase the risk of heart disease. Unilever, the successor to Van den Bergh and Jurgens, then took the lead in eliminating trans fatty acids from retail foods worldwide. As a result, intake in The Netherlands fell from 15 g per day in 1980 to 3 g per day in 2003. Dairy products and meat are now the major source of trans fatty acids. The effects on health of these ruminant trans fatty acids are unclear. There are three lessons to be learned from the rise and fall of trans fatty acids. First, a history of safe use does not guarantee safety of food components, because routine surveillance will fail to detect adverse effects on common illnesses with long incubation periods. Second, it shows that it is more effective and easier to change the composition of foods than to change consumer behaviour. And third, governments can have a major impact on consumers' health by mandating the use of healthier food ingredients.

  15. 21 CFR 172.859 - Sucrose fatty acid esters.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Sucrose fatty acid esters. 172.859 Section 172.859... Sucrose fatty acid esters. Sucrose fatty acid esters identified in this section may be safely used in accordance with the following prescribed conditions: (a) Sucrose fatty acid esters are the mono-, di-, and...

  16. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Polyglycerol esters of fatty acids. 172.854... § 172.854 Polyglycerol esters of fatty acids. Polyglycerol esters of fatty acids, up to and including..., safflower oil, sesame oil, soybean oil, and tallow and the fatty acids derived from these substances...

  17. [Biology of essential fatty acids (EFA)].

    PubMed

    Dobryniewski, Jacek; Szajda, Sławomir Dariusz; Waszkiewicz, Napoleon; Zwierz, Krzysztof

    2007-01-01

    Essential Fatty Acids (EFA), are unsaturated fatty acids not produced by human being, but essential for proper functioning of the human body. To EFA-s belongs: linoleic acid (LA) (18:2,cis detla(9,12), omega6)--precursor o f gamma-linolenic acid (GLA), gamma-linolenic acid (GLA) (18:3,cisA6,9,12, )6) and alpha-linolenic acid (ALA)(18:3,cisdelta(9, 12, 15), omega3)--product of dehydrogenation of linoleic acid (LA). Most important EFA is gamma-linolenic acid (GLA)--18 carbons, one-carboxylic, non-branched fatty acid with 3 double cis-bonds (the last is situated by 6-th carbon from methylic end). The diet devoided of EFA leads to decreased growth, skin and kidney injury and infertility. Modern research of GLA and others EFA's is concerned mainly on therapeutic impact on the inflammatory process. The biogenic amines, cytokines, prostaglandins, tromboxanes and leukotrienes are the main inflammatory mediators. The last three are described with the common name eicosanoides (eico-twenty). Eicosanoides are synthesized from 20-carbon unsaturated fatty acids: dihomo-gamma-linoleic (DGLA) (20:3, cis delta(8,11,14), omega6), arachidonic acid (AA-20:4, cis delta(5,8,11,14), omega6), and eicosapentaenoic acid (EPA-20:5, cis delta(5,8,11,14,17, omega3). Derivatives of gamma and gamma-linolenic acids regulate the inflammatory process, through their opposed activity. PG2, leucotrien C4 and tromboxan A2 have the strongest proinflammatory action. Derivatives of alpha-linolenic acid 15-HETE and prostaglandin E1 (PGE1) have weak pro-inflammatory action, or even anti-inflammatory (PGE1), and additionally, they inhibit the transformation of arachidonic acid (AA) to leukotriens. delta6-desaturase (transformes linolenic acid into gamma-linolenic acid by making additional double bond) is the slowest step of the fatty acid metabolism. It's activity is impaired by many physiological and pathologic factors and leads to gamma-linolenic acid (GLA) deficiency. The gamma-linolenic acid

  18. 40 CFR 721.10110 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol. 721.10110 Section 721.10110 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10110 Hexanoic acid, 2-ethyl-, mixed...

  19. 40 CFR 721.10110 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol. 721.10110 Section 721.10110 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10110 Hexanoic acid, 2-ethyl-, mixed...

  20. 40 CFR 721.10111 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol. 721.10111 Section 721.10111 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10111 Hexanoic acid, 2-ethyl-, mixed...

  1. 40 CFR 721.10111 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol. 721.10111 Section 721.10111 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10111 Hexanoic acid, 2-ethyl-, mixed...

  2. 40 CFR 721.10110 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol. 721.10110 Section 721.10110 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10110 Hexanoic acid, 2-ethyl-, mixed...

  3. 40 CFR 721.10110 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and neopentlyl glycol. 721.10110 Section 721.10110 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10110 Hexanoic acid, 2-ethyl-, mixed...

  4. 40 CFR 721.10111 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol. 721.10111 Section 721.10111 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10111 Hexanoic acid, 2-ethyl-, mixed...

  5. 40 CFR 721.10111 - Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Hexanoic acid, 2-ethyl-, mixed diesters with benzoic acid and diethylene glycol. 721.10111 Section 721.10111 Protection of Environment... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10111 Hexanoic acid, 2-ethyl-, mixed...

  6. Fatty acid-binding site environments of serum vitamin D-binding protein and albumin are different

    PubMed Central

    Swamy, Narasimha; Ray, Rahul

    2008-01-01

    Vitamin D-binding protein (DBP) and albumin (ALB) are abundant serum proteins and both possess high-affinity binding for saturated and unsaturated fatty acids. However, certain differences exist. We surmised that in cases where serum albumin level is low, DBP presumably can act as a transporter of fatty acids. To explore this possibility we synthesized several alkylating derivatives of 14C-palmitic acid to probe the fatty acid binding pockets of DBP and ALB. We observed that N-ethyl-5-phenylisooxazolium-3′-sulfonate-ester (WRK ester) of 14C-palmitic acid specifically labeled DBP; but p-nitrophenyl- and N-hydroxysuccinimidyl-esters failed to do so. However, p-nitrophenyl ester of 14C-palmitic acid specifically labeled bovine ALB, indicating that the micro-environment of the fatty acid-binding domains of DBP and ALB may be different; and DBP may not replace ALB as a transporter of fatty acids. PMID:18374965

  7. Omega 3 fatty acids and the eye.

    PubMed

    Cakiner-Egilmez, Tulay

    2008-01-01

    The health benefits of fish oil have been known for decades. Most of the health benefits of fish oil can be attributed to the presence of omega-3 essential fatty acids such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). Clinical studies have suggested that DHA and EPA lower triglycerides; slow the buildup of atherosclerotic plaques; lower blood pressure slightly; as well as reduce the risk of death, heart attack, and arrhythmias. Studies have also shown that omega-3 fatty acids may slow the progression of vision loss from AMD and reverse the signs of dry eye syndrome.

  8. Expression of fatty acid synthase in nonalcoholic fatty liver disease.

    PubMed

    Dorn, Christoph; Riener, Marc-Oliver; Kirovski, Georgi; Saugspier, Michael; Steib, Kathrin; Weiss, Thomas S; Gäbele, Erwin; Kristiansen, Glen; Hartmann, Arndt; Hellerbrand, Claus

    2010-03-25

    Nonalcoholic fatty liver disease (NAFLD) is characterized by hepatic lipid accumulation which starts with simple hepatic steatosis and may progress toward inflammation (nonalcoholic steatohepatitis [NASH]). Fatty acid synthase (FASN) catalyzes the last step in fatty acid biosynthesis, and thus, it is believed to be a major determinant of the maximal hepatic capacity to generate fatty acids by de novo lipogenesis. The aim of this study was to analyze the correlation between hepatic steatosis and inflammation with FASN expression. In vitro incubation of primary human hepatocytes with fatty acids dose-dependently induced cellular lipid-accumulation and FASN expression, while stimulation with TNF did not affect FASN levels. Further, hepatic FASN expression was significantly increased in vivo in a murine model of hepatic steatosis without significant inflammation but not in a murine NASH model as compared to control mice. Also, FASN expression was not increased in mice subjected to bile duct ligation, an experimental model characterized by severe hepatocellular damage and inflammation. Furthermore, FASN expression was analyzed in 102 human control or NAFLD livers applying tissue micro array technology and immunohistochemistry, and correlated significantly with the degree of hepatic steatosis, but not with inflammation or ballooning of hepatocytes. Quantification of FASN mRNA expression in human liver samples confirmed significantly higher FASN levels in hepatic steatosis but not in NASH, and expression of SREBP1, which is the main transcriptional regulator of FASN, paralleled FASN expression levels in human and experimental NAFLD. In conclusion, the transcriptional induction of FASN expression in hepatic steatosis is impaired in NASH, while hepatic inflammation in the absence of steatosis does not affect FASN expression, suggesting that FASN may serve as a new diagnostic marker or therapeutic target for the progression of NAFLD.

  9. Curcumin improves alcoholic fatty liver by inhibiting fatty acid biosynthesis.

    PubMed

    Guo, Chang; Ma, Jingfan; Zhong, Qionghong; Zhao, Mengyuan; Hu, Tianxing; Chen, Tong; Qiu, Longxin; Wen, Longping

    2017-08-01

    Alcoholic fatty liver is a threat to human health. It has been long known that abstinence from alcohol is the most effective therapy, other effective therapies are not available for the treatment in humans. Curcumin has a great potential for anti-oxidation and anti-inflammation, but the effect on metabolic reconstruction remains little known. Here we performed metabolomic analysis by gas chromatography/mass spectrometry and explored ethanol pathogenic insight as well as curcumin action pattern. We identified seventy-one metabolites in mouse liver. Carbohydrates and lipids were characteristic categories. Pathway analysis results revealed that ethanol-induced pathways including biosynthesis of unsaturated fatty acids, fatty acid biosynthesis and pentose and glucuronate interconversions were suppressed by curcumin. Additionally, ethanol enhanced galactose metabolism and pentose phosphate pathway. Glyoxylate and dicarboxylate metabolism and pyruvate metabolism were inhibited in mice fed ethanol diet plus curcumin. Stearic acid, oleic acid and linoleic acid were disease biomarkers and therapical biomarkers. These results reflect the landscape of hepatic metabolism regulation. Our findings illustrate ethanol pathological pathway and metabolic mechanism of curcumin therapy. Copyright © 2017. Published by Elsevier Inc.

  10. Control of bovine hepatic fatty acid oxidation

    SciTech Connect

    Jesse, B.W.; Emery, R.S.; Thomas, J.W.

    1986-09-01

    Fatty acid oxidation by bovine liver slices and mitochondria was examined to determine potential regulatory sites of fatty acid oxidation. Conversion of 1-(/sup 14/C)palmitate to /sup 14/CO/sub 2/ and total (/sup 14/C)acid-soluble metabolites was used to measure fatty acid oxidation. Oxidation of palmitate (1 mM) was linear in both liver slice weight and incubation time. Carnitine stimulated palmitate oxidation; 2 mM dl-carnitine produced maximal stimulation of palmitate oxidation to both CO/sup 2/ and acid-soluble metabolites. Propionate (10 mM) inhibited palmitate oxidation by bovine liver slices. Propionate (.5 to 10 mM) had no effect on palmitate oxidation by mitochondria, but malonyl Coenzyme A, the first committed intermediate of fatty acid synthesis, inhibited mitochondrial palmitate oxidation (inhibition constant = .3 ..mu..M). Liver mitochonndrial carnitine palmitoyltransferase exhibited Michaelis constants for palmitoyl Coenzyme A and l-carnitine of 11.5 ..mu..M and .59 mM, respectively. Long-chain fatty acid oxidation in bovine liver is regulated by mechanisms similar to those in rats but adapted to the unique digestive physiology of the bovine.

  11. Omega-3 fatty acids and athletics.

    PubMed

    Simopoulos, Artemis P

    2007-07-01

    Human beings evolved consuming a diet that contained about equal amounts of y-6 and y-3 essential fatty acids. Today, in Western diets, the ratio of y-6 to y-3 fatty acids ranges from approximately 10:1 to 20:1 instead of the traditional range of 1:1 to 2:1. Studies indicate that a high intake of y-6 fatty acids shifts the physiologic state to one that is prothrombotic and proaggregatory, characterized by increases in blood viscosity, vasospasm, and vasoconstriction, and decreases in bleeding time. y-3 fatty acids, however, have anti-inflammatory, antithrombotic, antiarrhythmic, hypolipidemic, and vasodilatory properties. Excessive radical formation and trauma during high-intensity exercise leads to an inflammatory state that is made worse by the increased amount of y-6 fatty acids in Western diets, although this can be counteracted by eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). For the majority of athletes, especially those at the leisure level, general guidelines should include EPA and DHA of about 1 to 2 g/d at a ratio of EPA:DHA of 2:1.

  12. Ferritin couples iron and fatty acid metabolism.

    PubMed

    Bu, Weiming; Liu, Renyu; Cheung-Lau, Jasmina C; Dmochowski, Ivan J; Loll, Patrick J; Eckenhoff, Roderic G

    2012-06-01

    A physiological relationship between iron, oxidative injury, and fatty acid metabolism exists, but transduction mechanisms are unclear. We propose that the iron storage protein ferritin contains fatty acid binding sites whose occupancy modulates iron uptake and release. Using isothermal microcalorimetry, we found that arachidonic acid binds ferritin specifically and with 60 μM affinity. Arachidonate binding by ferritin enhanced iron mineralization, decreased iron release, and protected the fatty acid from oxidation. Cocrystals of arachidonic acid and horse spleen apoferritin diffracted to 2.18 Å and revealed specific binding to the 2-fold intersubunit pocket. This pocket shields most of the fatty acid and its double bonds from solvent but allows the arachidonate tail to project well into the ferrihydrite mineralization site on the ferritin L-subunit, a structural feature that we implicate in the effects on mineralization by demonstrating that the much shorter saturated fatty acid, caprylate, has no significant effects on mineralization. These combined effects of arachidonate binding by ferritin are expected to lower both intracellular free iron and free arachidonate, thereby providing a previously unrecognized mechanism for limiting lipid peroxidation, free radical damage, and proinflammatory cascades during times of cellular stress.

  13. 40 CFR 721.10629 - Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). 721.10629 Section 721.10629 Protection... Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). (a...

  14. 40 CFR 721.10629 - Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). 721.10629 Section 721.10629 Protection... Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). (a...

  15. Amino and fatty acids in carbonaceous meteorites

    NASA Technical Reports Server (NTRS)

    Kvenvolden, K. A.

    1974-01-01

    Analyses of two carbonaceous meteorites have provided much of the latest evidence which seems to support Oparin's theory on the origin of life. The meteorites involved are the Murray meteorite, which fell in 1950, and the Murchison meteorite, which fell in 1969. The amino acids in the two meteorites are similar in composition. Eight of the twenty amino acids found belong to amino acids present in proteins. A number of monocarboxylic and dicarboxylic fatty acids were also found in the meteorites.

  16. Amino and fatty acids in carbonaceous meteorites

    NASA Technical Reports Server (NTRS)

    Kvenvolden, K. A.

    1974-01-01

    Analyses of two carbonaceous meteorites have provided much of the latest evidence which seems to support Oparin's theory on the origin of life. The meteorites involved are the Murray meteorite, which fell in 1950, and the Murchison meteorite, which fell in 1969. The amino acids in the two meteorites are similar in composition. Eight of the twenty amino acids found belong to amino acids present in proteins. A number of monocarboxylic and dicarboxylic fatty acids were also found in the meteorites.

  17. The Association of Fatty Acids With Breast Cancer.

    DTIC Science & Technology

    1995-08-09

    Experimental studies have shown that omega-6 fatty acids enhance and omega - 3 fatty acids suppress oncogenesis. Correlational studies also indicate...that breast cancer incidence is positively linked to omega-6 consumption but is negatively related to intake of omega - 3 fatty acids, derived mainly from...arachidonic acid), and omega - 3 fatty acids (20:5n3, eicosapentaenoic acid; 22:6n-3, docosahexaenoic acid) were similar in cases and controls

  18. Specific bile acids inhibit hepatic fatty acid uptake

    PubMed Central

    Nie, Biao; Park, Hyo Min; Kazantzis, Melissa; Lin, Min; Henkin, Amy; Ng, Stephanie; Song, Sujin; Chen, Yuli; Tran, Heather; Lai, Robin; Her, Chris; Maher, Jacquelyn J.; Forman, Barry M.; Stahl, Andreas

    2012-01-01

    Bile acids are known to play important roles as detergents in the absorption of hydrophobic nutrients and as signaling molecules in the regulation of metabolism. Here we tested the novel hypothesis that naturally occurring bile acids interfere with protein-mediated hepatic long chain free fatty acid (LCFA) uptake. To this end stable cell lines expressing fatty acid transporters as well as primary hepatocytes from mouse and human livers were incubated with primary and secondary bile acids to determine their effects on LCFA uptake rates. We identified ursodeoxycholic acid (UDCA) and deoxycholic acid (DCA) as the two most potent inhibitors of the liver-specific fatty acid transport protein 5 (FATP5). Both UDCA and DCA were able to inhibit LCFA uptake by primary hepatocytes in a FATP5-dependent manner. Subsequently, mice were treated with these secondary bile acids in vivo to assess their ability to inhibit diet-induced hepatic triglyceride accumulation. Administration of DCA in vivo via injection or as part of a high-fat diet significantly inhibited hepatic fatty acid uptake and reduced liver triglycerides by more than 50%. In summary, the data demonstrate a novel role for specific bile acids, and the secondary bile acid DCA in particular, in the regulation of hepatic LCFA uptake. The results illuminate a previously unappreciated means by which specific bile acids, such as UDCA and DCA, can impact hepatic triglyceride metabolism and may lead to novel approaches to combat obesity-associated fatty liver disease. PMID:22531947

  19. Fatty Acid Synthetase of Saccharomyces cerevisiae

    PubMed Central

    Klein, Harold P.; Volkmann, Carol M.; Chao, Fu-Chuan

    1967-01-01

    A light particle fraction of Saccharomyces cerevisiae, obtained from the crude ribosomal material, and containing the fatty acid synthetase, consisted primarily of 27S and 47S components. This fraction has a protein-ribonucleic acid ratio of about 13. Electron micrographs showed particles ranging in diameter between 100 and 300 A in this material. By use of density gradient analysis, the fatty acid synthetase was found in the 47S component. This component contained particles which were predominantly 300 A in diameter and which were considerably flatter than ribosomes, and it consisted almost entirely of protein. Images PMID:6025308

  20. Mitochondrial fatty acid synthesis and respiration.

    PubMed

    Hiltunen, J Kalervo; Autio, Kaija J; Schonauer, Melissa S; Kursu, V A Samuli; Dieckmann, Carol L; Kastaniotis, Alexander J

    2010-01-01

    Recent studies have revealed that mitochondria are able to synthesize fatty acids in a malonyl-CoA/acyl carrier protein (ACP)-dependent manner. This pathway resembles bacterial fatty acid synthesis (FAS) type II, which uses discrete, nuclearly encoded proteins. Experimental evidence, obtained mainly through using yeast as a model system, indicates that this pathway is essential for mitochondrial respiratory function. Curiously, the deficiency in mitochondrial FAS cannot be complemented by inclusion of fatty acids in the culture medium or by products of the cytosolic FAS complex. Defects in mitochondrial FAS in yeast result in the inability to grow on nonfermentable carbon sources, the loss of mitochondrial cytochromes a/a3 and b, mitochondrial RNA processing defects, and loss of cellular lipoic acid. Eukaryotic FAS II generates octanoyl-ACP, a substrate for mitochondrial lipoic acid synthase. Endogenous lipoic acid synthesis challenges the hypothesis that lipoic acid can be provided as an exogenously supplied vitamin. Purified eukaryotic FAS II enzymes are catalytically active in vitro using substrates with an acyl chain length of up to 16 carbon atoms. However, with the exception of 3-hydroxymyristoyl-ACP, a component of respiratory complex I in higher eukaryotes, the fate of long-chain fatty acids synthesized by the mitochondrial FAS pathway remains an enigma. The linkage of FAS II genes to published animal models for human disease supports the hypothesis that mitochondrial FAS dysfunction leads to the development of disorders in mammals.

  1. Omega 3 fatty acids in the elderly.

    PubMed

    Ubeda, Natalia; Achón, María; Varela-Moreiras, Gregorio

    2012-06-01

    Population ageing affects the entire world population. Also at world level one can observe a sharp increase in the proportion of older people. The challenge posed by population ageing translates into ensuring that the extra years of life will be as good as possible, free from high-cost dependency. Omega-3 fatty acids are now generally recognized as potential key nutrients to prevent the pathological conditions associated to the aging process. Ageing physiological process, its association with quality of life and the impact of omega-3 fatty acids intake and/or status is the focus of the present review. This report deals with the effects of omega-3 fatty acids on normal aging of older adults ( ≥ 65 years) mainly on the effects such as nutritional status itself, cognition, bone health, muscle tonus, and general health status. The preliminary broad search of the literature on the effects of omega-3 fatty acids on normal aging yielded 685 citations. Forty two full text papers were checked for inclusion and thirty six studies were finally included in this review. It may be concluded that paradoxically even though the elderly population is the largest one, the number of studies and the methodology employed clearly lacks of sufficient evidence to establish definite conclusions on the effects of omega-3 fatty acids on aging metabolism without pathological conditions and on quality of life.

  2. Fatty Acid-Derived Biofuels and Chemicals Production in Saccharomyces cerevisiae.

    PubMed

    Zhou, Yongjin J; Buijs, Nicolaas A; Siewers, Verena; Nielsen, Jens

    2014-01-01

    Volatile energy costs and environmental concerns have spurred interest in the development of alternative, renewable, sustainable, and cost-effective energy resources. Environment-friendly processes involving microbes can be used to synthesize advanced biofuels. These fuels have the potential to replace fossil fuels in supporting high-power demanding machinery such as aircrafts and trucks. From an engineering perspective, the pathway for fatty acid biosynthesis is an attractive route for the production of advanced fuels such as fatty acid ethyl esters, fatty alcohols, and alkanes. The robustness and excellent accessibility to molecular genetics make the yeast Saccharomyces cerevisiae a suitable host for the purpose of bio-manufacturing. Recent advances in metabolic engineering, as well as systems and synthetic biology, have now provided the opportunity to engineer yeast metabolism for the production of fatty acid-derived fuels and chemicals.

  3. Fluorescing fatty acids in rat fatty liver models.

    PubMed

    Croce, Anna C; Ferrigno, Andrea; Di Pasqua, Laura G; Berardo, Clarissa; Mannucci, Barbara; Bottiroli, Giovanni; Vairetti, Mariapia

    2017-06-01

    The autofluorescence (AF) of NAD(P)H and flavins has been at the basis of many in-situ studies of liver energy metabolism and functionality. Conversely, few data have been so far reported on fluorescing lipids. In this work we investigated the AF of liver lipid extracts from two fatty liver models, Wistar rats fed with MCD diet for 12 days (Wi-MCD), and obese (fa/fa) Zucker rats. Among the most abundant fatty acids in the lipid extracts, indicated by mass spectrometry, arachidonic acid (AA) exhibited higher quantum yield than the other fluorescing fatty acids (FLFA), and red shifted AF spectrum. This allowed to estimate the AA contribution to the overall emission of lipid extracts by curve fitting analysis. AA prevailed in obese Zucker livers, accounting for the different AF spectral profiles between the two models. AF and mass spectrometry indicated also a different balance between the fluorescing fraction and the overall amount of AA in the two models. The ability of AF to detect directly AA and FLFA was demonstrated, suggesting its supportive role as tool in wide-ranging applications, from the control of animal origin food, to experimental investigations on liver fat accumulation, lipotoxicity and disease progression, with potential translation to the clinics. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  4. Production of hydroxylated fatty acids in genetically modified plants

    DOEpatents

    Somerville, Chris; Broun, Pierre; van de Loo, Frank; Boddupalli, Sekhar S.

    2005-08-30

    This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants. In addition, the use of genes encoding fatty acid hydroxylases or desaturases to alter the level of lipid fatty acid unsaturation in transgenic plants is described.

  5. Production of hydroxylated fatty acids in genetically modified plants

    DOEpatents

    Somerville, Chris [Portola Valley, CA; Broun, Pierre [Burlingame, CA; van de Loo, Frank [Weston, AU; Boddupalli, Sekhar S [Manchester, MI

    2011-08-23

    This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants. In addition, the use of genes encoding fatty acid hydroxylases or desaturases to alter the level of lipid fatty acid unsaturation in transgenic plants is described.

  6. The clinical relevance of omega-3 fatty acids in the management of hypertriglyceridemia.

    PubMed

    Backes, James; Anzalone, Deborah; Hilleman, Daniel; Catini, Julia

    2016-07-22

    Hypertriglyceridemia (triglycerides > 150 mg/dL) affects ~25 % of the United States (US) population and is associated with increased cardiovascular risk. Severe hypertriglyceridemia (≥ 500 mg/dL) is also a risk factor for pancreatitis. Three omega-3 fatty acid (OM3FA) prescription formulations are approved in the US for the treatment of adults with severe hypertriglyceridemia: (1) OM3FA ethyl esters (OM3EE), a mixture of OM3FA ethyl esters, primarily eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) (Lovaza®, Omtryg™, and generics); (2) icosapent ethyl (IPE), EPA ethyl esters (Vascepa®); and (3) omega-3 carboxylic acids (OM3CA), a mixture of OM3FAs in free fatty acid form, primarily EPA, DHA, and docosapentaenoic acid (Epanova®). At approved doses, all formulations substantially reduce triglyceride and very-low-density lipoprotein levels. DHA-containing formulations may also increase low-density lipoprotein cholesterol. However, this is not accompanied by increased non-high-density lipoprotein cholesterol, which is thought to provide a better indication of cardiovascular risk in this patient population. Proposed mechanisms of action of OM3FAs include inhibition of diacylglycerol acyltransferase, increased plasma lipoprotein lipase activity, decreased hepatic lipogenesis, and increased hepatic β-oxidation. OM3CA bioavailability (area under the plasma concentration-time curve from zero to the last measurable concentration) is up to 4-fold greater than that of OM3FA ethyl esters, and unlike ethyl esters, the absorption of OM3CA is not dependent on pancreatic lipase hydrolysis. All three formulations are well tolerated (the most common adverse events are gastrointestinal) and demonstrate a lack of drug-drug interactions with other lipid-lowering drugs, such as statins and fibrates. OM3FAs appear to be an effective treatment option for patients with severe hypertriglyceridemia.

  7. A novel sodium N-fatty acyl amino acid surfactant using silkworm pupae as stock material

    NASA Astrophysics Data System (ADS)

    Wu, Min-Hui; Wan, Liang-Ze; Zhang, Yu-Qing

    2014-03-01

    A novel sodium N-fatty acyl amino acid (SFAAA) surfactant was synthesized using pupa oil and pupa protein hydrolysates (PPH) from a waste product of the silk industry. The aliphatic acids from pupa oil were modified into N-fatty acyl chlorides by thionyl chloride (SOCl2). SFAAA was synthesized using acyl chlorides and PPH. GC-MS analysis showed fatty acids from pupa oil consist mainly of unsaturated linolenic and linoleic acids and saturated palmitic and stearic acids. SFAAA had a low critical micelle concentration, great efficiency in lowering surface tension and strong adsorption at an air/water interface. SFAAA had a high emulsifying power, as well as a high foaming power. The emulsifying power of PPH and SFAAA in an oil/water emulsion was better with ethyl acetate as the oil phase compared to n-hexane. The environment-friendly surfactant made entirely from silkworm pupae could promote sustainable development of the silk industry.

  8. A novel sodium N-fatty acyl amino acid surfactant using silkworm pupae as stock material.

    PubMed

    Wu, Min-Hui; Wan, Liang-Ze; Zhang, Yu-Qing

    2014-03-21

    A novel sodium N-fatty acyl amino acid (SFAAA) surfactant was synthesized using pupa oil and pupa protein hydrolysates (PPH) from a waste product of the silk industry. The aliphatic acids from pupa oil were modified into N-fatty acyl chlorides by thionyl chloride (SOCl2). SFAAA was synthesized using acyl chlorides and PPH. GC-MS analysis showed fatty acids from pupa oil consist mainly of unsaturated linolenic and linoleic acids and saturated palmitic and stearic acids. SFAAA had a low critical micelle concentration, great efficiency in lowering surface tension and strong adsorption at an air/water interface. SFAAA had a high emulsifying power, as well as a high foaming power. The emulsifying power of PPH and SFAAA in an oil/water emulsion was better with ethyl acetate as the oil phase compared to n-hexane. The environment-friendly surfactant made entirely from silkworm pupae could promote sustainable development of the silk industry.

  9. Choice of solvent extraction technique affects fatty acid composition of pistachio (Pistacia vera L.) oil.

    PubMed

    Abdolshahi, Anna; Majd, Mojtaba Heydari; Rad, Javad Sharifi; Taheri, Mehrdad; Shabani, Aliakbar; Teixeira da Silva, Jaime A

    2015-04-01

    Pistachio (Pistacia vera L.) oil has important nutritional and therapeutic properties because of its high concentration of essential fatty acids. The extraction method used to obtain natural compounds from raw material is critical for product quality, in particular to protect nutritional value. This study compared the fatty acid composition of pistachio oil extracted by two conventional procedures, Soxhlet extraction and maceration, analyzed by a gas chromatography-flame ionization detector (GC-FID). Four solvents with different polarities were tested: n-hexane (Hx), dichloromethane (DCM), ethyl acetate (EtAc) and ethanol (EtOH). The highest unsaturated fatty acid content (88.493 %) was obtained by Soxhlet extraction with EtAc. The Soxhlet method extracted the most oleic and linolenic acids (51.99 % and 0.385 %, respectively) although a higher concentration (36.32 %) of linoleic acid was extracted by maceration.

  10. A novel sodium N-fatty acyl amino acid surfactant using silkworm pupae as stock material

    PubMed Central

    Wu, Min-Hui; Wan, Liang-Ze; Zhang, Yu-Qing

    2014-01-01

    A novel sodium N-fatty acyl amino acid (SFAAA) surfactant was synthesized using pupa oil and pupa protein hydrolysates (PPH) from a waste product of the silk industry. The aliphatic acids from pupa oil were modified into N-fatty acyl chlorides by thionyl chloride (SOCl2). SFAAA was synthesized using acyl chlorides and PPH. GC-MS analysis showed fatty acids from pupa oil consist mainly of unsaturated linolenic and linoleic acids and saturated palmitic and stearic acids. SFAAA had a low critical micelle concentration, great efficiency in lowering surface tension and strong adsorption at an air/water interface. SFAAA had a high emulsifying power, as well as a high foaming power. The emulsifying power of PPH and SFAAA in an oil/water emulsion was better with ethyl acetate as the oil phase compared to n-hexane. The environment-friendly surfactant made entirely from silkworm pupae could promote sustainable development of the silk industry. PMID:24651079

  11. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject to...

  12. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject to...

  13. 40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphonic acid, P- ethyl]-, bis(2... Specific Chemical Substances § 721.10243 Phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester. (a... phosphonic acid, P- ethyl]-, bis(2-chloroethyl) ester (PMN P-09-193; CAS No. 55088-28-3) is subject to...

  14. Probing fatty acid metabolism in bacteria, cyanobacteria, green microalgae and diatoms with natural and unnatural fatty acids.

    PubMed

    Beld, Joris; Abbriano, Raffaela; Finzel, Kara; Hildebrand, Mark; Burkart, Michael D

    2016-04-01

    In both eukaryotes and prokaryotes, fatty acid synthases are responsible for the biosynthesis of fatty acids in an iterative process, extending the fatty acid by two carbon units every cycle. Thus, odd numbered fatty acids are rarely found in nature. We tested whether representatives of diverse microbial phyla have the ability to incorporate odd-chain fatty acids as substrates for their fatty acid synthases and their downstream enzymes. We fed various odd and short chain fatty acids to the bacterium Escherichia coli, cyanobacterium Synechocystis sp. PCC 6803, green microalga Chlamydomonas reinhardtii and diatom Thalassiosira pseudonana. Major differences were observed, specifically in the ability among species to incorporate and elongate short chain fatty acids. We demonstrate that E. coli, C. reinhardtii, and T. pseudonana can produce longer fatty acid products from short chain precursors (C3 and C5), while Synechocystis sp. PCC 6803 lacks this ability. However, Synechocystis can incorporate and elongate longer chain fatty acids due to acyl-acyl carrier protein synthetase (AasS) activity, and knockout of this protein eliminates the ability to incorporate these fatty acids. In addition, expression of a characterized AasS from Vibrio harveyii confers a similar capability to E. coli. The ability to desaturate exogenously added fatty acids was only observed in Synechocystis and C. reinhardtii. We further probed fatty acid metabolism of these organisms by feeding desaturase inhibitors to test the specificity of long-chain fatty acid desaturases. In particular, supplementation with thia fatty acids can alter fatty acid profiles based on the location of the sulfur in the chain. We show that coupling sensitive gas chromatography mass spectrometry to supplementation of unnatural fatty acids can reveal major differences between fatty acid metabolism in various organisms. Often unnatural fatty acids have antibacterial or even therapeutic properties. Feeding of short

  15. Omega-3 fatty acids for cystic fibrosis.

    PubMed

    Oliver, Colleen; Watson, Helen

    2016-01-05

    Studies suggest that a diet rich in omega-3 essential fatty acids may have beneficial anti-inflammatory effects for chronic conditions such as cystic fibrosis. This is an updated version of a previously published review. To determine whether there is evidence that omega-3 polyunsaturated fatty acid supplementation reduces morbidity and mortality and to identify any adverse events associated with supplementation. We searched the Cochrane Cystic Fibrosis and Genetic Disorders Group's Trials Register comprising references identified from comprehensive electronic database searches and handsearches of relevant journals and abstract books of conference proceedings. Authors and persons interested in the subject of the review were contacted.Date of last search: 13 August 2013. Randomised controlled trials in people with cystic fibrosis comparing omega-3 fatty acid supplements with placebo. Two authors independently selected studies for inclusion, extracted data and assessed the risk of bias of the studies. The searches identified 15 studies; four studies with 91 participants (children and adults) were included; duration of studies ranged from six weeks to six months. Two studies were judged to be at low risk of bias based on adequate randomisation but this was unclear in the other two studies. Three of the studies adequately blinded patients, however, the risk of bias was unclear in all studies with regards to allocation concealment and selective reporting.Two studies compared omega-3 fatty acids to olive oil for six weeks. One study compared a liquid dietary supplement containing omega-3 fatty acids to one without for six months. One study compared omega-3 fatty acids and omega-6 fatty acids to a control (capsules with customised fatty acid blends) for three months. Only one short-term study (19 participants) comparing omega-3 to placebo reported a significant improvement in lung function and Shwachman score and a reduction in sputum volume in the omega-3 group. Another

  16. Fatty acid production in genetically modified cyanobacteria

    PubMed Central

    Liu, Xinyao; Sheng, Jie; Curtiss III, Roy

    2011-01-01

    To avoid costly biomass recovery in photosynthetic microbial biofuel production, we genetically modified cyanobacteria to produce and secrete fatty acids. Starting with introducing an acyl–acyl carrier protein thioesterase gene, we made six successive generations of genetic modifications of cyanobacterium Synechocystis sp. PCC6803 wild type (SD100). The fatty acid secretion yield was increased to 197 ± 14 mg/L of culture in one improved strain at a cell density of 1.0 × 109 cells/mL by adding codon-optimized thioesterase genes and weakening polar cell wall layers. Although these strains exhibited damaged cell membranes at low cell densities, they grew more rapidly at high cell densities in late exponential and stationary phase and exhibited less cell damage than cells in wild-type cultures. Our results suggest that fatty acid secreting cyanobacteria are a promising technology for renewable biofuel production. PMID:21482809

  17. Metabolic engineering of Saccharomyces cerevisiae for production of fatty acid-derived biofuels and chemicals.

    PubMed

    Runguphan, Weerawat; Keasling, Jay D

    2014-01-01

    As the serious effects of global climate change become apparent and access to fossil fuels becomes more limited, metabolic engineers and synthetic biologists are looking towards greener sources for transportation fuels. In recent years, microbial production of high-energy fuels by economically efficient bioprocesses has emerged as an attractive alternative to the traditional production of transportation fuels. Here, we engineered the budding yeast Saccharomyces cerevisiae to produce fatty acid-derived biofuels and chemicals from simple sugars. Specifically, we overexpressed all three fatty acid biosynthesis genes, namely acetyl-CoA carboxylase (ACC1), fatty acid synthase 1 (FAS1) and fatty acid synthase 2 (FAS2), in S. cerevisiae. When coupled to triacylglycerol (TAG) production, the engineered strain accumulated lipid to more than 17% of its dry cell weight, a four-fold improvement over the control strain. Understanding that TAG cannot be used directly as fuels, we also engineered S. cerevisiae to produce drop-in fuels and chemicals. Altering the terminal "converting enzyme" in the engineered strain led to the production of free fatty acids at a titer of approximately 400 mg/L, fatty alcohols at approximately 100mg/L and fatty acid ethyl esters (biodiesel) at approximately 5 mg/L directly from simple sugars. We envision that our approach will provide a scalable, controllable and economic route to this important class of chemicals. Copyright © 2013 International Metabolic Engineering Society. All rights reserved.

  18. Fatty Acid Compositions of Six Wild Edible Mushroom Species

    PubMed Central

    Günç Ergönül, Pelin; Akata, Ilgaz; Kalyoncu, Fatih; Ergönül, Bülent

    2013-01-01

    The fatty acids of six wild edible mushroom species (Boletus reticulatus, Flammulina velutipes var. velutipes, Lactarius salmonicolor, Pleurotus ostreatus, Polyporus squamosus, and Russula anthracina) collected from different regions from Anatolia were determined. The fatty acids were identified and quantified by gas chromatography and studied using fruit bodies. Fatty acid composition varied among species. The dominant fatty acid in fruit bodies of all mushrooms was cis-linoleic acid (18 : 2). Percentage of cis-linoleic acid in species varied from 22.39% to 65.29%. The other major fatty acids were, respectively, cis-oleic, palmitic, and stearic acids. Fatty acids analysis of the mushrooms showed that the unsaturated fatty acids were at higher concentrations than saturated fatty acids. PMID:23844377

  19. Lipid Class Specific Quantitative Analysis of n-3 Polyunsaturated Fatty Acids in Food Supplements.

    PubMed

    Kutzner, Laura; Ostermann, Annika I; Konrad, Thade; Riegel, Dieter; Hellhake, Stefan; Schuchardt, Jan Philipp; Schebb, Nils Helge

    2017-01-11

    Supplementation products containing n-3 PUFA from marine sources serve a large market. Although the amount of eicosapentaenoic acid and docosahexaenoic acid in the products is provided by the manufacturer, no or little information is available on their lipid pattern. Therefore, we quantitatively analyzed the fatty acid pattern in the lipid fractions triglycerides, phospholipids, ethyl esters, and free fatty acids in supplementation products by means of solid phase extraction and gas chromatography. Twelve products from the European and U.S. markets containing fish, krill, algal, or plant oil were analyzed. Total n-3 PUFA content ranged from 68 g/100 g fat (fish oil) to 42 g/100 g fat (algal oil) to 17 g/100 g fat (krill oil). On the basis of the n-3 PUFA containing lipid class, the supplements can be separated dominantly in ethyl ester, re-esterified triglyceride, triglyceride, and phospholipid containing products. Algae-based products contained natural triglycerides, krill oils a complex mixture of phospholipids, triglycerides, and free fatty acids, and fish oil products either ethyl esters, re-esterified triglycerides, or triglycerides. Even products of the same class and source showed distinct differences in their lipid pattern. A specification of the lipid composition of n-3 PUFA products would allow distinguishing the different (qualities of) supplements.

  20. SLC27 fatty acid transport proteins.

    PubMed

    Anderson, Courtney M; Stahl, Andreas

    2013-01-01

    The uptake and metabolism of long chain fatty acids (LCFA) are critical to many physiological and cellular processes. Aberrant accumulation or depletion of LCFA underlie the pathology of numerous metabolic diseases. Protein-mediated transport of LCFA has been proposed as the major mode of LCFA uptake and activation. Several proteins have been identified to be involved in LCFA uptake. This review focuses on the SLC27 family of fatty acid transport proteins, also known as FATPs, with an emphasis on the gain- and loss-of-function animal models that elucidate the functions of FATPs in vivo and how these transport proteins play a role in physiological and pathological situations.

  1. Trans fatty acids and fatty acid composition of mature breast milk in turkish women and their association with maternal diet's.

    PubMed

    Samur, Gülhan; Topcu, Ali; Turan, Semra

    2009-05-01

    The aim of this study was to determine the fatty acid composition and trans fatty acid and fatty acid contents of breast milk in Turkish women and to find the effect of breastfeeding mothers' diet on trans fatty acid and fatty acid composition. Mature milk samples obtained from 50 Turkish nursing women were analyzed. Total milk lipids extracts were transmethylated and analyzed by using gas liquid chromatography to determine fatty acids contents. A questionnaire was applied to observe eating habits and 3 days dietary records from mothers were obtained. Daily dietary intake of total energy and nutrients were estimated by using nutrient database. The mean total trans fatty acids contents was 2.13 +/- 1.03%. The major sources of trans fatty acids in mothers' diets were margarines-butter (37.0%), bakery products and confectionery (29.6%). Mothers who had high level of trans isomers in their milk consumed significantly higher amounts of these products. Saturated fatty acids, polyunsaturated fatty acids and monounsaturated fatty acids of human milk constituted 40.7 +/- 4.7%, 26.9 +/- 4.2% and 30.8 +/- 0.6% of the total fatty acids, respectively. The levels of fatty acids in human milk may reflect the current diet of the mother as well as the diet consumed early in pregnancy. Margarines, bakery products and confectionery are a major source of trans fatty acids in maternal diet in Turkey.

  2. Icosapent ethyl (eicosapentaenoic acid ethyl ester): Effects on remnant-like particle cholesterol from the MARINE and ANCHOR studies.

    PubMed

    Ballantyne, Christie M; Bays, Harold E; Philip, Sephy; Doyle, Ralph T; Braeckman, Rene A; Stirtan, William G; Soni, Paresh N; Juliano, Rebecca A

    2016-10-01

    Remnant-like particle cholesterol (RLP-C) is atherogenic and may increase atherosclerotic cardiovascular disease risk. Icosapent ethyl is a high-purity prescription eicosapentaenoic acid ethyl ester (approved as an adjunct to diet to reduce triglyceride [TG] levels in adult patients with TGs ≥500 mg/dL [≥5.65 mmol/L] at 4 g/day). In the MARINE and ANCHOR studies, icosapent ethyl reduced TG and other atherogenic lipid parameter levels without increasing low-density lipoprotein cholesterol (LDL-C) levels. This exploratory analysis evaluated the effects of icosapent ethyl on calculated and directly measured RLP-C. MARINE (TGs ≥500 and ≤2000 mg/dL [≥5.65 mmol/L and ≤22.6 mmol/L]) and ANCHOR (TGs ≥200 and <500 mg/dL [≥2.26 and <5.65 mmol/L] despite statin-controlled LDL-C) were phase 3, 12-week, double-blind studies that randomized adult patients to icosapent ethyl 4 g/day, 2 g/day, or placebo. This analysis assessed median percent change from baseline to study end in directly measured (immunoseparation assay) RLP-C levels (MARINE, n = 218; ANCHOR, n = 252) and calculated RLP-C levels in the full populations. Icosapent ethyl 4 g/day significantly reduced directly measured RLP-C levels -29.8% (p = 0.004) in MARINE and -25.8% (p = 0.0001) in ANCHOR versus placebo, and also reduced directly measured RLP-C levels to a greater extent in subgroups with higher versus lower baseline TG levels, in patients receiving statins versus no statins (MARINE), and in patients receiving medium/higher-intensity versus lower-intensity statins (ANCHOR). Strong correlations were found between calculated and directly measured RLP-C for baseline, end-of-treatment, and percent change values in ANCHOR and MARINE (0.73-0.92; p < 0.0001 for all). Icosapent ethyl 4 g/day significantly reduced calculated and directly measured RLP-C levels versus placebo in patients with elevated TG levels from the MARINE and ANCHOR studies. Copyright © 2016 The Authors

  3. 21 CFR 172.863 - Salts of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Salts of fatty acids. 172.863 Section 172.863 Food... Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely..., magnesium, potassium, and sodium salts of the fatty acids conforming with § 172.860 and/or oleic acid...

  4. 21 CFR 172.863 - Salts of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Salts of fatty acids. 172.863 Section 172.863 Food... Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely..., magnesium, potassium, and sodium salts of the fatty acids conforming with § 172.860 and/or oleic acid...

  5. 21 CFR 172.863 - Salts of fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Salts of fatty acids. 172.863 Section 172.863 Food... Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely..., magnesium, potassium, and sodium salts of the fatty acids conforming with § 172.860 and/or oleic acid...

  6. Production of Fatty Acid-Derived Valuable Chemicals in Synthetic Microbes

    PubMed Central

    Yu, Ai-Qun; Pratomo Juwono, Nina Kurniasih; Leong, Susanna Su Jan; Chang, Matthew Wook

    2014-01-01

    Fatty acid derivatives, such as hydroxy fatty acids, fatty alcohols, fatty acid methyl/ethyl esters, and fatty alka(e)nes, have a wide range of industrial applications including plastics, lubricants, and fuels. Currently, these chemicals are obtained mainly through chemical synthesis, which is complex and costly, and their availability from natural biological sources is extremely limited. Metabolic engineering of microorganisms has provided a platform for effective production of these valuable biochemicals. Notably, synthetic biology-based metabolic engineering strategies have been extensively applied to refactor microorganisms for improved biochemical production. Here, we reviewed: (i) the current status of metabolic engineering of microbes that produce fatty acid-derived valuable chemicals, and (ii) the recent progress of synthetic biology approaches that assist metabolic engineering, such as mRNA secondary structure engineering, sensor-regulator system, regulatable expression system, ultrasensitive input/output control system, and computer science-based design of complex gene circuits. Furthermore, key challenges and strategies were discussed. Finally, we concluded that synthetic biology provides useful metabolic engineering strategies for economically viable production of fatty acid-derived valuable chemicals in engineered microbes. PMID:25566540

  7. Production of Fatty Acid-derived valuable chemicals in synthetic microbes.

    PubMed

    Yu, Ai-Qun; Pratomo Juwono, Nina Kurniasih; Leong, Susanna Su Jan; Chang, Matthew Wook

    2014-01-01

    Fatty acid derivatives, such as hydroxy fatty acids, fatty alcohols, fatty acid methyl/ethyl esters, and fatty alka(e)nes, have a wide range of industrial applications including plastics, lubricants, and fuels. Currently, these chemicals are obtained mainly through chemical synthesis, which is complex and costly, and their availability from natural biological sources is extremely limited. Metabolic engineering of microorganisms has provided a platform for effective production of these valuable biochemicals. Notably, synthetic biology-based metabolic engineering strategies have been extensively applied to refactor microorganisms for improved biochemical production. Here, we reviewed: (i) the current status of metabolic engineering of microbes that produce fatty acid-derived valuable chemicals, and (ii) the recent progress of synthetic biology approaches that assist metabolic engineering, such as mRNA secondary structure engineering, sensor-regulator system, regulatable expression system, ultrasensitive input/output control system, and computer science-based design of complex gene circuits. Furthermore, key challenges and strategies were discussed. Finally, we concluded that synthetic biology provides useful metabolic engineering strategies for economically viable production of fatty acid-derived valuable chemicals in engineered microbes.

  8. The role of omega-3 fatty acids in mood disorders.

    PubMed

    Stahl, Lauren A; Begg, Denovan P; Weisinger, Richard S; Sinclair, Andrew J

    2008-01-01

    Research has established that docosahexaenoic acid (DHA), a long-chain omega-3 polyunsaturated fatty acid (PUFA), plays a fundamental role in brain structure and function. Epidemiological and cross-sectional studies have also identified a role for long-chain omega-3 PUFA, which includes DHA, eicosapentaenoic acid, and docosapentaenoic acid, in the etiology of depression. In the past ten years, there have been 12 intervention studies conducted using various preparations of longchain omega-3 PUFA in unipolar and bipolar depression. The majority of these studies administered long-chain omega-3 PUFA as an adjunct therapy. The studies have been conducted over 4 to 16 weeks of intervention and have often included small cohorts. In four out of the seven studies conducted in depressed individuals and in two out of the five studies in bipolar patients, individuals have reported a positive outcome following supplementation with ethyl-eicosapentaenoic acid or fish oil containing long-chain omega-3 PUFA. In the three trials that researched the influence of DHA-rich preparations, no significant effects were reported. The mechanisms that have been invoked to account for the benefits of long-chain omega-3 PUFA in depression include reductions in prostaglandins derived from arachidonic acid, which lead to decreased brain-derived neurotrophic factor levels and/or alterations in blood flow to the brain.

  9. Fatty Acids as Surfactants on Aerosol Particles

    NASA Astrophysics Data System (ADS)

    Tervahattu, H.; Juhanoja, J.; Niemi, J.

    2003-12-01

    Fatty acids (n-alcanoic acids) are common compounds in numerous anthropogenic and natural emissions. According to Rogge et al. (1993), catalyst-equipped automobiles emitted more than 600 μg km-1 of fatty acids which was over 50% of all identified organics in fine aerosol emissions. Coal burning produces fatty acids ranging from about 1700 mg kg-1 for bituminous coal to over 10000 mg kg-1 for lignite (Oros and Simoneit, 2000). Similarly, biomass burning is an important source for aerosol fatty acids. They are the major identified compound group in deciduous tree smoke, their total emission factor being measured as 1589 mg kg-1 which was 56% of all identified organic compounds (Oros and Simoneit, 2001a). Large amounts of fatty acid are also emitted from burning of conifer trees and grass (Oros and Simoneit, 2001a; Simoneit, 2002). Fatty acids have been reported to be major constituents of marine aerosols in many investigations (Barger and Garrett, 1976; Gagosian et. al, 1981; Sicre et al., 1990; Stephanou, 1992). It has been suggested that as the marine aerosol particles form, they acquire a coating of organic surfactants (Blanchard, 1964; Gill et al., 1983; Middlebrook et al., 1998; Ellison et al., 1999). Amphiphilic molecules, including lipids, can be assembled as monomolecular layers at air/water interfaces as well as transported to a solid support. Recently, we could show by time-of-flight secondary ion mass spectrometry that fatty acids are important ingredients of the outermost surface layer of the sea-salt aerosol particles (Tervahattu et al., 2002). In their TOF-SIMS studies on the surface composition of atmospheric aerosols, Peterson and Tyler (2002) found fatty acids on the surface of Montana forest fire particles. In this work we have studied by TOF-SIMS the surface chemical composition of aerosol particles emitted from field fires in the Baltic and other East European countries and transported to Finland as well as aerosol particles transported from

  10. Acute effects of dietary fatty acids on the fatty acids of human milk.

    PubMed

    Francois, C A; Connor, S L; Wander, R C; Connor, W E

    1998-02-01

    Although it is known that the fatty acid profile of human milk is altered by diet, the rapidity with which this occurs has not been addressed. We hypothesized that after absorption the fatty acids of a given meal would be transferred rapidly from the chylomicrons of the blood into human milk. Fourteen lactating women drank six test formulas, each containing a different fat: menhaden oil, herring oil, safflower oil, canola oil, coconut oil, or cocoa butter. The subjects collected a midfeeding milk sample before consuming the breakfast test formula and additional samples at 6, 10, 14, and 24 h and then once daily for 4-7 d. Fatty acids of special interest included eicosapentaenoic and docosahexaenoic acids from menhaden oil, cetoleic acid from herring oil, linoleic acid from safflower oil, linolenic acid from canola oil, lauric acid from coconut oil, and palmitic and stearic acids from cocoa butter. Each of these fatty acids increased significantly in human milk within 6 h of consumption of the test formulas (P < 0.001). Maximum increases occurred 10 h after safflower oil; 14 h after cocoa utter, coconut oil, canola oil, and menhaden oil (eicosapentaenoic acid); and 24 h after herring oil and menhaden oil (docosahexaenoic acid). All of these fatty acids remained significantly elevated in milk (P < 0.05) for 10-24 h, except for docosahexaenoic acid, which remained significantly elevated for 2 d, and eicosapentaenoic acid, which remained elevated for 3 d. These data support the hypothesis that there is a rapid transfer of dietary fatty acids from chylomicrons into human milk.

  11. Polyunsaturated fatty acids in emerging psychosis.

    PubMed

    Mossaheb, Nilufar; Schloegelhofer, Monika; Schaefer, Miriam R; Fusar-Poli, Paolo; Smesny, Stefan; McGorry, Pat; Berger, Gregor; Amminger, G Paul

    2012-01-01

    The role of polyunsaturated fatty acids and their metabolites for the cause and treatment of psychotic disorders are widely discussed. The efficacy as an augmenting agent in chronic schizophrenia seems to be small or not present, however epidemiological data, as well as some recent controlled studies in emerging psychosis point towards possible preventive effects of long-chain polyunsaturated fatty acids in early and very early stages of psychotic disorders and some potential secondary or tertiary beneficial long-term effects in later, more chronic stages, in particular for metabolic or extra-pyramidal side effects. In this comprehensive review, we describe the physiology and metabolism of polyunsaturated fatty acids, phospholipases, epidemiological evidence and the effect of these fatty acids on the brain and neurodevelopment. Furthermore, we examine the available evidence in indicated prevention in emerging psychosis, monotherapy, add-on therapy and tolerability. The neuroprotective potential of n-3 LC-PUFAs for indicated prevention, i.e. delaying transition to psychosis in high-risk populations needs to be further explored.

  12. Lipid and Fatty Acid Requirements of Tilapia

    USDA-ARS?s Scientific Manuscript database

    Dietary lipids are an important source of highly digestible energy and are the only source of essential fatty acids required for normal growth and development. They are also carriers and assist in the absorption of fat-soluble nutrients, such as sterols and fat-soluble vitamins, serve as a source of...

  13. Hydroxyl Fatty Acids and Hydroxyl Oils

    USDA-ARS?s Scientific Manuscript database

    Soybean oil is produced domestically in large supply, averaging over 20 billion pounds per year with an annual carryover of more than one billion pounds. It is important to find new uses for this surplus soybean oil. Hydroxyl fatty acids and hydroxyl oils are platform materials for specialty chemi...

  14. [THE FATTY ACIDS AND RELATIONSHIP WITH HEALTH].

    PubMed

    Sanhueza Catalán, Julio; Durán Agüero, Samuel; Torres García, Jairo

    2015-09-01

    The functionality of the eukaryotic cell depends on the cell membrane, the genetic information and action of different organelles with or without the presence of membranes. The functionality of the cell membrane and organelles containing it depends primarily on the type and location of fatty acids in the phospholipids and the type of enzymes associated with them, this allows the fatty acids to be metabolized to new species that exert various functions. From this perspective, some essential fatty acids (EFAs) that produce metabolites that exert health benefits are identified, (for example antiinflammatory, neuroprotection, etc) and exert negative effects metabolites (eg inflammation, necrosis promoters, atheroma, etc.) are also generated. In general, these adverse or beneficial effects depend on the ratio of omega-6/omega-3 obtained in the diet. Thus, the higher this ratio is more negative effect; therefore the challenge of the current supply is obtained through food consumption, lower ratios in these fatty acids. The present review aims to present recent evidence on the effects of some AGEs, and the role of diet in maintaining health.

  15. Fatty acid biosynthesis in pea root plastids

    SciTech Connect

    Stahl, R.J.; Sparace, S.A. )

    1989-04-01

    Fatty acid biosynthesis from (1-{sup 14}C)acetate was optimized in plastids isolated from primary root tips of 7-day-old germinating pea seeds. Fatty acid synthesis was maximum at approximately 80 nmoles/hr/mg protein in the presence of 200 {mu}M acetate, 0.5 mM each of NADH, NADPH and CoA, 6 mM each of ATP and MgCl{sub 2}, 1 mM each of the MnCl{sub 2} and glycerol-3-phosphate, 15 mM KHCO{sub 3}, and 0.1M Bis-tris-propane, pH 8.0 incubated at 35C. At the standard incubation temperature of 25C, fatty acid synthesis was linear from up to 6 hours with 80 to 100 {mu}g/mL plastid protein. ATP and CoA were absolute requirements, whereas KHCO{sub 3}, divalent cations and reduced nucleotides all improved activity by 80 to 85%. Mg{sup 2+} and NADH were the preferred cation and nucleotide, respectively. Dithiothreitol and detergents were generally inhibitory. The radioactive products of fatty acid biosynthesis were approximately 33% 16:0, 10% 18:0 and 56% 18:1 and generally did not vary with increasing concentrations of each cofactor.

  16. Melting of saturated fatty acid zinc soaps.

    PubMed

    Barman, S; Vasudevan, S

    2006-11-16

    The melting of alkyl chains in the saturated fatty acid zinc soaps of different chain lengths, Zn(C(n)H(2n+1)COO)(2); n = 11, 13, 15, and 17, have been investigated by powder X-ray diffraction, differential scanning calorimetry, and vibrational spectroscopy. These compounds have a layer structure with the alkyl chains arranged as tilted bilayers and with all methylene chains adopting a planar, all-trans conformation at room temperature. The saturated fatty acid zinc soaps exhibit a single reversible melting transition with the associated enthalpy change varying linearly with alkyl chain length, but surprisingly, the melting temperature remaining constant. Melting is associated with changes in the conformation of the alkyl chains and in the nature of coordination of the fatty acid to zinc. By monitoring features in the infrared spectra that are characteristic of the global conformation of the alkyl chains, a quantitative relation between conformational disorder and melting is established. It is found that, irrespective of the alkyl chain length, melting occurs when 30% of the chains in the soap are disordered. These results highlight the universal nature of the melting of saturated fatty acid zinc soaps and provide a simple explanation for the observed phenomena.

  17. Fatty acid composition of California grown almonds.

    PubMed

    Sathe, S K; Seeram, N P; Kshirsagar, H H; Heber, D; Lapsley, K A

    2008-11-01

    Eight almond (Prunus dulcis L.) cultivars from 12 different California counties, collected during crop years 2004 to 2005 and 2005 to 2006, were extracted with petroleum ether. The extracts were subjected to GC-MS analyses to determine fatty acid composition of soluble lipids. Results indicated palmitic (C16:0), oleic (C18:1), linoleic (C18:2), and alpha-linolenic (C18:3) acid, respectively, accounted for 5.07% to 6.78%, 57.54% to 73.94%, 19.32% to 35.18%, and 0.04% to 0.10%; of the total lipids. Oleic and linoleic acid were inversely correlated (r=-0.99, P= 0.05) and together accounted for 91.16% to 94.29% of the total soluble lipids. Statistically, fatty acid composition was significantly affected by cultivar and county.

  18. Comparative analysis of the efficacy of omega-3 fatty acids for hypertriglyceridaemia management in Korea.

    PubMed

    Kim, H-S; Kim, H; Jeong, Y J; Yang, S J; Baik, S J; Lee, H; Lee, S-H; Cho, J H; Choi, I-Y; Yim, H W; Yoon, K-H

    2016-10-01

    This study aimed to compare the ability of statin monotherapy (ST group), omega-3 fatty acid monotherapy (OM_A group) and combination therapy with omega-3 fatty acids and a statin (OM_S group), to reduce triglyceride (TG) levels in patients with hypertriglyceridaemia. In this retrospective cohort study, we extracted data from the electronic medical records of patients initially prescribed either a statin or omega-3 fatty acids between January, 2009 and December, 2013. We performed a comparative analysis of the change in cholesterol levels between baseline and an average of 3 months later. Data were extracted for 2071 patients. The average daily eicosapentaenoic acid (EPA) ethyl ester and docosahexaenoic acid (DHA) ethyl ester intake was 1689 mg, and 79-86% of the OM_A and OM_S groups were prescribed two omega-3 fatty acid capsules. At a baseline TG level of between 200 and 500 mg/dL, TG levels were reduced by 16 ± 2·8% in the ST group, 28 ± 2·8% in the OM_A group and 29 ± 2·3% in the OM_S group (P = 0·001 for ST group vs. OM_A and OM_S groups), with no difference between the OM_A and OM_S groups. At a baseline TG level ≥500 mg/dL, there was no difference in TG level reduction between the three groups (54 ± 7·3%, 55·8 ± 3·5% and 51·8 ± 6·8%, respectively, P = 0·851). Although omega-3 fatty acids are not considered the primary medication for hypertriglyceridaemia, the prescription of omega-3 fatty acids is justifiable if reduction in TG levels is judged to be necessary. © 2016 John Wiley & Sons Ltd.

  19. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks

    DOEpatents

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.; Beltran, Leslie V.; Kunz, Linda A.; Pals, Tessa M.; Quinn, Jordan R; Behrends, Jr., Raymond T.; Bernhardt, Randal J.

    2016-07-05

    Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

  20. Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I.

    PubMed

    Boshoff, Helena I; Mizrahi, Valerie; Barry, Clifton E

    2002-04-01

    The effects of low extracellular pH and intracellular accumulation of weak organic acids were compared with respect to fatty acid synthesis by whole cells of Mycobacterium tuberculosis and Mycobacterium smegmatis. The profile of fatty acids synthesized during exposure to benzoic, nicotinic, or pyrazinoic acids, as well as that observed during intracellular hydrolysis of the corresponding amides, was not a direct consequence of modulation of fatty acid synthesis by these compounds but reflected the response to inorganic acid stress. Analysis of fatty acid synthesis in crude mycobacterial cell extracts demonstrated that pyrazinoic acid failed to directly modulate the fatty acid synthase activity catalyzed by fatty acid synthase I (FAS-I). However, fatty acid synthesis was irreversibly inhibited by 5-chloro-pyrazinamide in a time-dependent fashion. Moreover, we demonstrate that pyrazinoic acid does not inhibit purified mycobacterial FAS-I, suggesting that this enzyme is not the immediate target of pyrazinamide.

  1. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0) is...

  2. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject to...

  3. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject...

  4. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0)...

  5. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0)...

  6. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-dimethylcyclohexyl)ethyl ester. 721.10074 Section 721.10074 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0)...

  7. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject...

  8. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject...

  9. 40 CFR 721.1950 - 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester .

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-oxopropenyloxy)ethyl) ester . 721.1950 Section 721.1950 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1950 2-Butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester . (a... 2-butenedioic acid (Z), mono(2-((1-oxopropenyloxy)ethyl) ester (PMN P-85-543) is subject...

  10. Fatty acid biosynthesis revisited: Structure elucidation and metabolic engineering

    SciTech Connect

    Beld, Joris; Lee, D. John; Burkart, Michael D.

    2014-10-20

    Fatty acids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fatty acid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fatty acid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fatty acid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fatty acids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fatty acid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fatty acid synthases' many intricate structural and regulatory elements. Lastly, in this review, we summarize each enzymatic domain and discuss efforts to engineer fatty acid synthases, providing some clues to important challenges and opportunities in the field.

  11. Fatty acid biosynthesis revisited: structure elucidation and metabolic engineering.

    PubMed

    Beld, Joris; Lee, D John; Burkart, Michael D

    2015-01-01

    Fatty acids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fatty acid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fatty acid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fatty acid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fatty acids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fatty acid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fatty acid synthases' many intricate structural and regulatory elements. In this review, we summarize each enzymatic domain and discuss efforts to engineer fatty acid synthases, providing some clues to important challenges and opportunities in the field.

  12. Fatty Acid Biosynthesis Revisited: Structure Elucidation and Metabolic Engineering

    PubMed Central

    Beld, Joris; Lee, D. John

    2014-01-01

    Fatty acids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fatty acid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fatty acid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fatty acid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fatty acids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fatty acid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fatty acid synthases’ many intricate structural and regulatory elements. In this review, we summarize each enzymatic domain and discuss efforts to engineer fatty acid synthases, providing some clues to important challenges and opportunities in the field. PMID:25360565

  13. Yarrowia lipolytica lipase Lip2: an efficient enzyme for the production of concentrates of docosahexaenoic acid ethyl ester.

    PubMed

    Casas-Godoy, Leticia; Meunchan, Muchalin; Cot, Marlène; Duquesne, Sophie; Bordes, Florence; Marty, Alain

    2014-06-20

    The production of Omega-3 (ω-3) polyunsaturated fatty acids (PUFAs) rich in cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) was studied using lipase-catalysed hydrolysis of a mixture of ethyl esters from tuna oil. Lipases from Yarrowia lipolytica (YLL2), Thermomyces lanuginosus (TLL) and Candida rugosa (CRL1, CRL3 and CRL4) were tested. C. rugosa lipases discriminated esters on the basis of their chain length, with less affinity for γ-linolenate, 11-eicosenoate, arachidonate, EPA, DPA and DHA ethyl esters. However, YLL2 and TLL improved discrimination towards DHA, as enzyme selectivity was shown to be mainly based on the position of the double bond closest to the carboxylic group. From the point of view of kinetics, purity and yield, YLL2 was the most effective lipase for DHA purification. Using this enzyme in an open reactor process resulted in the highest concentrations of DHA ethyl ester (77%) and ω-3 esters (81%) with a recovery of 94% and 77% respectively. Copyright © 2014. Published by Elsevier B.V.

  14. Novel fatty acid esters of p-coumaryl alcohol in epicuticular wax of apple fruit.

    PubMed

    Whitaker, B D; Schmidt, W F; Kirk, M C; Barnes, S

    2001-08-01

    Hexane extracts of epicuticular wax from cv. Gala apples were noted to have an unusual, broad absorbance maximum at approximately 258 nm, which led us to isolate and identify the primary UV-absorbing compounds. Column and thin-layer chromatography yielded a fraction that gave a series of paired, 260-nm-absorbing peaks on C(18) HPLC. These were shown to be a family of phenolic fatty acid esters, for which retention times increased with increasing fatty acid chain length, and paired peaks were esters of two related phenolics with the same fatty acid moiety. Alkaline hydrolysis of the esters released two water-soluble phenolics separable by C(18) HPLC. Electrospray ionization mass spectrometry gave a molecular mass of 150 for both, and (1)H NMR plus UV absorbance spectra identified them as E and Z isomers of p-coumaryl alcohol. Alkaline cleavage of the fatty acid esters in the presence of methanol or ethanol resulted in partial derivatization of E-p-coumaryl alcohol to the corresponding gamma-O-methyl or O-ethyl ether. Gradient HMQC NMR of the HPLC-purified stearate ester of E-p-coumaryl alcohol indicated that fatty acid esterification occurs at the gamma-OH rather than at the 4-OH on the phenyl ring. This is the first report of fatty acid esters of monolignols as a natural plant product.

  15. Effects of the addition of dimer acid alkyl esters on the properties of ethyl cellulose.

    PubMed

    Lee, Sangjun; Ko, Kwang-Hwan; Shin, Jihoon; Kim, Nam-Kyun; Kim, Young-Wun; Kim, Joon-Seop

    2015-05-05

    In this study, we synthesized dimer acid (DA) esters, having short to long alkyl chains, (DA-Cn) by the Diels-Alder reaction and subsequent esterification reaction of fatty acids that were prepared by the hydrolysis of waste vegetable oil. It was found that the DA-Cn were thermally more stable than common petroleum-based plasticizer DOP. When the DOP, DA, or DA-Cn with short alkyl chains were added to ethyl cellulose (EC), the optical clarity and SEM images of the samples showed their good miscibility with those additives in a micro-scale. It was also found that the rubbery modulus of the EC decreased with increasing amount of additives; the type of the additives did not affect the rates of the decrease in the rubbery modulus. The main transition temperatures of the EC containing either DA or DA-C1 or DA-C4 decreased with increasing amounts of those additives and were comparable to that of the DOP-containing EC. The above findings suggested that the DA and its esters with short alkyl chains could act as effective plasticizer and, thus, could be used instead of the DOP. In addition, the results obtained from tensile testing and leaching experiments implied that the DA might be better plasticizer than the DA-C1 and DA-C4, at least in some cases, because of hydrogen-bonding with the EC.

  16. Fatty acid production from amino acids and alpha-keto acids by Brevibacterium linens BL2.

    PubMed

    Ganesan, Balasubramanian; Seefeldt, Kimberly; Weimer, Bart C

    2004-11-01

    Low concentrations of branched-chain fatty acids, such as isobutyric and isovaleric acids, develop during the ripening of hard cheeses and contribute to the beneficial flavor profile. Catabolism of amino acids, such as branched-chain amino acids, by bacteria via aminotransferase reactions and alpha-keto acids is one mechanism to generate these flavorful compounds; however, metabolism of alpha-keto acids to flavor-associated compounds is controversial. The objective of this study was to determine the ability of Brevibacterium linens BL2 to produce fatty acids from amino acids and alpha-keto acids and determine the occurrence of the likely genes in the draft genome sequence. BL2 catabolized amino acids to fatty acids only under carbohydrate starvation conditions. The primary fatty acid end products from leucine were isovaleric acid, acetic acid, and propionic acid. In contrast, logarithmic-phase cells of BL2 produced fatty acids from alpha-keto acids only. BL2 also converted alpha-keto acids to branched-chain fatty acids after carbohydrate starvation was achieved. At least 100 genes are potentially involved in five different metabolic pathways. The genome of B. linens ATCC 9174 contained these genes for production and degradation of fatty acids. These data indicate that brevibacteria have the ability to produce fatty acids from amino and alpha-keto acids and that carbon metabolism is important in regulating this event.

  17. Manipulation of Galactolipid Fatty Acid Composition with Substituted Pyridazinones

    PubMed Central

    John, Judith B. St.

    1976-01-01

    The fatty acid composition of the major lipids of the chloroplast membranes, the mono- and digalactosyl diglycerides, can be definably altered with various substituted pyridazinones. Galactolipid fatty acid composition of wheat (Triticum aestivum L.) can be altered so that there is a decrease in linolenic acid accompanied by an increase in linoleic acid without a shift in the relative proportion of saturated to unsaturated fatty acids; the fatty acid composition can be shifted toward a higher proportion of saturated fatty acids; or the fatty acid composition of the monogalactosyl diglycerides can be altered in preference to the digalactosyl diglycerides. Also, the light-mediated parallel accumulation of chlorophyll and linolenic acid can be separated with a substituted pyridazinone. The substituted pyridazinones may be useful tools in clarifying the role the galactolipids and their component fatty acids play in the structure and function of chloroplast membranes in higher plants. PMID:16659420

  18. 21 CFR 172.863 - Salts of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Salts of fatty acids. 172.863 Section 172.863 Food... Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely..., magnesium, potassium, and sodium salts of the fatty acids conforming with § 172.860 and/or oleic...

  19. 40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur dioxide and... dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty...

  20. 40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur dioxide and... dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty...

  1. 40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur dioxide and... dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty...

  2. 40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur dioxide and... dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty...

  3. 40 CFR 721.9672 - Amides, tall-oil fatty, N-[2-[2-hydroxyethyl)amino]ethyl], reaction products with sulfur dioxide...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...], reaction products with sulfur dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty acids, tall-oil reaction products with sulfur dioxide and... dioxide; fatty acids, tall-oil, reaction products with 1-piperazineethanamine and sulfur dioxide; fatty...

  4. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Lactylic esters of fatty acids. 172.848 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty acids may be safely used in food in accordance with the following prescribed conditions: (a) They...

  5. 40 CFR 721.10320 - Fatty acid amide (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid amide (generic). 721.10320... Substances § 721.10320 Fatty acid amide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amide (PMN P-03-186) is subject...

  6. 40 CFR 721.3627 - Branched synthetic fatty acid.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Branched synthetic fatty acid. 721... Substances § 721.3627 Branched synthetic fatty acid. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a branched synthetic fatty acid...

  7. 75 FR 14082 - Ammonium Salts of Fatty Acids (C8

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-03-24

    ... AGENCY 40 CFR Part 180 Ammonium Salts of Fatty Acids (C 8 -C 18 Saturated); Exemption from the... fatty acids (C 8 -C 18 saturated) applied pre- and post-harvest on all raw agricultural commodities when... eliminates the need to establish a maximum permissible level for residues of ammonium salts of fatty acids (C...

  8. 40 CFR 721.10463 - Fatty acid amides (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid amides (generic). 721.10463... Substances § 721.10463 Fatty acid amides (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amides (PMN P-03-388...

  9. 40 CFR 721.3627 - Branched synthetic fatty acid.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Branched synthetic fatty acid. 721... Substances § 721.3627 Branched synthetic fatty acid. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a branched synthetic fatty acid...

  10. 40 CFR 721.3627 - Branched synthetic fatty acid.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Branched synthetic fatty acid. 721... Substances § 721.3627 Branched synthetic fatty acid. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a branched synthetic fatty acid...

  11. 40 CFR 721.3710 - Polyether modified fatty acids (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Polyether modified fatty acids... Specific Chemical Substances § 721.3710 Polyether modified fatty acids (generic). (a) Chemical substance... Polyether modified fatty acids (PMN P-99-0435) is subject to reporting under this section for the...

  12. 40 CFR 721.3710 - Polyether modified fatty acids (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Polyether modified fatty acids... Specific Chemical Substances § 721.3710 Polyether modified fatty acids (generic). (a) Chemical substance... Polyether modified fatty acids (PMN P-99-0435) is subject to reporting under this section for the...

  13. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... approved emulsifiers in dry, whipped topping base. The fatty acids used in the production of the... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Polyglycerol esters of fatty acids. 172.854... HUMAN CONSUMPTION Multipurpose Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol...

  14. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... approved emulsifiers in dry, whipped topping base. The fatty acids used in the production of the... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Polyglycerol esters of fatty acids. 172.854... HUMAN CONSUMPTION Multipurpose Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol...

  15. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... approved emulsifiers in dry, whipped topping base. The fatty acids used in the production of the... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Polyglycerol esters of fatty acids. 172.854... HUMAN CONSUMPTION Multipurpose Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol...

  16. Naturally occurring fatty acids: Source, chemistry, and uses

    USDA-ARS?s Scientific Manuscript database

    Natural occurring fatty acids are a large and complex class of compounds found in plants and animals. Fatty acids are abundant and of interest because of their renewability, biodegradability, biocompatibility, low cost, and fascinating chemistry. Of the many fatty acids, only 20-25 of them are widel...

  17. Bioconverted Products of Essential Fatty Acids as Potential Antimicrobial Agents

    USDA-ARS?s Scientific Manuscript database

    This review deals with the recent findings on the microbial conversion of essential fatty acids (EFAs) through Pseudomonas aeruginosa PR3 NRRL-B-18602, and the antimicrobial properties of bioconverted essential fatty acids, with particular emphasis on n-3 or n-6 fatty acids. The first section deals...

  18. 40 CFR 721.10691 - Fatty acid amide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amide (generic). 721.10691... Substances § 721.10691 Fatty acid amide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amide (PMN P-13-267) is...

  19. 40 CFR 721.10320 - Fatty acid amide (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acid amide (generic). 721.10320... Substances § 721.10320 Fatty acid amide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amide (PMN P-03-186) is...

  20. 40 CFR 721.10520 - Acetylated fatty acid glycerides (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acetylated fatty acid glycerides... Specific Chemical Substances § 721.10520 Acetylated fatty acid glycerides (generic). (a) Chemical substance... acetylated fatty acid glycerides (PMN P-11-160) is subject to reporting under this section for...

  1. 40 CFR 721.10520 - Acetylated fatty acid glycerides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acetylated fatty acid glycerides... Specific Chemical Substances § 721.10520 Acetylated fatty acid glycerides (generic). (a) Chemical substance... acetylated fatty acid glycerides (PMN P-11-160) is subject to reporting under this section for...

  2. 40 CFR 721.3710 - Polyether modified fatty acids (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Polyether modified fatty acids... Specific Chemical Substances § 721.3710 Polyether modified fatty acids (generic). (a) Chemical substance... Polyether modified fatty acids (PMN P-99-0435) is subject to reporting under this section for...

  3. 40 CFR 721.3710 - Polyether modified fatty acids (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Polyether modified fatty acids... Specific Chemical Substances § 721.3710 Polyether modified fatty acids (generic). (a) Chemical substance... Polyether modified fatty acids (PMN P-99-0435) is subject to reporting under this section for...

  4. 40 CFR 721.10463 - Fatty acid amides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amides (generic). 721.10463... Substances § 721.10463 Fatty acid amides (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amides (PMN...

  5. 40 CFR 721.10687 - Fatty acid amide hydrochlorides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amide hydrochlorides... Specific Chemical Substances § 721.10687 Fatty acid amide hydrochlorides (generic). (a) Chemical substance... fatty acid amide hydrochlorides (PMNs P-13-201, P-13-203, P-13-204, P-13-205, P-13-206, P-13-207,...

  6. 40 CFR 721.10680 - Fatty acid amides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amides (generic). 721.10680... Substances § 721.10680 Fatty acid amides (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as fatty acid amides (PMNs...

  7. 40 CFR 721.10320 - Fatty acid amide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amide (generic). 721.10320... Substances § 721.10320 Fatty acid amide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amide (PMN P-03-186) is...

  8. 40 CFR 721.3710 - Polyether modified fatty acids (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Polyether modified fatty acids... Specific Chemical Substances § 721.3710 Polyether modified fatty acids (generic). (a) Chemical substance... Polyether modified fatty acids (PMN P-99-0435) is subject to reporting under this section for...

  9. [CONTENT OF TRANS FATTY ACIDS IN FOOD PRODUCTS IN SPAIN].

    PubMed

    Robledo de Dios, Teresa; Dal Re Saavedra, M Ángeles; Villar Villalba, Carmen; Pérez-Farinós, Napoleón

    2015-09-01

    trans fatty acids are associated to several health disorders, as ischemic heart disease or diabetes mellitus. to assess the content of trans fatty acids in products in Spain, and the percentage of trans fatty acids respecting total fatty acids. 443 food products were acquired in Spain, and they were classified into groups. The content in fatty acids was analyzed using gas chromatography. Estimates of central tendency and variability of the content of trans fatty acids in each food group were computed (in g of trans fatty acids/100 g of product). The percentage of trans fatty acids respecting total fatty acids was calculated in each group. 443 products were grouped into 42 groups. Median of trans fatty acids was less than 0.55 g / 100 g of product in all groups except one. 83 % of groups had less than 2 % of trans fatty acids, and 71 % of groups had less than 1 %. the content of trans fatty acids in Spain is low, and it currently doesn't play a public health problem. Copyright AULA MEDICA EDICIONES 2014. Published by AULA MEDICA. All rights reserved.

  10. Maze solving using fatty acid chemistry.

    PubMed

    Suzuno, Kohta; Ueyama, Daishin; Branicki, Michal; Tóth, Rita; Braun, Artur; Lagzi, István

    2014-08-12

    This study demonstrates that the Marangoni flow in a channel network can solve maze problems such as exploring and visualizing the shortest path and finding all possible solutions in a parallel fashion. The Marangoni flow is generated by the pH gradient in a maze filled with an alkaline solution of a fatty acid by introducing a hydrogel block soaked with an acid at the exit. The pH gradient changes the protonation rate of fatty acid molecules, which translates into the surface tension gradient at the liquid-air interface through the maze. Fluid flow maintained by the surface tension gradient (Marangoni flow) can drag water-soluble dye particles toward low pH (exit) at the liquid-air interface. Dye particles placed at the entrance of the maze dissolve during this motion, thus exhibiting and finding the shortest path and all possible paths in a maze.

  11. Isoprenoid quinones and fatty acids of Zoogloea.

    PubMed

    Hiraishi, A; Shin, Y K; Sugiyama, J; Komagata, K

    1992-04-01

    Nine Zoogloea strains including the type strain of Z. ramigera (IAM 12136 = ATCC 19544 = N.C. Dondero 106) and newly isolated strains were investigated for isoprenoid quinone composition and whole-cell fatty acid profiles. Seven of the tested strains, having phenotypic properties typical of Zoogloea, were characterized by their production of both ubiquinone-8 and rhodoquinone-8 as major quinones, whereas the remaining two strains, Z. ramigera IAM 12669 (= K. Crabtree I-16-M) and IAM 12670 (= P.R. Dugan 115), formed ubiquinone-10 and ubiquinone-8, respectively, as the sole quinone. All rhodoquinone-producing strains contained palmitoleic acid and 3-hydroxy-decanoic acid as the major components of nonpolar and hydroxylated fatty acids, respectively. Marked differences were noted in the fatty acid composition between the strains with and without rhodoquinones. The chemotaxonomic data suggested that the rhodoquinone-lacking strains should be excluded from the genus Zoogloea. Since there have been no reliable taxonomic tools for Zoogloea, rhodoquinone analysis may provide a new criterion of great promise for identifying Zoogloea strains.

  12. High-yield synthesis of bioactive ethyl cinnamate by enzymatic esterification of cinnamic acid.

    PubMed

    Wang, Yun; Zhang, Dong-Hao; Zhang, Jiang-Yan; Chen, Na; Zhi, Gao-Ying

    2016-01-01

    In this paper, Lipozyme TLIM-catalyzed synthesis of ethyl cinnamate through esterification of cinnamic acid with ethanol was studied. In order to increase the yield of ethyl cinnamate, several media, including acetone, isooctane, DMSO and solvent-free medium, were investigated in this reaction. The reaction showed a high yield by using isooctane as reaction medium, which was found to be much higher than the yields reported previously. Furthermore, several parameters such as shaking rate, water activity, reaction temperature, substrate molar ratio and enzyme loading had important influences on this reaction. For instance, when temperature increased from 10 to 50 °C, the initial reaction rate increased by 18 times and the yield of ethyl cinnamate increased by 6.2 times. Under the optimum conditions, lipase-catalyzed synthesis of ethyl cinnamate gave a maximum yield of 99%, which was of general interest for developing industrial processes for the preparation of ethyl cinnamate.

  13. Fatty acid facts, Part I. Essential fatty acids as treatment for depression, or food for mood?

    PubMed

    Pawels, E K J; Volterrani, D

    2008-10-01

    The epidemic character of depressive disorders has prompted further research into dietary habits that could make an etiological contribution. One clear change in the diet of the population in developed countries has been the replacement of omega-3 polyunsaturated fatty acids by saturated fats and trans-fats as well as by omega-6 polyunsaturated fatty acids. Omega-3 and omega-6 fatty acids are essential fatty acids, and the members of the -3 and -6 series are crucial for human health. In biochemical processes there is a competition between these two series. A higher dietary intake of omega-6 results in the excessive incorporation of these molecules in the cell membrane with numerous pathological consequences, presumably due to the formation of proinflammatory eicosanoids. Members of the omega-3 family and their derivatives modulate the inflammatory action. Essential fatty acids play a major role in brain development and brain functioning. The omega-3 series members docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) provide fluidity to the cell membrane, facilitating certain processes including neurotransmission and ion channel flow. It is thought that omega-3 deficiency during the fetal and postnatal period may have a long-term effect at various levels. Epidemiological studies have demonstrated a positive association between omega-3 deficits and mood disorders. As for treatment, there is convincing evidence that add-on omega-3 fatty acids to standard antidepressant pharmacotherapy results in improved mood. There is no evidence that fatty acid monotherapy has a mood-elevating effect, with a possible exception for childhood depression. There are indications that omega-3 has a prophylactic effect on perinatal depression and has a negative effect on natural killer cell activity and T-lymphocyte function. These observations need further study in view of the popularity of self-medication. Copyright 2008 Prous Science, S.A.U. or its licensors. All rights reserved.

  14. Fatty acid-amino acid conjugates diversification in Lepidopteran caterpillars

    USDA-ARS?s Scientific Manuscript database

    Fatty acid amino acid conjugates (FACs) have been found in Noctuid as well as Sphingid caterpillar oral secretions and especially volicitin [N-(17-hydroxylinolenoyl)-L-Glutamine] and its biochemical precursor, N-linolenoyl-L-glutamine, are known elicitors of induced volatile emissions in corn plants...

  15. Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production.

    PubMed

    Kishino, Shigenobu; Ogawa, Jun; Yokozeki, Kenzo; Shimizu, Sakayu

    2009-08-01

    Lactobacillus plantarum AKU 1009a effectively transforms linoleic acid to conjugated linoleic acids of cis-9,trans-11-octadecadienoic acid (18:2) and trans-9,trans-11-18:2. The transformation of various polyunsaturated fatty acids by washed cells of L. plantarum AKU 1009a was investigated. Besides linoleic acid, alpha-linolenic acid [cis-9,cis-12,cis-15-octadecatrienoic acid (18:3)], gamma-linolenic acid (cis-6,cis-9,cis-12-18:3), columbinic acid (trans-5,cis-9,cis-12-18:3), and stearidonic acid [cis-6,cis-9,cis-12,cis-15-octadecatetraenoic acid (18:4)] were found to be transformed. The fatty acids transformed by the strain had the common structure of a C18 fatty acid with the cis-9,cis-12 diene system. Three major fatty acids were produced from alpha-linolenic acid, which were identified as cis-9,trans-11,cis-15-18:3, trans-9,trans-11,cis-15-18:3, and trans-10,cis-15-18:2. Four major fatty acids were produced from gamma-linolenic acid, which were identified as cis-6,cis-9,trans-11-18:3, cis-6,trans-9,trans-11-18:3, cis-6,trans-10-18:2, and trans-10-octadecenoic acid. The strain transformed the cis-9,cis-12 diene system of C18 fatty acids into conjugated diene systems of cis-9,trans-11 and trans-9,trans-11. These conjugated dienes were further saturated into the trans-10 monoene system by the strain. The results provide valuable information for understanding the pathway of biohydrogenation by anaerobic bacteria and for establishing microbial processes for the practical production of conjugated fatty acids, especially those produced from alpha-linolenic acid and gamma-linolenic acid.

  16. Fatty acid composition of the cellular slime mold Polysphondylium pallidum.

    PubMed

    Saito, T; Ochiai, H

    1998-03-01

    The cellular slime mold Polysphondylium pallidum was grown upon Escherichia coli B/r, and the fatty acid compositions of total lipids obtained from vegetative amebae and aggregation-competent cells were compared. Fatty acids isolated from vegetative cells included C-17 and C-19 cyclopropane fatty acids and also straight-chain, saturated fatty acids. The cyclopropane fatty acids were derived from the ingested bacteria. Development of amebae to aggregation-competent cells was accompanied by a substantial decrease in saturated cyclopropane fatty acids and a concomitant increase in unsaturated fatty acids and unsaturated cyclopropane fatty acids, mostly as 18:3 (5,9,12). We report here the fatty acid composition and identify the occurrence of delta 5 desaturation of cyclopropane fatty acids, namely, 9,10-methylene 5-hexadecenoic acid and 11,12-methylene 5-octadecenoic acid. These fatty acids have not been reported previously in the related species Dictyostelium discoideum, which also feeds on E. coli B/r and has delta 5-desaturation activity.

  17. Lipase-catalyzed synthesis of fatty acid amide (erucamide) using fatty acid and urea.

    PubMed

    Awasthi, Neeraj Praphulla; Singh, R P

    2007-01-01

    Ammonolysis of fatty acids to the corresponding fatty acid amides is efficiently catalysed by Candida antartica lipase (Novozym 435). In the present paper lipase-catalysed synthesis of erucamide by ammonolysis of erucic acid and urea in organic solvent medium was studied and optimal conditions for fatty amides synthesis were established. In this process erucic acid gave 88.74 % pure erucamide after 48 hour and 250 rpm at 60 degrees C with 1:4 molar ratio of erucic acid and urea, the organic solvent media is 50 ml tert-butyl alcohol (2-methyl-2-propanol). This process for synthesis is economical as we used urea in place of ammonia or other amidation reactant at atmospheric pressure. The amount of catalyst used is 3 %.

  18. Identification of a two-component fatty acid kinase responsible for host fatty acid incorporation by Staphylococcus aureus

    PubMed Central

    Parsons, Joshua B.; Broussard, Tyler C.; Bose, Jeffrey L.; Rosch, Jason W.; Jackson, Pamela; Subramanian, Chitra; Rock, Charles O.

    2014-01-01

    Extracellular fatty acid incorporation into the phospholipids of Staphylococcus aureus occurs via fatty acid phosphorylation. We show that fatty acid kinase (Fak) is composed of two dissociable protein subunits encoded by separate genes. FakA provides the ATP binding domain and interacts with two distinct FakB proteins to produce acyl-phosphate. The FakBs are fatty acid binding proteins that exchange bound fatty acid/acyl-phosphate with fatty acid/acyl-phosphate presented in detergent micelles or liposomes. The ΔfakA and ΔfakB1 ΔfakB2 strains were unable to incorporate extracellular fatty acids into phospholipid. FakB1 selectively bound saturated fatty acids whereas FakB2 preferred unsaturated fatty acids. Affymetrix array showed a global perturbation in the expression of virulence genes in the ΔfakA strain. The severe deficiency in α-hemolysin protein secretion in ΔfakA and ΔfakB1 ΔfakB2 mutants coupled with quantitative mRNA measurements showed that fatty acid kinase activity was required to support virulence factor transcription. These data reveal the function of two conserved gene families, their essential role in the incorporation of host fatty acids by Gram-positive pathogens, and connects fatty acid kinase to the regulation of virulence factor transcription in S. aureus. PMID:25002480

  19. Research on food and nutrition characteristics of conjugated fatty acids.

    PubMed

    Tsuduki, Tsuyoshi

    2015-01-01

    In this study, the physiological effects of fatty acids with conjugated double bonds were widely examined in vitro and in vivo. Initially, a method for determination of conjugated fatty acids in food and biological samples was established. I then clarified that the oxidative stability of conjugated fatty acids was improved by the form of triacylglycerol and addition of an antioxidant, and the influence of this effect on the metabolism and pharmacokinetics of conjugated fatty acids was clarified in vivo. In addition, antitumor, anti-angiogenesis, and antiobesity effects of conjugated fatty acids were found for the first time, thus demonstrating the usefulness of conjugated fatty acids. This communication mainly outlines the data obtained for conjugated linolenic acid. In addition, this review summarizes my research on conjugated fatty acid.

  20. Inhibition of Ileal Water Absorption by Intraluminal Fatty Acids INFLUENCE OF CHAIN LENGTH, HYDROXYLATION, AND CONJUGATION OF FATTY ACIDS

    PubMed Central

    Ammon, Helmut V.; Phillips, Sidney F.

    1974-01-01

    The influence of fatty acids on ileal absorption of water, electrolytes, glucose, and taurocholate was examined in Thirty-Vella fistulas in five mongrel dogs. Fatty acid absorption also was measured. Segments of terminal ileum were perfused at steady state with isotonic electrolyte solutions containing 11.2 mM glucose, 4.5 mM taurocholate, and 0.1-5.0 mM fatty acid. Three C18 fatty acids, oleic acid, 10(9)-hydroxystearic acid, and ricinoleic acid, completely inhibited water absorption at 5 mM. Sodium, chloride, and potassium absorptions were inhibited in parallel with absorption of water. Differences between the potencies of C18 fatty acids were apparent when lesser concentrations were perfused. Dodecanoic and decanoic acids were as effective as C18 fatty acids at 5 mM but octanoic and hexanoic acids were ineffective. The polar group of C18 fatty acids was modified by conjugating oleic and ricinoleic acids with taurine. When these compounds and a substituted C18 fatty acid, p-n-decylbenzenesulfonate, were perfused, water absorption was also inhibited. Short-chain fatty acids (C3 and C4) and their hydroxylated derivatives were ineffective at 5 mM. When water absorption was inhibited, absorption of glucose and taurocholate was decreased. We speculate that the phenomenon of inhibition of water and electrolyte absorption by fatty acids may be relevant to steatorrhea and diarrhea in man. Images PMID:4808636

  1. Identification of fatty acids in canine seminal plasma.

    PubMed

    Díaz, R; Inostroza, K; Risopatrón, J; Sanchez, R; Sepúlveda, N

    2014-03-01

    Seminal plasma contains various biochemical components associated with sperm function. However, there is limited information regarding the fatty acid composition of seminal plasma and their effect on sperm. The aim of this study was to identify the fatty acid content in canine seminal plasma using gas chromatography. Twelve ejaculates were studied, the seminal plasma was obtained by centrifugation and then the lipids were extracted, methylated and analysed by chromatography. The total lipids in the seminal plasma were 2.5 ± 0.3%, corresponding to 85% saturated fatty acids (SFA) and 15% unsaturated fatty acids (UFA). The greatest proportions of SFA were palmitic acid (30.4%), stearic acid (23.4%) and myristic acid (5.3%) and of UFA oleic acid (9.0%). Therefore, the protocols and techniques used enabled the identification of 18 different fatty acids in canine seminal plasma, which constitutes a good method to evaluate and quantify the fatty acid profile in this species.

  2. Omega-3 fatty acids (ῳ-3 fatty acids) in epilepsy: animal models and human clinical trials.

    PubMed

    DeGiorgio, Christopher M; Taha, Ameer Y

    2016-10-01

    There is growing interest in alternative and nutritional therapies for drug resistant epilepsy. ῳ-3 fatty acids such as fish or krill oil are widely available supplements used to lower triglycerides and enhance cardiovascular health. ῳ-3 fatty acids have been studied extensively in animal models of epilepsy. Yet, evidence from randomized controlled clinical trials in epilepsy is at an early stage. This report focuses on the key ῳ-3 fatty acids DHA and EPA, their incorporation into the lipid bilayer, modulation of ion channels, and mechanisms of action in reducing excitability within the central nervous system. This paper presents pre-clinical evidence from mouse, rat, and canine models, and reports the efficacy of n-3 fatty acids in randomized controlled clinical trials. An English language search of PubMed and Google scholar for the years 1981-2016 was performed for animal studies and human randomized controlled clinical trials. Expert commentary: Basic science and animal models provide a cogent rationale and substantial evidence for a role of ῳ-3 fatty acids in reducing seizures. Results in humans are limited. Recent Phase II RCT evidence suggests that low to moderate dose of ῳ-3 fatty acids reduce seizures; however, larger multicenter randomized trials are needed to confirm or refute the evidence. The safety, health effects, low cost and ease of use make ῳ-3 fatty acids an intriguing alternative therapy for drug resistant epilepsy. Though safety of profile is excellent, the human data is not yet sufficient to support efficacy in drug resistant epilepsy at this time.

  3. Fatty acid profile of unconventional oilseeds.

    PubMed

    Sabikhi, Latha; Sathish Kumar, M H

    2012-01-01

    The continued increase in human population has resulted in the rise in the demand as well as the price of edible oils, leading to the search for alternative unconventional sources of oils, particularly in the developing countries. There are hundreds of un- or underexplored plant seeds rich in oil suitable for edible or industrial purposes. Many of them are rich in polyunsaturated essential fatty acids, which establish their utility as "healthy oils." Some agrowaste products such as rice bran have gained importance as a potential source of edible oil. Genetic modification has paved the way for increasing the oil yields and improving the fatty acid profiles of traditional as well as unconventional oilseeds. Single cell oils are also novel sources of edible oil. Some of these unconventional oils may have excellent potential for medicinal and therapeutic uses, even if their low oil contents do not promote commercial production as edible oils.

  4. Determination of the main hydrolysis product of O-ethyl S-2-diisopropylaminoethyl methylphosphonothiolate, ethyl methylphosphonic acid, in human serum.

    PubMed

    Katagi, M; Nishikawa, M; Tatsuno, M; Tsuchihashi, H

    1997-02-21

    For the unequivocal proof of the use of a nerve agent O-ethyl S-2-diisopropylaminoethyl methylphosphonothiolate (VX), a rapid, accurate and sensitive method which allows us to identify its main hydrolysis product ethyl methylphosphonic acid (EMPA) in human serum was explored by GC-MS. GC-MS analysis was performed after solvent extraction with acetonitrile in acidic conditions from the serum sample, which was previously deproteinized by micro-ultrafiltration, and subsequent tert.-butyldimethylsilyl derivatization with N-methyl-N-(tert.-butyldimethylsilyl)trifluoroacetamide (MTBSTFA) with 1% tert.-butyldimethylsilyl chloride (t-BDMSC). Linear calibration curves were obtained in the concentration range from 50 to 500 ng/ml for EMPA in the full-scan EI mode and from 5 to 50 ng/ml for EMPA in the SIM EI mode. The relative standard deviation obtained at a sample concentration of 50 ng/ml was 8.4% in the full-scan mode and 7.3% in the SIM mode. Upon applying the full-scan EI and CI mode, 40 ng/ml and 80 ng/ml were the detection limits. Using the SIM-EI mode, in which the ion at m/z 153 was chosen, the limit was 3 ng/ml.

  5. [The fatty acids and fatty aldehydes of blood as a biochemical of multiple organ failure].

    PubMed

    Osipenko, A N; Akulich, N V; Marochkov, A V

    2012-10-01

    The article presents the results of analysis of fatty acids and fatty aldehydes of plasma and blood erythrocytes in patients with the syndrome of multiple organ failure. The increase of relative level of mono-unsaturated fatty acids and decrease of poly-saturated fatty acids and saturated stearic acid in blood plasma is demonstrated. The reliable alterations in erythrocytes concerning the content of saturated palmitic and poly-saturated linoleic fatty acids are detected. In patients with multiple organ failure the decrease of level of fatty aldehydes and cholesterol in blood plasma is established too. The conclusion is made about significant role of mono non-saturated fatty acids in disorders of systemic haemodynamics and evaluation of degree of disorder of lipid metabolism between cells and blood plasma lipoproteins.

  6. Fatty acid effects on fibroblast cholesterol synthesis

    SciTech Connect

    Shireman, R.B.; Muth, J.; Lopez, C.

    1987-05-01

    Two cell lines of normal (CRL 1475, GM5565) and of familial hypercholesterolemia (FH) (CM 486,488) fibroblasts were preincubated with medium containing the growth factor ITS, 2.5 mg/ml fatty acid-free BSA, or 35.2 ..mu..mol/ml of these fatty acids complexed with 2.5 mg BSA/ml: stearic (18:0), caprylic (8:0), oleic (18:1;9), linoleic (18:2;9,12), linolenic (18:3;9,12,15), docosahexaenoic (22:6;4,7,10,13,16,19)(DHA) or eicosapentaenoic (20:5;5,8,11,14,17)(EPA). After 20 h, cells were incubated for 2 h with 0.2 ..mu..Ci (/sup 14/C)acetate/ml. Cells were hydrolyzed; an aliquot was quantitated for radioactivity and protein. After saponification and extraction with hexane, radioactivity in the aqueous and organic phases was determined. The FH cells always incorporated 30-90% more acetate/mg protein than normal cells but the pattern of the fatty acid effects was similar in both types. When the values were normalized to 1 for the BSA-only group, cells with ITS had the greatest (/sup 14/C)acetate incorporation (1.45) followed by the caprylic group (1.14). Cells incubated with 18:3, 20:6 or 22:6 incorporated about the same amount as BSA-only. Those preincubated with 18:2, 18:1, 18:0 showed the least acetate incorporation (0.87, 0.59 and 0.52, respectively). The percentage of total /sup 14/C counts which extracted into hexane was much greater in FH cells; however, these values varied with the fatty acid, e.g., 1.31(18:0) and 0.84(8:0) relative to 1(BSA).

  7. ω-3 Fatty acids reverse lipotoxity through induction of autophagy in nonalcoholic fatty liver disease.

    PubMed

    Chen, Yi; Xu, Chengfu; Yan, Tianlian; Yu, Chaohui; Li, Youming

    2015-01-01

    The aim of this study was to evaluate the effect of ω-3 fatty acids on nonalcoholic fatty liver disease concerning hepatocyte lipid accumulation as well as apoptosis induced by free fatty acids (FFAs) and to explore the underlying mechanism involving autophagy. Hepatocytes were incubated with a mixture of free fatty acids (FFAs) to mimic in vitro lipotoxicity in the pathogenesis of nonalcoholic fatty liver disease, presented by lipid accumulation and cellular apoptosis. Chemical inhibitor or inducer of autophagy and genetic deficit cells, as well as ω-3 fatty acids were used as intervention. The autophagic role of ω-3 fatty acids was investigated using Western blot and immunofluorescence. The underlying mechanism of ω-3 fatty acids involving autophagy was preliminarily explored by quantitative real-time polymerase chain reaction and Western blot. FFAs induce lipid accumulation and apoptosis in hepatocytes. Inhibition or genetic defect of autophagy increases lipid accumulation induced by FFA, whereas induction acts inversely. ω-3 Fatty acids reduced lipid accumulation and inhibited apoptosis induced by FFA. ω-3 Fatty acids induced autophagy by downregulating stearoyl-CoA desaturase 1 expression in hepatocytes. ω-3 Fatty acids exert protective effects on hepatocytes against lipotoxicity through induction of autophagy, as demonstrated by inhibition of lipid accumulation and apoptosis. Copyright © 2015 Elsevier Inc. All rights reserved.

  8. Unsaturated fatty acids, desaturases, and human health.

    PubMed

    Lee, Hyungjae; Park, Woo Jung

    2014-02-01

    With the increasing concern for health and nutrition, dietary fat has attracted considerable attention. The composition of fatty acids in a diet is important since they are associated with major diseases, such as cancers, diabetes, and cardiovascular disease. The biosynthesis of unsaturated fatty acids (UFA) requires the expression of dietary fat-associated genes, such as SCD, FADS1, FADS2, and FADS3, which encode a variety of desaturases, to catalyze the addition of a double bond in a fatty acid chain. Recent studies using new molecular techniques and genomics, as well as clinical trials have shown that these genes and UFA are closely related to physiological conditions and chronic diseases; it was found that the existence of alternative transcripts of the desaturase genes and desaturase isoforms might affect human health and lipid metabolism in different ways. In this review, we provide an overview of UFA and desaturases associated with human health and nutrition. Moreover, recent findings of UFA, desaturases, and their associated genes in human systems are discussed. Consequently, this review may help elucidate the complicated physiology of UFA in human health and diseases.

  9. Fatty acid oxidation and ketogenesis during development.

    PubMed

    Girard, J; Duée, P H; Ferré, P; Pégorier, J P; Escriva, F; Decaux, J F

    1985-01-01

    Fatty acids are the preferred oxidative substrates of the heart, skeletal muscles, kidney cortex and liver in adult mammals. They are supplied to these tissues either as nonesterified fatty acids (NEFA), or as triglycerides after hydrolysis by lipoprotein lipase. During fetal life, tissue capacity to oxidize NEFA is very low, even in species in which the placental transfer of NEFA and carnitine is high. At birth, the ability to oxidize NEFA from endogenous sources or from milk (a high-fat diet) develops rapidly in various tissues and remains very high throughout the suckling period. Ketogenesis appears in the liver by 6 to 12 hrs after birth, and the ketone bodies are used as oxidative fuels by various tissues during the suckling period. At the time of weaning, the transition from a high-fat to a high-carbohydrate diet is attended by a progressive decrease in the ketogenic capacity of the liver, whereas other tissues (skeletal muscle, heart, kidney) maintain a high capacity for NEFA oxidation. The nutritional and hormonal factors involved in changes in fatty acid oxidation during development are discussed.

  10. Ageing, adipose tissue, fatty acids and inflammation.

    PubMed

    Pararasa, Chathyan; Bailey, Clifford J; Griffiths, Helen R

    2015-04-01

    A common feature of ageing is the alteration in tissue distribution and composition, with a shift in fat away from lower body and subcutaneous depots to visceral and ectopic sites. Redistribution of adipose tissue towards an ectopic site can have dramatic effects on metabolic function. In skeletal muscle, increased ectopic adiposity is linked to insulin resistance through lipid mediators such as ceramide or DAG, inhibiting the insulin receptor signalling pathway. Additionally, the risk of developing cardiovascular disease is increased with elevated visceral adipose distribution. In ageing, adipose tissue becomes dysfunctional, with the pathway of differentiation of preadipocytes to mature adipocytes becoming impaired; this results in dysfunctional adipocytes less able to store fat and subsequent fat redistribution to ectopic sites. Low grade systemic inflammation is commonly observed in ageing, and may drive the adipose tissue dysfunction, as proinflammatory cytokines are capable of inhibiting adipocyte differentiation. Beyond increased ectopic adiposity, the effect of impaired adipose tissue function is an elevation in systemic free fatty acids (FFA), a common feature of many metabolic disorders. Saturated fatty acids can be regarded as the most detrimental of FFA, being capable of inducing insulin resistance and inflammation through lipid mediators such as ceramide, which can increase risk of developing atherosclerosis. Elevated FFA, in particular saturated fatty acids, maybe a driving factor for both the increased insulin resistance, cardiovascular disease risk and inflammation in older adults.

  11. 40 CFR 721.10512 - Fatty acid maleic acid amides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid maleic acid amides (generic... Specific Chemical Substances § 721.10512 Fatty acid maleic acid amides (generic). (a) Chemical substance... fatty acid maleic acid amides (PMNs P-07-563 and P-07-564) are subject to reporting under this section...

  12. 40 CFR 721.10512 - Fatty acid maleic acid amides (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid maleic acid amides (generic... Specific Chemical Substances § 721.10512 Fatty acid maleic acid amides (generic). (a) Chemical substance... fatty acid maleic acid amides (PMNs P-07-563 and P-07-564) are subject to reporting under this section...

  13. 21 CFR 172.862 - Oleic acid derived from tall oil fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Oleic acid derived from tall oil fatty acids. 172... FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.862 Oleic acid derived from tall oil fatty acids. The food additive oleic acid derived from tall oil fatty acids may be safely used in food and as...

  14. 21 CFR 172.862 - Oleic acid derived from tall oil fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Oleic acid derived from tall oil fatty acids. 172... FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.862 Oleic acid derived from tall oil fatty acids. The food additive oleic acid derived from tall oil fatty acids may be safely used in food and as...

  15. 21 CFR 172.862 - Oleic acid derived from tall oil fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Oleic acid derived from tall oil fatty acids. 172... FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.862 Oleic acid derived from tall oil fatty acids. The food additive oleic acid derived from tall oil fatty acids may be safely used in food and...

  16. 21 CFR 172.862 - Oleic acid derived from tall oil fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Oleic acid derived from tall oil fatty acids. 172... FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.862 Oleic acid derived from tall oil fatty acids. The food additive oleic acid derived from tall oil fatty acids may be safely used in food and...

  17. 21 CFR 172.862 - Oleic acid derived from tall oil fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Oleic acid derived from tall oil fatty acids. 172... Multipurpose Additives § 172.862 Oleic acid derived from tall oil fatty acids. The food additive oleic acid derived from tall oil fatty acids may be safely used in food and as a component in the manufacture of...

  18. Fatty acids of Thespesia populnea: Mass spectrometry of picolinyl esters of cyclopropene fatty acids

    USDA-ARS?s Scientific Manuscript database

    Thespesia populnea belongs to the plant family of Malvaceae which contain cyclopropane and cyclopropene fatty acids. However, previous literature reports vary regarding the content of these compounds in Thespesia populnea seed oil. In this work, the content of malvalic acid (8,9-methylene-9-heptade...

  19. Fatty acid transport and activation and the expression patterns of genes involved in fatty acid trafficking.

    PubMed

    Sandoval, Angel; Fraisl, Peter; Arias-Barrau, Elsa; Dirusso, Concetta C; Singer, Diane; Sealls, Whitney; Black, Paul N

    2008-09-15

    These studies defined the expression patterns of genes involved in fatty acid transport, activation and trafficking using quantitative PCR (qPCR) and established the kinetic constants of fatty acid transport in an effort to define whether vectorial acylation represents a common mechanism in different cell types (3T3-L1 fibroblasts and adipocytes, Caco-2 and HepG2 cells and three endothelial cell lines (b-END3, HAEC, and HMEC)). As expected, fatty acid transport protein (FATP)1 and long-chain acyl CoA synthetase (Acsl)1 were the predominant isoforms expressed in adipocytes consistent with their roles in the transport and activation of exogenous fatty acids destined for storage in the form of triglycerides. In cells involved in fatty acid processing including Caco-2 (intestinal-like) and HepG2 (liver-like), FATP2 was the predominant isoform. The patterns of Acsl expression were distinct between these two cell types with Acsl3 and Acsl5 being predominant in Caco-2 cells and Acsl4 in HepG2 cells. In the endothelial lines, FATP1 and FATP4 were the most highly expressed isoforms; the expression patterns for the different Acsl isoforms were highly variable between the different endothelial cell lines. The transport of the fluorescent long-chain fatty acid C(1)-BODIPY-C(12) in 3T3-L1 fibroblasts and 3T3-L1 adipocytes followed typical Michaelis-Menten kinetics; the apparent efficiency (k(cat)/K(T)) of this process increases over 2-fold (2.1 x 10(6)-4.5 x 10(6)s(-1)M(-1)) upon adipocyte differentiation. The V(max) values for fatty acid transport in Caco-2 and HepG2 cells were essentially the same, yet the efficiency was 55% higher in Caco-2 cells (2.3 x 10(6)s(-1)M(-1) versus 1.5 x 10(6)s(-1)M(-1)). The kinetic parameters for fatty acid transport in three endothelial cell types demonstrated they were the least efficient cell types for this process giving V(max) values that were nearly 4-fold lower than those defined form 3T3-L1 adipocytes, Caco-2 cells and HepG2 cells. The

  20. Cystamine and ethyl-eicosapentaenoic acid treatment fail to prevent malonate-induced striatal toxicity in mice.

    PubMed

    Sivananthan, Saskia N; Leavitt, Blair R

    2011-12-01

    Cystamine has demonstrated neuroprotective activity in a variety of studies, and is currently being evaluated in a human clinical trial in Huntington's disease (HD). Cystamine treatment of various genetic models of HD demonstrated protection against neurodegeneration and/or improvement in behavior. Given the need for a rapid screening tool for HD therapeutics, we assessed the potential therapeutic benefits of cystamine in a short-term acute toxicity murine model of striatal cell death. Cystamine did not provide neuroprotection against bilateral intrastriatal malonate injections in mice as measured by lesion size, loss of striatal volume, or decreased striatal neuronal counts. Similar results were obtained for treatment with another potential therapeutic agent that was protective in genetic mouse models of HD, the essential fatty acid ethyl-eicosapentaenoic acid. Our findings suggest that this toxic model is not reflective or predictive of findings in genetic mouse models, and may not be useful as a preclinical screen for HD therapeutics.

  1. Effect of succinic acid and tween-80 on glucuronidation of 2-ethyl-6-methyl-3-hydroxypyridine.

    PubMed

    Baranov, P A; Kravtsova, O U; Sariev, A K; Sherdev, V P

    2008-07-01

    We studied the effect of succinic acid on the process of glucuronidation of 2-ethyl-6-methyl-3-hydroxypyridine after peroral and intraperitoneal administration in the form of succinate or a base. Since the basic form of 2-ethyl-6-methyl-3-hydroxypyridine is insoluble in water, it was administered in 5% Tween-80. It was necessary to evaluate also the effect of Tween-80 on glucuronidation of 2-ethyl-6-methyl-3-hydroxypyridine in different administration routes. Quantitative assay of glucuronidated fractions was performed by the method of reversed-phase HPLC with fluorometrical detection. The detection limit for this method was 10 ng/ml. We confirmed that the major excretion pathway for 2-ethyl-6-methyl-3-hydroxypyridine is conjugation with glucuronic acid. It was found that succinic acid increased excretion of glucuronidated metabolite after both peroral and intraperitoneal administration of 2-ethyl-6-methyl-3-hydroxypyridine in the form of succinate and base in 5% Tween-80. The effect of Tween-80 was detected only after peroral administration, which was probably related to its effect on absorption of this compound. Tween-80 increased excretion of glucuronate after peroral administration of 2-ethyl-6-methyl-3-hydroxypyridine in the form of succinate and in 5% Tween solution.

  2. Inhibitory role of polyunsaturated fatty acids on lysophosphatidic acid-induced cancer cell migration and adhesion.

    PubMed

    Kim, Eun Kyoung; Ha, Jung Min; Kim, Young Whan; Jin, Seo Yeon; Ha, Hong Koo; Bae, Sun Sik

    2014-08-25

    Polyunsaturated fatty acids (PUFAs) have important pharmacological effects on mammalian cells. Here, we show that carboxyl group-containing PUFAs inhibit lysophosphatidic acid (LPA)-induced focal adhesion formation, thereby inhibiting migration and adhesion. Carboxyl group-containing PUFAs inhibit LPA-induced calcium mobilization, whereas ethyl ester-group containing PUFAs have no effect. In addition, carboxyl group-containing PUFAs functionally inhibit LPA-dependent RhoA activation. Given these results, we suggest that PUFAs may inhibit LPA-induced calcium/RhoA signaling pathways leading to focal adhesion formation. Carboxyl group-containing PUFAs may have a functional role in this regulatory mechanism. Copyright © 2014 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

  3. Dietary essential fatty acids change the fatty acid profile of rat neural mitochondria over time.

    PubMed

    Dyer, J R; Greenwood, C E

    1991-10-01

    This experiment examined the time course over which the amount of dietary essential fatty acids (EFA) affects brain mitochondrial fatty acids. Weanling rats were fed 20% (wt/wt) fat diets that contained either 4 or 15% (wt/wt of diet) EFA for 1, 2, 3 or 6 wk or a 10% EFA diet for 3 or 6 wk. The EFA ratio [18:2(n-6)/18:3(n-3)] of all diets was approximately 30. Fatty acid analysis of brain mitochondrial phosphatidylethanolamine, phosphatidylcholine and cardiolipin revealed that the largest dietary effect was on 18:2(n-6), which was 30% higher in rats fed the 15 vs. 4% EFA diets after 1 wk. This difference increased to twofold by 3 wk and was still twofold after 6 wk. These results demonstrate several facts: 1) the response of 18:2(n-6) in cardiolipin to dietary EFA is very fast and large, relative to changes in other quantitatively major fatty acids observed in weanling rats; 2) the 18:2(n-6) level in neural cardiolipin stabilizes after 3 wk of feeding at a level dependent upon the amount of dietary EFA; and 3) at least one neural fatty acid, 18:2(n-6), is very sensitive to amounts of dietary EFA that are well above the animal's EFA requirement.

  4. Production of hydroxylated fatty acids in genetically modified plants

    DOEpatents

    Somerville, Chris; Broun, Pierre; van de Loo, Frank

    2001-01-01

    This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fatty acids in transgenic plants.

  5. Fatty acid profiles of some Fabaceae seed oils

    USDA-ARS?s Scientific Manuscript database

    The fatty acid profiles of six seed oils of the Fabaceae (Leguminosae) family are reported and discussed. These are the seed oils of Centrosema pubescens, Clitoria ternatea, Crotalaria mucronata, Macroptilium lathyroides, Pachyrhizus erosus, and Senna alata. The most common fatty acid in the fatty a...

  6. 40 CFR 721.3627 - Branched synthetic fatty acid.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Branched synthetic fatty acid. 721... Substances § 721.3627 Branched synthetic fatty acid. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a branched synthetic fatty...

  7. 40 CFR 721.3627 - Branched synthetic fatty acid.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Branched synthetic fatty acid. 721... Substances § 721.3627 Branched synthetic fatty acid. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a branched synthetic fatty...

  8. Temperature Affects Fatty Acids In Methylococcus Capsulatus

    NASA Technical Reports Server (NTRS)

    Jahnke, Linda L.

    1993-01-01

    According to report, temperature of growth of thermotolerant, methane-oxidizing bacterium Methylococcus capsulatus (Bath) affects both proportion of monounsaturated fatty acids and cis/trans ratio of these acids in cell membrane. Because suboptimum growth temperature is potential stress factor, it may be possible to use such cis/trans ratios as indices of stresses upon methane-oxidizing microbial communities. Research in microbiology of methanotrophs increasing because of possible commercial exploitation of these organisms as biocatalysts or as sources of useful polymers; knowledge of effect of temperature on ability of methanotrophs to utilize methane useful in optimization of conditions of growth.

  9. Temperature Affects Fatty Acids In Methylococcus Capsulatus

    NASA Technical Reports Server (NTRS)

    Jahnke, Linda L.

    1993-01-01

    According to report, temperature of growth of thermotolerant, methane-oxidizing bacterium Methylococcus capsulatus (Bath) affects both proportion of monounsaturated fatty acids and cis/trans ratio of these acids in cell membrane. Because suboptimum growth temperature is potential stress factor, it may be possible to use such cis/trans ratios as indices of stresses upon methane-oxidizing microbial communities. Research in microbiology of methanotrophs increasing because of possible commercial exploitation of these organisms as biocatalysts or as sources of useful polymers; knowledge of effect of temperature on ability of methanotrophs to utilize methane useful in optimization of conditions of growth.

  10. Engineered Production of Short Chain Fatty Acid in Escherichia coli Using Fatty Acid Synthesis Pathway

    PubMed Central

    Jawed, Kamran; Mattam, Anu Jose; Fatma, Zia; Wajid, Saima; Abdin, Malik Z.; Yazdani, Syed Shams

    2016-01-01

    Short-chain fatty acids (SCFAs), such as butyric acid, have a broad range of applications in chemical and fuel industries. Worldwide demand of sustainable fuels and chemicals has encouraged researchers for microbial synthesis of SCFAs. In this study we compared three thioesterases, i.e., TesAT from Anaerococcus tetradius, TesBF from Bryantella formatexigens and TesBT from Bacteroides thetaiotaomicron, for production of SCFAs in Escherichia coli utilizing native fatty acid synthesis (FASII) pathway and modulated the genetic and bioprocess parameters to improve its yield and productivity. E. coli strain expressing tesBT gene yielded maximum butyric acid titer at 1.46 g L-1, followed by tesBF at 0.85 g L-1 and tesAT at 0.12 g L-1. The titer of butyric acid varied significantly depending upon the plasmid copy number and strain genotype. The modulation of genetic factors that are known to influence long chain fatty acid production, such as deletion of the fadD and fadE that initiates the fatty acid degradation cycle and overexpression of fadR that is a global transcriptional activator of fatty acid biosynthesis and repressor of degradation cycle, did not improve the butyric acid titer significantly. Use of chemical inhibitor cerulenin, which restricts the fatty acid elongation cycle, increased the butyric acid titer by 1.7-fold in case of TesBF, while it had adverse impact in case of TesBT. In vitro enzyme assay indicated that cerulenin also inhibited short chain specific thioesterase, though inhibitory concentration varied according to the type of thioesterase used. Further process optimization followed by fed-batch cultivation under phosphorous limited condition led to production of 14.3 g L-1 butyric acid and 17.5 g L-1 total free fatty acid at 28% of theoretical yield. This study expands our understanding of SCFAs production in E. coli through FASII pathway and highlights role of genetic and process optimization to enhance the desired product. PMID:27466817

  11. Epoxygenated Fatty Acids Inhibit Retinal Vascular Inflammation

    PubMed Central

    Capozzi, Megan E.; Hammer, Sandra S.; McCollum, Gary W.; Penn, John S.

    2016-01-01

    The objective of the present study was to assess the effect of elevating epoxygenated fatty acids on retinal vascular inflammation. To stimulate inflammation we utilized TNFα, a potent pro-inflammatory mediator that is elevated in the serum and vitreous of diabetic patients. In TNFα-stimulated primary human retinal microvascular endothelial cells, total levels of epoxyeicosatrienoic acids (EETs), but not epoxydocosapentaenoic acids (EDPs), were significantly decreased. Exogenous addition of 11,12-EET or 19,20-EDP when combined with 12-(3-adamantane-1-yl-ureido)-dodecanoic acid (AUDA), an inhibitor of epoxide hydrolysis, inhibited VCAM-1 and ICAM-1 expression and protein levels; conversely the diol product of 19,20-EDP hydrolysis, 19,20-DHDP, induced VCAM1 and ICAM1 expression. 11,12-EET and 19,20-EDP also inhibited leukocyte adherence to human retinal microvascular endothelial cell monolayers and leukostasis in an acute mouse model of retinal inflammation. Our results indicate that this inhibition may be mediated through an indirect effect on NFκB activation. This is the first study demonstrating a direct comparison of EET and EDP on vascular inflammatory endpoints, and we have confirmed a comparable efficacy from each isomer, suggesting a similar mechanism of action. Taken together, these data establish that epoxygenated fatty acid elevation will inhibit early pathology related to TNFα-induced inflammation in retinal vascular diseases. PMID:27966642

  12. Icosapent ethyl: Eicosapentaenoic acid concentration and triglyceride-lowering effects across clinical studies.

    PubMed

    Bays, Harold E; Ballantyne, Christie M; Doyle, Ralph T; Juliano, Rebecca A; Philip, Sephy

    2016-09-01

    Icosapent ethyl is a high-purity prescription form of eicosapentaenoic acid (EPA) ethyl ester approved at a dose of 4g/day as an adjunct to diet to reduce triglyceride (TG) levels in adult patients with severe (≥500mg/dL) hypertriglyceridemia. This post-hoc exploratory analysis examined the relationship of icosapent ethyl dose with EPA concentrations in plasma and red blood cells (RBCs) across 3 clinical studies-a phase 1 pharmacokinetic study in healthy adult volunteers and 2 pivotal phase 3 studies (MARINE and ANCHOR) in adult patients with hypertriglyceridemia-and examined the relationship between EPA levels and TG-lowering effects in MARINE and ANCHOR. In all 3 studies, icosapent ethyl produced dose-dependent increases in the concentrations of EPA in plasma and RBCs. In both MARINE and ANCHOR, these dose-dependent EPA increases correlated with the degree of TG level lowering (all P<0.01). In patients with high TG levels (≥200mg/dL) and treated with icosapent ethyl 4g/day, the end-of-treatment plasma and RBC EPA concentrations were >170μg/mL and>70μg/mL, respectively. These studies support icosapent ethyl as producing predictable dose-dependent pharmacokinetics/pharmacodynamics, with TG level lowering dependent upon icosapent ethyl dose and EPA concentrations in plasma and RBCs. Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

  13. The adjuvant activity of fatty acid esters. The role of acyl chain length and degree of saturation.

    PubMed Central

    Bomford, R

    1981-01-01

    Water-in-oil emulsions of metabolizable fatty acid esters, with the non-toxic surfactant Pluronic L122 as emulsifying agent, potentiated the humoral response to bovine serum albumin and staphylococcal toxoid in the mouse. Adjuvant activity was increased by changing the chemical nature of the esters as follows: (i) using a series of ethyl esters, adjuvant activity appeared when the acyl chain length of the fatty acid component was 16 or greater; (ii) isobutyl and isopropyl esters of palmitic acid (C16:0) were superior to ethyl; (iii) the ethyl esters of oleic (C18:1) and linoleic (C18:2) acids were better than stearic (C18:0). Since emulsions prepared with longer chain saturated esters are very viscous or solid at room temperature, and unsaturated esters are chemically reactive, emulsions were prepared with differing proportions of ethyl caprate (C10:0) and butyl stearate. At a ratio of 9:1 the emulsions possessed the low viscosity of ethyl caprate, but gained the adjuvant activity of butyl stearate. 125I-labelled BSA was retained in the footpad to a significantly greater extent than with a caprate emulsion, but reasons are given for believing that slow release of antigen is not the only mechanism of adjuvant activity. The ester emulsions caused more acute but less chronic local inflammation (footpad swelling) than Freund's incomplete adjuvant. PMID:7275184

  14. Bioavailability of long-chain omega-3 fatty acids.

    PubMed

    Schuchardt, Jan Philipp; Hahn, Andreas

    2013-07-01

    Supplements have reached a prominent role in improving the supply of long-chain omega-3 fatty acids, such as Eicosapentaenoic acid (EPA 20:5n-3) and Docosahexaenoic acid (DHA 22:6n-3). Similar to other nutrients, the availability of omega-3 fatty acids is highly variable and determined by numerous factors. However, the question of omega-3 fatty acids bioavailability has long been disregarded, which may have contributed to the neutral or negative results concerning their effects in several studies. This review provides an overview of the influence of chemical binding form (free fatty acids bound in ethylesters, triacylglycerides or phospholipids), matrix effects (capsule ingestion with concomitant intake of food, fat content in food) or galenic form (i.e. microencapsulation, emulsification) on the bioavailability of omega-3 fatty acids. There is a need to systematically investigate the bioavailability of omega-3 fatty acids formulations, which might be a key to designing more effective studies in the future.

  15. Analysis of methylphosphonic acid, ethyl methylphosphonic acid and isopropyl methylphosphonic acid at low microgram per liter levels in groundwater.

    PubMed

    Sega, G A; Tomkins, B A; Griest, W H

    1997-11-28

    A method is described for determining methylphosphonic acid, ethyl methylphosphonic acid and isopropyl methylphosphonic acid, which are hydrolysis products of the nerve agents VX (S-2-diisopropylaminoethyl O-ethyl methylphosphonothiolate) and GB (sarin, isopropylmethyl phosphonofluoridate). The analytes are extracted from 50 ml groundwater using a solid-phase extraction column packed with 500 mg of silica with a bonded quaternary amine phase, and are eluted and derivatized with methanolic trimethylphenylammonium hydroxide. Separation and quantitation are achieved using a capillary column gas chromatograph equipped with a flame photometric detector operated in its phosphorus-selective mode. Two independent statistically-unbiased procedures were employed to determine the detection limits, which ranged between 3 and 9 micrograms/l, for the three analytes.

  16. Cost-effectiveness of ethyl-eicosapentaenoic acid in the treatment of bipolar disorder

    PubMed Central

    Frangou, Sophia; McCrone, Paul

    2013-01-01

    Background: This study develops an economic model to evaluate the cost-effectiveness of ethyl-eicosapentaenoic acid (ethyl-EPA) as an adjunct treatment of bipolar I disorder. Methods: A 1-year Markov model is used incorporating three health states: euthymic, manic and depressive. The model was populated using outcomes from a clinical trial on clinical efficacy and other published literature. Results: The incremental cost-effectiveness ratio (ICER) per quality-adjusted life year (QALY) of ethyl-EPA in comparison with placebo was estimated to be -£2,782 in 2008/09 prices, the negative ICER indicating ethyl-EPA to be a more effective and less costly treatment option than placebo in terms of cost savings of other resource use. Conclusions: The sensitivity analysis indicated that the results were robust. Future research covering a longer time period using broader costs of the disease will be required to consolidate these findings. PMID:24167678

  17. Higher hypochlorous acid scavenging activity of ethyl pyruvate compared to its sodium salt.

    PubMed

    Olek, Robert Antoni; Ziolkowski, Wieslaw; Kaczor, Jan Jacek; Wierzba, Tomasz Henryk; Antosiewicz, Jedrzej

    2011-01-01

    Although a number of studies have focused on the higher ethyl pyruvate antioxidative activity than its sodium salt under various stress conditions, and the greater protective properties of the ester form have been suggested as the effect of better cell membrane penetration, the molecular mechanism has remained unclear. The aim of the present study was therefore to compare the antioxidative activities of sodium and ethyl pyruvate under in vitro conditions by using a liver homogenate as the model for cell membrane transport deletion. The potential effect of ethanol was also evaluated, and hypochlorous acid was used as an oxidant. Our data indicate the concentration-dependent scavenging potency of both sodium and ethyl pyruvate, with the ester having higher activity. This effect was not related to the presence of ethanol. Better protection of the liver homogenate by ethyl pyruvate was also apparent, despite the fact that cell membrane transport was omitted.

  18. Neurological benefits of omega-3 fatty acids.

    PubMed

    Dyall, S C; Michael-Titus, A T

    2008-01-01

    The central nervous system is highly enriched in long-chain polyunsaturated fatty acid (PUFA) of the omega-6 and omega-3 series. The presence of these fatty acids as structural components of neuronal membranes influences cellular function both directly, through effects on membrane properties, and also by acting as a precursor pool for lipid-derived messengers. An adequate intake of omega-3 PUFA is essential for optimal visual function and neural development. Furthermore, there is increasing evidence that increased intake of the long-chain omega-3 PUFA, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), may confer benefits in a variety of psychiatric and neurological disorders, and in particular neurodegenerative conditions. However, the mechanisms underlying these beneficial effects are still poorly understood. Recent evidence also indicates that in addition to the positive effects seen in chronic neurodegenerative conditions, omega-3 PUFA may also have significant neuroprotective potential in acute neurological injury. Thus, these compounds offer an intriguing prospect as potentially new therapeutic approaches in both chronic and acute conditions. The purpose of this article is to review the current evidence of the neurological benefits of omega-3 PUFA, looking specifically at neurodegenerative conditions and acute neurological injury.

  19. Effect of dietary n-3 fatty acids supplementation on fatty acid metabolism in atorvastatin-administered SHR.Cg-Lepr(cp)/NDmcr rats, a metabolic syndrome model.

    PubMed

    Al Mamun, Abdullah; Hashimoto, Michio; Katakura, Masanori; Tanabe, Yoko; Tsuchikura, Satoru; Hossain, Shahdat; Shido, Osamu

    2017-01-01

    The effects of cholesterol-lowering statins, which substantially benefit future cardiovascular events, on fatty acid metabolism have remained largely obscured. In this study, we investigated the effects of atorvastatin on fatty acid metabolism together with the effects of TAK-085 containing highly purified eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) ethyl ester on atorvastatin-induced n-3 polyunsaturated fatty acid lowering in SHR.Cg-Lepr(cp)/NDmcr (SHRcp) rats, as a metabolic syndrome model. Supplementation with 10mg/kg body weight/day of atorvastatin for 17 weeks significantly decreased plasma total cholesterol and very low density lipoprotein cholesterol. Atorvastatin alone caused a subtle change in fatty acid composition particularly of EPA and DHA in the plasma, liver or erythrocyte membranes. However, the TAK-085 consistently increased both the levels of EPA and DHA in the plasma, liver and erythrocyte membranes. After confirming the reduction of plasma total cholesterol, 300mg/kg body weight/day of TAK-085 was continuously administered for another 6 weeks. Supplementation with TAK-085 did not decrease plasma total cholesterol but significantly increased the EPA and DHA levels in both the plasma and liver compared with rats administered atorvastatin only. Supplementation with atorvastatin alone significantly decreased sterol regulatory element-binding protein-1c, Δ5- and Δ6-desaturases, elongase-5, and stearoyl-coenzyme A (CoA) desaturase-2 levels and increased 3-hydroxy-3-methylglutaryl-CoA reductase mRNA expression in the liver compared with control rats. TAK-085 supplementation significantly increased stearoyl-CoA desaturase-2 mRNA expression. These results suggest that long-term supplementation with atorvastatin decreases the EPA and DHA levels by inhibiting the desaturation and elongation of n-3 fatty acid metabolism, while TAK-085 supplementation effectively replenishes this effect in SHRcp rat liver. Copyright © 2016 Elsevier Masson

  20. Fatty acid alcohol ester-synthesizing activity of lipoprotein lipase.

    PubMed

    Tsujita, T; Sumiyoshi, M; Okuda, H

    1999-12-01

    The fatty acid alcohol ester-synthesizing activity of lipoprotein lipase (LPL) was characterized using bovine milk LPL. Synthesizing activities were determined in an aqueous medium using oleic acid or trioleylglycerol as the acyl donor and equimolar amounts of long-chain alcohols as the acyl acceptor. When oleic acid and hexadecanol emulsified with gum arabic were incubated with LPL, palmityl oleate was synthesized, in a time- and dose-dependent manner. Apo-very low density lipoprotein (apoVLDL) stimulated LPL-catalyzed palmityl oleate synthesis. The apparent equilibrium ratio of fatty acid alcohol ester/oleic acid was estimated using a high concentration of LPL and a long (20 h) incubation period. The equilibrium ratio was affected by the incubation pH and the alcohol chain length. When the incubation pH was below pH 7.0 and long chain fatty acyl alcohols were used as substrates, the fatty acid alcohol ester/free fatty acid equilibrium ratio favored ester formation, with an apparent equilibrium ratio of fatty acid alcohol ester/fatty acid of about 0.9/0.1. The equilibrium ratio decreased sharply at alkaline pH (above pH 8.0). The ratio also decreased when fatty alcohols with acyl chains shorter than dodecanol were used. When a trioleoylglycerol/fatty acyl alcohol emulsion was incubated with LPL, fatty acid alcohol esters were synthesized in a dose- and time-dependent fashion. Fatty acid alcohol esters were easily synthesized from trioleoylglycerol when fatty alcohols with acyl chains longer than dodecanol were used, but synthesis was decreased with fatty alcohols with acyl chain lengths shorter than decanol, and little synthesizing activity was detected with shorter-chain fatty alcohols such as butanol or ethanol.

  1. Role of serotonin in fatty acid-induced non-alcoholic fatty liver disease in mice.

    PubMed

    Ritze, Yvonne; Böhle, Maureen; Haub, Synia; Hubert, Astrid; Enck, Paul; Zipfel, Stephan; Bischoff, Stephan C

    2013-12-09

    Saturated fatty acids are thought to be of relevance for the development of non-alcoholic fatty liver disease and obesity. However, the underlying mechanisms are poorly understood. In previous studies we found that food-derived carbohydrates such as fructose alter the intestinal serotonergic system while inducing fatty liver disease in mice. Here, we examined the effect of fatty acid quantity (11% versus 15%) and quality (saturated, monounsaturated, or polyunsaturated fatty acids) on hepatic fat accumulation, intestinal barrier and the intestinal serotonergic system. C57BL/6 mice had free access to diets enriched with one of the three fatty acids or standard diet, for 8 weeks. In an additional experiment mice were fed diets enriched with saturated, monounsaturated fatty acids or standard diet supplemented with tryptophan (0.4 g/(kg.d), 8 weeks) or not. Hepatic fat accumulation, small intestinal barrier impairment and components of the serotonergic system were measured with RT-PCR, western blot or immunoassays. For statistical analysis t-test and one-way ANOVA with Tukey's post hoc test and Bartlett's test for equal variances was used. Hepatic triglycerides, liver weight and liver to body weight ratio were significantly changed depending on the fat quality but not fat quantity. In contrast, fat quantity but not quality decreased the expression of the tight junction proteins occludin and claudin-1 in the small intestine. These changes seemed to result in enhanced portal vein endotoxin concentrations and fatty liver disease after feeding diet enriched with saturated and monounsaturated fatty acids but not polyunsaturated fatty acids. Neither fatty acid quantity nor quality significantly influenced the intestinal serotonergic system. Similarly, tryptophan supplementation had no impact on small intestinal barrier or fatty liver disease. In conclusion, diets rich in saturated or monounsaturated fatty acids promote the development of fatty liver disease in mice, likely

  2. Role of serotonin in fatty acid-induced non-alcoholic fatty liver disease in mice

    PubMed Central

    2013-01-01

    Background Saturated fatty acids are thought to be of relevance for the development of non-alcoholic fatty liver disease and obesity. However, the underlying mechanisms are poorly understood. In previous studies we found that food-derived carbohydrates such as fructose alter the intestinal serotonergic system while inducing fatty liver disease in mice. Here, we examined the effect of fatty acid quantity (11% versus 15%) and quality (saturated, monounsaturated, or polyunsaturated fatty acids) on hepatic fat accumulation, intestinal barrier and the intestinal serotonergic system. Methods C57BL/6 mice had free access to diets enriched with one of the three fatty acids or standard diet, for 8 weeks. In an additional experiment mice were fed diets enriched with saturated, monounsaturated fatty acids or standard diet supplemented with tryptophan (0.4 g/(kg.d), 8 weeks) or not. Hepatic fat accumulation, small intestinal barrier impairment and components of the serotonergic system were measured with RT-PCR, western blot or immunoassays. For statistical analysis t-test and one-way ANOVA with Tukey’s post hoc test and Bartlett’s test for equal variances was used. Results Hepatic triglycerides, liver weight and liver to body weight ratio were significantly changed depending on the fat quality but not fat quantity. In contrast, fat quantity but not quality decreased the expression of the tight junction proteins occludin and claudin-1 in the small intestine. These changes seemed to result in enhanced portal vein endotoxin concentrations and fatty liver disease after feeding diet enriched with saturated and monounsaturated fatty acids but not polyunsaturated fatty acids. Neither fatty acid quantity nor quality significantly influenced the intestinal serotonergic system. Similarly, tryptophan supplementation had no impact on small intestinal barrier or fatty liver disease. Conclusion In conclusion, diets rich in saturated or monounsaturated fatty acids promote the

  3. 40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol. 721.10457... Substances § 721.10457 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1...

  4. 40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol, fumaric acid and propylene glycol. 721.10457... Substances § 721.10457 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1...

  5. Incorporation of fatty acids by concanavalin A-stimulated lymphocytes and the effect on fatty acid composition and membrane fluidity.

    PubMed Central

    Calder, P C; Yaqoob, P; Harvey, D J; Watts, A; Newsholme, E A

    1994-01-01

    The fatty acid compositions of the neutral lipid and phospholipid fractions of rat lymph node lymphocytes were characterized. Stimulation of rat lymphocytes with the T-cell mitogen concanavalin A resulted in significant changes in the fatty acid composition of both neutral lipids and phospholipids (a decrease in the proportions of stearic, linoleic and arachidonic acids and an increase in the proportion of oleic acid). Membrane fluidity was measured using nitroxide spin-label e.s.r., and increased during culture with concanavalin A. Culturing the lymphocytes in the absence of mitogen did not affect fatty acid composition or membrane fluidity. The uptake and fate of palmitic, oleic, linoleic and arachidonic acids were studied in detail; there was a time-dependent incorporation of each fatty acid into all lipid classes but each fatty acid had a characteristic fate. Palmitic and arachidonic acids were incorporated principally into phospholipids whereas oleic and linoleic acids were incorporated in similar proportions into phospholipids and triacylglycerols. Oleic acid was incorporated mainly into phosphatidylcholine, palmitic and linoleic acids were incorporated equally into phosphatidylcholine and phosphatidylethanolamine, and arachidonic acid was incorporated mainly into phosphatidylethanolamine. Supplementation of the culture medium with particular fatty acids (myristic, palmitic, stearic, oleic, linoleic, alpha-linolenic, arachidonic, eicosapentaenoic or docosahexaenoic acid) led to enrichment of that fatty acid in both neutral lipids and phospholipids. This generated lymphocytes with phospholipids differing in saturated/unsaturated fatty acid ratio, degree of polyunsaturation, index of unsaturation and n - 6/n - 3 ratio. This method allowed the introduction into lymphocyte phospholipids of fatty acids not normally present (e.g. alpha-linolenic) or usually present in low proportions (eicosapentaenoic and docosahexaenoic). These three n - 3 polyunsaturated fatty

  6. Dietary Supplementation of Polyunsaturated Fatty Acids in Caenorhabditis elegans

    PubMed Central

    Deline, Marshall L.; Vrablik, Tracy L.; Watts, Jennifer L.

    2013-01-01

    Fatty acids are essential for numerous cellular functions. They serve as efficient energy storage molecules, make up the hydrophobic core of membranes, and participate in various signaling pathways. Caenorhabditis elegans synthesizes all of the enzymes necessary to produce a range of omega-6 and omega-3 fatty acids. This, combined with the simple anatomy and range of available genetic tools, make it an attractive model to study fatty acid function. In order to investigate the genetic pathways that mediate the physiological effects of dietary fatty acids, we have developed a method to supplement the C. elegans diet with unsaturated fatty acids. Supplementation is an effective means to alter the fatty acid composition of worms and can also be used to rescue defects in fatty acid-deficient mutants. Our method uses nematode growth medium agar (NGM) supplemented with fatty acidsodium salts. The fatty acids in the supplemented plates become incorporated into the membranes of the bacterial food source, which is then taken up by the C. elegans that feed on the supplemented bacteria. We also describe a gas chromatography protocol to monitor the changes in fatty acid composition that occur in supplemented worms. This is an efficient way to supplement the diets of both large and small populations of C. elegans, allowing for a range of applications for this method. PMID:24326396

  7. Metabolomics of Dietary Fatty Acid Restriction in Patients with Phenylketonuria

    PubMed Central

    Mütze, Ulrike; Beblo, Skadi; Kortz, Linda; Matthies, Claudia; Koletzko, Berthold; Bruegel, Mathias; Rohde, Carmen; Thiery, Joachim; Kiess, Wieland; Ceglarek, Uta

    2012-01-01

    Background Patients with phenylketonuria (PKU) have to follow a lifelong phenylalanine restricted diet. This type of diet markedly reduces the intake of saturated and unsaturated fatty acids especially long chain polyunsaturated fatty acids (LC-PUFA). Long-chain saturated fatty acids are substrates of mitochondrial fatty acid oxidation for acetyl-CoA production. LC-PUFA are discussed to affect inflammatory and haemostaseological processes in health and disease. The influence of the long term PKU diet on fatty acid metabolism with a special focus on platelet eicosanoid metabolism has been investigated in the study presented here. Methodology/Principal Findings 12 children with PKU under good metabolic control and 8 healthy controls were included. Activated fatty acids (acylcarnitines C6–C18) in dried blood and the cholesterol metabolism in serum were analyzed by liquid chromatographic tandem mass spectrometry (LC-MS/MS). Fatty acid composition of plasma glycerophospholipids was determined by gas chromatography. LC-PUFA metabolites were analyzed in supernatants by LC-MS/MS before and after platelet activation and aggregation using a standardized protocol. Patients with PKU had significantly lower free carnitine and lower activated fatty acids in dried blood compared to controls. Phytosterols as marker of cholesterol (re-) absorption were not influenced by the dietary fatty acid restriction. Fatty acid composition in glycerophospholipids was comparable to that of healthy controls. However, patients with PKU showed significantly increased concentrations of y-linolenic acid (C18:3n-6) a precursor of arachidonic acid. In the PKU patients significantly higher platelet counts were observed. After activation with collagen platelet aggregation and thromboxane B2 and thromboxane B3 release did not differ from that of healthy controls. Conclusion/Significance Long-term dietary fatty acid restriction influenced the intermediates of mitochondrial beta-oxidation. No functional

  8. Fatty Acid Activation in Cyanobacteria Mediated by Acyl-Acyl Carrier Protein Synthetase Enables Fatty Acid Recycling1[W

    PubMed Central

    Kaczmarzyk, Danuta; Fulda, Martin

    2010-01-01

    In cyanobacteria fatty acids destined for lipid synthesis can be synthesized de novo, but also exogenous free fatty acids from the culture medium can be directly incorporated into lipids. Activation of exogenous fatty acids is likely required prior to their utilization. To identify the enzymatic activity responsible for activation we cloned candidate genes from Synechocystis sp. PCC 6803 and Synechococcus elongatus PCC 7942 and identified the encoded proteins as acyl-acyl carrier protein synthetases (Aas). The enzymes catalyze the ATP-dependent esterification of fatty acids to the thiol of acyl carrier protein. The two protein sequences are only distantly related to known prokaryotic Aas proteins but they display strong similarity to sequences that can be found in almost all organisms that perform oxygenic photosynthesis. To investigate the biological role of Aas activity in cyanobacteria, aas knockout mutants were generated in the background of Synechocystis sp. PCC 6803 and S. elongatus PCC 7942. The mutant strains showed two phenotypes characterized by the inability to utilize exogenous fatty acids and by the secretion of endogenous fatty acids into the culture medium. The analyses of extracellular and intracellular fatty acid profiles of aas mutant strains as well as labeling experiments indicated that the detected free fatty acids are released from membrane lipids. The data suggest a considerable turnover of lipid molecules and a role for Aas activity in recycling the released fatty acids. In this model, lipid degradation represents a third supply of fatty acids for lipid synthesis in cyanobacteria. PMID:20061450

  9. n-3 fatty acids from vegetable oils.

    PubMed

    Hunter, J E

    1990-05-01

    Principal food sources of the n-3 fatty acid alpha-linolenic acid are salad and cooking oil, salad dressing, shortening, margarine, and food-service fat and oil products made from canola oil or soybean oil. Using food production data provided by US trade associations and by Statistics Canada, I estimated the per capita availability of alpha-linolenic acid from vegetable-oil products in the United States to be approximately 1.2 g/d and in Canada, approximately 2 g/d. The higher alpha-linolenic acid availability in Canada is largely accounted for by widespread use of canola oil there. Considering also contributions to dietary alpha-linolenic acid of other foods such as nuts, dairy products, and vegetables, it would appear that total intake of alpha-linolenic acid in US and Canadian diets adequately exceeds the reported nutritional requirement. Emerging research has suggested possible health benefits associated with modest increases in dietary alpha-linolenic acid, including reduced blood-clotting tendency and reduced blood pressure.

  10. Liver Fatty Acid Binding Protein and Obesity

    PubMed Central

    Atshaves, B.P.; Martin, G.G.; Hostetler, H.A.; McIntosh, A.L.; Kier, A.B.; Schroeder, F.

    2010-01-01

    While low levels of unesterified long chain fatty acids (LCFAs) are normal metabolic intermediates of dietary and endogenous fat, LCFAs are also potent regulators of key receptors/enzymes, and at high levels become toxic detergents within the cell. Elevated levels of LCFAs are associated with diabetes, obesity, and metabolic syndrome. Consequently, mammals evolved fatty acid binding proteins (FABPs) that bind/sequester these potentially toxic free fatty acids in the cytosol and present them for rapid removal in oxidative (mitochondria, peroxisomes) or storage (endoplasmic reticulum, lipid droplets) organelles. Mammals have a large (15 member) family of FABPs with multiple members occurring within a single cell type. The first described FABP, liver-FABP (L-FABP, or FABP1), is expressed in very high levels (2-5% of cytosolic protein) in liver as well as intestine and kidney. Since L-FABP facilitates uptake and metabolism of LCFAs in vitro and in cultured cells, it was expected that abnormal function or loss of L-FABP would reduce hepatic LCFA uptake/oxidation and thereby increase LCFAs available for oxidation in muscle and/or storage in adipose. This prediction was confirmed in vitro with isolated liver slices and cultured primary hepatocytes from L-FABP gene-ablated mice. Despite unaltered food consumption when fed a control diet ad libitum, the L-FABP null mice exhibited age- and sex-dependent weight gain and increased fat tissue mass. The obese phenotype was exacerbated in L-FABP null mice pair-fed a high fat diet. Taken together with other findings, these data suggest that L-FABP could have an important role in preventing age- or diet-induced obesity. PMID:20537520

  11. Applications of cellular fatty acid analysis.

    PubMed Central

    Welch, D F

    1991-01-01

    More than ever, new technology is having an impact on the tools of clinical microbiologists. The analysis of cellular fatty acids by gas-liquid chromatography (GLC) has become markedly more practical with the advent of the fused-silica capillary column, computer-controlled chromatography and data analysis, simplified sample preparation, and a commercially available GLC system dedicated to microbiological applications. Experience with applications in diagnostic microbiology ranges from substantial success in work with mycobacteria, legionellae, and nonfermentative gram-negative bacilli to minimal involvement with fungi and other nonbacterial agents. GLC is a good alternative to other means for the identification of mycobacteria or legionellae because it is rapid, specific, and independent of other specialized testing, e.g., DNA hybridization. Nonfermenters show features in their cellular fatty acid content that are useful in identifying species and, in some cases, subspecies. Less frequently encountered nonfermenters, including those belonging to unclassified groups, can ideally be characterized by GLC. Information is just beginning to materialize on the usefulness of cellular fatty acids for the identification of gram-positive bacteria and anaerobes, despite the traditional role of GLC in detecting metabolic products as an aid to identification of anaerobes. When species identification of coagulase-negative staphylococci is called for, GLC may offer an alternative to biochemical testing. Methods for direct analysis of clinical material have been developed, but in practical and economic terms they are not yet ready for use in the clinical laboratory. Direct analysis holds promise for detecting markers of infection due to an uncultivable agent or in clinical specimens that presently require cultures and prolonged incubation to yield an etiologic agent. PMID:1747860

  12. [Control of adipogenesis by fatty acids].

    PubMed

    Queiroz, Jean César Farias de; Alonso-Vale, Maria Isabel Cardoso; Curi, Rui; Lima, Fabio Bessa

    2009-07-01

    Obesity is one of the major Public Health problems. Obese individuals are more susceptible to develop cardiovascular diseases and type 2 diabetes mellitus. The obesity results from the increase in size and number of the adipocytes. The balance between adipogenesis and adiposity determines the degree of obesity. Mature adipocytes secrete adipokines, such as TNFalpha, IL-6, leptine and adiponectin, and lipokine, the palmitoleic acid omega-7. The production of adipokines is increased in obesity, contributing to the onset of peripheral insulin resistance. The knowledge about the molecular events that regulate the differentiation of pre-adipocytes and mesenchymal stem cells into adipocytes (adipogenesis) is important for the comprehension of the genesis of obesity. Activation of transcription factor PPARgamma plays an essential role in the adipogenesis. Certain fatty acids are PPARgamma ligands and can control adipogenesis. Moreover, some fatty acids act as signaling molecules regulating their differentiation into adipocytes or death. Accordingly, the lipid composition of the diet and PPARgamma agonists can regulate the balance between adipogenesis and death of adipocytes and, therefore, the obesity.

  13. Serum free fatty acids level in senile cataract.

    PubMed

    Chang, Dong; Rong, Shengzhong; Zhang, Yannan; Sha, Qian; Liang, Meihua; Zhang, Xuefei; Li, Miaojing; Pan, Hongzhi

    2014-01-01

    To evaluate and compare the levels of free fatty acids between senile cataract patients and normal controls. Fifty consecutive patients with newly diagnosed senile cataract and 50 age- and gender-matched controls were evaluated. Subjects/patients were randomized according to selection criteria. The levels of free fatty acids (FFAs) in serum were measured by gas chromatography-mass spectrometry (GC-MS). Sixteen fatty acids from 14:0 to 24:1 were identified. The values were compared between cataract and control groups by parametric independent sample test and Mann-Whitney U tests. A significant decrease was observed in arachidonic acid (C20:4n-6, ARA), cis-4,7,10,13,16,19-docosahexaenoic acid (C22:6n-3, DHA), tetracosanoic acid (C24: 0), cis-7,10,13,16,19-docosapentaenoic acid (C22:5n-6, DPA), total n-3 long-chain polyunsaturated fatty acids (LC-PUFAs), total n-6 LC-PUFAs, total fatty acids, unsaturated fatty acids (USFAs), polyunsaturated fatty acids (PUFAs), and nonessential fatty acid levels in patients with senile cataract in comparison with healthy persons (p < 0.05). The levels of FFA including DPA, tetracosanoic acid, ARA, and DHA were significantly lower in the senile cataract group compared to that in the normal controls. FFA may be helpful in preventing senile cataract.

  14. Identification of Characteristic Fatty Acids to Quantify Triacylglycerols in Microalgae

    PubMed Central

    Shen, Pei-Li; Wang, Hai-Tao; Pan, Yan-Fei; Meng, Ying-Ying; Wu, Pei-Chun; Xue, Song

    2016-01-01

    The fatty acid profiles of lipids from microalgae are unique. Polyunsaturated fatty acids are generally enriched in polar lipids, whereas saturated and monounsaturated fatty acids constitute the majority of fatty acids in triacylglycerols (TAG). Each species has characteristic fatty acids, and their content is positively or negatively correlated with TAGs. The marine oleaginous diatom Phaeodactylum tricornutum was used as the paradigm to determine the quantitative relationship between TAG and characteristic fatty acid content. Fatty acid profiles and TAG content of Phaeodactylum tricornutum were determined in a time course. C16:0/C16:1 and eicosapentaenoic acid (EPA, C20:5n3) were identified as characteristic fatty acids in TAGs and polar lipids, respectively. The percentage of those characteristic fatty acids in total fatty acids had a significant linear relationship with TAG content, and thus, the correlation coefficient presenting r2 were 0.96, 0.94, and 0.97, respectively. The fatty acid-based method for TAG quantification could also be applied to other microalgae such as Nannochloropsis oceanica in which the r2 of C16:0 and EPA were 0.94 and 0.97, respectively, and in Chlorella pyrenoidosa r2-values for C18:1 and C18:3 with TAG content were 0.91 and 0.99, repectively. This characteristic fatty acid-based method provided a distinct way to quantify TAGs in microalgae, by which TAGs could be measured precisely by immediate transesterification from wet biomass rather than using conventional methods. This procedure simplified the operation and required smaller samples than conventional methods. PMID:26941747

  15. Hyperinsulinemia and skeletal muscle fatty acid trafficking.

    PubMed

    Kanaley, Jill A; Shadid, Samyah; Sheehan, Michael T; Guo, ZengKui; Jensen, Michael D

    2013-08-15

    We hypothesized that insulin alters plasma free fatty acid (FFA) trafficking into intramyocellular (im) long-chain acylcarnitines (imLCAC) and triglycerides (imTG). Overnight-fasted adults (n = 41) received intravenous infusions of [U-¹³C]palmitate (0400-0900 h) and [U-¹³C]oleate (0800-1400 h) to label imTG and imLCAC. A euglycemic-hyperinsulinemic (1.0 mU·kg fat-free mass⁻¹·min⁻¹) clamp (0800-1400 h) and two muscle biopsies (0900 h, 1400 h) were performed. The patterns of [U-¹³C]palmitate incorporation into imTG-palmitate and palmitoylcarnitine were similar to those we reported in overnight postabsorptive adults (saline control); the intramyocellular palmitoylcarnitine enrichment was not different from and correlated with imTG-palmitate enrichment for both the morning (r = 0.38, P = 0.02) and afternoon (r = 0.44, P = 0.006) biopsy samples. Plasma FFA concentrations, flux, and the incorporation of plasma oleate into imTG-oleate during hyperinsulinemia were ~1/10th of that observed in the previous saline control studies (P < 0.001). At the time of the second biopsy, the enrichment in oleoylcarnitine was <25% of that in imTG-oleate and was not correlated with imTG-oleate enrichment. The intramyocellular nonesterified fatty acid-palmitate-to-imTG-palmitate enrichment ratio was greater (P < 0.05) in women than men, suggesting that sex differences in intramyocellular palmitate trafficking may occur under hyperinsulinemic conditions. We conclude that plasma FFA trafficking into imTG during hyperinsulinemia is markedly suppressed, and these newly incorporated FFA fatty acids do not readily enter the LCAC preoxidative pools. Hyperinsulinemia does not seem to inhibit the entry of fatty acids from imTG pools that were labeled under fasting conditions, possibly reflecting the presence of two distinct imTG pools that are differentially regulated by insulin.

  16. Hyperinsulinemia and skeletal muscle fatty acid trafficking

    PubMed Central

    Kanaley, Jill A.; Shadid, Samyah; Sheehan, Michael T.; Guo, ZengKui

    2013-01-01

    We hypothesized that insulin alters plasma free fatty acid (FFA) trafficking into intramyocellular (im) long-chain acylcarnitines (imLCAC) and triglycerides (imTG). Overnight-fasted adults (n = 41) received intravenous infusions of [U-13C]palmitate (0400–0900 h) and [U-13C]oleate (0800–1400 h) to label imTG and imLCAC. A euglycemic-hyperinsulinemic (1.0 mU·kg fat-free mass−1·min−1) clamp (0800–1400 h) and two muscle biopsies (0900 h, 1400 h) were performed. The patterns of [U-13C]palmitate incorporation into imTG-palmitate and palmitoylcarnitine were similar to those we reported in overnight postabsorptive adults (saline control); the intramyocellular palmitoylcarnitine enrichment was not different from and correlated with imTG-palmitate enrichment for both the morning (r = 0.38, P = 0.02) and afternoon (r = 0.44, P = 0.006) biopsy samples. Plasma FFA concentrations, flux, and the incorporation of plasma oleate into imTG-oleate during hyperinsulinemia were ∼1/10th of that observed in the previous saline control studies (P < 0.001). At the time of the second biopsy, the enrichment in oleoylcarnitine was <25% of that in imTG-oleate and was not correlated with imTG-oleate enrichment. The intramyocellular nonesterified fatty acid-palmitate-to-imTG-palmitate enrichment ratio was greater (P < 0.05) in women than men, suggesting that sex differences in intramyocellular palmitate trafficking may occur under hyperinsulinemic conditions. We conclude that plasma FFA trafficking into imTG during hyperinsulinemia is markedly suppressed, and these newly incorporated FFA fatty acids do not readily enter the LCAC preoxidative pools. Hyperinsulinemia does not seem to inhibit the entry of fatty acids from imTG pools that were labeled under fasting conditions, possibly reflecting the presence of two distinct imTG pools that are differentially regulated by insulin. PMID:23820622

  17. Mechanisms of Gene Regulation by Fatty Acids12

    PubMed Central

    Georgiadi, Anastasia; Kersten, Sander

    2012-01-01

    Consumption of specific dietary fatty acids has been shown to influence risk and progression of several chronic diseases, such as cardiovascular disease, obesity, cancer, and arthritis. In recent years, insights into the mechanisms underlying the biological effects of fatty acids have improved considerably and have provided the foundation for the emerging concept of fatty acid sensing, which can be interpreted as the property of fatty acids to influence biological processes by serving as signaling molecules. An important mechanism of fatty acid sensing is via stimulation or inhibition of DNA transcription. Here, we focus on fatty acid sensing via regulation of gene transcription and address the role of peroxisome proliferator–activated receptors, sterol regulatory element binding protein 1, Toll-like receptor 4, G protein–coupled receptors, and other putative mediators. PMID:22516720

  18. Metabolism of fatty acids in rat brain in microsomal membranes

    SciTech Connect

    Aeberhard, E.E.; Gan-Elepano, M.; Mead, J.F.

    1980-01-01

    Using a technique in which substrate fatty acids are incorporated into microsomal membranes followd by comparison of their rates of desaturation or elongation with those of exogenous added fatty acids it has been found that the desaturation rate is more rapid for the membrane-bound substrate than for the added fatty acid. Moreover, the product of the membrane-bound substrate is incorporated into membrane phospholipid whereas the product of the exogenous substrate is found in di- and triacyl glycerols and in free fatty acids as well. These and other findings point to a normal sequence of reaction of membrane liqids with membrane-bound substrates involving transfer of fatty acid from phospholipid to the coupled enzyme systems without ready equilibration with the free fatty acid pool.

  19. Genetic engineering of fatty acid chain length in Phaeodactylum tricornutum.

    PubMed

    Radakovits, Randor; Eduafo, Patrick M; Posewitz, Matthew C

    2011-01-01

    Renewable diesel surrogates made from shorter chain length fatty acids have improved cold flow properties. Acyl-ACP thioesterases specific for shorter chain length fatty acids are therefore of considerable interest in the genetic engineering of biofuel producing organisms, both for their ability to increase the production of shorter fatty acids, and for their involvement in fatty acid secretion in bacterial systems. Here we show that the heterologous expression of two thioesterases, biased towards the production of lauric (C12:0) and myristic acid (C14:0), causes increased accumulation of shorter chain length fatty acids in the eukaryotic microalga Phaeodactylum tricornutum. Accumulation of shorter chain length fatty acids corresponds to transgene transcript levels. We achieved levels of C12:0 of up to 6.2% of total fatty acids and C14:0 of up to 15% by weight. Unlike observations in cyanobacteria, no significant secretion of fatty acids was observed. Instead, we found that 75-90% of the shorter chain length fatty acids produced was incorporated into triacylglycerols. Our results demonstrate that overexpression of thioesterases is a valid way to improve the biofuel production phenotype of eukaryotic microalgae. Copyright © 2010 Elsevier Inc. All rights reserved.

  20. 21 CFR 172.856 - Propylene glycol mono- and diesters of fats and fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... fatty acids. 172.856 Section 172.856 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH... diesters of fats and fatty acids. Propylene glycol mono- and diesters of fats and fatty acids may be safely... and/or fatty acids in compliance with § 172.860 and/or oleic acid derived from tall oil fatty acids...

  1. 21 CFR 172.856 - Propylene glycol mono- and diesters of fats and fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... and/or fatty acids in compliance with § 172.860 and/or oleic acid derived from tall oil fatty acids in... fatty acids. 172.856 Section 172.856 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH... diesters of fats and fatty acids. Propylene glycol mono- and diesters of fats and fatty acids may be...

  2. 21 CFR 172.856 - Propylene glycol mono- and diesters of fats and fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... and/or fatty acids in compliance with § 172.860 and/or oleic acid derived from tall oil fatty acids in... fatty acids. 172.856 Section 172.856 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH... diesters of fats and fatty acids. Propylene glycol mono- and diesters of fats and fatty acids may be...

  3. 21 CFR 172.856 - Propylene glycol mono- and diesters of fats and fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... and/or fatty acids in compliance with § 172.860 and/or oleic acid derived from tall oil fatty acids in... fatty acids. 172.856 Section 172.856 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH... diesters of fats and fatty acids. Propylene glycol mono- and diesters of fats and fatty acids may be...

  4. Fatty acid biosynthesis in novel ufa mutants of Neurospora crassa.

    PubMed

    Goodrich-Tanrikulu, M; Stafford, A E; Lin, J T; Makapugay, M I; Fuller, G; McKeon, T A

    1994-10-01

    New mutants of Neurospora crassa having the ufa phenotype have been isolated. Two of these mutants, like previously identified ufa mutants, require an unsaturated fatty acid for growth and are almost completely blocked in the de novo synthesis of unsaturated fatty acids. The new mutations map to a different chromosomal location than previously characterized ufa mutations. This implies that at least one additional genetic locus controls the synthesis of unsaturated fatty acids in Neurospora.

  5. Fatty acid supplements improve hair coat condition in rhesus macaques.

    PubMed

    Hamel, A F; Menard, M T; Novak, M A

    2017-05-02

    As captive rhesus macaques often exhibit hair loss, alopecia was quantified and behavior was recorded before, during, and after fatty acid supplementation in six macaques. Fatty acid treatment was associated with a decrease in alopecia and in self-grooming behavior. Therefore, fatty acids may be a viable treatment for alopecia in some captive primates. © 2017 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

  6. 40 CFR 721.10682 - Fatty acid amide hydrochlorides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amide hydrochlorides... Specific Chemical Substances § 721.10682 Fatty acid amide hydrochlorides (generic). (a) Chemical substances... fatty acid amide hydrochlorides (PMNs P-13-63, P-13-64, P-13-65, P-13-69, P-13-70, P-13-71, P-13-72,...

  7. 40 CFR 721.10323 - Glycerol fatty acid ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Glycerol fatty acid ester (generic... Specific Chemical Substances § 721.10323 Glycerol fatty acid ester (generic). (a) Chemical substance and... acid ester (PMN P-03-248) is subject to reporting under this section for the significant new...

  8. 40 CFR 721.10323 - Glycerol fatty acid ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Glycerol fatty acid ester (generic... Specific Chemical Substances § 721.10323 Glycerol fatty acid ester (generic). (a) Chemical substance and... acid ester (PMN P-03-248) is subject to reporting under this section for the significant new...

  9. 40 CFR 721.10323 - Glycerol fatty acid ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Glycerol fatty acid ester (generic... Specific Chemical Substances § 721.10323 Glycerol fatty acid ester (generic). (a) Chemical substance and... acid ester (PMN P-03-248) is subject to reporting under this section for the significant new...

  10. Cellular fatty acid composition of Actinobacillus actinomycetemcomitans and Haemophilus aphrophilus.

    PubMed Central

    Braunthal, S D; Holt, S C; Tanner, A C; Socransky, S S

    1980-01-01

    Strains of Actinobacillus actinomycetemcomitans isolated from deep pockets of patients with juvenile periodontitis were analyzed for their content of cellular fatty acids. Oral Haemophilus strains, morphologically and biochemically similar to Haemophilus aphrophilus, were also examined for their content of cellular fatty acids. The extractable lipids of the actinobacilli represented approximately 10% of the cell dry weight, with the bound lipids representing 2 to 5%. The major fatty acids consisted of myristic (C14:0) and palmitic (C16:0) acids and a C16:1 acid, possibly palmitoleic acid, accounting for 21, 35, and 31% of the total extractable fatty acids, respectively. Haemophilus strains had a similar cellular fatty acid content. PMID:7430333

  11. Polyunsaturated fatty acid inhibition of fatty acid synthase transcription is independent of PPAR activation.

    PubMed

    Clarke, S D; Turini, M; Jump, D B; Abraham, S; Reedy, M

    1998-01-01

    Polyunsaturated fatty acids (PUFA) of the (n-6) and (n-3) families inhibit the rate of gene transcription for a number of hepatic lipogenic and glycolytic genes, e.g., fatty acid synthase (FAS). In contrast, saturated and monounsaturated fatty acids have no inhibitory capability. The suppression of gene transcription resulting from the addition of PUFA to a high carbohydrate diet: occurs quickly (< 3 h) after its addition to a high glucose diet; can be recreated with hepatocytes cultured in a serum-free medium containing insulin and glucocorticoids; can be demonstrated in diabetic rats fed fructose; and is independent of glucagon. While the nature of the intracellular PUFA inhibitor is unclear, it appears that delta-6 desaturation is a required step in the process. Recently, the fatty acid activated nuclear factor, peroxisome-proliferator activated receptor (PPAR) was suggested to be the PUFA-response factor. However, the potent PPAR activators ETYA and Wy-14643 did not suppress hepatic expression of FAS, but did induce the PPAR-responsive gene, acyl-CoA oxidase (AOX). Similarly, treating rat hepatocytes with 20:4 (n-6) suppressed FAS expression but had no effect on AOX. Thus, it appears that the PUFA regulation of gene transcription involves a PUFA-response factor that is independent from PPAR.

  12. Engineering fungal de novo fatty acid synthesis for short chain fatty acid production

    PubMed Central

    Gajewski, Jan; Pavlovic, Renata; Fischer, Manuel; Boles, Eckhard; Grininger, Martin

    2017-01-01

    Fatty acids (FAs) are considered strategically important platform compounds that can be accessed by sustainable microbial approaches. Here we report the reprogramming of chain-length control of Saccharomyces cerevisiae fatty acid synthase (FAS). Aiming for short-chain FAs (SCFAs) producing baker's yeast, we perform a highly rational and minimally invasive protein engineering approach that leaves the molecular mechanisms of FASs unchanged. Finally, we identify five mutations that can turn baker's yeast into a SCFA producing system. Without any further pathway engineering, we achieve yields in extracellular concentrations of SCFAs, mainly hexanoic acid (C6-FA) and octanoic acid (C8-FA), of 464 mg l−1 in total. Furthermore, we succeed in the specific production of C6- or C8-FA in extracellular concentrations of 72 and 245 mg l−1, respectively. The presented technology is applicable far beyond baker's yeast, and can be plugged into essentially all currently available FA overproducing microorganisms. PMID:28281527

  13. Dipropionylcysteine ethyl ester compensates for loss of citric acid cycle intermediates during post ischemia reperfusion in the pig heart.

    PubMed

    Kasumov, Takhar; Sharma, Naveen; Huang, Hazel; Kombu, Rajan S; Cendrowski, Andrea; Stanley, William C; Brunengraber, Henri

    2009-12-01

    During reperfusion, following myocardial ischemia, uncompensated loss of citric acid cycle (CAC) intermediates may impair CAC flux and energy transduction. Propionate has an anaplerotic effect when converted to the CAC intermediate succinyl-CoA, and may improve contractile recovery during reperfusion. Antioxidant therapy with N-acetylcysteine decreases reperfusion injury. To synergize the antioxidant effects of cysteine with the anaplerotic effects of propionate, we synthesized a novel bi-functional compound, N,S-dipropionyl cysteine ethyl ester (DPNCE) and tested its anaplerotic and anti-oxidative capacity in anesthetized pigs. Ischemia was induced by a 70% reduction in left anterior descending coronary artery flow for one hour, followed by 1 h of reperfusion. After 30 min of ischemia and throughout reperfusion animals were treated with saline or intravenous DPNCE (1.5 mg x kg(-1) x min(-1), n = 8/group). Arterial concentrations and myocardial propionate, cysteine, free fatty acids, glucose and lactate uptakes, cardiac mechanical functions, myocardial content of CAC intermediates and oxidative stress were assessed. Ischemia resulted in reduction in myocardial tissue concentration of CAC intermediates. DPNCE treatment elevated arterial propionate and cysteine concentrations and myocardial propionate uptake, and increased myocardial concentrations of citrate, succinate, fumarate, and malate compared to saline treated animals. DPNCE treatment did not affect blood pressure or myocardial contractile function, but increased arterial free fatty acid concentration and myocardial fatty acid uptake. Arterial cysteine concentration was elevated by DPNCE, but there was negligible myocardial cysteine uptake, and no change in markers of oxidative stress. DPNCE elevated arterial cysteine and propionate, and increased myocardial concentration of CAC intermediates, but did not affect mechanical function or oxidative stress.

  14. Dietary omega-3 fatty acid intake and cardiovascular risk.

    PubMed

    Psota, Tricia L; Gebauer, Sarah K; Kris-Etherton, Penny

    2006-08-21

    Dietary omega-3 fatty acids decrease the risk of cardiovascular disease (CVD). Both epidemiologic and interventional studies have demonstrated beneficial effects of omega-3 fatty acids on many CVD end points, including all CVD (defined as all coronary artery disease [CAD], fatal and nonfatal myocardial infarction [MI], and stroke combined), all CAD, fatal and nonfatal MI, stroke, sudden cardiac death, and all-cause mortality. Much of the evidence comes from studies with fish oil and fish; to a lesser extent, data relate to plant-derived omega-3 fatty acids. Cardioprotective benefits have been observed with daily consumption of as little as 25 to 57 g (approximately 1 to 2 oz) of fish high in omega-3 fatty acids, an intake equivalent to >or=1 fish meal weekly or even monthly, with greater intakes decreasing risk further in a dose-dependent manner, up to about 5 servings per week. Fish, including farm-raised fish and their wild counterparts, are the major dietary sources of the longer-chain omega-3 fatty acids. Sources of plant-derived omega-3 fatty acids include flaxseed, flaxseed oil, walnuts, canola oil, and soybean oil. Because of the remarkable cardioprotective effects of omega-3 fatty acids, consumption of food sources that provide omega-3 fatty acids--especially the longer-chain fatty acids (>or=20 carbons) from marine sources--should be increased in the diet to decrease CVD risk significantly.

  15. Algal swimming velocities signal fatty acid accumulation.

    PubMed

    Hansen, Travis J; Hondzo, Miki; Mashek, Mara T; Mashek, Douglas G; Lefebvre, Paul A

    2013-01-01

    The use of microalgae for biofuel production will be beneficial to society if we can produce biofuels at large scales with minimal mechanical energy input in the production process. Understanding micro-algal physiological responses under variable environmental conditions in bioreactors is essential for the optimization of biofuel production. We demonstrate that measuring micro-algal swimming speed provides information on culture health and total fatty acid accumulation. Three strains of Chlamydomonas reinhardtii were grown heterotrophically on acetate and subjected to various levels of nitrogen starvation. Other nutrient levels were explored to determine their effect on micro-algal kinetics. Swimming velocities were measured with two-dimensional micro-particle tracking velocimetry. The results show an inverse linear relationship between normalized total fatty acid mass versus swimming speed of micro-algal cells. Analysis of RNA sequencing data confirms these results by demonstrating that the biological processes of cell motion and the generation of energy precursors are significantly down-regulated. Experiments demonstrate that changes in nutrient concentration in the surrounding media also affect swimming speed. The findings have the potential for the in situ and indirect assessment of lipid content by measuring micro-algal swimming kinetics.

  16. Antiarrhythmic effects of omega-3 fatty acids.

    PubMed

    Reiffel, James A; McDonald, Arline

    2006-08-21

    Fish oil, and omega-3 fatty acids in particular, have been found to reduce plasma levels of triglycerides and increase levels of high-density lipoprotein in patients with marked hypertriglyceridemia, and a pharmaceutical-grade preparation has recently received approval from the US Food and Drug Administration to market for this purpose. However, in both bench research studies and clinical trials, evidence for clinically significant antiarrhythmic properties has also been detected in association with omega-3 fatty acid intake. Arguably the most significant finding in this data set was the reduction in the incidence of sudden death in survivors of myocardial infarction in the Gruppo Italiano per lo Studio della Sopravvivenza nell'Infarto Miocardico (GISSI)-Prevenzione trial and the subsequent recommendation for administration of fish oil as part of the postinfarction regimen in Europe. This article reviews in detail the basic and clinical research studies of fish oil as an antiarrhythmic entity, the forms of preparation and/or administration that appear to possess these properties and those that do not, the types of arrhythmias (ventricular ectopy and atrial fibrillation as well as ventricular tachyarrhythmias) that have been beneficially affected by fish oil administration, and the presumed and known mechanisms by which the beneficial actions are exerted.

  17. Acetylenes and fatty acids from Codonopsis pilosula

    PubMed Central

    Jiang, Yueping; Liu, Yufeng; Guo, Qinglan; Jiang, Zhibo; Xu, Chengbo; Zhu, Chenggen; Yang, Yongchun; Lin, Sheng; Shi, Jiangong

    2015-01-01

    Four new acetylenes (1–4) and one new unsaturated ω-hydroxy fatty acid (5), together with 5 known analogues, were isolated from an aqueous extract of Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods. The new acetylenes are categorized as an unusual cyclotetradecatrienynone (1), tetradecenynetriol (2), and rare octenynoic acids (3 and 4), respectively, and 3 and 4 are possibly derived from oxidative metabolic degradation of 1 and/or 2. The absolute configuration of 1 was assigned by comparison of the experimental circular dichroism (CD) spectrum with the calculated electronic circular dichroism (ECD) spectra of stereoisomers based on the quantum-mechanical time-dependent density functional theory, while the configuration of 2 was assigned by using modified Mosher׳s method based on the MPA determination rule of ΔδRS values for diols. PMID:26579449

  18. Effects of fatty acid activation on photosynthetic production of fatty acid-based biofuels in Synechocystis sp. PCC6803

    PubMed Central

    2012-01-01

    Background Direct conversion of solar energy and carbon dioxide to drop in fuel molecules in a single biological system can be achieved from fatty acid-based biofuels such as fatty alcohols and alkanes. These molecules have similar properties to fossil fuels but can be produced by photosynthetic cyanobacteria. Results Synechocystis sp. PCC6803 mutant strains containing either overexpression or deletion of the slr1609 gene, which encodes an acyl-ACP synthetase (AAS), have been constructed. The complete segregation and deletion in all mutant strains was confirmed by PCR analysis. Blocking fatty acid activation by deleting slr1609 gene in wild-type Synechocystis sp. PCC6803 led to a doubling of the amount of free fatty acids and a decrease of alkane production by up to 90 percent. Overexpression of slr1609 gene in the wild-type Synechocystis sp. PCC6803 had no effect on the production of either free fatty acids or alkanes. Overexpression or deletion of slr1609 gene in the Synechocystis sp. PCC6803 mutant strain with the capability of making fatty alcohols by genetically introducing fatty acyl-CoA reductase respectively enhanced or reduced fatty alcohol production by 60 percent. Conclusions Fatty acid activation functionalized by the slr1609 gene is metabolically crucial for biosynthesis of fatty acid derivatives in Synechocystis sp. PCC6803. It is necessary but not sufficient for efficient production of alkanes. Fatty alcohol production can be significantly improved by the overexpression of slr1609 gene. PMID:22433663

  19. High dose eicosapentaenoic acid ethyl ester: effects on lipids and neutrophil leukotriene production in normal volunteers.

    PubMed Central

    Hawthorne, A B; Filipowicz, B L; Edwards, T J; Hawkey, C J

    1990-01-01

    1. A 93% pure ethyl ester of eicosapentaenoic acid was investigated for tolerability and biochemical effects on neutrophil leukotriene synthesis and plasma lipoproteins when given in high dose. Six healthy volunteers received 6 g eicosapentaenoic acid ethyl ester daily for 6 weeks, followed by a 4 week wash-out and then 18 g daily for 6 weeks. 2. There was inhibition of neutrophil leukotriene B4 and 5-hydroxyeicosatetraenoic acid synthesis, with no significant differences between low and high dose. 3. There was a dose dependent increase in leukotriene B5 and 5-hydroxyeicosatetraenoic acid acid synthesis. 4. Plasma triglycerides were reduced maximally on 6 g daily, with no greater suppression at 18 g daily. 5. Plasma cholesterol was only suppressed significantly at 18 g daily. 6. The 6 g daily dose was well tolerated but the 18 g daily dose produced diarrhoea and steatorrhoea. PMID:2169832

  20. Fatty acids profiling reveals potential candidate markers of semen quality.

    PubMed

    Zerbinati, C; Caponecchia, L; Rago, R; Leoncini, E; Bottaccioli, A G; Ciacciarelli, M; Pacelli, A; Salacone, P; Sebastianelli, A; Pastore, A; Palleschi, G; Boccia, S; Carbone, A; Iuliano, L

    2016-11-01

    Previous reports showed altered fatty acid content in subjects with altered sperm parameters compared to normozoospermic individuals. However, these studies focused on a limited number of fatty acids, included a short number of subjects and results varied widely. We conducted a case-control study involving 155 patients allocated into four groups, including normozoospermia (n = 33), oligoasthenoteratozoospermia (n = 32), asthenozoospermia (n = 25), and varicocoele (n = 44). Fatty acid profiling, including 30 species, was analyzed by a validated gas chromatography (GC) method on the whole seminal fluid sample. Multinomial logistic regression modeling was used to identify the associations between fatty acids and the four groups. Specimens from 15 normozoospermic subjects were also analyzed for fatty acids content in the seminal plasma and spermatozoa to study the distribution in the two compartments. Fatty acids lipidome varied markedly between the four groups. Multinomial logistic regression modeling revealed that high levels of palmitic acid, behenic acid, oleic acid, and docosahexaenoic acid (DHA) confer a low risk to stay out of the normozoospermic group. In the whole population, seminal fluid stearic acid was negatively correlated (r = -0.53), and DHA was positively correlated (r = 0.65) with sperm motility. Some fatty acids were preferentially accumulated in spermatozoa and the highest difference was observed for DHA, which was 6.2 times higher in spermatozoa than in seminal plasma. The results of this study highlight complete fatty acids profile in patients with different semen parameters. Given the easy-to-follow and rapid method of analysis, fatty acid profiling by GC method can be used for therapeutic purposes and to measure compliance in infertility trials using fatty acids supplements. © 2016 American Society of Andrology and European Academy of Andrology.

  1. [Raman spectrometry of several saturated fatty acids and their salts].

    PubMed

    Luo, Man; Guan, Ping; Liu, Wen-hui; Liu, Yan

    2006-11-01

    Saturated fatty acids and their salts widely exist in the nature, and they are well known as important chemical materials. Their infrared spectra have been studied in detail. Nevertheless, few works on the Raman spectra characteristics of saturated fatty acids and their salts have been published before. Man-made crystals of acetic acid, stearic acid, calcium acetate, magnesium acetate, calcium stearate and magnesium stearate were investigated by means of Fourier transform Raman spectrometry for purpose of realizing their Raman spectra. Positive ions can cause the distinctions between the spectra of saturated fatty acids and their salts. The differences in mass and configuration between Ca2+ and Mg2+ result in the Raman spectra's diversity between calcium and magnesium salts of saturated fatty acids. Meanwhile, it is considered that the long carbon chain weakened the influence of different positive ions on the salts of saturated fatty acids.

  2. Resolution and quantification of isomeric fatty acids by silver ion HPLC: fatty acid composition of aniseed oil (Pimpinella anisum, Apiaceae).

    PubMed

    Denev, Roumen V; Kuzmanova, Ivalina S; Momchilova, Svetlana M; Nikolova-Damyanova, Boryana M

    2011-01-01

    A silver ion HPLC procedure is described that is suitable to determine the fatty acid composition of plant seed oils. After conversion of fatty acids to p-methoxyphenacyl derivatives, it was possible to achieve baseline resolution of all fatty acid components with 0 to 3 double bonds, including the positionally isomeric 18:1 fatty acids oleic acid (cis 9-18:1), petroselinic acid (cis 6-18:1), and cis-vaccenic acid (cis 11-18:1), in aniseed oil (Pimpinella anisum, Apiaceae) by a single gradient run on a single cation exchange column laboratory converted to the silver ion form. The UV detector response (280 nm) was linearly related to the fatty acid concentration in the range 0.01 to 3.5 mg/mL.

  3. Overproduction of fatty acids in engineered Saccharomyces cerevisiae.

    PubMed

    Li, Xiaowei; Guo, Daoyi; Cheng, Yongbo; Zhu, Fayin; Deng, Zixin; Liu, Tiangang

    2014-09-01

    The long hydrocarbon fatty acyl chain is energy rich, making it an ideal precursor for liquid transportation fuels and high-value oleo chemicals. As Saccharomyces cerevisiae has many advantages for industrial production compared to Escherichia coli. Here, we attempted to engineer Saccharomyces cerevisiae for overproduction of fatty acids. First, disruption of the beta-oxidation pathway, elimination of the acyl-CoA synthetases, overexpression of different thioesterases and acetyl-CoA carboxylase ACC1, and engineering the supply of precursor acetyl-CoA. The engineered strain XL122 produced more than 120 mg/L of fatty acids. In parallel, we inactivated ADH1, the dominant gene for ethanol production, to redirect the metabolic flux to fatty acids synthesis. The engineered strain DG005 produced about 140 mg/L fatty acids. Additionally, Acetyl-CoA carboxylase was identified as a critical bottleneck of fatty acids synthesis in S. cerevisiae with a cell-free system. However, overexpression of ACC1 has little effect on fatty acids biosynthesis. As it has been reported that phosphorylation of ACC1 may influent its activity, so phosphorylation sites of ACC1 were further identified. Although the regulatory mechanisms remain unclear, our results provide rationale for future studies to target this critical step. All these efforts, particularly the discovery of the limiting step are critical for developing a "cell factory" for the overproduction of fatty acids by using type I fatty acids synthase in yeast or other fungi.

  4. 40 CFR 721.10064 - 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... permissible. (ii) Hazard communication program. Requirements as specified in § 721.72 (a), (b), (c), (d), (f... Substances § 721.10064 2-Propenoic acid, 2- ethyl ester. (a) Chemical substance and significant new uses... described in paragraph (a)(2) of this section. (2) The significant new uses are: (i) Protection in the...

  5. Premixed ignition behavior of C{sub 9} fatty acid esters: A motored engine study

    SciTech Connect

    Zhang, Yu.; Yang, Yi; Boehman, Andre L.

    2009-06-15

    An experimental study on the premixed ignition behavior of C{sub 9} fatty acid esters has been conducted in a motored CFR engine. For each test fuel, the engine compression ratio was gradually increased from the lowest point (4.43) to the point where significant high temperature heat release (HTHR) was observed. The engine exhaust was sampled and analyzed through GC-FID/TCD and GC-MS. Combustion analysis showed that the four C{sub 9} fatty acid esters tested in this study exhibited evidently different ignition behavior. The magnitude of low temperature heat release (LTHR) follows the order, ethyl nonanoate > methyl nonanoate >> methyl 2-nonenoate > methyl 3-nonenoate. The lower oxidation reactivity for the unsaturated fatty acid esters in the low temperature regime can be explained by the reduced amount of six- or seven-membered transition state rings formed during the oxidation of the unsaturated esters due to the presence of a double bond in the aliphatic chain of the esters. The inhibition effect of the double bond on the low temperature oxidation reactivity of fatty acid esters becomes more pronounced as the double bond moves toward the central position of the aliphatic chain. GC-MS analysis of exhaust condensate collected under the engine conditions where only LTHR occurred showed that the alkyl chain of the saturated fatty acid esters participated in typical paraffin-like low temperature oxidation sequences. In contrast, for unsaturated fatty acid esters, the autoignition can undergo olefin ignition pathways. For all test compounds, the ester functional group remains largely intact during the early stage of oxidation. (author)

  6. Conversion of furfuryl alcohol into ethyl levulinate using solid acid catalysts.

    PubMed

    Lange, Jean-Paul; van de Graaf, Wouter D; Haan, René J

    2009-01-01

    Furfural, a potential coproduct of levulinic acid, can be converted into levulinic acid via hydrogenation to furfuryl alcohol and subsequent ethanolysis to ethyl levulinate. The ethanolysis reaction is known to proceed in the presence of H(2)SO(4). We show here that several strongly acidic resins are comparably effective catalysts for this reaction. Optimal performance is achieved by balancing the number of acid sites with their accessibility in the resin. Acidic zeolites such as H-ZSM-5 also catalyze this reaction, although with a lower activity and a higher co-production of diethyl ether.

  7. Polyunsaturated fatty acids and inflammatory diseases.

    PubMed

    Gil, A

    2002-10-01

    Inflammation is overall a protective response, whose main goal is to liberate the human being of cellular lesions caused by micro-organisms, toxins, allergens, etc., as well as its consequences, and of death cells and necrotic tissues. Chronic inflammation, which is detrimental to tissues, is the basic pathogenic mechanism of hypersensitivity reactions against xenobiotics. Other frequent pathologies, for instance atherosclerosis, chronic hepatitis, inflammatory bowel disease (IBD), liver cirrhosis, lung fibrosis, psoriasis, and rheumatoid arthritis are also chronic inflammatory diseases. Chemical mediators of inflammation are derived from blood plasma or different cell-type activity. Biogenic amines, eicosanoids and cytokines are within the most important mediators of inflammatory processes. The different activities of eicosanoids derived from arachidonic acid (20:4 n-6) versus those derived from eicosapentaenoic acid (20:5 n-3) are one of the most important mechanisms to explain why n-3, or omega-3, polyunsaturated fatty acids (PUFA) exhibit anti-inflammatory properties in many inflammatory diseases. Dietary supplements ranging 1-8 g per day of n-3 PUFA have been reportedly beneficial in the treatment of IBD, eczema, psoriasis and rheumatoid arthritis. In addition, recent experimental studies in rats with experimental ulcerative colitis, induced by intrarectal injection of trinitrobenzene sulphonic acid, have documented that treatment with n-3 long-chain PUFA reduces mucosal damage as assessed by biochemical and histological markers of inflammation. Moreover, the defence antioxidant system in this model is enhanced in treated animals, provided that the n-3 PUFA supply is adequately preserved from oxidation.

  8. [Possible route for thiamine participation in fatty acid synthesis].

    PubMed

    Buko, V U; Larin, F S

    1976-01-01

    The possibility of thiamine partaking in the synthesis of fatty acids through the functions unrelated to the catalytic properties of thiamine-diphosphate was studied. Rats kept on a fat-free ration devoid of thiamine were given thiamine of thiochrome with no vitaminic properties. The total fatty acids content in different tissues and incorporation therein of tagged acetate and pyruvate was determined, while the fatty acids composition of the liver was investigated by using gas chromatography. Thiamine and thiochrome produced a similar effect on a number of the study factors, i.e. they forced down the total acids level in the spleen, intensified incorporation of tagged acetate and pyruvate in fatty acids of the heart and uniformly changed the fatty acids composition in the liver. It is suggested that the unindirectional effects of thiamine and thiochrome is due to the oxidative transformation of thiamine into thiochrome.

  9. [Fat and fatty acids chosen in chocolates content].

    PubMed

    Tarkowski, Andrzej; Kowalczyk, Magdalena

    2007-01-01

    The objective of present work was to comparison of fat and chosen fatty acid in chocolates with, approachable on national market. In the investigations on fat and fatty acids content in the milk chocolates, there were used 14 chocolates, divided into 3 groups either without, with supplements and stuffing. Crude fat content in the chocolates was determined on Soxhlet automatic apparatus. The saturated ad nsaturated acids content was determined using gas chromatographic method. Content of fat and fatty cids in chocolates were differentiation. The highest crude fat content was finding in chocolates with tuffing (31.8%) and without supplements (28.9%). The sum of saturated fatty acids content in fat above 62%) was highest and low differentiation in the chocolates without supplements. Among of saturated and unsaturated fatty acids depended from kind of chocolates dominated, palmitic, stearic, oleic and, linoleic acids. Supplements of nut in chocolates had on influence of high oleic and linoleic level

  10. Sex Steroid Modulation of Fatty Acid Utilization and Fatty Acid Binding Protein Concentration in Rat Liver

    PubMed Central

    Ockner, Robert K.; Lysenko, Nina; Manning, Joan A.; Monroe, Scott E.; Burnett, David A.

    1980-01-01

    The mechanism by which sex steroids influence very low density hepatic lipoprotein triglyceride production has not been fully elucidated. In previous studies we showed that [14C]oleate utilization and incorporation into triglycerides were greater in hepatocyte suspensions from adult female rats than from males. The sex differences were not related to activities of the enzymes of triglyceride biosynthesis, whereas fatty acid binding protein (FABP) concentration in liver cytosol was greater in females. These findings suggested that sex differences in lipoprotein could reflect a sex steroid influence on the availability of fatty acids for hepatocellular triglyceride biosynthesis. In the present studies, sex steroid effects on hepatocyte [14C]oleate utilization and FABP concentration were investigated directly. Hepatocytes from immature (30-d-old) rats exhibited no sex differences in [14C]oleate utilization. With maturation, total [14C]oleate utilization and triglyceride biosynthesis increased moderately in female cells and decreased markedly in male cells; the profound sex differences in adults were maximal by age 60 d. Fatty acid oxidation was little affected. Rats were castrated at age 30 d, and received estradiol, testosterone, or no hormone until age 60 d, when hepatocyte [14C]oleate utilization was studied. Castration virtually eliminated maturational changes and blunted the sex differences in adults. Estradiol or testosterone largely reproduced the appropriate adult pattern of [14C]oleate utilization regardless of the genotypic sex of the treated animal. In immature females and males, total cytosolic FABP concentrations were similar. In 60-d-old animals, there was a striking correlation among all groups (females, males, castrates, and hormone-treated) between mean cytosolic FABP concentration on the one hand, and mean total [14C]oleate utilization (r = 0.91) and incorporation into triglycerides (r = 0.94) on the other. In 30-d-old animals rates of [14C

  11. Continuous lipase-catalyzed esterification of soybean fatty acids under ultrasound irradiation.

    PubMed

    Trentin, Claudia M; Scherer, Robison P; Dalla Rosa, C; Treichel, H; Oliveira, D; Oliveira, J Vladimir

    2014-05-01

    This work investigates the continuous production of alkyl esters from soybean fatty acid (FA) charges using immobilized Novozym 435 as catalyst. The experiments were performed in a packed-bed bioreactor evaluating the effects of FA charge to alcohol (methanol and ethanol) molar ratio, from 1:1 to 1:6, substrate flow rate in the range of 0.5-2.5 mL/min and output irradiation power up to 154 W, at fixed temperature of 65 °C, on the reaction conversion. Results showed that almost complete conversions to fatty acids ethyl esters were achieved at mild ultrasonic power (61.6 W), FA to ethanol molar ratio of 1:6, operating temperature (65 °C) and remained nearly constant for long-term reactions without negligible enzyme activity losses.

  12. Fatty acid composition of two Tunisian pine seed oils.

    PubMed

    Nasri, Nizar; Khaldi, Abdelhamid; Hammami, Mohamed; Triki, Saida

    2005-01-01

    Oils were extracted from fully ripen Pinus pinea L. and Pinus halepensis Mill seeds and fatty acid composition has been established by capillary gas chromatography. Seeds are rich in lipids, 34.63-48.12% on a dry weight basis. Qualitatively, fatty acid composition of both species is identical. For P. halepensis linoleic acid is the major fatty acid (56.06% of total fatty acids) followed by oleic (24.03%) and palmitic (5.23%) acids. For P. pinea, the same fatty acids are found with the proportions 47.28%, 36.56%, and 6.67%, respectively. Extracted fatty acids from both species are mainly unsaturated, respectively, 89.87% and 88.01%. Pinus halepensis cis-5 olefinic acids are more abundant (7.84% compared to 2.24%). Results will be important as a good indication of the potential nutraceutical value of Pinus seeds as new sources of fruit oils rich in polyunsaturated fatty acids and cis-5 olefinic acids.

  13. Omega-3 Fatty Acids in the Management of Epilepsy.

    PubMed

    Tejada, Silvia; Martorell, Miquel; Capó, Xavier; Tur, Josep A; Pons, Antoni; Sureda, Antoni

    2016-01-01

    Omega-3 and omega-6 fatty acids are polyunsaturated fatty acids (PUFAs) with multiple double bonds. Linolenic and alpha-linolenic acids are omega-6 and omega-3 PUFAs, precursors for the synthesis of long-chain PUFAs (LC-PUFAs), such as arachidonic acid (omega-6 PUFA), and eicosapentaenoic and docosahexaenoic acids (omega-3 PUFAs). The three most important omega-3 fatty acids are alpha-linolenic, eicosapentaenoic and docosahexaenoic acids, which cannot be synthesized in enough amounts by the body, and therefore they must be supplied by the diet. Omega-3 fatty acids are essential for the correct functioning of the organism and participate in many physiological processes in the brain. Epilepsy is a common and heterogeneous chronic brain disorder characterized by recurrent epileptic seizures leading to neuropsychiatric disabilities. The prevalence of epilepsy is high achieving about 1% of the general population. There is evidence suggesting that omega-3 fatty acids may have neuroprotective and anticonvulsant effects and, accordingly, may have a potential use in the treatment of epilepsy. In the present review, the potential use of omega-3 fatty acids in the treatment of epilepsy, and the possible proposed mechanisms of action are discussed. The present article summarizes the recent knowledge of the potential protective role of dietary omega-3 fatty acids in epilepsy.

  14. Sources and Bioactive Properties of Conjugated Dietary Fatty Acids.

    PubMed

    Hennessy, Alan A; Ross, Paul R; Fitzgerald, Gerald F; Stanton, Catherine

    2016-04-01

    The group of conjugated fatty acids known as conjugated linoleic acid (CLA) isomers have been extensively studied with regard to their bioactive potential in treating some of the most prominent human health malignancies. However, CLA isomers are not the only group of potentially bioactive conjugated fatty acids currently undergoing study. In this regard, isomers of conjugated α-linolenic acid, conjugated nonadecadienoic acid and conjugated eicosapentaenoic acid, to name but a few, have undergone experimental assessment. These studies have indicated many of these conjugated fatty acid isomers commonly possess anti-carcinogenic, anti-adipogenic, anti-inflammatory and immune modulating properties, a number of which will be discussed in this review. The mechanisms through which these bioactivities are mediated have not yet been fully elucidated. However, existing evidence indicates that these fatty acids may play a role in modulating the expression of several oncogenes, cell cycle regulators, and genes associated with energy metabolism. Despite such bioactive potential, interest in these conjugated fatty acids has remained low relative to the CLA isomers. This may be partly attributed to the relatively recent emergence of these fatty acids as bioactives, but also due to a lack of awareness regarding sources from which they can be produced. In this review, we will also highlight the common sources of these conjugated fatty acids, including plants, algae, microbes and chemosynthesis.

  15. Beta cell compensation for insulin resistance in Zucker fatty rats: increased lipolysis and fatty acid signalling.

    PubMed

    Nolan, C J; Leahy, J L; Delghingaro-Augusto, V; Moibi, J; Soni, K; Peyot, M-L; Fortier, M; Guay, C; Lamontagne, J; Barbeau, A; Przybytkowski, E; Joly, E; Masiello, P; Wang, S; Mitchell, G A; Prentki, M

    2006-09-01

    The aim of this study was to determine the role of fatty acid signalling in islet beta cell compensation for insulin resistance in the Zucker fatty fa/fa (ZF) rat, a genetic model of severe obesity, hyperlipidaemia and insulin resistance that does not develop diabetes. NEFA augmentation of insulin secretion and fatty acid metabolism were studied in isolated islets from ZF and Zucker lean (ZL) control rats. Exogenous palmitate markedly potentiated glucose-stimulated insulin secretion (GSIS) in ZF islets, allowing robust secretion at physiological glucose levels (5-8 mmol/l). Exogenous palmitate also synergised with glucagon-like peptide-1 and the cyclic AMP-raising agent forskolin to enhance GSIS in ZF islets only. In assessing islet fatty acid metabolism, we found increased glucose-responsive palmitate esterification and lipolysis processes in ZF islets, suggestive of enhanced triglyceride-fatty acid cycling. Interruption of glucose-stimulated lipolysis by the lipase inhibitor Orlistat (tetrahydrolipstatin) blunted palmitate-augmented GSIS in ZF islets. Fatty acid oxidation was also higher at intermediate glucose levels in ZF islets and steatotic triglyceride accumulation was absent. The results highlight the potential importance of NEFA and glucoincretin enhancement of insulin secretion in beta cell compensation for insulin resistance. We propose that coordinated glucose-responsive fatty acid esterification and lipolysis processes, suggestive of triglyceride-fatty acid cycling, play a role in the coupling mechanisms of glucose-induced insulin secretion as well as in beta cell compensation and the hypersecretion of insulin in obesity.

  16. Site-selective Alkane Dehydrogenation of Fatty Acids

    DTIC Science & Technology

    2011-12-14

    dehydrogenation of fatty acids Contract/Grant#: FA9550-10-1-0532 Final Reporting Period: 15 September 2011 to 14 September 2011...directly incorporate fatty acids into the ligand. The preparation of the acyl phosphines (1-5) was easily accomplished starting from the corresponding...AFOSR Final Report Final Report 
 The proposed research examines the site-selective dehydrogenation of alkanes. The alkanes employed were fatty

  17. Membrane Stresses Induced by Overproduction of Free Fatty Acids in Escherichia coli.

    SciTech Connect

    Lennen, Rebecca M.; Kruziki, Max A.; Kumar, Kritika; Zinkel, Robert A.; Burnum, Kristin E.; Lipton, Mary S.; Hoover, Spencer W.; Ranatunga, Don Ruwan; Wittkopp, Tyler M.; Marner II, Wesley D.; Pfleger, Brian F.

    2011-11-01

    Microbially produced fatty acids are potential precursors to high energy density biofuels, including alkanes and alkyl ethyl esters by either catalytic conversion of free fatty acids (FFAs) or enzymatic conversions of acyl-acyl carrier protein or acyl-coenzyme A intermediates. Metabolic engineering efforts aimed at overproducing FFAs in Escherichia coli have achieved less than 30% of the maximum theoretical yield on the supplied carbon source. In this work, the viability, morphology, transcript levels, and protein levels of a strain of E. coli that overproduces medium chain length FFAs was compared to an engineered control strain. By early stationary phase, an 85% reduction in viable cell counts and exacerbated loss of inner membrane integrity were observed in the FFA overproducing strain. These effects were enhanced in strains endogenously producing FFAs compared to strains exposed to exogenously fed FFAs. Under two sets of cultivation conditions, long chain unsaturated fatty acid content greatly increased and the expression of genes and proteins required for unsaturated fatty acid biosynthesis were significantly decreased. Membrane stresses were further implicated by increased expression of genes and proteins of the phage shock response, the MarA/Rob/SoxS regulon, and the nuo and cyo operons of aerobic respiration. Gene deletion studies confirmed the importance of the phage shock proteins and Rob for maintaining cell viability, however little to no change in FFA titers was observed after 24 h cultivation. The results of this study serve as a baseline for future targeted attempts to improve FFA yields and titers in E. coli.

  18. Fatty acid-amino acid conjugates diversification in lepidopteran caterpillars.

    PubMed

    Yoshinaga, Naoko; Alborn, Hans T; Nakanishi, Tomoaki; Suckling, David M; Nishida, Ritsuo; Tumlinson, James H; Mori, Naoki

    2010-03-01

    Fatty acid amino acid conjugates (FACs) have been found in noctuid as well as sphingid caterpillar oral secretions; in particular, volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and its biochemical precursor, N-linolenoyl-L-glutamine, are known elicitors of induced volatile emissions in corn plants. These induced volatiles, in turn, attract natural enemies of the caterpillars. In a previous study, we showed that N-linolenoyl-L-glutamine in larval Spodoptera litura plays an important role in nitrogen assimilation which might be an explanation for caterpillars synthesizing FACs despite an increased risk of attracting natural enemies. However, the presence of FACs in lepidopteran species outside these families of agricultural interest is not well known. We conducted FAC screening of 29 lepidopteran species, and found them in 19 of these species. Thus, FACs are commonly synthesized through a broad range of lepidopteran caterpillars. Since all FAC-containing species had N-linolenoyl-L-glutamine and/or N-linoleoyl-L-glutamine in common, and the evolutionarily earliest species among them had only these two FACs, these glutamine conjugates might be the evolutionarily older FACs. Furthermore, some species had glutamic acid conjugates, and some had hydroxylated FACs. Comparing the diversity of FACs with lepidopteran phylogeny indicates that glutamic acid conjugates can be synthesized by relatively primitive species, while hydroxylation of fatty acids is limited mostly to larger and more developed macrolepidopteran species.

  19. Modulating fatty acid oxidation in heart failure

    PubMed Central

    Lionetti, Vincenzo; Stanley, William C.; Recchia, Fabio A.

    2011-01-01

    In the advanced stages of heart failure, many key enzymes involved in myocardial energy substrate metabolism display various degrees of down-regulation. The net effect of the altered metabolic phenotype consists of reduced cardiac fatty oxidation, increased glycolysis and glucose oxidation, and rigidity of the metabolic response to changes in workload. Is this metabolic shift an adaptive mechanism that protects the heart or a maladaptive process that accelerates structural and functional derangement? The question remains open; however, the metabolic remodelling of the failing heart has induced a number of investigators to test the hypothesis that pharmacological modulation of myocardial substrate utilization might prove therapeutically advantageous. The present review addresses the effects of indirect and direct modulators of fatty acid (FA) oxidation, which are the best pharmacological agents available to date for ‘metabolic therapy’ of failing hearts. Evidence for the efficacy of therapeutic strategies based on modulators of FA metabolism is mixed, pointing to the possibility that the molecular/biochemical alterations induced by these pharmacological agents are more complex than originally thought. Much remains to be understood; however, the beneficial effects of molecules such as perhexiline and trimetazidine in small clinical trials indicate that this promising therapeutic strategy is worthy of further pursuit. PMID:21289012

  20. Modulating fatty acid oxidation in heart failure.

    PubMed

    Lionetti, Vincenzo; Stanley, William C; Recchia, Fabio A

    2011-05-01

    In the advanced stages of heart failure, many key enzymes involved in myocardial energy substrate metabolism display various degrees of down-regulation. The net effect of the altered metabolic phenotype consists of reduced cardiac fatty oxidation, increased glycolysis and glucose oxidation, and rigidity of the metabolic response to changes in workload. Is this metabolic shift an adaptive mechanism that protects the heart or a maladaptive process that accelerates structural and functional derangement? The question remains open; however, the metabolic remodelling of the failing heart has induced a number of investigators to test the hypothesis that pharmacological modulation of myocardial substrate utilization might prove therapeutically advantageous. The present review addresses the effects of indirect and direct modulators of fatty acid (FA) oxidation, which are the best pharmacological agents available to date for 'metabolic therapy' of failing hearts. Evidence for the efficacy of therapeutic strategies based on modulators of FA metabolism is mixed, pointing to the possibility that the molecular/biochemical alterations induced by these pharmacological agents are more complex than originally thought. Much remains to be understood; however, the beneficial effects of molecules such as perhexiline and trimetazidine in small clinical trials indicate that this promising therapeutic strategy is worthy of further pursuit.

  1. Incorporated fish oil fatty acids prevent action potential shortening induced by circulating fish oil fatty acids.

    PubMed

    Den Ruijter, Hester M; Verkerk, Arie O; Coronel, Ruben

    2010-01-01

    Increased consumption of fatty fish, rich in omega-3-polyunsaturated fatty acids (ω3-PUFAs) reduces the severity and number of arrhythmias. Long-term ω3-PUFA-intake modulates the activity of several cardiac ion channels leading to cardiac action potential shortening. Circulating ω3-PUFAs in the bloodstream and incorporated ω3-PUFAs in the cardiac membrane have a different mechanism to shorten the action potential. It is, however, unknown whether circulating ω3-PUFAs in the bloodstream enhance or diminish the effects of incorporated ω3-PUFAs. In the present study, we address this issue. Rabbits were fed a diet rich in fish oil (ω3) or sunflower oil (ω9, as control) for 3 weeks. Ventricular myocytes were isolated by enzymatic dissociation and action potentials were measured using the perforated patch-clamp technique in the absence and presence of acutely administered ω3-PUFAs. Plasma of ω3 fed rabbits contained more free eicosapentaenoic acid (EPA) and isolated myocytes of ω3 fed rabbits contained higher amounts of both EPA and docosahexaenoic acid (DHA) in their sarcolemma compared to control. In the absence of acutely administered fatty acids, ω3 myocytes had a shorter action potential with a more negative plateau than ω9 myocytes. In the ω9 myocytes, but not in the ω3 myocytes, acute administration of a mixture of EPA + DHA shortened the action potential significantly. From these data we conclude that incorporated ω3-PUFAs into the sarcolemma and acutely administered ω3 fatty acids do not have a cumulative effect on action potential duration and morphology. As a consequence, patients with a high cardiac ω3-PUFA status will probably not benefit from short term ω3 supplementation as an antiarrhythmic therapy.

  2. Incorporated Fish Oil Fatty Acids Prevent Action Potential Shortening Induced by Circulating Fish Oil Fatty Acids

    PubMed Central

    Ruijter, Hester M. Den; Verkerk, Arie O.; Coronel, Ruben

    2010-01-01

    Increased consumption of fatty fish, rich in omega-3-polyunsaturated fatty acids (ω3-PUFAs) reduces the severity and number of arrhythmias. Long-term ω3-PUFA-intake modulates the activity of several cardiac ion channels leading to cardiac action potential shortening. Circulating ω3-PUFAs in the bloodstream and incorporated ω3-PUFAs in the cardiac membrane have a different mechanism to shorten the action potential. It is, however, unknown whether circulating ω3-PUFAs in the bloodstream enhance or diminish the effects of incorporated ω3-PUFAs. In the present study, we address this issue. Rabbits were fed a diet rich in fish oil (ω3) or sunflower oil (ω9, as control) for 3 weeks. Ventricular myocytes were isolated by enzymatic dissociation and action potentials were measured using the perforated patch-clamp technique in the absence and presence of acutely administered ω3-PUFAs. Plasma of ω3 fed rabbits contained more free eicosapentaenoic acid (EPA) and isolated myocytes of ω3 fed rabbits contained higher amounts of both EPA and docosahexaenoic acid (DHA) in their sarcolemma compared to control. In the absence of acutely administered fatty acids, ω3 myocytes had a shorter action potential with a more negative plateau than ω9 myocytes. In the ω9 myocytes, but not in the ω3 myocytes, acute administration of a mixture of EPA + DHA shortened the action potential significantly. From these data we conclude that incorporated ω3-PUFAs into the sarcolemma and acutely administered ω3 fatty acids do not have a cumulative effect on action potential duration and morphology. As a consequence, patients with a high cardiac ω3-PUFA status will probably not benefit from short term ω3 supplementation as an antiarrhythmic therapy. PMID:21423389

  3. Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

    NASA Astrophysics Data System (ADS)

    Tumanova, Natalia; Payen, Ricky; Springuel, Géraldine; Norberg, Bernadette; Robeyns, Koen; Le Duff, Cécile; Wouters, Johan; Leyssens, Tom

    2017-01-01

    This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

  4. 6-methyl-8-hexadecenoic acid: A novel fatty acid from the marine spongeDesmapsama anchorata.

    PubMed

    Carballeira, N M; Maldonado, M E

    1988-07-01

    The novel fatty acid 7-methyl-8-hexadecenoic (1) was identified in the marine spongeDesmapsama anchorata. Other interesting fatty acids identified were 14-methyl-8-hexadecenoic (2), better known through its methyl ester as one of the components of the sex attractant of the female dermestid beetle, and the saturated fatty acid 3-methylheptadecanoic (3), known to possess larvicidal activity. The main phospholipid fatty acids encountered inD. anchorata were palmitic (16∶0), behenic (22∶0) and 5,9-hexacosadienoic acid (26∶2), which together accounted for 50% of the total phospholipid fatty acid mixture.

  5. RNAi knockdown of fatty acid elongase1 alters fatty acid composition in Brassica napus.

    PubMed

    Shi, Jianghua; Lang, Chunxiu; Wu, Xuelong; Liu, Renhu; Zheng, Tao; Zhang, Dongqing; Chen, Jinqing; Wu, Guanting

    2015-10-23

    The quality and end-use of oil from oilseed crops is determined by its fatty acid composition. In particular, the relative proportions of erucic and oleic acids are key selection traits for breeders. The goal of our research is to genetically improve the nutritional quality of Brassica napus cultivar CY2, the oil of which is high in erucic acid (about 40%) and low in oleic acid (about 20%). Here, we report the use of a seed-specific napin A promoter to drive the knockdown of BnFAE1 in transgenic CY2. Southern blotting results confirmed the presence of the transgene. RT-PCR analysis showed that the levels of BnFAE1 were greatly decreased in BnFAE1-Ri lines compared with the CY2 cultivar. Knockdown of BnFAE1 sharply decreased the levels of erucic acid (less than 3%), largely increased the contents of oleic acid (more than 60%) and slightly increased the polyunsaturated chain fatty acids. Compared with high erucic acid parents, expression of BnFAE1 was dramatically decreased in developing F1 seeds derived from reciprocally crossed BnFAE1-Ri lines and high erucic acid cultivars. In addition, F1 seeds derived from reciprocal crosses between BnFAE1-Ri lines and high erucic acid cultivars showed significantly increased oleic acid (more than 52%) and sharply decreased erucic acid (less than 4%), demonstrating that the RNAi construct of BnFAE1 can effectively interfere with the target gene in F1 seeds. Taken together, our results demonstrate that BnFAE1 is a reliable target for genetic improvement of rapeseed in seed oil quality promotion. Copyright © 2015 Elsevier Inc. All rights reserved.

  6. Associations of erythrocyte fatty acid patterns with insulin resistance

    USDA-ARS?s Scientific Manuscript database

    Background: Synergistic and/or additive effects on cardiometabolic risk may be missed by examining individual fatty acids (FA). A pattern analysis may be a more useful approach. As well, it remains unclear whether erythrocyte fatty acid composition relates to insulin resistance among Hispanic/Latino...

  7. 21 CFR 573.914 - Salts of volatile fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity. The food additive is a... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Salts of volatile fatty acids. 573.914 Section 573...

  8. 21 CFR 573.914 - Salts of volatile fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ...) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity. The food additive is a... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Salts of volatile fatty acids. 573.914 Section 573...

  9. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... accordance with the following prescribed conditions: (a) They are prepared from corn oil, cottonseed oil, lard, palm oil from fruit, peanut oil, safflower oil, sesame oil, soybean oil, and tallow and the fatty....860(b) and/or oleic acid derived from tall oil fatty acids meeting the requirements of § 172.862....

  10. Fatty acid biosynthesis revisited: Structure elucidation and metabolic engineering

    DOE PAGES

    Beld, Joris; Lee, D. John; Burkart, Michael D.

    2014-10-20

    Fatty acids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fatty acid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fatty acid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fatty acid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fatty acids or specific high value products. Such efforts require a fundamental understandingmore » of the enzymatic activities and regulation of fatty acid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fatty acid synthases' many intricate structural and regulatory elements. Lastly, in this review, we summarize each enzymatic domain and discuss efforts to engineer fatty acid synthases, providing some clues to important challenges and opportunities in the field.« less

  11. Fatty acid composition of seed oil from Fremontodendron californicum

    USDA-ARS?s Scientific Manuscript database

    The fatty acid composition of the low water-use shrub Fremontodendron californicum was examined by high temperature capillary gas chromatography. The ground seeds were extracted by supercritical fluid extraction (SFE) to obtain the oil (25.6% w/w) and for subsequent determination of the fatty acid c...

  12. An overview of the properties of fatty acid alkyl esters

    USDA-ARS?s Scientific Manuscript database

    Fatty acid alkyl esters of plant oils, especially in the form of methyl esters, have numerous applications with fuel use having received the most attention in recent times due to the potential high volume. Various properties imparted by neat fatty acid alkyl esters have been shown to influence fuel ...

  13. 40 CFR 721.3629 - Triethanolamine salts of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Triethanolamine salts of fatty acids... Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified generically as triethanolamine salts of...

  14. 40 CFR 721.3629 - Triethanolamine salts of fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Triethanolamine salts of fatty acids... Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified generically as triethanolamine salts of...

  15. 40 CFR 721.3629 - Triethanolamine salts of fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Triethanolamine salts of fatty acids... Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified generically as triethanolamine salts of...

  16. 40 CFR 721.3629 - Triethanolamine salts of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Triethanolamine salts of fatty acids... Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified generically as triethanolamine salts of...

  17. 40 CFR 721.3629 - Triethanolamine salts of fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Triethanolamine salts of fatty acids... Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substances identified generically as triethanolamine salts of...

  18. DETERGENCY OF THE 12 TO 18 CARBON SATURATED FATTY ACIDS

    DTIC Science & Technology

    saturated fatty acids ) were explored to determine the relationship of the detergencies of such systems to the physico-chemical nature (HLB, hydrophile...suggested that in such systems the chief action is van der Waals adsorption between hydr oxide mole ratio adducts of tridecyl alcohol are poor detergents of the saturated fatty acids .

  19. Distillation of natural fatty acids and their chemical derivatives

    USDA-ARS?s Scientific Manuscript database

    Well over 1,000 different fatty acids are known which are natural components of fats, oils (triacylglycerols), and other related compounds. These fatty acids can have different alkyl chain lengths, 0-6 carbon-carbon double bonds possessing cis- or trans-geometry, and can contain a variety of functio...

  20. Fatty acid amides from freshwater green alga Rhizoclonium hieroglyphicum.

    PubMed

    Dembitsky, V M; Shkrob, I; Rozentsvet, O A

    2000-08-01

    Freshwater green algae Rhizoclonium hieroglyphicum growing in the Ural Mountains were examined for their fatty acid amides using capillary gas chromatography-mass spectrometry (GC-MS). Eight fatty acid amides were identified by GC-MS. (Z)-9-octadecenamide was found to be the major component (2.26%).

  1. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Lactylic esters of fatty acids. 172.848 Section 172.848 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... HUMAN CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters...

  2. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Lactylic esters of fatty acids. 172.848 Section 172.848 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... HUMAN CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters...

  3. Fatty acid profile of 25 alternative lipid feedstocks

    USDA-ARS?s Scientific Manuscript database

    This study reports the fatty acid profiles of 25 alternative lipid feedstocks for the production of bio-based fuels and chemicals. Lipids were extracted using hexane from oil-bearing seeds using a standard Soxhlet apparatus. Fatty acid profiles were measured using gas chromatography-flame ionization...

  4. Fatty acid composition of Tilia spp. seed oils

    USDA-ARS?s Scientific Manuscript database

    As part of a study of the seed oil fatty acid composition of Malvaceae plants, seeds of seven Tilia species (limes or linden trees) were evaluated for their fatty acid profiles. Seeds were obtained from the Germplasm Research Information Network and from various commercial sources. After extractio...

  5. Obesogenic diets enriched in oleic acid vs saturated fatty acids differentially modify polyunsaturated fatty acid composition in liver and visceral adipose

    USDA-ARS?s Scientific Manuscript database

    Emerging evidence indicates that the fatty acid composition of obesogenic diets impacts physiologic outcomes. Much attention is focused on the biologic effects of consuming monounsaturated fatty acids (MUFA) vs saturated fatty acids (SFA). We investigated the extent to which an obesogenic diet high ...

  6. Oviposition response ofLobesia botrana females to long-chain free fatty acids and esters from its eggs.

    PubMed

    Gabel, B; Thiéry, D

    1996-01-01

    Avoidance of occupied ovisposition sites supposes that females perceive information related to their own progency. Fatty acids identified from egg extracts have been reevaluated using a different extraction method, and we have investigated the dose-dependent oviposition response of European grape vine moths (Lobesia botrana) to myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, methyl palmitate, methyl oleate, and ethyl palmitate; all except ethyl palmitate have been identified from eggs ofL. botrana. A methylene dichloride extract of eggs fromL. botrana revealed the presence of saturated free fatty acids (myristic, palmitic, and stearic) and unsaturated acids (palmitoleic, oleic, linoleic, and linolenic) in amounts ranging from 3.9 ng/egg equivalent for myristic acid to 30 ng/egg equivalent for palmitic and oleic acids. The extract also contained traces of methyl palmitate and methyl stearate. The greatest avoidance indexes were observed in response to palmitic, palmitoleic, and oleic acids. All the other compounds tested caused weaker responses. A reduction in the number of eggs laid was observed when moths were exposed to each of the esters applied at 0.3 µg per application spot. Reduction in eggs laid was also observed at a 10-fold higher dose of oleic acid. The present results confirm that general and simple molecules can be involved in the regulation of oviposition site selection and that they may participate in chemical marking of the eggs.

  7. Determination of free fatty acids in beer.

    PubMed

    Bravi, Elisabetta; Marconi, Ombretta; Sileoni, Valeria; Perretti, Giuseppe

    2017-01-15

    Free fatty acids (FFA) content of beer affects the ability to form a stable head of foam and plays an important role in beer staling. Moreover, the presence of saturated FAs is related sometimes to gushing problems in beer. The aim of this research was to validate an analytical method for the determination of FFAs in beer. The extraction of FFAs in beer was achieved via Liquid-Liquid Cartridge Extraction (LLCE), the FFAs extract was purified by Solid Phase Extraction (SPE), methylated by boron trifluoride in methanol, and injected into GC-FID system. The performance criteria demonstrate that this method is suitable for the analysis of medium and long chain FFAs in beer. The proposed method was tested on four experimental beers. Copyright © 2016 Elsevier Ltd. All rights reserved.

  8. Factors affecting human colostrum fatty acid profile: A case study

    PubMed Central

    Cavouras, Dionisis; Boutsikou, Theodora; Briana, Despina D.; Lantzouraki, Dimitra Z.; Paliatsiou, Stella; Volaki, Paraskevi; Bratakos, Sotiris; Malamitsi-Puchner, Ariadne; Zoumpoulakis, Panagiotis

    2017-01-01

    The role of maternal colostrum to infant development has been extensively studied and presented. Among the main factors which contribute to breast milk composition are maternal diet, age and body mass index, parity, duration of pregnancy and stage of lactation. This study aims to investigate the potential impact of several factors including demographic (i.e. maternal age and nationality) on the colostrum fatty acid profile. Colostrum was collected the third day postpartum in a Greek maternity hospital. Certain lipid quality indices and fatty acid ratios were estimated and results were statistically processed. The main identified fatty acids were palmitic (C16:0), oleic (C18:1ω-9), and linoleic (C18:2ω-6) acids. Among fatty acids, saturated fatty acids predominated (47.61%), followed by monounsaturated fatty acids (39.26%), while polyunsaturated fatty acids had the lowest proportion (13.13%). Values of lipid quality indices were within the reported in the literature ranges. Maternal body mass index, nationality, age, mode of delivery, gender and fetal weight percentile were studied in respect to their potential influence on the fatty acid profile of colostrum fat. Results suggest that colostrum fatty acid profile was mainly dependent on maternal nationality and age rather than mode of delivery and maternal BMI. Regarding the effect of maternal nationality, significant differences were found for saturated and monounsaturated fatty acids. Of the most interesting findings is that colostrum fat from older (≥35 years) mothers had less saturated fat and more appropriate LQIs values. Finally, a reversed correlation was observed between the customized centile of the infants and the colostrum fat content. PMID:28410426

  9. Fatty acids profiles of some Spanish wild vegetables.

    PubMed

    Morales, P; Ferreira, I C F R; Carvalho, A M; Sánchez-Mata, M C; Cámara, M; Tardío, J

    2012-06-01

    Polyunsaturated fatty acids play an important role in human nutrition, being associated with several health benefits. The analyzed vegetables, in spite of its low fat content, lower than 2%, present a high proportion of polyunsaturated fatty acids of n-3, n-6 and n-9 series, such as α-linolenic, linoleic and oleic acids, respectively. Wild edible plants contain in general a good balance of n-6 and n-3 fatty acids. The present study tries to contribute to the preservation and valorization of traditional food resources, studying the fatty acids profile of 20 wild vegetables by gas-liquid chromatography with flame ionization detection. Results show that species in which leaves are predominant in their edible parts have in general the highest polyunsaturated fatty acid/saturated fatty acid ratios: Rumex pulcher (5.44), Cichorium intybus (5.14) and Papaver rhoeas (5.00). Due to the low n-6/n-3 ratios of the majority of the samples, they can be considered interesting sources of n-3 fatty acids, especially those with higher total fat amount, such as Bryonia dioica, Chondrilla juncea or Montia fontana, with the highest contents of α-linolenic acid (67.78, 56.27 and 47.65%, respectively). The wild asparaguses of Asparagus acutifolius and Tamus communis stand out for their linoleic acid content (42.29 and 42.45%, respectively). All these features reinforce the interest of including wild plants in diet, as an alternative to the variety of vegetables normally used.

  10. Production of extracellular fatty acid using engineered Escherichia coli.

    PubMed

    Liu, Hui; Yu, Chao; Feng, Dexin; Cheng, Tao; Meng, Xin; Liu, Wei; Zou, Huibin; Xian, Mo

    2012-04-03

    As an alternative for economic biodiesel production, the microbial production of extracellular fatty acid from renewable resources is receiving more concerns recently, since the separation of fatty acid from microorganism cells is normally involved in a series of energy-intensive steps. Many attempts have been made to construct fatty acid producing strains by targeting genes in the fatty acid biosynthetic pathway, while few studies focused on the cultivation process and the mass transfer kinetics. In this study, both strain improvements and cultivation process strategies were applied to increase extracellular fatty acid production by engineered Escherichia coli. Our results showed overexpressing 'TesA and the deletion of fadL in E. coli BL21 (DE3) improved extracellular fatty acid production, while deletion of fadD didn't strengthen the extracellular fatty acid production for an undetermined mechanism. Moreover, the cultivation process controls contributed greatly to extracellular fatty acid production with respect to titer, cell growth and productivity by adjusting the temperature, adding ampicillin and employing on-line extraction. Under optimal conditions, the E. coli strain (pACY-'tesA-ΔfadL) produced 4.8 g L⁻¹ extracellular fatty acid, with the specific productivity of 0.02 g h⁻¹ g⁻¹ dry cell mass, and the yield of 4.4% on glucose, while the ratios of cell-associated fatty acid versus extracellular fatty acid were kept below 0.5 after 15 h of cultivation. The fatty acids included C12:1, C12:0, C14:1, C14:0, C16:1, C16:0, C18:1, C18:0. The composition was dominated by C14 and C16 saturated and unsaturated fatty acids. Using the strain pACY-'tesA, similar results appeared under the same culture conditions and the titer was also much higher than that ever reported previously, which suggested that the supposedly superior strain did not necessarily perform best for the efficient production of desired product. The strain pACY-'tesA could also be chosen as

  11. Influence of changes in dietary fatty acids during pregnancy on placental and fetal fatty acid profile in the rat.

    PubMed

    Amusquivar, Encarnación; Herrera, Emilio

    2003-01-01

    To determine whether the composition of long-chain polyunsaturated fatty acids (PUFA) could be modified in the fetus by maternal dietary fatty acids, pregnant Sprague-Dawley rats were fed semipurified diets that differed only in the non-vitamin lipid component. The diets contained either 10 g palm, sunflower, olive or fish oil (FOD)/100 g diet. A total of 5-6 rats were studied in each group. At day 20 of gestation, corresponding to 1.5 days prior parturition, the fatty acids in maternal adipose tissue were closely related to the fatty acid composition in the corresponding diet. An important proportion of arachidonic acid (AA) appeared in maternal liver and plasma, although it was lower in the FOD than in the other groups. Except for saturated fatty acids, the proportion of individual fatty acids in the placenta correlated linearly with that in maternal plasma. Also, PUFA in fetal plasma and liver showed significant correlations with PUFA in maternal plasma. Again, AA showed the lowest proportion in the plasma and liver of the FOD group. Therefore, the maternal dietary fatty acid composition influences maternal and fetal plasma and tissue composition, and an increase in dietary omega-3 fatty acids decreases the amount of AA in maternal and fetal tissues.

  12. Increased Production of Fatty Acids and Triglycerides in Aspergillus oryzae by Enhancing Expressions of Fatty Acid Synthesis-Related Genes

    SciTech Connect

    Tamano, Koichi; Bruno, Kenneth S.; Karagiosis, Sue A.; Culley, David E.; Deng, Shuang; Collett, James R.; Umemura, Myco; Koike, Hideaki; Baker, Scott E.; Machida, Masa

    2013-01-01

    Microbial production of fats and oils is being developedas a means of converting biomass to biofuels. Here we investigate enhancing expression of enzymes involved in the production of fatty acids and triglycerides as a means to increase production of these compounds in Aspergillusoryzae. Examination of the A.oryzaegenome demonstrates that it contains twofatty acid synthases and several other genes that are predicted to be part of this biosynthetic pathway. We enhancedthe expressionof fatty acid synthesis-related genes by replacing their promoters with thepromoter fromthe constitutively highly expressedgene tef1. We demonstrate that by simply increasing the expression of the fatty acid synthasegenes we successfullyincreasedtheproduction of fatty acids and triglyceridesby more than two fold. Enhancement of expression of the fatty acid pathway genes ATP-citrate lyase and palmitoyl-ACP thioesteraseincreasedproductivity to a lesser extent.Increasing expression ofacetyl-CoA carboxylase caused no detectable change in fatty acid levels. Increases in message level for each gene were monitored usingquantitative real-time RT-PCR. Our data demonstrates that a simple increase in the abundance of fatty acid synthase genes can increase the detectable amount of fatty acids.

  13. Fatty acid composition of selected macrophytes.

    PubMed

    Patarra, R F; Leite, J; Pereira, R; Baptista, J; Neto, A I

    2013-04-01

    The content of total lipids and the fatty acid (FA) profile were determined for eight macroalgae (Cystoseira abies-marina, Fucus spiralis, Chaetomorpha pachynema, Codium elisabethae, Porphyra sp., Osmundea pinnatifida, Pterocladiella capillacea and Sphaeroccoccus coronopifolius). Total lipids were extracted using a solvent mixture of methanol/chloroform (2/1, v/v) and further derivatised to FA methyl esters (FAME). The analyses of FAME samples were performed by gas chromatography coupled to a flame ionisation detector. The total lipid content ranged from 0.06 to 3.54 g (per 100 g). The most abundant saturated FA were palmitic (C16:0) and myristic (C14:0), while oleic (C18:1 n-9) was the dominant monounsaturated acid. All seaweeds contained linoleic FA (C18:2 n-6). The α-linolenic (C18:3 n-3) and eicosapentaenoic (20:5 n-3) acids were present only in Porphyra sp. (3.34% ± 0.13) and C. pachynema (0.47% ± 0.12), respectively. The n-6/n-3 and h/H ratios were low, suggesting a high nutritional value of the algae studied.

  14. Fatty acids as modulators of neutrophil recruitment, function and survival.

    PubMed

    Rodrigues, Hosana G; Takeo Sato, Fabio; Curi, Rui; Vinolo, Marco A R

    2016-08-15

    Neutrophils are well-known to act in the destruction of invading microorganisms. They have also been implicated in the activation of other immune cells including B- and T-lymphocytes and in the resolution of inflammation and tissue regeneration. Neutrophils are produced in the bone marrow and released into the circulation from where they migrate to tissues to perform their effector functions. Neutrophils are in constant contact with fatty acids that can modulate their function, activation and fate (survival or cell death) through different mechanisms. In this review, the effects of fatty acids pertaining to five classes, namely, long-chain saturated fatty acids (LCSFAs), short-chain fatty acids (SCFAs), and omega-3 (n-3), omega-6 (n-6) and omega-9 (n-9) unsaturated fatty acids, on neutrophils and the relevance of these effects for disease development are discussed. Copyright © 2015 Elsevier B.V. All rights reserved.

  15. Trans-fatty acids and cardiovascular risk: does origin matter?

    PubMed

    Dawczynski, Christine; Lorkowski, Stefan

    2016-09-01

    Several studies have aimed to unravel the contribution of different types of dietary fatty acids to human health and disease. Investigations have consistently shown that high consumption of industrially produced trans-fatty acids from partially hydrogenated vegetable oils is harmful to human health, in particular cardiovascular health. Therefore, the U.S. Food and Drug Administration announced that partially hydrogenated oils are no longer 'generally recognized as safe', and trans-fatty acids are not permitted in the U.S. food supply. On the other hand, recent studies analyzing the association between circulating trans-fatty acids and disease have revealed that some ruminant-specific trans-fatty acids are associated with a reduction in incidence of disease. In this special report, we highlight recent findings and point out perspectives for future studies on this topic.

  16. Fatty acids and the Endoplasmic Reticulum in Non-Alcoholic Fatty Liver Disease

    PubMed Central

    Gentile, Christopher L.; Frye, Melinda A.; Pagliassotti, Michael J.

    2011-01-01

    Non-alcoholic fatty liver disease (NAFLD) represents a burgeoning public health concernin westernized nations. The obesity-related disorder is associated with an increased risk of cardiovascular disease, type 2 diabetes and liver failure. Although the underlying pathogenesis of NAFLD is unclear, increasing evidence suggests that excess saturated fatty acids presented to or stored within the liver may play a role in both the development and progression of the disorder. Aputative mechanism linking saturated fatty acids to NAFLD may been doplasmic reticulum (ER) stress. Specifically, excess saturated fatty acids may induce an ER stress response that, if left unabated, can activate stress signaling pathways, cause hepatocyte cell death, and eventually lead to liver dysfunction. In the current review we discuss the involvement of saturated fatty acids in the pathogenesis of NAFLD with particular emphasis on the role of ER stress. PMID:21328622

  17. Cloning and functional expression of the first plant fatty acid elongase specific for Delta(6)-polyunsaturated fatty acids.

    PubMed

    Zank, T K; Zähringer, U; Lerchl, J; Heinz, E

    2000-12-01

    In order to elucidate the biosynthesis of long-chain polyunsaturated fatty acids (PUFAs) in plants we searched for a cDNA encoding a Delta(6)-specific PUFA elongase from Physcomitrella patens, which is known to contain high proportions of arachidonic acid (20:4 Delta(5,8,11,14)). An EST clone from P. patens was identified by its low homology to the yeast gene ELO1, which is required for the elongation of medium-chain fatty acids. We functionally characterized this cDNA by heterologous expression in Saccharomyces cerevisiae grown in the presence of several fatty acids. Analysis of the fatty acid profile of the transgenic yeast revealed that the cDNA encodes a protein that leads to the elongation of the C(18) Delta(6)-polyunsaturated fatty acids gamma-linolenic acid (18:3 Delta(6,9,12)) and stearidonic acid (18:4 Delta(6,9,12,15)), which were recovered to 45-51% as their elongation products. In contrast, linoleic and alpha-linolenic acids were hardly elongated and we could not measure any elongation of saturated and mono-unsaturated fatty acids (including 18:1 Delta(6)), indicating that the elongase is highly specific for the polyunsaturated nature of the fatty acid acting as substrate.

  18. Overproduction of a Functional Fatty Acid Biosynthetic Enzyme Blocks Fatty Acid Synthesis in Escherichia coli

    PubMed Central

    Subrahmanyam, Satyanarayana; Cronan, John E.

    1998-01-01

    β-Ketoacyl-acyl carrier protein (ACP) synthetase II (KAS II) is one of three Escherichia coli isozymes that catalyze the elongation of growing fatty acid chains by condensation of acyl-ACP with malonyl-ACP. Overexpression of this enzyme has been found to be extremely toxic to E. coli, much more so than overproduction of either of the other KAS isozymes, KAS I or KAS III. The immediate effect of KAS II overproduction is the cessation of phospholipid synthesis, and this inhibition is specifically due to the blockage of fatty acid synthesis. To determine the cause of this inhibition, we examined the intracellular pools of ACP, coenzyme A (CoA), and their acyl thioesters. Although no significant changes were detected in the acyl-ACP pools, the CoA pools were dramatically altered by KAS II overproduction. Malonyl-CoA increased to about 40% of the total cellular CoA pool upon KAS II overproduction from a steady-state level of around 0.5% in the absence of KAS II overproduction. This finding indicated that the conversion of malonyl-CoA to fatty acids had been blocked and could be explained if either the conversion of malonyl-CoA to malonyl-ACP and/or the elongation reactions of fatty acid synthesis had been blocked. Overproduction of malonyl-CoA:ACP transacylase, the enzyme catalyzing the conversion of malonyl-CoA to malonyl-ACP, partially relieved the toxicity of KAS II overproduction, consistent with a model in which high levels of KAS II blocks access of the other KAS isozymes to malonyl-CoA:ACP transacylase. PMID:9721301

  19. Fatty Acids, Lipid Mediators, and T-Cell Function

    PubMed Central

    de Jong, Anja J.; Kloppenburg, Margreet; Toes, René E. M.; Ioan-Facsinay, Andreea

    2014-01-01

    Research toward the mechanisms underlying obesity-linked complications has intensified during the last years. As a consequence, it has become clear that metabolism and immunity are intimately linked. Free fatty acids and other lipids acquired in excess by current feeding patterns have been proposed to mediate this link due to their immune modulatory capacity. The functional differences between saturated and unsaturated fatty acids, in combination with their dietary intake are believed to modulate the outcome of immune responses. Moreover, unsaturated fatty acids can be oxidized in a tightly regulated and specific manner to generate either potent pro-inflammatory or pro-resolving lipid mediators. These oxidative derivatives of fatty acids have received detailed attention during the last years, as they have proven to have strong immune modulatory capacity, even in pM ranges. Both fatty acids and oxidized fatty acids have been studied especially in relation to macrophage and T-cells functions. In this review, we propose to focus on the effect of fatty acids and their oxidative derivatives on T-cells, as it is an active area of research during the past 5 years. The effect of fatty acids and their derivatives on activation and proliferation of T-cells, as well as the delicate balance between stimulation and lipotoxicity will be discussed. Moreover, the receptors involved in the interaction between free fatty acids and their derivatives with T-cells will be summarized. Finally, the mechanisms involved in modulation of T-cells by fatty acids will be addressed, including cellular signaling and metabolism of T-cells. The in vitro results will be placed in context of in vivo studies both in humans and mice. In this review, we summarize the latest findings on the immune modulatory function of lipids on T-cells and will point out novel directions for future research. PMID:25352844

  20. [Trans fatty acids (elaidic and vaccenic) in the human milk].

    PubMed

    Jamioł-Milc, Dominika; Stachowska, Ewa; Janus, Tomasz; Barcz, Anna; Chlubek, Dariusz

    2015-01-01

    The structure of trans unsaturated fatty acids (TFAs) includes at least one double bond with a trans configuration. Numerous studies have shown that TFAs influence negative changes in blood lipid profile, may initiate or accelerate the course of many inflammatory diseases, and reduce n-6 and n-3 fatty acids' utilization. Their presence in tissues and systemic fluids is mainly the result of ingestion of TFA-containing foods. The objective of this study was to determine the concentration profiles of elaidic and vaccenic acids in human milk, and the existence of potential correlations between the levels of trans-unsaturated fatty acids and long chain polyunsaturated fatty acids. The study group consisted of 53 lactating women, aged 18-39 years, 5-6 weeks after delivery. Elaidic and vaccenic acid levels were determined in human milk. Fatty acid methyl esters were injected onto the capillary column of an Agilent 6890M gas chromatography system integrated with an autosampler. Geometrical and positional isomers of fatty acids were identified by comparing their retention times with those of the fatty acid standards from Sigma-Aldrich. The content of individual fatty acids was determined from the reference curves and expressed in mg/mL. The level of elaidic acid was 0.2572 ± 0.1811 mg/mL, and the level of vaccenic acid was 0.2736 ± 0.1852 mg/mL. No negative correlations between the levels of the analyzed TFAs and PUFAs were observed in human milk. The levels of elaidic and vaccenic acid were similar and had no negative influence on the levels of arachidonic acid and docosahexaenoic acid.

  1. Parameters Affecting Ethyl Ester Production by Saccharomyces cerevisiae during Fermentation▿

    PubMed Central

    Saerens, S. M. G.; Delvaux, F.; Verstrepen, K. J.; Van Dijck, P.; Thevelein, J. M.; Delvaux, F. R.

    2008-01-01

    Volatile esters are responsible for the fruity character of fermented beverages and thus constitute a vital group of aromatic compounds in beer and wine. Many fermentation parameters are known to affect volatile ester production. In order to obtain insight into the production of ethyl esters during fermentation, we investigated the influence of several fermentation variables. A higher level of unsaturated fatty acids in the fermentation medium resulted in a general decrease in ethyl ester production. On the other hand, a higher fermentation temperature resulted in greater ethyl octanoate and decanoate production, while a higher carbon or nitrogen content of the fermentation medium resulted in only moderate changes in ethyl ester production. Analysis of the expression of the ethyl ester biosynthesis genes EEB1 and EHT1 after addition of medium-chain fatty acid precursors suggested that the expression level is not the limiting factor for ethyl ester production, as opposed to acetate ester production. Together with the previous demonstration that provision of medium-chain fatty acids, which are the substrates for ethyl ester formation, to the fermentation medium causes a strong increase in the formation of the corresponding ethyl esters, this result further supports the hypothesis that precursor availability has an important role in ethyl ester production. We concluded that, at least in our fermentation conditions and with our yeast strain, the fatty acid precursor level rather than the activity of the biosynthetic enzymes is the major limiting factor for ethyl ester production. The expression level and activity of the fatty acid biosynthetic enzymes therefore appear to be prime targets for flavor modification by alteration of process parameters or through strain selection. PMID:17993562

  2. Inhibition of in vitro cholesterol synthesis by fatty acids.

    PubMed

    Kuroda, M; Endo, A

    1976-01-18

    Inhibitory effect of 44 species of fatty acids on cholesterol synthesis has been examined with a rat liver enzyme system. In the case of saturated fatty acids, the inhibitory activity increased with chain length to a maximum at 11 to 14 carbons, after which activity decreased rapidly. The inhibition increased with the degree of unsaturation of fatty acids. Introduction of a hydroxy group at the alpha-position of fatty acids abolished the inhibition, while the inhibition was enhanced by the presence of a hydroxy group located in an intermediate position of the chain. Branched chain fatty acids having a methyl group at the terminal showed much higher activity than the corresponding saturated straight chain fatty acids with the same number of carbons. With respect to the mechanism for inhibition, tridecanoate was found to inhibit acetoacetyl-CoA thiolase specifically without affecting the other reaction steps in the cholesterol synthetic pathway. The highly unsaturated fatty acids, arachidonate and linoleate, were specific inhibitors of 3-hydroxy-3-methyl-glutaryl-CoA synthase. On the other hand, ricinoleate (hydroxy acid) and phytanate (branched-chain acid) diminished the conversion of mevalonate to sterols by inhibiting a step or steps between squalene and lanosterol.

  3. Prenatal omega-3 fatty acids: review and recommendations.

    PubMed

    Jordan, Robin G

    2010-01-01

    The influence of dietary omega-3 fatty acids on health outcomes is widely recognized. The adequate intake of omega-3 fatty acids docasahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) in particular can increase gestation length and improve infant cognitive and visual performance. Adequate levels of omega-3 fatty acids have also been shown to reduce the incidence of preterm birth in some populations. Research on prenatal omega-3 intake and other outcomes, such as preeclampsia and fetal growth restriction, is inconclusive. Women in the United States consume low levels of omega-3 fatty acids compared to omega-6 fatty acids; this dietary pattern is associated with poor health outcomes. Omega-3 fatty acids are found primarily in fish, yet many pregnant women avoid fish because of concerns about potential mercury and polychlorinated biphenyl contamination. It is important for prenatal care providers to assess women's diets for omega-3 fatty acid intake and ensure that pregnant women are consuming between 200 and 300 mg daily from safe food sources. Purified fish, algal oil supplements, and DHA-enriched eggs are alternative sources for pregnant women who do not eat fish.

  4. Fatty acids are precursors of alkylamines in Deinococcus radiodurans.

    PubMed Central

    Anderson, R; Huang, Y

    1992-01-01

    Deinococcus radiodurans contains novel phospholipids of which the structures of three have been previously described. These three lipids contain both fatty acids and alkylamines. Both the fatty acid and alkylamine constituents were found to be composed of a mixture of species, of which C15, C16, and C17 saturated and monounsaturated alkyl chains predominated. Alkylamines contained a relatively higher proportion of saturated species. Progression of bacterial growth through the mid-log to stationary phases was accompanied by an increase in the proportions of C15 and C17 alkyl chains in both fatty acid and alkylamine constituents. Radiolabeled palmitic acid was found to be rapidly incorporated into both fatty acid and alkylamine components of phosphatidylglyceroylalkylamine, which is the precursor of the more-complex phosphoglycolipids found in major amounts in D. radiodurans. After culturing D. radiodurans in the presence of a mixture of palmitic acids labeled with 14C and 3H in the 1 and 9,10 positions, respectively, the same 14C/3H ratio was recovered in both fatty acid and alkylamine constituents, strongly suggesting that alkylamines are derived from intact fatty acids rather than by a de novo pathway. The results identify a novel product of fatty acid metabolism which has not to date been observed in any other organism. Images PMID:1429439

  5. Understanding hypertriglyceridemia in women: clinical impact and management with prescription omega-3-acid ethyl esters.

    PubMed

    Dayspring, Thomas D

    2011-03-09

    Elevated triglycerides (TGs) are a common lipid disorder in the US and are associated with comorbidities such as pancreatitis, obesity, type 2 diabetes, and metabolic syndrome. TGs are generally elevated in postmenopausal women compared with premenopausal women. Meta-analysis has shown that elevated TGs are associated with an increased risk of coronary heart disease (CHD). This article provides a general overview of TG metabolism and reviews data on the epidemiology and risk of elevated TGs in women, as pregnancy and menopause, in particular, have been associated with unfavorable changes in the lipoprotein profile, including elevations in TGs. In addition, this review seeks to explain the recommended TG goals and treatment options for hypertriglyceridemia with an emphasis on severe hypertriglyceridemia (TGs ≥ 500 mg/dL) and its respective treatment with prescription omega-3-acid ethyl esters (P-OM3). MedLine was searched for articles published through August 2009 using the terms "hypertriglyceridemia" and "dyslipidemia", with subheadings for "prevalence", "women", "treatment", "guidelines", "risk", and "omega-3 fatty acids". Publications discussing the epidemiology of hypertriglyceridemia, CHD risk, treatment guidelines for lipid management, or clinical trials involving P-OM3 were selected for review. The reference lists of relevant articles were also examined for additional citations. Hypertriglyceridemia is associated with increased CHD risk. Women, especially those with polycystic ovarian syndrome, type 2 diabetes, or who are postmenopausal, should be monitored regularly for the impact of hypertriglyceridemia on their lipid profile. Cardiovascular risk of TGs can be indirectly assessed by monitoring non-high-density lipoprotein cholesterol (non-HDL-C) levels. There are multiple sets of guidelines providing recommendations for desirable low-density lipoprotein cholesterol, TG, and non-HDL-C levels. Treatment of hypertriglyceridemia includes lifestyle

  6. Recent trends in the advanced analysis of bioactive fatty acids.

    PubMed

    Ruiz-Rodriguez, Alejandro; Reglero, Guillermo; Ibañez, Elena

    2010-01-20

    The consumption of dietary fats have been long associated to chronic diseases such as obesity, diabetes, cancer, arthritis, asthma, and cardiovascular disease; although some controversy still exists in the role of dietary fats in human health, certain fats have demonstrated their positive effect in the modulation of abnormal fatty acid and eicosanoid metabolism, both of them associated to chronic diseases. Among the different fats, some fatty acids can be used as functional ingredients such as alpha-linolenic acid (ALA), arachidonic acid (AA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), gamma-linolenic acid (GLA), stearidonic acid (STA) and conjugated linoleic acid (CLA), among others. The present review is focused on recent developments in FAs analysis, covering sample preparation methods such as extraction, fractionation and derivatization as well as new advances in chromatographic methods such as GC and HPLC. Special attention is paid to trans fatty acids due its increasing interest for the food industry.

  7. Dietary fatty acids modulate associations between genetic variants and circulating fatty acids in plasma and erythrocyte membranes: Meta-analysis of nine studies in the CHARGE consortium.

    PubMed

    Smith, Caren E; Follis, Jack L; Nettleton, Jennifer A; Foy, Millennia; Wu, Jason H Y; Ma, Yiyi; Tanaka, Toshiko; Manichakul, Ani W; Wu, Hongyu; Chu, Audrey Y; Steffen, Lyn M; Fornage, Myriam; Mozaffarian, Dariush; Kabagambe, Edmond K; Ferruci, Luigi; Chen, Yii-Der Ida; Rich, Stephen S; Djoussé, Luc; Ridker, Paul M; Tang, Weihong; McKnight, Barbara; Tsai, Michael Y; Bandinelli, Stefania; Rotter, Jerome I; Hu, Frank B; Chasman, Daniel I; Psaty, Bruce M; Arnett, Donna K; King, Irena B; Sun, Qi; Wang, Lu; Lumley, Thomas; Chiuve, Stephanie E; Siscovick, David S; Ordovás, José M; Lemaitre, Rozenn N

    2015-07-01

    Tissue concentrations of omega-3 fatty acids may reduce cardiovascular disease risk, and genetic variants are associated with circulating fatty acids concentrations. Whether dietary fatty acids interact with genetic variants to modify circulating omega-3 fatty acids is unclear. We evaluated interactions between genetic variants and fatty acid intakes for circulating alpha-linoleic acid, eicosapentaenoic acid, docosahexaenoic acid, and docosapentaenoic acid. We conducted meta-analyses (N = 11 668) evaluating interactions between dietary fatty acids and genetic variants (rs174538 and rs174548 in FADS1 (fatty acid desaturase 1), rs7435 in AGPAT3 (1-acyl-sn-glycerol-3-phosphate), rs4985167 in PDXDC1 (pyridoxal-dependent decarboxylase domain-containing 1), rs780094 in GCKR (glucokinase regulatory protein), and rs3734398 in ELOVL2 (fatty acid elongase 2)). Stratification by measurement compartment (plasma versus erthyrocyte) revealed compartment-specific interactions between FADS1 rs174538 and rs174548 and dietary alpha-linolenic acid and linoleic acid for docosahexaenoic acid and docosapentaenoic acid. Our findings reinforce earlier reports that genetically based differences in circulating fatty acids may be partially due to differences in the conversion of fatty acid precursors. Further, fatty acids measurement compartment may modify gene-diet relationships, and considering compartment may improve the detection of gene-fatty acids interactions for circulating fatty acid outcomes. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Erythrocyte stearidonic acid and other n-3 fatty acids and CHD in the Physicians’ Health Study

    USDA-ARS?s Scientific Manuscript database

    Intake of marine-based n-3 fatty acids (EPA, docosapentaenoic acid and DHA) is recommended to prevent CHD. Stearidonic acid (SDA), a plant-based n-3 fatty acid, is a precursor of EPA and may be more readily converted to EPA than a-linolenic acid (ALA). While transgenic soyabeans might supply SDA at ...

  9. Fatty acid profile of Albizia lebbeck and Albizia saman seed oils: Presence of coronaric acid

    USDA-ARS?s Scientific Manuscript database

    In this work, the fatty acid profiles of the seed oils of Albizia lebbeck and Albizia saman (Samanea saman) are reported. The oils were analyzed by GC, GC-MS, and NMR. The most prominent fatty acid in both oils is linoleic acid (30-40%), followed by palmitic acid and oleic acid for A. lebbeck and ol...

  10. Regulation of hepatic gene expression by saturated fatty acids

    PubMed Central

    Vallim, T.; Salter, A.M.

    2010-01-01

    Diets rich in saturated fatty acids have long been associated with increased plasma cholesterol concentrations and hence increased risk of cardiovascular disease. More recently, they have also been suggested to promote the development of non-alcoholic fatty liver disease. While there is now considerable evidence to suggest that polyunsaturated fatty acids exert many of their effects through regulating the activity of transcription factors, including peroxisome proliferator activated receptors, sterol regulatory binding proteins (SREBPs) and liver X receptor, our understanding of how saturated fatty acids act is still limited. Here we review the potential mechanisms whereby saturated fatty acids modulate hepatic lipid metabolism thereby impacting on the synthesis, storage and secretion of lipids. Evidence is presented that their effects are, at least partly, mediated through modulation of the activity of the SREBP family of transcription factors. PMID:20227267

  11. Regulation of hepatic gene expression by saturated fatty acids.

    PubMed

    Vallim, T; Salter, A M

    2010-01-01

    Diets rich in saturated fatty acids have long been associated with increased plasma cholesterol concentrations and hence increased risk of cardiovascular disease. More recently, they have also been suggested to promote the development of non-alcoholic fatty liver disease. While there is now considerable evidence to suggest that polyunsaturated fatty acids exert many of their effects through regulating the activity of transcription factors, including peroxisome proliferator activated receptors, sterol regulatory binding proteins (SREBPs) and liver X receptor, our understanding of how saturated fatty acids act is still limited. Here we review the potential mechanisms whereby saturated fatty acids modulate hepatic lipid metabolism thereby impacting on the synthesis, storage and secretion of lipids. Evidence is presented that their effects are, at least partly, mediated through modulation of the activity of the SREBP family of transcription factors.

  12. Inhibition of polyunsaturated fatty acid accumulation in plants expressing a fatty acid epoxygenase.

    PubMed

    Singh, S; Thomaeus, S; Lee, M; Green, A; Stymne, S

    2000-12-01

    Earlier, we described the isolation of a Crepis palaestina cDNA (Cpal2) which encoded a Delta12-epoxygenase that could catalyse the synthesis of 12,13-epoxy-cis-9-octadecenoic acid (18:1E) from linoleic acid (18:2). When the Cpal2 gene was expressed under the control of a seed-specific promoter in Arabidopsis, plants were able to accumulate small amounts 18:1E and 12,13-epoxy-cis-9,15-octadec-2-enoic acid in their seed lipids. In this report we give results obtained from a detailed analysis of transgenic Arabidopsis plants containing the Cpal2 gene. The seeds from these plants accumulate varying levels of 18:1E, but show a marked increase in 18:1 and equivalent decrease in 18:2 and 18:3. We further observed that the co-expression of a C. palaestina Delta12-desaturase in Arabidopsis appears to return the relative proportions of the C(18) seed fatty acids to normal levels and results in a 2-fold increase in total epoxy fatty acids.

  13. Dynamic regulation of fatty acid pools for improved production of fatty alcohols in Saccharomyces cerevisiae.

    PubMed

    Teixeira, Paulo Gonçalves; Ferreira, Raphael; Zhou, Yongjin J; Siewers, Verena; Nielsen, Jens

    2017-03-15

    In vivo production of fatty acid-derived chemicals in Saccharomyces cerevisiae requires strategies to increase the intracellular supply of either acyl-CoA or free fatty acids (FFAs), since their cytosolic concentrations are quite low in a natural state for this organism. Deletion of the fatty acyl-CoA synthetase genes FAA1 and FAA4 is an effective and straightforward way to disable re-activation of fatty acids and drastically increase FFA levels. However, this strategy causes FFA over-accumulation and consequential release to the extracellular medium, which results in a significant loss of precursors that compromises the process yield. In the present study, we aimed for dynamic expression of the fatty acyl-CoA synthetase gene FAA1 to regulate FFA and acyl-CoA pools in order to improve fatty alcohol production yields. We analyzed the metabolite dynamics of a faa1Δ faa4Δ strain constitutively expressing a carboxylic acid reductase from Mycobacterium marinum (MmCAR) and an endogenous alcohol dehydrogenase (Adh5) for in vivo production of fatty alcohols from FFAs. We observed production of fatty acids and fatty alcohols with different rates leading to high levels of FFAs not being converted to the final product. To address the issue, we expressed the MmCAR + Adh5 pathway together with a fatty acyl-CoA reductase from Marinobacter aquaeolei to enable fatty alcohol production simultaneously from FFA and acyl-CoA, respectively. Then, we expressed FAA1 under the control of different promoters in order to balance FFA and acyl-CoA interconversion rates and to achieve optimal levels for conversion to fatty alcohols. Expressing FAA1 under control of the HXT1 promoter led to an increased accumulation of fatty alcohols per OD600 up to 41% while FFA levels were decreased by 63% compared with the control strain. Fine-tuning and dynamic regulation of key metabolic steps can be used to improve cell factories when the rates of downstream reactions are limiting. This avoids loss of

  14. CONTENT OF AMINO ACIDS, FATTY ACIDS AND SOME GLYCIDES IN THE FUNGUS STACHYBOTRYS ALTERNANS

    DTIC Science & Technology

    The amino acid, fatty acid, and glycide content of the mycelium of Stachybotrys alternans was determined, and, for purposes of comparison, of some...unsaturated fatty acids. In the case of Stachybotrys alternans the individual strains exhibited small differences in the composition with respect to these...substances. Differences in the occurrence of amino acids and fatty acids were found in some strains of Stachybotrys alternans even after long-lasting

  15. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2... 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2'-(1,2-diazenediyl)bis - and 2,2'-(1,2...

  16. Separation and quantitation of free fatty acids and fatty acid methyl esters by reverse phase high pressure liquid chromatography.

    PubMed

    Aveldano, M I; VanRollins, M; Horrocks, L A

    1983-01-01

    Reverse phase high pressure liquid chromatography (HPLC) on octadecylsilyl columns separates mixtures of either free fatty acids or fatty acid methyl esters prepared from mammalian tissue phospholipids. Acetonitrile-water mixtures are used for the elution of esters. Aqueous phosphoric acid is substituted for water for the separation of the free acids. Unsaturated compounds are detected and quantitated by their absorption at 192 nm. Saturates are detected better at 205 nm. The order of elution of fatty acids in complex mixtures varies as a function of acetonitrile concentration. At any given concentration, some compounds overlap. However, by varying the solvent strength, any fatty acid of interest can be resolved including many geometrical and positional isomers. Methyl esters prefractionated according to unsaturation by argentation thin-layer chromatography (TLC) are rapidly and completely separated by elution with CH3CN alone. Argentation TLC-reverse phase HPLC can be used as an analytical as well as a preparative procedure. Octylsilyl columns are used for rapid resolution and improved detection of minor or low ultraviolet-absorbing components in the fractions. For example, monoenoic fatty acids with up to 32 carbons have been detected in bovine brain glycerophospholipids. Specific radioactivities of 3H- and 14C-labeled fatty acids and the distribution of radioactivity among acyl groups from complex lipids are measured. The method is not recommended for complete compositional analysis, but is useful for determinations of specific radioactivities during studies on turnover and metabolic conversions of labeled fatty acids.

  17. 40 CFR 721.10074 - Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acetic acid, 2-chloro-, 1-(3,3... Specific Chemical Substances § 721.10074 Acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester. (a... acetic acid, 2-chloro-, 1-(3,3-dimethylcyclohexyl)ethyl ester (PMN P-05-568; CAS No. 477218-59-0) is...

  18. [Fatty acid content of sausages manufactured in Venezuela].

    PubMed

    Araujo de Vizcarrondo, C; Martín, E

    1997-06-01

    The moisture and lipid content as well as the fatty acid composition of sausages were determined. Lipids were extracted and purified with a mixture of cloroform/methanol 2:1. Fatty acids in the lipid extract were methylated with 4% sulfuric acid/methanol solution and later were separated as methyl esters by gas liquid cromatography (GLC). Sausages presented a lipid content between 7.10% for canned sausages and 35.23% for the cocktail type. Most of the fatty acids were monounsatured with oleic acid as the major component with values between 42.54% for ham sausage and 48.83% for francfort type. Satured fatty acids followed, with palmitic acid as the major component in a range between 21.46% and 26.59% for bologna and Polaca sausage respectively. Polyunsaturated fatty acids were present in less quantities with concentration of linoleic acid between 8.5% (cotto salami type) and 12.60% (cocktail type). Turkey and poultry sausages presented a higher content of polyunsaturated and less saturated fatty acids than the other types of sausages studied.

  19. Rapid identification of triterpenoid sulfates and hydroxy fatty acids including two new constituents from Tydemania expeditionis by LC-MS

    PubMed Central

    Zhang, Jian-Long; Kubanek, Julia; Hay, Mark E.; Aalbersberg, William; Ye, Wen-Cai; Jiang, Ren-Wang

    2011-01-01

    Tydemania expeditionis Weber-van Bosse (Udoteaceae) is a weakly calcified green alga. In the present paper, liquid chromatography coupled with photodiode array detection and electrospray mass spectrometry was developed to identify the fingerprint components. A total of four triterpenoid sulfates and three hydroxy fatty acids in the ethyl acetate fraction of the crude extract were structurally characterized on the basis of retention time, online UV spectrum and mass fragmentation pattern. Furthermore, detailed LC-MS analysis revealed two new hydroxy fatty acids, which were then prepared and characterized by extensive NMR analyses. The proposed method provides a scientific and technical platform for the rapid identification of triterpenoid sulfates and hydroxy fatty acids in similar marine algae and terrestrial plants. PMID:21915955

  20. Fatty acids are potential endogenous regulators of aldosterone secretion.

    PubMed

    Goodfriend, T L; Ball, D L; Elliott, M E; Morrison, A R; Evenson, M A

    1991-05-01

    Adrenal glomerulosa cells washed with delipidated albumin produced increased amounts of aldosterone in response to angiotensin-II (AII) or (Bu)2cAMP. Albumin treatment also increased binding of 125I-labeled AII to high affinity binding sites on adrenal cells. Lipid extracts of albumin solutions that were used to wash cells inhibited AII binding and aldosterone responses by washed glomerulosa cells. Chromatographic fractionation and mass spectroscopic analysis indicated that the inhibitors removed from cells by albumin were long chain fatty acids. Exogenous fatty acids not only inhibited AII binding, but they inhibited basal aldosterone production and increments in aldosterone caused by AII or dbcAMP, suggesting an effect on postreceptor steps in aldosteronogenesis. The most potent and most abundant fatty acids removed from adrenal cells were oleic, linoleic, and arachidonic. These fatty acids inhibited at micromolar concentrations in the absence of albumin and at somewhat higher concentrations in its presence. Cells that had been washed, then inhibited by exogenous oleic acid in vitro, were restored to their enhanced responsiveness by a second albumin wash, making it unlikely that cell damage is the mechanism of inhibition by fatty acids. Responses of fasciculata cells were not potentiated by albumin washes, and cortisol production was less sensitive than aldosterone production to exogenous fatty acids. Binding of ANP to glomerulosa cells was not affected by albumin or fatty acids. These results combined with clinical correlations make it plausible that unesterified fatty acids are naturally occurring regulators of the adrenal glomerulosa. Insulin's ability to lower plasma levels of fatty acids may be one way that it causes sodium retention.