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1

Original article Antimicrobial activity of fatty acids  

E-print Network

Original article Antimicrobial activity of fatty acids against Bacillus larvae, the causative agent and unsaturated free fatty acids were tested for their antibiotic activ- ity against Bacillus larvae by the addition of one or more double bonds. The antibiotic activity of fatty acids may make them suitable for use

Paris-Sud XI, Université de

2

Antitumor activity of unsaturated fatty acid esters of 4'-demethyldeoxypodophyllotoxin.  

PubMed

Unsaturated fatty acid esters of 4'-demethyldeoxypodophyllotoxin (DDPT) were prepared and tested for antitumor activity. The esters showed increased in vivo antitumor activity despite the lower in vitro activity than DDPT. Especially, the ester (DFE12) of all-cis-11,14-eicosadienoic acid was much better (IR, 83%) than VP-16 (IR, 60%) without loss of body weight. Unsaturated fatty acids could be evaluated to be good carrier vehicles of DDPT. PMID:12873481

You, Young-Jae; Kim, Yong; Nam, Nguyen-Hai; Ahn, Byung-Zun

2003-08-18

3

Antiproliferative activity of synthetic fatty acid amides from renewable resources.  

PubMed

In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line-the most aggressive CNS cancer. PMID:25510639

Dos Santos, Daiane S; Piovesan, Luciana A; D'Oca, Caroline R Montes; Hack, Carolina R Lopes; Treptow, Tamara G M; Rodrigues, Marieli O; Vendramini-Costa, Débora B; Ruiz, Ana Lucia T G; de Carvalho, João Ernesto; D'Oca, Marcelo G Montes

2015-01-15

4

Activation of fatty acids by non-glyoxysomal peroxisomes  

Microsoft Academic Search

Peroxisomes from mung-bean hypocotyls catalyze, in the presence of fatty acids, CoASH, ATP, and MgCl2, the formation of acyl-CoA, AMP, and pyrophosphate in a 1:1:1 stoichiometry. This observation demonstrates that the peroxisomes of mung-bean hypocotyls possess an acyl-CoA synthetase (EC 6.2.1.3) for fatty-acid activation. Acyl-CoA synthetase activity is associated with the non-glyoxysomal peroxisomes from various tissues. The acyl-CoA synthetase of

H. Gerbling; B. Gerhardt

1987-01-01

5

Fatty Acid Synthetase Activity in Mycobacterium phlei: Regulation by Polysaccharides  

PubMed Central

The multienzyme complex from Mycobacterium phlei which catalyzes the synthesis of long chain fatty acids from acetyl-CoA and malonyl-CoA requires a heat-stable fraction (stimulating factor, SF) for activity. Fractionation of heat-treated M. phlei extracts affords two stimulatory subfractions, one of which (SF2) can be replaced by FMN. The other (SF1) is further separable into 3 polysaccharides (PSI, PSII, and PSIII). PSI contains about 95% 3-O-methylmannose and 5% mannose; the sugar composition of PSII and PSIII is about 55% 6-O-methylglucose and 45% glucose for both. Each of the three purified polysaccharides, in combination with FMN, substitutes for the crude stimulating factor. The polysaccharides exert their effect on the fatty acid synthetase by lowering the Km for acetyl-CoA about 50-fold. PMID:5276305

Ilton, M.; Jevans, A. W.; McCarthy, E. D.; Vance, D.; White, H. B.; Bloch, Konrad

1971-01-01

6

Reconciling Ligase Ribozyme Activity with Fatty Acid Vesicle Stability  

PubMed Central

The “RNA world” and the “Lipid world” theories for the origin of cellular life are often considered incompatible due to the differences in the environmental conditions at which they can emerge. One obstacle resides in the conflicting requirements for divalent metal ions, in particular Mg2+, with respect to optimal ribozyme activity, fatty acid vesicle stability and protection against RNA strand cleavage. Here, we report on the activity of a short L1 ligase ribozyme in the presence of myristoleic acid (MA) vesicles at varying concentrations of Mg2+. The ligation rate is significantly lower at low-Mg2+ conditions. However, the loss of activity is overcompensated by the increased stability of RNA leading to a larger amount of intact ligated substrate after long reaction periods. Combining RNA ligation assays with fatty acid vesicles we found that MA vesicles made of 5 mM amphiphile are stable and do not impair ligase ribozyme activity in the presence of approximately 2 mM Mg2+. These results provide a scenario in which catalytic RNA and primordial membrane assembly can coexist in the same environment. PMID:25513761

Anella, Fabrizio; Danelon, Christophe

2014-01-01

7

Reconciling ligase ribozyme activity with Fatty Acid vesicle stability.  

PubMed

The "RNA world" and the "Lipid world" theories for the origin of cellular life are often considered incompatible due to the differences in the environmental conditions at which they can emerge. One obstacle resides in the conflicting requirements for divalent metal ions, in particular Mg2+, with respect to optimal ribozyme activity, fatty acid vesicle stability and protection against RNA strand cleavage. Here, we report on the activity of a short L1 ligase ribozyme in the presence of myristoleic acid (MA) vesicles at varying concentrations of Mg2+. The ligation rate is significantly lower at low-Mg2+ conditions. However, the loss of activity is overcompensated by the increased stability of RNA leading to a larger amount of intact ligated substrate after long reaction periods. Combining RNA ligation assays with fatty acid vesicles we found that MA vesicles made of 5 mM amphiphile are stable and do not impair ligase ribozyme activity in the presence of approximately 2 mM Mg2+. These results provide a scenario in which catalytic RNA and primordial membrane assembly can coexist in the same environment. PMID:25513761

Anella, Fabrizio; Danelon, Christophe

2014-01-01

8

Short- and medium-chain fatty acids exhibit antimicrobial activity for oral microorganisms  

PubMed Central

Objectives This study assessed the antibacterial activity of short-, medium-, and long-chain fatty acids against various oral microorganisms. Methods The short-chain fatty acids [formic acid (C1), acetic acid (C2), propionic acid (C3), butyric acid (C4), isobutyric acid (C4), isovaleric acid (C5), hexanoic acid (C6)], medium-chain fatty acids [octanoic acid (C8), capric acid (C10), lauric acid (12)], and long-chain fatty acids [myristic acid (C14), palmitic acid (C16)], were investigated for antimicrobial activity against Streptococcus mutans, S. gordonii, S. sanguis, Candida albicans, Aggregatibacter actinomycetemcomitans, Fusobacterium nucleatum, and Porphyromonas gingivalis. Results The data demonstrated that the fatty acids exhibited patterns of inhibition against oral bacteria with some specificity that appeared related more to the bacterial species that the general structural characteristics of the microorganism. As a group the fatty acids were much less effective against C. albicans than the oral bacteria, with effectiveness limited to hexanoic, octanoic, and lauric acids. Formic acid, capric, and lauric acids were broadly inhibitory for the bacteria. Interestingly, fatty acids that are produced at metabolic end-products by a number of these bacteria, were specifically inactive against the producing species, while substantially inhibiting the growth of other oral microorganisms. Conclusions The results indicate that the antimicrobial activity of short-chain fatty acids (SCFAs), medium-chain fatty acids (MCFAs), long-chain fatty acids (LCFAs) could influence the microbial ecology in the oral cavity via at least 2 potential pathways. First, the agents delivered exogenously as therapeutic adjuncts could be packaged to enhance a microbial-regulatory environment in the subgingival sulcus. Second, it would be the intrinsic nature of these fatty acid inhibitors in contributing to the characteristics of the microbial biofilms, their evolution, and emergence of species within the biofilms. Further studies on these functions are required to better understand the nature of these potential microbial interactions in the biofilms. PMID:21333271

Huang, Chifu B.; Altimova, Yelena; Myers, Taylor M.; Ebersole, Jeffrey L.

2011-01-01

9

Brain fatty acid synthase activates PPARalpha to maintain energy homeostasis.  

PubMed

Central nervous system control of energy balance affects susceptibility to obesity and diabetes, but how fatty acids, malonyl-CoA, and other metabolites act at this site to alter metabolism is poorly understood. Pharmacological inhibition of fatty acid synthase (FAS), rate limiting for de novo lipogenesis, decreases appetite independently of leptin but also promotes weight loss through activities unrelated to FAS inhibition. Here we report that the conditional genetic inactivation of FAS in pancreatic beta cells and hypothalamus produced lean, hypophagic mice with increased physical activity and impaired hypothalamic PPARalpha signaling. Administration of a PPARalpha agonist into the hypothalamus increased PPARalpha target genes and normalized food intake. Inactivation of beta cell FAS enzyme activity had no effect on islet function in culture or in vivo. These results suggest a critical role for brain FAS in the regulation of not only feeding, but also physical activity, effects that appear to be mediated through the provision of ligands generated by FAS to PPARalpha. Thus, 2 diametrically opposed proteins, FAS (induced by feeding) and PPARalpha (induced by starvation), unexpectedly form an integrative sensory module in the central nervous system to orchestrate energy balance. PMID:17694178

Chakravarthy, Manu V; Zhu, Yimin; López, Miguel; Yin, Li; Wozniak, David F; Coleman, Trey; Hu, Zhiyuan; Wolfgang, Michael; Vidal-Puig, Antonio; Lane, M Daniel; Semenkovich, Clay F

2007-09-01

10

Fatty acid extracts from Lucilia sericata larvae promote murine cutaneous wound healing by angiogenic activity  

PubMed Central

Background fatty acids are considered to be effective components to promote wound healing and Lucilia sericata larvae are applied clinically to treat intractable wounds. We aimed to investigat the effect of fatty acid extracts from dried Lucilia sericata larvae on murine cutaneuous wound healing as well as angiogenesis. Results On day 7 and 10 after murine acute excision wounds creation, the percent wound contraction of fatty acid extracts group was higher than that of vaseline group. On day 3, 7 and 10 after wounds creation, the wound healing quality of fatty acid extracts group was better than that of vaseline group on terms of granulation formation and collagen organization. On day 3 after wounds creation, the micro vessel density and vascular endothelial growth factor expression of fatty acid extracts group were higher than that of vaseline group. Component analysis of the fatty acid extracts by gas chromatography-mass spectrometry showed there were 10 kinds of fatty acids in total and the ratio of saturated fatty acid, monounsaturated fatty acid and polyunsaturated fatty acid (PUFA) was: 20.57%:60.32%:19.11%. Conclusions Fatty acid extracts from dried Lucilia sericata larvae, four fifths of which are unsaturated fatty acids, can promote murine cutaneous wound healing probably resulting from the powerful angiogenic activity of the extracts. PMID:20211009

2010-01-01

11

Anti-cancer Activities of ?-6 Polyunsaturated Fatty Acids  

PubMed Central

The ?-3 and ?-6 polyunsaturated fatty acids (PUFAs) are two major families of PUFAs present as essential cellular components which possess diverse bioactivities. The ?-3s, mainly found in seafood, are associated with many beneficial effects on human health, while the ?-6s are more abundant in our daily diet and could be implicated in many pathological processes including cancer development. Increasing evidence suggests that the adverse effects of ?-6s may be largely attributed to arachidonic acid (AA, a downstream ?-6) and the metabolite prostaglandin E2 (PGE2) that stems from its cyclooxygenase (COX)-catalyzed lipid peroxidation. On the other hand, two of AA’s upstream ?-6s, ?-linolenic acid (GLA) and dihomo-?-linolenic acid (DGLA), are shown to possess certain anti-cancer activities, including inducing cell apoptosis and inhibiting cell proliferation. In this paper, we review the documented anti-cancer activities of ?-6 PUFAs, including the recent findings regarding the anti-cancer effects of free radical-mediated DGLA peroxidation. The possible mechanisms and applications of DGLA (and other ?-6s) in inducing anti-cancer activity are also discussed. Considering the wide availability of ?-6s in our daily diet, the study of the potential beneficial effect of ?-6 PUFAs may guide us to develop an ?-6–based diet care strategy for cancer prevention and treatment. PMID:24923568

Xu, Yi; Qian, Steven Y.

2014-01-01

12

Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation  

PubMed Central

Acetyl CoA carboxylase (ACC1 & ACC2) generates malonyl CoA, a substrate for de novo lipogenesis (DNL) and an inhibitor of mitochondrial fatty acid ?-oxidation (FAO). Malonyl CoA is also a substrate for microsomal fatty acid elongation, an important pathway for saturated (SFA), mono- (MUFA) and polyunsaturated fatty acid (PUFA) synthesis. Despite the interest in ACC as a target for obesity and cancer therapy, little attention has been given to the role ACC plays in long chain fatty acid synthesis. This report examines the effect of pharmacological inhibition of ACC on DNL & palmitate (16:0) and linoleate (18:2,n-6) metabolism in HepG2 and LnCap cells. The ACC inhibitor, soraphen A, lowers cellular malonyl CoA, attenuates DNL and the formation of fatty acid elongation products derived from exogenous fatty acids, i.e., 16:0 & 18:2,n-6; IC50 ~ 5 nM. Elevated expression of fatty acid elongases (Elovl5, Elovl6) or desaturases (FADS1, FADS2) failed to override the soraphen A effect on SFA, MUFA or PUFA synthesis. Inhibition of fatty acid elongation leads to the accumulation of 16- and 18-carbon unsaturated fatty acids derived from 16:0 and 18:2,n-6, respectively. Pharmacological inhibition of ACC activity will not only attenuate DNL and induce FAO, but will also attenuate the synthesis of very long chain saturated, mono- and polyunsaturated fatty acids. PMID:21184748

Jump, Donald B.; Torres-Gonzalez, Moises; Olson, L. Karl

2010-01-01

13

Esterification of fatty acid over Tunisian acid activated clay: kinetic study.  

PubMed

Tunisian acid activated clay was investigated as catalyst in the esterification of stearic acid with ethyl alcohol, carried out in a semi-continuous reactor. Kinetic study shows that the reaction is first order with respect to acid concentration. The activation energy found was 21 kJ/mol. This result suggests that the reaction process was controlled by a diffusional step. A kinetic model, giving the apparent constant rate as a function of temperature and catalyst concentration, has been established. This equation has been then successfully applied for a complex mixture of fatty acid. PMID:21606617

Neji, Soumaya Bouguerra; Trabelsi, Mahmoud; Frikha, Mohamed H

2011-01-01

14

Fatty acid composition, glutathione peroxidase and superoxide dismutase activity and total antioxidant activity of avian semen.  

PubMed

This work demonstrates that spermatozoa from five avian species (chicken, turkey, guinea fowl, duck and goose) are all characterised by high proportions of polyunsaturated fatty acids, from 46 (turkey) to 55% (duck) of total. For each of the species, the most abundant fatty acids were arachidonic (20:4n-6) and docosatetraenoic (22:4n-6) acids, representing between 22 (turkey) and 40% (chicken) of total. Significant activities of the major isozymes of superoxide dismutase and glutathione peroxidase, which protect against the peroxidation associated with high degree of fatty acid unsaturation, were found in spermatozoa from all species. The seminal plasma also had these activities and showed additional mechanisms for protecting spermatozoa from peroxidation. In general terms, these lipid and enzyme proteins were similar between the five avian species and different from those reported for mammalian sperm. PMID:9787812

Surai, P F; Blesbois, E; Grasseau, I; Chalah, T; Brillard, J P; Wishart, G J; Cerolini, S; Sparks, N H

1998-07-01

15

Structural Basis for Activation of Fatty Acid Binding Protein 4  

PubMed Central

Summary Fatty acid binding protein 4 (FABP4) delivers ligands from the cytosol to the nuclear receptor PPAR? in the nucleus, thereby enhancing the transcriptional activity of the receptor. Notably, FABP4 binds multiple ligands with a similar affinity but its nuclear translocation is activated only by specific compounds. To gain insight into the structural features that underlie the ligand-specificity in activation of the nuclear import of FABP4, we solved the crystal structures of the protein complexed with two compounds that induce its nuclear translocation, and compared these to the apo-protein and to FABP4 structures bound to non-activating ligands. Examination of these structures indicates that activation coincides with closure of a portal loop phenylalanine sidechain, contraction of the binding pocket, a subtle shift in a helical domain containing the nuclear localization signal of the protein, and a resultant change in oligomeric state that exposes the nuclear localization signal to the solution. Comparisons of backbone displacements induced by activating ligands with a measure of mobility derived from TLS (translation/libration/screw) refinement, and with a composite of slowest normal modes of the apo state suggest that the helical motion associated with the activation of the protein is part of the repertoire of the equilibrium motions of the apo-protein, i.e. that ligand-binding does not induce the activated configuration but serves to stabilize it. Nuclear import of FABP4 can thus be understood in terms of the pre-existing equilibrium hypothesis of ligand binding. PMID:17761196

Gillilan, Richard E.; Ayers, Stephen D.; Noy, Noa

2007-01-01

16

Epicuticular Wax Accumulation and Fatty Acid Elongation Activities Are Induced during Leaf Development of Leeks  

Microsoft Academic Search

Epicuticular wax production was evaluated along the length of expanding leek (Allium porrum L.) leaves to gain insight into the regulation of wax production. Leaf segments from the bottom to the top were analyzed for (a) wax composition and load; (b) microso- mal fatty acid elongase, plastidial fatty acid synthase, and acyl-acyl carrier protein (ACP) thioesterase activities; and (c) tissue

Yoon Rhee; Alenka Hlousek-Radojcic; Jayakumar Ponsamuel; Dehua Liu; Dusty Post-Beittenmiller

1998-01-01

17

Chronic hexosamine flux stimulates fatty acid oxidation by activating AMP-activated protein kinase in adipocytes.  

PubMed

The hexosamine biosynthesis pathway (HBP) serves as a nutrient sensor and has been implicated in the development of type 2 diabetes. We previously demonstrated that fatty acid oxidation was enhanced in transgenic mouse adipocytes, wherein the rate-limiting enzyme of the HBP, glutamine:fructose-6-phosphate amidotransferase (GFA), was overexpressed. To explore the molecular mechanism of the HBP-induced fatty acid oxidation in adipocytes, we studied AMP-activated protein kinase (AMPK), an energy sensor that stimulates fatty acid oxidation by regulating acetyl-CoA carboxylase (ACC) activity. Phosphorylation and activity of AMPK were increased in transgenic fat pads and in 3T3L1 adipocytes treated with glucosamine to stimulate hexosamine flux. Glucosamine also stimulated phosphorylation of ACC and fatty acid oxidation in 3T3L1 adipocytes, and these stimulatory effects were diminished by adenovirus-mediated expression of a dominant negative AMPK in 3T3L1 adipocytes. Conversely, blocking the HBP with a GFA inhibitor reduced AMPK activity, ACC phosphorylation, and fatty acid oxidation. These changes are not explained by alterations in the cellular AMP/ATP ratio. Further demonstrating that AMPK is regulated by the HBP, we found that AMPK was recognized by succinylated wheat germ agglutinin, which specifically binds O-GlcNAc. The levels of AMPK in succinylated wheat germ agglutinin precipitates correlated with hexosamine flux in mouse fat pads and 3T3L1 adipocytes. Moreover, removal of O-GlcNAc by hexosaminidase reduced AMPK activity. We conclude that chronically high hexosamine flux stimulates fatty acid oxidation by activating AMPK in adipocytes, in part through O-linked glycosylation. PMID:17227772

Luo, Bai; Parker, Glendon J; Cooksey, Robert C; Soesanto, Yudi; Evans, Mark; Jones, Deborah; McClain, Donald A

2007-03-01

18

Bactericidal Activity of the Human Skin Fatty Acid cis-6-Hexadecanoic Acid on Staphylococcus aureus  

PubMed Central

Human skin fatty acids are a potent aspect of our innate defenses, giving surface protection against potentially invasive organisms. They provide an important parameter in determining the ecology of the skin microflora, and alterations can lead to increased colonization by pathogens such as Staphylococcus aureus. Harnessing skin fatty acids may also give a new avenue of exploration in the generation of control measures against drug-resistant organisms. Despite their importance, the mechanism(s) whereby skin fatty acids kill bacteria has remained largely elusive. Here, we describe an analysis of the bactericidal effects of the major human skin fatty acid cis-6-hexadecenoic acid (C6H) on the human commensal and pathogen S. aureus. Several C6H concentration-dependent mechanisms were found. At high concentrations, C6H swiftly kills cells associated with a general loss of membrane integrity. However, C6H still kills at lower concentrations, acting through disruption of the proton motive force, an increase in membrane fluidity, and its effects on electron transfer. The design of analogues with altered bactericidal effects has begun to determine the structural constraints on activity and paves the way for the rational design of new antistaphylococcal agents. PMID:24709265

Cartron, Michaël L.; England, Simon R.; Chiriac, Alina Iulia; Josten, Michaele; Turner, Robert; Rauter, Yvonne; Hurd, Alexander; Sahl, Hans-Georg; Jones, Simon

2014-01-01

19

Expression and characterization of an epoxide hydrolase from Anopheles gambiae with high activity on epoxy fatty acids  

E-print Network

on epoxy fatty acids Jiawen Xu, Christophe Morisseau, Bruce D. Hammock* Department of Entomology hydrolase Anopheles gambiae Epoxy fatty acids a b s t r a c t In insects, epoxide hydrolases (EHs) playEH had the greatest activity on long chain epoxy fatty acids such as 14,15-epoxyeicosatrienoic acids (14

Hammock, Bruce D.

20

Fatty acid synthase plays a role in cancer metabolism beyond providing fatty acids for phospholipid synthesis or sustaining elevations in glycolytic activity  

SciTech Connect

Fatty acid synthase is over-expressed in many cancers and its activity is required for cancer cell survival, but the role of endogenously synthesized fatty acids in cancer is unknown. It has been suggested that endogenous fatty acid synthesis is either needed to support the growth of rapidly dividing cells, or to maintain elevated glycolysis (the Warburg effect) that is characteristic of cancer cells. Here, we investigate both hypotheses. First, we compared utilization of fatty acids synthesized endogenously from {sup 14}C-labeled acetate to those supplied exogenously as {sup 14}C-labeled palmitate in the culture medium in human breast cancer (MCF-7 and MDA-MB-231) and untransformed breast epithelial cells (MCF-10A). We found that cancer cells do not produce fatty acids that are different from those derived from exogenous palmitate, that these fatty acids are esterified to the same lipid and phospholipid classes in the same proportions, and that their distribution within neutral lipids is not different from untransformed cells. These results suggest that endogenously synthesized fatty acids do not fulfill a specific function in cancer cells. Furthermore, we observed that cancer cells excrete endogenously synthesized fatty acids, suggesting that they are produced in excess of requirements. We next investigated whether lipogenic activity is involved in the maintenance of high glycolytic activity by culturing both cancer and non-transformed cells under anoxic conditions. Although anoxia increased glycolysis 2–3 fold, we observed no concomitant increase in lipogenesis. Our results indicate that breast cancer cells do not have a specific qualitative or quantitative requirement for endogenously synthesized fatty acids and that increased de novo lipogenesis is not required to sustain elevations in glycolytic activity induced by anoxia in these cells. - Highlights: • Fatty acid synthase (FASN) is over-expressed in cancer but its function is unknown. • We compare utilization of fatty acids produced by FASN to those derived exogenously. • Cancer cells do not have a specific requirement for fatty acids produced by FASN. • Fatty acids produced by FASN are in excess of cell requirements and are excreted. • Increased FASN activity is not required to sustain elevations in glycolysis.

Hopperton, Kathryn E., E-mail: kathryn.hopperton@mail.utoronto.ca [Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, Toronto, ON, Canada M5S 3E2 (Canada); Duncan, Robin E., E-mail: robin.duncan@uwaterloo.ca [Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, Toronto, ON, Canada M5S 3E2 (Canada); Bazinet, Richard P., E-mail: richard.bazinet@utoronto.ca [Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, Toronto, ON, Canada M5S 3E2 (Canada); Archer, Michael C., E-mail: m.archer@utoronto.ca [Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, Toronto, ON, Canada M5S 3E2 (Canada); Department of Medical Biophysics, Faculty of Medicine, University of Toronto, Toronto, ON, Canada M5S 3E2 (Canada)

2014-01-15

21

Plant fatty acid hydroxylases  

DOEpatents

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.

Somerville, Chris (Portola Valley, CA); Broun, Pierre (Burlingame, CA); van de Loo, Frank (Lexington, KY)

2001-01-01

22

Fatty Acid Synthase Inhibition Activates AMP-Activated Protein Kinase in SKOV3 Human Ovarian Cancer Cells  

Microsoft Academic Search

1 Pathology, 2 Neuroscience, 3 Neurology, 4 Oncology, and 5 Abstract Fatty acid synthase (FAS), the enzyme responsible for the de novo synthesis of fatty acids, is highly expressed in ovarian cancers and most common human carcinomas. Inhibition of FAS and activation of AMP-activated protein kinase (AMPK) have been shown to be cytotoxic to human cancer cells in vitro and

Weibo Zhou; Leslie E. Landree; Jagan N. Thupari; Michael L. Pinn; Tsion Bililign; Eun Kyoung Kim; Aravinda Vadlamudi; Susan M. Medghalchi; Rajaa El Meskini; Gabriele V. Ronnett; Craig A. Townsend; Francis P. Kuhajda

2007-01-01

23

Fatty acids regulate CREBh via transcriptional mechanisms that are dependent on proteasome activity and insulin  

PubMed Central

Excess fatty acids are closely associated with metabolic dysfunction. The deleterious effects of fatty acids relate, in part, to their ability to up-regulate proinflammatory cytokines and propagate a state of systemic inflammation. CREBh is a recently identified transcription factor that appears to be required for hepatic synthesis of C-reactive protein (CRP). Recent data suggest that fatty acids can up-regulate CREBh, thus establishing a potential molecular link between fatty acids and inflammation. The aim of the current study was to examine the nature and mechanisms of fatty acid-mediated regulation of CREBh. H4IIE liver cells were incubated in the absence or presence of varying concentrations (50–500 ?M) of albumin-bound, long-chain saturated (palmitate, stearate) or unsaturated (oleate, linoleate) fatty acids (1–16 hours). All fatty acids significantly increased CREBh gene expression via transcriptional mechanisms, at concentrations as low as 50 ?M. Palmitate- or oleate-mediated upregulation of CREBh was not inhibited by triacsin C, an inhibitor of long-chain fatty acyl CoA synthetase, or by the PPAR? antagonist, MK886. Inhibition of proteasome activity with MG132 or lactacystin, or inclusion of insulin reduced palmitate- and oleate-mediated increases in CREBh mRNA. Finally, we examined fatty acid regulation of CREBh in vivo. Male Wistar rats were exposed to a 4-hour pancreatic clamp combined with infusion of saline or a mixed lipid emulsion. CREBh mRNA and protein were significantly increased in rats exposed to the lipid infusion compared to the saline group. Collectively, these results may have important implications for metabolic diseases characterized by excess fatty acids, insulin resistance and inflammation. PMID:20607591

Gentile, CL; Wang, D; Pfaffenbach, KT; Cox, R; Wei, Y; Pagliassotti, MJ

2011-01-01

24

Fatty acid analogs  

DOEpatents

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.

Elmaleh, David R. (Newton Center, MA); Livni, Eli (Brookline, MA)

1985-01-01

25

AMP-Activated Kinase Restricts Rift Valley Fever Virus Infection by Inhibiting Fatty Acid Synthesis  

PubMed Central

The cell intrinsic innate immune responses provide a first line of defense against viral infection, and often function by targeting cellular pathways usurped by the virus during infection. In particular, many viruses manipulate cellular lipids to form complex structures required for viral replication, many of which are dependent on de novo fatty acid synthesis. We found that the energy regulator AMPK, which potently inhibits fatty acid synthesis, restricts infection of the Bunyavirus, Rift Valley Fever Virus (RVFV), an important re-emerging arthropod-borne human pathogen for which there are no effective vaccines or therapeutics. We show restriction of RVFV both by AMPK and its upstream activator LKB1, indicating an antiviral role for this signaling pathway. Furthermore, we found that AMPK is activated during RVFV infection, leading to the phosphorylation and inhibition of acetyl-CoA carboxylase, the first rate-limiting enzyme in fatty acid synthesis. Activating AMPK pharmacologically both restricted infection and reduced lipid levels. This restriction could be bypassed by treatment with the fatty acid palmitate, demonstrating that AMPK restricts RVFV infection through its inhibition of fatty acid biosynthesis. Lastly, we found that this pathway plays a broad role in antiviral defense since additional viruses from disparate families were also restricted by AMPK and LKB1. Therefore, AMPK is an important component of the cell intrinsic immune response that restricts infection through a novel mechanism involving the inhibition of fatty acid metabolism. PMID:22532801

Moser, Theresa S.; Schieffer, Daniel; Cherry, Sara

2012-01-01

26

Epicuticular wax accumulation and fatty acid elongation activities are induced during leaf development of leeks  

PubMed

Epicuticular wax production was evaluated along the length of expanding leek (Allium porrum L.) leaves to gain insight into the regulation of wax production. Leaf segments from the bottom to the top were analyzed for (a) wax composition and load; (b) microsomal fatty acid elongase, plastidial fatty acid synthase, and acyl-acyl carrier protein (ACP) thioesterase activities; and (c) tissue and cellular morphological changes. The level of total wax, which was low at the bottom, increased 23-fold along the length of the leaf, whereas accumulation of the hentriacontan-16-one increased more than 1000-fold. The onset of wax accumulation was not linked to cell elongation but, rather, occurred several centimeters above the leaf base. Peak microsomal fatty acid elongation activity preceded the onset of wax accumulation, and the maximum fatty acid synthase activity was coincident with the onset. The C16:0- and C18:0-ACP-hydrolyzing activities changed relatively little along the leaf, whereas C18:1-ACP-hydrolyzing activity increased slightly prior to the peak elongase activity. Electron micrographic analyses revealed that wax crystal formation was asynchronous among cells in the initial stages of wax deposition, and morphological changes in the cuticle and cell wall preceded the appearance of wax crystals. These studies demonstrated that wax production and microsomal fatty acid elongation activities were induced within a defined and identifiable region of the expanding leek leaf and provide the foundation for future molecular studies. PMID:9501123

Rhee; Hlousek-Radojcic; Ponsamuel; Liu; Post-Beittenmiller

1998-03-01

27

Epicuticular Wax Accumulation and Fatty Acid Elongation Activities Are Induced during Leaf Development of Leeks1  

PubMed Central

Epicuticular wax production was evaluated along the length of expanding leek (Allium porrum L.) leaves to gain insight into the regulation of wax production. Leaf segments from the bottom to the top were analyzed for (a) wax composition and load; (b) microsomal fatty acid elongase, plastidial fatty acid synthase, and acyl-acyl carrier protein (ACP) thioesterase activities; and (c) tissue and cellular morphological changes. The level of total wax, which was low at the bottom, increased 23-fold along the length of the leaf, whereas accumulation of the hentriacontan-16-one increased more than 1000-fold. The onset of wax accumulation was not linked to cell elongation but, rather, occurred several centimeters above the leaf base. Peak microsomal fatty acid elongation activity preceded the onset of wax accumulation, and the maximum fatty acid synthase activity was coincident with the onset. The C16:0- and C18:0-ACP-hydrolyzing activities changed relatively little along the leaf, whereas C18:1-ACP-hydrolyzing activity increased slightly prior to the peak elongase activity. Electron micrographic analyses revealed that wax crystal formation was asynchronous among cells in the initial stages of wax deposition, and morphological changes in the cuticle and cell wall preceded the appearance of wax crystals. These studies demonstrated that wax production and microsomal fatty acid elongation activities were induced within a defined and identifiable region of the expanding leek leaf and provide the foundation for future molecular studies. PMID:9501123

Rhee, Yoon; Hlousek-Radojcic, Alenka; Ponsamuel, Jayakumar; Liu, Dehua; Post-Beittenmiller, Dusty

1998-01-01

28

Effect of dietary omega-3 and omega-6 fatty acids on clotting activities of Factor V, VII and X in fatty liver haemorrhagic syndrome-susceptible laying hens.  

PubMed

1. The relationship between concentrations of omega-3 and omega-6 fatty acids in plasma and Factor V, VII and X clotting activities was determined using a crossover feeding trial with diets supplemented with either soy oil or flax oil. 2. Laying hens on the soy diet, which is high in omega-6 fatty acids, had substantially higher clotting activity for all three factors compared to laying hens on the flax diet that was high in omega-3 fatty acids. 3. Positive associations were seen between liver haemorrhage score and the percentage of liver weight and between the percentage of liver weight and the severity of haemorrhagic and fatty changes seen on histology. 4. These results support the hypothesis that concentrations of omega-6 and omega-3 fatty acids in plasma affect clotting activity; however, there was no relationship between the extent of liver haemorrhages and the composition of plasma fatty acids. PMID:19637039

Yeh, E; Wood, R D; Leeson, S; Squires, E J

2009-05-01

29

Short-term activation of peroxysome proliferator-activated receptor ?\\/? increases fatty acid oxidation but does not restore insulin action in muscle cells from type 2 diabetic patients  

Microsoft Academic Search

Defective fatty acid oxidation in skeletal muscle is one of the possible causes of insulin resistance. Peroxisome proliferator-activated receptor ? activators are strong inducers of fatty acid oxidation. The aim of this study was to verify whether activation of fatty acid oxidation by PPAR? agonists in human skeletal muscle cells prepared from type 2 diabetic patients could improve the reduced

Cyrille Debard; Delphine Cozzone; Nadège Ricard; Julien Vouillarmet; Emmanuel Disse; Bernadette Husson; Martine Laville; Hubert Vidal

2006-01-01

30

Protein kinase C activation in rat colonic mucosa after diets differing in their fatty acid composition.  

PubMed

We studied the effects of different types of dietary fats on fatty acid composition and activity of protein kinase C (PKC) in rat colonic mucosa. Activation of PKC, a key enzyme in signal transduction and growth regulation, provides a mechanism by which dietary components could be involved in colon carcinogenesis. Male Wistar rats (n = 12/group) were fed a semisynthetic high fat diet (43% of energy) containing either sunflower oil, rapeseed oil, or butter for 4 weeks ad libitum. The control group received a low fat sunflower oil diet (10% of energy). The butter diet increased membrane-associated PKC activity in rat colonic mucosa compared with the low fat control diet (1237 vs. 917 pmol/min per mg prot.; P = 0.028). Mucosal fatty acids reflected dietary fatty acid composition even though there was no clear association between the amount of mucosal fatty acids and PKC activity. More research is needed to elucidate how dietary fatty acids regulate colonic PKC activity. PMID:9103264

Pajari, A M; Rasilo, M L; Mutanen, M

1997-03-19

31

Comparative investigation of volatile fatty acids, soluble glucides and cellulase enzymes activity  

E-print Network

Comparative investigation of volatile fatty acids, soluble glucides and cellulase enzymes activity and cellulase enzymes activity in the rumen. The experiment used four males of each species, weighing 275 kg and cellulase didn't differ significantly between the studied species, and the highest enzymatic activity of p1

Paris-Sud XI, Université de

32

Bactericidal activity of alkaline salts of fatty acids towards bacteria associated with poultry processing  

Technology Transfer Automated Retrieval System (TEKTRAN)

Antibacterial activity of alkaline salts of caproic, caprylic, capric, lauric, and myristic acids were determined using the agar diffusion assay. A 0.5M concentration of each fatty acid (FA) was dissolved in 1.0 M potassium hydroxide (KOH), and pH of the mixtures was adjusted to 10.5 with citric aci...

33

Molecular Recognition of Fatty Acids by Peroxisome Proliferator–Activated Receptors  

Microsoft Academic Search

The peroxisome proliferator–activated receptors (PPARs) are nuclear receptors for fatty acids (FAs) that regulate glucose and lipid homeostasis. We report the crystal structure of the PPAR? ligand-binding domain (LBD) bound to either the FA eicosapentaenoic acid (EPA) or the synthetic fibrate GW2433. The carboxylic acids of EPA and GW2433 interact directly with the activation function 2 (AF-2) helix. The hydrophobic

H. Eric Xu; Millard H Lambert; Valerie G Montana; Derek J Parks; Steven G Blanchard; Peter J Brown; Daniel D Sternbach; Jürgen M Lehmann; G. Bruce Wisely; Timothy M Willson; Steven A Kliewer; Michael V Milburn

1999-01-01

34

Insecticidal activity of fatty acid-rich Turkish bryophyte extracts against Sitophilus granarius (Coleoptera: Curculionidae).  

PubMed

The composition of fatty acids and insecticidal effects was performed for the Turkish mosses Dicranum scoparium, Hypnum cupressiforme, Polytrichastrum formosum, Homalothecium lutescens and the Turkish liverwort Conocephalum conicum. All structures were determined by means of gas chromatography and gas chromatography-mass spectrometry techniques. The determination of fatty acids was done using a simple and mild method that utilized different solvent extractions ranging from nonpolar to polar solvents (hexane, dichloromethane, chloroform, ethyl acetate and methanol, respectively), and the samples were powdered with and without liquid nitrogen. The correlations between the saturated and unsaturated fatty acid contents depending on the solvent polarity and their crushing process by liquid nitrogen were observed. The insecticidal activity of the bryophytes was analyzed by using the methanol, hexane and esterified methanol extracts. The hexane extracts of Polytrichastrum formosum showed the highest insecticidal activity (70.33%) against Sitophilus granarius. Contact toxicity activities of lauric, myristic and palmitic acids besides single dose studies of the solvent extracts were carried out. The highest mortality rate (53.34%) was obtained from the myristic acid among the tested pure fatty acids. The activities of palmitic and lauric acids were 17.75% and 4.32%, respectively. PMID:24050694

Abay, Gokhan; Altun, Muhammed; Karakoç, Ömer Cem; Gül, Fatih; Demirtas, Ibrahim

2013-12-01

35

Free fatty acids inhibit the activity of Clostridium histolyticum collagenase and human neutrophil elastase.  

PubMed

We investigated the ability of free fatty acids to inhibit the activity of Clostridium histolyticum collagenase (EC 3.4.24.3) and human neutrophil elastase (EC 3.4.21.37). We determined the activity of collagenase by degradation of resorufin-labeled casein fluorimetrically. The determination of the elastase activity was performed by a spectrophotometric method using a 4-nitroanilide peptide substrate. We found that most of the tested fatty acids inhibited collagenase at concentrations between 50 microM and 500 microM. For elastase we found an inhibition of the activity at concentrations between 500 nM and 50 microM. The most potent inhibitory fatty acids of both enzymes differed. Thus, as a result for collagenase we can assume that the saturated fatty acids with C(16)-C(19) were the most potent ones. For elastase the inhibition rate of unsaturated acids was much higher than the rate of the saturated ones. The highly active erucic acid with an IC(50) value of 450 nM (elastase) is remarkable. PMID:12357383

Rennert, Beate; Melzig, Matthias F

2002-09-01

36

[The influence of the dietary polyunsaturated fatty acids on the phagocyte's functional activity in rats].  

PubMed

The influence of dietary polyunsaturated fatty acids on the superoxid anion production by peritoneal macrophages and phagocytosis by blood neutrophiles in male Wistar rats weighting 127.0 +/- 3.2 r was investigated after 3 months feeding. Rats fed isocaloric purified diets contained 24% fat representing combinations of lard, sunflower oil and fish oil (eiconol) providing the ratios of w6/w3 fatty acids equal 49.0; 6.1; 1.1. The increasing of superoxide formed by peritoneal macrophages and phagocytic activity of neutrophiles in the group received diet with the minimal ratios of w6/w3 fatty acids compared to that in rats fed diet with ratio 49.0 was noted. The increased activity of mononuclear-phagocytic system was confirmed by morphological investigation of peripheral lymphoid organs. PMID:12968296

Trushina, E N; Mustafina, O K; Kulakova, S N

2003-01-01

37

Antioxidant activities and fatty acid composition of wild grown myrtle (Myrtus communis L.) fruits.  

PubMed

The fruits of eight myrtles, Myrtus communis L. accessions from the Mediterranean region of Turkey were evaluated for their antioxidant activities and fatty acid contents. The antioxidant activities of the fruit extracts were determined by using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and beta-carotene-linoleic acid assays. The fatty acid contents of fruits were determined by using gas chromatography. The methanol extracts of fruits exhibited a high level of free radical scavenging activity. There was a wide range (74.51-91.65%) of antioxidant activity among the accessions in the beta-carotene-linoleic acid assay. The amount of total phenolics (TP) was determined to be between 44.41-74.44 mug Gallic acid equivalent (GAE)/mg, on a dry weight basis. Oleic acid was the dominant fatty acid (67.07%), followed by palmitic (10.24%), and stearic acid (8.19%), respectively. These results suggest the future utilization of myrtle fruit extracts as food additives or in chemoprevention studies. PMID:20548930

Serce, Sedat; Ercisli, Sezai; Sengul, Memnune; Gunduz, Kazim; Orhan, Emine

2010-01-01

38

Three new fatty acids from the roots of Boehmeria nivea (L.) Gaudich and their antifungal activities.  

PubMed

Three new unsaturated fatty acids, (Z)-9,10,11-trihydroxy-12-octadecenoic acid (1), (Z)-7,8,9-trihydroxy-10-hexadecenoic acid (2) and (Z)-12-keto-7,8,9-trihydroxy-10-hexadecenoic acid (3) were isolated from the roots of Boehmeria nivea (L.) Gaudich, along with a known unsaturated fatty acid, (E)-8,11,12-trihydroxy-9-octadecenoic acid (4). The structures of the new compounds were established by HR ESI-MS, (1)H, (13)C, 2D ((1)H-(1)H COSY, HSQC, HMBC) NMR experiments. The known compound was identified by a comparison of its spectral data with published references. The three new compounds showed some antifungal activities by agar assay. PMID:21409726

Xu, Qiong-Ming; Liu, Yan-Li; Li, Xiao-Ran; Li, Xia; Yang, Shi-Lin

2011-03-01

39

Active role of fatty acid amino acid conjugates in nitrogen metabolidm by Spodoptera litura larvae  

Technology Transfer Automated Retrieval System (TEKTRAN)

Since the first fatty acid amino acid conjugate (FAC) was isolated from regurgitant of Spodoptera exigua larvae in 1997 [volicitin: N-(17-hydroxylinolenoyl)- L-glutamine], their role as elicitors of induced responses in plants has been well documented. However, studies of the biosyntheses as well as...

40

New bioactive fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

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...

41

New Bioactive Fatty Acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

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...

42

Esterification and transesterification of greases to fatty acid methyl esters with highly active diphanylammonium salts  

Technology Transfer Automated Retrieval System (TEKTRAN)

We have conducted an investigation designed to identify alternate catalysts for the production of fatty acid methyl esters (FAME) to be used as biodiesel. Diphenylammonium sulfate (DPAS) and diphenylammonium chloride (DPA-HCl) salts were found to be highly active homogeneous catalysts for the simu...

43

Esterification and Transesterification of greases to fatty acid methyl esters with highly active diphenylamine salts  

Technology Transfer Automated Retrieval System (TEKTRAN)

Diphenylamine sulfate (DPAS) and diphenylamine hydrochloride (DPACl) salts were found to be highly active catalysts for esterification and transesterification of inexpensive greases to fatty acid methyl esters (FAME). In the presence of catalytic amounts of DPAS or DPACl and excess methanol, the fr...

44

Production of Biologically Active Hydroxy Fatty Acids from Vegetable Oils by Pseudomonas aeruginosa PR3  

Technology Transfer Automated Retrieval System (TEKTRAN)

Hydroxy fatty acids have gained industrial attention because of their special properties such as higher viscosity and reactivity compared with other non-hydroxy fatty acids. The bacterial isolate Pseudomonas aeruginosa (PR3) had been reported to produce mono-, di-, and tri-hydroxy fatty acids from ...

45

Production of Biologically Active Hydroxy Fatty Acids by Pseudomonas aeruginosa PR3  

Technology Transfer Automated Retrieval System (TEKTRAN)

Hydroxy fatty acids (HFA) have gained important attentions because of their special properties such as higher viscosity and reactivity compared with other non-hydroxy fatty acids. Pseudomonas aeruginosa (PR3) had been reported to produce mono-, di-, and tri-hydroxy fatty acids from different unsatu...

46

Modulation of fatty acid synthase enzyme activity and expression during hepatitis C virus replication.  

PubMed

The hepatitis C virus (HCV) induces alterations of host cells to facilitate its life cycle. Fatty acid synthase (FASN) is a multidomain enzyme that plays a key role in the biosynthesis of fatty acids and is upregulated during HCV infection. Herein, we applied activity-based protein profiling (ABPP) that allows for the identification of differentially active enzymes in complex proteomic samples, to study the changes in activity of FASN during HCV replication. For this purpose, we used an activity-based probe based on the FASN inhibitor Orlistat, and observed an increase in the activity of FASN in the presence of a subgenomic and a genomic HCV replicon as well as in chimeric SCID/Alb-uPA mice infected with HCV genotype 1a. To study the molecular basis for this increase in FASN activity, we overexpressed individual HCV proteins in Huh7 cells and observed increased expression and activity of FASN in the presence of core and NS4B, as measured by western blots and ABPP, respectively. Triglyceride levels were also elevated in accordance with FASN expression and activity. Lastly, immunofluorescence and ABPP imaging analyses demonstrated that while the abundance and activity of FASN increases significantly in the presence of HCV, its localization does not change. Together these data suggest that the HCV-induced production of fatty acids and neutral lipids is provided by an increase in FASN abundance and activity that is sufficient to allow HCV propagation without transporting FASN to the replication complexes. PMID:23601646

Nasheri, Neda; Joyce, Michael; Rouleau, Yanouchka; Yang, Pengyu; Yao, Shao; Tyrrell, D Lorne; Pezacki, John Paul

2013-04-18

47

Maternal low protein diet in rats programmes fatty acid desaturase activities in the offspring  

Microsoft Academic Search

Summary   Numerous studies show an association between poor fetal growth and adult insulin resistance. Recent studies have shown relation\\u000a between the long chain polyunsaturated fatty acid composition of skeletal muscle membranes and insulin sensitivity. More detailed\\u000a analysis has indicated that the activity of ?5 desaturase is inversely correlated to insulin resistance. The amount of docosahexaenoic\\u000a acid (C22:6n3) is also thought

S. E. Ozanne; N. D. Martensz; C. J. Petry; C. L Loizou; C. N. Hales

1998-01-01

48

Oleic Acid Stimulates Complete Oxidation of Fatty Acids through Protein Kinase A-dependent Activation of SIRT1-PGC1? Complex*  

PubMed Central

Fatty acids are essential components of the dynamic lipid metabolism in cells. Fatty acids can also signal to intracellular pathways to trigger a broad range of cellular responses. Oleic acid is an abundant monounsaturated omega-9 fatty acid that impinges on different biological processes, but the mechanisms of action are not completely understood. Here, we report that oleic acid stimulates the cAMP/protein kinase A pathway and activates the SIRT1-PGC1? transcriptional complex to modulate rates of fatty acid oxidation. In skeletal muscle cells, oleic acid treatment increased intracellular levels of cyclic adenosine monophosphate (cAMP) that turned on protein kinase A activity. This resulted in SIRT1 phosphorylation at Ser-434 and elevation of its catalytic deacetylase activity. A direct SIRT1 substrate is the transcriptional coactivator peroxisome proliferator-activated receptor ? coactivator 1-? (PGC1?), which became deacetylated and hyperactive after oleic acid treatment. Importantly, oleic acid, but not other long chain fatty acids such as palmitate, increased the expression of genes linked to fatty acid oxidation pathway in a SIRT1-PGC1?-dependent mechanism. As a result, oleic acid potently accelerated rates of complete fatty acid oxidation in skeletal muscle cells. These results illustrate how a single long chain fatty acid specifically controls lipid oxidation through a signaling/transcriptional pathway. Pharmacological manipulation of this lipid signaling pathway might provide therapeutic possibilities to treat metabolic diseases associated with lipid dysregulation. PMID:23329830

Lim, Ji-Hong; Gerhart-Hines, Zachary; Dominy, John E.; Lee, Yoonjin; Kim, Sungjin; Tabata, Mitsuhisa; Xiang, Yang K.; Puigserver, Pere

2013-01-01

49

Fatty acid composition, antioxidant and antibacterial activities of Adonis wolgensis L. extract  

PubMed Central

Objectives: The objective of this study was to analyze the fatty acid content, antioxidant, and antibacterial activities of hydro-methanolic extract of Adonis wolgensis L. (A. wolgensis L.) growing wild in north of Iran. Materials and Methods: Oils of A. wolgensis L. was obtained by means of Soxhlet apparatus from leaves and stems. Methyl esters were derived from the oily mixtures by trans-esterification process and were analyzed by GC/FID and GC/MS systems. Phenolic compounds extraction was done with aqueous methanol (90%). This extract was investigated for antioxidant activity using DPPH radical scavenging and reducing power methods and was also tested against a panel of microorganisms. Results: Linolenic acid (45.83%) and oleic acid (47.54%) were the most abundant fatty acids in leaves and stems, respectively. Hydro-methanolic extract with the high amount of total phenolics (9.20 ±0.011 mg GAE per dry matter) was the potent antioxidant in the assays. Results obtained from measurements of MIC for extract, indicated that E. coli, S. aureus, and S. enteritidis were the most sensitive microorganisms tested, but no activity was observed against Gram-positive microorganism (B. subtilis). Conclusion: The results obtained from the present study indicated that the oil of A. wolgensis leaves and stems contained a high source of poly-unsaturated fatty acids (PUFAs). These results also showed that hydro-methanolic extract of this plant contained significant antioxidant and antibacterial activities. PMID:25050298

Mohadjerani, Maryam; Tavakoli, Rahmatollah; Hosseinzadeh, Rahman

2014-01-01

50

Trans Fatty Acids  

NASA Astrophysics Data System (ADS)

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.

Doyle, Ellin

1997-09-01

51

In vitro biological activities and fatty acid profiles of Pistacia terebinthus fruits and Pistacia khinjuk seeds.  

PubMed

This study reports in vitro anticholinesterase, antioxidant and antimicrobial effects of the n-hexane, dichloromethane, ethanol and ethanol-water extracts prepared from Pistacia terebinthus L. fruits and Pistacia khinjuk Stocks seeds as well as their total phenolic and flavonoid contents, and fatty acid compositions. Ethanol and ethanol-water extracts of both species exhibited higher anticholinesterase activity than galanthamine. Among ABTS, DPPH and CUPRAC assays, the highest antioxidant capacity of the extracts was found in the last one. P. terebinthus ethanol extract being rich in flavonoid content showed the best cupric reducing effect. All extracts possessed no antimicrobial activity. The main fatty acid in P. terebinthus fruits (52.52%) and P. khinjuk seeds (59.44%) was found to be oleic acid. Our results indicate that P. terebinthus fruits and P. khinjuk seeds could be a good source of anticholinesterase compounds, and could be phytochemically investigated. PMID:25115646

Hac?bekiro?lu, I??l; Y?lmaz, Pelin Köseo?lu; Ha?imi, Nesrin; K?l?nç, Ersin; Tolan, Veysel; Kolak, Ufuk

2014-08-12

52

Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots.  

PubMed

(R)-Glycerol-monolinoleate 4 and (R)-glycerol-monostearate 5 were isolated from the ethyl acetate extracts of Saururus chinensis roots and (R)- or (S)-fatty acid glycerols 4 and 5 were synthesized for confirming their structures and evaluating their inhibitory activities against Lp-PLA(2). The (R)-4 and (S)-4 exhibited Lp-PLA(2) inhibitory activities with IC(50) values of 45.0 and 52.0 microM, respectively. PMID:15961310

Lee, Woo Song; Kim, Mi Jeong; Beck, Young-Il; Park, Yong-Dae; Jeong, Tae-Sook

2005-08-01

53

Activities of liver mitochondrial and peroxisomal fatty acid oxidation enzymes in rats fed trans fat  

Microsoft Academic Search

The effect oftrans fat on the activities of liver mitochondrial and peroxisomal fatty acid oxidation enzymes was examined in various strains\\u000a of rats. When Wistar and Sprague-Dawley rats were fed for 30 days diets containing either olive oil or partially hydrogenated\\u000a corn oil as a source ofcis-ortrans-octadecenoate, respectively, the activities of various enzymes of mitochondrial and peroxisomal ?-oxidation measured withcis-

Takashi Idea; Midori Watanabe; Michihiro Sugano; Iwahiko Yamamoto

1987-01-01

54

Saturated fatty acid intake can influence increase in plasminogen activator inhibitor-1 in obese adolescents.  

PubMed

The aim of this study was to verify if saturated fatty acid intake adjusted by tertiles can influence metabolic, inflammation, and plasminogen activator inhibitor-1 (PAI-1) in obese adolescents. Body mass, height, body mass index, waist circumference, blood pressure, and body composition of 108 obese adolescents were obtained. Fasting glucose, insulin, PAI-1, and CRP were determined. Insulin resistance was assessed by Homeostasis Model Assessment (HOMA-IR) and insulin sensitivity by Quantitative Insulin Sensitivity Check Index (QUICKI). Dietetic intake was estimated by a 3-day dietary record, and volunteers were divided according to consumption of saturated fatty acids: tertile 1 [Low Saturated Fatty Acid Intake (Low-SFA): ?12.14?g], tertile 2 [Moderate Saturated Fatty Intake (Moderate SFA intake): 12.15-20.48?g], and tertile 3 [High Saturated Fatty Acid Intake (High-SFA Intake); >20.48?g]. Statistical analysis was performed using STATISTICA 7.0 software and the significance level was set at p<0.05. The most important finding in the present study is that Moderate and High-SFA intakes presented significantly higher values of PAI-1 than Low-SFA Intake. PAI-1 was positively associated with saturated fatty intake, waist circumference, mean blood pressure, and HOMA-IR. SFA intake was predictor of PAI-1 independent of body fat, HOMA-IR and total-cholesterol. In addition, PAI-1 was an independent predictor of blood pressure. HOMA-IR and QUICKI presented significantly higher and lower, respectively, in High-SFA compared to Moderate-SFA intake. High-SFA influenced cardiovascular disease risks, since it increased PAI-1 and insulin resistance, and decreased insulin sensibility, leading to vicious cycle among food ingestion, pro-thrombotic state, and cardiovascular risks in obese adolescents. PMID:24619821

Masquio, D C L; de Piano, A; Campos, R M S; Sanches, P L; Corgosinho, F C; Carnier, J; Oyama, L M; do Nascimento, C M P O; de Mello, M T; Tufik, S; Dâmaso, A R

2014-04-01

55

bZIP67 Regulates the Omega-3 Fatty Acid Content of Arabidopsis Seed Oil by Activating FATTY ACID DESATURASE3[W][OPEN  

PubMed Central

Arabidopsis thaliana seed maturation is accompanied by the deposition of storage oil, rich in the essential ?-3 polyunsaturated fatty acid ?-linolenic acid (ALA). The synthesis of ALA is highly responsive to the level of FATTY ACID DESATURASE3 (FAD3) expression, which is strongly upregulated during embryogenesis. By screening mutants in LEAFY COTYLEDON1 (LEC1)–inducible transcription factors using fatty acid profiling, we identified two mutants (lec1-like and bzip67) with a seed lipid phenotype. Both mutants share a substantial reduction in seed ALA content. Using a combination of in vivo and in vitro assays, we show that bZIP67 binds G-boxes in the FAD3 promoter and enhances FAD3 expression but that activation is conditional on bZIP67 association with LEC1-LIKE (L1L) and NUCLEAR FACTOR-YC2 (NF-YC2). Although FUSCA3 and ABSCISIC ACID INSENSITIVE3 are required for L1L and bZIP67 expression, neither protein is necessary for [bZIP67:L1L:NF-YC2] to activate FAD3. We conclude that a transcriptional complex containing L1L, NF-YC2, and bZIP67 is induced by LEC1 during embryogenesis and specifies high levels of ALA production for storage oil by activating FAD3 expression. PMID:23995083

Mendes, Ana; Kelly, Amélie A.; van Erp, Harrie; Shaw, Eve; Powers, Stephen J.; Kurup, Smita; Eastmond, Peter J.

2013-01-01

56

Fatty acids inhibit growth-factor-induced diacylglycerol kinase alpha activation in vascular smooth-muscle cells.  

PubMed Central

We have previously shown that unsaturated fatty acids amplify platelet-derived-growth-factor (PDGF)-induced protein kinase C (PKC) activation in vascular smooth-muscle cells (VSMCs). Diacylglycerol-induced PKC activation is normally terminated by diacylglycerol kinases (DGKs). We thus hypothesized that fatty acids act by inhibiting a DGK. Fractionation of VSMC extracts demonstrated that the DGK alpha isoform was the major DGK activity present. PDGF markedly increased the DGK activity of cultured cells. An inhibitor selective for the DGK alpha isoform, R59949 [3-[2-[4-(bis-(4-fluorophenyl)methylene]piperidin-1-yl)ethyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone], abolished the growth-factor-induced increase in DGK activity, but had little effect on basal activity. PDGF thus selectively activates DGKalpha. Epidermal growth factor and alpha-thrombin stimulated total DGK activity similarly to PDGF. Activation by epidermal growth factor was sensitive to R59949, again suggesting involvement of DGKalpha. However, the alpha-thrombin-induced activity was unaffected by this agent. Unsaturated fatty acids inhibited growth-factor-induced DGKalpha activation, but had no effect on basal activity. Fatty acids also amplified the PDGF-induced increase in cell diacylglycerol content. These results indicate that inhibition of DGKalpha contributes to fatty-acid-induced amplification of PKC activation. Increased levels of fatty acids in diabetes may thus contribute to chronic PKC activation associated with this disorder. PMID:11415460

Du, X; Jiang, Y; Qian, W; Lu, X; Walsh, J P

2001-01-01

57

Fatty acid composition of plasma lipids and erythrocyte membranes during simulated extravehicular activity  

NASA Astrophysics Data System (ADS)

Ten subjects (from 27 to 41 years) have been participated in 32 experiments. They were decompressed from ground level to 40-35 kPa in altitude chamber when breathed 100% oxygen by mask and performed repeated cycles of exercises (3.0 Kcal/min). The intervals between decompressions were 3-5 days. Plasma lipid and erythrocyte membrane fatty acid composition was evaluated in the fasting venous blood before and immediately after hypobaric exposure. There were 7 cases decompression sickness (DCS). Venous gas bubbles (GB) were detected in 27 cases (84.4%). Any significant changes in the fatty acid composition of erythrocyte membranes and plasma didn't practically induce after the first decompression. However, by the beginning of the second decompression the total lipid level in erythrocyte membranes decreased from 54.6 mg% to 40.4 mg% in group with DCS symptoms and from 51.2 mg% to 35.2 mg% (p < 0.05) without DCS symptoms. In group with DCS symptoms a tendency to increased level of saturated fatty acids in erythrocyte membranes (16:0, 18:0), the level of the polyunsaturated linoleic fatty acid (18:2) and arachidonic acid (20:4) tended to be decreased by the beginning of the second decompression. Insignificant changes in blood plasma fatty acid composition was observed in both groups. The obtained biochemical data that indicated the simulated extravehicular activity (EVA) condition is accompanied by the certain changes in the blood lipid metabolism, structural and functional state of erythrocyte membranes, which are reversible. The most pronounced changes are found in subjects with DCS symptoms.

Skedina, M. A.; Katuntsev, V. P.; Buravkova, L. B.; Naidina, V. P.

58

Fatty acid composition of plasma lipids and erythrocyte membranes during simulated extravehicular activity.  

PubMed

Ten subjects (from 27 to 41 years) have been participated in 32 experiments. They were decompressed from ground level to 40-35 kPa in altitude chamber when breathed 100% oxygen by mask and performed repeated cycles of exercises (3.0 Kcal/min). The intervals between decompressions were 3-5 days. Plasma lipid and erythrocyte membrane fatty acid composition was evaluated in the fasting venous blood before and immediately after hypobaric exposure. There were 7 cases decompression sickness (DCS). Venous gas bubbles (GB) were detected in 27 cases (84.4%). Any significant changes in the fatty acid composition of erythrocyte membranes and plasma didn't practically induce after the first decompression. However, by the beginning of the second decompression the total lipid level in erythrocyte membranes decreased from 54.6 mg% to 40.4 mg% in group with DCS symptoms and from 51.2 mg% to 35.2 mg% (p<0.05) without DCS symptoms. In group with DCS symptoms a tendency to increased level of saturated fatty acids in erythrocyte membranes (16:0, 18:0), the level of the polyunsaturated linoleic fatty acid (18:2) and arachidonic acid (20:4) tended to be decreased by the beginning of the second decompression. Insignificant changes in blood plasma fatty acid composition was observed in both groups. The obtained biochemical data that indicated the simulated extravehicular activity (EVA) condition is accompanied by the certain changes in the blood lipid metabolism, structural and functional state of erythrocyte membranes, which are reversible. The most pronounced changes are found in subjects with DCS symptoms. PMID:11541938

Skedina, M A; Katuntsev, V P; Buravkova, L B; Naidina, V P

1998-01-01

59

Mouse serum paraoxonase-1 lactonase activity is specific for medium-chain length fatty acid lactones.  

PubMed

Recent studies suggest that paraoxonase-1 (PON1), complexed with high-density lipoproteins, is the major lactonase in the circulation. Using 5-hydroxy eicosatetraenoate ?-lactone (5-HETEL) as the substrate, we observed lactonase activity in serum from Pon1-/- mice. However, 6-12 carbon fatty acid ?- and ?-lactones were not hydrolyzed in serum from Pon1-/- mice. Serum from both wild-type and Pon1-/- mice contained a lactonase activity towards 5-HETEL and 3-oxo-dodecanoyl-homoserine lactone that was resistant to inactivation by EDTA. This lactonase activity was sensitive to the serine esterase inhibitor phenyl methyl sulfonyl fluoride and co-eluted with carboxylesterase activity by size-exclusion chromatography. Analysis of serum from the Es1e mouse strain, which has a deficiency in the carboxylesterase, ES-1, proved that this activity was due to ES-1. PON1 activity predominated at early time points (30 s), whereas both PON1 and ES-1 contributed equally at later time points (15 min). When both PON1 and ES-1 were inhibited, 5-HETEL was stable in mouse serum. Thus, while long-chain fatty acid lactones are substrates for PON1, they can be hydrolyzed by ES-1 at neutral pH. In contrast, medium-chain length fatty acid lactones are stable in mouse serum in the absence of PON1, suggesting that PON1 plays a specific role in the metabolism of these compounds. PMID:21044894

Connelly, Philip W; Picardo, Clive M; Potter, Philip M; Teiber, John F; Maguire, Graham F; Ng, Dominic S

2011-01-01

60

Do fish oil omega-3 fatty acids enhance antioxidant capacity and mitochondrial fatty acid oxidation in human atrial myocardium via PPAR? activation?  

PubMed

Abstract Studies in experimental models suggest that n-3 polyunsaturated fatty acids (PUFAs) improve metabolic and anti-inflammatory/antioxidant capacity of the heart, although the mechanisms are unclear and translational evidence is lacking. In this study, patients ingested a moderately high dose of n-3 PUFAs (3.4 g/day eicosapentaenoic (EPA) and doxosahexaenoic acid (DHA) ethyl-esters) for a period of 2-3 weeks before having elective cardiac surgery. Blood was obtained before treatment and at the time of surgery, and myocardial tissue from the right atrium was also dissected during surgery. Blood EPA levels increased and myocardial tissue EPA and DHA levels were significantly higher in n-3 PUFA-treated patients compared with untreated, standard-of-care control patients. Interestingly, n-3 PUFA patients had greater nuclear transactivation of peroxisome proliferator-activated receptor-? (PPAR?), fatty acid metabolic gene expression, and enhanced mitochondrial respiration supported by palmitoyl-carnitine in the atrial myocardium, despite no difference in mitochondrial content. Myocardial tissue from n-3 PUFA patients also displayed greater expression and activity of key antioxidant/anti-inflammatory enzymes. These findings lead to our hypothesis that PPAR? activation is a mechanism by which fish oil n-3 PUFAs enhance mitochondrial fatty acid oxidation and antioxidant capacity in human atrial myocardium, and that this preoperative therapeutic regimen may be optimal for mitigating oxidative/inflammatory stress associated with cardiac surgery. PMID:24597798

Anderson, Ethan J; Thayne, Kathleen A; Harris, Mitchel; Shaikh, Saame Raza; Darden, Timothy M; Lark, Daniel S; Williams, John Mark; Chitwood, W Randolph; Kypson, Alan P; Rodriguez, Evelio

2014-09-10

61

Antifungal hydroxy fatty acids produced during sourdough fermentation: microbial and enzymatic pathways, and antifungal activity in bread.  

PubMed

Lactobacilli convert linoleic acid to hydroxy fatty acids; however, this conversion has not been demonstrated in food fermentations and it remains unknown whether hydroxy fatty acids produced by lactobacilli have antifungal activity. This study aimed to determine whether lactobacilli convert linoleic acid to metabolites with antifungal activity and to assess whether this conversion can be employed to delay fungal growth on bread. Aqueous and organic extracts from seven strains of lactobacilli grown in modified De Man Rogosa Sharpe medium or sourdough were assayed for antifungal activity. Lactobacillus hammesii exhibited increased antifungal activity upon the addition of linoleic acid as a substrate. Bioassay-guided fractionation attributed the antifungal activity of L. hammesii to a monohydroxy C(18:1) fatty acid. Comparison of its antifungal activity to those of other hydroxy fatty acids revealed that the monohydroxy fraction from L. hammesii and coriolic (13-hydroxy-9,11-octadecadienoic) acid were the most active, with MICs of 0.1 to 0.7 g liter(-1). Ricinoleic (12-hydroxy-9-octadecenoic) acid was active at a MIC of 2.4 g liter(-1). L. hammesii accumulated the monohydroxy C(18:1) fatty acid in sourdough to a concentration of 0.73 ± 0.03 g liter(-1) (mean ± standard deviation). Generation of hydroxy fatty acids in sourdough also occurred through enzymatic oxidation of linoleic acid to coriolic acid. The use of 20% sourdough fermented with L. hammesii or the use of 0.15% coriolic acid in bread making increased the mold-free shelf life by 2 to 3 days or from 2 to more than 6 days, respectively. In conclusion, L. hammesii converts linoleic acid in sourdough and the resulting monohydroxy octadecenoic acid exerts antifungal activity in bread. PMID:23315734

Black, Brenna A; Zannini, Emanuele; Curtis, Jonathan M; Gänzle, Michael G

2013-03-01

62

Antifungal Hydroxy Fatty Acids Produced during Sourdough Fermentation: Microbial and Enzymatic Pathways, and Antifungal Activity in Bread  

PubMed Central

Lactobacilli convert linoleic acid to hydroxy fatty acids; however, this conversion has not been demonstrated in food fermentations and it remains unknown whether hydroxy fatty acids produced by lactobacilli have antifungal activity. This study aimed to determine whether lactobacilli convert linoleic acid to metabolites with antifungal activity and to assess whether this conversion can be employed to delay fungal growth on bread. Aqueous and organic extracts from seven strains of lactobacilli grown in modified De Man Rogosa Sharpe medium or sourdough were assayed for antifungal activity. Lactobacillus hammesii exhibited increased antifungal activity upon the addition of linoleic acid as a substrate. Bioassay-guided fractionation attributed the antifungal activity of L. hammesii to a monohydroxy C18:1 fatty acid. Comparison of its antifungal activity to those of other hydroxy fatty acids revealed that the monohydroxy fraction from L. hammesii and coriolic (13-hydroxy-9,11-octadecadienoic) acid were the most active, with MICs of 0.1 to 0.7 g liter?1. Ricinoleic (12-hydroxy-9-octadecenoic) acid was active at a MIC of 2.4 g liter?1. L. hammesii accumulated the monohydroxy C18:1 fatty acid in sourdough to a concentration of 0.73 ± 0.03 g liter?1 (mean ± standard deviation). Generation of hydroxy fatty acids in sourdough also occurred through enzymatic oxidation of linoleic acid to coriolic acid. The use of 20% sourdough fermented with L. hammesii or the use of 0.15% coriolic acid in bread making increased the mold-free shelf life by 2 to 3 days or from 2 to more than 6 days, respectively. In conclusion, L. hammesii converts linoleic acid in sourdough and the resulting monohydroxy octadecenoic acid exerts antifungal activity in bread. PMID:23315734

Black, Brenna A.; Zannini, Emanuele; Curtis, Jonathan M.

2013-01-01

63

Activity of Bradykinin B2 Receptor Is Regulated by Long-Chain Polyunsaturated Fatty Acids  

PubMed Central

The molecular and cellular mechanisms by which long-chain polyunsaturated fatty acids (LCPUFA) exert their beneficial effects on cardiovascular health remain obscure. While both LCPUFA and bradykinin (BK) signaling pathway play a role in the cardiovascular system, any direct link between the two is yet to be established. Using picosecond time-resolved fluorescence microscopy and a genetically engineered bradykinin B2 receptor (B2R) sensor (B2K-CC), we detected LCPUFA-induced conformational responses in the B2R similar to those caused by its cognate ligand, BK. The selective B2R antagonist (HOE-140) blocked the eicosapentaenoic acid (EPA, C20?5, n-3) induced conformational response of the B2K-CC. Further analysis suggests that LCPUFA are capable of direct, B2R-dependent activation of extracellular ligand-regulated kinases (ERK). From a wide range of fatty acids studied, varying in chain length, saturation, and position of double bonds, EPA, docosahexaenoic (DHA, C22?6, n-3), docosadienoic (DDA, C22?2, n-6), and dihomo-gamma linoleic (DGLA, C20?3, n-6) fatty acids caused the highest ERK phosphorylation. EPA or DHA dependent ERK phosphorylation was inhibited by the selective B2R antagonist. We show that LCPUFA stimulates downstream signaling by B2R such as B2R-dependent phosphorylation and expression regulation of endothelial nitric-oxide synthase (eNOS). Further analysis indicated that LCPUFA also alters levels of the eNOS transcription factor, kruppel-like factor 2 (KLF2). Moreover we show that EPA increases membrane fluidity on the same time scale as B2R conformational response, suggesting that partitioning of LCPUFA into bilayer is a primary step required for receptor activation. In summary our data show that LCPUFA activate B2R receptor at nanomolar concentrations suggesting a novel molecular mechanism by which fatty acids may affect the cardiovascular system. PMID:23826374

Candelario, Jose; Chachisvilis, Mirianas

2013-01-01

64

Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential  

Microsoft Academic Search

Amongst the diverse and potent biological activities of free fatty acids (FFAs) is the ability to kill or inhibit the growth\\u000a of bacteria. The antibacterial properties of FFAs are used by many organisms to defend against parasitic or pathogenic bacteria.\\u000a Whilst their antibacterial mode of action is still poorly understood, the prime target of FFA action is the cell membrane,

Andrew P. Desbois; Valerie J. Smith

2010-01-01

65

Antibacterial activity of selected fatty acids and essential oils against six meat spoilage organisms  

Microsoft Academic Search

The antibacterial activity of selected fatty acids and essential oils was examined against two gram-negative (Pseudomonas fluorescens and Serratia liquefaciens), and four gram-positive (Brochothrix thermosphacta, Carnobacterium piscicola, Lactobacillus curvatus, and Lactobacillus sake) bacteria involved in meat spoilage. Various amounts of each preservative were added to brain heart infusion or MRS (deMan, Rogosa and Sharpe) agars, and the minimum inhibitory concentration

Blaise Ouattara; Ronald E Simard; Richard A Holley; Gabriel J.-P Piette; André Bégin

1997-01-01

66

UCP2-induced fatty acid synthase promotes NLRP3 inflammasome activation during sepsis.  

PubMed

Cellular lipid metabolism has been linked to immune responses; however, the precise mechanisms by which de novo fatty acid synthesis can regulate inflammatory responses remain unclear. The NLRP3 inflammasome serves as a platform for caspase-1-dependent maturation and secretion of proinflammatory cytokines. Here, we demonstrated that the mitochondrial uncoupling protein-2 (UCP2) regulates NLRP3-mediated caspase-1 activation through the stimulation of lipid synthesis in macrophages. UCP2-deficient mice displayed improved survival in a mouse model of polymicrobial sepsis. Moreover, UCP2 expression was increased in human sepsis. Consistently, UCP2-deficient mice displayed impaired lipid synthesis and decreased production of IL-1? and IL-18 in response to LPS challenge. In macrophages, UCP2 deficiency suppressed NLRP3-mediated caspase-1 activation and NLRP3 expression associated with inhibition of lipid synthesis. In UCP2-deficient macrophages, inhibition of lipid synthesis resulted from the downregulation of fatty acid synthase (FASN), a key regulator of fatty acid synthesis. FASN inhibition by shRNA and treatment with the chemical inhibitors C75 and cerulenin suppressed NLRP3-mediated caspase-1 activation and inhibited NLRP3 and pro-IL-1? gene expression in macrophages. In conclusion, our results suggest that UCP2 regulates the NLRP3 inflammasome by inducing the lipid synthesis pathway in macrophages. These results identify UCP2 as a potential therapeutic target in inflammatory diseases such as sepsis. PMID:25574840

Moon, Jong-Seok; Lee, Seonmin; Park, Mi-Ae; Siempos, Ilias I; Haslip, Maria; Lee, Patty J; Yun, Mijin; Kim, Chun K; Howrylak, Judie; Ryter, Stefan W; Nakahira, Kiichi; Choi, Augustine M K

2015-02-01

67

Insulin Signaling Regulates Fatty Acid Catabolism at the Level of CoA Activation  

PubMed Central

The insulin/IGF signaling pathway is a highly conserved regulator of metabolism in flies and mammals, regulating multiple physiological functions including lipid metabolism. Although insulin signaling is known to regulate the activity of a number of enzymes in metabolic pathways, a comprehensive understanding of how the insulin signaling pathway regulates metabolic pathways is still lacking. Accepted knowledge suggests the key regulated step in triglyceride (TAG) catabolism is the release of fatty acids from TAG via the action of lipases. We show here that an additional, important regulated step is the activation of fatty acids for beta-oxidation via Acyl Co-A synthetases (ACS). We identify pudgy as an ACS that is transcriptionally regulated by direct FOXO action in Drosophila. Increasing or reducing pudgy expression in vivo causes a decrease or increase in organismal TAG levels respectively, indicating that pudgy expression levels are important for proper lipid homeostasis. We show that multiple ACSs are also transcriptionally regulated by insulin signaling in mammalian cells. In sum, we identify fatty acid activation onto CoA as an important, regulated step in triglyceride catabolism, and we identify a mechanistic link through which insulin regulates lipid homeostasis. PMID:22275878

Xu, Xiaojun; Gopalacharyulu, Peddinti; Seppänen-Laakso, Tuulikki; Ruskeepää, Anna-Liisa; Aye, Cho Cho; Carson, Brian P.; Mora, Silvia; Oreši?, Matej; Teleman, Aurelio A.

2012-01-01

68

Hydroxy monounsaturated fatty acids as agonists for peroxisome proliferator-activated receptors.  

PubMed

The physiological and pathological role of oxidized polyunsaturated fatty acids (PUFAs) has been extensively studied, whereas those of hydroxy monounsaturated fatty acids (MUFAs) are not well understood. This study demonstrated that 11-hydroxy-(9Z)-octadecenoic acid ((9Z)-11-HOE), which was isolated from adlay seeds (Coix lacryma-jobi L. var. ma-yuen STAF.), can activate peroxisome proliferator-activated receptor (PPAR)alpha, delta and gamma in luciferase reporter assays more efficiently than (9Z)-octadecenoic acid (oleic acid), and to the same degree as linoleic acid. (9Z)-11-HOE increased the mRNA levels of UCP2 and CD36 in C2C12 myotubes and THP- 1 cells, respectively, and these effects were blocked by the PPARdelta- and gamma-specific antagonists GSK0660 and T0070907, respectively. Evaluation of the structure.activity relationship between hydroxy MUFAs and PPAR activation revealed that (9E)-11-HOE, the geometrical isomer of (9Z)-11-HOE, activated PPARs more potently than (9Z)-11-HOE, and that PPAR activation by hydroxyl MUFAs was not markedly influenced by the position of the hydroxy group or the double bond, although PPARdelta seemed to possess ligand specificity different to that of PPARalpha or gamma . Additionally, the finding that 11-hydroxy octadecanoic acid, the hydrogenated product of (9E)-11- HOE, was also capable of activating PPARs to a similar extent as (9E)-11-HOE indicates that the double bond in hydroxy MUFAs is not essential for PPAR activation. In conclusion, (9Z)-11-HOE derived from alday seeds and hydroxy MUFAs with a chain length of 16 or 18 acted as PPAR agonists. Hydroxylation of MUFAs may change these compounds from silent PPAR ligands to active PPAR agonists. PMID:20460766

Yokoi, Hiroshi; Mizukami, Hajime; Nagatsu, Akito; Tanabe, Hiroki; Inoue, Makoto

2010-01-01

69

Understanding Fatty Acid Metabolism through an Active Learning Approach  

ERIC Educational Resources Information Center

A multi-method active learning approach (MALA) was implemented in the Medical Biochemistry teaching unit of the Biomedical Sciences degree at the University of Aveiro, using problem-based learning as the main learning approach. In this type of learning strategy, students are involved beyond the mere exercise of being taught by listening. Less…

Fardilha, M.; Schrader, M.; da Cruz e Silva, O. A. B.; da Cruz e Silva, E. F.

2010-01-01

70

[The fatty acid composition of Ruta graveolens seed oil and its byological activity].  

PubMed

Using high-performance liquid chromatography methods are qualitatively and quantitatively identified most biological important high fatty acids, contained in Ruta graveolens seed oil grown on the experimental plot of Kutateladze Institute of Pharmakochemistry (Georgia) and compare its biological activity. Their relative concentration is expressed as percentages of the total fatty acid component. The sample contained the range of fatty acids from ?12:0 to ?22:0. The investigation showed different sensitivity of components. In order of elution the list of compound are reported. The oil contained 2,08±0,1 mg% lauric, 2,18±0,1 mg% miristic, 3,98±0,1 mg% palmitic, 30,90±1,2 mg% stearic, 41,92±1,8 mg% oleic, 10,14±0,4 mg% linolic, 6,50±0,3 mg% linolenic, 2,00±0,1 mg% arachinic and 2,10±0,1 mg% begenic acid. The chromatography signals with retention values 7,96 and 14,08 minuts are qualitatively not identified. PMID:24323971

Kikalishvili, B Iu; Zurabishvili, D Z; Turabelidze, D G; Shanidze, L A; Nikola?shvili, M N

2013-11-01

71

TR4 promotes fatty acid synthesis in 3T3-L1 adipocytes by activation of pyruvate carboxylase expression.  

PubMed

We show that testicular orphan nuclear receptor 4 (TR4) increases the expression of pyruvate carboxylase (PC) gene in 3T3-L1 adipocytes by direct binding to a TR4 responsive element in the murine PC promoter. While TR4 overexpression increased PC activity, oxaloacetate (OAA) and glycerol levels with enhanced incorporation of (14)C from (14)C-pyruvate into fatty acids in 3T3-L1 adipocytes, PC knockdown by short interfering RNA (siRNA) or inhibition of PC activity by phenylacetic acid (PAA) abolished TR4-enhanced fatty acid synthesis. Moreover, TR4 microRNA reduced PC expression with decreased fatty acid synthesis in 3T3-L1 adipocytes, suggesting that TR4-mediated enhancement of fatty acid synthesis in adipocytes requires increased expression of PC gene. PMID:25240193

Park, Sung-Soo; Kim, Seung-Jin; Choi, Hojung; Chang, Chawnshang; Kim, Eungseok

2014-11-01

72

Modifications of hepatic drug metabolizing enzyme activities in rats fed baobab seed oil containing cyclopropenoid fatty acids.  

PubMed

The effects on drug metabolizing enzymes of cyclopropenoid fatty acids present in baobab seed oil were evaluated in rats fed either a diet with baobab seed oil (1.27% cyclopropenoid fatty acids in the diet) or a diet with heated baobab seed oil (0.046% cyclopropenoid fatty acids in the diet). Comparison was made with rats fed a mixture of oils that contained no cyclopropenoid fatty acid. Rats fed baobab oil showed retarded growth. In comparison with the other groups, the relative liver weights were markedly increased whereas cytochrome P-450 content and NADPH cytochrome c reductase and NADH cytochrome c reductase activities were decreased. In rats fed the heated baobab oil the relative liver weight was decreased and the cytochrome P-450 level and reductase activities were increased relative to levels in rats fed the unheated oil. Ethoxycoumarin deethylase, ethoxyresorufin deethylase and pentoxyresorufin depentylase activities, expressed on the basis of cytochrome P-450, were greater in the group fed unheated baobab seed oil. Cytosolic glutathione transferase activity was markedly decreased in rats fed fresh baobab seed oil and heating the oil, which reduced the content of cyclopropenoid fatty acids, led to a considerable increase of this activity. UDP-glucuronyl transferase activities were not modified by the type of oil included in the diet. It is possible that the mechanisms of action of cyclopropenoid fatty acids are related to alterations of membrane lipid composition or microsomal proteins. PMID:7759021

Andrianaivo-Rafehivola, A A; Siess, M H; Gaydou, E M

1995-05-01

73

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

PubMed

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. PMID:17852509

Karabulut, Ihsan

2007-12-01

74

Discovery of essential fatty acids.  

PubMed

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

Spector, Arthur A; Kim, Hee-Yong

2015-01-01

75

Fatty Acids and Retinoids Control Lipid Metabolism through Activation of Peroxisome Proliferator-Activated Receptor-Retinoid X Receptor Heterodimers  

Microsoft Academic Search

The nuclear hormone receptors called PPARs (peroxisome proliferator-activated receptors alpha, beta, and gamma) regulate the peroxisomal beta-oxidation of fatty acids by induction of the acyl-CoA oxidase gene that encodes the rate-limiting enzyme of the pathway. Gel retardation and cotransfection assays revealed that PPARalpha heterodimerizes with retinoid X receptor beta (RXRbeta RXR is the receptor for 9-cis-retinoic acid) and that the

Hansjorg Keller; Christine Dreyer; Jeffrey Medin; Abderrahim Mahfoudi; Keiko Ozato; Walter Wahli

1993-01-01

76

An active site mutant of Escherichia coli cyclopropane fatty acid synthase forms new non-natural fatty acids providing insights on the mechanism of the enzymatic reaction.  

PubMed

We have produced and purified an active site mutant of the Escherichia coli cyclopropane fatty acid synthase (CFAS) by replacing the strictly conserved G236 within cyclopropane synthases, by a glutamate residue, which corresponds to E146 of the homologous mycolic acid methyltransferase, Hma, producing hydroxymethyl mycolic acids. The G236E CFAS mutant had less than 1% of the in vitro activity of the wild type enzyme. We expressed the G236E CFAS mutant in an E. coli (DE3) strain in which the chromosomal cfa gene had been deleted. After extraction of phospholipids and conversion into the corresponding fatty acid methyl esters (FAMEs), we observed the formation of cyclopropanated FAMEs suggesting that the mutant retained some of the normal activity in vivo. However, we also observed the formation of new C17 methyl-branched unsaturated FAMEs whose structures were determined using GC/MS and NMR analyses. The double bond was located at different positions 8, 9 or 10, and the methyl group at position 10 or 9. Thus, this new FAMEs are likely arising from a 16:1 acyl chain of a phospholipid that had been transformed by the G236E CFAS mutant in vivo. The reaction catalyzed by this G236E CFAS mutant thus starts by the methylation of the unsaturated acyl chain at position 10 or 9 yielding a carbocation at position 9 or 10 respectively. It follows then two competing steps, a normal cyclopropanation or hydride shift/elimination events giving different combinations of alkenes. This study not only provides further evidence that cyclopropane synthases (CSs) form a carbocationic intermediate but also opens the way to CSs engineering for the synthesis of non-natural fatty acids. PMID:23954860

E, Guangqi; Drujon, Thierry; Correia, Isabelle; Ploux, Olivier; Guianvarc'h, Dominique

2013-12-01

77

Aedes aegypti (Diptera: culicidae) biting deterrence: structure-activity relationship of saturated and unsaturated fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

In this study we systematically evaluated for the first time the biting deterrent effects of a series of saturated and unsaturated fatty acids against Aedes aegypti [yellow fever mosquito (Diptera: Culicidae)] using the K & D bioassay system (Klun et al 2005). The saturated fatty acids (C6:0 to C16...

78

The Role of Fatty Acid Oxidation in the Metabolic Reprograming of Activated?T-Cells  

PubMed Central

Activation represents a significant bioenergetic challenge for T-cells, which must undergo metabolic reprogramming to keep pace with increased energetic demands. This review focuses on the role of fatty acid metabolism, both in vitro and in vivo, following T-cell activation. Based upon previous studies in the literature, as well as accumulating evidence in allogeneic cells, I propose a multi-step model of in vivo metabolic reprogramming. In this model, a primary determinant of metabolic phenotype is the ubiquity and duration of antigen exposure. The implications of this model, as well as the future challenges and opportunities in studying T-cell metabolism, will be discussed. PMID:25566254

Byersdorfer, Craig Alan

2014-01-01

79

Stable isotope liquid chromatography-tandem mass spectrometry assay for fatty acid amide hydrolase activity.  

PubMed

Fatty acid amide hydrolase (FAAH) is the main enzyme responsible for the hydrolysis of the endocannabinoid anandamide (arachidonoyl ethanolamide, AEA) to arachidonic acid (AA) and ethanolamine (EA). Published FAAH activity assays mostly employ radiolabeled anandamide or synthetic fluorogenic substrates. We report a stable isotope liquid chromatography-tandem mass spectrometry (LC-MS/MS) assay for specific, sensitive, and high-throughput capable FAAH activity measurements. The assay uses AEA labeled with deuterium on the EA moiety (d?-AEA) as substrate and measures the specific reaction product tetradeutero-EA (d?-EA) and the internal standard ¹³C?-EA. Selected reaction monitoring of m/z 66?m/z 48 (d?-EA) and m/z 64?m/z 46 (¹³C?-EA) in the positive electrospray ionization mode after liquid chromatographic separation on a HILIC (hydrophilic interaction liquid chromatography) column is performed. The assay was developed and thoroughly validated using recombinant human FAAH (rhFAAH) and then was applied to human blood and dog liver samples. rhFAAH-catalyzed d?-AEA hydrolysis obeyed Michaelis-Menten kinetics (K(M)=12.3 ?M, V(max)=27.6 nmol/min mg). Oleoyl oxazolopyridine (oloxa) was a potent, partial noncompetitive inhibitor of rhFAAH (IC??=24.3 nM). Substrate specificity of other fatty acid ethanolamides decreased with decreasing length, number of double bonds, and lipophilicity of the fatty acid skeleton. In human whole blood, we detected FAAH activity that was inhibited by oloxa. PMID:22146559

Rakers, Christin; Zoerner, Alexander A; Engeli, Stefan; Batkai, Sandor; Jordan, Jens; Tsikas, Dimitrios

2012-02-15

80

Modulation of the Cold-Activated Channel TRPM8 by Lysophospholipids and Polyunsaturated Fatty Acids  

PubMed Central

We investigated the role of phospholipase A2 (PLA2) and the effects of PLA2 products (polyunsaturated fatty acids and lysophospholipids) on the cold-sensitive channel transient receptor potential (melastatin)-8 (TRPM8), heterologously expressed in Chinese hamster ovary cells. TRPM8 responses to cold and the agonist icilin were abolished by inhibitors of the calcium-independent (iPLA2) form of the enzyme, whereas responses to menthol were less sensitive to iPLA2 inhibition. Inhibition of PLA2 similarly abolished the cold responses of the majority of cold-sensitive dorsal root ganglion neurons. The products of PLA2 had opposing effects on TRPM8. Lysophospholipids (LPLs) (lysophosphatidylcholine, lysophosphatidylinositol, and lysophosphatidylserine) altered the thermal sensitivity of TRPM8, raising the temperature threshold toward normal body temperature. Polyunsaturated fatty acids (PUFAs), such as arachidonic acid, inhibited the activation of TRPM8 by cold, icilin, and menthol. The relative potencies of lysophospholipids and PUFAs are such that lysophosphatidylcholine is able to modulate TRPM8 in the presence of an equimolar concentration of arachidonic acid. Positive modulation by LPLs provides a potential physiological mechanism for sensitizing and activating TRPM8 in the absence of temperature variations. PMID:17376995

Andersson, David A.; Nash, Mark; Bevan, Stuart

2009-01-01

81

The role of nitrated fatty acids and peroxisome proliferator-activated receptor gamma in modulating inflammation.  

PubMed

Nitrated fatty acids (NFAs), thought to be produced by nonenzymatic reactions of endogenous nitric oxide (NO) with naturally present unsaturated fatty acids, have recently been identified as one of the largest single pools of biologically active NO derivatives in human plasma. As the biological role of NFAs is unknown, initial in vitro studies have shown them to be potent suppressors of inflammatory responses. The aim of the study was to collect all the literature on NFAs and its interactions with peroxisome proliferator-activated receptor gamma (PPAR-?) and review in detail the anti-inflammatory properties of PPAR-? interceded by NFAs. A literature survey was performed using PubMed and ScienceDirect to gather complete information on NFAs and their interactions with PPAR-?. An exhaustive literature survey revealed that NFAs found in human plasma and urine comprises a class of cell signaling mediators that can activate PPAR-? within its physiological concentration. NFAs exhibit anti-inflammatory and anti-fibrotic effects through PPAR-? activation in various in vitro models tested. Besides its role in inflammation other properties of NFAs such as inhibition of enzymes, inducer of gene expression, etc., were discussed. NFAs are good electrophiles with pleiotropic biological activities. Hence NFAs can be treated as potent drug candidates. PMID:25241247

Narala, Venkata Ramireddy; Subramani, Parasuraman Aiya; Narasimha, Vydyanath R; Shaik, Firdose Begum; Panati, Kalpana

2014-11-01

82

Transcription of the Escherichia coli Fatty Acid Synthesis Operon fabHDG Is Directly Activated by FadR and Inhibited by ppGpp  

PubMed Central

In Escherichia coli, FadR and FabR are transcriptional regulators that control the expression of fatty acid degradation and unsaturated fatty acid synthesis genes, depending on the availability of fatty acids. In this report, we focus on the dual transcriptional regulator FadR. In the absence of fatty acids, FadR represses the transcription of fad genes required for fatty acid degradation. However, FadR is also an activator, stimulating transcription of the products of the fabA and fabB genes responsible for unsaturated fatty acid synthesis. In this study, we show that FadR directly activates another fatty acid synthesis promoter, PfabH, which transcribes the fabHDG operon, indicating that FadR is a global regulator of both fatty acid degradation and fatty acid synthesis. We also demonstrate that ppGpp and its cofactor DksA, known primarily for their role in regulation of the synthesis of the translational machinery, directly inhibit transcription from the fabH promoter. ppGpp also inhibits the fadR promoter, thereby reducing transcription activation of fabH by FadR indirectly. Our study shows that both ppGpp and FadR have direct roles in the control of fatty acid promoters, linking expression in response to both translation activity and fatty acid availability. PMID:23772072

My, Laetitia; Rekoske, Brian; Lemke, Justin J.; Viala, Julie P.; Gourse, Richard L.

2013-01-01

83

Fatty acid signaling in Arabidopsis  

Microsoft Academic Search

.   Many organisms use fatty acid derivatives as biological regulators. In plants, for example, fatty acid-derived signals have\\u000a established roles in the regulation of developmental and defense gene expression. Growing numbers of these compounds, mostly\\u000a derived from fatty acid hydroperoxides, are being characterized. The model plant Arabidopsis thaliana is serving a vital role in the discovery of fatty acid-derived signal

Edward E. Farmer; Hans Weber; Sabine Vollenweider

1998-01-01

84

Modulation of purified murine T cell subset activation by dietary n-3 Polyunsaturated fatty acids  

E-print Network

n-3 Polyunsaturated fatty acids (PUFA) have been shown to reduce inflammation in diseases such as rheumatoid arthritis. The present studies sought to elucidate mechanisms whereby n-3 PUFAs downregulate T cell proliferation and affect CD4 and CD8...

Arrington, Jennifer L

2012-06-07

85

Activated peroxisomal fatty acid metabolism improves cardiac recovery in ischemia-reperfusion.  

PubMed

Depressed oxidation of long chain fatty acids (LCFA) in heart ischemia leads to acute accumulation of LCFA metabolites that impair the functioning of the mitochondria. We hypothesized that reduced activity of carnitine palmitoyltransferase-I (CPT-I) might activate peroxisomal LCFA oxidation and protect mitochondrial function in ischemia and reperfusion. In the present study, despite the long-term threefold reduction in L-carnitine content by 3-(2,2,2-trimethylhydrazinium)-propionate, the uptake and oxidation rates of LCFA in the heart in normoxia were not significantly influenced. The significant increase in PPAR? and PGC1? nuclear content, observed in this study, were followed by increased expression of genes involved in peroxisomal fatty acid oxidation (FAO) which compensated for the limited CPT-I-dependent FA transport into the mitochondria. In ischemia followed by reperfusion, the redirection of LCFA oxidation from mitochondria to peroxisomes protected the mitochondria from the accumulation of LCFA. In turn, the recovery of FAO resulted in significant reduction of myocardial infarct size. In conclusion, the decreased L-carnitine content in the heart preserves its peroxisomal and mitochondrial function after ischemia and improves cardiac recovery during reperfusion. The functional interplay between the decrease in L-carnitine and the PPAR?/PGC1? pathway-induced redirection of FA metabolism protects the mitochondria against LCFA overload and provides a foundation for novel cardioprotective mechanisms. PMID:23525500

Liepinsh, Edgars; Skapare, Elina; Kuka, Janis; Makrecka, Marina; Cirule, Helena; Vavers, Edijs; Sevostjanovs, Eduards; Grinberga, Solveiga; Pugovics, Osvalds; Dambrova, Maija

2013-06-01

86

Type I and type II fatty acid biosynthesis in Eimeria tenella : enoyl reductase activity and structure  

PubMed Central

SUMMARY Apicomplexan parasites of the genus Eimeria are the major causative agent of avian coccidiosis, leading to high economic losses in the poultry industry. Recent results show that Eimeria tenella harbours an apicoplast organelle, and that a key biosynthetic enzyme, enoyl reductase, is located in this organelle. In related parasites, enoyl reductase is one component of a type II fatty acid synthase (FAS) and has proven to be an attractive target for antimicrobial compounds. We cloned and expressed the mature form of E. tenella enoyl reductase (EtENR) for biochemical and structural studies. Recombinant EtENR exhibits NADH-dependent enoyl reductase activity and is inhibited by triclosan with an IC50 value of 60 nM. The crystal structure of EtENR reveals overall similarity with other ENR enzymes; however, the active site of EtENR is unoccupied, a state rarely observed in other ENR structures. Furthermore, the position of the central beta-sheet appears to block NADH binding and would require significant movement to allow NADH binding, a feature not previously seen in the ENR family. We analysed the E. tenella genomic database for orthologues of well-characterized bacterial and apicomplexan FAS enzymes and identified 6 additional genes, suggesting that E. tenella contains a type II FAS capable of synthesizing saturated, but not unsaturated, fatty acids. Interestingly, we also identified sequences that appear to encode multifunctional type I FAS enzymes, a feature also observed in Toxoplasma gondii, highlighting the similarity between these apicomplexan parasites. PMID:17697396

Lu, J. Z.; Muench, S. P.; Allary, M.; Campbell, S.; Roberts, C. W.; Mui, E.; McLeod, R. L.; Rice, D. W.; Prigge, S. T.

2009-01-01

87

Gas chromatography of fatty acids.  

PubMed

Lipids in foods contain a wide variety of fatty acids differing in chain length, degree of unsaturation, position and configuration of double bonds and the presence of special functional groups. Modern capillary gas chromatography offers excellent separation of fatty acids. Fused-silica capillary columns with stationary phases of medium polarity and non-polar methylsilicone stationary phases successfully separate most of the natural fatty acids. Special applications, such as the separation of complex cis-trans fatty acid mixtures and cyclic fatty acids, required particular chromatographic conditions, including the use of very long capillary columns or more polar stationary phases. The derivatization methods for the preparation of fatty acid esters also need to be optimized to obtain accurate quantitative results. This paper reviews the derivatization techniques, capillary columns and stationary phases commonly used in the gas chromatography of fatty acids in food. PMID:1494015

Shantha, N C; Napolitano, G E

1992-10-30

88

Activation of type 2 cannabinoid receptors (CB2R) promotes fatty acid oxidation through the SIRT1/PGC-1? pathway.  

PubMed

Abnormal fatty acid oxidation has been associated with obesity and type 2 diabetes. At the transcriptional level, peroxisome proliferator-activated receptor-gamma coactivator 1? (PGC-1?) has been reported to strongly increase the ability of hormone nuclear receptors PPAR? and ERR? to drive transcription of fatty acid oxidation enzymes. In this study, we report that a specific agonist of the type 2 cannabinoid receptor (CB2R) can lead to fatty acid oxidation through the PGC-1? pathway. We have found that CB2R is expressed in differentiated C2C12 myotubes, and that use of the specific agonist trans-caryophyllene (TC) stimulates sirtuin 1 (SIRT1) deacetylase activity by increasing the phosphorylation of cAMP response element-binding protein (CREB), thus leading to increased levels of PGC-1? deacetylation. This use of TC treatment increases the expression of genes linked to the fatty acid oxidation pathway in a SIRT1/PGC-1?-dependent mechanism and also drastically accelerates the rate of complete fatty acid oxidation in C2C12 myotubes, neither of which occur when CB2R mRNA is knocked down using siRNA. These results reveal that activation of CB2R by a selective agonist promotes lipid oxidation through a signaling/transcriptional pathway. Our findings imply that pharmacological manipulation of CB2R may provide therapeutic possibilities to treat metabolic diseases associated with lipid dysregulation. PMID:23747418

Zheng, Xuqin; Sun, Tao; Wang, Xiaodong

2013-07-01

89

Muscle cells challenged with saturated fatty acids mount an autonomous inflammatory response that activates macrophages.  

PubMed

Obesity is associated with chronic low-grade inflammation. Within adipose tissue of mice fed a high fat diet, resident and infiltrating macrophages assume a pro-inflammatory phenotype characterized by the production of cytokines which in turn impact on the surrounding tissue. However, inflammation is not restricted to adipose tissue and high fat-feeding is responsible for a significant increase in pro-inflammatory cytokine expression in muscle. Although skeletal muscle is the major disposer of dietary glucose and a major determinant of glycemia, the origin and consequence of muscle inflammation in the development of insulin resistance are poorly understood.We used a cell culture approach to investigate the vectorial crosstalk between muscle cells and macrophages upon exposure to physiological, low levels of saturated and unsaturated fatty acids. Inflammatory pathway activation and cytokine expression were analyzed in L6 muscle cells expressing myc-tagged GLUT4 (L6GLUT4myc) exposed to 0.2 mM palmitate or palmitoleate. Conditioned media thereof, free of fatty acids, were then tested for their ability to activate RAW264.7 macrophages.Palmitate -but not palmitoleate- induced IL-6, TNF? and CCL2 expression in muscle cells, through activation of the NF-?B pathway. Palmitate (0.2 mM) alone did not induce insulin resistance in muscle cells, yet conditioned media from palmitate-challenged muscle cells selectively activated macrophages towards a pro-inflammatory phenotype.These results demonstrate that low concentrations of palmitate activate autonomous inflammation in muscle cells to release factors that turn macrophages pro-inflammatory. We hypothesize that saturated fat-induced, low-grade muscle cell inflammation may trigger resident skeletal muscle macrophage polarization, possibly contributing to insulin resistance in vivo. PMID:23078640

Pillon, Nicolas J; Arane, Karen; Bilan, Philip J; Chiu, Tim T; Klip, Amira

2012-01-01

90

SFH2 regulates fatty acid synthase activity in the yeast Saccharomyces cerevisiae and is critical to prevent saturated fatty acid accumulation in response to haem and oleic acid depletion.  

PubMed

The yeast Saccharomyces cerevisiae is a facultative anaerobic organism. Under anaerobiosis, sustained growth relies on the presence of exogenously supplied unsaturated fatty acids and ergosterol that yeast is unable to synthesize in the absence of oxygen or upon haem depletion. In the absence of exogenous supplementation with unsaturated fatty acid, a net accumulation of SFA (saturated fatty acid) is observed that induces significant modification of phospholipid profile [Ferreira, Régnacq, Alimardani, Moreau-Vauzelle and Bergès (2004) Biochem. J. 378, 899-908]. In the present paper, we focus on the role of SFH2/CSR1, a hypoxic gene related to SEC14 and its involvement in lipid metabolism upon haem depletion in the absence of oleic acid supplementation. We observed that inactivation of SFH2 results in enhanced accumulation of SFA and phospholipid metabolism alterations. It results in premature growth arrest and leads to an exacerbated sensitivity to exogenous SFA. This phenotype is suppressed in the presence of exogenous oleic acid, or by a controlled expression of FAS1, one of the two genes encoding FAS. We present several lines of evidence to suggest that Sfh2p and oleic acid regulate SFA synthase in yeast at different levels: whereas oleic acid acts on FAS2 at the transcriptional level, we show that Sfh2p inhibits fatty acid synthase activity in response to haem depletion. PMID:17803462

Desfougères, Thomas; Ferreira, Thierry; Bergès, Thierry; Régnacq, Matthieu

2008-01-01

91

Inflammasome-mediated secretion of IL-1? in human monocytes through TLR2 activation; Modulation by dietary fatty acids  

PubMed Central

Many studies have shown that TLR4 and TLR2 deficient mice are protected from high fat diet-induced inflammation and insulin resistance, suggesting that saturated fatty acids derived from the high fat diet activate TLR-mediated proinflammatory signaling pathways and induce insulin resistance. However, evidence that palmitic acid, the major dietary saturated fatty acid, can directly activate TLR has not been demonstrated. Here we present multiple lines of evidence showing that palmitic acid directly activates TLR2, a major TLR expressed on human monocytes, by inducing heterodimerization with TLR1 in a NADPH oxidase-dependent manner. Dimerization of TLR2 with TLR1 was inhibited by the n-3 fatty acid docosahexaenoic acid. Activation of TLR2 by palmitic acid leads to expression of pro-IL-1? that is cleaved by caspase-1, which is constitutively present in monocytes, to release mature IL-1?. Our results reveal mechanistic insight about how palmitic acid activates TLR2, upregulates NALP3 expression, and induces inflammasome-mediated-IL-1? production in human monocytes which can trigger enhanced inflammation in peripheral tissues, and suggest that these processes are dynamically modulated by the types of dietary fat we consume. PMID:24043885

Snodgrass, Ryan G.; Huang, Shurong; Choi, Il-Whan; Rutledge, John C.; Hwang, Daniel H.

2013-01-01

92

Isolation and identification of C-19 fatty acids with anti-tumor activity from the spores of Ganoderma lucidum (reishi mushroom).  

PubMed

We previously showed that ethanolic extracts of spores of Ganoderma lucidum inhibit tumor cell proliferation and induce apoptosis of HL-60 cells. The active constituents appeared to be long-chain fatty acids, particularly carbon-19 (C-19) fatty acids which have not been reported in spores of Ganoderma lucidum. In the present study, two of these C-19 fatty acids which are key compounds in the activities, were identified as their 2-naphthyl ester derivatives after esterification of a mixture of fatty acids obtained from the spores. The active compounds were determines as nonadecanoic acid and cis-9-nonadecenoic acid. The location of the double bond of cis-9-nonadecenoic acid was demonstrated by GC-MS analysis, based on the fragmentation pattern of the adduct prepared from the fatty acid and dimethyl disulfide. PMID:22230194

Gao, Pei; Hirano, Tomoya; Chen, Zhiqing; Yasuhara, Tadashi; Nakata, Yoshihiro; Sugimoto, Akiko

2012-04-01

93

Fish oil at low dietary levels enhances physiological activity of sesamin to increase hepatic fatty acid oxidation in rats.  

PubMed

We previously demonstrated that a diet containing fish oil at a level of 80 g/kg strongly stimulated the physiological activity of a sesame sesamin preparation containing sesamin and episesamin at equal amounts to increase hepatic fatty acid oxidation. This study was conducted to clarify whether fish oil at lower dietary levels enhances the physiological activity of sesamin to increase hepatic fatty acid oxidation. Rats were fed experimental diets supplemented with 0 or 2 g sesamin/kg, and containing 0, 15 or 30 g fish oil/kg for 15 days. Among rats fed sesamin-free diets, diets containing 15 and 30 g fish oil/kg slightly increased the activity of enzymes involved in hepatic fatty acid oxidation. Sesamin increased these values irrespective of the presence or absence of fish oil in diets; however, the extent of the increase of many parameters was much greater in rats given fish oil-containing diets than in those fed a fish oil-free diet. Diets simultaneously containing sesamin and fish oil increased the gene expression of various peroxisomal fatty acid oxidation enzymes in a synergistic manner; but they were ineffective in causing a synergistic increase in mRNA levels of mitochondrial fatty acid oxidation enzymes. The extent of the synergistic increase in the activity of hepatic fatty acid oxidation enzymes and mRNA levels of the peroxisomal enzymes was indistinguishable between diets containing 15 and 30 g fish oil/kg and appeared comparable to that observed previously with a diet containing 80 g fish oil/kg. PMID:23170054

Ide, Takashi

2012-11-01

94

Regulation of AMPK Activation by CD36 Links Fatty Acid Uptake to ?-Oxidation.  

PubMed

Increases in muscle energy needs activate AMPK and induce sarcolemmal recruitment of the fatty acid (FA) translocase CD36. The resulting rises in FA uptake and FA oxidation are tightly correlated, suggesting coordinated regulation. We explored the possibility that membrane CD36 signaling might influence AMPK activation. We show, using several cell types, including myocytes, that CD36 expression suppresses AMPK, keeping it quiescent, while it mediates AMPK activation by FA. These dual effects reflect the presence of CD36 in a protein complex with the AMPK kinase LKB1 (liver kinase B1) and the src kinase Fyn. This complex promotes Fyn phosphorylation of LKB1 and its nuclear sequestration, hindering LKB1 activation of AMPK. FA interaction with CD36 dissociates Fyn from the protein complex, allowing LKB1 to remain cytosolic and activate AMPK. Consistent with this, CD36(-/-) mice have constitutively active muscle and heart AMPK and enhanced FA oxidation of endogenous triglyceride stores. The molecular mechanism described, whereby CD36 suppresses AMPK, with FA binding to CD36 releasing this suppression, couples AMPK activation to FA availability and would be important for the maintenance of cellular FA homeostasis. Its dysfunction might contribute to the reported association of CD36 variants with metabolic complications of obesity in humans. PMID:25157091

Samovski, Dmitri; Sun, Jingyu; Pietka, Terri; Gross, Richard W; Eckel, Robert H; Su, Xiong; Stahl, Philip D; Abumrad, Nada A

2015-02-01

95

Effects of unsaturated fatty acids on calcium-activated potassium current in gastric myocytes of guinea pigs  

PubMed Central

AIM: To investigate the effects of exogenous unsaturated fatty acids on calcium-activated potassium current [IK(Ca)] in gastric antral circular myocytes of guinea pigs. METHODS: Gastric myocytes were isolated by collagenase from the antral circular layer of guinea pig stomach. The whole-cell patch clamp technique was used to record IK(Ca) in the isolated single smooth muscle cells with or without different concentrations of arachidonic acid (AA), linoleic acid (LA), and oleic acid (OA). RESULTS: AA at concentrations of 2,5 and 10 ?mol/L markedly increased IK(Ca) in a dose-dependent manner. LA at concentrations of 5, 10 and 20 ?mol/L also enhanced IK(Ca) in a dose-dependent manner. The increasing potency of AA, LA, and oleic acid (OA) on IK(Ca) at the same concentration (10 ?mol/L) was in the order of AA>LA>OA. AA (10 ?mol/L)-induced increase of IK(Ca) was not blocked by H-7 (10 ?mol/L), an inhibitor of protein kinase C (PKC), or indomethacin (10 ?mol/L), an inhibitor of the cyclooxygenase pathway, and 17-octadecynoic acid (10 ?mol/L), an inhibitor of the cytochrome P450 pathway, but weakened by nordihydroguaiaretic acid (10 ?mol/L), an inhibitor of the lipoxygenase pathway. CONCLUSION: Unsaturated fatty acids markedly increase IK(Ca), and the enhancing potencies are related to the number of double bonds in the fatty acid chain. The lipoxygenase pathway of unsaturated fatty acid metabolism is involved in the unsaturated fatty acid-induced increase of IK(Ca) in gastric antral circular myocytes of guinea pigs. PMID:15655819

Zheng, Hai-Feng; Li, Xiang-Lan; Jin, Zheng-Yuan; Sun, Jia-Bin; Li, Zai-Liu; Xu, Wen-Xie

2005-01-01

96

Fatty acid composition of common barbel (Barbus barbus) roe and evaluation of its haemolytic and cytotoxic activities.  

PubMed

Eggs of the common barbel (Barbus barbus) cause intoxication in humans after ingestion. In this work, the chemical composition of the haemolytically active fraction from methanolic barbel roe extract was analyzed. Compounds showing haemolytic activity and cytotoxicity towards normal and transformed cell lines were isolated and identified as polyunsaturated fatty acids, using online liquid chromatography-electrospray ionization mass spectrometry through tandem fragmentation experiments (HPLC-MS/MS). Arachidonic acid (C20:4), docosahexaenoic acid (C22:6) and eicosapentaenoic acid (C20:5) proved to be the three most abundant members of a complex series of free fatty acids ranging from C14:0 to C24:5. PMID:21510968

Mancini, Ines; Defant, Andrea; Mesari?, Tina; Poto?nik, Franc; Batista, Urška; Guella, Graziano; Turk, Tom; Sep?i?, Kristina

2011-06-01

97

The combined effects on neuronal activation and blood–brain barrier permeability of time and n-3 polyunsaturated fatty acids in mice, as measured in vivo using MEMRI  

Microsoft Academic Search

N-3 polyunsaturated fatty acids (n-3 PUFA) are known to have cardiovascular and neuroprotective properties in both humans and rodents. Here, we use manganese-enhanced magnetic resonance imaging (MEMRI) to compare the effects of these polyunsaturated fatty acids on the combined effects of neuronal activity and integrity of blood–brain barrier integrity with saturated fatty acids from buttermilk. C57BL\\/6 mice (4 weeks old)

Yu-Ting Kuo; Po-Wah So; James R. Parkinson; Wei Sheng Yu; Mohammad Hankir; Amy H. Herlihy; Anthony P. Goldstone; Gary S. Frost; Clive Wasserfall; Jimmy D. Bell

2010-01-01

98

Omega-3 Free Fatty Acids Suppress Macrophage Inflammasome Activation by Inhibiting NF-?B Activation and Enhancing Autophagy  

PubMed Central

The omega-3 (?3) fatty acid docosahexaenoic acid (DHA) can suppress inflammation, specifically IL-1? production through poorly understood molecular mechanisms. Here, we show that DHA reduces macrophage IL-1? production by limiting inflammasome activation. Exposure to DHA reduced IL-1? production by ligands that stimulate the NLRP3, AIM2, and NAIP5/NLRC4 inflammasomes. The inhibition required Free Fatty Acid Receptor (FFAR) 4 (also known as GPR120), a G-protein coupled receptor (GPR) known to bind DHA. The exposure of cells to DHA recruited the adapter protein ?-arrestin1/2 to FFAR4, but not to a related lipid receptor. DHA treatment reduced the initial inflammasome priming step by suppressing the nuclear translocation of NF-?B. DHA also reduced IL-1? levels by enhancing autophagy in the cells. As a consequence macrophages derived from mice lacking the essential autophagy protein ATG7 were partially resistant to suppressive effects of DHA. Thus, DHA suppresses inflammasome activation by two distinct mechanisms, inhibiting the initial priming step and by augmenting autophagy, which limits inflammasome activity. PMID:24911523

Williams-Bey, Yolanda; Boularan, Cedric; Vural, Ali; Huang, Ning-Na; Hwang, Il-Young; Shan-Shi, Chong; Kehrl, John H.

2014-01-01

99

A FAD2 homologue from Lesquerella lindheimeri has predominantly fatty acid hydroxylase activity  

Microsoft Academic Search

A genomic sequence encoding a polypeptide with 91% sequence identity to the Lesquerella fendleri bifunctional oleate 12-hydroxylase:desaturase was amplified by PCR from Lesquerella lindheimeri. Expression of the gene in the yeast Saccharomyces cerevisiae resulted in the synthesis of ricinoleic acid and very low levels of di-unsaturated fatty acids. Comparison of the amino acid sequences of the L. lindheimeri and castor

Melanie Dauk; Patricia Lam; Ljerka Kunst; Mark A. Smith

2007-01-01

100

LXR-mediated activation of macrophage stearoyl-CoA desaturase generates unsaturated fatty acids that destabilize ABCA1  

Microsoft Academic Search

Abnormal HDL metabolism among patients with diabetes and insulin resistance may contribute to their in- creased risk of atherosclerosis. ATP binding cassette trans- porter A1 (ABCA1) mediates the transport of cholesterol and phospholipids from cells to HDL apolipoproteins and thus modulates HDL levels and atherogenesis. Because fatty acids are increased in diabetes, we examined their ef- fects on ABCA1 activity

Yutong Wang; Buran Kurdi-Haidar; John F. Oram

2004-01-01

101

Fatty Acid Amide Hydrolase (FAAH) Inhibition Enhances Memory Acquisition through Activation of PPAR-alpha Nuclear Receptors  

ERIC Educational Resources Information Center

Inhibitors of fatty acid amide hydrolase (FAAH) increase endogenous levels of anandamide (a cannabinoid CB[subscript 1]-receptor ligand) and oleoylethanolamide and palmitoylethanolamide (OEA and PEA, ligands for alpha-type peroxisome proliferator-activated nuclear receptors, PPAR-alpha) when and where they are naturally released in the brain.…

Mazzola, Carmen; Medalie, Julie; Scherma, Maria; Panlilio, Leigh V.; Solinas, Marcello; Tanda, Gianluigi; Drago, Filippo; Cadet, Jean Lud; Goldberg, Steven R.; Yasar, Sevil

2009-01-01

102

FATTY ACIDS MODULATE TOLL-LIKE RECEPTOR 4 ACTIVATION THROUGH REGULATION OF RECEPTOR DIMERIZATION AND RECRUITMENT INTO LIPID RAFTS  

Technology Transfer Automated Retrieval System (TEKTRAN)

The saturated fatty acids acylated on Lipid A of lipopolysaccharide (LPS) or bacterial lipoproteins play critical roles in ligand recognition and receptor activation for Toll-like Receptor 4 (TLR4) and TLR2. The results from our previous studies (J Biol Chem 2003, 2004) demonstrated that saturated ...

103

Activation of type 2 cannabinoid receptors (CB2R) promotes fatty acid oxidation through the SIRT1/PGC-1? pathway  

SciTech Connect

Highlights: •TC, a CB2R specific agonist, stimulates SIRT1 activity by PKA/CREB pathway. •TC promotes PGC-1? transcriptional activity by increasing its deacetylation. •TC increases the expression of genes linked to FAO and promotes the rate of FAO. •The effects of TC in FAO are dependent on CB2R. •Suggesting CB2R as a target to treat diseases with lipid dysregulation. -- Abstract: Abnormal fatty acid oxidation has been associated with obesity and type 2 diabetes. At the transcriptional level, peroxisome proliferator-activated receptor-gamma coactivator 1? (PGC-1?) has been reported to strongly increase the ability of hormone nuclear receptors PPAR? and ERR? to drive transcription of fatty acid oxidation enzymes. In this study, we report that a specific agonist of the type 2 cannabinoid receptor (CB2R) can lead to fatty acid oxidation through the PGC-1? pathway. We have found that CB2R is expressed in differentiated C2C12 myotubes, and that use of the specific agonist trans-caryophyllene (TC) stimulates sirtuin 1 (SIRT1) deacetylase activity by increasing the phosphorylation of cAMP response element-binding protein (CREB), thus leading to increased levels of PGC-1? deacetylation. This use of TC treatment increases the expression of genes linked to the fatty acid oxidation pathway in a SIRT1/PGC-1?-dependent mechanism and also drastically accelerates the rate of complete fatty acid oxidation in C2C12 myotubes, neither of which occur when CB2R mRNA is knocked down using siRNA. These results reveal that activation of CB2R by a selective agonist promotes lipid oxidation through a signaling/transcriptional pathway. Our findings imply that pharmacological manipulation of CB2R may provide therapeutic possibilities to treat metabolic diseases associated with lipid dysregulation.

Zheng, Xuqin [Department of Endocrinology, First Affiliated Hospital, Nanjing Medical University, Nanjing, Jiangsu Province 210029 (China)] [Department of Endocrinology, First Affiliated Hospital, Nanjing Medical University, Nanjing, Jiangsu Province 210029 (China); Sun, Tao [Department of Neurology, Jinling Hospital, Nanjing University School of Medicine, Nanjing, Jiangsu Province 210002 (China)] [Department of Neurology, Jinling Hospital, Nanjing University School of Medicine, Nanjing, Jiangsu Province 210002 (China); Wang, Xiaodong, E-mail: xdwang666@hotmail.com [Department of Endocrinology, First Affiliated Hospital, Nanjing Medical University, Nanjing, Jiangsu Province 210029 (China)] [Department of Endocrinology, First Affiliated Hospital, Nanjing Medical University, Nanjing, Jiangsu Province 210029 (China)

2013-07-05

104

?-6 Polyunsaturated fatty acids extend life span through the activation of autophagy  

PubMed Central

Adaptation to nutrient scarcity depends on the activation of metabolic programs to efficiently use internal reserves of energy. Activation of these programs in abundant food regimens can extend life span. However, the common molecular and metabolic changes that promote adaptation to nutritional stress and extend life span are mostly unknown. Here we present a response to fasting, enrichment of ?-6 polyunsaturated fatty acids (PUFAs), which promotes starvation resistance and extends Caenorhabditis elegans life span. Upon fasting, C. elegans induces the expression of a lipase, which in turn leads to an enrichment of ?-6 PUFAs. Supplementing C. elegans culture media with these ?-6 PUFAs increases their resistance to starvation and extends their life span in conditions of food abundance. Supplementation of C. elegans or human epithelial cells with these ?-6 PUFAs activates autophagy, a cell recycling mechanism that promotes starvation survival and slows aging. Inactivation of C. elegans autophagy components reverses the increase in life span conferred by supplementing the C. elegans diet with these fasting-enriched ?-6 PUFAs. We propose that the salubrious effects of dietary supplementation with ?-3/6 PUFAs (fish oils) that have emerged from epidemiological studies in humans may be due to a similar activation of autophagic programs. PMID:23392608

O'Rourke, Eyleen J.; Kuballa, Petric; Xavier, Ramnik; Ruvkun, Gary

2013-01-01

105

Reduction of dietary saturated fatty acids correlates with increased plasma lecithin cholesterol acyltransferase activity in humans  

Microsoft Academic Search

Objective: Increased HDL-cholesterol (HDL-C) concentrations have been associated with lower coronary heart disease risk. On the other hand, dietary fats are known to influence the fatty acid profile of plasma lipids, including phospholipids that are substrates of lecithin cholesterol acyltransferase (LCAT), an important enzyme in HDL metabolism. The purpose of this study was to examine the association between the saturated

A M Bérard; H Dabadie; A Palos-Pinto; M-F Dumon; M Darmon

2004-01-01

106

Total dietary fat and fatty acid content modifies plasma phospholipid fatty acids, desaturase activity indices, and urinary prostaglandin E in women  

Technology Transfer Automated Retrieval System (TEKTRAN)

Compared to diets high in fat, low fat diets are associated with reduced risk of cardiovascular disease. We hypothesized that a low fat (LF; 20% fat) and a low fat high omega-3 (n-3) fatty acid diet (LFn3; 23% fat with 3% as ALA, EPA and DHA) would enhance n-3 composition of PLFA and reduce urinary ...

107

Characterisation of fatty acid, carotenoid, tocopherol/tocotrienol compositions and antioxidant activities in seeds of three Chenopodium quinoa Willd. genotypes.  

PubMed

Composition of fatty acids, tocopherols, tocotrienols, and carotenoids, and their contribution to antioxidant activities were investigated in seeds of three coloured quinoa cultivars (white, red and black). The major components and individual compounds were significantly different, and their concentrations were higher in darker seeds (p<0.05). The oil yield was 6.58-7.17% which contained predominantly unsaturated fatty acids (89.42%). The ratio of omega-6/omega-3 fatty acid was ca. 6/1. The total tocopherol content ranged from 37.49 to 59.82?g/g and mainly consisted of ?-tocopherol. Trace amount of ?- and ?-tocotrienols was also found. Black quinoa had the highest vitamin E followed by red and white quinoas. Carotenoids, mainly trans-lutein (84.7-85.6%) and zeaxanthin were confirmed for the first time in quinoa seeds, and the concentration was also the highest in black seeds. The antioxidant activities of lipophilic extracts were positively correlated with polyunsaturated fatty acids, total carotenoids and total tocopherols. PMID:25529712

Tang, Yao; Li, Xihong; Chen, Peter X; Zhang, Bing; Hernandez, Marta; Zhang, Hua; Marcone, Massimo F; Liu, Ronghua; Tsao, Rong

2015-05-01

108

Effect of the maturation process on the phenolic fractions, fatty acids, and antioxidant activity of the Chétoui olive fruit cultivar.  

PubMed

Maturity is one of the most important factors associated with the quality evaluation of fruit and vegetables. This work aims to investigate the effect of the maturation process of the olive fruit on the phenolic fraction and fatty acid of irrigated Chétoui cultivar. The phenolic composition was studied by using reverse-phase high-performance liquid chromatography followed by LC-MS and GC-MS analyses and fatty acids by GC. Oleuropein was the major phenolic compound at all stages of ripeness. Unexpectedly, both phenolic compounds hydroxytyrosol and oleuropein exhibited the same trends during maturation. Indeed, the oleuropein levels decreased during the ripening process and were not inversely correlated with the concentrations of hydroxytyrosol. The antioxidant capacity of olive extracts was evaluated by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl and the beta-carotene linoleate model system. The IC 50 and AAC values of the olive extracts decreased from 3.68 to 1.61 microg/mL and from 645 to 431, respectively. There was a correlation between the antioxidant activity and the oleuropein concentration. The fatty acid composition was quantified in olive fruit during maturation and showed that fatty acids were characterized by the highest level of oleic acid, which reached 65.2%. PMID:18257524

Damak, Nahla; Bouaziz, Mohamed; Ayadi, Mohamed; Sayadi, Sami; Damak, Mohamed

2008-03-12

109

Marked reutilization of free fatty acids during activated lipolysis in human skeletal muscle.  

PubMed

Release of glycerol and free fatty acids (FFA) was investigated in human skeletal muscle strips. In the basal state, glycerol and FFA were released at almost equimolar rates (0.3 nmol/ng tissue.90 min). A nonselective beta-adrenoceptor agonist, isoprenaline, caused a concentration-dependent stimulation of glycerol release, whereas FFA release was unaffected. Basal and isoprenaline-induced glycerol release correlated positively with the age of the donors (r = 0.5, P < 0.005) but not with their body mass index (P > or = 0.4). Biochemical experiments with hormone-sensitive lipase (HSL) showed that most enzyme activity was both in the cytosol and mitochondrial fraction and that it constituted the common long and active form of the protein. Electron microscopy studies in rat skeletal muscle using labeled highly specific HSL antibodies verified the cytosolic location of HSL and, furthermore, indicated an accumulation of HSL-adjoining mitochondria. These results suggest that FFA produced in myocytes during catecholamine-induced lipolysis are retained by the muscle and, therefore by inference, reused. It is conceivable that efficient hydrolysis of acylglycerol by HSL located in the cytosol as well as near the mitochondria may facilitate mitochondrial FFA oxidation. In addition, muscle lipolysis activity increases during aging and may be independent of total body fat. PMID:15562022

Enoksson, Staffan; Hagström-Toft, Eva; Nordahl, Joakim; Hultenby, Kjell; Pettersson, Nils; Isaksson, Bengt; Permert, Johan; Wibom, Rolf; Holm, Cecilia; Bolinder, Jan; Arner, Peter

2005-02-01

110

Fatty acid biosynthesis revisited: structure elucidation and metabolic engineering.  

PubMed

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

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

2015-01-01

111

Mutations in the fatty acid elongation 1 gene are associated with a loss of ?-ketoacyl-CoA synthase activity in low erucic acid rapeseed  

Microsoft Academic Search

Low erucic acid rapeseed (LEAR) is characterised by a near absence of very long chain fatty acids in the seed oil which has been correlated with a lack of acyl-CoA elongation activity. Here we show that the absence of acyl-CoA and ATP-dependent elongation activities in microsomes isolated from LEAR embryos is associated with an absence of ?-ketoacyl-CoA synthase activity encoded

T. J Roscoe; R Lessire; J Puyaubert; M Renard; M Delseny

2001-01-01

112

An Ethanol Extract of Artemisia iwayomogi Activates PPAR? Leading to Activation of Fatty Acid Oxidation in Skeletal Muscle  

PubMed Central

Although Artemisia iwayomogi (AI) has been shown to improve the lipid metabolism, its mode of action is poorly understood. In this study, a 95% ethanol extract of AI (95EEAI) was identified as a potent ligand of peroxisome proliferator-activated receptor? (PPAR?) using ligand binding analysis and cell-based reporter assay. In cultured primary human skeletal muscle cells, treatment of 95EEAI increased expression of two important PPAR?-regulated genes, carnitine palmitoyl-transferase-1 (CPT1) and pyruvate dehydrogenase kinase isozyme 4 (PDK4), and several genes acting in lipid efflux and energy expenditure. Furthermore, 95EEAI stimulated fatty acid oxidation in a PPAR?-dependent manner. High-fat diet-induced obese mice model further indicated that administration of 95EEAI attenuated diet-induced obesity through the activation of fatty acid oxidation in skeletal muscle. These results suggest that a 95% ethanol extract of AI may have a role as a new functional food material for the prevention and/or treatment of hyperlipidermia and obesity. PMID:22479450

Cho, Si Young; Jeong, Hyun Woo; Sohn, Jong Hee; Seo, Dae-Bang; Kim, Wan Gi; Lee, Sang-Jun

2012-01-01

113

Efficient synthesis of fatty monoglyceride sulfates from fatty acids and fatty acid methyl esters  

Microsoft Academic Search

An efficient high yield synthesis of fatty monoglyceride sulfates from fatty acids or fatty acid methyl esters, glycerine\\u000a and chlorosulfuric acid in chloroform using stoichiometric amounts of reagents was developed. Sodium coco monoglyceride sulfate\\u000a was prepared in 79% yield with 93% purity from coco fatty acids. Similarly, sodium palm kernel monoglyceride sulfate in 57%\\u000a yield and sodium palm monoglyceride sulfate

Fahim U. Ahmed

1990-01-01

114

Myrtus communis berry color morphs: a comparative analysis of essential oils, fatty acids, phenolic compounds, and antioxidant activities.  

PubMed

Extracts of mature dark blue and white berries from two Tunisian Myrtus communis morphs growing at the same site were assessed for their essential-oil and fatty-acid compositions, phenolic contents, and antioxidant activities. The GC and GC/MS analyses of the essential oils allowed the identification of 33?constituents. The oils from the dark blue fruits showed high percentages of ?-pinene (11.1%), linalool (11.6%), ?-terpineol (15.7%), methyl eugenol (6.2%), and geraniol (3.7%). Myrtenyl acetate (20.3%) was found to be the major compound in the oils from white berries. GC Analysis of the pericarp and seed fatty acids showed that the polyunsaturated fatty acids constituted the major fraction (54.3-78.1%). The highest percentages of linoleic acid (78.0%) and oleic acid (20.0%) were observed in the seeds and the pericarps of the white fruits, respectively. The total phenol, flavonoid, and flavonol contents and the concentration of the eight anthocyanins, identified by HPLC analysis, were significantly higher in the dark blue fruits. All extracts showed a substantial antioxidant activity, assessed by the free radical-scavenging activity and the ferric reducing power, with the dark blue fruit extracts being more effective. PMID:21337502

Messaoud, Chokri; Boussaid, Mohamed

2011-02-01

115

Fatty acids regulate perilipin5 in muscle by activating PPAR?[S  

PubMed Central

The surface of lipid droplets (LDs) in various cell types is coated with perilipin proteins encoded by the Plin genes. Perilipins regulate LD metabolism by selectively recruiting lipases and other proteins to LDs. We have studied the expression of perilipins in mouse muscle. The glycolytic fiber-enriched gastrocnemius muscle expresses predominantly Plin2-4. The oxidative fiber-enriched soleus muscle expresses Plin2-5. Expression of Plin2 and Plin4-5 is elevated in gastrocnemius and soleus muscles from mice fed a high-fat diet. This effect is preserved in peroxisome proliferator-activated receptor (PPAR)?-deficient mice. Mouse muscle derived C2C12 cells differentiated into glycolytic fibers increase transcription of these Plins when exposed to various long chain fatty acids (FAs). To understand how FAs regulate Plin genes, we used specific activators and antagonists against PPARs, Plin promoter reporter assays, chromatin immunoprecipitation, siRNA, and animal models. Our analyses demonstrate that FAs require PPAR? to induce transcription of Plin4 and Plin5. We further identify a functional PPAR binding site in the Plin5 gene and establish Plin5 as a novel direct PPAR? target in muscle. Our study reveals that muscle cells respond to elevated FAs by increasing transcription of several perilipin LD-coating proteins. This induction renders the muscle better equipped to sequester incoming FAs into cytosolic LDs. PMID:23606724

Bindesbøll, Christian; Berg, Ole; Arntsen, Borghild; Nebb, Hilde I.; Dalen, Knut Tomas

2013-01-01

116

Relation of fatty acid composition in lead-exposed mallards to fat mobilization, lipid peroxidation and alkaline phosphatase activity  

USGS Publications Warehouse

The increase of n-6 polyunsaturated fatty acids (PUFA) in animal tissues has been proposed as a mechanism of Pb poisoning through lipid peroxidation or altered eicosanoids metabolism. We have studied fatty acid (FA) composition in liver and brain of mallards (Anas platyrhynchos) feeding for three weeks on diets containing combinations of low or high levels of vitamin E (20 or 200 UI/kg) and Pb (0 or 2 g/kg). Saturated FA, n-6 PUFA and total concentrations of FA were higher in livers of Pb-exposed mallards, but not in their brains. The percentage of n-6 PUFA in liver and brain was slightly higher in Pb-exposed mallards. The increase of n-6 PUFA in liver was associated with increased triglycerides and cholesterol in plasma, thus could be in part attributed to feed refusal and fat mobilization. The hepatic ratios between adrenic acid (22:4 n-6) and arachidonic acid (20:4 n-6) or between adrenic acid and linoleic acid (18:2 n-6) were higher in Pb exposed birds, supporting the existing hypothesis of increased fatty acid elongation by Pb. Among the possible consequences of increased n-6 PUFA concentration in tissues, we found increased lipid peroxidation in liver without important histopathological changes, and decreased plasma alkaline phosphatase activity that may reflect altered bone metabolism in birds.

Mateo, R.; Beyer, W.N.; Spann, J.W.; Hoffman, D.J.

2003-01-01

117

Effects of dietary fatty acid composition on the regulation of carnitine palmitoyltransferase (CPT) I in rainbow trout (Oncorhynchus mykiss)  

E-print Network

polyunsaturated fatty acid (PUFA) diet, a high saturated fatty acid (SFA) diet or a mixed fatty acid control (CTL Peroxisome proliferator activated receptor Polyunsaturated fatty acids Rainbow trout Dietary fatty acid composition, particularly polyunsaturated fatty acids, can affect both genetic and non- genetic regulatory

McClelland, Grant B.

118

Structure–Activity Relationships of ?-Keto Oxazole Inhibitors of Fatty Acid Amide Hydrolase  

PubMed Central

A systematic study of the structure–activity relationships (SAR) of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, Ki = 2.6 nM) with 5hh (aryl = 3-Cl-Ph, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally-restricted C2 side chains were examined and many provided exceptionally potent inhibitors of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteomic-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases. PMID:17559203

Hardouin, Christophe; Kelso, Michael J.; Romero, F. Anthony; Rayl, Thomas J.; Leung, Donmienne; Hwang, Inkyu; Cravatt, Benjamin F.; Boger, Dale L.

2008-01-01

119

Fatty acid metabolism and vascular disease.  

PubMed

Fatty acid metabolism is abnormal in insulin-resistant states that increase the risk of atherosclerosis such as type 2 diabetes and the metabolic syndrome. How fatty acids promote vascular disease is poorly understood, but lipoprotein lipase and peroxisome proliferator-activated receptor alpha (PPARalpha)-physiologically related proteins involved in fatty acid metabolism-may be involved. Glucocorticoid metabolism is also abnormal in insulin-resistant states and may promote several components of the metabolic syndrome. Recent studies have shown that hepatic fatty acid metabolism is required for the development of insulin resistance and hypertension caused by glucocorticoid excess, suggesting that crosstalk between glucocorticoid receptor-and PPARalpha-dependent pathways may contribute to vascular disease. PMID:15030793

Semenkovich, Clay F

2004-02-01

120

The liver-enriched transcription factor CREBH is nutritionally regulated and activated by fatty acids and PPAR{alpha}  

SciTech Connect

To elucidate the physiological role of CREBH, the hepatic mRNA and protein levels of CREBH were estimated in various feeding states of wild and obesity mice. In the fast state, the expression of CREBH mRNA and nuclear protein were high and profoundly suppressed by refeeding in the wild-type mice. In ob/ob mice, the refeeding suppression was impaired. The diet studies suggested that CREBH expression was activated by fatty acids. CREBH mRNA levels in the mouse primary hepatocytes were elevated by addition of the palmitate, oleate and eicosapenonate. It was also induced by PPAR{alpha} agonist and repressed by PPAR{alpha} antagonist. Luciferase reporter gene assays indicated that the CREBH promoter activity was induced by fatty acids and co-expression of PPAR{alpha}. Deletion studies identified the PPRE for PPAR{alpha} activation. Electrophoretic mobility shift assay and chromatin immunoprecipitation (ChIP) assay confirmed that PPAR{alpha} directly binds to the PPRE. Activation of CREBH at fasting through fatty acids and PPAR{alpha} suggest that CREBH is involved in nutritional regulation.

Danno, Hirosuke; Ishii, Kiyo-aki; Nakagawa, Yoshimi; Mikami, Motoki; Yamamoto, Takashi; Yabe, Sachiko; Furusawa, Mika; Kumadaki, Shin; Watanabe, Kazuhisa; Shimizu, Hidehisa; Matsuzaka, Takashi; Kobayashi, Kazuto; Takahashi, Akimitsu; Yatoh, Shigeru; Suzuki, Hiroaki; Yamada, Nobuhiro [Department of Internal Medicine (Endocrinology and Metabolism), Graduate School of Comprehensive Human Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba Ibaraki 305-8575 (Japan)] [Department of Internal Medicine (Endocrinology and Metabolism), Graduate School of Comprehensive Human Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba Ibaraki 305-8575 (Japan); Shimano, Hitoshi, E-mail: hshimano@md.tsukuba.ac.jp [Department of Internal Medicine (Endocrinology and Metabolism), Graduate School of Comprehensive Human Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba Ibaraki 305-8575 (Japan)] [Department of Internal Medicine (Endocrinology and Metabolism), Graduate School of Comprehensive Human Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba Ibaraki 305-8575 (Japan)

2010-01-08

121

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

PubMed

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 ?5- and ?6-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. PMID:25448610

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

2015-01-01

122

Fatty Acids Homeostasis; the search for  

E-print Network

Fatty Acids Homeostasis; the search for the key regulatory factors. --Andrew Knyazev, Math CUStargardt''ss--like macular degenerationlike macular degeneration FA metabolic proteins in diseases #12;FA Homeostasis of the Fatty Acids moleculesFatty Acids molecules !! The mechanism of Fatty Acid homeostasis is not understood

Knyazev, Andrew

123

Biol 458 Lecture 6 & 7 Fatty Acids 1 A. Introduction to acyl lipids (fatty acids)  

E-print Network

-Chain FA (VLCFAs) C24-32 - i.e. erucic acid (rapeseed) - ie. for waxes and cutin - as acyl-CoA #12;Biol 458 Lecture 6 & 7 Fatty Acids 1 A. Introduction to acyl lipids (fatty acids): Why study plant fatty acids Outline: 1. Structure and diversity of acyl lipids and fatty acids 2. Biosynthesis of fatty

Constabel, Peter

124

Inhibitors of Fatty Acid Synthesis and Elongation  

NSDL National Science Digital Library

Fatty acid synthesis and fatty acid elongation are two parts of a critically important pathway in plants. The endproducts are essential components of cell membranes, waxes, and suberin. Two chemical families of herbicide (groups that share similar chemical structures) inhibit fatty acid synthesis, while fatty acid elongation is inhibited by two other families. This lesson will provide an overview of fatty acid synthesis and elongation, and explain where herbicides inhibit the pathway. Mechanisms of resistance to these herbicides will be described.

125

Accumulation fatty acids of in Chlorella vulgaris under heterotrophic conditions in relation to activity of acetyl-CoA carboxylase, temperature, and co-immobilization with Azospirillum brasilense  

NASA Astrophysics Data System (ADS)

The relation between fatty acid accumulation, activity of acetyl-CoA carboxylase (ACC), and consequently lipid accumulation was studied in the microalgae Chlorella vulgaris co-immobilized with the plant growth-promoting bacterium Azospirillum brasilense under dark heterotrophic conditions with Na acetate as a carbon source. In C. vulgaris immobilized alone, cultivation experiments for 6 days showed that ACC activity is directly related to fatty acid accumulation, especially in the last 3 days. In co-immobilization experiments, A. brasilense exerted a significant positive effect over ACC activity, increased the quantity in all nine main fatty acids, increased total lipid accumulation in C. vulgaris, and mitigated negative effects of nonoptimal temperature for growth. No correlation between ACC activity and lipid accumulation in the cells was established for three different temperatures. This study demonstrated that the interaction between A. brasilense and C. vulgaris has a significant effect on fatty acid and lipid accumulation in the microalgae.

Leyva, Luis A.; Bashan, Yoav; Mendoza, Alberto; de-Bashan, Luz E.

2014-10-01

126

Accumulation fatty acids of in Chlorella vulgaris under heterotrophic conditions in relation to activity of acetyl-CoA carboxylase, temperature, and co-immobilization with Azospirillum brasilense.  

PubMed

The relation between fatty acid accumulation, activity of acetyl-CoA carboxylase (ACC), and consequently lipid accumulation was studied in the microalgae Chlorella vulgaris co-immobilized with the plant growth-promoting bacterium Azospirillum brasilense under dark heterotrophic conditions with Na acetate as a carbon source. In C. vulgaris immobilized alone, cultivation experiments for 6 days showed that ACC activity is directly related to fatty acid accumulation, especially in the last 3 days. In co-immobilization experiments, A. brasilense exerted a significant positive effect over ACC activity, increased the quantity in all nine main fatty acids, increased total lipid accumulation in C. vulgaris, and mitigated negative effects of nonoptimal temperature for growth. No correlation between ACC activity and lipid accumulation in the cells was established for three different temperatures. This study demonstrated that the interaction between A. brasilense and C. vulgaris has a significant effect on fatty acid and lipid accumulation in the microalgae. PMID:25129521

Leyva, Luis A; Bashan, Yoav; Mendoza, Alberto; de-Bashan, Luz E

2014-10-01

127

The crystal structure of yeast fatty acid synthase, a cellular machine with eight active sites working together.  

PubMed

In yeast, the whole metabolic pathway for making 16- and 18-carbon fatty acids is carried out by fatty acid synthase, a 2.6 megadalton molecular-weight macromolecular assembly containing six copies of all eight catalytic centers. We have determined its crystal structure, which illuminates how this enzyme is initially activated and then carries out multiple steps of synthesis in each of six sterically isolated reaction chambers. Six of the catalytic sites are in the wall of the assembly facing an acyl carrier protein (ACP) bound to the ketoacyl synthase domain. Two-dimensional diffusion of substrates to the catalytic sites may be achieved by the electrostatically negative ACP swinging to each of the six electrostatically positive catalytic sites. The phosphopantetheinyl transferase domain lies outside the shell of the assembly, inaccessible to ACP that lies inside, suggesting that the attachment of the pantetheine arm to ACP must occur before complete assembly of the complex. PMID:17448991

Lomakin, Ivan B; Xiong, Yong; Steitz, Thomas A

2007-04-20

128

The linoleic acid and trans fatty acids of margarines1  

Microsoft Academic Search

Fifty brands of margarine were analysed for cis-polyunsaturated acids by lipox- idase, for trans fatty acid by infrared spectroscopy, and for fatty acid composition by gas-liquid chromatography. High concentrations of trans fatty acids tended to be associated with low concentrations of hinoleic acid. Later analyses on eight of the brands, representing various proportions of linoleic to trans fatty acids, indicated

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

129

Variation of Photosynthesis, Fatty Acid Composition, ATPase and Acid Phosphatase Activities, and Anatomical Structure of Two Tea (Camellia sinensis (L.) O. Kuntze) Cultivars in Response to Fluoride  

PubMed Central

The changes of photosynthetic parameters, water use efficiency (WUE), fatty acid composition, chlorophyll (Chl) content, malondialdehyde (MDA) content, ATPase and acid phosphatase activities, fluoride (F) content, and leaf anatomical structure of two tea cultivars, “Pingyangtezao” (PY) and “Fudingdabai” (FD), after F treatments were investigated. The results show that net photosynthetic rate (Pn), stomatal conductance (gs), and transpiration rate (E) significantly decreased in both cultivars after 0.3?mM F treatment, but FD had higher Pn, gs, and WUE and lower E than PY. Chl content in PY significantly decreased after 0.2 and 0.3?mM F treatments, while no significant changes were observed in FD. The proportions of shorter chain and saturated fatty acids increased and those of longer chain and unsaturated fatty acids decreased in both cultivars under F treatments. The contents of MDA increased after F treatments but were higher in PY than in FD. In addition, F treatments decreased the activities of ATPase and acid phosphatase and increased F content in both cultivars; however, compared with PY, FD showed higher enzymatic activities and lower F content in roots and leaves. Leaf anatomical structure in FD indicated that cells in leaf midrib region were less injured by F than in PY. PMID:24023526

Wang, L. X.; Tang, J. H.; Xiao, B.; Yang, Y. J.; Liu, J.

2013-01-01

130

Free fatty acids in the cuticular and internal lipids of Calliphora vomitoria and their antimicrobial activity.  

PubMed

The cuticular and internal lipid composition in Calliphora vomitoria larvae, pupae, and male and female adults was studied. The free fatty acid (FA) compositions of the lipids were chemically characterized using gas chromatography (GC) and gas chromatography-electron impact mass spectrometry (GC-MS). Analyses of cuticular extracts from larvae, pupae, and male and female adults revealed that the carbon numbers of the acids ranged from C7:0 to C22:0, from C8:0 to C24:0, from C7:0 to C24:0 and from C7:0 to C22:0 respectively. The internal lipids of C. vomitoria larvae, pupae, male and female adults contained FAs ranging from C8:0 to C20:0, from C9:0 to C22:0, from C8:0 to C24:0 and from C9:0 to C22:0 respectively. Nine FAs with odd-numbered carbon chains from C7:0 to C21:0 were identified in the cuticular lipids of the larvae. The internal lipids of C. vomitoria larvae contained 8 odd-numbered FAs ranging from C9:0 to C19:0. Eight odd-numbered FAs from C9:0 to C21:0 were identified in the cuticular and internal lipids of pupae, while nine such FAs were found in the cuticular lipids of male and female adults. The internal lipids of adult males and females respectively contained nine and seven odd-numbered FAs, while both larvae and pupae contained eight such compounds. Eight unsaturated FAs were identified in the cuticular lipids of larvae, adult males and females and also in the internal lipids of females. Seven unsaturated FAs were identified in the cuticular lipids of pupae. The internal lipids of larvae, pupae and males contained 10, 11 and 12 unsaturated FAs respectively. Developmental changes were found both in the amounts of extracted cuticular and internal FAs and in their profiles. Four cuticular FAs (C7:0, C9:0, C10:0 and C15:1), identified as being male-specific, were either absent in the female cuticle or present there only in trace amounts. Cuticular and internal extracts obtained from larvae, pupae, adult males and females were tested for their potential antimicrobial activity. The minimal inhibitory concentrations of extracts against reference strains of bacteria and fungi were determined. Antimicrobial activity was the strongest against Gram-positive bacteria; Gram-negative bacteria, on the other hand, turned out to be resistant to all the lipids tested. Overall, the activities of the internal lipids were stronger. All the lipid extracts were equally effective against all the fungal strains examined. In contrast, crude extracts containing both cuticular and internal lipids displayed no antifungal activity against the entomopathogenic fungus Conidiobolus coronatus, which efficiently killed adult flies, but not larvae or pupae. PMID:23419415

Go??biowski, Marek; Cerkowniak, Magdalena; Bogu?, Mieczys?awa I; W?óka, Emilia; Dawgul, Ma?gorzata; Kamysz, Wojciech; Stepnowski, Piotr

2013-04-01

131

Mediator Subunit Gal11p/MED15 Is Required for Fatty Acid-dependent Gene Activation by Yeast Transcription Factor Oaf1p*  

PubMed Central

The yeast zinc cluster transcription factor Oaf1p activates transcription of target genes in response to direct binding of fatty acids in a manner analogous to the vertebrate nuclear receptor peroxisome proliferator-activated receptor ? (PPAR?). PPARs and other metazoan nuclear receptors productively engage several distinct LXXLL motif-containing co-activators, including p160 family members and the TRAP220/MED1 subunit of the Mediator co-activator, to promote ligand-dependent gene activation. Yeast, however, does not appear to harbor LXXLL motif co-activators, and the mechanism of fatty acid-dependent gene activation by the yeast PPAR? analog Oaf1p is unknown. Here we show that the yeast Mediator subunit Gal11p/MED15 and its activator-targeted KIX domain plays a critical role in fatty acid-dependent transcriptional regulation of fatty acid ?-oxidation and peroxisomal genes by Oaf1p and for the ability of yeast to utilize fatty acids as a sole carbon source. Moreover, structural studies by NMR spectroscopy reveal that the Oaf1p activation domain interacts with the Gal11p/MED15 KIX domain in a manner similar to the yeast zinc cluster family member and xenobiotic receptor Pdr1p, revealing that the Gal11p/MED15 KIX domain is a key target of several ligand-dependent transcription factors in yeast. Together with previous work showing that the Caenorhabditis elegans Gal11p/MED15 homolog MDT-15 plays a critical role in regulation of fatty acid metabolism by the nematode PPAR-like nuclear receptor NHR-49, the findings presented here provide evidence for an ancient and essential role of a Mediator co-activator subunit in regulation of fatty acid metabolism by nuclear receptor-like transcription factors in eukaryotes. PMID:19056732

Thakur, Jitendra K.; Arthanari, Haribabu; Yang, Fajun; Chau, Katherine H.; Wagner, Gerhard; Näär, Anders M.

2009-01-01

132

Activation of the protein deacetylase SIRT6 by long-chain fatty acids and widespread deacylation by mammalian sirtuins.  

PubMed

Mammalian sirtuins (SIRT1 through SIRT7) are members of a highly conserved family of NAD(+)-dependent protein deacetylases that function in metabolism, genome maintenance, and stress responses. Emerging evidence suggests that some sirtuins display substrate specificity toward other acyl groups attached to the lysine ?-amine. SIRT6 was recently reported to preferentially hydrolyze long-chain fatty acyl groups over acetyl groups. Here we investigated the catalytic ability of all sirtuins to hydrolyze 13 different acyl groups from histone H3 peptides, ranging in carbon length, saturation, and chemical diversity. We find that long-chain deacylation is a general feature of mammalian sirtuins, that SIRT1 and SIRT2 act as efficient decrotonylases, and that SIRT1, SIRT2, SIRT3, and SIRT4 can remove lipoic acid. These results provide new insight into sirtuin function and a means for cellular removal of an expanding list of endogenous lysine modifications. Given that SIRT6 is a poor deacetylase in vitro, but binds and prefers to hydrolyze long-chain acylated peptides, we hypothesize that binding of certain free fatty acids (FFAs) could stimulate deacetylation activity. Indeed, we demonstrate that several biologically relevant FFAs (including myristic, oleic, and linoleic acids) at physiological concentrations induce up to a 35-fold increase in catalytic efficiency of SIRT6 but not SIRT1. The activation mechanism is consistent with fatty acid inducing a conformation that binds acetylated H3 with greater affinity. Binding of long-chain FFA and myristoylated H3 peptide is mutually exclusive. We discuss the implications of discovering endogenous, small-molecule activators of SIRT6. PMID:24052263

Feldman, Jessica L; Baeza, Josue; Denu, John M

2013-10-25

133

Activation of the Protein Deacetylase SIRT6 by Long-chain Fatty Acids and Widespread Deacylation by Mammalian Sirtuins* ?  

PubMed Central

Mammalian sirtuins (SIRT1 through SIRT7) are members of a highly conserved family of NAD+-dependent protein deacetylases that function in metabolism, genome maintenance, and stress responses. Emerging evidence suggests that some sirtuins display substrate specificity toward other acyl groups attached to the lysine ?-amine. SIRT6 was recently reported to preferentially hydrolyze long-chain fatty acyl groups over acetyl groups. Here we investigated the catalytic ability of all sirtuins to hydrolyze 13 different acyl groups from histone H3 peptides, ranging in carbon length, saturation, and chemical diversity. We find that long-chain deacylation is a general feature of mammalian sirtuins, that SIRT1 and SIRT2 act as efficient decrotonylases, and that SIRT1, SIRT2, SIRT3, and SIRT4 can remove lipoic acid. These results provide new insight into sirtuin function and a means for cellular removal of an expanding list of endogenous lysine modifications. Given that SIRT6 is a poor deacetylase in vitro, but binds and prefers to hydrolyze long-chain acylated peptides, we hypothesize that binding of certain free fatty acids (FFAs) could stimulate deacetylation activity. Indeed, we demonstrate that several biologically relevant FFAs (including myristic, oleic, and linoleic acids) at physiological concentrations induce up to a 35-fold increase in catalytic efficiency of SIRT6 but not SIRT1. The activation mechanism is consistent with fatty acid inducing a conformation that binds acetylated H3 with greater affinity. Binding of long-chain FFA and myristoylated H3 peptide is mutually exclusive. We discuss the implications of discovering endogenous, small-molecule activators of SIRT6. PMID:24052263

Feldman, Jessica L.; Baeza, Josue; Denu, John M.

2013-01-01

134

Fatty Acid and Essential Oil Compositions of Trifolium angustifolium var. angustifolium with Antioxidant, Anticholinesterase and Antimicrobial Activities  

PubMed Central

This study represents the first report on the chemical composition and biological activity of Trifolium angustifolium var. angustifolium. The major components of the essential oil were identified as hexatriacontene (23.0%), arachidic acid (15.5%) and ?-selinene (10.0%). The main constituents of the fatty acid obtained from the petroleum ether extract were identified as palmitic acid (29.8%), linoleic acid (18.6%) and oleic acid (10.5%). In particular, the water extract exhibited higher activity than ?-tocopherol and BHT, which were used as standards in the ABTS cation radical scavenging assay and indicated higher inhibitory effect against acetylcholinesterase enzyme than the reference compound, galanthamine but exhibited weak activity in ?-carotene bleaching, DPPH-free radical scavenging, and cupric-reducing antioxidant capacity assays. The petroleum ether extract exhibited higher activity than ?-tocopherol which was used as standard in the ?-carotene bleaching method at concentration 100 ?g/mL. The acetone extract exhibited higher activity than ?-tocopherol which was used as standard cupric reducing antioxidant capacity (CUPRAC) method at 100 ?g/mL concentration. The acetone and methanol extracts were active on all microorganisms tested with a small zone diameter indicating weak activity. PMID:25561929

Erta?, Abdulselam; Bo?a, Mehmet; Ha?imi, Nesrin; Y?lmaz, Mustafa Abdullah

2015-01-01

135

Fatty Acid and Essential Oil Compositions of Trifolium angustifolium var. angustifolium with Antioxidant, Anticholinesterase and Antimicrobial Activities.  

PubMed

This study represents the first report on the chemical composition and biological activity of Trifolium angustifolium var. angustifolium. The major components of the essential oil were identified as hexatriacontene (23.0%), arachidic acid (15.5%) and ?-selinene (10.0%). The main constituents of the fatty acid obtained from the petroleum ether extract were identified as palmitic acid (29.8%), linoleic acid (18.6%) and oleic acid (10.5%). In particular, the water extract exhibited higher activity than ?-tocopherol and BHT, which were used as standards in the ABTS cation radical scavenging assay and indicated higher inhibitory effect against acetylcholinesterase enzyme than the reference compound, galanthamine but exhibited weak activity in ?-carotene bleaching, DPPH-free radical scavenging, and cupric-reducing antioxidant capacity assays. The petroleum ether extract exhibited higher activity than ?-tocopherol which was used as standard in the ?-carotene bleaching method at concentration 100 ?g/mL. The acetone extract exhibited higher activity than ?-tocopherol which was used as standard cupric reducing antioxidant capacity (CUPRAC) method at 100 ?g/mL concentration. The acetone and methanol extracts were active on all microorganisms tested with a small zone diameter indicating weak activity. PMID:25561929

Erta?, Abdulselam; Bo?a, Mehmet; Ha?imi, Nesrin; Y?lmaz, Mustafa Abdullah

2015-01-01

136

Medium Chain Fatty Acids Are Selective Peroxisome Proliferator Activated Receptor (PPAR) ? Activators and Pan-PPAR Partial Agonists  

PubMed Central

Thiazolidinediones (TZDs) act through peroxisome proliferator activated receptor (PPAR) ? to increase insulin sensitivity in type 2 diabetes (T2DM), but deleterious effects of these ligands mean that selective modulators with improved clinical profiles are needed. We obtained a crystal structure of PPAR? ligand binding domain (LBD) and found that the ligand binding pocket (LBP) is occupied by bacterial medium chain fatty acids (MCFAs). We verified that MCFAs (C8–C10) bind the PPAR? LBD in vitro and showed that they are low-potency partial agonists that display assay-specific actions relative to TZDs; they act as very weak partial agonists in transfections with PPAR? LBD, stronger partial agonists with full length PPAR? and exhibit full blockade of PPAR? phosphorylation by cyclin-dependent kinase 5 (cdk5), linked to reversal of adipose tissue insulin resistance. MCFAs that bind PPAR? also antagonize TZD-dependent adipogenesis in vitro. X-ray structure B-factor analysis and molecular dynamics (MD) simulations suggest that MCFAs weakly stabilize C-terminal activation helix (H) 12 relative to TZDs and this effect is highly dependent on chain length. By contrast, MCFAs preferentially stabilize the H2-H3/?-sheet region and the helix (H) 11-H12 loop relative to TZDs and we propose that MCFA assay-specific actions are linked to their unique binding mode and suggest that it may be possible to identify selective PPAR? modulators with useful clinical profiles among natural products. PMID:22649490

Ayers, Steven D.; Lin, Jean Z.; Cvoro, Aleksandra; Silveira, Rodrigo L.; Martínez, Leandro; Souza, Paulo C. T.; Saidemberg, Daniel; Deng, Tuo; Amato, Angela Angelica; Togashi, Marie; Hsueh, Willa A.; Phillips, Kevin; Palma, Mário Sérgio; Neves, Francisco A. R.; Skaf, Munir S.; Webb, Paul; Polikarpov, Igor

2012-01-01

137

Fatty acid-derived signals in plants.  

PubMed

Plants synthesize many fatty acid derivatives, several of which play important regulatory roles. Jasmonates are the best characterized examples. Jasmonate-insensitive mutants and mutants with a constitutive jasmonate response have given us new insights into jasmonate signalling. The jasmonate biosynthesis mutant opr3 allowed the dissection of cyclopentanone and cyclopentenone signalling, thus defining specific roles for these molecules. Jasmonate signalling is a complex network of individual signals and recent findings on specific activities of methyl jasmonate and (Z)-jasmone add to this picture. In addition, there are keto, hydroxy and hydroperoxy fatty acids that might be involved in cell death and the expression of stress-related genes. Finally, there are bruchins and volicitin, signal molecules from insects that are perceived by plants in the picomole to femtomole range. They highlight the importance of fatty acid-derived molecules in interspecies communication and in plant defence. PMID:11992827

Weber, Hans

2002-05-01

138

Hepatic fatty acid oxidation enzyme activities are stimulated in rats fed the brown seaweed, Undaria pinnatifida (wakame).  

PubMed

The activities of hepatic enzymes involved in fatty acid synthesis and oxidation were compared in rats fed diets containing different proportions of dried powder of the brown seaweed, Undaria pinnatifida (wakame). Rats were fed diets containing 0, 0.5, 1.0, 2. 0, 5.0 and 10 g/100 g of dried wakame powder. Experimental diets were adjusted to provide consistent amounts of most nutrients, but mineral concentrations were not standardized. After the 21-d feeding period, serum and liver triacylglycerol levels in rats fed diets in which wakame constituted at least 2% were significantly lower than those in rats fed the control diet. The activity of glucose-6-phosphate dehydrogenase was significantly lower in rats fed the 5 and 10% wakame diets than in rats fed the control diet. In contrast, 10% wakame diet increased activities of enzymes involved in the beta-oxidation pathway including hepatic carnitine palmitoyltransferase, acyl-CoA dehydrogenase, acyl-CoA oxidase, enoyl-CoA hydratase and 2,4-dienoyl-CoA reductase. Some differences were detected in rats fed 5% wakame as well. These results suggest that alterations of the activities of enzymes involved in fatty acid metabolism in the liver are responsible for the serum triacylglycerol-lowering effect of dietary wakame. Thus, wakame may be useful as a food to prevent hyperlipidemia. PMID:9915891

Murata, M; Ishihara, K; Saito, H

1999-01-01

139

p38 mitogen-activated protein kinase interacts with vinculin at focal adhesions during fatty acid-stimulated cell adhesion  

PubMed Central

Arachidonic acid stimulates cell adhesion by activating ?2?1 integrins in a process that depends on protein kinases, including p38 mitogen activated protein kinase. Here, we describe the interaction of cytoskeletal components with key signaling molecules that contribute to spreading of, and morphological changes in, arachidonic acid-treated MDA-MB-435 human breast carcinoma cells. Arachidonic acid-treated cells showed increased attachment and spreading on collagen type IV as measured by electric cell-substrate impedance sensing. Fatty acid-treated cells displayed short cortical actin filaments associated with an increased number of ?1 integrin-containing pseudopodia whereas untreated cells displayed elongated stress fibers and fewer clusters of ?1 integrins. Confocal microscopy of arachidonic acid-treated cells showed that vinculin and phospho-p38 both appeared enriched in pseudopodia and at the tips of actin filaments, and fluorescence ratio imaging indicated the increase was specific for the phospho-(active) form of p38. Immunoprecipitates of phospho-p38 from extracts of arachidonic acid-treated cells contained vinculin, and GST-vinculin fusion proteins carrying the central region of vinculin bound phospho-p38, whereas fusion proteins expressing the terminal portions of vinculin did not. These data suggest that phospho-p38 associates with particular domains on critical focal adhesion proteins that are involved in tumor cell adhesion and spreading and that this association can be regulated by factors in the tumor microenvironment. PMID:24219282

George, Margaret D.; Wine, Robert N.; Lackford, Brad; Kissling, Grace E.; Akiyama, Steven K.; Olden, Kenneth; Roberts, John D.

2014-01-01

140

Carnitine palmitoyl transferase activity and whole muscle oxidation rates vary with fatty acid substrate in avian flight muscles.  

PubMed

Birds primarily fuel migratory flights with fat, and the composition of that fat has the potential to affect overall lipid oxidation rates. We measured the whole muscle lipid oxidation rates in extensor digitorum communis muscles from white-throated sparrows (Zonotrichia albicollis Gmelin) incubated for 20 min at 20°C with radiolabeled stearate (18:0), oleate (18:1?9), or linoleate (18:2?6). Lipid oxidation rates were ~40% higher with linoleate than oleate (oleate: 36 ± 8.54 ?mol CO(2) g(-1) h(-1)), and ~75% lower with stearate compared with oleate, indicating that maximal lipid oxidation rates can indeed be affected by the type of fatty acid supplied to the muscle. Additionally, we investigated the activity of the mitochondrial fatty acid transport-associated enzyme carnitine palmitoyl transferase (CPT) in pectoralis muscles of 5 bird species (Zonotrichia albicollis, Philomachus pugnax, Sturnus vulgaris, Taeniopygia guttata, Passer domesticus). Activity was measured in homogenized samples using various fatty acyl-CoA substrates (16:0, 16:1, 18:0, 18:1?9, 18:2?6, 18:3?3, 18:3?6, 20:0, 20:4?6, 22:6?3) in a spectrophotometric assay. CPT activity increased with the degree of unsaturation and decreased with chain length. CPT activity did not differ between ?3 and ?6 isomers of 18:3, nor was the pattern of CPT substrate preference different between captive white-throated sparrows in a migratory (i.e., displaying Zugunruhe) or non-migratory state. These findings can explain previously observed differences in peak performance induced by dietary fat composition and suggest that lipid supply is limiting to maximal exercise performance in birds. PMID:21153644

Price, Edwin R; Staples, James F; Milligan, C Louise; Guglielmo, Christopher G

2011-05-01

141

Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients.  

PubMed

Abnormal fatty acid metabolism may play an important role in the pathogenesis of essential hypertension (EH). We compared fasting serum free fatty acid (FFA) composition between EH patients and nonhypertensive (NH) subjects, and examined the relationships between fasting serum FFA composition and waist/hip ratio, insulin activity, blood pressure, serum zinc, age, and sex in both groups. We conducted a cross-sectional study of 232 community-dwelling subjects aged between 35 and 60 years: 109 EH patients and 123 NH subjects. Serum FFA was determined by HPLC analysis. The data were analyzed by multivariate linear stepwise regression, stratified analysis, and correlation analysis. In men, EH patients had lower C22:6/C20:5 ratios (n-3 Delta6-desaturase activity index, 7.96+/-8.81 vs. 14.5+/-13.1, p<0.01), polyunsaturated fatty acid (PUFA), n-3 PUFA and polyunsaturated/saturated (P/S) ratios compared with male subjects without hypertension. There were no differences in women. Fasting serum FFA composition was significantly related to many variables, including waist/hip ratio, insulin sensitivity index, and serum zinc (all p<0.05 or <0.01) for all the subjects, and included both age- and sex-related differences (both p<0.05). Compared with NH, EH patients had lower levels of serum zinc (14.9+/-5.00 micromol L(-1) vs. 16.8+/-6.38 micromol L(-1), p<0.05). We concluded that EH patients had marked alteration in fasting serum FFA composition, which was affected by upper body obesity, insulin resistance, zinc deficiency, and high dietary fat, and that the differences were age- and sex-related. PMID:18633173

Wang, Shun; Ma, Aiqun; Song, Shaowu; Quan, Qinghai; Zhao, Xinfeng; Zheng, Xiaohui

2008-04-01

142

Synthesis and evaluation of odour-active methionyl esters of fatty acids via esterification and transesterification of butter oil.  

PubMed

Methionol-derived fatty acid esters were synthesised by both chemical and lipase catalysed esterification between fatty acids and methionol. Beneficial effects of both methods were compared qualitatively and quantitatively by GC-MS/GC-FID results. And the high acid and heat stability of our designed methionyl esters meet the requirement of the food industry. Most importantly, the sensory test showed that fatty acid carbon-chain length had an important effect on the flavour attributes of methionyl esters. Moreover, through Lipozyme TL IM-mediated transesterification, valuable methionol-derived esters were synthesised from the readily available natural material butter oil as the fatty acid source. The conversion of methionol and yield of each methionyl ester were also elucidated by GC-MS-FID. PMID:24128547

Li, Cheng; Sun, Jingcan; Fu, Caili; Yu, Bin; Liu, Shao Quan; Li, Tianhu; Huang, Dejian

2014-02-15

143

Fatty Acids Suppress Autophagic Turnover in ?-Cells*  

PubMed Central

Recent studies have shown that autophagy is essential for proper ?-cell function and survival. However, it is yet unclear under what pathogenic conditions autophagy is inhibited in ?-cells. Here, we report that long term exposure to fatty acids and glucose block autophagic flux in ?-cells, contributing to their toxic effect. INS1 cells expressing GFP-LC3 (an autophagosome marker) were treated with 0.4 mm palmitate, 0.4 mm oleate, and various concentrations of glucose for 22 h. Kinetics of the effect of fatty acids on autophagy showed a biphasic response. During the second phase of autophagy, the size of autophagosomes and the content of autophagosome substrates (GFP-LC3, p62) and endogenous LC3 was increased. During the same phase, fatty acids suppressed autophagic degradation of long lived protein in both INS1 cells and islets. In INS1 cells, palmitate induced a 3-fold decrease in the number and the acidity of Acidic Vesicular Organelles. This decrease was associated with a suppression of hydrolase activity, suppression of endocytosis, and suppression of oxidative phosphorylation. The combination of fatty acids with glucose synergistically suppressed autophagic turnover, concomitantly suppressing insulin secretion. Rapamycin treatment resulted in partial reversal of the inhibition of autophagic flux, the inhibition of insulin secretion, and the increase in cell death. Our results indicate that excess nutrient could impair autophagy in the long term, hence contributing to nutrient-induced ?-cell dysfunction. This may provide a novel mechanism that connects diet-induced obesity and diabetes. PMID:21859708

Las, Guy; Serada, Sam B.; Wikstrom, Jakob D.; Twig, Gilad; Shirihai, Orian S.

2011-01-01

144

Dietary Saturated Fatty Acids and Brain Function  

Microsoft Academic Search

The degree to which fatty acids modulate brain function beyond periods of rapid brain growth is poorly understood. Nevertheless, recent evidence suggests that dietary fatty acid composition influences numerous behaviors including body temperature regulation, pain sensitivity, feeding behavior including macronutrient selection, and cognitive performance. Importantly, alterations are observed in the absence of essential fatty acid (EFA) deficiency, beyond periods of

Randall J. Kaplan; Carol E. Greenwood

1998-01-01

145

Essential Fatty Acids and the Brain  

Microsoft Academic Search

Objective: To review the role of essential fatty acids in brain membrane function and in the genesis of psychi- atric disease. Results: The fatty acid composition of neuronal cell membrane phospholipids reflects their intake in the diet. The degree of a fatty acid's desaturation determines its 3-dimensional structure and, thus, membrane fluidity and function. The ratio between omega-3 and omega-6

Marianne Haag

2003-01-01

146

Biological control of phytopathogenic fungi by fatty acids.  

PubMed

The aim of the present study was to evaluate the antifungal activity of fatty acids against phytopathogenic fungi. Two pot experiments were conducted by mixing palmitic and oleic acids in the soil in which poor plant growth was observed. In addition, the antifungal activities of nine fatty acids (butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, and linoleic acid) against four phytopathogenic fungi: Alternaria solani, Colletotrichum lagenarium, Fusarium oxysporum f. sp. Cucumerinum, and Fusarium oxysporum f. sp. lycopersici, were assessed by measuring mycelial growth and spore germination via Petri dish assay. The results of the pot experiments showed that the mixture of palmitic and oleic acids enhanced the growth of the seedlings of continuous-tomato and continuous-cucumber. Except for oleic acid, in the Petri dish assay, the fatty acids tested were observed to inhibit the mycelial growth of one or more tested fungi. In addition to the suppression of mycelial growth, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, and palmitic acid showed an inhibitory effect against spore germination and the extent of inhibition varied with both the type of fatty acids, and the fungi. In particular, capric acid displayed strong inhibitory effect against C. lagenarium on the mycelial growth and spore germination. The saturated fatty acids, i.e. palmitic acids, showed stronger antifungal activity than the unsaturated fatty acids, i.e. oleic acid. It suggests that fatty acids might be applicable to exploring for alternative approaches to integrated control of phytopathogens. PMID:18443921

Liu, Siyun; Ruan, Weibin; Li, Jing; Xu, Hua; Wang, Jingan; Gao, Yubao; Wang, Jingguo

2008-08-01

147

Fatty acid metabolism in adipocytes: functional analysis of fatty acid transport proteins 1 and 4.  

PubMed

The role of fatty acid transport protein 1 (FATP1) and FATP4 in facilitating adipocyte fatty acid metabolism was investigated using stable FATP1 or FATP4 knockdown (kd) 3T3-L1 cell lines derived from retrovirus-delivered short hairpin RNA (shRNA). Decreased expression of FATP1 or FATP4 did not affect preadipocyte differentiation or the expression of FATP1 (in FATP4 kd), FATP4 (in FATP1 kd), fatty acid translocase, acyl-coenzyme A synthetase 1, and adipocyte fatty acid binding protein but did lead to increased levels of peroxisome proliferator-activated receptor gamma and CCAAT/enhancer binding protein alpha. Both FATP1 and FATP4 kd adipocytes exhibited reduced triacylglycerol deposition and corresponding reductions in diacylglycerol and monoacylglycerol levels compared with control cells. FATP1 kd adipocytes displayed an approximately 25% reduction in basal (3)H-labeled fatty acid uptake and a complete loss of insulin-stimulated (3)H-labeled fatty acid uptake compared with control adipocytes. In contrast, FATP4 kd adipocytes as well as HEK-293 cells overexpressing FATP4 did not display any changes in fatty acid influx. FATP4 kd cells exhibited increased basal lipolysis, whereas FATP1 kd cells exhibited no change in lipolytic capacity. Consistent with reduced triacylglycerol accumulation, FATP1 and FATP4 kd adipocytes exhibited enhanced 2-deoxyglucose uptake compared with control adipocytes. These findings define unique and distinct roles for FATP1 and FATP4 in adipose fatty acid metabolism. PMID:17164224

Lobo, Sandra; Wiczer, Brian M; Smith, Ann J; Hall, Angela M; Bernlohr, David A

2007-03-01

148

Expression and characterization of an epoxide hydrolase from Anopheles gambiae with high activity on epoxy fatty acids.  

PubMed

In insects, epoxide hydrolases (EHs) play critical roles in the metabolism of xenobiotic epoxides from the food resources and in the regulation of endogenous chemical mediators, such as juvenile hormones. Using the baculovirus expression system, we expressed and characterized an epoxide hydrolase from Anopheles gambiae (AgEH) that is distinct in evolutionary history from insect juvenile hormone epoxide hydrolases (JHEHs). We partially purified the enzyme by ion exchange chromatography and isoelectric focusing. The experimentally determined molecular weight and pI were estimated to be 35 kD and 6.3 respectively, different than the theoretical ones. The AgEH had the greatest activity on long chain epoxy fatty acids such as 14,15-epoxyeicosatrienoic acids (14,15-EET) and 9,10-epoxy-12Z-octadecenoic acids (9,10-EpOME or leukotoxin) among the substrates evaluated. Juvenile hormone III, a terpenoid insect growth regulator, was the next best substrate tested. The AgEH showed kinetics comparable to the mammalian soluble epoxide hydrolases, and the activity could be inhibited by AUDA [12-(3-adamantan-1-yl-ureido) dodecanoic acid], a urea-based inhibitor designed to inhibit the mammalian soluble epoxide hydrolases. The rabbit serum generated against the soluble epoxide hydrolase of Mus musculus can both cross-react with natural and denatured forms of the AgEH, suggesting immunologically they are similar. The study suggests there are mammalian sEH homologs in insects, and epoxy fatty acids may be important chemical mediators in insects. PMID:25173592

Xu, Jiawen; Morisseau, Christophe; Hammock, Bruce D

2014-11-01

149

Omega-3 Fatty Acids Protect the Brain against Ischemic Injury by Activating Nrf2 and Upregulating Heme Oxygenase 1  

PubMed Central

Ischemic stroke is a debilitating clinical disorder that affects millions of people, yet lacks effective neuroprotective treatments. Fish oil is known to exert beneficial effects against cerebral ischemia. However, the underlying protective mechanisms are not fully understood. The present study tests the hypothesis that omega-3 polyunsaturated fatty acids (n-3 PUFAs) attenuate ischemic neuronal injury by activating nuclear factor E2-related factor 2 (Nrf2) and upregulating heme oxygenase-1 (HO-1) in both in vitro and in vivo models. We observed that pretreatment of rat primary neurons with docosahexaenoic acid (DHA) significantly reduced neuronal death following oxygen-glucose deprivation. This protection was associated with increased Nrf2 activation and HO-1 upregulation. Inhibition of HO-1 activity with tin protoporphyrin IX attenuated the protective effects of DHA. Further studies showed that 4-hydroxy-2E-hexenal (4-HHE), an end-product of peroxidation of n-3 PUFAs, was a more potent Nrf2 inducer than 4-hydroxy-2E-nonenal derived from n-6 PUFAs. In an in vivo setting, transgenic mice overexpressing fatty acid metabolism-1, an enzyme that converts n-6 PUFAs to n-3 PUFAs, were remarkably resistant to focal cerebral ischemia compared with their wild-type littermates. Regular mice fed with a fish oil-enhanced diet also demonstrated significant resistance to ischemia compared with mice fed with a regular diet. As expected, the protection was associated with HO-1 upregulation, Nrf2 activation, and 4-HHE generation. Together, our data demonstrate that n-3 PUFAs are highly effective in protecting the brain, and that the protective mechanisms involve Nrf2 activation and HO-1 upregulation by 4-HHE. Further investigation of n-3 PUFA neuroprotective mechanisms may accelerate the development of stroke therapies. PMID:24478369

Zhang, Meijuan; Wang, Suping; Mao, Leilei; Leak, Rehana K.; Shi, Yejie; Zhang, Wenting; Hu, Xiaoming; Sun, Baoliang; Cao, Guodong; Gao, Yanqin; Xu, Yun

2014-01-01

150

Regulation of Thrombospondin-1 expression in alternatively activated macrophages and adipocytes: role of cellular crosstalk and omega-3 fatty acids  

PubMed Central

Thrombospondin-1 (TSP-1) expression in human adipose positively correlates with body mass index and may contribute to adipose dysfunction by activating TGF-? and/or inhibiting angiogenesis. Our objective was to determine how TSP-1 is regulated in adipocytes and polarized macrophages using a coculture system and to determine whether fatty acids, including the ?-3 fatty acid DHA, regulate TSP-1 expression. Coculture of M1, M2a, or M2c macrophages with adipocytes induced TSP-1 gene expression in adipocytes (from 2.4 to 4.2-fold, P<0.05), and adipocyte coculture induced TSP-1 gene expression in M1 and M2c macrophages (M1:8.6-fold; M2c 26-fold, P<0.05). TSP-1 protein levels in the shared media of adipocytes and M2c cells was also strongly induced by coculture (>10 fold, P<0.05). DHA treatment during the coculture of adipocytes and M2c macrophages potently inhibited theM2c macrophage TSP-1 mRNA level (97% inhibition, P<0.05). Adipocyte coculture induced IL-10 expression in M2c macrophages (10.1-fold, P<0.05), and this increase in IL-10 mRNA expression was almost completely blocked with DHA treatment (96% inhibition, P<0.05); thus, IL-10 expression closely paralleled TSP-1 expression. Since IL-10 has been shown to regulate TSP-1 in other cell types, we reduced IL-10 expression with siRNA in the M2c cells and found that this caused TSP-1 to be reduced in response to adipocyte coculture by 60% (P<0.05), suggesting that IL-10 regulates TSP-1 expression in M2c macrophages. These results suggest that supplementation with dietary ?-3 fatty acids could potentially be beneficial to adipose tissue in obesity by reducing TSP-1 and fibrosis. PMID:23528972

Finlin, Brian S.; Zhu, Beibei; Starnes, Catherine P.; McGehee, Robert E.; Peterson, Charlotte A.; Kern, Philip A.

2013-01-01

151

PPAR/RXR Regulation of Fatty Acid Metabolism and Fatty Acid ?-Hydroxylase (CYP4) Isozymes: Implications for Prevention of Lipotoxicity in Fatty Liver Disease  

PubMed Central

Fatty liver disease is a common lipid metabolism disorder influenced by the combination of individual genetic makeup, drug exposure, and life-style choices that are frequently associated with metabolic syndrome, which encompasses obesity, dyslipidemia, hypertension, hypertriglyceridemia, and insulin resistant diabetes. Common to obesity related dyslipidemia is the excessive storage of hepatic fatty acids (steatosis), due to a decrease in mitochondria ?-oxidation with an increase in both peroxisomal ?-oxidation, and microsomal ?-oxidation of fatty acids through peroxisome proliferator activated receptors (PPARs). How steatosis increases PPAR? activated gene expression of fatty acid transport proteins, peroxisomal and mitochondrial fatty acid ?-oxidation and ?-oxidation of fatty acids genes regardless of whether dietary fatty acids are polyunsaturated (PUFA), monounsaturated (MUFA), or saturated (SFA) may be determined by the interplay of PPARs and HNF4? with the fatty acid transport proteins L-FABP and ACBP. In hepatic steatosis and steatohepatitis, the ?-oxidation cytochrome P450 CYP4A gene expression is increased even with reduced hepatic levels of PPAR?. Although numerous studies have suggested the role ethanol-inducible CYP2E1 in contributing to increased oxidative stress, Cyp2e1-null mice still develop steatohepatitis with a dramatic increase in CYP4A gene expression. This strongly implies that CYP4A fatty acid ?-hydroxylase P450s may play an important role in the development of steatohepatitis. In this review and tutorial, we briefly describe how fatty acids are partitioned by fatty acid transport proteins to either anabolic or catabolic pathways regulated by PPARs, and we explore how medium-chain fatty acid (MCFA) CYP4A and long-chain fatty acid (LCFA) CYP4F?-hydroxylase genes are regulated in fatty liver. We finally propose a hypothesis that increased CYP4A expression with a decrease in CYP4F genes may promote the progression of steatosis to steatohepatitis. PMID:20300478

Hardwick, James P.; Osei-Hyiaman, Douglas; Wiland, Homer; Abdelmegeed, Mohamed A.; Song, Byoung-Joon

2009-01-01

152

Constitutively-active TRPC channels of adipocytes confer a mechanism for sensing dietary fatty acids and regulating adiponectin  

PubMed Central

Rationale Calcium entry is pivotal in the heart and blood vessels but its significance and mechanisms in adipose tissue are largely unknown. An important factor produced by adipocytes is adiponectin, which confers myocardial protection, insulin-sensitisation, and anti-atherosclerotic effects. Objective To investigate the relevance of calcium channels to adipocytes and the production of adiponectin. Methods and Results Micro-array analysis led to identification of TRPC1 and TRPC5 as channel subunits that are induced when adipocytes mature. Both subunits were found in perivascular fat of patients with atherosclerosis. Intracellular calcium and patch-clamp measurements showed that adipocytes exhibit constitutively-active calcium-permeable non-selective cationic channels that depend on TRPC1 and TRPC5. The activity could be enhanced by lanthanum or rosiglitazone, known stimulators of TRPC5 and TRPC5-containing channels. Screening identified lipid modulators of the channels that are relevant to adipose biology. Dietary ?-3 fatty acids (e.g. ?-linolenic acid) were inhibitory at concentrations that are achieved by ingestion. The adipocyte TRPC1/TRPC5-containing channel was functionally negative for the generation of adiponectin because channel blockade by antibodies, knock-down of TRPC1-TRPC5 in vitro, or conditional disruption of calcium permeability in TRPC5-incorporating channels in vivo increased the generation of adiponectin. The previously recognised capability of ?-linolenic acid to stimulate the generation of adiponectin was lost when calcium permeability in the channels was disrupted. Conclusions The data suggest that TRPC1 and TRPC5 contribute a constitutively-active heteromultimeric channel of adipocytes that negatively regulates adiponectin and through which ?-3 fatty acids enhance the anti-inflammatory adipokine, adiponectin. PMID:22668831

Sukumar, Piruthivi; Sedo, Alicia; Li, Jing; Wilson, Lesley A; O’Regan, David; Lippiat, Jonathan D; Porter, Karen E; Kearney, Mark T; Ainscough, Justin FX; Beech, David J

2012-01-01

153

The cAMP/PKA pathway rapidly activates SIRT1 to promote fatty acid oxidation independently of changes in NAD+  

PubMed Central

The NAD+-dependent deacetylase SIRT1 is an evolutionarily conserved metabolic sensor of the Sirtuin family that mediates homeostatic responses to certain physiological stresses such as nutrient restriction. Previous reports have implicated fluctuations in intracellular NAD+ concentrations as the principal regulator of SIRT1 activity. However, here we have identified a cAMP-induced phosphorylation of a highly conserved serine (S434) located in the SIRT1 catalytic domain that rapidly enhanced intrinsic deacetylase activity independently of changes in NAD+ levels. Attenuation of SIRT1 expression or the use of a non-phosphorylatable SIRT1 mutant prevented cAMP-mediated stimulation of fatty acid oxidation and gene expression linked to this pathway. Overexpression of SIRT1 in mice significantly potentiated the increases in fatty acid oxidation and energy expenditure caused by either pharmacological ?-adrenergic agonism or cold exposure. These studies support a mechanism of Sirtuin enzymatic control through the cAMP/PKA pathway with important implications for stress responses and maintenance of energy homeostasis. PMID:22195961

Gerhart-Hines, Zachary; Dominy, John E.; Blättler, Sharon M.; Jedrychowski, Mark P.; Banks, Alexander S.; Lim, Ji-Hong; Chim, Helen; Gygi, Steven P.; Puigserver, Pere

2012-01-01

154

Fatty Acid Composition and Antioxidant Activity of Tea (Camellia sinensis L.) Seed Oil Extracted by Optimized Supercritical Carbon Dioxide  

PubMed Central

Seeds are another product in addition to leaves (raw materials for teas) of tea (Camellia sinensis L.) plant. The great increase of tea consumption in recent years raises the challenge of finding commercial applications for tea seeds. In the present study, supercritical carbon dioxide (SC-CO2) extraction edible oil from tea seed was carried out, response surface methodology (RSM) was used to optimize processing parameters including time (20–90 min), temperature (35–45 °C) and pressure (50–90 MPa). The fatty acid composition and antioxidant activity of the extracted oil was also investigated. The highest yield of oil (29.2 ± 0.6%) was obtained under optimal SC-CO2 extraction conditions (45 °C, 89.7 min and 32 MPa, respectively), which was significantly higher (p < 0.05) than that (25.3 ± 1.0%) given by Soxhlet extraction. Meanwhile, tea seed oil extracted by SC-CO2 contained approximately 80% unsaturated fatty acids and showed a much stronger scavenging ability on the DPPH radical than that extracted by Soxhlet. SC-CO2 is a promising alternative for efficient extraction of edible oil from tea seed. Moreover, tea seed oil extracted by SC-CO2 is highly edible and has good antioxidant activity, and therefore may play a potential role as a health-promoting food resource in human diets. PMID:22174626

Wang, Yuefei; Sun, Da; Chen, Hao; Qian, Lisheng; Xu, Ping

2011-01-01

155

Catalyst-free fatty acid methyl ester production from wet activated sludge under subcritical water and methanol condition.  

PubMed

Wet activated sludge was converted directly into biodiesel using water as hydrolysis reagent to enhance the extraction of lipid in activated sludge, and as catalyst for the conversion of neutral lipids into biodiesel under subcritical conditions. At 175°C, 3.5MPa, a methanol to sludge ratio of 30 (mL/g) and a sludge water content of 84wt.%, about 90% conversion to fatty acid methyl esters was achieved within 24h without the need for conventional catalysts such as KOH and H(2)SO(4). Since water is employed as a catalyst, its removal is not required; therefore, the processing costs for producing biodiesel from activated sludge are reduced. The method has the potential for applications to other feedstock with high water contents such as micro-algae. PMID:22940307

Huynh, Lien Huong; Tran Nguyen, Phuong Lan; Ho, Quoc Phong; Ju, Yi-Hsu

2012-11-01

156

Comparison between plasma and erythrocyte fatty acid content as biomarkers of fatty acid intake in US women1-4  

Microsoft Academic Search

Background: Erythrocyte fatty acids may be superior to plasma fatty acids for reflecting long-term fatty acid intake because of less sensitivity to recent intake and a slower turnover rate. Objective: The objective was to compare the fatty acid content of erythrocytes with that of plasma with respect to their abilities to reflect usual fatty acid intake. Design: Fatty acids in

Qi Sun; Jing Ma; Hannia Campos; Susan E Hankinson; Frank B Hu

157

FXR activation improves myocardial fatty acid metabolism in a rodent model of obesity-driven cardiotoxicity  

Microsoft Academic Search

Background and aimsObesity-driven lipotoxicity is a risk factors for cardiovascular disease. The Farnesoid X Receptor (FXR) is a bile acids sensor and member of the nuclear receptor superfamily. Activation of FXR lowers plasma triacylglycerols and glucose levels through a mechanism that involves both the repression of key regulatory genes in the liver and the modulation of insulin sensitivity in peripheral

A. Mencarelli; S. Cipriani; B. Renga; C. D’Amore; G. Palladino; E. Distrutti; F. Baldelli; S. Fiorucci

158

A second generation of carbamate-based fatty acid amide hydrolase inhibitors with improved activity in vivo  

PubMed Central

The fatty acid ethanolamides are a class of signaling lipids that include agonists at cannabinoid and type-? peroxisome proliferator-activated receptors. In the brain, these compounds are primarily hydrolyzed by the intracellular serine enzyme fatty acid amide hydrolase (FAAH). O-aryl carbamate FAAH inhibitors such as URB597 are being evaluated clinically for the treatment of pain and anxiety, but interactions with carboxylesterases in liver might limit their usefulness. Here we explore two strategies aimed at overcoming this limitation. Lipophilic N-terminal substitutions, which enhance FAAH recognition, yield potent inhibitors but render such compounds both susceptible to attack by broad-spectrum hydrolases and inactive in vivo. By contrast, polar electron-donating O-aryl substituents, which decrease carbamate reactivity, yield compounds, such as URB694, that are highly potent FAAH inhibitors in vivo and less reactive with off-target carboxylesterases. The results suggest that an approach balancing inhibitor reactivity with target recognition produces FAAH inhibitors that display significantly improved drug-likeness. PMID:19637155

Clapper, Jason R.; Vacondio, Federica; King, Alvin R.; Duranti, Andrea; Tontini, Andrea; Silva, Claudia; Sanchini, Silvano; Tarzia, Giorgio; Mor, Marco; Piomelli, Daniele

2010-01-01

159

Phospholipid fatty acid composition and protein kinase C activity in the large intestine of rats fed on butter and coconut-oil diets.  

PubMed

Protein kinase C (PKC) has been proposed to play an important role in the aetiology of colon cancer. Therefore, we investigated whether the amount and type of saturated fat could affect colonic PKC activity by modifying either mucosal phospholipid fatty acid composition or faecal diacylglycerol production. Male Wistar rats (n 13 per group) were fed on diets containing butter or coconut oil at energy levels of 10% and 43% for 4 weeks. The control group received a low-fat diet providing 10% of energy from sunflowerseed oil. PKC activity was higher in the distal than the proximal colon but the quantity or type of fat did not alter PKC activity in either region of the colon. Saturated fats caused moderate changes in the fatty acid composition of caecal phospholipids, which were more obvious in the phosphatidylethanolamine than in the phosphatidylcholine fraction. A significant correlation was found between fatty acid composition of phosphatidylcholine and membrane PKC activity. In particular, there was a positive correlation between the proportion of saturated 14:0 and 18:0 and increased PKC activity while unsaturated 18:2n-6, 20:4n-6 and 16:1n-7 were inversely correlated with PKC activity. No relationship was found between phosphatidylethanolamine fatty acids and PKC activity. Concentration of faecal diacylglycerol was not affected by the diet. Overall the data suggest that diets high in saturated fat may not alter colonic PKC activity to a significant extent. PMID:10673914

Pajari, A M; Mutanen, M

1999-11-01

160

Animal fatty acid synthase: Functional mapping and cloning and expression of the domain I constituent?activities  

PubMed Central

Animal fatty acid synthase (FAS; EC 2.3.1.85) is a homodimer of a multifunctional subunit protein and catalyzes the synthesis of palmitate from acetyl-CoA, malonyl-CoA, and NADPH. The subunit (Mr ?270,000) carries seven distinct component activities and a site for the prosthetic group 4?-phosphopantetheine (acyl carrier protein). Based on proteolytic mapping, the organization of the activity domains along the subunit polypeptide from the N terminus is as follows: ?-ketoacyl synthase, acetyl and malonyl transacylases, ?-hydroxyacyl dehydratase, enoyl reductase, ?-ketoacyl reductase, acyl carrier protein, and thioesterase. By comparing the amino acid sequences of the chicken, rat, and human synthases, we found that kallikrein cleavage sites occur in the least conserved regions of the FAS polypeptide subunit. Determining the amino acid sequences of the N-terminal end of the major kallikrein cleavage peptides helped delineate the most likely boundaries of the component activities in the cDNA-derived amino acid sequence. To confirm this organization, we cloned the chicken FAS cDNA coding for domain I and expressed it in Escherichia coli as a maltose-binding fusion protein. The isolated recombinant protein contained the activities of the acetyl and malonyl transacylases and the ?-hydroxyacyl dehydratase. Based on the boundaries of the acetyl and malonyl transacylases and the ?-hydroxyacyl dehydratase, we also cloned the appropriate cDNA fragments encoding the domains that contain the transacylases and the dehydratase in pET vectors and expressed them in E. coli as thioredoxin-6xHis fusion proteins. The purified recombinant proteins contained, respectively, the activities of the acetyl and malonyl transacylases and the dehydratase. These results not only confirmed the order of the component activities in domain I, but also paved the way for successful expression and characterization of the remaining activities. PMID:9159116

Chirala, Subrahmanyam S.; Huang, Wei-Yong; Jayakumar, Arumugam; Sakai, Keiko; Wakil, Salih J.

1997-01-01

161

Activation and Repression of Epstein-Barr Virus and Kaposi's Sarcoma-Associated Herpesvirus Lytic Cycles by Short- and Medium-Chain Fatty Acids  

PubMed Central

ABSTRACT The lytic cycles of Epstein-Barr virus (EBV) and Kaposi's sarcoma-associated herpesvirus (KSHV) are induced in cell culture by sodium butyrate (NaB), a short-chain fatty acid (SCFA) histone deacetylase (HDAC) inhibitor. Valproic acid (VPA), another SCFA and an HDAC inhibitor, induces the lytic cycle of KSHV but blocks EBV lytic reactivation. To explore the hypothesis that structural differences between NaB and VPA account for their functional effects on the two related viruses, we investigated the capacity of 16 structurally related short- and medium-chain fatty acids to promote or prevent lytic cycle reactivation. SCFAs differentially affected EBV and KSHV reactivation. KSHV was reactivated by all SCFAs that are HDAC inhibitors, including phenylbutyrate. However, several fatty acid HDAC inhibitors, such as isobutyrate and phenylbutyrate, did not reactivate EBV. Reactivation of KSHV lytic transcripts could not be blocked completely by any fatty acid tested. In contrast, several medium-chain fatty acids inhibited lytic activation of EBV. Fatty acids that blocked EBV reactivation were more lipophilic than those that activated EBV. VPA blocked activation of the BZLF1 promoter by NaB but did not block the transcriptional function of ZEBRA. VPA also blocked activation of the DNA damage response that accompanies EBV lytic cycle activation. Properties of SCFAs in addition to their effects on chromatin are likely to explain activation or repression of EBV. We concluded that fatty acids stimulate the two related human gammaherpesviruses to enter the lytic cycle through different pathways. IMPORTANCE Lytic reactivation of EBV and KSHV is needed for persistence of these viruses and plays a role in carcinogenesis. Our direct comparison highlights the mechanistic differences in lytic reactivation between related human oncogenic gammaherpesviruses. Our findings have therapeutic implications, as fatty acids are found in the diet and produced by the human microbiota. Small-molecule inducers of the lytic cycle are desired for oncolytic therapy. Inhibition of viral reactivation, alternatively, may prove useful in cancer treatment. Overall, our findings contribute to the understanding of pathways that control the latent-to-lytic switch and identify naturally occurring molecules that may regulate this process. PMID:24807711

Gorres, Kelly L.; Daigle, Derek; Mohanram, Sudharshan

2014-01-01

162

Overproduction of fatty acids in engineered Saccharomyces cerevisiae.  

PubMed

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. PMID:24752690

Li, Xiaowei; Guo, Daoyi; Cheng, Yongbo; Zhu, Fayin; Deng, Zixin; Liu, Tiangang

2014-09-01

163

Sustained activation of PPAR? by endogenous ligands increases hepatic fatty acid oxidation and prevents obesity in ob/ob mice  

PubMed Central

Obesity, a major health concern, results from an imbalance between energy intake and expenditure. Leptin-deficient ob/ob mice are paradigmatic of obesity, resulting from excess energy intake and storage. Mice lacking acyl-CoA oxidase 1 (Acox1), the first enzyme of the peroxisomal fatty acid ?-oxidation system, are characterized by increased energy expenditure and a lean body phenotype caused by sustained activation of peroxisome proliferator-activated receptor ? (PPAR?) by endogenous ligands in liver that remain unmetabolized in the absence of Acox1. We generated ob/ob mice deficient in Acox1 (Acox1?/?) to determine how the activation of PPAR? by endogenous ligands might affect the obesity of ob/ob mice. In contrast to Acox1?/? (14.3±1.2 g at 6 mo) and the Acox1-deficient (ob/ob) double-mutant mice (23.8±4.6 g at 6 mo), the ob/ob mice are severely obese (54.3±3.2 g at 6 mo) and had significantly more (P<0.01) epididymal fat content. The resistance of Acox1?/?/ob/ob mice to obesity is due to increased PPAR?-mediated up-regulation of genes involved in fatty acid oxidation in liver. Activation of PPAR? in Acox1-deficient ob/ob mice also reduces serum glucose and insulin (P<0.05) and improves glucose tolerance and insulin sensitivity. Further, PPAR? activation reduces hepatic steatosis and increases hepatocellular regenerative response in Acox1?/?/ob/ob mice at a more accelerated pace than in mice lacking only Acox1. However, Acox1?/?/ob/ob mice manifest hepatic endoplasmic reticulum (ER) stress and also develop hepatocellular carcinomas (8 of 8 mice) similar to those observed in Acox1?/? mice (10 of 10 mice), but unlike in ob/ob (0 of 14 mice) and OB/OB (0 of 6 mice) mice, suggesting that superimposed ER stress and PPAR? activation contribute to carcinogenesis in a fatty liver. Finally, absence of Acox1 in ob/ob mice can impart resistance to high-fat diet (60% fat)-induced obesity, and their liver had significantly (P<0.01) more cell proliferation. These studies with Acox1?/?/ob/ob mice indicate that sustained activation of lipid-sensing nuclear receptor PPAR? attenuates obesity and restores glucose homeostasis by ameliorating insulin resistance but increases the risk for liver cancer development, in part related to excess energy combustion.—Huang, J., Jia, Y., Fu, T., Viswakarma, N., Bai, L., Sambasiva Rao, M., Zhu, Y., Borensztajn, J., Reddy, J. K. Sustained activation of PPAR? by endogenous ligands increases hepatic fatty acid oxidation and prevents obesity in ob/ob mice. PMID:22009939

Huang, Jiansheng; Jia, Yuzhi; Fu, Tao; Viswakarma, Navin; Bai, Liang; Rao, M. Sambasiva; Zhu, Yijun; Borensztajn, Jayme; Reddy, Janardan K.

2012-01-01

164

First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata  

PubMed Central

The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4-methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC50 = 165.5 ± 23.4 µM) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC50 = 62.3 ± 0.7 µM. PMID:21129369

Carballeira, Néstor M.; Montano, Nashbly; Cintrón, Gabriel A.; Márquez, Carmary; Rubio, Celia Fernández; Prada, Christopher Fernández; Balaña-Fouce, Rafael

2010-01-01

165

First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata.  

PubMed

The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4-methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC(50) = 165.5 ± 23.4 ?M) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC(50) = 62.3 ± 0.7 ?M. PMID:21129369

Carballeira, Néstor M; Montano, Nashbly; Cintrón, Gabriel A; Márquez, Carmary; Rubio, Celia Fernández; Prada, Christopher Fernández; Balaña-Fouce, Rafael

2011-02-01

166

Molecular recognition of nitrated fatty acids by PPAR[gamma  

SciTech Connect

Peroxisome proliferator activated receptor-{gamma} (PPAR{gamma}) regulates metabolic homeostasis and adipocyte differentiation, and it is activated by oxidized and nitrated fatty acids. Here we report the crystal structure of the PPAR{gamma} ligand binding domain bound to nitrated linoleic acid, a potent endogenous ligand of PPAR{gamma}. Structural and functional studies of receptor-ligand interactions reveal the molecular basis of PPAR{gamma} discrimination of various naturally occurring fatty acid derivatives.

Li, Yong; Zhang, Jifeng; Schopfer, Francisco J.; Martynowski, Dariusz; Garcia-Barrio, Minerva T.; Kovach, Amanda; Suino-Powell, Kelly; Baker, Paul R.S.; Freeman, Bruce A.; Chen, Y. Eugene; Xu, H. Eric (Pitt); (Michigan); (Van Andel); (Morehouse-MED)

2010-03-08

167

Fatty acid hydroxytyrosyl esters: structure/antioxidant activity relationship by ABTS and in cell-culture DCF assays.  

PubMed

A large series of hydroxytyrosyl esters of C2-C18 fatty acids with increasing lipophilicity was prepared by a new highly efficient method based on acylation of methylorthoformate-protected hydroxytyrosol. All products were tested for relative antioxidant effect using ABTS assays in ethanolic medium and DCF assays in L6 cells. No linear correlation between lipophilicity and antioxidant effect was found. ABTS assays showed a growing antioxidant capacity, with respect to hydroxytyrosol, only for medium-sized ester chains (C4-C10) and a nearly constant capacity for the higher homologues. This has been rationalized by molecular dynamics experiments in terms of partial shielding of the catecholic hydroxyls by long-chain esters. A similar and dose-dependent pattern was observed in DCF assays in L6 cells, but a sharp antioxidant activity drop resulted for long-chain esters, probably due to membrane entrapment. PMID:20397651

Tofani, Daniela; Balducci, Valentina; Gasperi, Tecla; Incerpi, Sandra; Gambacorta, Augusto

2010-05-12

168

The Burkholderia cenocepacia BDSF Quorum Sensing Fatty Acid is Synthesized by a Bifunctional Crotonase Homologue Having Both Dehydratase and Thioesterase Activities  

PubMed Central

Summary Signal molecules of the Diffusible Signal Factor (DSF) family have been shown recently to be involved in regulation of pathogenesis and biofilm formation in diverse Gram-negative bacteria. DSF signals are reported to be active not only on their cognate bacteria, but also on unrelated bacteria and the pathogenic yeast, Candida albicans. DSFs are monounsaturated fatty acids of medium chain length containing an unusual cis-2 double bond. Although genetic analyses had identified genes involved in DSF synthesis, the pathway of DSF synthesis was unknown. The DSF of the important human pathogen Burkholderia cenocepacia (called BDSF) is cis-2-dodecenoic acid. We report that BDSF is synthesized from a fatty acid synthetic intermediate, the acyl carrier protein (ACP) thioester of 3-hydroxydodecanoic acid. This intermediate is intercepted by protein Bcam0581 and converted to cis-2-dodecenoyl-ACP. Bcam0581 is annotated as a homologue of crotonase, the first enzyme of the fatty acid degradation pathway. We demonstrated Bcam0581to be a bifunctional protein that not only catalyzed dehydration of 3-hydroxydodecanoyl-ACP to cis-2-dodecenoyl-ACP, but also cleaved the thioester bond to give the free acid. Both activities required the same set of active site residues. Although dehydratase and thioesterase activities are known activities of the crotonase superfamily, Bcam0581 is the first protein shown to have both activities. PMID:22221091

Bi, Hongkai; Christensen, Quin H.; Feng, Youjun; Wang, Haihong; Cronan, John E.

2012-01-01

169

Effect of thymol and carvacrol feed supplementation on performance, antioxidant enzyme activities, fatty acid composition, digestive enzyme activities, and immune response in broiler chickens.  

PubMed

This trial was conducted to evaluate the effects of dietary supplementation of phytogenic product containing an equal mixture of thymol and carvacrol at 4 levels (0, 60, 100, and 200 mg/kg of diet) on performance, antioxidant enzyme activities, fatty acid composition, digestive enzyme activities, and immune response in broiler chickens. Each of the 4 diets was fed to 5 replicates of 12 chicks each from d 0 to 42. The inclusion of thymol + carvacrol linearly decreased (P < 0.05) feed intake, but the highest (P < 0.05) BW gain (ADG) and feed efficiency was observed in broilers offered 200 mg/kg of phytogenic product. The phytogenic product linearly increased (P < 0.05) superoxide dismutase and glutathione peroxidase activities and decreased (P < 0.05) malondialdehyde level in thigh muscle at d 42 and serum and liver at d 24 and 42. Total saturated fatty acids were depressed (P < 0.05) and total polyunsaturated fatty acid and n-6 were linearly increased (P < 0.05) in serum and thigh by the inclusion of phytogenic product compared with the control diet. Supplementation with thymol + carvacrol also increased intestinal and pancreatic trypsin, lipase, and protease activities in 24-d-old (linear, P < 0.05) but not in 42-d-old birds. Thymol + carvacrol modified (linear, P < 0.05) immune response by increasing hypersensitivity response, total and IgG anti-sheep red blood cell titers, and decreasing heterophil to lymphocyte ratio compared with the control group. However, hematological parameters and lymphoid organ weight were not affected by thymol + carvacrol. Thus, feed supplementation with thymol + carvacrol enhanced performance, increased antioxidant enzyme activities, retarded lipid oxidation, enhanced digestive enzyme activities, and improved immune response of broilers. PMID:23873553

Hashemipour, H; Kermanshahi, H; Golian, A; Veldkamp, T

2013-08-01

170

RESEARCH PAPER Contribution of omega-3 fatty acid desaturase and  

E-print Network

RESEARCH PAPER Contribution of omega-3 fatty acid desaturase and 3-ketoacyl-ACP synthase II (KASII: Cold acclimation, fatty acid, freezing resistance, linoleic acid, low temperature, omega-3 fatty acid

Palva, Tapio

171

Fatty acids of Pinus elliottii tissues.  

NASA Technical Reports Server (NTRS)

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.

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

1973-01-01

172

Addition of an N-terminal epitope tag significantly increases the activity of plant fatty acid desaturases expressed in yeast cells  

Technology Transfer Automated Retrieval System (TEKTRAN)

Saccharomyces cerevisiae shows great potential for development of bioreactor systems geared towards the production of high-value lipids such as polyunsaturated omega-3 fatty acids, the yields of which are largely dependent on the activity of ectopically-expressed enzymes. Here we show that the addit...

173

The fatty acid signaling molecule cis-2-decenoic acid increases metabolic activity and reverts persister cells to an antimicrobial-susceptible state.  

PubMed

Persister cells, which are tolerant to antimicrobials, contribute to biofilm recalcitrance to therapeutic agents. In turn, the ability to kill persister cells is believed to significantly improve efforts in eradicating biofilm-related, chronic infections. While much research has focused on elucidating the mechanism(s) by which persister cells form, little is known about the mechanism or factors that enable persister cells to revert to an active and susceptible state. Here, we demonstrate that cis-2-decenoic acid (cis-DA), a fatty acid signaling molecule, is able to change the status of Pseudomonas aeruginosa and Escherichia coli persister cells from a dormant to a metabolically active state without an increase in cell number. This cell awakening is supported by an increase of the persister cells' respiratory activity together with changes in protein abundance and increases of the transcript expression levels of several metabolic markers, including acpP, 16S rRNA, atpH, and ppx. Given that most antimicrobials target actively growing cells, we also explored the effect of cis-DA on enhancing antibiotic efficacy in killing persister cells due to their inability to keep a persister cell state. Compared to antimicrobial treatment alone, combinational treatments of persister cell subpopulations with antimicrobials and cis-DA resulted in a significantly greater decrease in cell viability. In addition, the presence of cis-DA led to a decrease in the number of persister cells isolated. We thus demonstrate the ability of a fatty acid signaling molecule to revert bacterial cells from a tolerant phenotype to a metabolically active, antimicrobial-sensitive state. PMID:25192989

Marques, Cláudia N H; Morozov, Aleksey; Planzos, Penny; Zelaya, Hector M

2014-11-01

174

Non-Alcoholic Fatty Liver Disease: The Bile Acid-Activated Farnesoid X Receptor as an Emerging Treatment Target  

PubMed Central

Non-alcoholic fatty liver disease (NAFLD) is currently evolving as the most common liver disease worldwide. It may progress to liver cirrhosis and liver cancer and is poised to represent the most common indication for liver transplantation in the near future. The pathogenesis of NAFLD is multifactorial and not fully understood, but it represents an insulin resistance state characterized by a cluster of cardiovascular risk factors including obesity, dyslipidemia, hyperglycemia, and hypertension. Importantly, NAFLD also has evolved as independent risk factor for cardiovascular disease. Unfortunately thus far no established treatment does exist for NAFLD. The bile acid-activated nuclear farnesoid X receptor (FXR) has been shown to play a role not only in bile acid but also in lipid and glucose homeostasis. Specific targeting of FXR may be an elegant and very effective way to readjust dysregulated nuclear receptor-mediated metabolic pathways. This review discusses the body's complex response to the activation of FXR with its beneficial actions but also potential undesirable side effects. PMID:22187656

Fuchs, Michael

2012-01-01

175

Trienoic Fatty Acids and Plant Tolerance of High Temperature  

Microsoft Academic Search

The chloroplast membrane of higher plants contains an unusually high concentration of trienoic fatty acids. Plants grown in colder temperatures have a higher content of trienoic fatty acids. Transgenic tobacco plants in which the gene encoding chloroplast omega-3 fatty acid desaturase, which synthesizes trienoic fatty acids, was silenced contained a lower level of trienoic fatty acids than wild-type plants and

Yuuki Murakami; Michito Tsuyama; Yoshichika Kobayashi; Hiroaki Kodama; Koh Iba

2000-01-01

176

Enhanced biological phosphorus removal driven by short-chain fatty acids produced from waste activated sludge alkaline fermentation.  

PubMed

This paper examines the feasibility of using alkaline fermentative short-chain fatty acids (SCFAs) as the carbon sources of enhanced biological phosphorus removal (EBPR) microorganisms. First, the released phosphorus was recovered from the SCFA-containing alkaline fermentation liquid by the formation of struvite precipitation, and 92.8% of the soluble ortho-phosphorus (SOP) could be recovered under conditions of Mg/P = 1.8 (mol/mol), pH 10.0, and a reaction time of 2 min. One reason for a Mg addition required in this study that was higher than the theoretical value was thatthe organic compounds consumed Mg. Then, two sequencing batch reactors (SBRs) were operated, respectively, with acetic acid and alkaline fermentative SCFAs as the carbon source of EBPR. The transformations of SOP, polyhydroxyalkanoates (PHAs), and glycogen and the removal of phosphorus were compared between two SBRs. It was observed that the phosphorus removal efficiency was around 98% with the fermentative SCFAs, and about 71% with acetic acid, although the former showed much lower transformations of both PHAs and glycogen. The reasons that fermentative SCFAs caused much higher SOP removal than acetic acid were due to less PHAs used for glycogen synthesis and a higher PHA utilization efficiency for SOP uptake. Finally, the toxicity of fermentation liquid to EBPR microorganisms was examined, and no inhibitory effect was observed. It can be concluded from this studythatthe SCFAs from alkaline fermentation of waste activated sludge were a superior carbon source for EBPR microorganisms than pure acetic acid. PMID:17993158

Tong, Juan; Chen, Yinguang

2007-10-15

177

Volatile fatty acid concentrations, enzyme activities and microflora in the rumen contents of heifers during transition to pasture.  

PubMed

Observations were carried out on volatile fatty acid (VFA) concentrations, enzyme activities and the microflora of the rumen contents in heifers during transition from winter to pasture feeding and in the subsequent gazing cycles. After turn-out to pasture, total VFA concentrations in the rumen contents of heifers significantly decreased from 107.7 to 88.7 mmol.l-1 (P < 0.01). After subsequent increase the total VFA concentrations reached their highest value (117.0 mmol.l-1) in the 8th week of grazing. The proportion of the molar acetic acid concentration in the rumen content increased insignificantly whereas that of propionic acid decreased insignificantly. In the molar proportion of butyric acid no significant differences could be stated. In the subsequent weeks the molar proportions of acetic acid were rather balanced and ranged within 66.2 and 68.0 mol%; the molar proportion of propionic acid insignificantly increased in the 4th week (18.7 mol%). Molar proportions of butyric acid on pasture insignificantly increased in week 3 (15.2 mol%) and appeared as balanced, later acquiring values between 14.0 and 14.8 mol%. The energetic yield of VFA production in the rumen of heifers decreased insignificantly from 73.6 to 72.15; the acetate: propionate ratio revealed an insignificant increase from 3.66 to 4.18. The enzyme activity of cellulase (endoglucanase E.C.3.2.1.4 and cellobiohydrolase E.C.3.2.1.91.) decreased significantly from 17.83 to 16.64 micrograms.ml-1 (P < 0.01); in the subsequent weeks, however, a significant increase could be observed. The enzyme activity of alpha-amylase (E.C.3.2.1.1.) decreased significantly (P < 0.05). In the 4th week a significant increase of the former occurred. The numbers of cellulolytic bacteria in the rumen content decreased significantly from 8.08 to 7.61 log 10.ml-1 (P < 0.01) and then a significant increase to 8.39 log 10.ml-1 was observed again in the 3rd week of grazing (P < 0.05). During pasture, a significant increase of the numbers of lactate-utilizing bacteria was recorded. As to the numbers of lactobacilli a significant decrease (P < 0.05) with a subsequent insignificant increase during grazing could be observed. Throughout the grazing season, the numbers of Streptococci reached values that surpassed those recorded during the winter feeding period. After transition from winter feeding to pasture the adaptation of rumen fermentation took four weeks. PMID:7733812

Zitnan, R; Sommer, A; Gallo, J; Lauková, A; Bomba, A; Venglovský, J

1994-01-01

178

[Innovations in the medical treatment of gallstones and fatty liver: FABACs (Fatty Acid Bile Acid Conjugates)].  

PubMed

Gallstones and fatty liver are common disorders in the Western world, largely due to dietary and life style factors. Currently, laparoscopic cholecystectomy is the main treatment option for gallbladder stones. Surgery is, however, expensive and may cause morbidity and even mortality. An effective medical treatment would be desirable, especially in patients with mild to moderate symptoms or high surgical risk. Currently, the bile acid UDCA (Ursodeoxycholic acid) is used for oral dissolution treatment and for the prevention of cholelithiasis in selected cases. However, the major limitations of this treatment are its low efficacy, slow action and stone recurrence. Recently, phospholipids rather than bile salts were realized to be the major natural cholesterol solubilizers in bile. They also possess anti-crystallizing activity. The sn-2 fatty acid of the phospholipids molecule was found to be particularly important. This was the background for the development of FABACs (Fatty Acid and Bile Acid Conjugates), which are novel synthetic lipid molecules. These molecules are composed of fatty acids (with chain lengths from C-14 to C-22), that are linked to cholic acid, by an amide bond at position 3. In vitro and in vivo studies (in mice) have shown that FABACs can prevent the formation of cholesterol crystals and dissolve existing ones. C20-FABAC, when given orally, is absorbed and secreted into bile. It was also found to have a series of beneficial effects on cholesterol metabolism. The main treatment for patients with fatty liver consists of lifestyle and diet modifications, which are associated with low compliance. Currently there is no effective medical treatment for this disease. In the FABAC studies on the prevention and dissolution of gallstones in laboratory animals, it was observed that this treatment also prevents the formation of diet induced fatty liver. Further prospective studies found that FABACs indeed prevent/decrease the formation of fatty liver induced by high fat diet. This influence was observed in all the fatty liver parameters (histology as well as chemical analysis), and in different animal strains. Based on these findings, FABACs seem to be good candidates for the medical treatment of hepatobiliary disorders, in particular gallstones and fatty liver disease. PMID:18686819

Keizman, Daniel; Goldiner, Ilana; Leikin-Frenkel, Alicia; Konikoff, Fred M

2008-04-01

179

Nordihydroguaiaretic acid protects against high-fat diet-induced fatty liver by activating AMP-activated protein kinase in obese mice  

SciTech Connect

Research highlights: {yields} NDGA decreases high-fat diet-induced body weight gain and adiposity. {yields} NDGA reduces high-fat diet-induced triglyceride accumulation in liver. {yields} NDGA improves lipid storage in vitro through altering lipid regulatory proteins. {yields} Inhibition of lipid storage in vivo and in vitro is mediated by AMPK activation. -- Abstract: Nonalcoholic fatty liver disease, one of the most common causes of chronic liver disease, is strongly associated with metabolic syndrome. Nordihydroguaiaretic acid (NDGA) has been reported to inhibit lipoprotein lipase; however, the effect of NDGA on hepatic lipid metabolism remains unclear. We evaluated body weight, adiposity, liver histology, and hepatic triglyceride content in high-fat diet (HFD)-fed C57BL/6J mice treated with NDGA. In addition, we characterized the underlying mechanism of NDGA's effects in HepG2 hepatocytes by Western blot and RT-PCR analysis. NDGA (100 or 200 mg/kg/day) reduced weight gain, fat pad mass, and hepatic triglyceride accumulation, and improved serum lipid parameters in mice fed a HFD for 8 weeks. NDGA significantly increased AMP-activated protein kinase (AMPK) phosphorylation in the liver and in HepG2 hepatocytes. NDGA downregulated the level of mature SREBP-1 and its target genes (acetyl-CoA carboxylase and fatty acid synthase), but, it upregulated expression of genes involved in fatty acid oxidation, such as peroxisome proliferator-activated receptor (PPAR){alpha}, PPAR{gamma} coactivator-1, carnitine palmitoyl transferase-1, and uncoupling protein-2. The specific AMPK inhibitor compound C attenuated the effects of NDGA on expression of lipid metabolism-related proteins in HepG2 hepatocytes. The beneficial effects of NDGA on HFD-induced hepatic triglyceride accumulation are mediated through AMPK signaling pathways, suggesting a potential target for preventing NAFLD.

Lee, Myoung-Su; Kim, Daeyoung; Jo, Keunae [Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul 120-749 (Korea, Republic of)] [Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul 120-749 (Korea, Republic of); Hwang, Jae-Kwan, E-mail: jkhwang@yonsei.ac.kr [Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul 120-749 (Korea, Republic of) [Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul 120-749 (Korea, Republic of); Translational Research Center for Protein Function Control, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul 120-749 (Korea, Republic of)

2010-10-08

180

Omega-3 fatty acids in Hawaii seafood.  

PubMed

Omega-3 fatty acids, the most potent of which are found in seafood, are of interest because of their effects on cardiovascular and inflammatory diseases and their possible effects on cancer. However, consumers in Hawaii wishing to increase their dietary omega-3 to omega-6 fatty acid ratio are faced with the difficulty that several types of seafood popular in Hawaii and aquacultured seafood new in the marketplace have unknown omega-3 fatty acid levels. The purpose of this work is to determine omega-3 fatty acid levels of selected seafood and fish oil capsules. Several seafoods and some over-the-counter fish oil capsules were sampled and analyzed. Aku eggs, aquacultured hamachi (yellowtail jack from Japan), one sample of turbot, and EPA Plus, Promega, and Omega-3 Super EPA capsules were found to contain high levels of omega-3 fatty acids. Levels were comparable to those in the fatty fishes such as salmon and mackerel. Butterfish, mahimahi eggs; other fish oil capsules (ProEPA and Omega 3) contained moderate levels of omega-3 fatty acids. Fish cakes, seaweed, several lean fishes, and cod liver oil capsules had small quantities of omega-3 fatty acids. It appeared that the omega-3 fatty acid content of aquacultured species studied was significantly higher than in wild caught species. There was a substantial difference between claimed and actual omega-3 fatty acid levels in commercially available fish oil capsules. These findings can help consumers when selecting types of seafood for their diet that are good sources of omega-3 fatty acids. PMID:8050896

Ako, H; Ota, E; Ogasawara, A

1994-05-01

181

Omega-3 polyunsaturated fatty acids selectively inhibit growth in neoplastic oral keratinocytes by differentially activating ERK1/2  

PubMed Central

The long-chain omega-3 polyunsaturated fatty acids (n-3 PUFAs)—eicosapentaenoic acid (EPA) and its metabolite docosahexaenoic acid (DHA)—inhibit cancer formation in vivo, but their mechanism of action is unclear. Extracellular signal-regulated kinase 1/2 (ERK1/2) activation and inhibition have both been associated with the induction of tumour cell apoptosis by n-3 PUFAs. We show here that low doses of EPA, in particular, inhibited the growth of premalignant and malignant keratinocytes more than the growth of normal counterparts by a combination of cell cycle arrest and apoptosis. The growth inhibition of the oral squamous cell carcinoma (SCC) lines, but not normal keratinocytes, by both n-3 PUFAs was associated with epidermal growth factor receptor (EGFR) autophosphorylation, a sustained phosphorylation of ERK1/2 and its downstream target p90RSK but not with phosphorylation of the PI3 kinase target Akt. Inhibition of EGFR with either the EGFR kinase inhibitor AG1478 or an EGFR-blocking antibody inhibited ERK1/2 phosphorylation, and the blocking antibody partially antagonized growth inhibition by EPA but not by DHA. DHA generated more reactive oxygen species and activated more c-jun N-terminal kinase than EPA, potentially explaining its increased toxicity to normal keratinocytes. Our results show that, in part, EPA specifically inhibits SCC growth and development by creating a sustained signalling imbalance to amplify the EGFR/ERK/p90RSK pathway in neoplastic keratinocytes to a supraoptimal level, supporting the chemopreventive potential of EPA, whose toxicity to normal cells might be reduced further by blocking its metabolism to DHA. Furthermore, ERK1/2 phosphorylation may have potential as a biomarker of n-3 PUFA function in vivo. PMID:23892603

Parkinson, Eric Kenneth

2013-01-01

182

Postpartum ovarian activity in multiparous Holstein cows treated with bovine somatotropin and fed n-3 fatty acids in early lactation.  

PubMed

Multiparous cows (n = 59) were blocked by expected calving date and previous 305-d mature-equivalent milk yield and assigned randomly to a 2 x 2 factorial design to determine the effects of bovine somatotropin (bST; Posilac, Monsanto Animal Agricultural Group, St. Louis, MO) and dietary fat on ovarian activity during the first 90 d in milk (DIM). Diets that included whole, high-oil sunflower seeds [SS; 10% of dietary dry matter; rich in linoleic acid (18:2)] or a mixture of Alifet-High Energy and Alifet-Repro [AF; Alifet USA, Cincinnati, OH; 3.5 and 1.5% of dietary dry matter, respectively; protected source of linolenic (18:3), eicosapentaenoic, and docosahexaenoic fatty acids] were provided from calving. Diets were isocaloric at equal intakes, but AF provided more net energy for lactation at actual intakes (1.54 vs. 1.66 Mcal/kg of dry matter). Cows received 0 or 500 mg of bST (N, Y) every 10 d from 12 to 70 DIM and at 14-d intervals from 70 to 280 DIM. Breeding was initiated after 90 DIM. Follicular dynamics, luteal growth and development (15 to 90 DIM), and plasma progesterone concentrations (1 to 90 DIM) were evaluated (3 times per week). Days to first ovulation (33.6 +/- 1.4) and incidence of anovulation at 45 or 70 DIM did not differ among treatments. Interovulatory intervals were similar among treatments (22.1 +/- 0.9 d). Incidence of estrous cycles with 2 follicular waves was greater for SSY (71.0%) and AFN (80.0%) than for other groups, but more 3-wave cycles occurred with AFY (83.3%). Growth rate of the ovulatory follicle was greater for AF than SS (1.9 vs. 2.2 +/- 0.11 mm/d) and diameter of ovulatory follicles was larger for AFN than the other treatments (17.9 vs. 15.7 +/- 0.7 mm). Area under the progesterone curve was reduced for SSY (63.2, 48.1, 55.5, and 61.4 +/- 5.1 ng.d/mL for SSN, SSY, AFN, and AFY, respectively). The number of class 1 (3 to 5 mm) follicles was decreased and the number of class 2 (6 to 9 mm) follicles was increased by bST. The number of class 2 follicles was reduced by AF. Initiation of bST administration at 12 DIM and dietary n-3 fatty acids altered ovarian activity during the first 90 DIM and could benefit reproductive performance. Dietary n-3 fatty acids interacted with bST administration in early lactation to increase the incidence of estrous cycles with 3 follicular waves. Although these changes could benefit reproductive performance, evaluation with a larger number of cows is needed to determine if these alterations improve fertility. PMID:19762803

Carriquiry, M; Dahlen, C R; Weber, W J; Lamb, G C; Crooker, B A

2009-10-01

183

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2010 CFR

...Triethanolamine salts of fatty acids. 721.3629 Section 721...Triethanolamine salts of fatty acids. (a) Chemical substances...triethanolamine salts of fatty acids (PMN Nos. P-92-156...processed, or used in the employer's workplace, the employer...

2010-07-01

184

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2011 CFR

...Triethanolamine salts of fatty acids. 721.3629 Section 721...Triethanolamine salts of fatty acids. (a) Chemical substances...triethanolamine salts of fatty acids (PMN Nos. P-92-156...processed, or used in the employer's workplace, the employer...

2011-07-01

185

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2012 CFR

...2012-07-01 false Triethanolamine salts of fatty acids. 721.3629 Section...Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances...identified generically as triethanolamine salts of fatty acids (PMN Nos....

2012-07-01

186

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2013 CFR

...2013-07-01 false Triethanolamine salts of fatty acids. 721.3629 Section...Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances...identified generically as triethanolamine salts of fatty acids (PMN Nos....

2013-07-01

187

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2014 CFR

...2014-07-01 false Triethanolamine salts of fatty acids. 721.3629 Section...Substances § 721.3629 Triethanolamine salts of fatty acids. (a) Chemical substances...identified generically as triethanolamine salts of fatty acids (PMN Nos....

2014-07-01

188

The human liver fatty acid binding protein (FABP1) gene is activated by FOXA1 and PPAR?; and repressed by C/EBP?: Implications in FABP1 down-regulation in nonalcoholic fatty liver disease.  

PubMed

Liver fatty acid binding protein (FABP1) prevents lipotoxicity of free fatty acids and regulates fatty acid trafficking and partition. Our objective is to investigate the transcription factors controlling the human FABP1 gene and their regulation in nonalcoholic fatty liver disease (NAFLD). Adenovirus-mediated expression of multiple transcription factors in HepG2 cells and cultured human hepatocytes demonstrated that FOXA1 and PPAR? are among the most effective activators of human FABP1, whereas C/EBP? is a major dominant repressor. Moreover, FOXA1 and PPAR? induced re-distribution of FABP1 protein and increased cytoplasmic expression. Reporter assays demonstrated that the major basal activity of the human FABP1 promoter locates between -96 and -229bp, where C/EBP? binds to a composite DR1-C/EBP element. Mutation of this element at -123bp diminished basal reporter activity, abolished repression by C/EBP? and reduced transactivation by HNF4?. Moreover, HNF4? gene silencing by shRNA in HepG2 cells caused a significant down-regulation of FABP1 mRNA expression. FOXA1 activated the FABP1 promoter through binding to a cluster of elements between -229 and -592bp, whereas PPAR? operated through a conserved proximal element at -59bp. Finally, FABP1, FOXA1 and PPAR? were concomitantly repressed in animal models of NAFLD and in human nonalcoholic fatty livers, whereas C/EBP? was induced or did not change. We conclude that human FABP1 has a complex mechanism of regulation where C/EBP? displaces HNF4? and hampers activation by FOXA1 and PPAR?. Alteration of expression of these transcription factors in NAFLD leads to FABP1 gen repression and could exacerbate lipotoxicity and disease progression. PMID:23318274

Guzmán, Carla; Benet, Marta; Pisonero-Vaquero, Sandra; Moya, Marta; García-Mediavilla, M Victoria; Martínez-Chantar, M Luz; González-Gallego, Javier; Castell, José Vicente; Sánchez-Campos, Sonia; Jover, Ramiro

2013-04-01

189

Polyunsaturated fatty acids and insulin resistance  

Technology Transfer Automated Retrieval System (TEKTRAN)

We have reviewed results from published studies regarding the effects of polyunsaturated fatty acids (PUFA) intake on insulin resistance (IR) in human subjects. Evidence has been gathered from epidemiological, cross-sectional and interventions studies. Increased intake of trans fatty acids (TFA) inc...

190

A new anxiolytic fatty acid from Aethusa cynapium.  

PubMed

The present investigation was carried out with a view to separate bioactive constituent from Aethusa cynapium. Bioactivity guided fractionation of the anxiolytic methanol extract has led to the isolation of a novel unsaturated fatty acid. Structure of the acid characterized by UV, IR, 1H NMR, C13 NMR, MS techniques was found to be trideca-7, 9, 11-trienoic acid. Antianxiety activity was confirmed using the mCPP-induced hypolocomotion test. This new fatty acid-trideca-7,9,11-trienoic acid, isolated from A. cynapium was found to be responsible for the antianxiety activity of the plant. PMID:20603195

Shri, Richa; Bhutani, K K; Sharma, Anupam

2010-12-01

191

Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer  

PubMed Central

Epoxygenated fatty acids (EpFAs), which are lipid mediators produced by cytochrome P450 epoxygenases from polyunsaturated fatty acids, are important signaling molecules known to regulate various biological processes including inflammation, pain and angiogenesis. The EpFAs are further metabolized by soluble epoxide hydrolase (sEH) to form fatty acid diols which are usually less-active. Pharmacological inhibitors of sEH that stabilize endogenous EpFAs are being considered for human clinical uses. Here we review the biology of ?-3 and ?-6 EpFAs on inflammation, pain, angiogenesis and tumorigenesis. PMID:24345640

Zhang, Guodong; Kodani, Sean; Hammock, Bruce D.

2014-01-01

192

Fatty acid content of marine oil capsules  

Microsoft Academic Search

The use of dietary ?3 fatty acid capsules has been associated with a decrease in plasma triglyceride levels. In addition,\\u000a populations consuming diets rich in fish appear to have a decreased incidence of cardiovascular disease. Eicosapentaenoic\\u000a acid (EPA, 20?5?3) and docosahexaenoic acid (DHA, 22?6?3) are major fatty acids in fish oils. It is believed that fish oils\\u000a exert their biolotic

Kew M. Chee; Jun Xian Gong; Deirdre M. Good Rees; Mohsen Meydanl; Lynne Ausman; Julia Johnson; Edward N. Siguel; Ernst J. Schaefer

1990-01-01

193

Nitro-fatty acids and cyclopentenone prostaglandins share strategies to activate the Keap1-Nrf2 system: a study using green fluorescent protein transgenic zebrafish  

PubMed Central

Nitro-fatty acids are electrophilic fatty acids produced in vivo from nitrogen peroxide that have many physiological activities. We recently demonstrated that nitro-fatty acids activate the Keap1-Nrf2 system, which protects cells from damage owing to electrophilic or oxidative stresses via transactivating an array of cytoprotective genes, although the molecular mechanism how they activate Nrf2 is unclear. A number of chemical compounds with different structures have been reported to activate the Keap1-Nrf2 system, which can be categorized into at least six classes based on their sensing pathways. In this study, we showed that nitrooleic acid (OA-NO2), one of major nitro-fatty acids, activates Nrf2 in the same manner that of a cyclopentenone prostaglandin 15-deoxy-?12,14-prostaglandin J2 (15d-PGJ2) using transgenic zebrafish that expresses green fluorescent protein (GFP) in response to Nrf2 activators. In transgenic embryos, GFP was induced in the whole body by treatment with OA-NO2, 15d-PGJ2 or diethylmaleate (DEM), but not with hydrogen peroxide (H2O2), when exogenous Nrf2 and Keap1 were co-overexpressed. Induction by OA-NO2 or 15d-PGJ2 but not DEM was observed, even when a C151S mutation was introduced in Keap1. Our results support the contention that OA-NO2 and 15d-PGJ2 share an analogous cysteine code as electrophiles and also have similar anti-inflammatory roles. PMID:21143560

Tsujita, Tadayuki; Li, Li; Nakajima, Hitomi; Iwamoto, Noriko; Nakajima-Takagi, Yaeko; Ohashi, Ken; Kawakami, Koichi; Kumagai, Yoshito; Freeman, Bruce A.; Yamamoto, Masayuki; Kobayashi, Makoto

2014-01-01

194

8, 687725, 2008 Effect of fatty acids  

E-print Network

Chemistry and Physics Discussions The effect of fatty acid surfactants on the uptake of nitric acid on the uptake of nitric acid (HNO3), an important removal reaction of nitrogen oxides in the marine boundary acid films and of water soluble organic25 aerosol constituents on the uptake of atmospheric nitric acid

Paris-Sud XI, Université de

195

Photocatalytic antibacterial activity of nano-TiO2 (anatase)-based thin films: Effects on Escherichia coli cells and fatty acids.  

PubMed

Titanium dioxide is a photocatalyst with well-known ability to oxidise a wide range of organic contaminants as well as to destroy microbial cells. In the present work TiO2 nanoparticles with high specific surface area (150m(2)/g) were used to prepare nanostructured films. The TiO2 nanoparticle-based film in combination with UV-A illumination with intensity (22W/m(2)) comparable to that of the sunlight in the UV-A region was used to demonstrate light-induced antibacterial effects. Fast and effective inactivation of Escherichia coli cells on the prepared thin films was observed. Visualization of bacterial cells under scanning electron microscopy (SEM) showed enlargement of the cells, distortion of cellular membrane and possible leakage of cytoplasm after 10min of exposure to photoactivated TiO2. According to the plate counts there were no viable cells as early as after 20min of exposure to UV-A activated TiO2. In parallel to effects on bacterial cell viability and morphology, changes in saturated and unsaturated fatty acids - important components of bacterial cell membrane-were studied. Fast decomposition of saturated fatty acids and changes in chemical structure of unsaturated fatty acids were detected. Thus, we suggest that peroxidation and decomposition of membrane fatty acids could be one of the factors contributing to the morphological changes of bacteria observed under SEM, and ultimately, cell death. PMID:25545332

Joost, Urmas; Juganson, Katre; Visnapuu, Meeri; Mortimer, Monika; Kahru, Anne; Nõmmiste, Ergo; Joost, Urmeli; Kisand, Vambola; Ivask, Angela

2015-01-01

196

Fatty acid metabolism in the perfused rat liver  

PubMed Central

1. The formation of acetoacetate, ?-hydroxybutyrate and glucose was measured in the isolated perfused rat liver after addition of fatty acids. 2. The rates of ketone-body formation from ten fatty acids were approximately equal and independent of chain length (90–132?mol/h per g), with the exception of pentanoate, which reacted at one-third of this rate. The [?-hydroxybutyrate]/[acetoacetate] ratio in the perfusion medium was increased by long-chain fatty acids. 3. Glucose was formed from all odd-numbered fatty acids tested. 4. The rate of ketone-body formation in the livers of rats kept on a high-fat diet was up to 50% higher than in the livers of rats starved for 48h. In the livers of fat-fed rats almost all the O2 consumed was accounted for by the formation of ketone bodies. 5. The ketone-body concentration in the blood of fat-fed rats rose to 4–5mm and the [?-hydroxybutyrate]/[acetoacetate] ratio rose to 11.5. 6. When the activity of the microsomal mixed-function oxidase system, which can bring about ?-oxidation of fatty acids, was induced by treatment of the rat with phenobarbitone, there was no change in the ketone-body production from fatty acids, nor was there a production of glucose from even-numbered fatty acids. The latter would be expected if ?-oxidation occurred. Thus ?-oxidation did not play a significant role in the metabolism of fatty acids. 7. Arachidonate was almost quantitatively converted into ketone bodies and yielded no glucose, demonstrating that gluconeogenesis from poly-unsaturated fatty acids with an even number of carbon atoms does not occur. 8. The rates of ketogenesis from unsaturated fatty acids (sorbate, undecylenate, crotonate, vinylacetate) were similar to those from the corresponding saturated fatty acids. 9. Addition of oleate together with shorter-chain fatty acids gave only a slightly higher rate of ketone-body formation than oleate alone. 10. Glucose, lactate, fructose, glycerol and other known antiketogenic substances strongly inhibited endogenous ketogenesis but had no effects on the rate of ketone-body formation in the presence of 2mm-oleate. Thus the concentrations of free fatty acids and of other oxidizable substances in the liver are key factors determining the rate of ketogenesis. PMID:5500312

Krebs, H. A.; Hems, R.

1970-01-01

197

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 2013-07-01 false Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). 721...Chemical Substances § 721.10629 Fatty acids, tall-oil, reaction products with...

2013-07-01

198

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 2014-07-01 false Fatty acids, tall-oil, reaction products with modified fatty acids and polyalkanolamines (generic). 721...Chemical Substances § 721.10629 Fatty acids, tall-oil, reaction products with...

2014-07-01

199

Tissue fatty acid composition and estimated ? desaturase activity after castration in chicken broilers fed with linseed or sunflower oil.  

PubMed

The aims of this study were to investigate the influence of the short-term addition of sunflower and linseed oil and castration on fatty acid composition and desaturation indexes in chicken broilers. Forty-eight male Ross 308 chicken broilers were supplemented with 5% of sunflower or linseed oil. The four experimental groups were linseed oil supplementation and castration (LC), linseed oil without castration (LN), sunflower oil and castration (SC) and sunflower oil without castration (SN). There was no significant influence of castration or oil supplement on live weights, weight gain, feed intake or feed conversion. Castration resulted in an increase in polyunsaturated fatty acids (PUFA), total n3, n6, measured desaturation indexes and a decrease in the saturated fatty acid (SFA) and monounsaturated fatty acid (MUFA) content of abdominal fat. In breast muscle, castration increased PUFA and 18:3n3 values, while in the liver tissue, castration did not influence the parameters measured. Linseed oil supplementation significantly increased 18:3n3, n3 long chain polyunsaturated fatty acids (LC PUFA), total n3 and decreased total n6, n6/n3 ratio, and 20:4n6 content. Values for 20:4n6 were the highest in SC and the lowest in the LC group. Linseed oil also significantly decreased ?5 and ?4 desaturation indexes in the thighs and ?5 and ?5, 6 in abdominal fat and the liver. These results suggest that short-term supplementation of basal diet with 5% of linseed oil could significantly increase n3 LC PUFA and decrease n6/n3 ratio content in the edible tissues of chicken broilers, without adverse effects on growth performance. Meanwhile, castration only improved fatty acid profile in abdominal fat, which is not nutritionally important. The interactions observed between basal diet, supplemented oil, sex hormones and other non-nutritional factors must be elucidated in future trials in order to correctly predict the nutritional value of linseed-fed poultry. PMID:23905627

Mašek, T; Star?evi?, K; Filipovi?, N; Stojevi?, Z; Brozi?, D; Gottstein, Z; Severin, K

2014-04-01

200

Hypocoagulant and lipid-lowering effects of dietary n-3 polyunsaturated fatty acids with unchanged platelet activation in rats.  

PubMed

We investigated the effects of dietary polyunsaturated fatty acids (PUFAs) on blood lipids and processes that determine hemostatic potential: platelet activation, coagulation, and fibrinolysis. For 8 to 10 weeks, Wistar rats were fed a high-fat diet containing various amounts (2% to 16%) of n-3 PUFAs derived from fish oil (FO) or a diet enriched in n-6 PUFAs from sunflower seed oil (SO). Only the FO diets caused a reduction in mean platelet volume, platelet arachidonate level, and formation of thromboxane B2 by activated platelets, but neither of the diets had a measurable effect on platelet activation. The FO-rich diets decreased the plasma concentrations of triglycerides and cholesterol, whereas the SO diet reduced triglycerides only. Parameters of fibrinolysis and standard coagulation times, ie, activated partial thromboplastin time and prothrombin time, were only marginally influenced by these diets. In contrast, dietary FO, but not SO, led to decreased levels of the vitamin K-dependent coagulation factors prothrombin and factor VII, while the level of antithrombin III was unchanged. The endogenous thrombin potential (ETP) was measured with an assay developed to detect the hypocoagulable state of plasma. After activation with tissue factor and phospholipids, the ETP was reduced by 23% or more in plasma from animals fed a diet with >4% FO. No significant effect of the SO diet on ETP was observed. Control experiments with plasma from warfarin-treated rats indicated that the ETP was more sensitive to changes in prothrombin concentration than in factor VII concentration. Taken together, these results indicate that in rats, prolonged administration of n-3 but not n-6 PUFAs can lead to a hypocoagulable state of plasma through a reduced capacity of vitamin K-dependent thrombin generation, with unchanged thrombin inactivation by antithrombin III. PMID:9743238

Nieuwenhuys, C M; Béguin, S; Offermans, R F; Emeis, J J; Hornstra, G; Heemskerk, J W

1998-09-01

201

Fatty Acid and Phytosterol Content of Commercial Saw Palmetto Supplements  

PubMed Central

Saw palmetto supplements are one of the most commonly consumed supplements by men with prostate cancer and/or benign prostatic hyperplasia (BPH). Some studies have found significant improvements in BPH and lower urinary tract symptoms (LUTS) with saw palmetto supplementation, whereas others found no benefits. The variation in the efficacy in these trials may be a result of differences in the putative active components, fatty acids and phytosterols, of the saw palmetto supplements. To this end, we quantified the major fatty acids (laurate, myristate, palmitate, stearate, oleate, linoleate) and phytosterols (campesterol, stigmasterol, ?-sitosterol) in 20 commercially available saw palmetto supplements using GC-FID and GC-MS, respectively. Samples were classified into liquids, powders, dried berries, and tinctures. Liquid saw palmetto supplements contained significantly higher (p < 0.05) concentrations of total fatty acids (908.5 mg/g), individual fatty acids, total phytosterols (2.04 mg/g), and individual phytosterols, than the other supplement categories. Powders contained significantly higher (p < 0.05) concentrations of total fatty acids than tinctures, which contain negligible amounts of fatty acids (46.3 mg/g) and phytosterols (0.10 mg/g). Our findings suggest that liquid saw palmetto supplements may be the best choice for individuals who want to take a saw palmetto supplement with the highest concentrations of both fatty acids and phytosterols. PMID:24067389

Penugonda, Kavitha; Lindshield, Brian L.

2013-01-01

202

Peroxisome Proliferator-Activated Receptor ?/? (PPAR?/?) but Not PPAR? Serves as a Plasma Free Fatty Acid Sensor in Liver ? †  

PubMed Central

Peroxisome proliferator-activated receptor ? (PPAR?) is an important transcription factor in liver that can be activated physiologically by fasting or pharmacologically by using high-affinity synthetic agonists. Here we initially set out to elucidate the similarities in gene induction between Wy14643 and fasting. Numerous genes were commonly regulated in liver between the two treatments, including many classical PPAR? target genes, such as Aldh3a2 and Cpt2. Remarkably, several genes induced by Wy14643 were upregulated by fasting independently of PPAR?, including Lpin2 and St3gal5, suggesting involvement of another transcription factor. Using chromatin immunoprecipitation, Lpin2 and St3gal5 were shown to be direct targets of PPAR?/? during fasting, whereas Aldh3a2 and Cpt2 were exclusive targets of PPAR?. Binding of PPAR?/? to the Lpin2 and St3gal5 genes followed the plasma free fatty acid (FFA) concentration, consistent with activation of PPAR?/? by plasma FFAs. Subsequent experiments using transgenic and knockout mice for Angptl4, a potent stimulant of adipose tissue lipolysis, confirmed the stimulatory effect of plasma FFAs on Lpin2 and St3gal5 expression levels via PPAR?/?. In contrast, the data did not support activation of PPAR? by plasma FFAs. The results identify Lpin2 and St3gal5 as novel PPAR?/? target genes and show that upregulation of gene expression by PPAR?/? is sensitive to plasma FFA levels. In contrast, this is not the case for PPAR?, revealing a novel mechanism for functional differentiation between PPARs. PMID:19805517

Sanderson, Linda M.; Degenhardt, Tatjana; Koppen, Arjen; Kalkhoven, Eric; Desvergne, Beatrice; Müller, Michael; Kersten, Sander

2009-01-01

203

Inhibition of fatty acid amide hydrolase activates Nrf2 signalling and induces heme oxygenase 1 transcription in breast cancer cells  

PubMed Central

BACKGROUND AND PURPOSE Endocannabinoids such as anandamide (AEA) are important lipid ligands regulating cell proliferation, differentiation and apoptosis. Their levels are regulated by hydrolase enzymes, the fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MGL). Here, we investigated whether FAAH or AEA are involved in NF (erythroid-derived 2)-like 2 (Nrf2)/antioxidant responsive element (ARE) pathway. EXPERIMENTAL APPROACH The aim of this study was to analyse the effects of AEA or FAAH inhibition by the URB597 inhibitor or FAAH/siRNA on the activation of Nrf2-ARE signalling pathway and heme oxygenase-1 (HO-1) induction and transcription. KEY RESULTS Endogenous AEA was detected in the immortalized human mammary epithelial MCF-10A cells (0.034 ng per 106 cells) but not in MCF-7 or MDA-MB-231 breast cancer cells. Because breast tumour cells express FAAH abundantly, we examined the effects of FAAH on Nrf2/antioxidant pathway. We found that inhibition of FAAH by the URB597 inhibitor induced antioxidant HO-1 in breast cancer cells and MCF-10A cells. RNAi-mediated knockdown of FAAH or treatment with AEA-activated ARE-containing reporter induced HO-1 mRNA and protein expression, independent of the cannabinoid receptors, CB1, CB2 or TRPV1. Furthermore, URB597, AEA and siRNA-FAAH treatments induced the nuclear translocation of Nrf2, while siRNA-Nrf2 treatment and Keap1 expression blocked AEA, URB597 and si-FAAH from activation of ARE reporter and HO-1 induction. siRNA-HO-1 treatment decreased the viability of breast cancer cells and MCF-10A cells. CONCLUSIONS AND IMPLICATIONS These data uncovered a novel mechanism by which inhibition of FAAH or exposure to AEA induced HO-1 transcripts and implicating AEA and FAAH as direct modifiers in signalling mediated activation of Nrf2-HO-1 pathway, independent of cannabinoid receptors. PMID:23347118

Li, H; Wood, J T; Whitten, K M; Vadivel, S K; Seng, S; Makriyannis, A; Avraham, H K

2013-01-01

204

Fatty acid breakdown in developing embryos of Brassica napus L.  

PubMed

Developing Brassica napus embryos are primarily concerned with the accumulation of storage products, namely oil, starch and protein. The presence of fatty acid catabolic pathways in the background of this biosynthetic activity was investigated. Enzymes involved in the process of lipid mobilization, such as malate synthase and isocitrate lyase, are detectable towards the late stages of embryo development. [(14)C]Acetate feeding experiments also reveal that fatty acid catabolism becomes increasingly functional as the embryo matures. PMID:11171195

Chia, T; Rawsthorne, S

2000-12-01

205

The Arabidopsis Peroxisomal ABC Transporter, Comatose, Complements the Saccharomyces cerevisiae pxa1 pxa2? Mutant for Metabolism of Long-chain Fatty Acids and Exhibits Fatty Acyl-CoA-stimulated ATPase Activity*  

PubMed Central

The Arabidopsis ABC transporter Comatose (CTS; AtABCD1) is required for uptake into the peroxisome of a wide range of substrates for ?-oxidation, but it is uncertain whether CTS itself is the transporter or if the transported substrates are free acids or CoA esters. To establish a system for its biochemical analysis, CTS was expressed in Saccharomyces cerevisiae. The plant protein was correctly targeted to yeast peroxisomes, was assembled into the membrane with its nucleotide binding domains in the cytosol, and exhibited basal ATPase activity that was sensitive to aluminum fluoride and abrogated by mutation of a conserved Walker A motif lysine residue. The yeast pxa1 pxa2? mutant lacks the homologous peroxisomal ABC transporter and is unable to grow on oleic acid. Consistent with its exhibiting a function in yeast akin to that in the plant, CTS rescued the oleate growth phenotype of the pxa1 pxa2? mutant, and restored ?-oxidation of fatty acids with a range of chain lengths and varying degrees of desaturation. When expressed in yeast peroxisomal membranes, the basal ATPase activity of CTS could be stimulated by fatty acyl-CoAs but not by fatty acids. The implications of these findings for the function and substrate specificity of CTS are discussed. PMID:20659892

Nyathi, Yvonne; De Marcos Lousa, Carine; van Roermund, Carlo W.; Wanders, Ronald J. A.; Johnson, Barbara; Baldwin, Stephen A.; Theodoulou, Frederica L.; Baker, Alison

2010-01-01

206

Alterations of N-3 Polyunsaturated Fatty Acid-Activated K2P Channels in Hypoxia-Induced Pulmonary Hypertension  

PubMed Central

Polyunsaturated fatty acid (PUFA)-activated two-pore domain potassium channels (K2P) have been proposed to be expressed in the pulmonary vasculature. However, their physiological or pathophysiological roles are poorly defined. Here we tested the hypothesis that PUFA-activated K2P are involved in pulmonary vasorelaxation and that alterations of channel expression are pathophysiologically linked to pulmonary hypertension. Expression of PUFA-activated K2P in the murine lung was investigated by quantitative reverse-transcription polymerase chain reaction (qRT-PCR), immunohistochemistry (IHC), by patch clamp (PC), and myography. K2P-gene expression was examined in chronic hypoxic mice. QRT-PCR showed that the K2P2.1 and K2P6.1 were the predominantly expressed K2P in the murine lung. IHC revealed protein expression of K2P2.1 and K2P6.1 in the endothelium of pulmonary arteries and of K2P6.1 in bronchial epithelium. PC showed pimozide-sensitive K2P-like K+-current activated by docosahexaenoic acid (DHA) in freshly isolated endothelial cells as well as DHA-induced membrane hyperpolarization. Myography on pulmonary arteries showed that DHA-induced concentration-dependent and instantaneous relaxations that were resistant to endothelial removal and inhibition of NO and prostacyclin synthesis and to a cocktail of blockers of calcium-activated K+ channels but were abolished by high extracellular (30 mM) K+-concentration. Gene expression and protein of K2P2.1 were not altered in chronic hypoxic mice while K2P6.1 was up-regulated by fourfold. In conclusion, the PUFA-activated K2P2.1 and K2P6.1 are expressed in murine lung and functional K2P-like channels contribute to endothelium-hyperpolarization and pulmonary artery relaxation. The increased K2P6.1-gene expression may represent a novel counter-regulatory mechanism in pulmonary hypertension, and suggest that arterial K2P2.1 and K2P6.1 could be novel therapeutic targets. PMID:23724868

Nielsen, Gorm; Wandall-Frostholm, Christine; Sadda, Veeranjaneyulu; Oliván-Viguera, Aida; Lloyd, Eric E.; Bryan, Robert M.; Simonsen, Ulf; Köhler, Ralf

2013-01-01

207

The role of essential fatty acids in development  

Technology Transfer Automated Retrieval System (TEKTRAN)

Fatty acids are aliphatic monocarboxylic acids. They are classified as saturated, monounsaturated, or polyunsaturated fatty acids depending upon the number of double bonds in the carbon chain. Saturated fatty acids have no double bonds, monounsaturated fatty acids have 1 double bond, and polyunsat...

208

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

PubMed

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. PMID:24126964

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

2014-01-01

209

Anticandidal activity of cell extracts from 13 probiotic Lactobacillus strains and characterisation of lactic acid and a novel fatty acid derivative from one strain.  

PubMed

This study investigated the anti-Candida activity of methanol extracts from freeze-dried probiotic cells and the isolation of some constituents in the extracts. The MIC values of the probiotic methanol cell extracts against Candida albicans ranged between 1.25 and 5mg/ml after 48 h of incubation. However, Lactococcus latics subsp. lactis strain X and Lactobacillus casei strain B extracts had an MIC of 10mg/ml after 48 h of incubation. The extracts had fungistatic rather than fungicidal activity. These extracts had a much higher antifungal activity than antifungal compounds isolated from the growth medium by many other authors. This indicates that probiotics may also release antifungal compounds in their cells that could contribute to a therapeutic effect. Lactic acid (1) and 6-O-(?-D-glucopyranosyl)-1,6-di-O-pentadecanoyl-?-D-glucopyranose a novel fatty acid derivative (2) were isolated from methanol probiotic extracts and the structure of these compounds were elucidated using NMR (1 and 2D) and mass spectrometry (MS). PMID:24996359

Nyanzi, Richard; Awouafack, Maurice D; Steenkamp, Paul; Jooste, Piet J; Eloff, Jacobus N

2014-12-01

210

Polyunsaturated fatty acids and fetal brain development  

PubMed Central

Abstract Question I have learned that one of the manufacturers of prenatal vitamins has added omega-3 fatty acids and claims that they help support fetal cognitive health and brain function. Is this based on evidence? Answer The claim that polyunsaturated fatty acids help improve fetal brain and eye development has been made for more than a decade. Unfortunately it is not supported by evidence-based science. Long-term studies have failed to show such effects. Implying to women that using these products will improve the brain development of their children is unwarranted and misleading. Health Canada should clarify the contradictions in its statements about omega-3 fatty acids.

Koren, Gideon

2015-01-01

211

Influence of fatty acids on wine foaming.  

PubMed

The influence of fatty acids (free and bound as ethyl esters) on wine foaming was studied in different white wines and the corresponding sparkling wines. Moreover, from three of these wines the foam formed by CO(2) injection was separated, and two fractions were then obtained: foam wine (FW) and remainder wine (RW). In these fractions and the sparkling wines produced from them, foam properties and fatty acids were also determined. The free fatty acids C8, C10, and C12 were negatively correlated with foamability (HM), whereas the ethyl esters of hexanoic, octanoic, and decanoic acids were positively related to HM. The value of HM was directly proportional to the ratio of esterified to unesterified fatty acids. This was confirmed by the changes that occur in the esterification ratio during the second fermentation and aging. No influence was observed on either the Bikerman coefficient or the stability time of foam. PMID:12428957

Gallart, Magdalena; López-Tamames, Elvira; Suberbiola, Gabriel; Buxaderas, Susana

2002-11-20

212

Effects of silicon on H +ATPase and H +-PPase activity, fatty acid composition and fluidity of tonoplast vesicles from roots of salt-stressed barley ( Hordeum vulgare L.)  

Microsoft Academic Search

We investigated the effects of silicon (Si) on time-dependent changes in root tonoplast H+-ATPase and H+-PPase activities, membrane fatty acid compositions and tonoplast fluidity in two barley (Hordeum vulgare L.) cultivars differing in salt tolerance. Plants were grown in NaCl-free (control) and NaCl-supplied (60 and 120mM, respectively) nutrient solutions with or without 1.0mM Si. Plant roots were harvested to isolate

Yongchao Liang; Wenhua Zhang; Qin Chen; Ruixing Ding

2005-01-01

213

Co-fermentation of waste activated sludge with food waste for short-chain fatty acids production: effect of pH at ambient temperature  

Microsoft Academic Search

Effect of pH ranging from 4.0 to 11.0 on cofermentation of waste activated sludge (WAS) with food waste for short-chain fatty\\u000a acids (SCFAs) production at ambient temperature was investigated in this study. Experimental results showed that the addition\\u000a of food waste significantly improved the performance of WAS fermentation system, which resulted in the increases of SCFAs\\u000a production and substrate reduction.

Leiyu Feng; Yuanyuan Yan; Yinguang Chen

214

Active site modification of the ?-ketoacyl-ACP synthase FabF3 of Streptomyces coelicolor affects the fatty acid chain length of the CDA lipopeptides.  

PubMed

Using site directed mutagenesis we altered an active site residue (Phe107) of the enzyme encoded by fabF3 (SCO3248) in the Streptomyces coelicolor gene cluster required for biosynthesis of the calcium dependent antibiotics (CDAs), successfully generating two novel CDA derivatives comprising truncated (C4) lipid side chains and confirming that fabF3 encodes a KAS-II homologue that is involved in determining CDA fatty acid chain length. PMID:21135931

Lewis, Richard A; Nunns, Laura; Thirlway, Jenny; Carroll, Kathleen; Smith, Colin P; Micklefield, Jason

2011-02-14

215

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

PubMed Central

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

Meyer, Karl H.; Schweizer, Eckhart

1974-01-01

216

Structure and expression of fatty acid desaturases  

Microsoft Academic Search

Fatty acid desaturases are enzymes that introduce double bonds into fatty acyl chains. They are present in all groups of organisms, i.e., bacteria, fungi, plants and animals, and play a key role in the maintenance of the proper structure and functioning of biological membranes. The desaturases are characterized by the presence of three conserved histidine tracks which are presumed to

Dmitry A. Los; Norio Murata

1998-01-01

217

Nrf2 affects the efficiency of mitochondrial fatty acid oxidation  

PubMed Central

Transcription factor Nrf2 (NF-E2 p45-related factor 2) regulates the cellular redox homoeostasis and cytoprotective responses, allowing adaptation and survival under conditions of stress. The significance of Nrf2 in intermediary metabolism is also beginning to be recognized. Thus this transcription factor negatively affects fatty acid synthesis. However, the effect of Nrf2 on fatty acid oxidation is currently unknown. In the present paper, we report that the mitochondrial oxidation of long-chain (palmitic) and short-chain (hexanoic) fatty acids is depressed in the absence of Nrf2 and accelerated when Nrf2 is constitutively active. Addition of fatty acids stimulates respiration in heart and liver mitochondria isolated from wild-type mice. This effect is significantly weaker when Nrf2 is deleted, whereas it is stronger when Nrf2 activity is constitutively high. In the absence of glucose, addition of fatty acids differentially affects the production of ATP in mouse embryonic fibroblasts from wild-type, Nrf2-knockout and Keap1 (Kelch-like ECH-associated protein 1)-knockout mice. In acute tissue slices, the rate of regeneration of FADH2 is reduced when Nrf2 is absent. This metabolic role of Nrf2 on fatty acid oxidation has implications for chronic disease conditions including cancer, metabolic syndrome and neurodegeneration. PMID:24206218

Ludtmann, Marthe H. R.; Angelova, Plamena R.; Zhang, Ying; Abramov, Andrey Y.; Dinkova-Kostova, Albena T.

2014-01-01

218

Activity and Viability of Methanogens in Anaerobic Digestion of Unsaturated and Saturated Long-Chain Fatty Acids  

PubMed Central

Lipids can be anaerobically digested to methane, but methanogens are often considered to be highly sensitive to the long-chain fatty acids (LCFA) deriving from lipids hydrolysis. In this study, the effect of unsaturated (oleate [C18:1]) and saturated (stearate [C18:0] and palmitate [C16:0]) LCFA toward methanogenic archaea was studied in batch enrichments and in pure cultures. Overall, oleate had a more stringent effect on methanogens than saturated LCFA, and the degree of tolerance to LCFA was different among distinct species of methanogens. Methanobacterium formicicum was able to grow in both oleate- and palmitate-degrading enrichments (OM and PM cultures, respectively), whereas Methanospirillum hungatei only survived in a PM culture. The two acetoclastic methanogens tested, Methanosarcina mazei and Methanosaeta concilii, could be detected in both enrichment cultures, with better survival in PM cultures than in OM cultures. Viability tests using live/dead staining further confirmed that exponential growth-phase cultures of M. hungatei are more sensitive to oleate than are M. formicicum cultures; exposure to 0.5 mM oleate damaged 99% ± 1% of the cell membranes of M. hungatei and 53% ± 10% of the cell membranes of M. formicicum. In terms of methanogenic activity, M. hungatei was inhibited for 50% by 0.3, 0.4, and 1 mM oleate, stearate, and palmitate, respectively. M. formicicum was more resilient, since 1 mM oleate and >4 mM stearate or palmitate was needed to cause 50% inhibition on methanogenic activity. PMID:23645196

Sousa, Diana Z.; Salvador, Andreia F.; Ramos, Juliana; Guedes, Ana P.; Barbosa, Sónia; Stams, Alfons J. M.; Alves, M. Madalena

2013-01-01

219

Rational Design of Fatty Acid Amide Hydrolase Inhibitors that Act by Covalently Bonding to Two Active Site Residues  

PubMed Central

The design and characterization of ?-ketoheterocycle fatty acid amide hydrolase (FAAH) inhibitors are disclosed that additionally and irreversibly target a cysteine (Cys269) found in the enzyme cytosolic port while maintaining the reversible covalent Ser241 attachment responsible for their rapid and initially reversible enzyme inhibition. Two ?-ketooxazoles (3 and 4) containing strategically placed electrophiles at the C5 position of the pyridyl substituent of 2 (OL-135) were prepared and examined as inhibitors of FAAH. Consistent with the observed time-dependent non-competitive inhibition, the co-crystal X-ray structure of 3 bound to a humanized variant of rat FAAH revealed that 3 was not only covalently bound to the active site catalytic nucleophile Ser241 as a deprotonated hemiketal, but also to Cys269 through the pyridyl C5-substituent, thus providing an inhibitor with dual covalent attachment in the enzyme active site. In vivo characterization of the prototypical inhibitors in mice demonstrate that they raise endogenous brain levels of FAAH substrates to a greater extent and for a much longer duration (>6 h) than the reversible inhibitor 2, indicating that the inhibitors accumulate and persist in the brain to completely inhibit FAAH for a prolonged period. Consistent with this behavior and the targeted irreversible enzyme inhibition, 3 reversed cold allodynia in the chronic constriction injury model of neuropathic pain in mice for a sustained period (>6 h) beyond that observed with the reversible inhibitor 2, providing effects that were unchanged over the 1–6 h time course monitored. PMID:23581831

Otrubova, Katerina; Brown, Monica; McCormick, Michael S.; Han, Gye W.; O’Neal, Scott T.; Cravatt, Benjamin F.; Stevens, Raymond C.; Lichtman, Aron H.; Boger, Dale L.

2013-01-01

220

Dysregulation of hepatic fatty acid metabolism in chronic kidney disease  

PubMed Central

Background Chronic kidney disease (CKD) results in hypertriglyceridemia which is largely due to impaired clearance of triglyceride-rich lipoproteins occasioned by downregulation of lipoprotein lipase and very low-density lipoprotein (LDL) receptor in the skeletal muscle and adipose tissue and of hepatic lipase and LDL receptor-related protein in the liver. However, data on the effect of CKD on fatty acid metabolism in the liver is limited and was investigated here. Methods Male Sprague-Dawley rats were randomized to undergo 5/6 nephrectomy (CRF) or sham operation (control) and observed for 12 weeks. The animals were then euthanized and their liver tissue tested for nuclear translocation (activation) of carbohydrate-responsive element binding protein (ChREBP) and sterol-responsive element binding protein-1 (SREBP-1) which independently regulate the expression of key enzyme in fatty acid synthesis, i.e. fatty acid synthase (FAS) and acyl-CoA carboxylase (ACC) as well as nuclear Peroxisome proliferator-activated receptor alpha (PPAR?) which regulates the expression of enzymes involved in fatty acid oxidation and transport, i.e. L-FABP and CPT1A. In addition, the expression of ATP synthase ?, ATP synthase ?, glycogen synthase and diglyceride acyltransferase 1 (DGAT1) and DGAT2 were determined. Results Compared with controls, the CKD rats exhibited hypertriglyceridemia, elevated plasma and liver tissue free fatty acids, increased nuclear ChREBP and reduced nuclear SREBP-1 and PPAR?, upregulation of ACC and FAS and downregulation of L-FABP, CPT1A, ATP synthase ?, glycogen synthase and DGAT in the liver tissue. Conclusion Liver in animals with advanced CKD exhibits ChREBP-mediated upregulation of enzymes involved in fatty acid synthesis, downregulation of PPAR?-regulated fatty acid oxidation system and reduction of DGAT resulting in reduced fatty acid incorporation in triglyceride. PMID:23045433

Jin, Kyubok; Norris, Keith; Vaziri, Nosratola D.

2013-01-01

221

Endoplasmic reticulum microenvironment and conserved histidines govern ELOVL4 fatty acid elongase activity  

PubMed Central

Autosomal dominant Stargardt-like macular dystrophy (STGD3) in humans results from mutations in elongation of very long chain FAs-like 4 (ELOVL4), which leads to vision loss in young adults. ELOVL4 is an integral endoplasmic reticulum (ER) protein that mediates the elongation of very long chain (VLC) FAs. Mutations in ELOVL4 lead to truncation and mislocalization of the translated protein from the ER, the site of FA elongation. Little is known about the enzymatic elongation of VLC-FAs by ELOVL4. We over-expressed full-length mouse ELOVL4, an N-glycosylation-deficient mutant, an ER-retention mutant, and mutants of active site histidines to parse their individual roles in VLC-FA elongation. ELOVL4 elongated appropriate precursors to the corresponding VLC-FA species ?28 carbons. Active site histidine mutants of ELOVL4 did not elongate appropriate precursors, establishing ELOVL4 as the elongase. Displacing ELOVL4 from the ER was sufficient to cause loss of condensation activity, while absence of N-glycosylation was irrelevant for enzyme function. This study shows that ELOVL4 enzymatic activity is governed by individual histidines in its active site and the ER microenvironment, both of which are essential for elongation of VLC-FAs. PMID:24569140

Logan, Sreemathi; Agbaga, Martin-Paul; Chan, Michael D.; Brush, Richard S.; Anderson, Robert E.

2014-01-01

222

Effect of fatty acids on phase behavior of hydrated dipalmitoylphosphatidylcholine bilayer: saturated versus unsaturated fatty acids  

Microsoft Academic Search

The effect of some fatty acids on the phase behavior of hydrated dipalmitoylphosphatidylcholine (DPPC) bilayer was investigated with special interest in possible difference between saturated and unsaturated fatty acids. The phase behavior of hydrated DPPC bilayer was followed by a differential scanning calorimetry and a Fourier transform infrared spectroscopy. The addition of palmitic acid (PA) increased the bilayer phase transition

Tohru Inoue; Shin-ichi Yanagihara; Yasuhito Misono; Masao Suzuki

2001-01-01

223

New Advances in Fatty Acids as Antimalarial, Antimycobacterial and Antifungal Agents  

PubMed Central

This review deals with the most recent findings on the antimalarial, antimycobacterial, and antifungal properties of fatty acids, with particular emphasis on novel marine fatty acids. The first section deals with the most recent and some background literature on what has been the latest developments with respect to fatty acids as antimalarial agents and the importance of enzyme inhibition, in particular the inhibition of the enoyl-ACP-reductase (Fab I) of P. falciparum, the principal agent responsible for malaria. This section of the review also emphasizes the latest antimalarial research with the very long-chain ?5,9 fatty acids from sponges. The second section of the review deals with the recent literature on the antimycobacterial activity of fatty acids and the importance of enzyme inhibition, in particular the inhibition of the enoyl-ACP-reductase (InhA) of M. tuberculosis for antimycobacterial activity. The inhibitory activities of the ?5,9 fatty acids against InhA as well as that of the ?-methoxylated fatty acids are also discussed. The importance of ?5,9 fatty acids as topoisomerase I inhibitors and its connection to cancer is also reviewed. The last part of the review, the antifungal section, also emphasizes the most recent research with antifungal fatty acids and the importance of enzyme inhibition, in particular N-myristoyltransferase (NMT) inhibition, for antifungal activity. This last section of the review emphasizes the latest research with the ?-methoxylated fatty acids but the importance of acetylenic fatty acids is also considered. PMID:18023422

Carballeira, N.M.

2008-01-01

224

Flux decline during ultrafiltration of protein-fatty acid mixtures  

Microsoft Academic Search

Proteins frequently co-exist with fatty acids and have specific binding interactions, forming complexes which can affect membrane performance. While specific and non-specific binding to proteins occurs at lower concentrations of fatty acid, at higher concentrations, excess fatty acids can produce additional interactions by adsorption in the protein cake or in the membrane pores. The effect of the fatty acid on

P. Priyananda; V. Chen

2006-01-01

225

The Effects of Dietary Fatty Acids on Lipid Metabolism  

Technology Transfer Automated Retrieval System (TEKTRAN)

Depending on their degree of unsaturation and chain length, dietary fatty acids can affect blood lipids and lipoprotein levels. Both saturated fatty acids (12:0-16:0) and dietary cholesterol increase blood cholesterol and polyunsaturated fatty acids reduce it. Trans fatty acids, even though are pol...

226

Saccharomyces cerevisiae contains four fatty acid activation (FAA) genes: an assessment of their role in regulating protein N-myristoylation and cellular lipid metabolism.  

PubMed

Saccharomyces cerevisiae has been used as a model for studying the regulation of protein N-myristoylation. MyristoylCoA:protein N-myristoyl-transferase (Nmt1p), is essential for vegetative growth and uses myristoylCoA as its substrate. MyristoylCoA is produced by the fatty acid synthetase (Fas) complex and by cellular acylCoA synthetases. We have recently isolated three unlinked Fatty Acid Activation (FAA) genes encoding long chain acylCoA synthetases and have now recovered a fourth by genetic complementation. When Fas is active and NMT1 cells are grown on media containing a fermentable carbon source, none of the FAA genes is required for vegetative growth. When Fas is inactivated by a specific inhibitor (cerulenin), NMT1 cells are not viable unless the media is supplemented with long chain fatty acids. Supplementation of cellular myristoylCoA pools through activation of imported myristate (C14:0) is predominantly a function of Faa1p, although Faa4p contributes to this process. Cells with nmt181p need larger pools of myristoylCoA because of the mutant enzyme's reduced affinity for this substrate. Faa1p and Faa4p are required for maintaining the viability of nmt1-181 strains even when Fas is active. Overexpression of Faa2p can rescue nmt1-181 cells due to activation of an endogenous pool of C14:0. This pool appears to be derived in part from membrane phospholipids since overexpression of Plb1p, a nonessential lysophospholipase/phospholipase B, suppresses the temperature-sensitive growth arrest and C14:0 auxotrophy produced by nmt1-181. None of the four known FAAs is exclusively responsible for targeting imported fatty acids to peroxisomal beta-oxidation pathways. Introduction of a peroxisomal assembly mutation, pas1 delta, into isogenic NMT1 and nmt1-181 strains with wild type FAA alleles revealed that when Fas is inhibited, peroxisomes contribute to myristoylCoA pools used by Nmt1p. When Fas is active, a fraction of cellular myristoylCoA is targeted to peroxisomes. A NMT1 strain with deletions of all four FAAs is still viable at 30 degrees C on media containing myristate, palmitate, or oleate as the sole carbon source--indicating that S. cerevisiae contains at least one other FAA which directs fatty acids to beta-oxidation pathways. PMID:7962057

Johnson, D R; Knoll, L J; Levin, D E; Gordon, J I

1994-11-01

227

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2012 CFR

...fatty acids may be safely used in food and in the manufacture of food components in accordance with...prescribed conditions: (a) The food additive consists of one or any mixture of the following straight-chain monobasic carboxylic...

2012-04-01

228

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2013 CFR

...fatty acids may be safely used in food and in the manufacture of food components in accordance with...prescribed conditions: (a) The food additive consists of one or any mixture of the following straight-chain monobasic carboxylic...

2013-04-01

229

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2014 CFR

...fatty acids may be safely used in food and in the manufacture of food components in accordance with...prescribed conditions: (a) The food additive consists of one or any mixture of the following straight-chain monobasic carboxylic...

2014-04-01

230

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2011 CFR

...fatty acids may be safely used in food and in the manufacture of food components in accordance with...prescribed conditions: (a) The food additive consists of one or any mixture of the following straight-chain monobasic carboxylic...

2011-04-01

231

Oxygenases for aliphatic hydrocarbons and fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

Oxygenases catalyzing the insertion of oxygen into either aliphatic hydrocarbons or fatty acids have great similarity. There are two classes of oxygenases: monooxygenases and dioxygenases. Dioxygenase inserts both atoms of molecular oxygen into a substrate, whereas monooxygenase incorporates one a...

232

Fatty acid-related functions.  

PubMed

The first recommendations for specific nutrient quantities that must be obtained to support health were made by the US Department of Agriculture before 1939. Hazel Stiebeling was the leader of this effort and the scientific background was published in the Yearbook of Agriculture. The recommendations clearly stated that food must be available to provide the nutrients to support health. The science of nutrition in the United States is engaged in the most thorough review and reexamination of the recommended dietary allowances in at least a generation of nutrition scientists. There is a new awareness of nutrition complexity and the likelihood of identification of new essential nutrients. This meeting was devoted to the search for functional endpoints to reach quantitative estimates of dietary substances needed to support a function. Included in that concept is determining a range of individual needs and identifying factors that alter these needs. We give the rationale for endpoints of fatty acid metabolism related to platelets and the risk of thrombosis, give the rationale for the recommendation for a new nutrient, and show the necessity for including nutrient interaction in the determination of needs for two nutrients. PMID:8644699

Dupont, J; Holub, B J; Knapp, H R; Meydani, M

1996-06-01

233

Genetic variability of milk fatty acids  

Microsoft Academic Search

The milk fatty acid (FA) profile is far from the optimal fat composition in regards to human health. The natural sources of\\u000a variation, such as feeding or genetics, could be used to increase the concentrations of unsaturated fatty acids. The impact\\u000a of feeding is well described. However, genetic effects on the milk FA composition begin to be extensively studied. This

V. M.-R. Arnould; H. Soyeurt

2009-01-01

234

Zinc and Fatty Acids in Depression  

Microsoft Academic Search

Polyunsaturated Fatty acids (PUFAs) seem to be helpful in the therapy of depression. Zinc (Zn) may be one co-factor contributing\\u000a to their antidepressive effect. Zn acts lipid protective and is a constituent of fatty acid metabolism enzymes. In animals,\\u000a an antidepressive effect of Zn was already demonstrated. Therefore, if and how Zn and PUFAs correlate in depressive patients\\u000a or in

Gisela Irmisch; Detlef Schlaefke; Joerg Richter

2010-01-01

235

The antifungal activity of the cuticular and internal fatty acid methyl esters and alcohols in Calliphora vomitoria.  

PubMed

SUMMARY The composition of the fatty acid methyl ester (FAME) and alcohol fractions of the cuticular and internal lipids of Calliphora vomitoria larvae, pupae and male/female adults was obtained by separating these two fractions by HPLC-LLSD and analysing them quantitatively using GC-MS. Analysis of the cuticular lipids of the worldwide, medically important ectoparasite C. vomitoria revealed 6 FAMEs with odd-numbered carbon chains from C15:0 to C19:0 in the larvae, while internal lipids contained 9 FAMEs ranging from C15:1 to C19:0. Seven FAMEs from C15:0 to C19:0 were identified in the cuticular lipids of the pupae, whereas the internal lipids of the pupae contained 10 FAMEs from C13:0 to C19:0. The cuticular lipids of males and females and also the internal lipids of males contained 5, 7 and 6 FAMEs from C15:0 to C19:0 respectively. Seven FAMEs from C13:0 to C19:0 were identified in the internal lipids of females, and 7, 6, 5 and 3 alcohols were found in the cuticular lipids of larvae, pupae, males and females respectively. Only saturated alcohols with even-numbered carbon chains were present in these lipids. Only 1 alcohol (C22:0) was detected in the internal lipids of C. vomitoria larvae, while just 4 alcohols from - C18:0 to C24:0 - were identified in the internal lipids of pupae, and males and females. We also identified glycerol and cholesterol in the larvae, pupae, males and females of C. vomitoria. The individual alcohols and FAMEs, as well as their mixtures isolated from the cuticular and internal lipids of larvae, pupae, males and females of C. vomitoria, demonstrated antimicrobial activity against entomopathogenic fungi. PMID:23561808

Go??biowski, Marek; Cerkowniak, Magdalena; Dawgul, Ma?gorzata; Kamysz, Wojciech; Bogu?, Mieczys?awa I; Stepnowski, Piotr

2013-07-01

236

Digestion and absorption of polyunsaturated fatty acids  

E-print Network

Nutrition Summary― Polyunsaturated fatty acids play an important part in the structure and function linoleic or a-linolenic acids, and sea fish oils for eicosapentaenoic and docosahexaenoic acids. Because, and to some authors explains differences observed between vegetable and fish oil absorption. So additional

Boyer, Edmond

237

Polyhydroxy Fatty Acids Derived from Sophorolipids  

Technology Transfer Automated Retrieval System (TEKTRAN)

Starting from 17-hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 5 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups ca...

238

Cardiovascular benefits of omega-3 fatty acids  

Microsoft Academic Search

Cardiac societies recommend the intake of 1 g\\/day of the two omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) for cardiovascular disease prevention, treatment after a myocardial infarction, prevention of sudden death, and secondary prevention of cardiovascular disease. These recommendations are based on a body of scientific evidence that encompasses literally thousands of publications. Of four large scale

Clemens von Schacky; William S. Harris

2007-01-01

239

Dietary fatty acids and human health  

Microsoft Academic Search

A considerable amount of evidence has accumulated to support the view that the very long chain omega 3 fatty acids (eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)) have beneficial cardiovascular and anti-inflammatory properties and that levels of their consumption are insufficient in most Western diets. More recently, attention has been given to the possibility that the precursor omega-3 PUFA, alpha

Christine M. Williams

2000-01-01

240

Release of phospholipid fatty acid from human erythrocytes  

PubMed Central

To study the catabolism of erythrocyte phospholipids, human erythrocytes were labeled with radioactive fatty acid (FA). Labeling was performed by the two separate routes which together are thought to be responsible for the majority of phosphatide renewal in the red cell: (a) passive equilibration of erythrocytes with preformed acid-labeled red cell phosphatidylcholine (PC) and (b) active, “acylase”-dependent, incorporation of free fatty acid in the presence of ATP coenzyme A and magnesium. (As measured here “acylase” = the over-all effect of fatty acid thioesterification and the action of acyl-CoA: acylglycerophosphoryl acyltransferase.) The labeled cells were then reincubated in serum and the loss of radioactivity from cells into serum was examined. The phosphatide fatty acid introduced by these two routes was incorporated into two distinct cellular phosphatide pools with little mixing. The fatty acid in passively introduced phosphatidyl choline was released primarily as the intact phosphatide, whereas actively incorporated PC fatty acid was released primarily as free FA. As expected for an exchange process, the passively introduced PC was released at the same rate as it was introduced. However, the actively incorporated FA was released from the cell at a slower rate than its incorporation into PC. This latter phenomenon was explained by the observation of transfer of PC fatty acid to phosphatidyl ethanolamine and “neutral lipid” before its release to serum. This transfer process was inhibited by previous heating of the reincubation serum. The differences in the character of the released label, in the rate of release of the label, and in the influence of the reincubation serum all indicate separate pathways for the renewal of phosphatide introduced into red cells by these two routes. PMID:5449706

Shohet, Stephen B.

1970-01-01

241

Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin.  

PubMed

Our present investigation describes the regioselective enzymatic acylation of two series of acylated derivatives of phloridzin and isoquercitrin with six different long chain saturated, mono- and poly-unsaturated fatty acids. The biocatalytic synthesis was optimized to achieve 81-98% yields, using immobilized lipase B, from Candida antarctica (Novozym 435), in acetone at 45°C. The synthesized esters have been analyzed by (1)H NMR, (13)C NMR spectroscopy and evaluated for their antioxidant capacity and tyrosinase inhibition, using in vitro assays. Among all the phloridzin and isoquercitrin derivatives, the greatest potential for inhibition of tyrosinase activity (p ? 0.05) was exhibited by the ?-linolenic acid ester of isoquercitrin. PMID:23266182

Ziaullah; Bhullar, Khushwant S; Warnakulasuriya, Sumudu N; Rupasinghe, H P Vasantha

2013-02-01

242

Essential fatty acids of pitaya (dragon fruit) seed oil  

Microsoft Academic Search

Hylocereus undatus and Hylocereus polyrhizus are two varieties of the commonly called pitaya fruits. The seeds were separated and the oil was extracted and analysed. Essential fatty acids, namely, linoleic acid and linolenic acid form a significant percentage of the unsaturated fatty acids of the seed oil extract. Both pitaya varieties exhibit two oleic acid isomers. Essential fatty acids are

Abdul Azis Ariffin; Jamilah Bakar; Chin Ping Tan; Russly Abdul Rahman; Roselina Karim; Chia Chun Loi

2009-01-01

243

Short-Chain Fatty Acids Stimulate Angiopoietin-Like 4 Synthesis in Human Colon Adenocarcinoma Cells by Activating Peroxisome Proliferator-Activated Receptor ?  

PubMed Central

Angiopoietin-like protein 4 (ANGPTL4/FIAF) has been proposed as a circulating mediator between the gut microbiota and fat storage. Here, we show that transcription and secretion of ANGPTL4 in human T84 and HT29 colon adenocarcinoma cells is highly induced by physiological concentrations of short-chain fatty acids (SCFA). SCFA induce ANGPTL4 by activating the nuclear receptor peroxisome proliferator activated receptor ? (PPAR?), as demonstrated using PPAR? antagonist, PPAR? knockdown, and transactivation assays, which show activation of PPAR? but not PPAR? and PPAR? by SCFA. At concentrations required for PPAR? activation and ANGPTL4 induction in colon adenocarcinoma cells, SCFA do not stimulate PPAR? in mouse 3T3-L1 and human SGBS adipocytes, suggesting that SCFA act as selective PPAR? modulators (SPPARM), which is supported by coactivator peptide recruitment assay and structural modeling. Consistent with the notion that fermentation leads to PPAR activation in vivo, feeding mice a diet rich in inulin induced PPAR target genes and pathways in the colon. We conclude that (i) SCFA potently stimulate ANGPTL4 synthesis in human colon adenocarcinoma cells and (ii) SCFA transactivate and bind to PPAR?. Our data point to activation of PPARs as a novel mechanism of gene regulation by SCFA in the colon, in addition to other mechanisms of action of SCFA. PMID:23339868

Alex, Sheril; Lange, Katja; Amolo, Tom; Grinstead, Jeffrey S.; Haakonsson, Anders K.; Szalowska, Ewa; Koppen, Arjen; Mudde, Karin; Haenen, Daniëlle; Al-Lahham, Sa'ad; Roelofsen, Han; Houtman, René; van der Burg, Bart; Mandrup, Susanne; Bonvin, Alexandre M. J. J.; Kalkhoven, Eric; Müller, Michael; Hooiveld, Guido J.

2013-01-01

244

Association of serum aryl hydrocarbon receptor activity and RBC omega-3 polyunsaturated fatty acids with flow-mediated dilation in healthy, young Hispanic cigarette smokers.  

PubMed

Impaired flow-mediated dilation (FMD) occurs prior to clinical disease in young cigarette smokers. We investigated two potential biomarkers of FMD: serum aryl hydrocarbon receptor (AHR) activity and RBC omega-3 polyunsaturated fatty acids in healthy young Hispanic cigarette smokers. We recruited never (n=16) and current (n=16) Hispanic smokers (32±7 years old), excluding individuals with clinical cardiovascular disease. We measured FMD with duplex ultrasound, RBC fatty acids and serum AHR activity using a luciferase reporter assay. FMD was significantly impaired in smokers (5.8±4%) versus never smokers (12.3±7.4%, p=0.001). Serum AHR activity was significantly increased in smokers (1467±358 relative light units (RLU)) versus never smokers (689±251 RLU, p<0.001), and correlated positively with FMD only in smokers (r=0.691, p<0.004). RBC percentage of ?-linolenic acid (ALA%) was significantly increased in smokers (0.14±0.03%) versus never smokers (0.11±0.03%, p=0.018), and correlated inversely with FMD only in smokers (r=-0.538, p=0.03). The combination of serum AHR activity, ALA%, and systolic blood pressure significantly correlated with FMD in a multivariable regression model (r=0.802, p<0.008). These results suggest that serum AHR activity and RBC ALA% could serve as biomarkers of FMD in healthy, young Hispanic cigarette smokers. PMID:25482063

Wiest, Elani F; Warneke, Alex; Walsh, Mary T; Langsfeld, Mark; Anderson, Joe; Walker, Mary K

2015-01-22

245

[The fatty acids in blood plasma and erythrocytes in test of glucose tolerance].  

PubMed

The sample of 26 patients with ischemic heart disease and syndrome of insulin resistance was subjected to standard test of glucose tolerance. The content of individual fatty acids was detected using technique of gas chromatography and mass spectrometry. In blood plasma, after 2 hours of post-prandial hyperglycemia, reliably decreased content of C 16:1 of palmitoleic mono fatty acid, C 18:1 oleic mono fatty acid and in a lesser degree C 18:2 linoleic unsaturated fatty acid (p < 0.05). The level C 14:0 of myristic unsaturated fatty acid, C 16:0 of palmitic unsaturated fatty acid and with 18:0 of stearic unsaturated fatty acid, ratio C 16:0/C 16:1 and C 18:0/C 18:1 had no changes: content of both (omega-6 C 20:3 digomo-gamma-linoleic unsaturated fatty acid and essential polyenoic fatty acids remained the same. The significant differences between initial content in blood plasma of palmitic saturated fatty acid and oleic monoenic fatty acid was noted. The alteration in content of fatty acids in membranes of erythrocytes is the most expressed. In erythrocytes reliable (p < or = 0.05) decrease of content of C 16:0 palmitic fatty acid, C 18:0 stearic fatty acid and C 18:1 oleic fatty acid is established. The reliable decrease is noted in content of linoleic unsaturated fatty acid. In erythrocytes, moderate decrease is detected in levels of C 20:4 arachidonic polyenoic fatty acid, C 20:5 eicosapentaenoic polyenoic fatty acid. It is assumed that under post-prandial hyperglycemia insulin regulates metabolism of fatty acids, blocks lipolysis, decreases in cytosol of cells content of oleic and palmitic fatty acids inform of acetyl-KoA and forces mitochondrions intensively oxidate acetyl-KoA formed from pyruvate, from GLU. On surface of membrane, insulin increases number of glucose carriers GLUT4. Hypoglycemic effect of insulin is mediated by regulation first of all of metabolism of fatty acids. Hyperglycemia and insulin are two phylogenetically different humoral regulators. Insulin initiates blockade of lipolysis in adipocytes and positioning on membrane GLUT4. Hyperglycemia passively (activated) increases absorption by cells GLU on gradient of concentration inter-cellular medium--cytosol and synthesis of glycogen. PMID:25080793

Ameliushkina, V A; Aripovski?, A V; Titov, V N; Kaba, S I; Kotkina, T I; Parkhimovich, R M

2014-04-01

246

Milk Fatty Acids II: Prediction of the Production of Individual Fatty Acids in Bovine Milk  

Microsoft Academic Search

Previously observed relationships between dietary composition and production of a small number of indi- vidual milk fatty acids were the motivation to examine whetherequationscouldbedevelopedtopredictproduc- tion of all the major individual milk fatty acids. Such equations could be incorporated into ration formulation programs and used to examine factors that influence milk fat composition. Data from 29 published experi- ments onHolstein cows

P. J. Moate; W. Chalupa; R. C. Boston; I. J. Lean

2008-01-01

247

Evaluation of fatty acid content of some Iranian fast foods with emphasis on trans fatty acids  

Microsoft Academic Search

Although the disadvantages of trans fatty acids (TFAs) are widely mentioned, limited data are available on the TFAs contents of Iranian foods, including fast foods. The aim of this study was to quantify the amounts of com- mon fatty acids in several fast foods in Iran, with specific focus on TFAs. The most commonly consumed fast foods in Iran: sausage,

Seddigheh Asgary; Bahar Nazari; Nizal Sarrafzadegan; Sahar Parkhideh; Salbali Saberi; Ahmad Esmaillzadeh; Leila Azadbakht

2009-01-01

248

Production of hydroxylated fatty acids in genetically modified plants  

DOEpatents

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.

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

2011-08-23

249

Biocatalyst Engineering by Assembly of Fatty Acid Transport and Oxidation Activities for In Vivo Application of Cytochrome P-450BM-3 Monooxygenase  

PubMed Central

The application of whole cells containing cytochrome P-450BM-3 monooxygenase [EC 1.14.14.1] for the bioconversion of long-chain saturated fatty acids to ?-1, ?-2, and ?-3 hydroxy fatty acids was investigated. We utilized pentadecanoic acid and studied its conversion to a mixture of 12-, 13-, and 14-hydroxypentadecanoic acids by this monooxygenase. For this purpose, Escherichia coli recombinants containing plasmid pCYP102 producing the fatty acid monooxygenase cytochrome P-450BM-3 were used. To overcome inefficient uptake of pentadecanoic acid by intact E. coli cells, we made use of a cloned fatty acid uptake system from Pseudomonas oleovorans which, in contrast to the common FadL fatty acid uptake system of E. coli, does not require coupling by FadD (acyl-coenzyme A synthetase) of the imported fatty acid to coenzyme A. This system from P. oleovorans is encoded by a gene carried by plasmid pGEc47, which has been shown to effect facilitated uptake of oleic acid in E. coli W3110 (M. Nieboer, Ph.D. thesis, University of Groningen, Groningen, The Netherlands, 1996). By using a double recombinant of E. coli K27, which is a fadD mutant and therefore unable to consume substrates or products via the ?-oxidation cycle, a twofold increase in productivity was achieved. Applying cytochrome P-450BM-3 monooxygenase as a biocatalyst in whole cells does not require the exogenous addition of the costly cofactor NADPH. In combination with the coenzyme A-independent fatty acid uptake system from P. oleovorans, cytochrome P-450BM-3 recombinants appear to be useful alternatives to the enzymatic approach for the bioconversion of long-chain fatty acids to subterminal hydroxylated fatty acids. PMID:9758800

Schneider, Silke; Wubbolts, Marcel G.; Sanglard, Dominique; Witholt, Bernard

1998-01-01

250

Omega3 Fatty Acids in the Treatment of Psychiatric Disorders  

Microsoft Academic Search

recognised and there is increasing evidence that omega-3 fatty acids may also be important to mental health. The two main omega-3 fatty acids in fish oil, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have important biological functions in the CNS. DHA is a major structural component of neuronal membranes, and changing the fatty acid composition of neuronal membranes leads to

Malcolm Peet; Caroline Stokes

2005-01-01

251

Changes in Fatty Acid Metabolism after Erythrocyte Peroxidation: Stimulation of a Membrane Repair Process  

PubMed Central

To study certain membrane repair processes in human erythrocytes, vitamin E-deficient cells were incubated with hydrogen peroxide. The incorporation of exogenous fatty acid and the transfer of fatty acid from phosphatidylcholine and neutral lipid into phosphatidylethanolamine were examined using radioactive fatty acids. Hydrogen peroxide stimulated the incorporation of fatty acid into all membrane phospholipids. The specific activity of phosphatidylethanolamine was increased disproportionately. The lipids of the membranes of erythrocytes were labeled with saturated and unsaturated fatty acid. When these erythrocytes were subsequently incubated with hydrogen peroxide, both types of fatty acid were transferred from superficial erythrocyte neutral lipids into phosphatidylethanolamine. However, the unsaturated fatty acids of phosphatidylethanolamine were subsequently altered by hydrogen peroxide, whereas the saturated fatty acids were not. The cumulative effect of these processes was a relative decrease in unsaturated fatty acid and an increase in saturated fatty acid in the phosphatidylethanolamine of the erythrocyte membrane. The net effect of these events represents the operation of repair processes which distort the usual fatty acid composition of erythrocyte membranes in the presence of H2O2. This distortion may contribute to membrane permeability changes which occur during peroxide exposure and which precede the eventual hemolysis of these cells. Images PMID:5009118

Lubin, Bertram H.; Shohet, Stephen B.; Nathan, David G.

1972-01-01

252

Effects of conjugated linoleic acid. 1. Fatty acid modification of yolks and neonatal fatty acid metabolism.  

PubMed

The purpose of this study was to evaluate the effects of conjugated linoleic acids (CLA) on neonatal fatty acid metabolism. In this study, layer hens (n = 40) were divided into four equal groups and subjected to the following treatments. Group A served as the control group, Group B received 1 g CLA every other day, Group C received 1 g CLA every 4th d, and Group D was sham-supplemented with 1 g safflower oil every other day. After 4 mo of feeding, Group B hens exhibited an increase in BW and egg size; however, there were no differences noted in feed consumption among the various treatment groups. At the same time, hens were inseminated with a constant dose of pooled rooster semen to evaluate changes in chick liver and yolk fatty acid metabolism during neonatal growth. At hatch and through 6 d of age, there were no significant differences in breakout data (fertility and numbers of early-, mid-, or late-dead chicks) or chick BW, respectively. However, Group B chicks exhibited an increase in liver 18:3n3 and 22:1n9 and a decrease in 20:3n6 and 22:5n3 fatty acids when compared with chicks from Groups A and D. Also noted for Group B chicks, yolk 18:0 fatty acid was higher than that for Group A and D chicks. These results suggest that CLA alters lipid metabolism in growing chicks. PMID:10875761

Latour, M A; Devitt, A A; Meunier, R A; Stewart, J J; Watkins, B A

2000-06-01

253

Impact of dietary fatty acids on metabolic activity and host intestinal microbiota composition in C57BL/6J mice.  

PubMed

Different dietary fat and energy subtypes have an impact on both the metabolic health and the intestinal microbiota population of the host. The present study assessed the impact of dietary fat quality, with a focus on dietary fatty acid compositions of varying saturation, on the metabolic health status and the intestinal microbiota composition of the host. C57BL/6J mice (n 9-10 mice per group) were fed high-fat (HF) diets containing either (1) palm oil, (2) olive oil, (3) safflower oil or (4) flaxseed/fish oil for 16 weeks and compared with mice fed low-fat (LF) diets supplemented with either high maize starch or high sucrose. Tissue fatty acid compositions were assessed by GLC, and the impact of the diet on host intestinal microbiota populations was investigated using high-throughput 16S rRNA sequencing. Compositional sequencing analysis revealed that dietary palm oil supplementation resulted in significantly lower populations of Bacteroidetes at the phylum level compared with dietary olive oil supplementation (P< 0·05). Dietary supplementation with olive oil was associated with an increase in the population of the family Bacteroidaceae compared with dietary supplementation of palm oil, flaxseed/fish oil and high sucrose (P< 0·05). Ingestion of the HF-flaxseed/fish oil diet for 16 weeks led to significantly increased tissue concentrations of EPA, docosapentaenoic acid and DHA compared with ingestion of all the other diets (P< 0·05); furthermore, the diet significantly increased the intestinal population of Bifidobacterium at the genus level compared with the LF-high-maize starch diet (P< 0·05). These data indicate that both the quantity and quality of fat have an impact on host physiology with further downstream alterations to the intestinal microbiota population, with a HF diet supplemented with flaxseed/fish oil positively shaping the host microbial ecosystem. PMID:24555449

Patterson, Elaine; O' Doherty, Robert M; Murphy, Eileen F; Wall, Rebecca; O' Sullivan, Orla; Nilaweera, Kanishka; Fitzgerald, Gerald F; Cotter, Paul D; Ross, R Paul; Stanton, Catherine

2014-02-20

254

The combined effects on neuronal activation and blood-brain barrier permeability of time and n-3 polyunsaturated fatty acids in mice, as measured in vivo using MEMRI.  

PubMed

N-3 polyunsaturated fatty acids (n-3 PUFA) are known to have cardiovascular and neuroprotective properties in both humans and rodents. Here, we use manganese-enhanced magnetic resonance imaging (MEMRI) to compare the effects of these polyunsaturated fatty acids on the combined effects of neuronal activity and integrity of blood-brain barrier integrity with saturated fatty acids from buttermilk. C57BL/6 mice (4 weeks old) were fed isocaloric diets containing 3% fish oil (3% FO, n=5), 12% fish oil (FO, n=6), 3% buttermilk (3% BM, n=6) or 12% buttermilk (12% BM, n=6) for 6 months. Following metabolic cage analysis these mice were scanned using a standard MEMRI protocol at 28-32 weeks of age. Adult mice aged 28-32 weeks old (RM3, n=5) and 15-16 weeks old (YRM3, n=4) maintained on standard rodent chow were also studied to assess age-related changes in brain barrier systems and neuronal activity. Signal intensity (SI) in the anterior pituitary (AP), arcuate hypothalamic nucleus (ARC), ventromedial hypothalamic nucleus (VMH) and the paraventricular hypothalamic nucleus (PVN) was significantly reduced in young compared to older mice fed standard chow. Furthermore, fish oil supplementation led to a decrease in SI within the ARC and PVN, reaching significance in the VMH in age-matched controls. Interestingly, both fish oil and buttermilk supplementation resulted in a significant increase in SI within the AP, a structure outside the BBB. We conclude that MEMRI is able to detect the combined effects of the integrity of neuronal activity and blood-brain barrier permeability in the hypothalamus associated with dietary manipulation and aging. PMID:20097292

Kuo, Yu-Ting; So, Po-Wah; Parkinson, James R; Yu, Wei Sheng; Hankir, Mohammad; Herlihy, Amy H; Goldstone, Anthony P; Frost, Gary S; Wasserfall, Clive; Bell, Jimmy D

2010-05-01

255

Dietary fatty acid intakes and the risk of ovulatory infertility1-3  

Microsoft Academic Search

Background: Pharmacologic activation of the peroxisome proliferator-activated receptor (PPAR-) improves ovulatory function in women with polycystic ovary syndrome, and specific dietary fatty acids can affect PPAR- activity. Objective: The objective of the study was to assess whether the intakes of total fat, cholesterol, and major types of fatty acids affect the risk of ovulatory infertility. Design: We conducted a prospective

Jorge E Chavarro; Janet W Rich-Edwards; Bernard A Rosner; Walter C Willett

256

Milk fatty acids II: prediction of the production of individual fatty acids in bovine milk.  

PubMed

Previously observed relationships between dietary composition and production of a small number of individual milk fatty acids were the motivation to examine whether equations could be developed to predict production of all the major individual milk fatty acids. Such equations could be incorporated into ration formulation programs and used to examine factors that influence milk fat composition. Data from 29 published experiments on Holstein cows that provided 120 dietary treatments were entered into CPM-Dairy to obtain estimates of amounts of individual long-chain fatty acids (LCFA) absorbed from the intestines. These derived data and other dietary and animal data including the reported fatty acid composition of milk fat were entered into a spreadsheet. Descriptors of diet included daily intake of dry matter, total fermentable carbohydrate, total fatty acids, and profile of dietary fatty acids, intake of neutral detergent fiber, supplemental fish-oil, buffer, and magnesium oxide. Cow data included body weight and days in milk (DIM). Multiple linear regression was used to develop equations to predict the production (g/d) of each of 26 major LCFA. The equations developed generally had R(2) values in excess of 0.5. Production (g/d) of total de novo fatty acids (C4:0 to C15:0) (PTdenovo) was found to be positively related to the intake of fermentable carbohydrate, and negatively related to the intake of fish oil fatty acids and the estimated total amount of unsaturated fatty acids absorbed from the intestines. The PTdenovo was greater in pasture-fed cows than total mixed ration-fed cows and was negatively related to the square root of DIM. Production of each individual de novo fatty acid was described by a fixed proportion of PTdenovo. These proportions were 0.12 +/- 0.006 (C4:0), 0.083 +/- 0.0039 (C6:0), 0.0516 +/- 0.0025 (C8:0), 0.111 +/- 0.003 (C10:0), 0.134 +/- 0.0037 (C12:0), 0.441 +/- 0.007 (C14:0), 0.046 +/- 0.0024 (C14:1), and 0.0432 +/- 0.0017 (C15:0). Separate independent equations were developed to describe the daily production of C16:0, C16:1, and the main individual preformed fatty acids (>C16). The productions of each of the main individual pre-formed fatty acids were generally strongly related to the corresponding estimated amount (g/d) of specific fatty acids absorbed from the intestines. Percentage estimates for the direct transfer of the major absorbed LCFA to their corresponding LCFA in milk were 42% (C16:0); 9.5% (C18:0); 47.5% (cis-9 C18:1); 16.1% (all isomers of trans-C18:1), 38% (cis-9, cis-12 C18:2); and 31% (cis-9, cis-12, cis15 C18:3). High dietary intake of fish oil fatty acids was negatively associated with the production of all of the major individual preformed fatty acids with the exception of C20:5 and C22:6. In some instances, particular dietary factors were found to have positive influences on production of one fatty acid and negative influences on another. For example, high levels of dietary magnesium oxide were positively associated with production of C17 fatty acids but negatively associated with production of C18:0 and cis-9, trans-11 C18:2 (conjugated linoleic acid). This analysis quantified effects of major dietary and cow factors on production of individual fatty acids in milk. PMID:18292274

Moate, P J; Chalupa, W; Boston, R C; Lean, I J

2008-03-01

257

Synthesis and utilization of fatty acids by wild-type and fatty acid auxotrophs of Caulobacter crescentus.  

PubMed Central

The fatty acid composition of the dimorphic bacterium Caulobacter crescentus was found to consist primarily of 16- and 18-carbon fatty acids, both saturated and monounsaturated, in agreement with the findings of Chow and Schmidt (J. Gen. Microbiol. 83:359-373, 1974). In addition, two minor but as yet unidentified fatty acids were detected. Chromatographic mobilities suggested that these fatty acids may be a cyclopropane and a branched-chain fatty acid. In addition, we demonstrated that the fatty acid composition of wild-type C. crescentus can be altered by growing the cells in medium supplemented with any one of a variety of unsaturated fatty acids. Linoleic acid, a diunsaturated fatty acid which is not synthesized by C. crescentus, was incorporated into phospholipids without apparent modification. In addition, we found that C. crescentus, like Escherichia coli, synthesizes vaccenic acid (18:1 delta 11,cis) rather than oleic acid (18:1 delta 9,cis). This result allowed us to deduce that the mechanism of fatty acid desaturation in C. crescentus is anaerobic, as it is in E. coli. Finally, we examined the fatty acid biosynthesis and composition of two unsaturated fatty acid auxotrophs of C. crescentus. Neither of these mutants resembled the E. coli unsaturated fatty acid auxotrophs, which have defined enzymatic lesions in fatty acid biosynthesis. Rather, the mutants appeared to have defects relating to the complex coordination of membrane biogenesis and cell cycle events in C. crescentus. Images PMID:7107555

Letts, V; Shaw, P; Shapiro, L; Henry, S

1982-01-01

258

Fatty acid composition of Swedish bakery products, with emphasis on trans-fatty acids.  

PubMed

Trans-fatty acids (TFA) have been associated with increased risk of coronary heart disease, by affecting blood lipids and inflammation factors. Current nutrition recommendations emphasise a limitation of dietary TFA intake. The aim of this study was to investigate fatty acid composition in sweet bakery products, with emphasis on TFA, on the Swedish market and compare fatty acid composition over time. Products were sampled in 2001, 2006 and 2007 and analysed for fatty acid composition by using GC. Mean TFA levels were 0.7% in 2007 and 5.9% in 2001 of total fatty acids. In 1995-97, mean TFA level was 14.3%. In 2007, 3 of 41 products had TFA levels above 2% of total fatty acids. TFA content had decreased in this product category, while the proportion of saturated (SFA) and polyunsaturated (PUFA) fatty acids had increased, mostly through increased levels of 16:0 and 18:2 n-6, respectively. The total fat content remained largely unchanged. PMID:25577101

Trattner, Sofia; Becker, Wulf; Wretling, Sören; Öhrvik, Veronica; Mattisson, Irene

2015-05-15

259

Synthesis and Structure-activity Relationship Studies of O-Biphenyl-3-yl Carbamates as Peripherally Restricted Fatty Acid Amide Hydrolase Inhibitors  

PubMed Central

The peripherally restricted fatty acid amide hydrolase (FAAH) inhibitor URB937 (3, cyclohexylcarbamic acid 3’-carbamoyl-6-hydroxybiphenyl-3-yl ester) is extruded from the brain and spinal cord by the Abcg2 efflux transporter. Despite its inability to enter the central nervous system (CNS), 3 exerts profound antinociceptive effects in mice and rats, which result from the inhibition of FAAH in peripheral tissues and the consequent enhancement of anandamide signaling at CB1 cannabinoid receptors localized on sensory nerve endings. In the present study, we examined the structure-activity relationships (SAR) for the biphenyl region of compound 3, focusing on the carbamoyl and hydroxyl groups in the distal and proximal phenyl rings. Our SAR studies generated a new series of peripherally restricted FAAH inhibitors and identified compound 35 (cyclohexylcarbamic acid 3’-carbamoyl-5-hydroxybiphenyl-3-yl ester) as the most potent brain-impermeant FAAH inhibitor disclosed to date. PMID:23822179

Moreno-Sanz, Guillermo; Duranti, Andrea; Melzig, Laurin; Fiorelli, Claudio; Ruda, Gian Filippo; Colombano, Giampiero; Mestichelli, Paola; Sanchini, Silvano; Tontini, Andrea; Mor, Marco; Bandiera, Tiziano; Scarpelli, Rita; Tarzia, Giorgio; Piomelli, Daniele

2014-01-01

260

Fatty acid relationship in an aquatic food chain  

Microsoft Academic Search

The relationships amongst the fatty acids of the lipids from members of a model aquatic food chain were examined. The basic\\u000a pattern of the fatty acids in the members, algae-brine shrimp-hydra, originated in the phytoplankton. Fatty acids in the neutral\\u000a lipids of adult brine shrimp,Artemia salina, closely resembled dietary, or algal, fatty acids, whereas the phospholipid acids differed considerably from

Peter F. Jezyk; A. John Penicnak

1966-01-01

261

Enrichment of maternal diet with conjugated linoleic acids influences desaturases activity and fatty acids profile in livers and hepatic microsomes of the offspring with 7,12-dimethylbenz[a]anthracene-induced mammary tumors.  

PubMed

The aim of this study was to assess the influence of diet supplementation of pregnant and breast-feeding female Sprague-Dawley rats with conjugated linoleic acids (CLA) on the ?6- and ?5-desaturase activity in hepatic microsomes as well as on fatty acids profile and lipids peroxidation in liver and hepatic microsomes of the progeny with chemically induced mammary tumors. Rats were divided into two groups with different diet supplementation (vegetable oil (which did not contain CLA) or CLA). Their female offspring was divided within these groups into two subgroups: (1)--fed the same diet as mothers (K1 - oil, 01 - CLA), and (2)--fed the standard fodder (K2, O2). At 50th day of life, the progeny obtained carcinogenic agent (7,12-dimethylbenz[a]anthracene). Higher supply of CLA in diet of mothers resulted in lower susceptibility to chemically induced mammary tumors in their offspring (p = 0.0322). It also influenced the fatty acids profile in livers and in hepatic microsomes, especially polyunsaturated n3 and n6 fatty acids. CLA inhibited the activity of the desaturases, which confirmed that CLA can reduce the level of arachidonic acid directly, reducing linoleic acid content in membranes, or indirectly, through the regulation of its metabolism. We were unable to confirm or deny the antioxidative properties of CLA. Our results indicate that the higher supply of CLA in mothers' diet during pregnancy and breastfeeding causes their incorporation into tissues of children, changes the efficiency of fatty acids metabolism and exerts health-promoting effect in their adult life reducing the breast cancer risk. PMID:25362803

Bia?ek, Agnieszka; Stawarska, Agnieszka; Tokarz, Andrzej; Czuba, Katarzyna; Konarska, Anna; Mazurkiewicz, Magdalena

2014-01-01

262

[Role of fatty acids in sperm membrane].  

PubMed

One of causes of male infertility is reduced sperm motility. Reactive oxygen species (ROS) play significant role for physiological sperm function. Oxidative stress occurs when the production of potentially destructive ROS exceeds the natural antioxidant defences, resulting in cell damage. Sperm phospholipid polyunsaturated fatty acids are particularly susceptible to peroxidative damage by free radicals. Detrimental effects of lipid peroxidation should decrease sperm quality and be responsible of fertility problems. The review deals with sperm membrane composition, importance of fatty acids and prevention possibilities of oxidative cell damage. PMID:24874823

Stramová, X; Hampl, R; St?pán, J; Kan?ár, R

2014-04-01

263

Fatty acid profiles of invertebrate iridescent viruses.  

PubMed

Eight invertebrate iridescent viruses (IVs) from diverse host taxa were grown in a common lepidopteran host, Galleria mellonella. The lipid composition of purified virus was assessed by fatty acid methyl esterase (FAME) analysis using a gas-liquid chromatograph. IV fatty acid profiles were markedly different from those of the host tissues. The interrelationships among the IVs did not follow previous serological and genetic findings. We conclude that FAME analysis is not a useful technique for revealing phylogenetic relationships among these viruses. PMID:7605209

Williams, T; Thompson, I P

1995-01-01

264

Effect of n-3 fatty acids on serum lipid levels and hepatic fatty acid metabolism in BALB/c.KOR-Apoeshl mice deficient in apolipoprotein E expression.  

PubMed

N-3 fatty acids exert a potent serum lipid-lowering effect in rodents mainly by affecting hepatic fatty acid oxidation and synthesis. However, it has been observed that fish oil and docosahexaenoic acid ethyl ester do not lower serum lipid levels in apolipoprotein E (apoE)-knockout (Apoetm1Unc) mice generated by gene targeting. To test the hypothesis that apoE expression is required for n-3 fatty acid-dependent regulation of serum lipid levels and hepatic fatty acid metabolism, we examined the effect of fish oil and n-3 fatty acid ethyl esters on the activity and gene expression of hepatic enzymes involved in fatty acid oxidation and synthesis using an alternative apoE-deficient mouse model with the BALB/c genetic background (BALB/c.KOR-Apoeshl). ApoE-deficient mice were fed diets containing 9.4% palm oil, fish oil, or 5.4% palm oil and 1% EPA plus 3% DHA ethyl esters for 15 days. In contrast to the reported data on apoE-knockout mice, fish oil and n-3 fatty acid ethyl esters greatly decreased serum triacylglycerol, cholesterol, and phospholipid levels in the Apoeshl mice. The decreases were greater with fish oil than with ethyl esters. The alterations by dietary n-3 fatty acids of serum lipid levels were accompanied by parallel changes in the activity and mRNA levels of enzymes involved in hepatic fatty acid oxidation and synthesis. The reason for the discrepancy between the results of the current study and previous studies is unknown. However, our study at least indicates that a lack of apoE expression does not necessarily accompany deficits in the n-3 fatty acid-dependent regulation of serum lipid levels and hepatic fatty acid metabolism. PMID:15023399

Ide, Takashi; Takahashi, Yoko; Kushiro, Masayo; Tachibana, Masayoshi; Matsushima, Yoshibumi

2004-03-01

265

Flaxseed supplementation improves fatty acid profile of cow milk.  

PubMed

The objective of the study was to determine the effects of adding flaxseed or fish oil to the diet on the milk fatty acid profile of cows. The experiment was conducted in the summer of 2006 and involved 24 Friesian cows that were divided into 3 groups of 8 animals according to different type of fat supplementation: a traditional diet with no fat supplementation, a diet supplemented with whole flaxseed, and a diet supplemented with fish oil. Results suggested that whole flaxseed supplementation positively affects the milk fatty acid profile during summer. In particular, milk from cows receiving flaxseed supplementation showed a decrease in saturated fatty acid, an increase in monounsaturated fatty acid, and, together with the milk from fish oil-supplemented cows, an increase in polyunsaturated fatty acid content compared with milk from control cows. As expected, both fish oil and flaxseed supplementation increased the content of n-3 polyunsaturated fatty acids in milk fat. The increased dietary intake of C18:3 in flaxseed-supplemented cows resulted in increased levels of milk C18:1 trans-11 and increased conjugated linoleic acid C18:2 cis-9,trans-11 by Delta(9)-desaturase activity. Milk from flaxseed-supplemented cows together with the high conjugated linoleic acid content was characterized by low atherogenic and thrombogenic indices, suggesting that its use has less detrimental effects concerning the atherosclerosis and coronary thrombosis risk associated with the consumption of milk and dairy products. In conclusion, flaxseed supplementation improves composition and nutritional properties of milk from cows milked during times of high ambient temperature. PMID:20494167

Caroprese, M; Marzano, A; Marino, R; Gliatta, G; Muscio, A; Sevi, A

2010-06-01

266

THREE MICROSOMAL OMEGA-3 FATTY ACID DESATURASE GENES CONTRIBUTE TO SOYBEAN LINOLENIC ACID LEVELS  

Technology Transfer Automated Retrieval System (TEKTRAN)

Three independent genetic loci have been shown to contribute to soybean (Glycine max L.) seed linolenic acid levels, including the well-characterized Fan locus. Linolenic acid is the product of omega-3-fatty acid desaturase enzyme activity. The objective of this study was to identify and character...

267

Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis  

SciTech Connect

Cyclopropane fatty acids (CPA) have been found in certain gymnosperms, Malvales, Litchi and other Sapindales. The presence of their unique strained ring structures confers physical and chemical properties characteristic of unsaturated fatty acids with the oxidative stability displayed by saturated fatty acids making them of considerable industrial interest. While cyclopropenoid fatty acids (CPE) are well-known inhibitors of fatty acid desaturation in animals, CPE can also inhibit the stearoyl-CoA desaturase and interfere with the maturation and reproduction of some insect species suggesting that in addition to their traditional role as storage lipids, CPE can contribute to the protection of plants from herbivory. Three genes encoding cyclopropane synthase homologues GhCPS1, GhCPS2 and GhCPS3 were identified in cotton. Determination of gene transcript abundance revealed differences among the expression of GhCPS1, 2 and 3 showing high, intermediate and low levels, respectively, of transcripts in roots and stems; whereas GhCPS1 and 2 are both expressed at low levels in seeds. Analyses of fatty acid composition in different tissues indicate that the expression patterns of GhCPS1 and 2 correlate with cyclic fatty acid (CFA) distribution. Deletion of the N-terminal oxidase domain lowered GhCPS's ability to produce cyclopropane fatty acid by approximately 70%. GhCPS1 and 2, but not 3 resulted in the production of cyclopropane fatty acids upon heterologous expression in yeast, tobacco BY2 cell and Arabidopsis seed. In cotton GhCPS1 and 2 gene expression correlates with the total CFA content in roots, stems and seeds. That GhCPS1 and 2 are expressed at a similar level in seed suggests both of them can be considered potential targets for gene silencing to reduce undesirable seed CPE accumulation. Because GhCPS1 is more active in yeast than the published Sterculia CPS and shows similar activity when expressed in model plant systems, it represents a strong candidate gene for CFA accumulation via heterologous expression in production plants.

Yu X. H.; Shanklin J.; Rawat, R.

2011-05-01

268

Fatty acid composition and cyclopropene fatty acid content of China-chestnuts ( Sterculia monosperma , ventenat)  

Microsoft Academic Search

The China-chestnuts (Sterculia monosperma, Ventenat) were examined for their fatty acid composition by gas liquid chromatography, infrared and nuclear magnetic resonance\\u000a spectroscopy. The oil in nuts contained cyclopropene fatty acids (CPFA) determined as silver nitrate derivatives of their\\u000a esters. The values (area %) for the major fatty acids as methyl esters were 23.47% C16:0, 1.25% C16:1, 2.56% C18:0, 24.89%\\u000a C18:1,

S. K. Berry

1982-01-01

269

The mitochondrial fatty acid synthesis (mtFASII) pathway is capable of mediating nuclear-mitochondrial cross talk through the PPAR system of transcriptional activation  

SciTech Connect

Highlights: •The function of the mitochondria fatty acid synthesis pathway is partially unknown. •Overexpression of the pathway causes transcriptional activation through PPARs. •Knock down of the pathway attenuates that activation. •The last enzyme in the pathway regulates its own transcription. •Products of the mtFASII pathway are able to drive nuclear transcription. -- Abstract: Mammalian cells contain two fatty acid synthesis pathways, the cytosolic FASI pathway, and the mitochondrial FASII pathway. The selection behind the conservation of the mitochondrial pathway is not completely understood, given the presence of the cytosolic FAS pathway. In this study, we show through heterologous gene reporter systems and PCR-based arrays that overexpression of MECR, the last step in the mtFASII pathway, causes modulation of gene expression through the PPAR pathway. Electromobility shift assays (EMSAs) demonstrate that overexpression of MECR causes increased binding of PPARs to DNA, while cell fractionation and imaging studies show that MECR remains localized to the mitochondria. Interestingly, knock down of the mtFASII pathway lessens the effect of MECR on this transcriptional modulation. Our data are most consistent with MECR-mediated transcriptional activation through products of the mtFASII pathway, although we cannot rule out MECR acting as a coactivator. Further investigation into the physiological relevance of this communication will be necessary to better understand some of the phenotypic consequences of deficits in this pathway observed in animal models and human disease.

Parl, Angelika; Mitchell, Sabrina L.; Clay, Hayley B.; Reiss, Sara; Li, Zhen; Murdock, Deborah G., E-mail: deborah.murdock@vanderbilt.edu

2013-11-15

270

A new ester of fatty acid from a methanol extract of the whole plant of Amaranthus spinosus and its ?-glucosidase inhibitory activity.  

PubMed

Abstract Context: Amaranthus spinosus Linn. (Amaranthaceae), commonly known as "spiny pigweed", is used both in the Indian traditional system and in folk medicine to treat diabetes. Objective: The present study evaluates the scientific basis of antidiabetic activity of chloroform fraction of methanol extract of A. spinosus and of an isolated constituent of A. spinosus. Materials and methods: HPLC analysis was performed to determine the purity and the amount of the constituent present in the plant extract. The yeast ?-glucosidase inhibition technique was used to determine the antidiabetic activity of A. spinosus. Acarbose was used as a standard. An appropriate therapeutic approach for preventing diabetes mellitus and obesity is to retard the absorption of glucose by inhibition of ?-glucosidase. Results: One novel fatty acid with strong ?-glucosidase inhibitory activity - (14E, 18E, 22E, 26E) - methyl nonacosa-14, 18, 22, 26 tetraenoate [1] (IC50 value 6.52?µM/mL) and ?-sitosterol [2] were purified. Compound 1 was found to be more potent than the methanol extract. HPLC quantative analysis revealed that 0.15% of compound 1 and 0.06% of compound 2 were present in the plant extract. Conclusion: This novel fatty acid can potentially be developed as a novel natural nutraceutical for the management of diabetes. PMID:25339411

Mondal, Arijit; Guria, Tanmoy; Maity, Tapan Kumar

2014-10-23

271

Effect of dietary conjugated linoleic acid on the fatty acid composition of egg yolk, plasma and liver as well as hepatic stearoyl-coenzyme A desaturase activity and gene expression in laying hens.  

PubMed

A total of 216 Brown Dwarf laying hens (1.62 +/- 0.06 kg BW and 60 wk old) were fed 1 of 3 corn-soybean meal-based diets containing 0, 2.5, or 5.0% conjugated linoleic aicd (CLA) to explore its effects on the fatty acid composition of egg yolk, plasma, and liver as well as hepatic stearoyl-coenzyme A desaturase-1 (SCD-1) activity and its mRNA gene expression. Four hens were placed in wired-floored cages (45 x 40 x 45 cm) and 3 cages were grouped as 1 replicate, resulting in 6 replicates per treatment. The experimental diets were fed for 54 d, and then eggs were collected to determine the fatty acid composition of egg yolk. Four eggs were randomly selected from the total day's production for each replicate, and the contents were pooled prior to analysis. On d 56, one randomly chosen hen from each replicate (6 hens per replicate and a total of 18 hens) was bled via heart puncture and then killed in order to collect liver samples to measure the fatty acid profile of plasma and liver tissue as well as hepatic SCD-1 activity and its mRNA abundance. Dietary supplementation of CLA resulted in a significant deposition of CLA in egg yolk, plasma, and liver lipids (P < 0.01). As the dietary level of CLA increased, the concentration of saturated fatty acids in egg yolk, plasma, and liver also increased (P < 0.05). However, the concentration of monounsaturated fatty acids in these same tissues decreased (P < 0.01). Compared with the control, the activity of SCD-1 was reduced by feeding 2.5% CLA (P < 0.05) without a change in SCD-1 mRNA gene expression. However, feeding 5% CLA reduced both SCD-1 activity and mRNA abundance (P < 0.05). These results indicate that the conversion of saturated to monounsaturated fatty acids in egg yolk, plasma, and liver might be modulated directly at hepatic mRNA gene expression levels, or may be indirectly regulated at the downstream post-transcriptional levels. PMID:16479945

Shang, X G; Wang, F L; Li, D F; Yin, J D; Li, X J; Yi, G F

2005-12-01

272

Polyunsaturated fatty acids and inflammatory diseases.  

PubMed

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. PMID:12442911

Gil, A

2002-10-01

273

ACTIVATION OF VASCULAR ENDOTHELIAL NITRIC OXIDE SYNTHASE AND HEME OXYGENASE-1 EXPRESSION BY ELECTROPHILIC NITRO-FATTY ACIDS  

PubMed Central

Reactive oxygen species mediate a decrease in nitric oxide (NO) bioavailability and endothelial dysfunction, with secondary oxidized and nitrated byproducts of these reactions contributing to the pathogenesis of numerous vascular diseases. While oxidized lipids and lipoproteins exacerbate inflammatory reactions in the vasculature, in stark contrast the nitration of polyunsaturated fatty acids and complex lipids yield electrophilic products that exhibit pluripotent anti-inflammatory signaling capabilities acting via both cGMP-dependent and -independent mechanisms. Herein we report that nitro-oleic acid (OA-NO2) treatment increases expression of endothelial nitric oxide synthase (eNOS) and heme oxygenase 1 (HO-1) in the vasculature, thus transducing vascular protective effects associated with enhanced NO production. Administration of OA-NO2 via osmotic pump results in a significant increase in eNOS and HO-1 mRNA in mouse aortas. Moreover, HPLC-MS/MS analysis showed that NO2-FAs are rapidly metabolized in cultured endothelial cells (ECs) and treatment with NO2-FAs stimulated the phosphorylation of eNOS at Ser1179. These post-translational modifications of eNOS, in concert with elevated eNOS gene expression, contributed to an increase in endothelial NO production. In aggregate, OA-NO2-induced eNOS and HO-1 expression by vascular cells can induce beneficial effects on endothelial function and provide a new strategy for treating various vascular inflammatory and hypertensive disorders. PMID:19857569

Khoo, Nicholas K.H.; Rudolph, Volker; Cole, Marsha P.; Golin-Bisello, Franca; Schopfer, Francisco J.; Woodcock, Steven R.; Batthyany, Carlos; Freeman, Bruce A.

2010-01-01

274

21 CFR 862.1290 - Fatty acids test system.  

Code of Federal Regulations, 2010 CFR

...measure fatty acids in plasma and serum. Measurements of fatty acids are used in the diagnosis and treatment of various disorders of lipid metabolism. (b) Classification. Class I (general controls). The device is exempt from the premarket...

2010-04-01

275

Accumulation of Oxygenated Fatty Acids in Oat Lipids During Storage  

Technology Transfer Automated Retrieval System (TEKTRAN)

Oxygenated fatty acids were identified in oat grain by gas chromatography - mass spectrometry. We hypothesized that most of these were the results of lipoxygenase activity. This hypothesis was tested by measuring concentrations of these compounds after hydrothermal treatments and storage of oat groa...

276

Identification of bifunctional ?12/?3 fatty acid desaturases for improving the ratio of ?3 to ?6 fatty acids in microbes and plants  

PubMed Central

We report the identification of bifunctional ?12/?3 desaturases from Fusarium moniliforme, Fusarium graminearum, and Magnaporthe grisea. The bifunctional activity of these desaturases distinguishes them from all known ?12 or ?3 fatty acid desaturases. The ?3 desaturase activity of these enzymes also shows a broad ?6 fatty acid substrate specificity by their ability to convert linoleic acid (LA), ?-linolenic acid, di-homo-?-linolenic acid, and arachidonic acid to the ?3 fatty acids, ?-linolenic acid (ALA), stearidonic acid, eicosatetraenoic acid, and eicosapentaenoic acid (EPA), respectively. Phylogenetic analysis suggests that ?3 desaturases arose by independent gene duplication events from a ?12 desaturase ancestor. Expression of F. moniliforme ?12/?3 desaturase resulted in high ALA content in both Yarrowia lipolytica, an oleaginous yeast naturally deficient in ?3 desaturation, and soybean. In soybean, seed-specific expression resulted in 70.9 weight percent of total fatty acid (%TFA) ALA in a transformed seed compared with 10.9%TFA in a null segregant seed and 53.2%TFA in the current best source of ALA, linseed oil. The ALA/LA ratio in transformed seed was 22.3, a 110- and 7-fold improvement over the null segregant seed and linseed oil, respectively. Thus, these desaturases have potential for producing nutritionally desirable ?3 long-chain polyunsaturated fatty acids, such as EPA, with a significantly improved ratio of ?3/?6 long-chain polyunsaturated fatty acids in both oilseeds and oleaginous microbes. PMID:16763049

Damude, Howard G.; Zhang, Hongxiang; Farrall, Leonard; Ripp, Kevin G.; Tomb, Jean-Francois; Hollerbach, Dieter; Yadav, Narendra S.

2006-01-01

277

Modifying yolk fatty acid composition to improve the health quality of shell eggs  

E-print Network

were evaluated. The effects of consumption of n-3 fatty acid enriched eggs on human blood lipid parameters were also investigated. Dietary fat did not alter egg production parameters, total yolk fat or yolk cholesterol (CHOL). Yolk fatty acid... fatty acid consumption results in the production of leukotriene B, which is less biochemically active than the 4-series. Leukotriene B, formation is advantageous in reducing CHD risk in that an injury to the blood vessel wall is less likely...

Van Elswyk, Mary Elizabeth

2012-06-07

278

Opposite regulation of CD36 ubiquitination by fatty acids and insulin: effects on fatty acid uptake.  

PubMed

FAT/CD36 is a membrane scavenger receptor that facilitates long chain fatty acid uptake by muscle. Acute increases in membrane CD36 and fatty acid uptake have been reported in response to insulin and contraction. In this study we have explored protein ubiquitination as one potential mechanism for the regulation of CD36 level. CD36 expressed in Chinese hamster ovary (CHO) or HEK 293 cells was found to be polyubiquitinated via a process involving both lysines 48 and 63 of ubiquitin. Using CHO cells expressing the insulin receptor (CHO/hIR) and CD36, it is shown that addition of insulin (100 nm, 10 and 30 min) significantly reduced CD36 ubiquitination. In contrast, ubiquitination was strongly enhanced by fatty acids (200 microm palmitate or oleate, 2 h). Similarly, endogenous CD36 in C2C12 myotubes was ubiquitinated, and this was enhanced by oleic acid treatment, which also reduced total CD36 protein in cell lysates. Insulin reduced CD36 ubiquitination, increased CD36 protein, and inhibited the opposite effects of fatty acids on both parameters. These changes were paralleled by changes in fatty acid uptake, which could be blocked by the CD36 inhibitor sulfosuccinimidyl oleate. Mutation of the two lysine residues in the carboxyl-terminal tail of CD36 markedly attenuated ubiquitination of the protein expressed in CHO cells and was associated with increased CD36 level and enhanced oleate uptake and incorporation into triglycerides. In conclusion, fatty acids and insulin induce opposite alterations in CD36 ubiquitination, modulating CD36 level and fatty acid uptake. Altered CD36 turnover may contribute to abnormal fatty acid uptake in the insulin-resistant muscle. PMID:18353783

Smith, Jill; Su, Xiong; El-Maghrabi, Raafat; Stahl, Philip D; Abumrad, Nada A

2008-05-16

279

PLANT FATTY ACID (ETHANOL) AMIDE HYDROLASES  

Technology Transfer Automated Retrieval System (TEKTRAN)

Fatty acid amide hydrolase (FAAH) plays a central role in modulating endogenous N-acylethanolamine (NAE) levels in vertebrates, and, in part, constitutes an “endocannabinoid” signaling pathway that regulates diverse physiological and behavioral processes in animals. Recently, an Arabidopsis FAAH hom...

280

Trans Fatty Acids and Cardiovascular Disease  

Microsoft Academic Search

Trans fats, unsaturated fatty acids with at least one double bond in the trans configuration (Figure 1), are formed during the partial hydrogenation of vegetable oils, a process that converts vegetable oils into semisolid fats for use in margarines, commercial cooking, and manufacturing processes. From the perspective of the food industry, partially hydrogenated vegetable oils are attractive because of their

Dariush Mozaffarian; Martijn B. Katan; Alberto Ascherio; Meir J. Stampfer; Walter C. Willett

2006-01-01

281

Trans fatty acids and cardiovascular risk  

Microsoft Academic Search

The major source of trans unsaturated fatty acid bearing fats (trans fats) is the partially hydrogenated fats present in margarines, salad and cooking oils. When ingested, trans fats are deposited in tissues but disappear when the nutritional stimulus is removed. They have no adverse effects on growth or reproduction in rats. Trans fats are hypercholesterolemic for rabbits and monkeys but

D. Kritchevsky

1997-01-01

282

Surfactant partitioning in cloud droplet activation: a study of C8, C10, C12 and C14 normal fatty acid sodium salts  

NASA Astrophysics Data System (ADS)

We have measured critical supersaturations of dried single-component particles of sodium caprylate [CH3(CH2)6COONa], sodium caprate [CH3(CH2)8COONa], sodium laurate [CH3(CH2)10COONa] and sodium myristate [CH3(CH2)12COONa] in the diameter range 33-140 nm at 296 K using a static thermal gradient diffusion cloud condensation nucleus counter. These fatty acid sodium salts are surface active molecules which have all been identified in atmospheric aerosol particles. Experimental critical supersaturations increased systematically with increasing carbon chain length and were in the range 0.96-1.34% for particles with a dry diameter of 40 nm. The experimental data were modelled using Köhler theory modified to account for partitioning of the surface active fatty acid sodium salts between the droplet bulk and surface as well as Köhler theory including surface tension reduction without accounting for surfactant partitioning and Köhler theory using the surface tension of pure water. It was found that Köhler theory using the reduced surface tension with no account for surfactant partitioning underpredicts experimental critical supersaturations significantly, whereas Köhler theory modified to account for surfactant partitioning and Köhler theory using the surface tension of pure water reproduced the experimental data well.

Prisle, Nønne L.; Raatikainen, Tomi; Sorjamaa, Riikka; Svenningsson, Birgitta; Laaksonen, Ari; Bilde, Merete

2008-07-01

283

DIFFERENTIAL EFFECTS OF SATURATED AND UNSATURATED FATTY ACID DIETS ON CARDIOMYOCYTE APOPTOSIS, ADIPOSE DISTRIBUTION, AND SERUM LEPTIN  

Technology Transfer Automated Retrieval System (TEKTRAN)

Fatty acids are the primary fuel for the heart and are ligands for peroxisome proliferator-activated receptors (PPARs), which regulate the expression of genes encoding proteins involved in fatty acid metabolism. Saturated fatty acids, particularly palmitate, can be converted to the proapoptotic lipi...

284

Fatty acid composition of brown adipose tissue in genetically heat-tolerant FOK rats  

NASA Astrophysics Data System (ADS)

The phospholipid fatty acid composition of brown adipose tissue (BAT) was examined in inbred heat-tolerant FOK rats and compared with that in conventional Wistar rats not previously exposed to heat. The FOK rats showed higher unsaturation states, as indicated by higher levels of polyunsaturated fatty acids and a higher unsaturation index and polyunsaturated fatty acids/saturated fatty acids ratio. This higher level of unsaturation was characterized by the higher amount of polyunsaturated fatty acids such as linoleic acid, arachidonic acid and docosahexaenoic acid. It may be concluded that the increased docosahexaenoic acid level in BAT phospholipids brings about the hyperplasia of BAT, causing an enhancement of its in vivo thermogernic activity as well as the systemic non-shivering thermogenesis observed in heat-tolerant FOK rats.

Ohno, T.; Furuyama, F.; Kuroshima, A.

285

Diversity of ?12 fatty acid desaturases in santalaceae and their role in production of seed oil acetylenic fatty acids.  

PubMed

Plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum, accumulate ximenynic acid (trans-11-octadecen-9-ynoic acid) in their seed oil and conjugated polyacetylenic fatty acids in root tissue. Twelve full-length genes coding for microsomal ?12 fatty acid desaturases (FADs) from the two Santalaceae species were identified by degenerate PCR. Phylogenetic analysis of the predicted amino acid sequences placed five Santalaceae FADs with ?12 FADs, which include Arabidopsis thaliana FAD2. When expressed in yeast, the major activity of these genes was ?12 desaturation of oleic acid, but unusual activities were also observed: i.e. ?15 desaturation of linoleic acid as well as trans-?12 and trans-?11 desaturations of stearolic acid (9-octadecynoic acid). The trans-12-octadecen-9-ynoic acid product was also detected in quandong seed oil. The two other FAD groups (FADX and FADY) were present in both species; in a phylogenetic tree of microsomal FAD enzymes, FADX and FADY formed a unique clade, suggesting that are highly divergent. The FADX group enzymes had no detectable ?12 FAD activity but instead catalyzed cis-?13 desaturation of stearolic acid when expressed in yeast. No products were detected for the FADY group when expressed recombinantly. Quantitative PCR analysis showed that the FADY genes were expressed in leaf rather than developing seed of the native cherry. FADs with promiscuous and unique activities have been identified in Santalaceae and explain the origin of some of the unusual lipids found in this plant family. PMID:24062307

Okada, Shoko; Zhou, Xue-Rong; Damcevski, Katherine; Gibb, Nerida; Wood, Craig; Hamberg, Mats; Haritos, Victoria S

2013-11-01

286

Diversity of ?12 Fatty Acid Desaturases in Santalaceae and Their Role in Production of Seed Oil Acetylenic Fatty Acids*  

PubMed Central

Plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum, accumulate ximenynic acid (trans-11-octadecen-9-ynoic acid) in their seed oil and conjugated polyacetylenic fatty acids in root tissue. Twelve full-length genes coding for microsomal ?12 fatty acid desaturases (FADs) from the two Santalaceae species were identified by degenerate PCR. Phylogenetic analysis of the predicted amino acid sequences placed five Santalaceae FADs with ?12 FADs, which include Arabidopsis thaliana FAD2. When expressed in yeast, the major activity of these genes was ?12 desaturation of oleic acid, but unusual activities were also observed: i.e. ?15 desaturation of linoleic acid as well as trans-?12 and trans-?11 desaturations of stearolic acid (9-octadecynoic acid). The trans-12-octadecen-9-ynoic acid product was also detected in quandong seed oil. The two other FAD groups (FADX and FADY) were present in both species; in a phylogenetic tree of microsomal FAD enzymes, FADX and FADY formed a unique clade, suggesting that are highly divergent. The FADX group enzymes had no detectable ?12 FAD activity but instead catalyzed cis-?13 desaturation of stearolic acid when expressed in yeast. No products were detected for the FADY group when expressed recombinantly. Quantitative PCR analysis showed that the FADY genes were expressed in leaf rather than developing seed of the native cherry. FADs with promiscuous and unique activities have been identified in Santalaceae and explain the origin of some of the unusual lipids found in this plant family. PMID:24062307

Okada, Shoko; Zhou, Xue-Rong; Damcevski, Katherine; Gibb, Nerida; Wood, Craig; Hamberg, Mats; Haritos, Victoria S.

2013-01-01

287

Fatty acid-regulated transcription factors in the liver.  

PubMed

Fatty acid regulation of hepatic gene transcription was first reported in the early 1990s. Several transcription factors have been identified as targets of fatty acid regulation. This regulation is achieved by direct fatty acid binding to the transcription factor or by indirect mechanisms where fatty acids regulate signaling pathways controlling the expression of transcription factors or the phosphorylation, ubiquitination, or proteolytic cleavage of the transcription factor. Although dietary fatty acids are well-established regulators of hepatic transcription factors, emerging evidence indicates that endogenously generated fatty acids are equally important in controlling transcription factors in the context of glucose and lipid homeostasis. Our first goal in this review is to provide an up-to-date examination of the molecular and metabolic bases of fatty acid regulation of key transcription factors controlling hepatic metabolism. Our second goal is to link these mechanisms to nonalcoholic fatty liver disease (NAFLD), a growing health concern in the obese population. PMID:23528177

Jump, Donald B; Tripathy, Sasmita; Depner, Christopher M

2013-01-01

288

Fatty Acid–Regulated Transcription Factors in the Liver  

PubMed Central

Fatty acid regulation of hepatic gene transcription was first reported in the early 1990s. Several transcription factors have been identified as targets of fatty acid regulation. This regulation is achieved by direct fatty acid binding to the transcription factor or by indirect mechanisms where fatty acids regulate signaling pathways controlling the expression of transcription factors or the phosphorylation, ubiquitination, or proteolytic cleavage of the transcription factor. Although dietary fatty acids are well-established regulators of hepatic transcription factors, emerging evidence indicates that endogenously generated fatty acids are equally important in controlling transcription factors in the context of glucose and lipid homeostasis. Our first goal in this review is to provide an up-to-date examination of the molecular and metabolic bases of fatty acid regulation of key transcription factors controlling hepatic metabolism. Our second goal is to link these mechanisms to nonalcoholic fatty liver disease (NAFLD), a growing health concern in the obese population. PMID:23528177

Jump, Donald B.; Tripathy, Sasmita; Depner, Christopher M.

2014-01-01

289

Omega3 Fatty Acid Composition of Persian Gulf Fishes  

Microsoft Academic Search

The aim of this study was to investigate the content of omega-3 fatty acids in Persian Gulf fishes. The fishes were collected from Persian Gulf and the content of fatty acids in the head, muscle, and liver of fishes were determined. Quantitative analysis of fatty acids was performed by gas chromatography (GC) and methylmyristate was used as the reference material.

M. J. Zibaee-Nezhad; M. Khosravi; S. Akbari; N. Bani-Asadi; Elnaz Golboostan

2010-01-01

290

Original article Effect of dietary polyunsaturated fatty acids  

E-print Network

Original article Effect of dietary polyunsaturated fatty acids on contractile function of hearts polyunsaturated fatty acids (PUFA, 18:2 n-6, 20:4 n-6, 22:4 n-6 and 22:5 n-6) in cardiac phospholipids. The n-6%) in n-3 PUFA-rich hearts. Physical train- ing did not markedly alter the polyunsaturated fatty acid

Boyer, Edmond

291

MYOCARDIAL CONCENTRATIONS OF FATTY ACIDS IN DOGS WITH DILATED CARDIOMYOPATHY  

Technology Transfer Automated Retrieval System (TEKTRAN)

To compare the myocardial concentrations of fatty acids in dogs with dilated cardiomyopathy (DCM) with control dogs using myocardium from 7 dogs with DCM, 16 control dogs. Myocardial tissues were homogenized and total fatty acids extracted and converted to methyl esters. Myocardial fatty acids conce...

292

75 FR 14082 - Ammonium Salts of Fatty Acids (C8  

Federal Register 2010, 2011, 2012, 2013, 2014

...EPA-HQ-OPP-2008-0652; FRL-8809-6] Ammonium Salts of Fatty Acids (C 8 -C 18 Saturated...of a tolerance for residues of ammonium salts of fatty acids (C 8 -C 18 saturated...permissible level for residues of ammonium salts of fatty acids (C 8 -C...

2010-03-24

293

21 CFR 172.863 - Salts of fatty acids.  

Code of Federal Regulations, 2012 CFR

...3 2012-04-01 2012-04-01 false Salts of fatty acids. 172.863 Section 172...CONSUMPTION Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely used in food...

2012-04-01

294

21 CFR 172.863 - Salts of fatty acids.  

Code of Federal Regulations, 2013 CFR

...3 2013-04-01 2013-04-01 false Salts of fatty acids. 172.863 Section 172...CONSUMPTION Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely used in food...

2013-04-01

295

21 CFR 172.863 - Salts of fatty acids.  

Code of Federal Regulations, 2014 CFR

...3 2014-04-01 2014-04-01 false Salts of fatty acids. 172.863 Section 172...CONSUMPTION Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely used in food...

2014-04-01

296

Synthesis of Commodity Chemicals from Renewable Fatty Acids  

E-print Network

RESEARCH HIGHLIGHTS Synthesis of Commodity Chemicals from Renewable Fatty Acids From the Resnick Chemicals from Renewable Fatty Acids Global Significance Alpha olefins represent an important class feedstocks. Fatty acids are an ideal candidate because of their abundance, low cost, and inherent

297

Atypical fatty acids appearing during technological treatments. General sur-  

E-print Network

Atypical fatty acids appearing during technological treatments. General sur- vey concerning rue Sully, BV 1540, 21034 Dijon) Fatty acids may be submitted to some changes during technological treatments. A correlation of the fragility of these fatty acids with the number of ethylenic bonds

Paris-Sud XI, Université de

298

Isomeric fatty acids and tumorigenesis: A commentary on recent work  

Microsoft Academic Search

This article critically reviews the existing, although limited, literature concerning trans fatty acids and tumorigenesis. Neither epidemiological nor experimental studies published to date have demonstrated any valid association between trans fatty acid ingestion and tumorigenesis. A recent study showed that under controlled conditions, a fat with a high content of ‘trans fatty acids did not promote the development of mammary

J. Edward Hunter; Clement Ip; Edward J. Hollenbach

1985-01-01

299

Fatty acid composition of meat from ruminants, with special emphasis on trans fatty acids  

Microsoft Academic Search

The fatty acid composition was determined in 39 samples of beef, 20 samples of veal, and 34 samples of lamb, representative\\u000a of the supply of ruminant meat in Denmark. Five cuts of beef and veal and three cuts of lamb with increasing fat content were\\u000a selected, and analysis of the fatty acid methyl esters was performed by gas-liquid chromatography (GLC)

Torben Leth; Lars Ovesen; Kirsten Hansen

1998-01-01

300

Lipid synthesis in lactation: diet and the fatty acid switch.  

PubMed

The lipid component of milk provides the critical nutritional source for generating both energy and essential nutrients to the growth of the newborn. Three types of substrate are utilized to synthesize milk triacylglycerides (TAG): dietary fat, fatty acids mobilized from adipose tissue stores, and lipids synthesized de novo synthesis from glucose and other dietary precursors, a process often referred to as de novo lipogenesis. The utilization of these various sources for TAG synthesis by the mammary epithelial cells is influenced by both the stage of lactation and the diet. From studies of gene expression in FVB mice, we observed that genes for beta-oxidation of fatty acids are downregulated along with the expression of Acyl-CoA thioesterase 1 (ACOT1). As a control mechanism we propose that during pregnancy ACOT1 provides a supply of cytoplasmic free fatty acids which increase the activation of PPARgamma. Ligand-induced activation of the PPAR/RXR transcription factor complex by free fatty acids, upregulates expression of genes required for beta-oxidation of fatty acids. The fall in ACOTs at secretory activation may facilitate the switch to lipogenesis perhaps mediated by activation of the LXR/RXR transcription factor complex. The response to changes in the supply of dietary lipids, on the other hand, is likely to be mediated by SREBP1, possibly acting through modulation of Spot 14. Stability of SREBP1 may be enhanced by a significant increase in Akt at secretory activation. These regulatory pathways may be critical to the production of milk with a balanced TAG composition to support neonatal development of the newborn. PMID:18027074

Rudolph, Michael C; Neville, Margaret C; Anderson, Steven M

2007-12-01

301

Fatty acid selectivity of lipases: Erucic acid from rapeseed oil  

Microsoft Academic Search

The fatty acid selectivity of several commercial lipases was evaluated in the hydrolysis of high-erucic acid rapeseed oil\\u000a (HEARO). The lipase ofPseudomonas cepacia catalyzed virtually complete hydrolysis of the oil (94–97%), while that ofGeotrichum candidum discriminated strongly against erucic acid, especially in esterification. A two-step process is suggested for obtaining a\\u000a highly enriched erucic acid in which theG. candidum lipase

Philip E. Sonnet; Thomas A. Foglia; Stephen H. Feairheller

1993-01-01

302

Fatty Acid Composition and Volatile Constituents of Protaetia brevitarsis Larvae  

PubMed Central

A total of 48 different volatile oils were identified form P. brevitarsis larvae by gas chromatography/mass spectrometry (GC/MS). Acids (48.67%) were detected as the major group in P. brevitarsis larvae comprising the largest proportion of the volatile compounds, followed by esters (19.84%), hydrocarbons (18.90%), alcohols (8.37%), miscellaneous (1.71%), aldehydes (1.35%) and terpenes (1.16%). The major volatile constituents were 9-hexadecenoic acid (16.75%), 6-octadecenoic acid (14.88%) and n-hexadecanoic acid (11.06%). The composition of fatty acid was also determined by GC analysis and 16 fatty acids were identified. The predominant fatty acids were oleic acid (C18:1, 64.24%) followed by palmitic acid (C16:0, 15.89%), palmitoleic acid (C16:1, 10.43%) and linoleic acid (C18:2, 4.69%) constituting more than 95% of total fatty acids. The distinguished characteristic of the fatty acid profile of P. brevitarsis larvae was the high proportion of unsaturated fatty acid (80.54% of total fatty acids) versus saturated fatty acids (19.46% of total fatty acids). Furthermore, small but significant amounts of linoleic, linolenic and ?-linolenic acids bestow P. brevitarsis larvae with considerable nutritional value. The novel findings of the present study provide a scientific basis for the comprehensive utilization of the insect as a nutritionally promising food source and a possibility for more effective utilization. PMID:24471125

Yeo, Hyelim; Youn, Kumju; Kim, Minji; Yun, Eun-Young; Hwang, Jae-Sam; Jeong, Woo-Sik; Jun, Mira

2013-01-01

303

Sugar fatty acid esters inhibit biofilm formation by food-borne pathogenic bacteria  

PubMed Central

Effects of food additives on biofilm formation by food-borne pathogenic bacteria were investigated. Thirty-three potential food additives and 3 related compounds were added to the culture medium at concentrations from 0.001 to 0.1% (w/w), followed by inoculation and cultivation of five biofilm-forming bacterial strains for the evaluation of biofilm formation. Among the tested food additives, 21 showed inhibitory effects of biofilm formation by Staphylococcus aureus and Escherichia coli, and in particular, sugar fatty acid esters showed significant anti-biofilm activity. Sugar fatty acid esters with long chain fatty acid residues (C14-16) exerted their inhibitory effect at the concentration of 0.001%(w/w), but bacterial growth was not affected at this low concentration. Activities of the sugar fatty acid esters positively correlated with the increase of the chain length of the fatty acid residues. Sugar fatty acid esters inhibited the initial attachment of the Staphylococcus aureus cells to the abiotic surface. Sugar fatty acid esters with long chain fatty acid residues (C14-16) also inhibited biofilm formation by Streptococcus mutans and Listeria monocytogenes at 0.01%(w/w), while the inhibition of biofilm formation by Pseudomonas aeruginosa required the addition of a far higher concentration (0.1%(w/w)) of the sugar fatty acid esters. PMID:20089325

Furukawa, Soichi; Akiyoshi, Yuko; O’Toole, George A.; Ogihara, Hirokazu; Morinaga, Yasushi

2010-01-01

304

40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.  

Code of Federal Regulations, 2014 CFR

...2014-07-01 2014-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection...Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid...

2014-07-01

305

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

Code of Federal Regulations, 2014 CFR

... 31 2014-07-01 2014-07-01 false Fatty acid maleic acid amides (generic). 721.10512 Section 721.10512...for Specific Chemical Substances § 721.10512 Fatty acid maleic acid amides (generic). (a) Chemical...

2014-07-01

306

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

Code of Federal Regulations, 2013 CFR

... 32 2013-07-01 2013-07-01 false Fatty acid maleic acid amides (generic). 721.10512 Section 721.10512...for Specific Chemical Substances § 721.10512 Fatty acid maleic acid amides (generic). (a) Chemical...

2013-07-01

307

n-3 fatty acids, ?-linolenic acid, and antioxidants in sepsis  

PubMed Central

The usefulness of n-3 fatty acids, ?-linolenic acid and antioxidants in the critically ill is controversial. I propose that adverse outcome in the critically ill is due to excess production of proinflammatory cytokines and eicosanoids from polyunsaturated fatty acids (PUFAs), while generation of anti-inflammatory products of PUFAs may lead to a favorable outcome. Hence, I suggest that measurement of plasma levels of various cytokines, free radicals, and proinflammatory and anti-inflammatory products of PUFAs and correlating them to the clinical picture may pave the way to identify prognostic markers and develop newer therapeutic strategies to prevent and manage critical illness. PMID:23597172

2013-01-01

308

Fatty acid-amino acid conjugates diversification in Lepidopteran caterpillars  

Technology Transfer Automated Retrieval System (TEKTRAN)

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...

309

Intermediates in fatty acid oxidation  

PubMed Central

1. Aqueous extracts of acetone-dried liver and kidney mitochondria, supplemented with NAD+, CoA and phenazine methosulphate, efficiently convert fatty-acyl-CoA compounds into acetyl-CoA; the process was followed with an O2 electrode. 2. Label from [1-14C]octanoyl-CoA appears in acetyl-CoA more rapidly than that from [8-14C]octanoyl-CoA. 3. Oxidation of [8-14C]octanoyl-CoA was terminated by addition of neutral ethanolic hydroxylamine and the resulting hydroxamates were separated chromatographically. Hydroxamate derivatives of 3-hydroxyoctanoyl-, hexanoyl-, butyryl- and acetyl-CoA were obtained. 4. These and other observations suggest that oxidation of octanoyl-CoA by extracts involves participation of free intermediates rather than uninterrupted complete degradation of individual molecules to acetyl-CoA by a multienzyme complex. 5. Intact liver mitochondria studied by the hydroxamate technique were also shown to form intermediates during oxidation of labelled octanoates. In addition to octanoylhydroxamate, [8-14C]octanoate gave rise to small amounts of hexanoyl-, butyryl- and 3-hydroxyoctanoyl-hydroxamate. In contrast with extracts, however, where the quantity of intermediates found was a significant fraction of the precursors, mitochondria oxidizing octanoate contained much larger quantities of octanoyl-CoA than of any other intermediate. PMID:4722901

Stewart, H. B.; Tubbs, P. K.; Stanley, K. K.

1973-01-01

310

Identification of fatty acids in canine seminal plasma.  

PubMed

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. PMID:23398451

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

2014-03-01

311

Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition  

PubMed Central

In the representative gut bacterium Lactobacillus plantarum, we identified genes encoding the enzymes involved in a saturation metabolism of polyunsaturated fatty acids and revealed in detail the metabolic pathway that generates hydroxy fatty acids, oxo fatty acids, conjugated fatty acids, and partially saturated trans-fatty acids as intermediates. Furthermore, we observed these intermediates, especially hydroxy fatty acids, in host organs. Levels of hydroxy fatty acids were much higher in specific pathogen-free mice than in germ-free mice, indicating that these fatty acids are generated through polyunsaturated fatty acids metabolism of gastrointestinal microorganisms. These findings suggested that lipid metabolism by gastrointestinal microbes affects the health of the host by modifying fatty acid composition. PMID:24127592

Kishino, Shigenobu; Takeuchi, Michiki; Park, Si-Bum; Hirata, Akiko; Kitamura, Nahoko; Kunisawa, Jun; Kiyono, Hiroshi; Iwamoto, Ryo; Isobe, Yosuke; Arita, Makoto; Arai, Hiroyuki; Ueda, Kazumitsu; Shima, Jun; Takahashi, Satomi; Yokozeki, Kenzo; Shimizu, Sakayu; Ogawa, Jun

2013-01-01

312

Omega3 enriched egg production: the effect of ?-linolenic ?-3 fatty acid sources on laying hen performance and yolk lipid content and fatty acid composition  

Microsoft Academic Search

1. Diets high in total lipids, saturated fatty acids, trans fatty acids, and having high ?-6:?-3 fatty acid ratios, have been shown to be related to increased instances of coronary heart disease, while diets high in ?-3 fatty acids have been shown to decrease the risk.2. Feeding ?-3 fatty acid diets to laying hens has been shown to improve the

A. Antruejo; J. O. Azcona; P. T. Garcia; C. Gallinger; M. Rosmini; R. Ayerza; W. Coates; C. D. Perez

2011-01-01

313

Fatty acid synthase and liver triglyceride metabolism: housekeeper or messenger?  

PubMed Central

Fatty acid synthase (FAS) catalyzes the de novo synthesis of fatty acids. In the liver, FAS has long been categorized as a housekeeping protein, producing fat for storage of energy when nutrients are present in excess. Most previous studies of FAS regulation have focused on the control of gene expression. However, recent findings suggest that hepatic FAS may also be involved in signaling processes that include activation of peroxisome proliferator-activated receptor ? (PPAR?). Moreover, reports of rapid alterations in FAS activity and as well as findings of post-translational modifications of the FAS protein support the notion that dynamic events in addition to transcription impact FAS regulation. These results indicate that FAS enzyme activity can impact liver physiology through signaling as well as energy storage and that its regulation may be complex. PMID:22009142

Jensen-Urstad, Anne P. L.; Semenkovich, Clay F.

2011-01-01

314

Fatty acid synthase and liver triglyceride metabolism: housekeeper or messenger?  

PubMed

Fatty acid synthase (FAS) catalyzes the de novo synthesis of fatty acids. In the liver, FAS has long been categorized as a housekeeping protein, producing fat for storage of energy when nutrients are present in excess. Most previous studies of FAS regulation have focused on the control of gene expression. However, recent findings suggest that hepatic FAS may also be involved in signaling processes that include activation of peroxisome proliferator-activated receptor ? (PPAR?). Moreover, reports of rapid alterations in FAS activity as well as findings of post-translational modifications of the FAS protein support the notion that dynamic events in addition to transcription impact FAS regulation. These results indicate that FAS enzyme activity can impact liver physiology through signaling as well as energy storage and that its regulation may be complex. This article is part of a Special Issue entitled Triglyceride Metabolism and Disease. PMID:22009142

Jensen-Urstad, Anne P L; Semenkovich, Clay F

2012-05-01

315

Motility of rabbit alveolar cells: role of unsaturated fatty acids.  

PubMed Central

A mechanism for the specific accumulation of macrophages in alveoli or other biologic cavities following injury is presented. The data herein indicate that unsaturated fatty acids, ie, linoleic and linolenic acids, which accumulate in rat pleura following injection of carrageenan or during incubation of rabbit alveolar macrophages (AMs), strongly activate migration in vitro of AMs but not of human polymorphonuclear leukocytes (PMNLs). Other anionic lipids, ie, phosphatidylglycerol, as well as various nonspecific proteins, such as gelatin, or albumin were also shown to be potent activators of migration of AMs and not of PMNLs. These observations suggest that the elaboration of unsaturated fatty acids, as well as of nonspecific proteins, is responsible for the specific accumulation of macrophages in injured body spaces, such as alveoli or pleura. PMID:474715

Lynn, W. S.; Mukherjee, C.

1979-01-01

316

The capacity for long-chain polyunsaturated fatty acid synthesis in a carnivorous vertebrate: Functional characterisation and nutritional regulation of a Fads2 fatty acyl desaturase with ?4 activity and an Elovl5 elongase in striped snakehead (Channa striata).  

PubMed

The endogenous production of long-chain polyunsaturated fatty acids (LC-PUFA) in carnivorous teleost species inhabiting freshwater environments is poorly understood. Although a predatory lifestyle could potentially supply sufficient LC-PUFA to satisfy the requirements of these species, the nutrient-poor characteristics of the freshwater food web could impede this advantage. In this study, we report the cloning and functional characterisation of an elongase enzyme in the LC-PUFA biosynthesis pathway from striped snakehead (Channa striata), which is a strict freshwater piscivore that shows high deposition of LC-PUFA in its flesh. We also functionally characterised a previously isolated fatty acyl desaturase cDNA from this species. Results showed that the striped snakehead desaturase is capable of ?4 and ?5 desaturation activities, while the elongase showed the characteristics of Elovl5 elongases. Collectively, these findings reveal that striped snakehead exhibits the genetic resources to synthesise docosahexaenoic acid (DHA; 22:6n-3) from eicosapentaenoic acid (EPA; 20:5n-3). Both genes are expressed at considerable levels in the brain and the liver. In liver, both genes were up-regulated by dietary C18 PUFA, although this increase did not correspond to a significant rise in the deposition of muscle LC-PUFA. Brain tissue of fish fed with plant oil diets showed higher expression of fads2 gene compared to fish fed with fish oil-based diet, which could ensure DHA levels remain constant under limited dietary DHA intake. This suggests the importance of DHA production from EPA via the ?4 desaturation step in order to maintain an optimal reserve of DHA in the neuronal tissues of carnivores. PMID:25542509

Kuah, Meng-Kiat; Jaya-Ram, Annette; Shu-Chien, Alexander Chong

2015-03-01

317

Time to Talk: 7 Things to Know about Omega-3 Fatty Acids  

MedlinePLUS

... to Talk Tips 7 Things To Know About Omega-3 Fatty Acids Omega-3 fatty acids are a group of polyunsaturated fatty ... a number of functions in the body. The omega-3 fatty acids EPA and DHA are found in ...

318

Response of Aedes triseriatus larvae to fatty acids of Cladophora  

Microsoft Academic Search

The activity of a methanol extract residue fromCladophora glomerata against larvae ofAedes triseriatus is confirmed. Fractionation of this residue by solubility in solvents of varying polarity is monitored by bioassay withA. triseriatus larvae. The presence of fatty acids in the active hexane soluble fraction and saponified material obtained therefrom is indicated by1H NMR and IR. The identification of the individual

R. T. LaLonde; C. D. Morris; C. F. Wong; L. C. Gardner; D. J. Eckert; D. R. King; R. H. Zimmerman

1979-01-01

319

A low fat diet enhances polyunsaturated fatty acid desaturation and elongation independent of n3 enrichment  

Technology Transfer Automated Retrieval System (TEKTRAN)

Low fat diets are associated with risk reduction for chronic metabolic diseases compared to high fat diets. To evaluate effects of varied fat and fatty acid intake on lipid metabolism, phospholipid fatty acids (PLFA) were measured and delta 5 and 6 desaturase activities (D5D, D6D) were calculated in...

320

Essential Fatty Acids and Attention-Deficit-Hyperactivity Disorder: A Systematic Review  

ERIC Educational Resources Information Center

Aim: Essential fatty acids (EFAs), also known as omega-3 and omega-6 fatty acids, have been claimed to have beneficial effects as a treatment for attention-deficit-hyperactivity disorder (ADHD). Animal experiments have provided information about the role of EFA in the brain, and several mechanisms of EFA activity are well known. The current review…

Raz, Raanan; Gabis, Lidia

2009-01-01

321

Neuropsychological Outcomes in Fatty Acid Oxidation Disorders: 85 Cases Detected by Newborn Screening  

ERIC Educational Resources Information Center

Mitochondrial fatty acid oxidation disorders include conditions in which the transport of activated acyl-Coenzyme A (CoA) into the mitochondria or utilization of these substrates is disrupted or blocked. This results in a deficit in the conversion of fat into energy. Most patients with fatty acid oxidation defects are now identified through…

Waisbren, Susan E.; Landau, Yuval; Wilson, Jenna; Vockley, Jerry

2013-01-01

322

What do we really know about the health effects of natural sources of trans fatty acids?  

Technology Transfer Automated Retrieval System (TEKTRAN)

While the food industry remains actively engaged in the development of alternatives for partially hydrogenated vegetable oils in order to reduce intake of trans fatty acids, intake of these fatty acids from natural sources remains as a small part of our diet. The question remains, are there differ...

323

Production of hydroxylated fatty acids in genetically modified plants  

DOEpatents

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.

Somerville, Chris (Portola Valley, CA); Broun, Pierre (Burlingame, CA); van de Loo, Frank (Lexington, KY)

2001-01-01

324

Mitochondrial Fatty Acid Oxidation in Obesity  

PubMed Central

Abstract Significance: Current lifestyles with high-energy diets and little exercise are triggering an alarming growth in obesity. Excess of adiposity is leading to severe increases in associated pathologies, such as insulin resistance, type 2 diabetes, atherosclerosis, cancer, arthritis, asthma, and hypertension. This, together with the lack of efficient obesity drugs, is the driving force behind much research. Recent Advances: Traditional anti-obesity strategies focused on reducing food intake and increasing physical activity. However, recent results suggest that enhancing cellular energy expenditure may be an attractive alternative therapy. Critical Issues: This review evaluates recent discoveries regarding mitochondrial fatty acid oxidation (FAO) and its potential as a therapy for obesity. We focus on the still controversial beneficial effects of increased FAO in liver and muscle, recent studies on how to potentiate adipose tissue energy expenditure, and the different hypotheses involving FAO and the reactive oxygen species production in the hypothalamic control of food intake. Future Directions: The present review aims to provide an overview of novel anti-obesity strategies that target mitochondrial FAO and that will definitively be of high interest in the future research to fight against obesity-related disorders. Antioxid. Redox Signal. 19, 269–284. PMID:22900819

Serra, Dolors; Mera, Paula; Malandrino, Maria Ida; Mir, Joan Francesc

2013-01-01

325

Human Serum Albumin and p53-Activating Peptide Fusion Protein Is Able to Promote Apoptosis and Deliver Fatty Acid-Modified Molecules  

PubMed Central

Therapeutic peptides offer a high degree of specificity, potency, and low toxicity; making them promising candidates for cancer therapy. Despite these advantages, a number of hurdles, such as poor serum stability and inefficient cellular penetration, must be overcome. Fusing a therapeutic peptide to human serum albumin (HSA) is a common approach to extend the serum stability of a peptide that binds to extracellular receptors. However, no study has shown that this approach can be applied to target intracellular proteins. Here we demonstrate the feasibility of using a recombinant human serum albumin (rHSA) fusion protein to simultaneously deliver two types of molecules: a peptide capable of binding an intracellular target, as well as fatty acid (FA)-modified FITC (FA-FITC). Two peptides reported to disrupt the intracellular p53 and MDM2/MDMX interaction were fused to the C-terminal of HSA. Cellular and biochemical studies indicate that rHSA fusion proteins were efficiently taken up by SJSA-1 cells and retained MDM2- and MDMX-binding activity. By inducing the accumulation of p53, both fusion proteins promoted efficient cytotoxicity in SJSA-1 cells via caspase activation. Long chain fatty acid (LCFA) transportation is an essential endogenous function of HSA. This study also demonstrates that rHSA fusion proteins formed highly stable complexes with FA-FITC via non-covalent interactions. FA-FITC complexed with HSA could be internalized efficiently and rHSA-P53i and rHSA-PMI retained apoptotic activity as complex components. It is expected that such an approach can ultimately be used to facilitate intracellular delivery of two anticancer therapeutics, each with distinct but complimentary mechanisms, to achieve synergistic efficacy. PMID:24278348

Joshi, Michelle R.; Yao, Nianhuan; Myers, Kenneth A.; Li, Zhiyu

2013-01-01

326

Rapid colorimetric determination of free fatty acids  

Microsoft Academic Search

In 1964, a method was described for the determination of free fatty acids (FFAs) in vegetable oil. This paper describes an\\u000a expansion of that work, improving the sensitivity and reproducibility of the method, as well as examination of solubilities\\u000a of the copper soaps as a function of chain length and unsaturation. Involvement of the micellar structure was reviewed. Finally,\\u000a a

Robert R. Lowry; Ian J. Tinsley

1976-01-01

327

Fatty acid effects on fibroblast cholesterol synthesis  

SciTech Connect

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).

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

1987-05-01

328

Metabolism of Fatty Acids in Adipocytes  

Microsoft Academic Search

\\u000a Adipose tissue is found in mammals in two different forms: white adipose tissue (WAT) and brown adipose tissue (BAT). The\\u000a primary and best-known function of WAT is to store energy in the form of triglycerides in periods of excess energy intake\\u000a and to release it in the form of free fatty acids for other organs during fasting, whereas BAT is

A. L. Dinel; C. Kolditz; D. Langin

329

Viscosities of vegetable oils and fatty acids  

Microsoft Academic Search

Data for viscosity as a function of temperature from 24 to 110C (75 to 230F) have been measured for a number of vegetable\\u000a oils (crambe, rapeseed, corn, soybean, milk-weed, coconut, lesquerella) and eight fatty acids in the range from C9 to C22. The viscosity measurements were performed according to ASTM test methods D 445 and D 446. Several correlations were

H. Noureddini; B. C. Teoh; L. Davis Clements

1992-01-01

330

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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...

331

Analysis of fatty acids in ecstasy tablets.  

PubMed

Fatty acids are the basis of so-called stearates which are frequently used as lubricants in the production of ecstasy tablets. Being a product added at the initial tablet production step its composition does not change once the compression is performed. The analysis of fatty acids can therefore provide useful information for a drug intelligence purpose. In this context an appropriate analytical method was developed to improve results already obtained by routine analyses. Considering the small quantity of such fatty acids in ecstasy tablets (approximately 3%) the research focussed on their extraction and concentration. Two different procedures were tested: (1) liquid/liquid extraction using dichloromethane followed by derivatisation and (2) in situ transesterification using bortrifluoride. Analyses were performed by GC-MS. The two procedures were optimized and applied to eight ecstasy seizures, in order to choose one of the procedures for its application to a large ecstasy sample set. They were compared by considering the number of peaks detected and sample amount needed, reproducibility and other technical aspects. PMID:19395206

Baer, Ines; Margot, Pierre

2009-07-01

332

Lipidomics of oxidized polyunsaturated fatty acids  

PubMed Central

Lipid mediators are produced from the oxidation of polyunsaturated fatty acids through enzymatic and free radical-mediated reactions. When subject to oxygenation via cyclooxygenases, lipoxygenases, and cytochrome P450 monooxygenases, polyunsaturated fatty acids give rise to an array of metabolites including eicosanoids, docosanoids, and octadecanoids. These potent bioactive lipids are involved in many biochemical and signaling pathways, with inflammation being of particular importance. Moreover, because they are produced by more than one pathway and substrate, and are present in a variety of biological milieus, their analysis is not always possible with conventional assays. Liquid chromatography coupled to electrospray mass spectrometry offers a versatile and sensitive approach for the analysis of bioactive lipids, allowing specific and accurate quantitation of multiple species present in the same sample. Here we explain the principles of this approach to mediator lipidomics and present detailed protocols for the assay of enzymatically produced oxygenated metabolites of polyunsaturated fatty acids that can be tailored to answer biological questions or facilitate assessment of nutritional and pharmacological interventions. PMID:22940496

Massey, Karen A.; Nicolaou, Anna

2013-01-01

333

Evaluation of antifungal activity of free fatty acids methyl esters fraction isolated from Algerian Linum usitatissimum L. seeds against toxigenic Aspergillus  

PubMed Central

Objective The aim of this study was to evaluate the antifungal activity of the major fraction of fatty acids methyl esters (FAMEs) isolated from Linum usitatissimum L. seeds oil collected from Bechar department (Algeria). Methods The assessment of antifungal activity was carried out in terms of percentage of radial growth on solid medium (potatoes dextrose agar PDA) and biomass growth inhibition on liquid medium (potatoes dextrose broth PDB) against two fungi. Results The FAMEs was found to be effective in inhibiting the radial mycelial growth of Aspergillus flavus more than Aspergillus ochraceus on all tested concentrations. The highest antifungal index was found to be (54.19%) compared to Aspergillus ochraceus (40.48%). The results of the antifungal activity of the FAMEs inhibition of biomass on liquid medium gave no discounted results, but this does not exclude the antifungal activity. Conclusions We can assume that the observed antifungal potency may be due to the abundance of linoleic and ?-linolenic acids in linseed oil which appears to be promising to treat fungal infections, storage fungi and food spoilage in food industry field. PMID:23730556

Abdelillah, Amrouche; Houcine, Benmehdi; Halima, Dalile; Meriem, Chabane sari; Imane, Zaaboub; Eddine, Smahi Djamal; Abdallah, Moussaoui; Daoudi, Chabane sari

2013-01-01

334

Fatty acids and carotenoids from Stinging Nettle ( Urtica dioica L.)  

Microsoft Academic Search

Several parts (leaves at different maturity stages, stems, roots and seeds) of an edible wild vegetable, Stinging Nettle (Urtica dioica L.) were analysed for fatty acids by GLC and carotenoids by reversed-phase HPLC and gradient elution. ?-linolenic acid was the pre-dominant fatty acid in leaves, while seeds were richer in linoleic acid. Nine carotenoids were identified in the leaves. For

J. L. Guil-Guerrero; M. M. Rebolloso-Fuentes; M. E. Torija Isasa

2003-01-01

335

Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer  

E-print Network

Review Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer450 epoxygenase Soluble epoxide hydrolase Epoxyeicosatrienoic acids Epoxydocosapentaenoic acids a b s t r a c t Epoxygenated fatty acids (EpFAs), which are lipid mediators produced by cytochrome P450

Hammock, Bruce D.

336

Temperature Affects Fatty Acids In Methylococcus Capsulatus  

NASA Technical Reports Server (NTRS)

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.

Jahnke, Linda L.

1993-01-01

337

Absence of albumin in the plasma of the common carp Cyprinus carpio: binding of fatty acids to high density lipoprotein  

Microsoft Academic Search

It was investigated whether an albumin-like protein, active in the transport of free fatty acids, is present in the blood of the common carp, Cyprinus carpio. In contrast with the brown trout Salmo trutta, no free fatty acid-binding protein could be found with a molecular mass and isoelectric point similar to human serum albumin. On the other hand, free fatty

H. De Smet; R. Blust; L. Moens

1998-01-01

338

Fatty Acids in the Causation and Therapy of Metabolic Syndrome  

Microsoft Academic Search

The role of fatty acids in the prevention and pathogenesis of metabolic syndrome leading to cardiovascular diseases, type\\u000a 2 diabetes and insulin resistance are reviewed. We did Medline, PubMed search till March, 2007. Excess of linoleic acid, trans\\u000a fatty acids (TFA), saturated and total fat as well as refined starches and sugar are proinflammatory. Low dietary monounsaturated\\u000a fatty acids (MUFA)

Ram B. Singh; Fabien De Meester; Viola Mechirova; Daniel Pella; Kuniaki Otsuka

339

Alkyd resins modified with cyclic fatty acids a preliminary evaluation  

Microsoft Academic Search

Alkyd resins were modified to 50% oil length with crude, flash-distilled, and 78% pure cyclic fatty acids. These resins were\\u000a compared with ones modified with naturally occurring fatty acids and with vegetable oils. Those modified with the cyclic acids\\u000a process more rapidly than those prepared with linseed, safflower, or soybean fatty acids, and they also have good nonyellowing\\u000a properties. Resins

W. R. Miller; H. M. Teeter; A. W. Schwab; J. C. Cowan

1962-01-01

340

Omega3 fatty acids from fish oils and cardiovascular disease  

Microsoft Academic Search

Fish and fish oils contain the omega-3 fatty acids known as eicosapentaenoic acid (EPA) plus docosahexaenoic acid (DHA). Epidemiological studies have shown an inverse relation between the dietary consumption of fish containing EPA\\/DHA and mortality from coronary heart disease. These relationships have been substantiated from blood measures of omega-3 fatty acids including DHA as a physiological biomarker for omega-3 fatty

Darren J. Holub; Bruce J. Holub

2004-01-01

341

Role of serotonin in fatty acid-induced non-alcoholic fatty liver disease in mice  

PubMed Central

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 development of fatty liver disease in mice, likely by a dysfunction of the small intestinal mucosal barrier. PMID:24321090

2013-01-01

342

Enzymatic purification of polyunsaturated fatty acids.  

PubMed

Polyunsaturated fatty acids (PUFAs) have various physiological functions. Of these, ethyl eicosapentaenoate is industrially purified and used as a medicine. Other PUFAs, such as docosahexaenoic acid (DHA), gamma-linolenic acid (GLA), and arachidonic acid (AA), are also expected to be used as pharmaceutical agents; however, their industrial purification processes have not been established. Because PUFAs are highly unstable against heat and oxidation, we attempted to purify them by taking advantage of their enzymatic reactions. When free fatty acids (FFAs) originating from PUFA-containing oil were selectively esterified with lauryl alcohol (LauOH) using a lipase acting on a desired PUFA very weakly, the PUFA was efficiently enriched in the FFA fraction. In addition, when selective alcoholysis of ethyl esters originating from PUFA-containing oil with LauOH was carried out, the PUFA ethyl ester (EtPUFA) was enriched to a desired purity in the unreacted ethyl ester fraction. These reaction mixtures contain LauOH, PUFA (EtPUFA), and lauryl esters, and their molecular weights are different from one another. Hence, PUFA or EtPUFA can be easily separated by conventional distillation. Selective esterification increased the purity of DHA, GLA, and n-6 PUFAs rich in AA to 91, 98, and 96 wt%, respectively. Selective alcoholysis was also effective for increasing the purity of ethyl docosahexaenoate to 90 wt%. PMID:16233035

Shimada, Y; Sugihara, A; Tominaga, Y

2001-01-01

343

Four Trypanosoma brucei fatty acyl-CoA synthetases: fatty acid specificity of the recombinant proteins.  

PubMed Central

As part of our investigation of fatty acid metabolism in Trypanosoma brucei, we have expressed four acyl-CoA synthetase (TbACS) genes in Esherichia coli. The recombinant proteins, with His-tags on their C-termini, were purified to near homogeneity using nickel-chelate affinity chromatography. Although these enzymes are highly homologous, they have distinct specificities for fatty acid chain length. TbACS1 prefers saturated fatty acids in the range C(11:0) to C(14:0) and TbACS2 prefers shorter fatty acids, mainly C(10:0). TbACS3 and 4, which have 95% sequence identity, have similar specificities, favouring fatty acids between C(14:0) and C(17:0). In addition, TbACS1, 3 and 4 function well with a variety of unsaturated fatty acids. PMID:11535136

Jiang, D W; Englund, P T

2001-01-01

344

Analysis of fatty acid content and composition in microalgae.  

PubMed

A method to determine the content and composition of total fatty acids present in microalgae is described. Fatty acids are a major constituent of microalgal biomass. These fatty acids can be present in different acyl-lipid classes. Especially the fatty acids present in triacylglycerol (TAG) are of commercial interest, because they can be used for production of transportation fuels, bulk chemicals, nutraceuticals (?-3 fatty acids), and food commodities. To develop commercial applications, reliable analytical methods for quantification of fatty acid content and composition are needed. Microalgae are single cells surrounded by a rigid cell wall. A fatty acid analysis method should provide sufficient cell disruption to liberate all acyl lipids and the extraction procedure used should be able to extract all acyl lipid classes. With the method presented here all fatty acids present in microalgae can be accurately and reproducibly identified and quantified using small amounts of sample (5 mg) independent of their chain length, degree of unsaturation, or the lipid class they are part of. This method does not provide information about the relative abundance of different lipid classes, but can be extended to separate lipid classes from each other. The method is based on a sequence of mechanical cell disruption, solvent based lipid extraction, transesterification of fatty acids to fatty acid methyl esters (FAMEs), and quantification and identification of FAMEs using gas chromatography (GC-FID). A TAG internal standard (tripentadecanoin) is added prior to the analytical procedure to correct for losses during extraction and incomplete transesterification. PMID:24121679

Breuer, Guido; Evers, Wendy A C; de Vree, Jeroen H; Kleinegris, Dorinde M M; Martens, Dirk E; Wijffels, René H; Lamers, Packo P

2013-01-01

345

Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants  

Microsoft Academic Search

We report the production of two very long chain polyunsaturated fatty acids, arachidonic acid (AA) and eicosapentaenoic acid (EPA), in substantial quantities in a higher plant. This was achieved using genes encoding enzymes participating in the ?3\\/6 ?8-desaturation biosynthetic pathways for the formation of C20 polyunsaturated fatty acids. Arabidopsis thaliana was transformed sequentially with genes encoding a ?9-specific elongating activity

Tom Fraser; Sam Mugford; Gary Dobson; Olga Sayanova; Justine Butler; Johnathan A Napier; A Keith Stobart; Colin M Lazarus; Baoxiu Qi

2004-01-01

346

Surface-active properties of lipophilic antioxidants tyrosol and hydroxytyrosol fatty acid esters: a potential explanation for the nonlinear hypothesis of the antioxidant activity in oil-in-water emulsions.  

PubMed

Our group has recently observed a nonlinear tendency in antioxidant capacity of different hydroxytyrosol fatty acid esters in fish oil-in-water emulsions, where a maximum of antioxidant efficiency appeared for hydroxytyrosol octanoate. These results appear to disagree with the antioxidant polar paradox. Because the physical location of the antioxidants in an oil-water interface has been postulated as an important factor in explaining this behavior, we have prepared a series of tyrosol and hydroxytyrosol fatty acid esters with different chain length and studied their surface-active properties in water, because these physicochemical parameters could be directly related to the preferential placement at the interface. We have found that tyrosol and hydroxytyrosol fatty acid esters are relevant surfactants when the right hydrophilic-lipophilic balance (HLB) is attained and, in some cases, as efficient as emulsifiers commonly used in industry, such as Brij 30 or Tween 20. Moreover, a nonlinear dependency of surfactant effectiveness is observed with the increase in chain length of the lipophilic antioxidants. This tendency seems to fit quite well with the reported antioxidant activity in emulsions, and the best antioxidant of the series (hydroxytyrosol octanoate) is also a very effective surfactant. This potential explanation of the nonlinear hypothesis will help in the rational design of antioxidants used in oil-in-water emulsions. PMID:20524658

Lucas, Ricardo; Comelles, Francisco; Alcántara, David; Maldonado, Olivia S; Curcuroze, Melanie; Parra, Jose L; Morales, Juan C

2010-07-14

347

Human cyclooxygenase-1 activity and its responses to COX inhibitors are allosterically regulated by nonsubstrate fatty acids  

PubMed Central

Recombinant human prostaglandin endoperoxide H synthase-1 (huPGHS-1) was characterized. huPGHS-1 has a single high-affinity heme binding site per dimer and exhibits maximal cyclooxygenase (COX) activity with one heme per dimer. Thus, huPGHS-1 functions as a conformational heterodimer having a catalytic monomer (Ecat) with a bound heme and an allosteric monomer (Eallo) lacking heme. The enzyme is modestly inhibited by common FAs including palmitic, stearic, and oleic acids that are not COX substrates. Studies of arachidonic acid (AA) substrate turnover at high enzyme-to-substrate ratios indicate that nonsubstrate FAs bind the COX site of Eallo to modulate the properties of Ecat. Nonsubstrate FAs slightly inhibit huPGHS-1 but stimulate huPGHS-2, thereby augmenting AA oxygenation by PGHS-2 relative to PGHS-1. Nonsubstrate FAs potentiate the inhibition of huPGHS-1 activity by time-dependent COX inhibitors, including aspirin, all of which bind Ecat. Surprisingly, preincubating huPGHS-1 with nonsubstrate FAs in combination with ibuprofen, which by itself is a time-independent inhibitor, causes a short-lived, time-dependent inhibition of huPGHS-1. Thus, in general, having a FA bound to Eallo stabilizes time-dependently inhibited conformations of Ecat. We speculate that having an FA bound to Eallo also stabilizes Ecat conformers during catalysis, enabling half of sites of COX activity. PMID:22547204

Zou, Hechang; Yuan, Chong; Dong, Liang; Sidhu, Ranjinder S.; Hong, Yu H.; Kuklev, Dmitry V.; Smith, William L.

2012-01-01

348

The Stimulatory Effect of Essential Fatty Acids on Glucose Uptake Involves Both Akt and AMPK Activation in C2C12 Skeletal Muscle Cells  

PubMed Central

Essential fatty acid (EFA) is known to be required for the body to function normally and healthily. However, the effect of EFA on glucose uptake in skeletal muscle has not yet been fully investigated. In this study, we examined the effect of two EFAs, linoleic acid (LA) and ?-linolenic acid (ALA), on glucose uptake of C2C12 skeletal muscle cells and investigated the mechanism underlying the stimulatory effect of polyunsaturated EFAs in comparison with monounsaturated oleic acid (OA). In palmitic acid (PA)-induced insulin resistant cells, the co-treatment of EFAs and OA with PA almost restored the PA-induced decrease in the basal and insulin-stimulated 2-NBDG (fluorescent D-glucose analogue) uptake, respectively. Two EFAs and OA significantly protected PA-induced suppression of insulin signaling, respectively, which was confirmed by the increased levels of Akt phosphorylation and serine/threonine kinases (PKC? and JNK) dephosphorylation in the western blot analysis. In PA-untreated, control cells, the treatment of 500 µM EFA significantly stimulated 2-NBDG uptake, whereas OA did not. Phosphorylation of AMP-activated protein kinase (AMPK) and one of its downstream molecules, acetyl-CoA carboxylase (ACC) was markedly induced by EFA, but not OA. In addition, EFA-stimulated 2-NBDG uptake was significantly inhibited by the pre-treatment of a specific AMPK inhibitor, adenine 9-?-D-arabinofuranoside (araA). These data suggest that the restoration of suppressed insulin signaling at PA-induced insulin resistant condition and AMPK activation are involved at least in the stimulatory effect of EFA on glucose uptake in C2C12 skeletal muscle cells. PMID:24976766

Park, So Yeon; Kim, Min Hye; Ahn, Joung Hoon; Lee, Su Jin; Lee, Jong Ho; Eum, Won Sik; Choi, Soo Young

2014-01-01

349

Fatty Acid Synthase Gene Regulation in Primary Hypothalamic Neurons  

PubMed Central

Understanding the mechanisms that regulate feeding is critical to the development of therapeutic interventions for obesity. Many studies indicate that enzymes within fatty acid metabolic pathways may serve as targets for pharmacological tools to treat this epidemic. We, and others have previously demonstrated that C75, a fatty acid synthase (FAS) inhibitor, induced significant anorexia and weight loss by both central and peripheral mechanisms. Because the hypothalamus is important in the regulation of homeostatic processes for feeding control, we have identified pathways that alter the gene expression of FAS in primary hypothalamic neuronal cultures. Insulin, glucose and AICAR (an activator of AMP-activated protein kinase) affected changes in hypothalamic FAS mRNA, which may be regulated via the SREBP1c dependent or independent pathway. PMID:17709201

Kim, Eun-Kyoung; Kleman, Amy M.; Ronnett, Gabriele V.

2009-01-01

350

A comparison of heart and liver fatty acid-binding proteins: interactions with fatty acids and possible functional differences studied with fluorescent fatty acid analogues  

Microsoft Academic Search

Fatty acid-binding proteins (FABP) are distinct but related gene products which are found in many mammalian cell types. They are generally present in high abundance, and are found in those tissues where free fatty acid (ffa) flux is high. The function(s) of FABP is unknown. Also not known is whether all FABP function similarly in their respective cell types, or

Judith Storch

1990-01-01

351

Generation of fatty acids by an acyl esterase in the bioluminescent system of Photobacterium phosphoreum  

SciTech Connect

The fatty acid reductase complex from Photobacterium phosphoreum has been discovered to have a long chain ester hydrolase activity associated with the 34K protein component of the complex. This protein has been resolved from the other components (50K and 58K) of the fatty acid reductase complex with a purity of > 95% and found to catalyze the transfer of acyl groups from acyl-CoA primarily to thiol acceptors with a low level of transfer to glycerol and water. Addition of the 50K protein of the complex caused a dramatic change in specificity increasing the transfer to oxygen acceptors. The acyl-CoA hydrolase activity increased almost 10-fold, and hence free fatty acids can be generated by the 34K protein when it is present in the fatty acid reductase complex. Hydrolysis of acyl-S-mercaptoethanol and acyl-1-glycerol and the ATP-dependent reduction of the released fatty acids to aldehyde for the luminescent reaction were also demonstrated for the reconstituted fatty acid reductase complex, raising the possibility that the immediate source of fatty acids for this reaction in vivo could be the membrane lipids and/or the fatty acid synthetase system.

Carey, L.M.; Rodriguez, A.; Meighen, E.

1984-08-25

352

Evaluating acid and base catalysts in the methylation of milk and rumen fatty acids with special emphasis on conjugated dienes and total trans fatty acids  

Microsoft Academic Search

Milk analysis is receiving increased attention. Milk contains conjugated octadecadienoic acids (18?2) purported to be anticarcinogenic,\\u000a low levels of essential fatty acids, and trans fatty acids that increase when essential fatty acids are increased in dairy rations. Milk and rumen fatty acid methyl esters\\u000a (FAME) were prepared using several acid-(HCl, BF3, acetyl chloride, H2SO4) or base-catalysts (NaOCH3, tetramethylguanidine, diazomethane), or

John K. G. Kramer; Vivek Fellner; Michael E. R. Dugan; Frank D. Sauer; Magdi M. Mossoba; Martin P. Yurawecz

1997-01-01

353

Incorporation of fatty acids by concanavalin A-stimulated lymphocytes and the effect on fatty acid composition and membrane fluidity.  

PubMed Central

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 acids replaced arachidonic acid in lymphocyte phospholipids. Fatty acid incorporation led to an alteration in lymphocyte membrane fluidity: palmitic and stearic acids decreased fluidity whereas the unsaturated fatty acids increased fluidity. It is proposed that the changes in lymphocyte phospholipid fatty acid composition and membrane fluidity brought about by culture in the presence of polyunsaturated fatty acids are responsible for the inhibition of lymphocyte functions caused by these fatty acids. PMID:8002957

Calder, P C; Yaqoob, P; Harvey, D J; Watts, A; Newsholme, E A

1994-01-01

354

Dietary Supplementation of Polyunsaturated Fatty Acids in Caenorhabditis elegans  

PubMed Central

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

Deline, Marshall L.; Vrablik, Tracy L.; Watts, Jennifer L.

2013-01-01

355

Enrichment of decanoic acid in cuphea fatty acids via distillation  

Technology Transfer Automated Retrieval System (TEKTRAN)

The introduction of a new crop often requires the development of new products and purification techniques of either the oil or fatty acids. Most new crops enter the cosmetic market first due to their high rates of returns. However, the cosmetic market often demands high purity and colorless materi...

356

Soybean ( Glycine max L. Merr.) hexane extracts inhibit cellular fatty acid uptake by reducing the expression of fatty acid transporters  

Microsoft Academic Search

Intake of saturated and trans-fatty acids is a strong risk factor for coronary heart disease. We investigated the inhibitory effects of 2 hexane extracts\\u000a from white (WBE) and black soybeans (BBE) on cellular fatty acid uptake in vitro. Transcellular uptake of elaidic acid (t18:1), a major trans-fatty acid present in processed foods, in Caco-2 monolayers was significantly reduced by 28.3

Jungae Jeun; Soung-Jin Houng; Hee-jin Jun; Ji Hae Lee; Yaoyao Jia; Sung-Joon Lee

2011-01-01

357

Fatty Acid Synthesis in Endosperm of Young Castor Bean Seedlings 1  

PubMed Central

Enzyme assays on organelles isolated from the endosperm of germinating castor bean (Ricinus communis) by sucrose density gradient centrifugation showed that fatty acid synthesis from [14C]malonyl-CoA was localized exclusively in the plastids. The optimum pH was 7.7 and the products was mainly free palmitic and oleic acids. Both NADH and NADPH were required as reductants for maximum activity. Acetyl-CoA, and acyl-carrier protein from Escherichia coli increased the rate of fatty acid synthesis, while low O2 levels suppressed synthesis. In the absence of NADPH or at low O2 concentration, stearic acid became a major product at the expense of oleic acid. Fatty acid synthesis activity was highest during the first 3 days of germination, preceding the maximum development of mitochondria and glyoxysomes. It is proposed that the plastids are the source of fatty acids incorporated into the membranes of developing organelles. PMID:16660480

Vick, Brady; Beevers, Harry

1978-01-01

358

The natural diyne-furan fatty acid EV-086 is an inhibitor of fungal delta-9 fatty acid desaturation with efficacy in a model of skin dermatophytosis.  

PubMed

Human fungal infections represent a therapeutic challenge. Although effective strategies for treatment are available, resistance is spreading, and many therapies have unacceptable side effects. A clear need for novel antifungal targets and molecules is thus emerging. Here, we present the identification and characterization of the plant-derived diyne-furan fatty acid EV-086 as a novel antifungal compound. EV-086 has potent and broad-spectrum activity in vitro against Candida, Aspergillus, and Trichophyton spp., whereas activities against bacteria and human cell lines are very low. Chemical-genetic profiling of Saccharomyces cerevisiae deletion mutants identified lipid metabolic processes and organelle organization and biogenesis as targets of EV-086. Pathway modeling suggested that EV-086 inhibits delta-9 fatty acid desaturation, an essential process in S. cerevisiae, depending on the delta-9 fatty acid desaturase OLE1. Delta-9 unsaturated fatty acids-but not saturated fatty acids-antagonized the EV-086-mediated growth inhibition, and transcription of the OLE1 gene was strongly upregulated in the presence of EV-086. EV-086 increased the ratio of saturated to unsaturated free fatty acids and phosphatidylethanolamine fatty acyl chains, respectively. Furthermore, EV-086 was rapidly taken up into the lipid fraction of the cell and incorporated into phospholipids. Together, these findings demonstrate that EV-086 is an inhibitor of delta-9 fatty acid desaturation and that the mechanism of inhibition might involve an EV-086-phospholipid. Finally, EV-086 showed efficacy in a guinea pig skin dermatophytosis model of topical Trichophyton infection, which demonstrates that delta-9 fatty acid desaturation is a valid antifungal target, at least for dermatophytoses. PMID:24189258

Knechtle, Philipp; Diefenbacher, Melanie; Greve, Katrine B V; Brianza, Federico; Folly, Christophe; Heider, Harald; Lone, Museer A; Long, Lisa; Meyer, Jean-Philippe; Roussel, Patrick; Ghannoum, Mahmoud A; Schneiter, Roger; Sorensen, Alexandra S

2014-01-01

359

Omega3 fatty acids and multiple sclerosis: relationship to depression  

Microsoft Academic Search

Depression is a common problem among patients with multiple sclerosis (MS). Previous research has shown differences between\\u000a MS patients and controls in the levels of certain fatty acids, and differences in many of these same fatty acids have also\\u000a been reported in psychiatric patients with major depression. The current study sought to determine whether fatty acid levels\\u000a in MS patients

Robin L. Aupperle; Douglas R. Denney; Sharon G. Lynch; Susan E. Carlson; Debra K. Sullivan

2008-01-01

360

Process for enzymatic hydrolysis of fatty acid triglycerides with oat caryopses  

SciTech Connect

This patent describes the process for enzymatic hydrolysis of fatty acid triglycerides to obtain free fatty acids and glycerol. It comprises: increasing the water content of dehulled whole oat caryopses to a total water content of 17 to 44% the thus moistened caryopses having active oat lipase associated with the outer surfaces thereof; contacting the moistened whole caryopses with a liquid medium, continuing the contacting until at least 20% by volume of the triglyceride reactant has been hydrolyzed to free fatty acids and glycerol, most of the free fatty acids dissolving in the oil phase external to the caryopses and most of the glycerol being absorbed into the water within the caryopses; and separating the glycerol-containing caryopses from the fatty acid-containing oil phase.

Hammond, E.G.; Lee, I.

1992-02-18

361

Glucokinase-activating GCKR polymorphisms increase plasma levels of triglycerides and free fatty acids, but do not elevate cardiovascular risk in the Ludwigshafen Risk and Cardiovascular Health Study.  

PubMed

Two strongly correlated polymorphisms located within the gene of the glucokinase regulator protein (GKRP), rs780094 and rs1260326, are associated with increased plasma triglyceride levels and provide a genetic model for the long-term activation of hepatic glucokinase. Because pharmacological glucokinase activators are evaluated for the treatment of diabetes, the aim of the study was to assess if these polymorphisms could provide evidence for an increased cardiovascular risk of long-term glucokinase activation. Therefore, these polymorphisms were tested in 3 500 patients of the Ludwigshafen Risk and Cardiovascular Health study, which was designed to assess cardiovascular risk factors. The two variants were associated with a significant increase of both plasma triglycerides (p<0.0001) and VLDL triglyceride levels (p<0.0001). Plasma free fatty acid concentrations were also significantly elevated (p<0.0078). LDL and HDL cholesterol levels were unchanged. No association was found with respect to coronary stenosis, myocardial infarction, left ventricular wall hypertrophy, and hypertension. In conclusion, long-term genetic glucokinase activation by the GKRP polymorphisms was not associated with an increased cardiovascular risk in the study population. PMID:20352598

Kozian, D H; Barthel, A; Cousin, E; Brunnhöfer, R; Anderka, O; März, W; Böhm, B; Winkelmann, B; Bornstein, S R; Schmoll, D

2010-06-01

362

Relationship between central and peripheral fatty acids in humans  

PubMed Central

Background In recent years the physiological and pathological importance of fatty acids in both the periphery and central nervous system (CNS) has become increasingly apparent. However surprisingly limited research has been conducted comparing the fatty acid composition of central and peripheral lipid stores. Methods The present study compared the distribution of polyunsaturated (PUFA), as well as specific saturated (SFA) and monounsaturated (MUFA) fatty acids in the whole blood and cerebrospinal fluid (CSF) of humans. Gas chromatography with flame ionization detection was used to determine the fatty acid profiles of twenty-eight matched CSF and whole blood samples. Multiple linear regression modeling, controlling for age, was used to identify significant relationships. Results A significant positive relationship was seen between whole blood total omega-3 fatty acids and the CSF omega-3 subfractions, docosapentaenoic acid (DPA) (P?=?0.019) and docosahexaenoic acid (DHA) (P?=?0.015). A direct association was also observed between the whole blood and CSF omega-6 PUFA, arachidonic acid (AA) (P?=?0.045). Interestingly an inverse association between central and peripheral oleic acid was also found (P?=?0.045). Conclusions These findings indicate a relationship between central and peripheral fatty acids of varying degrees of unsaturation and chain length and support the view that some systemic fatty acids are likely to cross the human blood brain barrier (BBB) and thereby influence central fatty acid concentrations. PMID:23710642

2013-01-01

363

21 CFR 573.914 - Salts of volatile fatty acids.  

Code of Federal Regulations, 2012 CFR

...2012-04-01 2012-04-01 false Salts of volatile fatty acids. 573.914... Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity...blend containing the ammonium or calcium salt of isobutyric acid and the ammonium...

2012-04-01

364

21 CFR 573.914 - Salts of volatile fatty acids.  

Code of Federal Regulations, 2014 CFR

...2014-04-01 2014-04-01 false Salts of volatile fatty acids. 573.914... Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity...blend containing the ammonium or calcium salt of isobutyric acid and the ammonium...

2014-04-01

365

21 CFR 573.914 - Salts of volatile fatty acids.  

Code of Federal Regulations, 2013 CFR

...2013-04-01 2013-04-01 false Salts of volatile fatty acids. 573.914... Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity...blend containing the ammonium or calcium salt of isobutyric acid and the ammonium...

2013-04-01

366

21 CFR 573.914 - Salts of volatile fatty acids.  

Code of Federal Regulations, 2011 CFR

...2011-04-01 2011-04-01 false Salts of volatile fatty acids. 573.914... Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity...blend containing the ammonium or calcium salt of isobutyric acid and the ammonium...

2011-04-01

367

21 CFR 573.914 - Salts of volatile fatty acids.  

Code of Federal Regulations, 2010 CFR

...2010-04-01 2010-04-01 false Salts of volatile fatty acids. 573.914... Food Additive Listing § 573.914 Salts of volatile fatty acids. (a) Identity...blend containing the ammonium or calcium salt of isobutyric acid and the ammonium...

2010-04-01

368

Production of Lipase and Oxygenated Fatty Acids from Vegetable Oils  

Technology Transfer Automated Retrieval System (TEKTRAN)

Vegetable oils such as soybean oil and corn oil are cheap raw materials. Various value-added oxygenated fatty acids have been produced from unsaturated fatty acids such as oleic and linoleic acid by biotransformation. Lipase from the non-pathogenic yeast Candida cylindracea is another important va...

369

Genotypic variation in fatty acid content of blackcurrant seeds.  

PubMed

The fatty acid composition and total fatty acid content of seeds from 36 blackcurrant genotypes developed at the Scottish Crop Research Institute were examined. A rapid small-scale procedure, involving homogenization of seeds in toluene followed by sodium methoxide transesterification and gas chromatography, was used. There was considerable variation between genotypes. The gamma-linolenic acid content generally varied from 11 to 19% of the total fatty acids, but three genotypes had higher values of 22-24%, levels previously not reported for blackcurrant seed and similar to those for borage seed. Other nutritionally important fatty acids, stearidonic acid and alpha-linolenic acid, varied from 2 to 4% and 10-19%, respectively. The mean total fatty acid contents ranged from 14 to 23% of the seed, but repeatability was poor. The results are discussed. Blackcurrant seeds are mainly byproducts from juice production, and the study shows the potential for developing blackcurrant genotypes with optimal added value. PMID:11782203

Ruiz del Castillo, M L; Dobson, G; Brennan, R; Gordon, S

2002-01-16

370

Novel branched-chain fatty acids in certain fish oils.  

PubMed

Methyl-branched fatty acids, which are usually minor components (equal or less than 0.1%) in fish oils, were concentrated in the non-urea-complexing fraction along with polyunsaturated fatty acids during the enrichment of omega-3 fatty acids from certain fish oils via the urea complexation process. The methyl-branched fatty acids in the omega-3 polyunsaturated fatty acid concentrates, which were prepared from three fish body oils, were characterized by gas chromatography and gas chromatography/mass spectrometry. Among the major branched-chain fatty acids expected and identified were the known isoprenoid acids--mainly 4,8,12-trimethyltridecanoic, pristanic, and phytanic--and the well-known iso and anteiso structures. Two novel phytol-derived multimethyl-branched fatty acids, 2,2,6,10,14-pentamethylpentadecanoic and 2,3,7,11,15-pentamethylhexadecanoic, were identified in redfish (Sebastes sp.) oil. These two fatty acids were absent in oils from menhaden (Brevoortia tyrannus) and Pacific salmon (mixed, but mostly from sockeye, Oncorhynchus nerka). The major branched-chain fatty acid in the salmon oil, 7-methyl-7-hexadecenoic acid, was also present to a moderate extent in menhaden oil. A novel vicinal dimethyl-branched fatty acid, 7,8-dimethyl-7-hexadecenoic was detected in all of the fish oils examined, but was most important in the salmon oil. Three monomethyl-branched fatty acids, 11-methyltetradecanoic acid, and 11- and 13-methylhexadecanoic, hitherto undescribed in fish lipids, were also detected in salmon, redfish and menhaden oils. PMID:2779367

Ratnayake, W M; Olsson, B; Ackman, R G

1989-07-01

371

Fatty Acid Engineering 2011 p. 1 Lipid signals: jasmonic acid & green leaf volatiles  

E-print Network

to prime other inducible defense #12;Fatty Acid Engineering 2011 p. 2 Fatty Acids and Genetic EngineeringFatty Acid Engineering 2011 p. 1 Lipid signals: jasmonic acid & green leaf volatiles i. Jasmonic occurrence of modified 'specialty' FAs - genetic transformation technology available (NB: oil seeds amenable

Constabel, Peter

372

2,6-Hexadecadiynoic Acid and 2,6-Nonadecadiynoic Acid - Novel Synthesized Acetylenic Fatty Acids as Potent Antifungal Agents  

PubMed Central

The hitherto unknown 2,6-hexadecadiynoic acid, 2,6-nonadecadiynoic acid, and 2,9-hexadecadiynoic acid were synthesized in two steps and in 11–18% overall yields starting from either 1,5-hexadiyne or 1,8-nonadiyne. Among all the compounds 2,6-hexadecadiynoic acid displayed the best overall antifungal activity against both the fluconazole resistant Candida albicans strains ATCC 14053 and ATCC 60193 (MIC = 11 ?M) and against Cryptococcus neoformans ATCC 66031 (MIC < 5.7 ?M). The 2,9-hexadecadiynoic acid did not display any significant cytotoxicity against the fluconazole resistant C. albicans strains, but it showed fungitoxicity against C. neoformans ATCC 66031 with a MIC value of <5.8 ?M. Other fatty acids, such as 2-hexadecynoic acid, 5-hexadecynoic acid, 9-hexadecynoic acid, and 6-nonadecynoic acid were also synthesized and their antifungal activities compared. The 2-hexadecynoic acid, a known antifungal fatty acid, exhibited the best antifungal activity (MIC = 9.4 ?M) against the fluconazole resistant C. albicans ATCC 14053 strain, but it showed a MIC value of only 100 ?M against C. albicans ATCC 60193. The fatty acids 2,6-hexadecadiynoic acid and 2-hexadecynoic acid also displayed a MIC of 140–145 ?M towards Mycobacterium tuberculosis H37Rv in Middlebrook 7H12 medium. In conclusion, 2,6-hexadecadiynoic acid exhibited the best fungitoxicity profile compared to other analogues. This diynoic fatty acid has the potential to be further evaluated for use in topical antifungal formulations. PMID:16933795

Carballeira, Néstor M.; Sanabria, David; Cruz, Clarisa; Parang, Keykavous; Wan, Baojie; Franzblau, Scott

2006-01-01

373

Liver Fatty Acid Binding Protein and Obesity  

PubMed Central

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

Atshaves, B.P.; Martin, G.G.; Hostetler, H.A.; McIntosh, A.L.; Kier, A.B.; Schroeder, F.

2010-01-01

374

Production of a novel antioxidant furan fatty acid from 7,10-dihydroxy-8(E)-octadecenoic acid  

Technology Transfer Automated Retrieval System (TEKTRAN)

Furan fatty acids (F-acids) have gained attention since they are known to play important roles in a variety of biological systems. Specifically F-acids are known to have strong antioxidant activity. Although widely distributed in most biological systems, F-acids are trace components and their biosyn...

375

Omega3 fatty acids as treatments for mental illness: which disorder and which fatty acid?  

Microsoft Academic Search

BACKGROUND: A growing number of observational and epidemiological studies have suggested that mental illness, in particular mood disorders, is associated with reduced dietary intake and\\/or cellular abundance of omega-3 polyunsaturated fatty acids (PUFA). This has prompted researchers to test the efficacy of omega-3 PUFA in a range of different psychiatric disorders. We have critically reviewed the double blind placebo controlled

Brian M Ross; Jennifer Seguin; Lee E Sieswerda

2007-01-01

376

Thermodynamic analysis of fatty acid esterification for fatty acid alkyl esters production  

Microsoft Academic Search

The development of renewable energy source alternatives has become a planet need because of the unavoidable fossil fuel scarcity and for that reason biodiesel production has attracted growing interest over the last decade. The reaction yield for obtaining fatty acid alkyl esters varies significantly according to the operating conditions such as temperature and the feed reactants ratio and thus investigation

Fernando A. P. Voll; Camila da Silva; Carla C. R. S. Rossi; Reginaldo Guirardello; Fernanda de Castilhos; J. Vladimir Oliveira; Lúcio Cardozo-Filho

2011-01-01

377

Solution structure and backbone dynamics of human liver fatty acid binding protein: fatty acid binding revisited.  

PubMed

Liver fatty acid binding protein (L-FABP), a cytosolic protein most abundant in liver, is associated with intracellular transport of fatty acids, nuclear signaling, and regulation of intracellular lipolysis. Among the members of the intracellular lipid binding protein family, L-FABP is of particular interest as it can i), bind two fatty acid molecules simultaneously and ii), accommodate a variety of bulkier physiological ligands such as bilirubin and fatty acyl CoA. To better understand the promiscuous binding and transport properties of L-FABP, we investigated structure and dynamics of human L-FABP with and without bound ligands by means of heteronuclear NMR. The overall conformation of human L-FABP shows the typical ?-clam motif. Binding of two oleic acid (OA) molecules does not alter the protein conformation substantially, but perturbs the chemical shift of certain backbone and side-chain protons that are involved in OA binding according to the structure of the human L-FABP/OA complex. Comparison of the human apo and holo L-FABP structures revealed no evidence for an "open-cap" conformation or a "swivel-back" mechanism of the K90 side chain upon ligand binding, as proposed for rat L-FABP. Instead, we postulate that the lipid binding process in L-FABP is associated with backbone dynamics. PMID:22713574

Cai, Jun; Lücke, Christian; Chen, Zhongjing; Qiao, Ye; Klimtchuk, Elena; Hamilton, James A

2012-06-01

378

TRPA1 Is a Polyunsaturated Fatty Acid Sensor in Mammals  

PubMed Central

Fatty acids can act as important signaling molecules regulating diverse physiological processes. Our understanding, however, of fatty acid signaling mechanisms and receptor targets remains incomplete. Here we show that Transient Receptor Potential Ankyrin 1 (TRPA1), a cation channel expressed in sensory neurons and gut tissues, functions as a sensor of polyunsaturated fatty acids (PUFAs) in vitro and in vivo. PUFAs, containing at least 18 carbon atoms and three unsaturated bonds, activate TRPA1 to excite primary sensory neurons and enteroendocrine cells. Moreover, behavioral aversion to PUFAs is absent in TRPA1-null mice. Further, sustained or repeated agonism with PUFAs leads to TRPA1 desensitization. PUFAs activate TRPA1 non-covalently and independently of known ligand binding domains located in the N-terminus and 5th transmembrane region. PUFA sensitivity is restricted to mammalian (rodent and human) TRPA1 channels, as the drosophila and zebrafish TRPA1 orthologs do not respond to DHA. We propose that PUFA-sensing by mammalian TRPA1 may regulate pain and gastrointestinal functions. PMID:22723860

Motter, Arianne L.; Ahern, Gerard P.

2012-01-01

379

Effect of w3 fatty acid on plasma lipids, cholesterol and lipoprotein fatty acid content in NIDDM patients  

Microsoft Academic Search

Summary   This study was conducted to examine the effect of ?3 fatty acid supplementation on plasma lipid, cholesterol and lipoprotein\\u000a fatty acid content of non-insulin-dependent diabetic individuals consuming a higher (0.65, n = 10) or lower (0.44, n = 18) ratio of dietary polyunsaturated to saturated fatty acid (P\\/S). The participants were initially given an olive oil\\u000a supplement (placebo) equivalent

Y. K. Goh; J. A. Jumpsen; E. A. Ryan; M. T. Clandinin

1997-01-01

380

Monitoring of Fat Content, Free Fatty Acid and Fatty Acid Profile Including trans Fat in Pakistani Biscuits  

Microsoft Academic Search

The fat contents of 12 brands of biscuits were extracted and evaluated for free fatty acids (FFA) and their fatty acid composition\\u000a (FAC). The oil content and FFA varied from 13.7 to 27.6% and 0.2 to 1.0%, respectively. The FAC was analyzed by gas chromatography–mass\\u000a spectroscopy with particular emphasis on trans fatty acids (TFA). Total saturated, unsaturated, cis-monounsaturated and polyunsaturated

Aftab Kandhro; S. T. H. Sherazi; S. A. Mahesar; M. I. Bhanger; M. Younis Talpur; Sarfraz Arain

2008-01-01

381

The biological significance of ?-oxidation of fatty acids  

PubMed Central

The author focuses on the biological significance of ?-oxidation of fatty acids. Early studies revealed that there is a subsidiary pathway for ?-oxidation of fatty acids when ?-oxidation is blocked. Many studies demonstrated that the ?-oxidation serves to provide succinyl-CoA for the citric acid cycle and for gluconeogenesis under conditions of starvation and diabetes. Acylglucosylceramides which are composed of linoleic acid, long chain ?-hydroxy fatty acids, eicosasphingenine (or trihydroxyeicosasphingenine) and glucose, are responsible for normal epidermal permeability function in the skin. It is observed that ?- and (?-1)-oxidation of fatty acids are related to energy metabolism in some laboratory animals such as musk shrews and Mongolian gerbils. Studies confirmed that ?- and (?-1)-oxidation of fatty acids play crucial roles in the production of insect pheromones of honeybees and in the formation of biopolyesters of higher plants. In addition, the biological significance of ?-oxidation of prostaglandins and leukotrienes is described. PMID:24126285

MIURA, Yoshiro

2013-01-01

382

[Raman spectrometry of several saturated fatty acids and their salts].  

PubMed

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. PMID:17260749

Luo, Man; Guan, Ping; Liu, Wen-hui; Liu, Yan

2006-11-01

383

Understanding diet and modeling changes in the omega-3 and omega-6 fatty acid composition of U.S. garrison foods for active duty personnel.  

PubMed

Research indicates that dietary omega-3 and omega-6 polyunsaturated fatty acids (PUFAs) are important in reducing the risk of mental illness. We used the DoD Survey of Health Related Behaviors among Active Duty Military Personnel (HRBS) to assess current military dietary patterns and meal locations. We used the Lands Equation to model PUFAs in a sample Garrison diet and the nutritional impact of substitution of foods higher in omega-3 PUFAs and lower in omega-6 PUFAs on tissue composition. The military diet was very poor quality compared to 2010 Healthy People Guidelines. A representative Garrison diet does not meet our estimated healthy n-3 HUFA intake at 3.5 g/d, corresponding with a tissue composition of 60% n-3 in HUFA (i.e., 40% n-6 in HUFA). Substitution of n-3 rich eggs, poultry, pork and other food commodities, combined with use on low linoleic acid oils, may contribute significantly to attaining healthier n-6/n-3 proportions in the tissue. PMID:25373102

Marriott, Bernadette P; Yu, Karina; Majchrzak-Hong, Sharon; Johnson, Jeremiah; Hibbeln, Joseph R

2014-11-01

384

Interaction of rat liver microsomes containing saturated or unsaturated fatty acids with fatty acid binding protein: peroxidation effect.  

PubMed

In the studies described here rat liver microsomes containing labeled palmitic, stearic, oleic or linoleic acids were incubated with fatty acid binding protein (FABP) and the rate of removal of 14C-labeled fatty acids from the membrane by the soluble protein was measured using a model system. More unsaturated than saturated fatty acids were removed from native liver mircrosomes incubated with similar amounts of FABP. The in vitro peroxidation of microsomal membranes mediated by ascorbate-Fe++, modified its fatty acid composition with a considerable decrease of the peroxidizability index. These changes in the microsomes facilitated the removal of oleic and linoeic acids by FABP, but the removal of palmitic and stearic acids was not modified. This effect is proposed to result from a perturbation of membrane structure following peroxidation with release of free fatty acids from susceptible domains. PMID:7845387

Catalá, A; Arcemis, C; Cerruti, A

1994-08-31

385

Surface reactions of iron - enriched smectites: adsorption and transformation of hydroxy fatty acids and phenolic acids  

NASA Astrophysics Data System (ADS)

Iron-enriched smectites play an important role in adsorption and transformation of soil organic components. Soil organo-clay complexes, and in particular humin contain hydroxy fatty acids, which are derived from plant biopolymer cutin. Phenolic acids belong to another major group of organic acids detected in soil. They participate in various soil processes, and are of concern due to their allelopathic activity. We studied the reactivity of iron-enriched smectites (Fe(III)-montmorillonite and nontronite) toward both groups of acids. We used fatty acids- 9(10),16-dihydroxypalmitic acid (diHPA), isolated from curtin, and 9,10,16-trihydroxypalmitic acid (triHPA); the following phenolic acids were used: ferulic, p-coumaric, syringic, and vanillic. Adsorption of both groups of acids was measured. The FTIR spectra of fatty acid-mineral complexes indicated inner-sphere complexation of fatty acids with iron-enriched smectites (versus outer-sphere complexation with Ca(II)-montmorillonite). The LC-MS results demonstrated enhanced esterification of fatty acids on the iron-enriched smectite surfaces (as compared to Ca(II)-montmorillonite). This study suggests that fatty acids can be esterified on the iron-enriched smectite surfaces, which results in the formation of stable organo-mineral complexes. These complexes may serve as a model for the study of natural soil organo-clay complexes and humin. The reaction of phenolic acids with Fe(III)-montmorillonite demonstrated their oxidative transformation by the mineral surfaces, which was affected by molecular structure of acids. The following order of their transformation was obtained: ferulic >syringic >p-coumaric >vanillic. The LC-MS analysis demonstrated the presence of dimers, trimers, and tetramers of ferulic acid on the surface of Fe(III)-montmorillonite. Oxidation and transformation of ferulic acid were more intense on the surface of Fe(III)-montmorillonite as compared to Fe(III) in solution due to stronger complexation on the Fe(III)-motnomrillonite surface. Our study demonstrate the importance of iron-enriched minerals for the abiotic formation of humic materials and for the transformation of aromatic (phenolic) pollutants.

Polubesova, Tamara; Olshansky, Yaniv; Eldad, Shay; Chefetz, Benny

2014-05-01

386

GATA-4, GATA-5, and GATA-6 activate the rat liver fatty acid binding protein gene in concert with HNF-1alpha.  

PubMed

Transcriptional regulation by GATA-4, GATA-5, and GATA-6 in intestine and liver was explored using a transgene constructed from the proximal promoter of the rat liver fatty acid binding protein gene (Fabpl). An immunohistochemical survey detected GATA-4 and GATA-6 in enterocytes, GATA-6 in hepatocytes, and GATA-5 in neither cell type in adult animals. In cell transfection assays, GATA-4 or GATA-5 but not GATA-6 activated the Fabpl transgene solely through the most proximal of three GATA binding sites in the Fabpl promoter. However, all three factors activated transgenes constructed from each Fabpl site upstream of a minimal viral promoter. GATA factors interact with hepatic nuclear factor (HNF)-1alpha, and the proximal Fabpl GATA site adjoins an HNF-1 site. GATA-4, GATA-5, or GATA-6 bounded to HNF-1alpha in solution, and all cooperated with HNF-1alpha to activate the Fabpl transgene. Mutagenizing all Fabpl GATA sites abrogated transgene activation by GATA factors, but GATA-4 activated the mutagenized transgene in the presence of HNF-1alpha. These in vitro results suggested GATA/HNF-1alpha interactions function in Fabpl regulation, and in vivo relevance was determined with subsequent experiments. In mice, the Fabpl transgene was active in enterocytes and hepatocytes, a transgene with mutagenized HNF-1 site was silent, and a transgene with mutagenized GATA sites had identical expression as the native transgene. Mice mosaic for biallelic Gata4 inactivation lost intestinal but not hepatic Fabpl expression in Gata4-deficient cells but not wild-type cells. These results demonstrate GATA-4 is critical for intestinal gene expression in vivo and suggest a specific GATA-4/HNF-1alpha physical and functional interaction in Fabpl activation. PMID:14715527

Divine, Joyce K; Staloch, Lora J; Haveri, Hanna; Jacobsen, Christina M; Wilson, David B; Heikinheimo, Markku; Simon, Theodore C

2004-11-01

387

Unexpected functional diversity in the fatty acid desaturases of the flour beetle Tribolium castaneum and identification of key residues determining activity.  

PubMed

Desaturases catalyse modifications to fatty acids which are essential to homeostasis and for pheromone and defensive chemical production. All desaturases of the flour beetle Tribolium castaneum were investigated via query of the sequenced genome which yielded 15 putative acyl-Coenzyme A genes. Eleven desaturase mRNA were obtained in full length and functionally expressed in yeast. Phylogenetic analysis separated the desaturases into 4 distinct clades; one clade contained conserved beetle ?9 desaturases, second clade was Tribolium-specific having diverse activities including ?5, ?9 and ?12 desaturation and the other 2 clades had mixed insect representatives. Three members of this clade contained unusual inserted sequences of ?20 residues in the C-terminal region and were related to desaturases that all contained similar inserts. Deletion of the entirety of the insert in the flour beetle ?12 desaturase abolished its activity but this was partially restored by the reintroduction of two histidine residues, suggesting the histidine(s) are required for activity but the full length insert is not. Five new desaturase activities were discovered: ?9 desaturation of C12:0-C16:0 substrates; two unprecedented ?5 enzymes acting on C18:0 and C16:0; ?9 activity exclusively on C16:0 and a further stearate ?9 desaturase. qPCR analysis ruled out a role in sex pheromone synthesis for the ?5 and ?9/C16:0 desaturases. The flour beetle genome has underpinned an examination of all transcribed desaturases in the organism and revealed a diversity of novel and unusual activities, an improved understanding of the evolutionary relationships among insect desaturases and sequence determinants of activity. PMID:24880119

Haritos, Victoria S; Horne, Irene; Damcevski, Katherine; Glover, Karen; Gibb, Nerida

2014-08-01

388

Omega3 Fatty Acids for Cardiovascular Disease Prevention  

Microsoft Academic Search

Opinion statement  Major dietary sources of omega-3 fatty acids are fish containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA),\\u000a as well as nuts, seeds, and vegetable oils containing ?-linolenic acid (ALA). Omega-3 fatty acids, especially those derived\\u000a from marine sources, may be a useful tool for the primary and secondary prevention of cardiovascular disease. Omega-3s exert\\u000a their cardioprotective effects through multiple

Andrew Paul DeFilippis; Michael J. Blaha; Terry A. Jacobson

2010-01-01

389

Fatty acid changes help to better understand regression of nonalcoholic fatty liver disease  

PubMed Central

AIM: To investigate whether liver steatosis reduction due to a six-month dietary intervention results in significant changes in the concentrations of fatty acids. METHODS: A group of 35 Caucasian individuals diagnosed with different levels of steatosis were prospectively enrolled in the present study. Analysis of the fatty acid profiles was performed according to changes in liver steatosis (liver steatosis reduction by one or two degrees) after a six-month dietary intervention. The diet helped reduce body mass in obese and overweight patients, and stabilize both glycemia and dyslipidemia. Fatty acids were extracted according to the Folch method and analyzed by gas chromatography. RESULTS: This study showed significant changes in fatty acid profiles in patients who had reduced liver steatosis by one as well as two degrees. A reduction in liver steatosis by one degree caused a significant increase in the level of the n-3 family: eicosapentaenoic acid (P < 0.055), docosapentaenoic acid-C 22:5 (P < 0.05) and docosahexaenoic acid (P < 0.05). A reduction in liver steatosis by two degrees caused a significant decrease in serum palmitoleic acid-C 16:1 (P < 0.05). CONCLUSION: Liver steatosis reduction is associated with changes in fatty acid profiles, and these changes may reflect an alteration in fatty acid synthesis and metabolism. These findings may help better understand regression of nonalcoholic fatty liver disease. PMID:25574105

Maciejewska, Dominika; Drozd, Arleta; Ossowski, Piotr; Ryterska, Karina; Jamio?-Milc, Dominika; Banaszczak, Marcin; Raszeja-Wyszomirska, Joanna; Kaczorowska, Ma?gorzata; Sabinicz, Anna; Stachowska, Ewa

2015-01-01

390

Role of volatile fatty acids in colonization resistance to Clostridium difficile.  

PubMed Central

The in vitro inhibition of Clostridium difficile by volatile fatty acids was correlated with the pH and concentrations of volatile fatty acids in the ceca of hamsters of different ages. The concentrations of cecal volatile fatty acids increased with the age of the animals. Maximum concentrations of individual volatile fatty acids were attained when the animals were ca. 19 days old, with acetic, propionic, and butyric acids occurring in the highest concentrations (72, 16, and 32 microequivalents/g of cecum, respectively). The cecal pH was approximately the same in hamsters of all ages (pH 6.6 to 7.0). Only butyric acid reached a concentration in the ceca of hamsters which was inhibitory to the in vitro multiplication of C. difficile. This inhibitory concentration was attained when the animals were ca. 19 days of age. When mixtures of volatile fatty acids were prepared at concentrations equal to those present in the ceca of hamsters, there was a direct correlation between the in vitro inhibitory activity of the volatile fatty acids and the susceptibility of hamsters 4 days of age or older to C. difficile intestinal colonization. The resistance of hamsters less than 4 days of age to C. difficile intestinal colonization appears to be due to factors other than volatile fatty acids. PMID:6735467

Rolfe, R D

1984-01-01

391

Measuring Oral Fatty Acid Thresholds, Fat Perception, Fatty Food Liking, and Papillae Density in Humans  

PubMed Central

Emerging evidence from a number of laboratories indicates that humans have the ability to identify fatty acids in the oral cavity, presumably via fatty acid receptors housed on taste cells. Previous research has shown that an individual's oral sensitivity to fatty acid, specifically oleic acid (C18:1) is associated with body mass index (BMI), dietary fat consumption, and the ability to identify fat in foods. We have developed a reliable and reproducible method to assess oral chemoreception of fatty acids, using a milk and C18:1 emulsion, together with an ascending forced choice triangle procedure. In parallel, a food matrix has been developed to assess an individual's ability to perceive fat, in addition to a simple method to assess fatty food liking. As an added measure tongue photography is used to assess papillae density, with higher density often being associated with increased taste sensitivity. PMID:24961177

Haryono, Rivkeh Y.; Sprajcer, Madeline A.; Keast, Russell S. J.

2014-01-01

392

Hepatic metabolism of free fatty acids in normal and diabetic dogs  

PubMed Central

Fasted dogs prepared with catheters in the femoral artery, portal vein, and hepatic vein and infused intravenously with palmitate-1-14C were used to estimate uptake of free fatty acids in liver and their conversion to major metabolic products secreted into hepatic venous blood. Animals were studied under ordinary conditions and when fat mobilization was increased abruptly by infusing norepinephrine or for a prolonged period by withdrawing insulin from depancreatized dogs. 80% of hepatic blood flow was assumed to be derived from the portal vein. Hepatic uptake was proportional to net outflow transport of plasma free fatty acids in the three groups and, in each, hepatic extraction fraction was about 25%. Since specific activity of free fatty acids entering and leaving the liver was equal and their composition was closely similar in the three sites sampled, it was concluded that palmitate is a representative tracer for free fatty acids entering the liver and that the liver does not release free fatty acids into the blood. In norepinephrine-infused dogs, the fraction of free fatty acids secreted in triglycerides (13%) was similar to that of control animals, so that transport of triglycerides was increased. In diabetic dogs no increased transport could be demonstrated since an average of only 2% of free fatty acids was converted to plasma triglyceride fatty acids; the hyperlipemia uniformly observed therefore appeared to result from defective removal of triglycerides from the blood. A similar fraction of free fatty acids was converted to ketones in normal and norepinephrine-infused dogs. This fraction was somewhat higher in diabetic animals and, in addition, a substantial quantity of ketones was derived from unlabeled precursors. Fractional conversion of free fatty acids to CO2 was similar in normal and norepinephrine-infused dogs, but reduced in the diabetics. PMID:5415680

Basso, Laurence V.; Havel, Richard J.

1970-01-01

393

Vertebrate fatty acyl desaturase with ?4 activity  

PubMed Central

Biosynthesis of the highly biologically active long-chain polyunsaturated fatty acids, arachidonic (ARA), eicosapentaenoic (EPA), and docosahexaenoic (DHA) acids, in vertebrates requires the introduction of up to three double bonds catalyzed by fatty acyl desaturases (Fad). Synthesis of ARA is achieved by ?6 desaturation of 18?2n - 6 to produce 18?3n - 6 that is elongated to 20?3n - 6 followed by ?5 desaturation. Synthesis of EPA from 18?3n - 3 requires the same enzymes and pathway as for ARA, but DHA synthesis reportedly requires two further elongations, a second ?6 desaturation and a peroxisomal chain shortening step. This paper describes cDNAs, fad1 and fad2, isolated from the herbivorous, marine teleost fish (Siganus canaliculatus) with high similarity to mammalian Fad proteins. Functional characterization of the cDNAs by heterologous expression in the yeast Saccharomyces cerevisiae showed that Fad1 was a bifunctional ?6/?5 Fad. Previously, functional dual specificity in vertebrates had been demonstrated for a zebrafish Danio rerio Fad and baboon Fad, so the present report suggests bifunctionality may be more widespread in vertebrates. However, Fad2 conferred on the yeast the ability to convert 22?5n - 3 to DHA indicating that this S. canaliculatus gene encoded an enzyme having ?4 Fad activity. This is a unique report of a Fad with ?4 activity in any vertebrate species and indicates that there are two possible mechanisms for DHA biosynthesis, a direct route involving elongation of EPA to 22?5n - 3 followed by ?4 desaturation, as well as the more complicated pathway as described above. PMID:20826444

Li, Yuanyou; Monroig, Oscar; Zhang, Liang; Wang, Shuqi; Zheng, Xiaozhong; Dick, James R.; You, Cuihong; Tocher, Douglas R.

2010-01-01

394

Dietary supplementation with omega-3 fatty acids prolongs platelet survival in hyperlipidemic patients with atherosclerosis  

Microsoft Academic Search

Enhanced dietary omega-3 fatty acid consumption is thought to be associated with a reduced incidence of atherothrombotic disorders. This effect may be mediated in part through suppression of in vivo platelet activity by omega-3 fatty acids. We observed that platelet survival, a sensitive indicator of in vivo platelet activity was prolonged from 6.4 +\\/- 1.5 days to 7.7 +\\/- 1.4

Peter H. Levine; Marc Fisher; Peter B. Schneider; Richard H. Whitten; Bonnie H. Weiner; Ira S. Ockene; Brian F. Johnson; Mark H. Johnson; Elizabeth M. Doyle; Patricia A. Riendeau

1989-01-01

395

Variability in the Trans Fatty Acid Content of Foods within a Food Category: Implications for Estimation of Dietary Trans Fatty Acid Intakes  

Microsoft Academic Search

Objective: Currently, the published information on trans fatty acid composition of foods is incomplete and of questionable accuracy. Detailed fatty acid analysis of over 200 foods was undertaken for the purpose of determining the variability in trans fatty acid content among foods within a product category, and the significance of this variability to the estimation of trans fatty acids intakes

Sheila M. Innis; Timothy J. Green; Thomas K. Halsey

396

40 CFR 721.10297 - Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes.  

Code of Federal Regulations, 2014 CFR

... false Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. 721.10297 Section 721.10297...10297 Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. (a)...

2014-07-01

397

40 CFR 721.10297 - Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes.  

Code of Federal Regulations, 2012 CFR

... false Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. 721.10297 Section 721.10297...10297 Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. (a)...

2012-07-01

398

40 CFR 721.10297 - Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes.  

Code of Federal Regulations, 2013 CFR

... false Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. 721.10297 Section 721.10297...10297 Tin, C16-18 and C18-unsatd. fatty acids castor-oil fatty acids complexes. (a)...

2013-07-01

399

The fatty acid composition of Octopus vulgaris paralarvae reared with live and inert food: deviation from their natural fatty acid profile  

Microsoft Academic Search

The fatty acids of the mature ovary, late eggs and wild juveniles of Octopus vulgaris were analysed to establish, in accordance with the published data on the fatty acid composition of hatchlings, a theoretical framework of the ideal fatty acid profile, i.e. the “natural” fatty acid profile, during the early life of the species. The time course variation of the

Juan C Navarro; Roger Villanueva

2003-01-01

400

Fatty Acids as Therapeutic Auxiliaries for Oral and Parenteral Formulations  

PubMed Central

Many drugs have decreased therapeutic activity due to issues with absorption, distribution, metabolism and excretion. The co-formulation or covalent attachment of drugs with fatty acids has demonstrated some capacity to overcome these issues by improving intestinal permeability, slowing clearance and binding serum proteins for selective tissue uptake and metabolism. For orally administered drugs, albeit at low level of availability, the presence of fatty acids and triglycerides in the intestinal lumen may promote intestinal uptake of small hydrophilic molecules. Small lipophilic drugs or acylated hydrophilic drugs also show increased lymphatic uptake and enhanced passive diffusional uptake. Fatty acid conjugation of small and large proteins or peptides have exhibited protracted plasma half-lives, site-specific delivery and sustained release upon parenteral administration. These improvements are most likely due to associations with lipid-binding serum proteins, namely albumin, LDL and HDL. These molecular interactions, although not fully characterized, could provide the ability of using the endogenous carrier systems for improving therapeutic outcomes. PMID:22921839

Hackett, Michael J.; Zaro, Jennica L.; Shen, Wei-Chiang; Guley, Patrick C.; Cho, Moo J.

2012-01-01