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1

Anti-androgenic activity of fatty acids.  

PubMed

In this study, we show that 5alpha-reductase derived from rat fresh liver was inhibited by certain aliphatic free fatty acids. The influences of chain length, unsaturation, oxidation, and esterification on the potency to inhibit 5alpha-reductase activity were studied. Among the fatty acids we tested, inhibitory saturated fatty acids had C12-C16 chains, and the presence of a C==C bond enhanced the inhibitory activity. Esterification and hydroxy compounds were totally inactive. Finally, we tested the prostate cancer cell proliferation effect of free fatty acids. In keeping with the results of the 5alpha-reductase assay, saturated fatty acids with a C12 chain (lauric acid) and unsaturated fatty acids (oleic acid and alpha-linolenic acid) showed a proliferation inhibitory effect on lymph-node carcinoma of the prostate (LNCaP) cells. At the same time, the testosterone-induced prostate-specific antigen (PSA) mRNA expression was down-regulated. These results suggested that fatty acids with 5alpha-reductase inhibitory activity block the conversion of testosterone to 5alpha-dihydrotestosterone (DHT) and then inhibit the proliferation of prostate cancer cells. PMID:19353546

Liu, Jie; Shimizu, Kuniyoshi; Kondo, Ryuichiro

2009-04-01

2

Antithromboplastic and thromboplastic activities of fatty acids  

PubMed Central

In the course of systematic research into the coagulative properties of cancers, facts of wider implication on the behaviour of fatty acids in relation to clotting have been uncovered. It has been shown that saturated fatty acids of appropriate chain length have a direct inhibitory effect on tissue thromboplastins with an optimum of 14 carbon atoms. Unsaturated fatty acids have a similar, though more marked, inhibitory activity with an optimum chain length of 16 carbon atoms. The inhibitory activity is reduced by combining the acids with human serum albumin. Certain fatty acids when dissolved in human serum albumin form labile thromboplastins with properties corresponding to those found in human cancers and in chorion. PMID:5602578

Fullerton, W. W.; Boggust, W. A.; O'Meara, R. A. Q.

1967-01-01

3

Physiological activities of hydroxyl fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

4

Fatty acids stimulate AMP-activated protein kinase and enhance fatty acid oxidation in L6 myotubes  

PubMed Central

We investigated the role of fatty acid availability on AMPK signalling and fatty acid oxidation in skeletal muscle. Incubating L6 skeletal muscle myotubes with palmitate (a saturated fatty acid) or linoleate (a polyunsaturated fatty acid) increased AMPK activity by 56 and 38%, respectively, compared with untreated cells. Consistent with these changes, AMPK Thr172 and acetyl-CoA carboxylase ? Ser218 phosphorylation were increased in fatty acid treated cells. Pre-incubating cells with palmitate or linoleate increased subsequent fatty acid oxidation by 86 and 92%, respectively. The enhanced AMPK signalling occurred in the absence of detectable changes in free AMP and glycogen content. The activity of the upstream kinase LKB1 was decreased by fatty acid treatment indicating that AMPK activation was not a consequence of LKB1 activation. Instead, fatty acids enhanced LKB1 phosphorylation of AMPK. Fatty acids did not alter LKB1 activity when either synthetic peptide or AMPK ?(1–312) catalytic fragment was used as substrate indicating that the ?? subunits were required for the fatty acid activation. Infection of cells with a dominant-negative AMPK adenovirus reduced basal fatty acid oxidation and inhibited the stimulatory effects of fatty acid pretreatment on fatty acid oxidation. These results indicate that increasing fatty acid availability increases AMPK activity independent of changes in the cellular energy charge and support the view that fatty acids may modulate AMPK allosterically, making it a better substrate for LKB1. PMID:16644805

Watt, Matthew J; Steinberg, Gregory R; Chen, Zhi-Ping; Kemp, Bruce E; Febbraio, Mark A

2006-01-01

5

Inhibition of hypothalamic fatty acid synthase triggers rapid activation of fatty acid oxidation in skeletal muscle  

PubMed Central

Malonyl-CoA functions as a mediator in the hypothalamic sensing of energy balance and regulates the neural physiology that governs feeding behavior and energy expenditure. The central administration of C75, a potent inhibitor of the fatty acid synthase (FAS), increases malonyl-CoA concentration in the hypothalamus and suppresses food intake while activating fatty acid oxidation in skeletal muscle. Closely correlated with the increase in muscle fatty acid oxidation is the phosphorylation/inactivation of acetyl-CoA carboxylase, which leads to reduced malonyl-CoA concentration. Lowering muscle malonyl-CoA, a potent inhibitor of carnitine/palmitoyl-CoA transferase 1 (CPT1), releases CPT1 from inhibitory constraint, facilitating the entry of fatty acids into mitochondria for ? oxidation. Also correlated with these events are C75-induced increases in the expression of skeletal muscle peroxisome proliferator-activated receptor ? (PPAR?), a transcriptional activator of fatty acid oxidizing enzymes, and uncoupling protein 3 (UCP3), a thermogenic mitochondrial uncoupling protein. Phentolamine, an ?-adrenergic blocking agent, prevents the C75-induced increases of skeletal muscle UCP3 and whole body fatty acid oxidation and C75-induced decrease of skeletal muscle malonyl-CoA. Thus, the sympathetic nervous system is implicated in the transmission of the “malonyl-CoA signal” from brain to skeletal muscle. Consistent with the up-regulation of UCP3 and PPAR? is the concomitant increase in the expression of PGC1?, transcriptional coactivator of the UCP3 and PPAR?-activated genes. These findings clarify the mechanism by which the hypothalamic malonyl-CoA signal is communicated to metabolic systems in skeletal muscle that regulate fatty acid oxidation and energy expenditure. PMID:16203972

Cha, Seung Hun; Hu, Zhiyuan; Chohnan, Shigeru; Lane, M. Daniel

2005-01-01

6

Inhibition of hypothalamic fatty acid synthase triggers rapid activation of fatty acid oxidation in skeletal muscle.  

PubMed

Malonyl-CoA functions as a mediator in the hypothalamic sensing of energy balance and regulates the neural physiology that governs feeding behavior and energy expenditure. The central administration of C75, a potent inhibitor of the fatty acid synthase (FAS), increases malonyl-CoA concentration in the hypothalamus and suppresses food intake while activating fatty acid oxidation in skeletal muscle. Closely correlated with the increase in muscle fatty acid oxidation is the phosphorylation/inactivation of acetyl-CoA carboxylase, which leads to reduced malonyl-CoA concentration. Lowering muscle malonyl-CoA, a potent inhibitor of carnitine/palmitoyl-CoA transferase 1 (CPT1), releases CPT1 from inhibitory constraint, facilitating the entry of fatty acids into mitochondria for beta oxidation. Also correlated with these events are C75-induced increases in the expression of skeletal muscle peroxisome proliferator-activated receptor alpha (PPARalpha), a transcriptional activator of fatty acid oxidizing enzymes, and uncoupling protein 3 (UCP3), a thermogenic mitochondrial uncoupling protein. Phentolamine, an alpha-adrenergic blocking agent, prevents the C75-induced increases of skeletal muscle UCP3 and whole body fatty acid oxidation and C75-induced decrease of skeletal muscle malonyl-CoA. Thus, the sympathetic nervous system is implicated in the transmission of the "malonyl-CoA signal" from brain to skeletal muscle. Consistent with the up-regulation of UCP3 and PPARalpha is the concomitant increase in the expression of PGC1alpha, transcriptional coactivator of the UCP3 and PPARalpha-activated genes. These findings clarify the mechanism by which the hypothalamic malonyl-CoA signal is communicated to metabolic systems in skeletal muscle that regulate fatty acid oxidation and energy expenditure. PMID:16203972

Cha, Seung Hun; Hu, Zhiyuan; Chohnan, Shigeru; Lane, M Daniel

2005-10-11

7

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

8

Effects of fatty acid activation on photosynthetic production of fatty acid-based biofuels in Synechocystis sp. PCC6803  

PubMed Central

Background Direct conversion of solar energy and carbon dioxide to drop in fuel molecules in a single biological system can be achieved from fatty acid-based biofuels such as fatty alcohols and alkanes. These molecules have similar properties to fossil fuels but can be produced by photosynthetic cyanobacteria. Results Synechocystis sp. PCC6803 mutant strains containing either overexpression or deletion of the slr1609 gene, which encodes an acyl-ACP synthetase (AAS), have been constructed. The complete segregation and deletion in all mutant strains was confirmed by PCR analysis. Blocking fatty acid activation by deleting slr1609 gene in wild-type Synechocystis sp. PCC6803 led to a doubling of the amount of free fatty acids and a decrease of alkane production by up to 90 percent. Overexpression of slr1609 gene in the wild-type Synechocystis sp. PCC6803 had no effect on the production of either free fatty acids or alkanes. Overexpression or deletion of slr1609 gene in the Synechocystis sp. PCC6803 mutant strain with the capability of making fatty alcohols by genetically introducing fatty acyl-CoA reductase respectively enhanced or reduced fatty alcohol production by 60 percent. Conclusions Fatty acid activation functionalized by the slr1609 gene is metabolically crucial for biosynthesis of fatty acid derivatives in Synechocystis sp. PCC6803. It is necessary but not sufficient for efficient production of alkanes. Fatty alcohol production can be significantly improved by the overexpression of slr1609 gene. PMID:22433663

2012-01-01

9

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

10

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

11

Brain fatty acid synthase activates PPAR? to maintain energy homeostasis  

PubMed Central

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 ? cells and hypothalamus produced lean, hypophagic mice with increased physical activity and impaired hypothalamic PPAR? signaling. Administration of a PPAR? agonist into the hypothalamus increased PPAR? target genes and normalized food intake. Inactivation of ? 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 PPAR?. Thus, 2 diametrically opposed proteins, FAS (induced by feeding) and PPAR? (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.

2007-01-01

12

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

13

Mutant fatty acid desaturase  

DOEpatents

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

Shanklin, John; Cahoon, Edgar B.

2004-02-03

14

Bioactive Fatty Acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

Oxygenated fatty acids are useful as specialty chemicals, plasticizers, and biomedicals. Microbial enzymes convert fatty acids to mono-, di-, and trihydroxy fatty acid products. Among them, Bacillus megaterium ALA2 converted n-6 and n-3 PUFAs to many new oxygenated fatty acids. Linoleic acid was ...

15

Mapping human brain fatty acid amide hydrolase activity with PET  

PubMed Central

Endocannabinoid tone has recently been implicated in a number of prevalent neuropsychiatric conditions. [11C]CURB is the first available positron emission tomography (PET) radiotracer for imaging fatty acid amide hydrolase (FAAH), the enzyme which metabolizes the prominent endocannabinoid anandamide. Here, we sought to determine the most suitable kinetic modeling approach for quantifying [11C]CURB that binds selectively to FAAH. Six healthy volunteers were scanned with arterial blood sampling for 90?minutes. Kinetic parameters were estimated regionally using a one-tissue compartment model (TCM), a 2-TCM with and without irreversible trapping, and an irreversible 3-TCM. The 2-TCM with irreversible trapping provided the best identifiability of PET outcome measures among the approaches studied (coefficient of variation (COV) of the net influx constant Ki and the composite parameter ?k3 (?=K1/k2) <5%, and COV(k3)<10%). Reducing scan time to 60?minutes did not compromise the identifiability of rate constants. Arterial spin labeling measures of regional cerebral blood flow were only slightly correlated with Ki, but not with k3 or ?k3. Our data suggest that ?k3 is sensitive to changes in FAAH activity, therefore, optimal for PET quantification of FAAH activities with [11C]CURB. Simulations showed that [11C]CURB binding in healthy subjects is far from a flow-limited uptake. PMID:23211960

Rusjan, Pablo M; Wilson, Alan A; Mizrahi, Romina; Boileau, Isabelle; Chavez, Sofia E; Lobaugh, Nancy J; Kish, Stephen J; Houle, Sylvain; Tong, Junchao

2013-01-01

16

Novel hybrid DHPM-fatty acids: Synthesis and activity against glioma cell growth in vitro.  

PubMed

We described the first synthesis of fatty acid 3,4-dihydropyrimidinones (DHPM-fatty acids) using the Biginelli multicomponent reaction. Antiproliferative activity on two glioma cell lines (C6 rat and U-138-MG human) was also reported. The novel DHPM-fatty acids reduced glioma cell viability relative to temozolomide. Hybrid oxo-monastrol-palmitic acid was the most potent, reducing U-138-MG human cell viability by ca. 50% at 10 ?M. In addition, the DHPM-fatty acids showed a large safety range to neural cells, represented by the organotypic hippocampal culture. These results suggest that the increased lipophilicity of DHPM-fatty acids offer a promising approach to overcoming resistance to chemotherapy and may play an important role in the development of new antitumor drugs. PMID:25863023

Treptow, Tamara G M; Figueiró, Fabrício; Jandrey, Elisa H F; Battastini, Ana M O; Salbego, Christianne G; Hoppe, Juliana B; Taborda, Priscila S; Rosa, Sabrina B; Piovesan, Luciana A; Montes D'Oca, Caroline Da R; Russowsky, Dennis; Montes D'Oca, Marcelo G

2015-05-01

17

Activation of peroxisome proliferator-activated receptor-{alpha} enhances fatty acid oxidation in human adipocytes  

SciTech Connect

Highlights: {yields} PPAR{alpha} activation increased mRNA expression levels of adipocyte differentiation marker genes and GPDH activity in human adipocytes. {yields} PPAR{alpha} activation also increased insulin-dependent glucose uptake in human adipocytes. {yields} PPAR{alpha} activation did not affect lipid accumulation in human adipocytes. {yields} PPAR{alpha} activation increased fatty acid oxidation through induction of fatty acid oxidation-related genes in human adipocytes. -- Abstract: Peroxisome proliferator-activated receptor-{alpha} (PPAR{alpha}) is a key regulator for maintaining whole-body energy balance. However, the physiological functions of PPAR{alpha} in adipocytes have been unclarified. We examined the functions of PPAR{alpha} using human multipotent adipose tissue-derived stem cells as a human adipocyte model. Activation of PPAR{alpha} by GW7647, a potent PPAR{alpha} agonist, increased the mRNA expression levels of adipocyte differentiation marker genes such as PPAR{gamma}, adipocyte-specific fatty acid-binding protein, and lipoprotein lipase and increased both GPDH activity and insulin-dependent glucose uptake level. The findings indicate that PPAR{alpha} activation stimulates adipocyte differentiation. However, lipid accumulation was not changed, which is usually observed when PPAR{gamma} is activated. On the other hand, PPAR{alpha} activation by GW7647 treatment induced the mRNA expression of fatty acid oxidation-related genes such as CPT-1B and AOX in a PPAR{alpha}-dependent manner. Moreover, PPAR{alpha} activation increased the production of CO{sub 2} and acid soluble metabolites, which are products of fatty acid oxidation, and increased oxygen consumption rate in human adipocytes. The data indicate that activation of PPAR{alpha} stimulates both adipocyte differentiation and fatty acid oxidation in human adipocytes, suggesting that PPAR{alpha} agonists could improve insulin resistance without lipid accumulation in adipocytes. The expected effects of PPAR{alpha} activation are very valuable for managing diabetic conditions accompanied by obesity, because PPAR{gamma} agonists, usually used as antidiabetic drugs, induce excessive lipid accumulation in adipocytes in addition to improvement of insulin resistance.

Lee, Joo-Young; Hashizaki, Hikari; Goto, Tsuyoshi; Sakamoto, Tomoya; Takahashi, Nobuyuki [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan); Kawada, Teruo, E-mail: fat@kais.kyoto-u.ac.jp [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)

2011-04-22

18

Antimicrobial Activity of Some N-Substituted Amides of Long-Chain Fatty Acids  

PubMed Central

Seventy-three N,N-disubstituted amides of long-chain, principally C18, fatty acids were screened for antimicrobial activity against bacteria, yeasts, and molds. Amides containing an epoxy group exhibit a broad spectrum of antimicrobial activity which is further enhanced by unsaturation. Mono-unsaturation alone does not contribute a broad level of activity to the N,N-disubstituted amides of the C18 fatty acids. PMID:5370658

Novak, Arthur F.; Solar, James M.; Mod, Robert R.; Magne, Frank C.; Skau, Evald L.

1969-01-01

19

Phosphatidate Phosphatase Activity Plays Key Role in Protection against Fatty Acid-induced Toxicity in Yeast*  

PubMed Central

The PAH1-encoded phosphatidate (PA) phosphatase in Saccharomyces cerevisiae is a pivotal enzyme that produces diacylglycerol for the synthesis of triacylglycerol (TAG) and simultaneously controls the level of PA used for phospholipid synthesis. Quantitative lipid analysis showed that the pah1? mutation caused a reduction in TAG mass and an elevation in the mass of phospholipids and free fatty acids, changes that were more pronounced in the stationary phase. The levels of unsaturated fatty acids in the pah1? mutant were unaltered, although the ratio of palmitoleic acid to oleic acid was increased with a similar change in the fatty acid composition of phospholipids. The pah1? mutant exhibited classic hallmarks of apoptosis in stationary phase and a marked reduction in the quantity of cytoplasmic lipid droplets. Cells lacking PA phosphatase were sensitive to exogenous fatty acids in the order of toxicity palmitoleic acid > oleic acid > palmitic acid. In contrast, the growth of wild type cells was not inhibited by fatty acid supplementation. In addition, wild type cells supplemented with palmitoleic acid exhibited an induction in PA phosphatase activity and an increase in TAG synthesis. Deletion of the DGK1-encoded diacylglycerol kinase, which counteracts PA phosphatase in controlling PA content, suppressed the defect in lipid droplet formation in the pah1? mutant. However, the sensitivity of the pah1? mutant to palmitoleic acid was not rescued by the dgk1? mutation. Overall, these findings indicate a key role of PA phosphatase in TAG synthesis for protection against fatty acid-induced toxicity. PMID:21708942

Fakas, Stylianos; Qiu, Yixuan; Dixon, Joseph L.; Han, Gil-Soo; Ruggles, Kelly V.; Garbarino, Jeanne; Sturley, Stephen L.; Carman, George M.

2011-01-01

20

Insulin activation of plasma non-esterified fatty acid uptake in metabolic syndrome  

PubMed Central

Objectives Insulin control of fatty acid metabolism has long been deemed dominated by suppression of adipose lipolysis. This study’s goal was to test the hypothesis that this single role of insulin is insufficient to explain observed fatty acid dynamics. Methods and Results Fatty acid kinetics were measured during a meal-tolerance test and insulin sensitivity assessed by IVGTT in overweight human subjects (n=15, BMI 35.8 ± 7.1 kg/m2). Non-steady state tracer kinetic models were formulated and tested using ProcessDB© software. Suppression of adipose release alone could not account for NEFA concentration changes postprandially, but when combined with insulin activation of fatty acid uptake was consistent with the NEFA data. The observed insulin Km for NEFA uptake was inversely correlated with both insulin sensitivity of glucose uptake (IVGTT Si) (r=?0.626, P=0.01), and whole body fat oxidation after the meal (r=?0.538, P=0.05). Conclusions These results support insulin regulation of fatty acid turnover by both release and uptake mechanisms. Activation of fatty acid uptake is consistent with the human data, has mechanistic precedent in cell culture, and highlights a new potential target for therapies aimed at improving the control of fatty acid metabolism in insulin-resistant disease states. PMID:22723441

Ramos-Roman, Maria A.; Lapidot, Smadar A.; Phair, Robert D.; Parks, Elizabeth J.

2012-01-01

21

Retinal pigment epithelial acid lipase activity and lipoprotein receptors: effects of dietary omega-3 fatty acids.  

PubMed Central

PURPOSE: To show that fish oil-derived omega-3 polyunsaturated fatty acids, delivered to the retinal pigment epithelium (RPE) by circulating low-density lipoproteins (LDL), enhance already considerable RPE lysosomal acid lipase activity, providing for more efficient hydrolysis of intralysosomal RPE lipids, an effect that may help prevent development of age-related macular degeneration (ARMD). METHODS: Colorimetric biochemical and histochemical techniques were used to demonstrate RPE acid lipase in situ, in vitro, and after challenge with phagocytic stimuli. Receptor-mediated RPE uptake of fluorescently labeled native, aceto-acetylated, and oxidized LDL was studied in vitro and in vivo. LDL effects on RPE lysosomal enzymes were assessed. Lysosomal enzyme activity was compared in RPE cells from monkeys fed diets rich in fish oil to those from control animals and in cultured RPE cells exposed to sera from these monkeys. RESULTS: RPE acid lipase activity was substantial and comparable to that of mononuclear phagocytes. Acid lipase activity increased significantly following phagocytic challenge with photoreceptor outer segment (POS) membranes. Receptor-mediated RPE uptake of labeled lipoproteins was determined in vitro. Distinctive uptake of labeled lipoproteins occurred in RPE cells and mononuclear phagocytes in vivo. Native LDL enhanced RPE lysosomal enzyme activity. RPE lysosomal enzymes increased significantly in RPE cells from monkeys fed fish oil-rich diets and in cultured RPE cells exposed to their sera. CONCLUSIONS: RPE cells contain substantial acid lipase for efficient metabolism of lipids imbibed by POS phagocytosis and LDL uptake. Diets rich in fish oil-derived omega-3 fatty acids, by enhancing acid lipase, may reduce RPE lipofuscin accumulation, RPE oxidative damage, and the development of ARMD. PMID:12545699

Elner, Victor M

2002-01-01

22

New bioactive fatty acids.  

PubMed

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)-octadecenoic acid (DOD) through 10-hydroxy-8-octadecenoic acid, and racinoleic acid to 7,10,12-trihydroxy-8-octadecenoic acid. DOD showed antibacterial activity including against food-borne pathogens. Bacillus megaterium ALA2 converted n-6 and n-3 PUFAs to many new oxygenated fatty acids. For example: linoleic acid was converted to12,13-epoxy-9-octadecenoic acid and then to 12,13-dihydroxy-9-octadecenoic acid (12,13-DHOA). From here, there are two bioconversion pathways. The major pathway is: 12,13-DHOA --> 12,13,17-trihydroxy-9(S)-octadecenoic acid (THOA) --> 12,17;13,17-diepoxy-16-hydroxy-9(Z)-octadecenoic acid (DEOA) --> 7-hydroxy-DEOA. The minor pathway is: 12,13-DHOA --> 12,13,16-THOA --> 12-hydroxy-13,16-epoxy-9(Z)-octadecenoic acid. 12,13,17-THOA has anti-plant pathogenic fungal activity. The tetrahydrofuranyl moiety is known in anti cancer drugs. Strain ALA2 also converts other n-3 and n-6 PUFAs such as eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA) and arachidonic acid (AA) to many new oxygenated unsaturated fatty acid products. All of these new products have high potential for antimicrobial agents or biomedical applications. We also screened 12 Mortierella fungal strains from the ARS Culture Collection for the production of bioactive fatty acids such as dihomo-gama-linolenic acid (DGLA) and arachidonic acid. All of the strains tested produced AA and DGLA from glucose or glycerol. The top five AA producers (mg AA/g CDW) were in the following order: M. alpina > M. zychae > M. hygrophila > M. minutissima > M. parvispora. Both AA and DGLA are important natural precursors of a large family of prostaglandin and thromboxane groups. PMID:18296335

Hou, Ching T

2008-01-01

23

Nitrogen dioxide induced changes in level of free fatty acids, triglyceride, esterified fatty acid, ganglioside and lipase activity in the guinea pig brain  

SciTech Connect

The biochemical response to controlled inhalation of nitrogen dioxide (NO2) was studied in 18 male guinea pigs. Animals were exposed to 2.5, 5.0, and 10 ppm NO2 for 2h daily for 35 consecutive days, and the results compared with six control animals exposed to filtered air for 2h daily for same period. Five biochemical parameters, including triglyceride, free fatty acids, esterified fatty acid, ganglioside and lipase activity were measured immediately after the last day of exposure. At 2.5 ppm NO2 inhalation no significant changes occurred in any region of the central nervous system (CNS). While as the dose concentration was increased to 5 and 10 ppm nitrogen dioxide, significant dose-related alteration were observed in the levels of triglyceride, free fatty acid, esterified fatty acid, ganglioside and lipase activity in the different regions of the guinea pig CNS.

Farahani, H.; Hasan, M. (Interdisciplinary Brain Research Centre, Jawaharlal Nehru Medical College, Aligarh Muslim University, (India))

1992-02-01

24

Saturated fatty acids activate TLR-mediated pro-inflammatory signaling pathways  

Technology Transfer Automated Retrieval System (TEKTRAN)

Toll-like receptor 4 (TLR4) and TLR2 were shown to be activated by saturated fatty acids (SFAs) but inhibited by docosahexaenoic acid (DHA). However, one report (ATVB 11:1944, 2009) suggested that SFA-induced TLR activation in cell culture systems is due to contaminants in BSA used for conjugating f...

25

Medium chain fatty acid ethyl esters - activation of antimicrobial effects by Malassezia enzymes.  

PubMed

Free medium and short chain fatty acids are known to have broad antimicrobial activity. However, their practical use in topical therapy is limited by their intensive smell and acidity. Surprisingly, a nearly identical antimicrobial effect was found with the ethyl ester derivatives of these fatty acids, but only against Malassezia (M.) yeast, not against Candida spp. Obviously, these esters are hydrolysed by M. enzymes, thus generating a selective activation of antimicrobial activity especially in areas well populated with these yeast ('targeting'). Octanoic acid ethyl ester (CAS 106-32-1) was found to be most suitable. In an agar dilution test, the minimal inhibitory concentrations against M. globosa, M. pachydermatis and M. sympodialis, respectively, ranged between ~5 and 10 mmol l(-1) after 10 days of incubation. The effect started immediately and was not delayed by other lipid sources applied simultaneously. Based on these data, fatty acid monoesters may represent a new therapeutic concept in M.-associated diseases. PMID:25676074

Mayser, Peter

2015-04-01

26

Phytanic acid and pristanic acid, branched-chain fatty acids associated with Refsum disease and other inherited peroxisomal disorders, mediate intracellular Ca2+ signaling through activation of free fatty acid receptor GPR40.  

PubMed

The accumulation of the two branched-chain fatty acids phytanic acid and pristanic acid is known to play an important role in several diseases with peroxisomal impairment, like Refsum disease, Zellweger syndrome and ?-methylacyl-CoA racemase deficiency. Recent studies elucidated that the toxic activity of phytanic acid and pristanic acid is mediated by multiple mitochondrial dysfunctions, generation of reactive oxygen species and Ca2+ deregulation via the InsP3-Ca2+ signaling pathway in glial cells. However, the exact signaling mechanism through which both fatty acids mediate toxicity is still under debate. Here, we studied the ability of phytanic acid and pristanic acid to activate the free fatty acid receptor GPR40, a G-protein-coupled receptor, which was described to be involved in the Ca2+ signaling of fatty acids. We treated HEK 293 cells expressing the GPR40 receptor with phytanic acid or pristanic acid. This resulted in a significant increase in the intracellular Ca2+ level, similar to the effect seen after treatment with the synthetic GPR40 agonist GW9508. Furthermore, we demonstrate that the GPR40 activation might be due to an interaction of the carboxylate moiety of fatty acids with the receptor. Our findings indicate that the phytanic acid- and pristanic acid-mediated Ca2+ deregulation can involve the activation of GPR40. Therefore, we suppose that activation of GPR40 might be part of the signaling cascade of the toxicity of phytanic and pristanic acids. PMID:21570468

Kruska, Nicol; Reiser, Georg

2011-08-01

27

Influence of ethylenediamine-n,n’-disuccinic acid (EDDS) concentration on the bactericidal activity of fatty acids in vitro  

Technology Transfer Automated Retrieval System (TEKTRAN)

The antibacterial activity of mixtures of ethylenediamine-N,N’-disuccinic acid (EDDS) and antibacterial fatty acids (FA) was examined using the agar diffusion assay. Solutions of caproic, caprylic, capric, and lauric acids dissolved in potassium hydroxide (KOH) were supplemented with 0, 5, or 10 mM ...

28

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...

29

Quantitative structure-activity relationships of antimicrobial fatty acids and derivatives against Staphylococcus aureus *  

PubMed Central

Fatty acids and derivatives (FADs) are resources for natural antimicrobials. In order to screen for additional potent antimicrobial agents, the antimicrobial activities of FADs against Staphylococcus aureus were examined using a microplate assay. Monoglycerides of fatty acids were the most potent class of fatty acids, among which monotridecanoin possessed the most potent antimicrobial activity. The conventional quantitative structure-activity relationship (QSAR) and comparative molecular field analysis (CoMFA) were performed to establish two statistically reliable models (conventional QSAR: R 2=0.942, Q 2 LOO=0.910; CoMFA: R 2=0.979, Q 2=0.588, respectively). Improved forecasting can be achieved by the combination of these two models that provide a good insight into the structure-activity relationships of the FADs and that may be useful to design new FADs as antimicrobial agents. PMID:22302421

Zhang, Hui; Zhang, Lu; Peng, Li-juan; Dong, Xiao-wu; Wu, Di; Wu, Vivian Chi-Hua; Feng, Feng-qin

2012-01-01

30

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

31

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

Microsoft Academic Search

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

Anne-Maria Pajari; Maija-Liisa Rasilo; Marja Mutanen

1997-01-01

32

Preparation and surface- active properties of polyoxyethylene-glycol (600) monoesters of fatty acids  

Microsoft Academic Search

and Summary  Polyoxyethyleneglycol (PEG-600) monoesters of undecylenic, lauric, myristic, palmitic, stearic, oleic, ricinoleic and 12-hydroxystearic\\u000a acids were prepared in 80-85% yield by reacting PEG with boric acid, esterifying the resultant borate with fatty acid, and\\u000a selectively hydrolyzing the borate ester; their surface active properties were evaluated. Increase in acyl chain length increased\\u000a the surface tension. The presence of a double bond

T. Chandrasekhara Rao; Y. Sita Rama Sastry; R. Subbarao; Gollamudi Lakshminarayana

1977-01-01

33

Carcass characteristics and fatty acid-binding protein activity in tissues of porcine and bovine species fed elevated monounsaturated fats  

E-print Network

OF FIGURES. CHAPTER TABLE OF CONTENTS , V1 . V11 1. X Xi I INTRODUCTION. II LITERATURE REVIEW III SENSORY AND CARCASS TRAITS AND FATTY ACID PROFILES OF TISSUES FROM STEERS AND SWINE FED AN ELEVATED MONO- UNSATURATED FAT DIET. Summary..., and to replace this amount of saturated fat with monounsaturated fatty acids. The style and format conforms to the Journal of Animal Science. Research also was conducted on the influence of this particular diet on fatty acid binding protein (FABP) activity...

St. John, Lori Ceanne

1986-01-01

34

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...

35

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...

36

Ileal and colonic fatty acid profiles in patients with active Crohn's disease  

Microsoft Academic Search

In patients with active Crohn's disease and in a control group the fatty acid profiles in the whole lipid fraction of ileal and colonic mucosal biopsy specimens were determined by capillary gas chromatography. The biopsy specimens in Crohn's disease patients were taken from the inflamed terminal ileum as well as from the inflamed and macroscopically normal colon. Compared with controls

S Bühner; E Nagel; J Körber; H Vogelsang; T Linn; R Pichlmayr

1994-01-01

37

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...

38

Cholesterol and omega-3 fatty acids inhibit Na, K-ATPase activity in human endothelial cells.  

PubMed

We have investigated the effects of cholesterol and omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexenoic acid (DHA) on Na, K-ATPase activity in human endothelial cells (HUVEC). Cultured HUVEC were incubated for 18 h with pure egg phosphatidylcholine (PC), or cholesterol-enriched liposomes (4 mg PC/ml). EPA and DHA alpha-tocopherol-acetate were emulsified with PC and incubated with HUVEC (10 mM). Na, K-ATPase and 5'-nucleotidase activities were determined using the coupled assay method on microsomal fractions obtained from cultured cells using non treated cells as control. Cholesterol enrichment significantly reduced both Na, K-ATPase and 5'-nucleotidase activities by a similar level (- 40%), whereas pure phospholipid liposomes inhibited this activity only by 22%. The dose-response curves of Na, K-ATPase activity were all biphasic assuming the presence of two independent sites exhibiting different affinities for ouabain of nM and microM respectively. The cholesterol induced inhibitory effect was greater for low affinity sites (-54%) as compared to that of the high affinity sites (-24%) whereas omega-3 fatty acids reduced the activity of both sites by 22%. Short term effects of EPA and DHA on Na, K-ATPase activity were determined by incubating microsomal fractions from untreated cells with various concentrations of free fatty acids (from 1 to 200 microM) for 20 min. Both EPA and DHA significantly reduced Na, K-ATPase activity but inhibition by EPA seems to be more effective than DHA. These results suggest that cholesterol and omega-3 fatty acids reduce Na, K-ATPase activity in HUVEC. PMID:10030384

Mayol, V; Duran, M J; Gerbi, A; Dignat-George, F; Lévy, S; Sampol, J; Maixent, J M

1999-02-01

39

Omega-3 Fatty Acids  

MedlinePLUS

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

40

Fats and fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

The absolute fat requirement of the human species is the amount of essential fatty acids needed to maintain optimal fatty acid composition of all tissues and normal eicosanoid synthesis. At most, this requirement is no more than about 5% of an adequate energy intake. However, fat accounts for appro...

41

Halogenated fatty acids  

Microsoft Academic Search

Chlorinated fatty acids have been found to be major contributors to organohalogen compounds in fish, bivalves, jellyfish, and lobster, and they have been indicated to contribute considerably to organohalogens in marine mammals. Brominated fatty acids have been found in marine sponges. Also, chlorinated lipids have been found in meat exposed to hypochlorite disinfected water, and in chlorine-treated flour and in

Peter Sundin

1997-01-01

42

Cytochrome b5 Coexpression Increases Tetrahymena thermophila ?6 Fatty Acid Desaturase Activity in Saccharomyces cerevisiae  

PubMed Central

Very-long-chain polyunsaturated fatty acids such as arachidonic, eicosapentaenoic, and docosahexaenoic acids, are important to the physiology of many microorganisms and metazoans and are vital to human development and health. The production of these and related fatty acids depends on ?6 desaturases, the final components of an electron transfer chain that introduces double bonds into 18-carbon fatty acid chains. When a ?6 desaturase identified from the ciliated protist Tetrahymena thermophila was expressed in Saccharomyces cerevisiae cultures supplemented with the 18:2?9,12 substrate, only 4% of the incorporated substrate was desaturated. Cytochrome b5 protein sequences identified from the genome of T. thermophila included one sequence with two conserved cytochrome b5 domains. Desaturation by the ?6 enzyme increased as much as 10-fold when T. thermophila cytochrome b5s were coexpressed with the desaturase. Coexpression of a cytochrome b5 from Arabidopsis thaliana with the ?6 enzyme also increased desaturation. A split ubiquitin growth assay indicated that the strength of interaction between cytochrome b5 proteins and the desaturase plays a vital role in fatty acid desaturase activity, illustrating the importance of protein-protein interactions in this enzyme activity. PMID:23584993

Dahmen, Jeremy L.; Olsen, Rebecca; Fahy, Deirdre; Wallis, James G.

2013-01-01

43

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...

44

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

45

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  

Microsoft Academic Search

1.?The relationship between concetrations 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

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

2009-01-01

46

Fatty acid metabolism of isolated mammalian cells.  

PubMed

It is now clear that a wide variety of differentiated cells in culture exhibit essentially the full spectrum of mammalian fatty acid metabolism. These cells readily incorporate free fatty acids into membrane phosphoglycerides, modify exogenous fatty acids by desaturation and elongation, and store excess fatty acyl groups, primarily as triacylglycerols. Similarly, many different types of cells synthesize cyclooxygenase and lipoxygenase derivatives of long chain polyunsaturated fatty acids. Furthermore, although the fatty acid composition of cellular phospholipids can be modified by medium supplementation, cells in culture exhibit definite fatty acyl specificities for the various steps of fatty acid activation, transesterification and release. As the extensive repertoire of fatty acid metabolism in mammalian cells has been elucidated, and as the ability to grow differentiated cells in culture has increased, new questions have arisen. There is still much to be learned about the enzymes involved in synthesizing and maintaining the unique fatty acid composition of the different cellular phospholipids and the processes which regulate the desaturation, elongation and retroconversion of polyunsaturated fatty acids. Other areas of great current interest are the mechanisms by which certain long chain polyunsaturated fatty acids are made available for conversion to oxygenated, biologically-active derivatives, the metabolic interactions between different polyunsaturated fatty acids, particularly n-3 and n-6 fatty acids, the cellular roles of the C22 polyunsaturated fatty acids, and the functions of particular molecular species of phospholipids in membrane-mediated events. Further research in these areas will contribute to unravelling the role of fatty acids and fatty acid derivatives in the physiological processes of mammalian cells. PMID:3310011

Rosenthal, M D

1987-01-01

47

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

48

Fatty Acids Activate a Chimera of the Clofibric Acid-Activated Receptor and the Glucocorticoid Receptor  

Microsoft Academic Search

Peroxisome proliferators such as clofibric acid, nafenopin, and WY-14,643 have been shown to activate PPAR (peroxisome proliferator-activated receptor), a member of the steroid nuclear receptor superfamily. We have cloned the cDNA from the rat that is homologous to that from the mouse [Issemann, I. & Green, S. (1990) Nature (London) 347, 645-650], which encodes a 97% similar protein with a

Martin Gottlicher; Eva Widmark; Qiao Li; Jan-Ake Gustafsson

1992-01-01

49

Fatty acid synthase inhibition activates AMP-activated protein kinase in SKOV3 human ovarian cancer cells.  

PubMed

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 in vivo. In this report, we explore the cytotoxic mechanism of action of FAS inhibition and show that C93, a synthetic FAS inhibitor, increases the AMP/ATP ratio, activating AMPK in SKOV3 human ovarian cancer cells, which leads to cytotoxicity. As a physiologic consequence of AMPK activation, acetyl-CoA carboxylase (ACC), the rate-limiting enzyme of fatty acid synthesis, was phosphorylated and inhibited whereas glucose oxidation was increased. Despite these attempts to conserve energy, the AMP/ATP ratio increased with worsening cellular redox status. Pretreatment of SKOV3 cells with compound C, an AMPK inhibitor, substantially rescued the cells from C93 cytotoxicity, indicating its dependence on AMPK activation. 5-(Tetradecyloxy)-2-furoic acid, an ACC inhibitor, did not activate AMPK despite inhibiting fatty acid synthesis pathway activity and was not significantly cytotoxic to SKOV3 cells. This indicates that substrate accumulation from FAS inhibition triggering AMPK activation, not end-product depletion of fatty acids, is likely responsible for AMPK activation. C93 also exhibited significant antitumor activity and apoptosis against SKOV3 xenografts in athymic mice without significant weight loss or cytotoxicity to proliferating cellular compartments such as bone marrow, gastrointestinal tract, or skin. Thus, pharmacologic FAS inhibition selectively activates AMPK in ovarian cancer cells, inducing cytotoxicity while sparing most normal human tissues from the pleiotropic effects of AMPK activation. PMID:17409402

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

2007-04-01

50

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.

51

Phytochemical analysis, antioxidant activity, fatty acids composition, and functional group analysis of Heliotropium bacciferum.  

PubMed

Heliotropium bacciferum is paramount in medicinal perspective and belongs to Boraginaceae family. The crude and numerous fractions of leaves, stem, and roots of the plant were investigated for phytochemical analysis and DPPH radical scavenging activity. Phytochemical analysis of crude and fractions of the plant revealed the presence of alkaloids, saponins, tannins, steroids, terpenoids, flavonoids, glycosides, and phenols. The antioxidant (free radical scavenging) activity of various extracts of the Heliotropium bacciferum was resolute against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with the avail of UV spectrophotometer at 517?nm. The stock solution (1000?mg/mL) and then several dilutions (50, 100, 150, 200, and 250?mg/mL) of the crude and fractions were prepared. Ascorbic acid was used as a standard. The plant leaves (52.59 ± 0.84 to 90.74 ± 1.00), stem (50.19 ± 0.92 to 89.42 ± 1.10), and roots extracts (49.19 ± 0.52 to 90.01 ± 1.02) divulged magnificent antioxidant activities. For the ascertainment of the fatty acid constituents a gas chromatograph hyphenated to mass spectrometer was used. The essential fatty acids for growth maintenance such as linoleic acid (65.70%), eicosadienoic acid (15.12%), oleic acid (8.72%), and palmitic acid (8.14%) were found in high percentage. The infrared spectra of all extracts of the plant were recorded by IR Prestige-21 FTIR model. PMID:25489605

Ahmad, Sohail; Ahmad, Shabir; Bibi, Ahtaram; Ishaq, Muhammad Saqib; Afridi, Muhammad Siddique; Kanwal, Farina; Zakir, Muhammad; Fatima, Farid

2014-01-01

52

Phytochemical Analysis, Antioxidant Activity, Fatty Acids Composition, and Functional Group Analysis of Heliotropium bacciferum  

PubMed Central

Heliotropium bacciferum is paramount in medicinal perspective and belongs to Boraginaceae family. The crude and numerous fractions of leaves, stem, and roots of the plant were investigated for phytochemical analysis and DPPH radical scavenging activity. Phytochemical analysis of crude and fractions of the plant revealed the presence of alkaloids, saponins, tannins, steroids, terpenoids, flavonoids, glycosides, and phenols. The antioxidant (free radical scavenging) activity of various extracts of the Heliotropium bacciferum was resolute against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with the avail of UV spectrophotometer at 517?nm. The stock solution (1000?mg/mL) and then several dilutions (50, 100, 150, 200, and 250?mg/mL) of the crude and fractions were prepared. Ascorbic acid was used as a standard. The plant leaves (52.59 ± 0.84 to 90.74 ± 1.00), stem (50.19 ± 0.92 to 89.42 ± 1.10), and roots extracts (49.19 ± 0.52 to 90.01 ± 1.02) divulged magnificent antioxidant activities. For the ascertainment of the fatty acid constituents a gas chromatograph hyphenated to mass spectrometer was used. The essential fatty acids for growth maintenance such as linoleic acid (65.70%), eicosadienoic acid (15.12%), oleic acid (8.72%), and palmitic acid (8.14%) were found in high percentage. The infrared spectra of all extracts of the plant were recorded by IR Prestige-21 FTIR model. PMID:25489605

Ahmad, Sohail; Ahmad, Shabir; Bibi, Ahtaram; Ishaq, Muhammad Saqib; Afridi, Muhammad Siddique; Kanwal, Farina; Zakir, Muhammad; Fatima, Farid

2014-01-01

53

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

54

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

55

Omega3 Fatty Acids  

Microsoft Academic Search

The research conducted in avians with emphasis on omega (?)-3 fatty acid enrichment of edible meat portions and the use of\\u000a fertilized eggs as a unique model for nutrition research is addressed. In a typical Western diet, over 70% of dietary fat\\u000a is supplied through animal products. Considering the health benefits of ?-3 fatty acids, feeding strategies have been adopted

Gita Cherian

56

Cyclic fatty acid monomers from dietary heated fats affect rat liver enzyme activity  

Microsoft Academic Search

This study was conducted to investigate the effects of dietary cyclic fatty acid monomers (CFAM), contained in heated fat\\u000a from a commercial deep-fat frying operation, on rat liver enzyme activity. A partially hydrogenated soybean oil (PHSBO) used\\u000a 7 d (7-DH) for frying foodstuffs, or 0.15% methylated CFAM diets was fed to male weanling rats in comparison to a control\\u000a group

Courdjo Lamboni; Jean-Louis Sébédio; Edward G. Perkins

1998-01-01

57

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

58

Antioxidant activity and fatty acid profile of fermented milk prepared by Pediococcus pentosaceus.  

PubMed

Probiotics are the class of beneficial microorganisms that have positive influence on the health when ingested in adequate amounts. Probiotic fermented milk is one of the dairy products that is prepared by using probiotic lactic acid bacteria. The study comprised preparation of fermented milk from various sources such as cow, goat and camel. Pediococcus pentosaceus which is a native laboratory isolate from cheese was utilized for the product formation. Changes in functional properties in the fermented milks obtained from three different species were evaluated. Antioxidant activity determined by DPPH assay showed activity in probiotic fermented milk obtained from all the products being highest in goat milk (93 %) followed by product from camel milk (86 %) and then product from cow milk (79 %). The composition of beneficial fatty acids such as stearic acid, oleic acid and linoleic acid were higher in fermented milk than the unfermented ones. Results suggested that probiotic bacteria are able to utilize the nutrients in goat and camel milk more efficiently compared to cow milk. Increase in antioxidant activity and fatty acid profile of fermented milks enhances the therapeutic value of the products. PMID:25477694

Balakrishnan, Gayathri; Agrawal, Renu

2014-12-01

59

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

60

Fatty Acid Carcass Mapping  

E-print Network

positively correlated with the MUFA:SFA ratio. Also, the perception of beef can be influenced by the oleic acid concentration. Because fatty acids have very different melting points, variation in their composition has an important effect on firmness... or softness of the fat in meat, especially the s.c. and i.m. fats (Wood et al., 2003). This can also alter shelf-life depending on the double bonds of the unsaturated fatty acids, whether or not they will oxidize rapidly and become rancid and discolored...

Turk, Stacey N.

2010-01-14

61

Antibacterial activity of 2-alkynoic fatty acids against multidrug resistant bacteria  

PubMed Central

The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogues in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 ?g/mL), Staphylococcus saprophyticus (MIC = 15.5 ?g/mL), and Bacillus cereus (MIC = 31.3 ?g/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 ?g/mL) and Pseudomonas aeruginosa (MIC = 125 ?g/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 ?g/mL) and clinical isolates of MRSA (MIC = 3.9 ?g/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 as well as the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations. PMID:24365283

Sanabria-Ríos, David J.; Rivera-Torres, Yaritza; Maldonado-Domínguez, Gamalier; Domínguez, Idializ; Ríos, Camille; Díaz, Damarith; Rodríguez, José W.; Altieri-Rivera, Joanne S.; Ríos-Olivares, Eddy; Cintrón, Gabriel; Montano, Nashbly; Carballeira, Néstor M.

2014-01-01

62

Mechanism by Which Fatty Acids Inhibit Insulin Activation of Insulin Receptor Substrate1 (IRS-1)-associated Phosphatidylinositol 3Kinase Activity in Muscle  

Microsoft Academic Search

Recent studies have demonstrated that fatty acids in- duce insulin resistance in skeletal muscle by blocking insulin activation of insulin receptor substrate-1 (IRS- 1)-associated phosphatidylinositol 3-kinase (PI3-ki- nase). To examine the mechanism by which fatty acids mediate this effect, rats were infused with either a lipid emulsion (consisting mostly of 18:2 fatty acids) or glyc- erol. Intracellular C18:2 CoA increased

Chunli Yu; Yan Chen; Gary W. Cline; Dongyan Zhang; Haihong Zong; Yanlin Wang; Raynald Bergeron; Jason K. Kim; Samuel W. Cushman; Gregory J. Cooney; Bronwyn Atcheson; Morris F. White; Edward W. Kraegen; Gerald I. Shulman

2002-01-01

63

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

64

Taxonomy of the Neisseriae: Fatty Acid Analysis, Aminopeptidase Activity, and Pigment Extraction  

Microsoft Academic Search

The cellular fatty acids of reference strains of most of the currently recognized species of Neisseria and Branhamella species were examined. Analysis of fatty acids with chain lengths of over 12 carbons supported the division of the species into two groups. Group I, comprised of N. meningitidis, N. gonorrhoeae, N. Java, N. subJava, N. per-ava, N. sicca, N. mucosa, N.

CAROLYN HOKE; NEYLAN A. VEDROS

65

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

Microsoft Academic Search

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,

Zhen Zhang; Shouyu Wang; Yunpeng Diao; Jianing Zhang; Decheng Lv

2010-01-01

66

Inhibition of fatty acid and cholesterol synthesis by stimulation of AMP-activated protein kinase  

Microsoft Academic Search

AMP-activated protein kinase is a mul- tisubstrate protein kinase that, in liver, inactivates both acetyl-CoA carboxylase, the rate-limiting enzyme of fatty acid synthesis, and 3-hydroxy-3-methyl-glutaryl-CoA reductase, the rate-limiting enzyme of cholesterol synthe- sis. AICAR (5-amino 4-imidazolecarboxamide ribotide, ZMP) was found to stimulate up to 10-fold rat liver AMP-activated protein kinase, with a half-maximal effect at approximately 5 mM. In accordance

NATHALIE HENIN; M-FRAwcOISE VINCENT; HARRY E. GRUBER

67

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

68

The influence of dietary fat on the lipogenic activity and fatty acid composition of rat white adipose tissue  

Microsoft Academic Search

The in vivo fatty acid synthesis rate, selected enzyme activities and fatty acid composition of rat white adipose tissue from\\u000a animals fed semisynthetic diets of differing fat type and content were studied. All animals were starved for 48 hr and then\\u000a refed a fat-free (FF) diet for 48 hr. They were then divided into three groups. One group was continued

Gary J. Nelson; Darshan S. Kelley; Perla C. Schmidt; Claire M. Serrato

1987-01-01

69

Altered Constitutive Expression of Fatty Acid-metabolizing Enzymes in Mice Lacking the Peroxisome Proliferator-activated  

E-print Network

Proliferator-activated Receptor (PPAR )* (Received for publication, October 22, 1997) Toshifumi Aoyama University School of Medicine, Matsumoto, Nagano 390, Japan Peroxisome proliferator-activated receptor (PPAR. Constitutive liver -oxida- tion of the long chain fatty acid, palmitic acid, was lower in the PPAR null mice

Omiecinski, Curtis

70

Comparative effects of perilla and fish oils on the activity and gene expression of fatty acid oxidation enzymes in rat liver  

Microsoft Academic Search

The activity and mRNA level of hepatic enzymes in fatty acid oxidation and synthesis were compared in rats fed diets containing either 15% saturated fat (palm oil), safflower oil rich in linoleic acid, perilla oil rich in ?-linolenic acid or fish oil rich in eicosapentaenoic (EPA) and docosahexaenoic acids (DHA) for 15 days. The mitochondrial fatty acid oxidation rate was

Takashi Ide; Hideyuki Kobayashi; Lakshmikuttyamma Ashakumary; Isabelle A. Rouyer; Yoko Takahashi; Toshifumi Aoyama; Takashi Hashimoto; Michinao Mizugaki

2000-01-01

71

Inhibitory Activities of Omega-3 Fatty Acids and Traditional African Remedies on Keloid Fibroblasts  

PubMed Central

Keloids develop when scar tissue responds to skin trauma with proliferative fibrous growths that extend beyond the boundaries of the original wound and progress for several months or years. Keloids most frequently occur in individuals of indigenous sub-Saharan African origin. The etiology for keloids is still unknown and treatment can be problematic as patients respond differently to various treatment modalities. Keloids have a high rate of recurrence following surgical excision. Some West African patients claim to have had successful outcomes with traditional African remedies—boa constrictor oil (BCO) and shea butter—leading the authors to investigate their effects on cultured fibroblasts. The effects of emulsions of BCO, fish oil, isolated omega-3 fatty acids, and shea butter were tested in comparison to triamcinolone regarding inhibition of cell growth in keloid and control fibroblast cultures. In a series of controlled studies, it was observed that fish oil and BCO were more effective than triamcinolone, and that cis-5, 8, 11, 14, 17-eicosapentaenoic acid was more effective than -linolenic acid. While cell counts in control cultures continuously decreased over a period of 5 days, cell counts in keloid cultures consistently declined between day 1 and day 3, and then increased between day 3 and day 5 for all tested reagents except for fish oil. These results suggest that oils rich in omega-3 fatty acids may be effective in reducing actively proliferating keloid fibroblasts. Additional studies are warranted to investigate whether oils rich in omega-3 fatty acids offer effective and affordable treatment for some keloid patients, especially in the developing world. PMID:24489452

Olaitan, Peter B.; Chen, I-Ping; Norris, James E.C.; Feinn, Richard; Oluwatosin, Odunayo M.; Reichenberger, Ernst J.

2012-01-01

72

Omega-3 fatty acids (image)  

MedlinePLUS

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

73

Stearoyl-CoA desaturase 1 deficiency increases fatty acid oxidation by activating AMP-activated protein kinase in liver  

PubMed Central

Stearoyl-CoA desaturase (SCD) catalyzes the rate-limiting step in the biosynthesis of monounsaturated fatty acids. Mice with a targeted disruption of the SCD1 isoform have reduced body adiposity, increased energy expenditure, and up-regulated expression of several genes encoding enzymes of fatty acid ?-oxidation in liver. The mechanisms by which SCD deficiency leads to these metabolic changes are presently unknown. Here we show that the phosphorylation and activity of AMP-activated protein kinase (AMPK), a metabolic sensor that regulates lipid metabolism during increased energy expenditure is significantly increased (?40%, P < 0.01) in liver of SCD1 knockout mice (SCD1-/-). In parallel with the activation of AMPK, the phosphorylation of acetyl-CoA carboxylase at Ser-79 was increased and enzymatic activity was decreased (?35%, P < 0.001), resulting in decreased intracellular levels of malonyl-CoA (?47%, P < 0.001). An SCD1 mutation also increased AMPK phosphorylation and activity and increased acetyl-CoA carboxylase phosphorylation in leptin-deficient ob/ob mice. Lower malonyl-CoA concentrations are known to derepress carnitine palmitoyltransferase 1 (CPT1). In SCD1-/- mice, CPT1 and CPT2 activities were significantly increased (in both cases ?60%, P < 0.001) thereby stimulating the oxidation of mitochondrial palmitoyl-CoA. Our results identify AMPK as a mediator of increased fatty acid oxidation in liver of SCD1-deficient mice. PMID:15096593

Dobrzyn, Pawel; Dobrzyn, Agnieszka; Miyazaki, Makoto; Cohen, Paul; Asilmaz, Esra; Hardie, D. Grahame; Friedman, Jeffrey M.; Ntambi, James M.

2004-01-01

74

Mitochondrial long chain fatty acid oxidation, fatty acid translocase/CD36 content and carnitine palmitoyltransferase I activity in human skeletal muscle during aerobic exercise  

PubMed Central

Mitochondrial fatty acid transport is a rate-limiting step in long chain fatty acid (LCFA) oxidation. In rat skeletal muscle, the transport of LCFA at the level of mitochondria is regulated by carnitine palmitoyltransferase I (CPTI) activity and the content of malonyl-CoA (M-CoA); however, this relationship is not consistently observed in humans. Recently, fatty acid translocase (FAT)/CD36 was identified on mitochondria isolated from rat and human skeletal muscle and found to be involved in LCFA oxidation. The present study investigated the effects of exercise (120 min of cycling at ?60% V?O2peak) on CPTI palmitoyl-CoA and M-CoA kinetics, and on the presence and functional significance of FAT/CD36 on skeletal muscle mitochondria. Whole body fat oxidation rates progressively increased during exercise (P < 0.05), and concomitantly M-CoA inhibition of CPTI was progressively attenuated. Compared to rest, 120 min of cycling reduced (P < 0.05) the inhibition of 0.7, 2, 5 and 10 ?m M-CoA by 16%, 21%, 30% and 34%, respectively. Whole body fat oxidation and palmitate oxidation rates in isolated mitochondria progressively increased (P < 0.05) during exercise, and were positively correlated (r = 0.78). Mitochondrial FAT/CD36 protein increased by 63% (P < 0.05) during exercise and was significantly (P < 0.05) correlated with mitochondrial palmitate oxidation rates at all time points (r= 0.41). However, the strongest (P < 0.05) correlation was observed following 120 min of cycling (r= 0.63). Importantly, the addition of sulfo-N-succimidyloleate, a specific inhibitor of FAT/CD36, reduced mitochondrial palmitate oxidation to ?20%, indicating FAT/CD36 is functionally significant with respect to LCFA oxidation. We hypothesize that exercise-induced increases in fatty acid oxidation occur as a result of an increased ability to transport LCFA into mitochondria. We further suggest that decreased CPTI M-CoA sensitivity and increased mitochondrial FAT/CD36 protein are both important for increasing whole body fatty acid oxidation during prolonged exercise. PMID:16357012

Holloway, Graham P; Bezaire, Veronic; Heigenhauser, George J F; Tandon, Narendra N; Glatz, Jan F C; Luiken, Joost J F P; Bonen, Arend; Spriet, Lawrence L

2006-01-01

75

[Antioxidant activity of vegetable oils with various omega-6/omega-3 fatty acids ratio].  

PubMed

Antioxidant activity and the oxidative stability were investigated in flax, sesame, silybum oils and oils with different omega-6/omega-3 fatty acid ratio. The content of antioxidants (AO) in crude oils and their reactivity towards peroxyl radicals were studied using kinetic method for addition of oil in a model reaction of cumol oxidation. There were correlations between PUFA/omega-9 and thermal stability (50 degrees C); between gamma-tocopherol content and resistantance to oxidative changes after storage at (10 +/- 2) degrees C for 6 months. PMID:20695213

Guseva, D A; Prozorovskaia, N N; Shironin, A V; Sanzhakov, M A; Evteeva, N M; Rusina, I F; Kasaikina, O T

2010-01-01

76

Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities.  

PubMed

A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity. PMID:20392645

Xiang, Hua; Zhao, Wei; Xiao, Hong; Qian, Lei; Yao, Yao; Li, Xiao-Bo; Liao, Qing-Jiang

2010-05-01

77

Fatty Acid Composition and Fatty Acid Elongase and Stearoyl-CoA Desaturase Activities in Tissues of Steers Fed High Oleate Sunflower Seed1'2  

Microsoft Academic Search

ABSTRACT The effects of a high oleate sunflower,seed diet on tissue composition,and,on fatty acid elongation and,desaturation,enzyme,activities were,investigated. Three Simmental,calves were,fed a standard,corn-based diet (2.6% fat); three others,were,fed the,corn-based diet containing,20% high oleate sunflower,seed,(10.4% fat). Blood samples,and perianal adipose,tissue samples were obtained at 7, 90 and 180 d on trial. Samples of liver, longissimus dorsi muscle and intestinal mucosa were obtained,at

Joyce H. P. Chang

78

Cyclic fatty acid monomers from heated oil modify the activities of lipid synthesizing and oxidizing enzymes in rat liver.  

PubMed

Cyclic fatty acid monomers purified from a heated linseed oil were given for 2 wk to adult rats as triacylglycerol at two dose levels, i.e., 0.1 and 1 g/100 g diet, to determine their effect on some aspects of lipid metabolism. Indirect evidence of a peroxisome proliferator-like effect was observed, as determined by an elevation of some characteristic enzyme activities, such as peroxisomal acyl-CoA oxidase, and the microsomal omega- but also (omega-1)-laurate hydroxylase (CYP4A1 and CYP2E1, respectively). The dietary cyclic fatty acids induced a coordinated regulation between the activities of the lipogenic enzymes studied (Delta9-desaturase, phosphatidate phosphohydrolase) and peroxisomal oxidation, but not with mitochondrial beta-oxidation. The dose-dependent decrease of Delta9-desaturase activity (P < 0.05) with cyclic fatty acid monomer intake was accompanied by a similar decrease of the monounsaturated fatty acid level in liver. The increase in the gamma-linolenic acid level also suggested an increase in Delta6-desaturase activity with cyclic fatty acid intake (P < 0.05). In addition, our results strongly suggested that the altered liver levels of eicosapentaenoic and arachidonic acids were due to the peroxisomal retroconversion process in rats fed cyclic acids. Finally, an effect of these cyclic compounds on the carbohydrate metabolism cannot be disregarded because they decreased liver glycogen concentration. We conclude that cyclic fatty acid monomers affect different aspects of lipid metabolism, including a phenotypic peroxisome proliferator response. This provides the ground for further studies investigating the biochemical pathways that underlie the nutritional effect of such molecules. PMID:10827204

Martin, J C; Joffre, F; Siess, M H; Vernevaut, M F; Collenot, P; Genty, M; Sébédio, J L

2000-06-01

79

Changes in lipid composition and lipogenic enzyme activities in liver of lambs fed omega-6 polyunsaturated fatty acids.  

PubMed

Twenty-four lambs (Ovis aries) were used in a 45-day finishing study to evaluate the effects of feeding diets high in linoleic acid (C(18:2), omega-6) on liver lipid composition and on lipogenic enzyme activities in subcellular fractions of liver. Lambs were fed either a 5% safflower oil (SO, high linoleic acid) supplemented diet or a control diet without added oil. SO feeding caused a reduction in the amount of serum and liver triacylglycerols and cholesterol, whereas the level of phospholipids in both tissues was hardly affected. In liver of SO-treated lambs an increase in the levels of C(18:2) and arachidonic acid (C(20:4), omega-6), together with a simultaneous decrease of saturated fatty acids, was observed. In comparison to rat liver, rather low activities of enzymes in the pathway for de novo fatty acid synthesis, i.e. acetyl-CoA carboxylase and fatty acid synthase, were found in lamb-liver cytosol. Both enzyme activities, as well as those of the NADPH-furnishing enzymes, were significantly reduced by SO feeding. In contrast, microsomal and especially mitochondrial fatty acid chain elongation activity, the latter being much higher than that of rat liver, were significantly increased in SO-treated lambs. In these animals, a stimulation of triangle up(9)-desaturase activity was observed in liver microsomes. PMID:17466555

Caputi Jambrenghi, A; Paglialonga, G; Gnoni, A; Zanotti, F; Giannico, F; Vonghia, G; Gnoni, G V

2007-07-01

80

Omega-3 fatty acid oxidation products prevent vascular endothelial cell activation by coplanar polychlorinated biphenyls  

SciTech Connect

Coplanar polychlorinated biphenyls (PCBs) may facilitate development of atherosclerosis by stimulating pro-inflammatory pathways in the vascular endothelium. Nutrition, including fish oil-derived long-chain omega-3 fatty acids, such as docosahexaenoic acid (DHA, 22:6{omega}-3), can reduce inflammation and thus the risk of atherosclerosis. We tested the hypothesis that cyclopentenone metabolites produced by oxidation of DHA can protect against PCB-induced endothelial cell dysfunction. Oxidized DHA (oxDHA) was prepared by incubation of the fatty acid with the free radical generator 2,2-azo-bis(2-amidinopropane) dihydrochloride (AAPH). Cellular pretreatment with oxDHA prevented production of superoxide induced by PCB77, and subsequent activation of nuclear factor-{kappa}B (NF-{kappa}B). A{sub 4}/J{sub 4}-neuroprostanes (NPs) were identified and quantitated using HPLC ESI tandem mass spectrometry. Levels of these NPs were markedly increased after DHA oxidation with AAPH. The protective actions of oxDHA were reversed by treatment with sodium borohydride (NaBH{sub 4}), which concurrently abrogated A{sub 4}/J{sub 4}-NP formation. Up-regulation of monocyte chemoattractant protein-1 (MCP-1) by PCB77 was markedly reduced by oxDHA, but not by un-oxidized DHA. These protective effects were proportional to the abundance of A{sub 4}/J{sub 4} NPs in the oxidized DHA sample. Treatment of cells with oxidized eicosapentaenoic acid (EPA, 20:5{omega}-3) also reduced MCP-1 expression, but less than oxDHA. Treatment with DHA-derived cyclopentenones also increased DNA binding of NF-E2-related factor-2 (Nrf2) and downstream expression of NAD(P)H:quinone oxidoreductase (NQO1), similarly to the Nrf-2 activator sulforaphane. Furthermore, sulforaphane prevented PCB77-induced MCP-1 expression, suggesting that activation of Nrf-2 mediates the observed protection against PCB77 toxicity. Our data implicate A{sub 4}/J{sub 4}-NPs as mediators of omega-3 fatty acid-mediated protection against the endothelial toxicity of coplanar PCBs.

Majkova, Zuzana [Graduate Center for Toxicology, University of Kentucky, Lexington, KY 40536-0200 (United States); Layne, Joseph [Graduate Center for Nutritional Sciences, University of Kentucky, Lexington, KY 40536-0200 (United States); Sunkara, Manjula; Morris, Andrew J. [Division of Cardiovascular Medicine, The Gill Heart Institute, University of Kentucky, Lexington, KY 40536-0509 (United States); Toborek, Michal [Department of Neurosurgery, University of Kentucky, Lexington, KY 40536-0200 (United States); Hennig, Bernhard, E-mail: bhennig@email.uky.edu [Graduate Center for Toxicology, University of Kentucky, Lexington, KY 40536-0200 (United States); Graduate Center for Nutritional Sciences, University of Kentucky, Lexington, KY 40536-0200 (United States); Department of Animal and Food Sciences, University of Kentucky, Lexington, KY 40536-0200 (United States)

2011-02-15

81

Continuous volatile fatty acid production from waste activated sludge hydrolyzed at pH 12.  

PubMed

This study adopted rapid alkaline treatment at pH 12 to hydrolyze 66% of total chemical oxygen demands. Then the hydrolyzed liquor was fermented in a continuous-flow stirred reactor to produce volatile fatty acids (VFAs) at 8-h hydraulic retention time and at 35 °C. The maximum VFA productivity reached 365 mg VFAs g(-1) volatile suspended solids in a 45-d operation, with most produced VFAs being acetate and propionate, principally produced by protein degradation. The Bacteroidia, ?-proteobacteria and the Clostridia were identified to be the classes correlating with the fermentation processes. The fermented liquor was applied to denitrifying phosphorus removal process as alternative carbon source after excess phosphorus and nitrogen being recycled via struvite precipitation. Fermented liquors from alkaline hydrolysis-acid fermentation on waste activated sludge are a potential renewable resource for applications that need organic carbons. PMID:24630368

Yang, Xue; Wan, Chunli; Lee, Duu-Jong; Du, Maoan; Pan, Xiangliang; Wan, Fang

2014-09-01

82

Epoxide hydrolase activities and epoxy fatty acids in the mosquito Culex quinquefasciatus.  

PubMed

Culex mosquitoes have emerged as important model organisms for mosquito biology, and are disease vectors for multiple mosquito-borne pathogens, including West Nile virus. We characterized epoxide hydrolase activities in the mosquito Culex quinquefasciatus, which suggested multiple forms of epoxide hydrolases were present. We found EH activities on epoxy eicosatrienoic acids (EETs). EETs and other eicosanoids are well-established lipid signaling molecules in vertebrates. We showed EETs can be synthesized in vitro from arachidonic acids by mosquito lysate, and EETs were also detected in vivo both in larvae and adult mosquitoes by LC-MS/MS. The EH activities on EETs can be induced by blood feeding, and the highest activity was observed in the midgut of female mosquitoes. The enzyme activities on EETs can be inhibited by urea-based inhibitors designed for mammalian soluble epoxide hydrolases (sEH). The sEH inhibitors have been shown to play diverse biological roles in mammalian systems, and they can be useful tools to study the function of EETs in mosquitoes. Besides juvenile hormone metabolism and detoxification, insect epoxide hydrolases may also play a role in regulating lipid signaling molecules, such as EETs and other epoxy fatty acids, synthesized in vivo or obtained from blood feeding by female mosquitoes. PMID:25686802

Xu, Jiawen; Morisseau, Christophe; Yang, Jun; Mamatha, Dadala M; Hammock, Bruce D

2015-04-01

83

Ozonolysis products of membrane fatty acids activate eicosanoid metabolism in human airway epithelial cells  

SciTech Connect

When inhaled, ozone reacts at the airway luminal surface with unsaturated fatty acids contained in the extracellular fluid and plasma membrane to form an aldehyde and hydroxyhydroperoxide. The resulting hydroxyhydroperoxide degrades in aqueous systems to yield a second aldehyde and hydrogen peroxide (H2O2). Previously, we demonstrated that ozone can augment eicosanoid metabolism in bovine airway epithelial cells. To examine structure-activity relationships of ozone-fatty acid degradation products on eicosanoid metabolism in human airway epithelial cells, 3-, 6-, and 9-carbon saturated aldehydes and hydroxyhydroperoxides were synthesized and purified. Eicosanoid metabolism was evaluated by determination of total 3H-activity release from confluent cells previously incubated with [3H]arachidonic acid and by identification of specific metabolites with high performance liquid chromatography and radioimmunoassay. The major metabolites detected were prostaglandin E2, prostaglandin F2 alpha, and 15-hydroxyeicosatetraenoic acid. The 9-carbon aldehyde, nonanal, in contrast to 3- or 6-carbon aldehydes, stimulated release at concentrations > or = 100 microM, suggesting that the stimulatory effect increases with increasing chain length. When tested under identical conditions, the 3-, 6-, and 9-carbon hydroxyhydroperoxides were more potent than the corresponding aldehydes. Again, a greater effect was noted when the chain length was increased. One possible explanation for the increased potency of the hydroxyhydroperoxides over the aldehydes could be due to degradation of the hydroxyhydroperoxide into H2O2 and aldehyde. We consider this an unlikely explanation because responses varied with chain length (although each hydroxyhydroperoxide would produce an equivalent amount of H2O2) and because exposure to H2O2 alone or H2O2 plus hexanal produced a response dissimilar to 1-hydroxy-1-hexanehydroperoxide.

Leikauf, G.D.; Zhao, Q.; Zhou, S.; Santrock, J. (Univ. of Cincinnati Medical Center, OH (United States))

1993-12-01

84

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

85

The glucose dependence of Akt-transformed cells can be reversed by pharmacologic activation of fatty acid beta-oxidation.  

PubMed

Activation of the oncogenic kinase Akt stimulates glucose uptake and metabolism in cancer cells and renders these cells susceptible to death in response to glucose withdrawal. Here we show that 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR) reverses the sensitivity of Akt-expressing glioblastoma cells to glucose deprivation. AICAR's protection depends on the activation of AMPK, as expression of a dominant-negative form of AMPK abolished this effect. AMPK is a cellular energy sensor whose activation can both block anabolic pathways such as protein synthesis and activate catabolic reactions such as fatty acid oxidation to maintain cellular bioenergetics. While rapamycin treatment mimicked the effect of AICAR on inhibiting markers of cap-dependent translation, it failed to protect Akt-expressing cells from death upon glucose withdrawal. Compared to control cells, Akt-expressing cells were impaired in the ability to induce fatty acid oxidation in response to glucose deprivation unless stimulated with AICAR. Stimulation of fatty acid oxidation was sufficient to maintain cell survival as activation of fatty acid oxidation with bezafibrate also protected Akt-expressing cells from glucose withdrawal-induced death. Conversely, treatment with a CPT-1 inhibitor to block fatty acid import into mitochondria prevented AICAR from stimulating fatty acid oxidation and promoting cell survival in the absence of glucose. Finally, cell survival did not require reversal of Akt's effects on either protein translation or lipid synthesis as the addition of the cell penetrant oxidizable substrate methyl-pyruvate was sufficient to maintain survival of Akt-expressing cells deprived of glucose. Together, these data suggest that activation of Akt blocks the ability of cancer cells to metabolize nonglycolytic bioenergetic substrates, leading to glucose addiction. PMID:15806154

Buzzai, Monica; Bauer, Daniel E; Jones, Russell G; Deberardinis, Ralph J; Hatzivassiliou, Georgia; Elstrom, Rebecca L; Thompson, Craig B

2005-06-16

86

Mangiferin Decreases Plasma Free Fatty Acids through Promoting Its Catabolism in Liver by Activation of AMPK  

PubMed Central

Mangiferin has been shown to have the effect of improving dyslipidemia. Plasma free fatty acids (FFA) are closely associated with blood lipid metabolism as well as many diseases including metabolic syndrome. This study is to investigate whether mangiferin has effects on FFA metabolism in hyperlipidemic rats. Wistar rats were fed a high-fat diet and administered mangiferin simultaneously for 6 weeks. Mangiferin (50, 100, 150 mg/kg BW) decreased dose-dependently FFA and triglycerides (TG) levels in plasma, and their accumulations in liver, but increased the ?-hydroxybutyrate levels in both plasma and liver of hyperlipidemic rats. HepG2 cells were treated with oleic acid (OA, 0.2 mmol/L) to simulate the condition of high level of plasma FFA in vitro, and were treated with different concentrations of mangiferin simultaneously for 24 h. We found that mangiferin significantly increased FFA uptake, significantly decreased intracellular FFA and TG accumulations in HepG2 cells. Mangiferin significantly increased AMP-activated protein kinase (AMPK) phosphorylation and its downstream proteins involved in fatty acid translocase (CD36) and carnitine palmitoyltransferase 1 (CPT1), but significantly decreased acyl-CoA: diacylgycerol acyltransferase 2 (DGAT2) expression and acetyl-CoA carboxylase (ACC) activity by increasing its phosphorylation level in both in vivo and in vitro studies. Furthermore, these effects were reversed by Compound C, an AMPK inhibitor in HepG2 cells. For upstream of AMPK, mangiferin increased AMP/ATP ratio, but had no effect on LKB1 phosphorylation. In conclusion, mangiferin decreased plasma FFA levels through promoting FFA uptake and oxidation, inhibiting FFA and TG accumulations by regulating the key enzymes expression in liver through AMPK pathway. Therefore, mangiferin is a possible beneficial natural compound for metabolic syndrome by improving FFA metabolism. PMID:22292039

Niu, Yucun; Li, Songtao; Na, Lixin; Feng, Rennan; Liu, Liyan; Li, Ying; Sun, Changhao

2012-01-01

87

CTRP5 ameliorates palmitate-induced apoptosis and insulin resistance through activation of AMPK and fatty acid oxidation.  

PubMed

Lipotoxicity resulting from a high concentration of saturated fatty acids is closely linked to development of insulin resistance, as well as apoptosis in skeletal muscle. CTRP5, an adiponectin paralog, is known to activate AMPK and fatty acid oxidation; however, the effects of CTRP5 on palmitate-induced lipotoxicity in myocytes have not been investigated. We found that globular domain of CTRP5 (gCTRP5) prevented palmitate-induced apoptosis and insulin resistance in myocytes by inhibiting the activation of caspase-3, reactive oxygen species accumulation, and IRS-1 reduction. These beneficial effects of gCTRP5 are mainly attributed to an increase in fatty acid oxidation through phosphorylation of AMPK. These results provide a novel function of CTRP5, which may have preventive and therapeutic potential in management of obesity, insulin resistance, and type 2 diabetes mellitus. PMID:25195818

Yang, Won-Mo; Lee, Wan

2014-09-26

88

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

PubMed Central

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

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

2014-01-01

89

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

90

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

91

Modulation of peroxisome proliferator-activated receptor gamma (PPAR ?) by conjugated fatty acid in obesity and inflammatory bowel disease.  

PubMed

Conjugated fatty acids including conjugated linoleic acid (CLA) and conjugated linolenic acid (CLNA) have drawn significant attention for their variety of biologically beneficial effects. Evidence suggested that CLA and CLNA could play physiological roles by regulating the expression and activity of PPAR ?. This review summarizes the current understanding of evidence of the role of CLA (cis-9,trans-11 CLA and trans-10,cis-12 CLA) and CLNA (punicic acid and ?-eleostearic acid) in modulating the expression or activity of PPAR ? that could in turn be employed as complementary treatment for obesity and inflammatory bowel disease. PMID:25634802

Yuan, Gaofeng; Chen, Xiaoe; Li, Duo

2015-02-25

92

Synthesis of Phenoxyacyl-Ethanolamides and Their Effects on Fatty Acid Amide Hydrolase Activity*  

PubMed Central

N-Acylethanolamines (NAEs) are involved in numerous biological activities in plant and animal systems. The metabolism of these lipids by fatty acid amide hydrolase (FAAH) is a key regulatory point in NAE signaling activity. Several active site-directed inhibitors of FAAH have been identified, but few compounds have been described that enhance FAAH activity. Here we synthesized two sets of phenoxyacyl-ethanolamides from natural products, 3-n-pentadecylphenolethanolamide and cardanolethanolamide, with structural similarity to NAEs and characterized their effects on the hydrolytic activity of FAAH. Both compounds increased the apparent Vmax of recombinant FAAH proteins from both plant (Arabidopsis) and mammalian (Rattus) sources. These NAE-like compounds appeared to act by reducing the negative feedback regulation of FAAH activity by free ethanolamine. Both compounds added to seedlings relieved, in part, the negative growth effects of exogenous NAE12:0. Cardanolethanolamide reduced neuronal viability and exacerbated oxidative stress-mediated cell death in primary cultured neurons at nanomolar concentrations. This was reversed by FAAH inhibitors or exogenous NAE substrate. Collectively, our data suggest that these phenoxyacyl-ethanolamides act to enhance the activity of FAAH and may stimulate the turnover of NAEs in vivo. Hence, these compounds might be useful pharmacological tools for manipulating FAAH-mediated regulation of NAE signaling in plants or animals. PMID:24558037

Faure, Lionel; Nagarajan, Subbiah; Hwang, Hyeondo; Montgomery, Christa L.; Khan, Bibi Rafeiza; John, George; Koulen, Peter; Blancaflor, Elison B.; Chapman, Kent D.

2014-01-01

93

Aqueous Ozonation Of Fatty Acids  

Microsoft Academic Search

The reactivity of a series of fatty acids toward ozone was examined in aqueous solution at low substrate concentration (?g.L range). Saturated fatty acids were unreactive, unsaturated fatty acids were readily consumed. A number of reaction products or their methylated derivatives were identified by gas chromatography and gas chromatography-mass spectrometry. The products identified are consistent with a 1,3-dipolar cyclo-addotion reaction.

G. Reynolds; C. Corless; N. Graham; R. Perry; T. M. Gibson; J. Haley

1989-01-01

94

Omega-3 free fatty acids suppress macrophage inflammasome activation by inhibiting NF-?B activation and enhancing autophagy.  

PubMed

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

95

Inhibition of fatty acid metabolism ameliorates disease activity in an animal model of multiple sclerosis.  

PubMed

Multiple sclerosis is an inflammatory demyelinating disease of the central nervous system and a leading cause of neurological disability. The complex immunopathology and variable disease course of multiple sclerosis have limited effective treatment of all patients. Altering the metabolism of immune cells may be an attractive strategy to modify their function during autoimmunity. We examined the effect of inhibiting fatty acid metabolism in experimental autoimmune encephalomyelitis (EAE), a mouse model of multiple sclerosis. Mice treated with an inhibitor of carnitine palmitoyltransferase 1 (CPT-1), the rate-limiting enzyme in the beta-oxidation of fatty acids, showed a reduction in disease severity as well as less inflammation and demyelination. Inhibition of CPT-1 in encephalitogenic T-cells resulted in increased apoptosis and reduced inflammatory cytokine production. These results suggest that disruption of fatty acid metabolism promotes downregulation of inflammation in the CNS and that this metabolic pathway is a potential therapeutic target for multiple sclerosis. PMID:22355598

Shriver, Leah P; Manchester, Marianne

2011-01-01

96

Inhibiting bacterial fatty acid synthesis.  

PubMed

The type II fatty acid synthase consists of a series of individual enzymes, each encoded by a separate gene, that catalyze discrete steps in chain elongation. The formation of fatty acids is vital to bacteria, and each of the essential enzymes and their acyl group carriers represent a potential target for the development of novel antibacterial therapeutics. High resolution x-ray and/or NMR structures of representative members of every enzyme in the type II pathway are now available, and these structures are a valuable resource to guide antibacterial drug discovery. The role of each enzyme in regulating pathway activity and the diversity in the components of the pathway in the major human pathogens are important considerations in deciding the most suitable targets for future drug development. PMID:16648134

Zhang, Yong-Mei; White, Stephen W; Rock, Charles O

2006-06-30

97

Antibacterial Activity of Long-Chain Polyunsaturated Fatty Acids against Propionibacterium acnes and Staphylococcus aureus  

PubMed Central

New compounds are needed to treat acne and superficial infections caused by Propionibacterium acnes and Staphylococcus aureus due to the reduced effectiveness of agents used at present. Long-chain polyunsaturated fatty acids (LC-PUFAs) are attracting attention as potential new topical treatments for Gram-positive infections due to their antimicrobial potency and anti-inflammatory properties. This present study aimed to investigate the antimicrobial effects of six LC-PUFAs against P. acnes and S. aureus to evaluate their potential to treat infections caused by these pathogens. Minimum inhibitory concentrations were determined against P. acnes and S. aureus, and the LC-PUFAs were found to inhibit bacterial growth at 32–1024 mg/L. Generally, P. acnes was more susceptible to the growth inhibitory actions of LC-PUFAs, but these compounds were bactericidal only for S. aureus. This is the first report of antibacterial activity attributed to 15-hydroxyeicosapentaenoic acid (15-OHEPA) and 15-hydroxyeicosatrienoic acid (HETrE), while the anti-P. acnes effects of the six LC-PUFAs used herein are novel observations. During exposure to the LC-PUFAs, S. aureus cells were killed within 15–30 min. Checkerboard assays demonstrated that the LC-PUFAs did not antagonise the antimicrobial potency of clinical agents used presently against P. acnes and S. aureus. However, importantly, synergistic interactions against S. aureus were detected for combinations of benzoyl peroxide with 15-OHEPA, dihomo-?-linolenic acid (DGLA) and HETrE; and neomycin with 15-OHEPA, DGLA, eicosapentaenoic acid, ?-linolenic acid and HETrE. In conclusion, LC-PUFAs warrant further evaluation as possible new agents to treat skin infections caused by P. acnes and S. aureus, especially in synergistic combinations with antimicrobial agents already used clinically. PMID:24232668

Desbois, Andrew P.; Lawlor, Keelan C.

2013-01-01

98

Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus.  

PubMed

New compounds are needed to treat acne and superficial infections caused by Propionibacterium acnes and Staphylococcus aureus due to the reduced effectiveness of agents used at present. Long-chain polyunsaturated fatty acids (LC-PUFAs) are attracting attention as potential new topical treatments for Gram-positive infections due to their antimicrobial potency and anti-inflammatory properties. This present study aimed to investigate the antimicrobial effects of six LC-PUFAs against P. acnes and S. aureus to evaluate their potential to treat infections caused by these pathogens. Minimum inhibitory concentrations were determined against P. acnes and S. aureus, and the LC-PUFAs were found to inhibit bacterial growth at 32-1024 mg/L. Generally, P. acnes was more susceptible to the growth inhibitory actions of LC-PUFAs, but these compounds were bactericidal only for S. aureus. This is the first report of antibacterial activity attributed to 15-hydroxyeicosapentaenoic acid (15-OHEPA) and 15-hydroxyeicosatrienoic acid (HETrE), while the anti-P. acnes effects of the six LC-PUFAs used herein are novel observations. During exposure to the LC-PUFAs, S. aureus cells were killed within 15-30 min. Checkerboard assays demonstrated that the LC-PUFAs did not antagonise the antimicrobial potency of clinical agents used presently against P. acnes and S. aureus. However, importantly, synergistic interactions against S. aureus were detected for combinations of benzoyl peroxide with 15-OHEPA, dihomo-?-linolenic acid (DGLA) and HETrE; and neomycin with 15-OHEPA, DGLA, eicosapentaenoic acid, ?-linolenic acid and HETrE. In conclusion, LC-PUFAs warrant further evaluation as possible new agents to treat skin infections caused by P. acnes and S. aureus, especially in synergistic combinations with antimicrobial agents already used clinically. PMID:24232668

Desbois, Andrew P; Lawlor, Keelan C

2013-11-01

99

Fatty acid oxidation in brain is limited by the low activity of 3-ketoacyl-CoA thiolase  

SciTech Connect

In an attempt to establish why the brain is virtually incapable of oxidizing fatty acids, the activities of the ..beta..-oxidation enzymes in rat brain and rat heart mitochondria were measured and compared with each other. Although the apparent K/sub m/ values and chain-length specificities of the brain and heart enzymes are similar, the specific activities of all but one brain enzyme are between 4% and 50% of those observed in heart mitochondria. The exception is 3-ketoacyl-CoA thiolase (EC 2.3.1.16) whose specific activity in brain mitochondria is 125-times lower than in heart mitochondria. The partially purified brain 3-ketoacyl-CoA thiolase was shown to be catalytically and immunologically identical with the heart enzyme. The low rate of fatty acid oxidation in brain mitochondria estimated on the basis of palmitoylcarnitine-supported respiration and (1-/sup 14/C)palmitoylcarnitine degradation may be the consequence of the low activity of 3-ketoacyl-CoA thiolase. Inhibition of (1-/sup 14/C)palmitoylcarnitine oxidation by 4-bromocrotonic acid proves that the observed oxidation of fatty acids in brain is dependent on 3-ketoacyl-CoA thiolase and thus occurs via ..beta..-oxidation. Since the reactions catalyzed by carnitine palmitoyltransferase (EC 2.3.1.21) and acyl-CoA synthetase (EC 6.2.1.3) do not seem to restrict fatty acid oxidation in brain, it is concluded that the oxidation of fatty acids in rat brain is limited by the activity of the mitochondrial 3-ketoacyl-CoA thiolase.

Yang, S.; He, X.; Schulz, H.

1987-05-01

100

Ligand determinants of fatty acid activation of the pronociceptive ion channel TRPA1  

PubMed Central

Background and purpose. Arachidonic acid (AA) and its derivatives are important modulators of cellular signalling. The transient receptor potential cation channel subfamily A, member 1 (TRPA1) is a cation channel with important functions in mediating cellular responses to noxious stimuli and inflammation. There is limited information about the interactions between AA itself and TRPA1, so we investigated the effects of AA and key ethanolamide and amino acid/neurotransmitter derivatives of AA on hTRPA1. Experimental approach. HEK 293 cells expressing hTRPA1 were studied by measuring changes in intracellular calcium ([Ca]i) with a fluorescent dye and by standard whole cell patch clamp recordings. Key results. AA (30 ?M) increased fluorescence in hTRPA1 expressing cells by 370% (notional EC50 13 ?M). The covalent TRPA1 agonist cinnamaldehyde (300 ?M) increased fluorescence by 430% (EC50, 11 ?M). Anandamide (230%) and N-arachidonoyl tyrosine (170%) substantially activated hTRPA1 at 30 ?M, however, N-arachidonoyl conjugates of glycine and taurine were less effective while N-acyl conjugates of 5-HT did not affect hTRPA1. Changing the acyl chain length or the number and position of double bonds reduced fatty acid efficacy at hTRPA1. Mutant hTRPA1 (Cys621, Cys641 and Cys665 changed to Ser) could be activated by AA (100 ?M, 40% of wild type) but not by cinnamaldehyde (300 ?M). Conclusions and implications. AA is a more potent activator of TRPA1 than its ethanolamide or amino acid/neurotransmitter derivatives and acts via a mechanism distinct from that of cinnamaldehyde, further underscoring the likelyhood of multiple pharmacologically exploitable sites on hTRPA1. PMID:24516781

Gu, Liuqiong; Camo, Maxime; McIntyre, Peter; Connor, Mark

2014-01-01

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

Antioomycete activity of gamma-oxocrotonate fatty acids against P. infestans.  

PubMed

Infections with Phytophthora infestans, the causal agent of potato and tomato late blight disease, are difficult to control and can lead to considerable agricultural losses. Thus, the development of new effective agents against the pathogen is of great interest. In previous work, (E)-4-oxohexadec-2-enoic acid (3) was isolated from Hygrophorus eburneus, which exhibited fungicidal activity against Cladosporium cucumerinum. Here, the inhibitory effect of 3 on P. infestans spore germination and mycelium growth in vitro is demonstrated. The in vivo effect on infections of whole potato plants was investigated by spraying plants with the sodium salt of 3, sodium (2E)-4-oxohexadec-2-enoic acid (4), prior to P. infestans inoculation. Additionally, the influence of 3 on mycelium growth of Colletotrichum coccodes, the causal agent of potato black dot disease, was analyzed. In all approaches, a significant inhibition of pathogen development was achieved. Importantly, the unsaturated fatty acid exerted no toxic effect when sprayed on plants, a prerequisite for its commercial use. PMID:19778058

Eschen-Lippold, Lennart; Draeger, Tobias; Teichert, Axel; Wessjohann, Ludger; Westermann, Bernhard; Rosahl, Sabine; Arnold, Norbert

2009-10-28

103

Fatty acid-producing hosts  

DOEpatents

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

Pfleger, Brian F; Lennen, Rebecca M

2013-12-31

104

Purification and characterization of a fatty acid-activated protein kinase (PKN) from rat testis.  

PubMed

PKN, a novel protein kinase with a catalytic domain homologous to that of the protein kinase C (PKC) family and unique N-terminal leucine-zipper-like sequences, was identified by molecular cloning from a human hippocampus cDNA library [Mukai and Ono (1994) Biochem. Biophys. Res. Commun. 199, 897-904]. Recently we partially purified recombinant PKN from COS7 cells transfected with the cDNA construct encoding human PKN, and demonstrated that the recombinant PKN was activated by unsaturated fatty acids and limited proteolysis [Mukai, Kitagawa, Shibata et al. (1994) Biochem. Biophys. Res. Commun. 204, 348-356]. The present work has focused on the further purification and characterization of PKN from native rat tissue. Immunochemical measurement revealed that PKN was found in every tissue, and was especially abundant in testis, spleen and brain; subcellular fractionation of rat brain showed that half of the PKN was localized in the soluble cytosolic fraction. PKN was purified approx. 8000-fold to apparent homogeneity from the cytosolic fraction of rat testis by DEAE-cellulose chromatography, ammonium sulphate fractionation and chromatography on butyl-Sepharose, heparin-Sepharose, Mono Q and protamine-CH-Sepharose. The enzyme migrates as a band of apparent molecular mass 120 kDa. Using serine-containing peptides based on the pseudosubstrate sequence of PKC-delta as phosphate acceptors, the kinase activity was stimulated several-fold by 40 microM unsaturated fatty acids or by detergents such as 0.04% sodium deoxycholate and 0.004% SDS. In the absence of modifiers, protamine sulphate, myelin basic protein and synthetic peptides based on the pseudosubstrate site of PKCs or ribosomal S6 protein were good substrates for phosphorylation by the kinase. In the presence of 40 microM arachidonic acid the kinase activity of PKN for these phosphate acceptors was increased 2-18-fold. The autophosphorylation activity of purified PKN was partially inhibited by pretreatment with alkaline phosphatase. These properties appear to distinguish PKN from many protein kinases isolated previously. PMID:7654208

Kitagawa, M; Mukai, H; Shibata, H; Ono, Y

1995-09-01

105

Ligand-Activated PPAR?-Dependent DNA Demethylation Regulates the Fatty Acid ?-Oxidation Genes in the Postnatal Liver.  

PubMed

The metabolic function of the liver changes sequentially during early life in mammals to adapt to the marked changes in nutritional environment. Accordingly, hepatic fatty acid ?-oxidation is activated after birth to produce energy from breast milk lipids. However, how it is induced during the neonatal period is poorly understood. Here we show DNA demethylation and increased mRNA expression of the fatty acid ?-oxidation genes in the postnatal mouse liver. The DNA demethylation does not occur in the fetal mouse liver under the physiologic condition, suggesting that it is specific to the neonatal period. Analysis of mice deficient in the nuclear receptor peroxisome proliferator-activated receptor ? (PPAR?) and maternal administration of a PPAR? ligand during the gestation and lactation periods reveal that the DNA demethylation is PPAR? dependent. We also find that DNA methylation of the fatty acid ?-oxidation genes are reduced in the adult human liver relative to the fetal liver. This study represents the first demonstration that the ligand-activated PPAR?-dependent DNA demethylation regulates the hepatic fatty acid ?-oxidation genes during the neonatal period, thereby highlighting the role of a lipid-sensing nuclear receptor in the gene- and life-stage-specific DNA demethylation of a particular metabolic pathway. PMID:25311726

Ehara, Tatsuya; Kamei, Yasutomi; Yuan, Xunmei; Takahashi, Mayumi; Kanai, Sayaka; Tamura, Erina; Tsujimoto, Kazutaka; Tamiya, Takashi; Nakagawa, Yoshimi; Shimano, Hitoshi; Takai-Igarashi, Takako; Hatada, Izuho; Suganami, Takayoshi; Hashimoto, Koshi; Ogawa, Yoshihiro

2015-03-01

106

Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme A synthetase activity in Caco-2 cells.  

PubMed

Red pepper and its major pungent component, capsaicin, have been associated with hypolipidemic effects in rats, although mechanistic studies on the effects of capsaicin and/or structurally related compounds on lipid metabolism are scarce. In this work, the effects of capsaicin and its structural analog nonivamide, the aliphatic alkamide trans-pellitorine and vanillin as the basic structural element of all vanilloids on the mechanisms of intestinal fatty acid uptake in differentiated intestinal Caco-2 cells were studied. Capsaicin and nonivamide were found to reduce fatty acid uptake, with IC50 values of 0.49 ?M and 1.08 ?M, respectively. trans-Pellitorine was shown to reduce fatty acid uptake by 14.0±2.14% at 100 ?M, whereas vanillin was not effective, indicating a pivotal role of the alkyl chain with the acid amide group in fatty acid uptake by Caco-2 cells. This effect was associated neither with the activation of the transient receptor potential cation channel subfamily V member 1 (TRPV1) or the epithelial sodium channel (ENaC) nor with effects on paracellular transport or glucose uptake. However, acetyl-coenzyme A synthetase activity increased (p<0.05) in the presence of 10 ?M capsaicin, nonivamide or trans-pellitorine, pointing to an increased fatty acid biosynthesis that might counteract the decreased fatty acid uptake. PMID:25422952

Rohm, Barbara; Riedel, Annett; Ley, Jakob P; Widder, Sabine; Krammer, Gerhard E; Somoza, Veronika

2015-01-01

107

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

108

[Effects of different tillage methods on phospholipid fatty acids and enzyme activities in calcareous cinnamon soil].  

PubMed

In order to study changes of physical and chemical characteristics and microbial activities in soil under different tillage methods, effects of four tillage methods, rotary tillage (RT), subsoil tillage (ST), conventional tillage (CT) with corn straw returned to soil, and rotary tillage with no corn straw returned to soil (CK), on phospholipid fatty acids (PLFA) characteristics and hydrolase enzymes activities in calcareous cinnamon soil were investigated. The results showed that soil hydrolase enzymes activities, nutrient contents, microbial diversity varied greatly with the different tillage methods. Returning corn straw to soil increased the kinds, amount of soil total PLFAs, bacteria PLFAs and actonomycetes PLFAs, while decreased the fungi PLFAs, indicating that fungi was more adaptable than bacteria to an infertile environment. ST and CT resulted in higher amounts of total PLFAs, which were 74.7% and 53.3% higher than that of CK, indicating they were more beneficial to the growth of plants. They could also improve soil physical and chemical properties, increase alk-phosphatase, protease and urease activities, which would provide a favorable soil condition for high and stable crop yields. PMID:25509078

Pei, Xue-Xia; Dang, Jian-You; Zhang, Ding-Yi; Wang, Jiao-Ai; Zhang, Jing

2014-08-01

109

Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities.  

PubMed

Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably. PMID:21515060

Zhao, Wei; Sun, Jie; Xiang, Hua; Zeng, Yan-yan; Li, Xiao-bo; Xiao, Hong; Chen, De-ying; Ma, Ren-ling

2011-05-15

110

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

E-print Network

; TLC, thin layer chromatography § This is National Research Council of Canada publication number NRCC transformants. Lines with the highest hydroxy fatty acid content showed significant reduction in total oil the catalytic outcome of the hydroxylation/desaturation reaction. Transformation of an Arabidopsis fad2/fae1

Kunst, Ljerka

111

enzyme activities in muscle (experiment 1). This suggests that the fatty acids deposited  

E-print Network

that such a regulatory system is involved in the modulation of fatty acid utilisation in pig skeletal muscle during early by age, cold exposure and muscle type in piglet skeletal muscle. I. Schmidt, M. Damon, P. Herpinstation increased rapidly after birth in piglet skeletal muscle. During cold stress, the muscle-specific decrease

Paris-Sud XI, Université de

112

Antioxidant Enzyme Activities and Mitochondrial Fatty Acids in Pulmonary Hypertension Syndrome (PHS) in Broilers1  

Microsoft Academic Search

Major objectives of this study were to as- sess antioxidant protection and fatty acid profile in lung mitochondria and whole liver in broilers with pulmonary hypertension syndrome ((PHS; with and without high dietary vitamin E (VE)) (Experiment 1) and in broilers that did not develop PHS but were genetically selected (S) or not selected (NS) for resistance to PHS (Experiment

M. Iqbal; D. Cawthon; K. Beers; R. F. Wideman; W. G. Bottje

113

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

114

Effects of 3-thia fatty acids on feed intake, growth, tissue fatty acid composition, ?-oxidation and Na +,K +ATPase activity in Atlantic salmon  

Microsoft Academic Search

Atlantic salmon (Salmo salar) with an initial mass of 86 g were reared in 12 °C seawater for 8 weeks to a final average mass of 250 g. The fish were fed fish meal and fish oil-based diet supplemented with either 0%, 0.3% or 0.6% of tetradecylthioacetic acid (TTA), a 3-thia fatty acid. The specific growth rate (SGR) decreased with

Corina Moya-Falcón; Erlend Hvattum; Endre Dyrøy; Jon Skorve; Sigurd O. Stefansson; Magny S. Thomassen; Jan V. Jakobsen; Rolf K. Berge; Bente Ruyter

2004-01-01

115

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

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

Antioxidant activity of Haematococcus pluvialis cells grown in continuous culture as a function of their carotenoid and fatty acid content  

Microsoft Academic Search

The influence of culture conditions on the quality of Haematococcus pluvialis biomass is assessed. Continuously grown cells have been characterised with respect to their astaxanthin, fatty acid content,\\u000a and antioxidant activity and compared with those of non-growing haematocysts. Moderate limitation of nitrate availability\\u000a (1.7 mM) under continuous growth conditions favoured the production of reddish palmelloid cells whose extracts possessed antioxidant\\u000a activity

M. C. Cerón; M. C. García-Malea; J. Rivas; F. G. Acien; J. M. Fernandez; E. Del Río; M. G. Guerrero; E. Molina

2007-01-01

118

N-3 Fatty Acids Inhibit Vascular Calcification Via the p38-Mitogen-Activated Protein Kinase and Peroxisome Proliferator-Activated Receptor  Pathways  

Microsoft Academic Search

Fish oil supplementation is associated with lower risk of coronary artery disease in humans, and it has been shown to reduce ectopic calcification in an animal model. How- ever, whether N-3 fatty acids, active ingredients of fish oil, have direct effects on calcification of vascular cells is not clear. In this report, we investigated the effects of eicosa- pentaenoic acid

M. Abedin; J. Lim; T. B. Tang; L. L. Demer; Y. Tintut

2006-01-01

119

Omega-3 polyunsaturated fatty acids.  

PubMed

Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are naturally occurring omega (?)-3 long-chain polyunsaturated fatty acids (PUFAs), which are found in highest quantities in oily fish such as sardines and mackerel. Epidemiological studies of the association between fish intake, ?-3 PUFA intake or blood ?-3 PUFA levels and colorectal cancer (CRC) risk have not consistently suggested beneficial effects of ?-3 PUFAs on CRC (and other gastrointestinal cancer) risk. However, dietary administration of one or both of the main ?-3 PUFAs in rodent models of colorectal carcinogenesis has been demonstrated to reduce colorectal tumour size and multiplicity, compatible with CRC chemopreventative activity. EPA has now been demonstrated to reduce rectal polyp number and size in patients with familial adenomatous polyposis. A randomized polyp prevention trial of EPA is underway in order to test chemopreventative efficacy against 'sporadic' colorectal neoplasia. PMID:22122770

Hull, Mark A

2011-08-01

120

AMP kinase activation with AICAR simultaneously increases fatty acid and glucose oxidation in resting rat soleus muscle  

PubMed Central

5-Amino-4-imidazolecarboxamide riboside (AICAR), a pharmacological activator of AMP-activated protein kinase (AMPK), acutely stimulates glucose uptake and fatty acid (FA) oxidation in skeletal muscle. However, it is not fully understood whether AICAR-induced changes in glucose oxidation are secondary to changes in FA oxidation (i.e. glucose fatty acid cycle), or what role AMPK may be playing in the regulation of intramuscular triacylglycerol (TAG) esterification and hydrolysis. We examined the acute (60 min) effects of AICAR (2 mm) on FA metabolism, glucose oxidation and pyruvate dehydrogenase (PDH) activation in isolated resting rat soleus muscle strips exposed to two different FA concentrations (low fatty acid, LFA, 0.2 mm; high fatty acid, HFA, 1 mm). AICAR significantly increased AMPK ?2 activity (+192%; P < 0.05) over 60 min, and simultaneously increased both FA (LFA: +33%, P < 0.05; HFA: +36%, P < 0.05) and glucose (LFA: +105%, P < 0.05; HFA: +170, P < 0.001) oxidation regardless of FA availability. While there were no changes in TAG esterification, AICAR did increase the ratio of FA partitioned to oxidation relative to TAG esterification (LFA: +15%, P < 0.05; HFA: +49%, P < 0.05). AICAR had no effect on endogenous TAG hydrolysis and oxidation in resting soleus. The stimulation of glucose oxidation with AICAR was associated with an increase in PDH activation (+126%; P < 0.05) but was without effect on pyruvate, an allosteric activator of the PDH complex, suggesting that AMPK may stimulate PDH directly. In conclusion, AMPK appears to be an important regulator of both FA metabolism and glucose oxidation in resting skeletal muscle. PMID:15774530

Smith, Angela C; Bruce, Clinton R; Dyck, David J

2005-01-01

121

Identification and Mechanism of 10-Carbon Fatty Acid as Modulating Ligand of Peroxisome Proliferator-activated Receptors*  

PubMed Central

Peroxisome proliferator-activated receptors (PPAR?, -?/?, and -?) are a subfamily of nuclear receptors that plays key roles in glucose and lipid metabolism. PPAR? is the molecular target of the thiazolidinedione class of antidiabetic drugs that has many side effects. PPAR? is also activated by long chain unsaturated or oxidized/nitrated fatty acids, but its relationship with the medium chain fatty acids remains unclear even though the medium chain triglyceride oils have been used to control weight gain and glycemic index. Here, we show that decanoic acid (DA), a 10-carbon fatty acid and a major component of medium chain triglyceride oils, is a direct ligand of PPAR?. DA binds and partially activates PPAR? without leading to adipogenesis. Crystal structure reveals that DA occupies a novel binding site and only partially stabilizes the AF-2 helix. DA also binds weakly to PPAR? and PPAR?/?. Treatments with DA and its triglyceride form improve glucose sensitivity and lipid profiles without weight gain in diabetic mice. Together, these results suggest that DA is a modulating ligand for PPARs, and the structure can aid in designing better and safer PPAR?-based drugs. PMID:22039047

Malapaka, Raghu R. V.; Khoo, SokKean; Zhang, Jifeng; Choi, Jang H.; Zhou, X. Edward; Xu, Yong; Gong, Yinhan; Li, Jun; Yong, Eu-Leong; Chalmers, Michael J.; Chang, Lin; Resau, James H.; Griffin, Patrick R.; Chen, Y. Eugene; Xu, H. Eric

2012-01-01

122

Identification and Functional Characterization of Genes Encoding Omega-3 Polyunsaturated Fatty Acid Biosynthetic Activities from Unicellular Microalgae  

PubMed Central

In order to identify novel genes encoding enzymes involved in the biosynthesis of nutritionally important omega-3 long chain polyunsaturated fatty acids, a database search was carried out in the genomes of the unicellular photoautotrophic green alga Ostreococcus RCC809 and cold-water diatom Fragilariopsis cylindrus. The search led to the identification of two putative “front-end” desaturases (?6 and ?4) from Ostreococcus RCC809 and one ?6-elongase from F. cylindrus. Heterologous expression of putative open reading frames (ORFs) in yeast revealed that the encoded enzyme activities efficiently convert their respective substrates: 54.1% conversion of ?-linolenic acid for ?6-desaturase, 15.1% conversion of 22:5n-3 for ?4-desaturase and 38.1% conversion of ?-linolenic acid for ?6-elongase. The ?6-desaturase from Ostreococcus RCC809 displays a very strong substrate preference resulting in the predominant synthesis of stearidonic acid (C18:4?6,9,12,15). These data confirm the functional characterization of omega-3 long chain polyunsaturated fatty acid biosynthetic genes from these two species which have until now not been investigated for such activities. The identification of these new genes will also serve to expand the repertoire of activities available for metabolically engineering the omega-3 trait in heterologous hosts as well as providing better insights into the synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in marine microalgae. PMID:24351909

Vaezi, Royah; Napier, Johnathan A.; Sayanova, Olga

2013-01-01

123

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

124

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

125

Cancer cell-associated fatty acid synthase activates endothelial cells and promotes angiogenesis in colorectal cancer.  

PubMed

Upregulation of fatty acid synthase (FASN), a key enzyme of de novo lipogenesis, is associated with metastasis in colorectal cancer (CRC). However, the mechanisms of regulation are unknown. Since angiogenesis is crucial for metastasis, we investigated the role of FASN in the neovascularization of CRC. The effect of FASN on tumor vasculature was studied in orthotopic CRCs, the chick embryo chorioallantoic membrane (CAM) and Matrigel plug models using immunohistochemistry, immunofluorescent staining and confocal microscopy. Cell secretion was evaluated by ELISA and antibody arrays. Proliferation, migration and tubulogenesis of endothelial cells (ECs) were assessed in CRC-EC coculture models. In this study, we found that stable knockdown of FASN decreased microvessel density in HT29 and HCT116 orthotopic CRCs and resulted in 'normalization' of tumor vasculature in both orthotopic and CAM models. Furthermore, FASN regulated secretion of pro- and antiangiogenic factors, including vascular endothelial growth factor-A (VEGF-A). Mechanisms associated with the antiangiogenic activity noted with knockdown of FASN included: downregulation of VEGF(189), upregulation of antiangiogenic isoform VEGF(165b) and a decrease in expression and activity of matrix metalloproteinase-9. Furthermore, conditioned medium from FASN knockdown CRC cells inhibited activation of vascular endothelial growth factor receptor-2 and its downstream signaling and decreased proliferation, migration and tubulogenesis of ECs as compared with control medium. Together, these results suggest that cancer cell-associated FASN regulates tumor vasculature through alteration of the profile of secreted angiogenic factors and regulation of their bioavailability. Inhibition of FASN upstream of VEGF-A and other angiogenic pathways can be a novel therapeutic strategy to prevent or inhibit metastasis in CRC. PMID:24510238

Zaytseva, Yekaterina Y; Elliott, Victoria A; Rychahou, Piotr; Mustain, W Conan; Kim, Ji Tae; Valentino, Joseph; Gao, Tianyan; O'Connor, Kathleen L; Neltner, Janna M; Lee, Eun Y; Weiss, Heidi L; Evers, B Mark

2014-06-01

126

Optimal production of polyhydroxyalkanoates (PHA) in activated sludge fed by volatile fatty acids (VFAs) generated from alkaline excess sludge fermentation  

Microsoft Academic Search

To reduce the production cost of polyhydroxyalkanoates (PHA) and disposal amount of excess sludge simultaneously, the feasibility of using fermentative volatile fatty acids (VFAs) as carbon sources to synthesize PHA by activated sludge was examined. At pH 11.0, 60°C and fermentative time of 7d, the VFAs yield was 258.65mgTOC\\/gVSS. To restrain cell growth during PHA production, the released phosphorus and

Cai Mengmeng; Chua Hong; Zhao Qingliang; Sin Ngai Shirley; Ren Jie

2009-01-01

127

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

128

Microglial cell activation increases saturated and decreases monounsaturated fatty acid content, but both lipid species are proinflammatory.  

PubMed

Neuroinflammation is a component of age-related neurodegenerative diseases and cognitive decline. Saturated (SFA) and monounsaturated (MUFA) fatty acids are bioactive molecules that may play different extrinsic and intrinsic roles in neuroinflammation, serving as exogenous ligands for cellular receptors, or endogenous components of cell structural, energetic and signaling pathways. We determined the fatty acyl profile of BV2 microglial cells before and after acute activation with lipopolysaccharide (LPS). We also investigated the effect of SFA and MUFA pretreatment on the production of an invasive, neurotoxic phenotype in BV2 cells. Acute activation of BV2 microglia resulted in an increase in the relative content of SFA (12:0, 16:0, 18:0, 20:0, 22:0, and 24:0 increased significantly), and a relative decrease in the content of MUFA (16:1n7, 18:1n7, 18:1n9, 20:1n9, 24:1n9 decreased significantly). In agreement, the major stearoyl-CoA desaturase (SCD) isoform in BV2 cells, SCD2, was significantly down-regulated by LPS. We next treated cells with SFA (16:0 or 18:0) or MUFA (16:1n7 or 18:1n9), and found that levels of secreted IL6 were increased, as was secreted MMP9-mediated proteolytic activity. To test the functional significance, we treated SH-SY5Y neuronal cells with conditioned medium from BV2 cells pretreated with fatty acids, and found a small but significant induction of cell death. Our findings suggest differential intrinsic roles for SFA and MUFA in activated microglial cells, but similar extrinsic roles for these fatty acid species in inducing activation. Expansion of SFA is important during microglial cell activation, but either supplemental SFA or MUFA may contribute to chronic low-grade neuroinflammation. PMID:24473753

Button, Emily B; Mitchell, Andrew S; Domingos, Marcia M; Chung, Jessica H-J; Bradley, Ryan M; Hashemi, Ashkan; Marvyn, Phillip M; Patterson, Ashley C; Stark, Ken D; Quadrilatero, Joe; Duncan, Robin E

2014-04-01

129

Production of medium chain saturated fatty acids with enhanced antimicrobial activity from crude coconut fat by solid state cultivation of Yarrowia lipolytica.  

PubMed

Fatty acids profiles and antimicrobial activity of crude coconut fat hydrolysates obtained in solid-state cultivation system with a selected yeast strain Yarrowia lipolytica RO13 were performed. A preliminary step regarding extracellular lipase production and solid state enzymatic hydrolysis of crude fat at different water activity and time intervals up to 7 days was also applied. Gas chromatography-mass spectrometry analysis was used for quantification of medium chain saturated fatty acids (MCSFAs) and the results revealed a higher concentration of about 70% lauric acid from total fatty acids. Further, antimicrobial activity of fatty acids against some food-borne pathogens (Salmonella enteritidis, Escherichia coli, Listeria monocytogenes and Bacillus cereus) was evaluated. The minimum inhibitory concentration of the obtained hydrolysates varied from 12.5 to 1.56 ppm, significantly lower than values reported in literature. The results provide substantial evidence for obtaining biopreservative effects by coconut fat enzymatic hydrolysis. PMID:23194533

Parfene, Georgiana; Horincar, Vicentiu; Tyagi, Amit Kumar; Malik, Anushree; Bahrim, Gabriela

2013-02-15

130

Membrane Phospholipid Fatty Acid Composition Regulates Cardiac SERCA Activity in a Hibernator, the Syrian Hamster (Mesocricetus auratus)  

PubMed Central

Polyunsaturated fatty acids (PUFA) have strong effects on hibernation and daily torpor. Increased dietary uptake of PUFA of the n-6 class, particularly of Linoleic acid (LA, C18:2 n-6) lengthens torpor bout duration and enables animals to reach lower body temperatures (Tb) and metabolic rates. As previously hypothesized, this well-known influence of PUFA may be mediated via effects of the membrane fatty acid composition on sarcoplasmic reticulum (SR) Ca2+?ATPase 2a (SERCA) in the heart of hibernators. We tested the hypotheses that high proportions of n-6 PUFA in general, or specifically high proportions of LA (C18:2 n-6) in SR phospholipids (PL) should be associated with increased cardiac SERCA activity, and should allow animals to reach lower minimum Tb in torpor. We measured activity of SERCA from hearts of hibernating and non-hibernating Syrian hamsters (Mesocricetus auratus) in vitro at 35°C. Further, we determined the PL fatty acid composition of the SR membrane of these hearts. We found that SERCA activity strongly increased as the proportion of LA in SR PL increased but was negatively affected by the content of Docosahexaenoic acid (DHA; C22:6 n-3). SR PL from hibernating hamsters were characterized by high proportions of LA and low proportions of DHA. As a result, SERCA activity was significantly higher during entrance into torpor and in torpor compared to inter-bout arousal. Also, animals with increased SERCA activity reached lower Tb during torpor. Interestingly, a subgroup of hamsters which never entered torpor but remained euthermic throughout winter displayed a phenotype similar to animals in summer. This was characterized by lower proportions of LA and increased proportions of DHA in SR membranes, which is apparently incompatible with torpor. We conclude that the PUFA composition of SR membranes affects cardiac function via modulating SERCA activity, and hence determines the minimum Tb tolerated by hibernators. PMID:23650545

Strijkstra, Arjen; Boerema, Ate; Arnold, Walter; Ruf, Thomas

2013-01-01

131

Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development.  

PubMed

Alkamides and N-acylethanolamines (NAEs) are bioactive, amide-linked lipids that influence plant development. Alkamides are restricted to several families of higher plants and some fungi, whereas NAEs are widespread signaling molecules in both plants and animals. Fatty acid amide hydrolase (FAAH) has been described as a key contributor to NAE hydrolysis; however, no enzyme has been associated with alkamide degradation in plants. Herein reported is synthesis of 12 compounds structurally similar to a naturally occurring alkamide (N-isobutyl-(2E,6Z,8E)decatrienamide or affinin) with different acyl compositions more similar to plant NAEs and various amino alkyl head groups. These "hybrid" synthetic alkamides were tested for activity toward recombinant Arabidopsis FAAH and for their effects on plant development (i.e., cotyledon expansion and primary root length). A substantial increase in FAAH activity was discovered toward NAEs in vitro in the presence of some of these synthetic alkamides, such as N-ethyllauroylamide (4). This "enhancement" effect was found to be due, at least in part, to relief from product inhibition of FAAH by ethanolamine, and not due to an alteration in the oligomerization state of the FAAH enzyme. For several of these alkamides, an inhibition of seedling growth was observed with greater results in FAAH knockouts and less in FAAH over-expressing plants, suggesting that these alkamides could be hydrolyzed by FAAH in planta. The tight regulation of NAE levels in vivo appears to be important for proper seedling establishment, and as such, some of these synthetic alkamides may be useful pharmacological tools to manipulate the effects of NAEs in situ. PMID:25491532

Faure, Lionel; Cavazos, Ronaldo; Khan, Bibi Rafeiza; Petros, Robby A; Koulen, Peter; Blancaflor, Elison B; Chapman, Kent D

2015-02-01

132

Hepatocyte nuclear factor-4? contributes to carbohydrate-induced transcriptional activation of hepatic fatty acid synthase  

PubMed Central

Refeeding a carbohydrate-rich meal after a fast produces a co-ordinated induction of key glycolytic and lipogenic genes in the liver. The transcriptional response is mediated by insulin and increased glucose oxidation, and both signals are necessary for optimal induction of FAS (fatty acid synthase). The glucose-regulated component of FAS promoter activation is mediated in part by ChREBP [ChoRE (carbohydrate response element)-binding protein], which binds to a ChoRE between ?7300 and ?7000 base-pairs in a carbohydrate-dependent manner. Using in vivo footprinting with nuclei from fasted and refed rats, we identify an imperfect DR-1 (direct repeat-1) element between ?7110 and ?7090 bp that is protected upon carbohydrate refeeding. Electrophoretic mobility-shift assays establish that this DR-1 element binds HNF-4? (hepatocyte nuclear factor 4?), and chromatin immunoprecipitation establishes that HNF-4? binding to this site is increased approx. 3-fold by glucose refeeding. HNF-4? transactivates reporter constructs containing the distal FAS promoter in a DR-1-dependent manner, and this DR-1 is required for full glucose induction of the FAS promoter in primary hepatocytes. In addition, a 3-fold knockdown of hepatocyte HNF-4? by small interfering RNA produces a corresponding decrease in FAS gene induction by glucose. Co-immunoprecipitation experiments demonstrate a physical interaction between HNF-4? and ChREBP in primary hepatocytes, further supporting an important complementary role for HNF-4? in glucose-induced activation of FAS transcription. Taken together, these observations establish for the first time that HNF-4? functions in vivo through a DR-1 element in the distal FAS promoter to enhance gene transcription following refeeding of glucose to fasted rats. The findings support the broader view that HNF-4? is an integral component of the hepatic nutrient sensing system that co-ordinates transcriptional responses to transitions between nutritional states. PMID:16800817

Adamson, Aaron W.; Suchankova, Gabriela; Rufo, Caterina; Nakamura, Manabu T.; Teran-Garcia, Margarita; Clarke, Steven D.; Gettys, Thomas W.

2006-01-01

133

Dietary (n-3) Fatty Acids Affect Rat Heart, Liver and Aorta Protective Enzyme Activities and Lipid Peroxidation1'2  

Microsoft Academic Search

In a 16-wk study, weanling Wistarrats (32 males and 32 females) were fed a modified AIN-76 diet containing 20% fat with various (n-3) fatty acids. All dietary fats provided the same amount of saturates, monounsaturates, and total essential fatty acids ((n-6) + (n-3)). The control diet contained lard\\/com oil (L\\/CO). The other diets contained (n-3) fatty acids from linseed oil

MARY R. L'ABBÃ; KEITH D. TRICK; JOYCE L BEARE-ROGERS

134

Rosiglitazone increases fatty acid ?9-desaturation and decreases elongase activity index in human skeletal muscle in vivo.  

PubMed

The ratio of unsaturated to saturated long-chain fatty acids (LC-FAs) in skeletal muscle has been associated with insulin resistance. Some animal data suggest a modulatory effect of peroxisome proliferator receptor ? (PPAR?) stimulation on stearoyl-CoA desaturase 1 (SCD1) and LC-FA composition in skeletal muscle, but human data are rare. We here investigate whether treatment with a PPAR? agonist affects myocellular SCD1 expression and modulates the intramyocellular fatty acid profile in individuals with impaired glucose tolerance. Muscle biopsies and hyperinsulinemic-euglycemic clamps were performed in 7 men before and after 8 weeks of rosiglitazone treatment. Intramyocellular saturated, monounsaturated, and polyunsaturated intramuscular fatty acid profiles were measured by gas chromatography. Effects on SCD1 messenger RNA expression were analyzed in C2C12 cells and in human biopsies before and after rosiglitazone treatment. As expected, treatment with the PPAR? activator rosiglitazone improved insulin sensitivity in humans. Myocellular SCD1 messenger RNA expression was increased in human biopsies and C2C12 cells. Although the total content of myocellular LC-FA was unchanged, a relative shift from saturated LC-FAs to unsaturated LC-FAs was observed in human biopsies. Particularly, the amount of stearate was reduced, whereas the amounts of palmitoleate as well as oleate and vaccenate were increased, after rosiglitazone therapy. These changes resulted in an increased fatty acid ?9-desaturation index (16:1/16:0 and 18:1/18:0) in skeletal muscle and a decreased elongase activity index (18:0/16:0). The PPAR? associated phenotypes may be partially explained by an increased ?9-desaturation and a decreased elongase activity of skeletal muscle. PMID:21741058

Mai, Knut; Andres, Janin; Bobbert, Thomas; Assmann, Anke; Biedasek, Katrin; Diederich, Sven; Graham, Ian; Larson, Tony R; Pfeiffer, Andreas F H; Spranger, Joachim

2012-01-01

135

Liquid fructose downregulates Sirt1 expression and activity and impairs the oxidation of fatty acids in rat and human liver cells.  

PubMed

Fructose ingestion is associated with the production of hepatic steatosis and hypertriglyceridemia. For fructose to attain these effects in rats, simultaneous induction of fatty acid synthesis and inhibition of fatty acid oxidation is required. We aimed to determine the mechanism involved in the inhibition of fatty acid oxidation by fructose and whether this effect occurs also in human liver cells. Female rats were supplemented or not with liquid fructose (10% w/v) for 7 or 14 days; rat (FaO) and human (HepG2) hepatoma cells, and human hepatocytes were incubated with fructose 25mM for 24h. The expression and activity of the enzymes and transcription factors relating to fatty acid ?-oxidation were evaluated. Fructose inhibited the activity of fatty acid ?-oxidation only in livers of 14-day fructose-supplemented rats, as well as the expression and activity of peroxisome proliferator activated receptor ? (PPAR?). Similar results were observed in FaO and HepG2 cells and human hepatocytes. PPAR? downregulation was not due to an osmotic effect or to an increase in protein-phosphatase 2A activity caused by fructose. Rather, it was related to increased content in liver of inactive and acetylated peroxisome proliferator activated receptor gamma coactivator 1?, due to a reduction in sirtuin 1 expression and activity. In conclusion, fructose inhibits liver fatty acid oxidation by reducing PPAR? expression and activity, both in rat and human liver cells, by a mechanism involving sirtuin 1 down-regulation. PMID:24434080

Rebollo, Alba; Roglans, Núria; Baena, Miguel; Sánchez, Rosa M; Merlos, Manel; Alegret, Marta; Laguna, Juan C

2014-04-01

136

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

137

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

138

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.

139

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

PubMed

Extracellular fatty acid incorporation into the phospholipids of Staphylococcus aureus occurs via fatty acid phosphorylation. We show that fatty acid kinase (Fak) is composed of two dissociable protein subunits encoded by separate genes. FakA provides the ATP binding domain and interacts with two distinct FakB proteins to produce acyl-phosphate. The FakBs are fatty acid binding proteins that exchange bound fatty acid/acyl-phosphate with fatty acid/acyl-phosphate presented in detergent micelles or liposomes. The ?fakA and ?fakB1 ?fakB2 strains were unable to incorporate extracellular fatty acids into phospholipid. FakB1 selectively bound saturated fatty acids whereas FakB2 preferred unsaturated fatty acids. Affymetrix array showed a global perturbation in the expression of virulence genes in the ?fakA strain. The severe deficiency in ?-hemolysin protein secretion in ?fakA and ?fakB1 ?fakB2 mutants coupled with quantitative mRNA measurements showed that fatty acid kinase activity was required to support virulence factor transcription. These data reveal the function of two conserved gene families, their essential role in the incorporation of host fatty acids by Gram-positive pathogens, and connects fatty acid kinase to the regulation of virulence factor transcription in S. aureus. PMID:25002480

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

2014-07-22

140

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

PubMed Central

Extracellular fatty acid incorporation into the phospholipids of Staphylococcus aureus occurs via fatty acid phosphorylation. We show that fatty acid kinase (Fak) is composed of two dissociable protein subunits encoded by separate genes. FakA provides the ATP binding domain and interacts with two distinct FakB proteins to produce acyl-phosphate. The FakBs are fatty acid binding proteins that exchange bound fatty acid/acyl-phosphate with fatty acid/acyl-phosphate presented in detergent micelles or liposomes. The ?fakA and ?fakB1 ?fakB2 strains were unable to incorporate extracellular fatty acids into phospholipid. FakB1 selectively bound saturated fatty acids whereas FakB2 preferred unsaturated fatty acids. Affymetrix array showed a global perturbation in the expression of virulence genes in the ?fakA strain. The severe deficiency in ?-hemolysin protein secretion in ?fakA and ?fakB1 ?fakB2 mutants coupled with quantitative mRNA measurements showed that fatty acid kinase activity was required to support virulence factor transcription. These data reveal the function of two conserved gene families, their essential role in the incorporation of host fatty acids by Gram-positive pathogens, and connects fatty acid kinase to the regulation of virulence factor transcription in S. aureus. PMID:25002480

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

2014-01-01

141

Fatty Acid Composition and Trans Fatty Acids in Crisps and Cakes in Turkey's Markets  

Microsoft Academic Search

In this study, trans fatty acid and fatty acid composition of 57 crisps and 50 cakes sold in the markets in Turkey were determined. C 18:1, oleic acid, was the major fatty acid in all crisps and cake samples. The percentages of saturated fatty acids (SFAs), monounsaturated fatty acids (MUFAs), and polyunsaturated fatty acids (PUFAs) ranged between 27.98–46.57, 35.73–47.57, and

Yavuz S. Cakmak; Gokalp O. Guler; Sakir Yigit; Gokhan Caglav; Abdurrahman Aktumsek

2011-01-01

142

Fatty acid profiles, tocopherol contents, and antioxidant activities of heartnut (Juglans ailanthifolia Var. cordiformis) and Persian walnut (Juglans regia L.).  

PubMed

The fatty acid and tocopherol compositions of three heartnut (Juglans ailanthifolia var. cordiformis) varieties (Imshu, Campbell CW1, and Campbell CW3) were examined and compared with those of two Persian walnut (Juglans regia L.) varieties (Combe and Lake). The major fatty acids found in heartnuts and walnuts were identified by gas chromatography as linoleic (18:2n-6), alpha-linolenic (18:3n-3), oleic (18:1n-9), palmitic (16:0), and stearic acid (18:0). Polyunsaturated fatty acids were the main group of fatty acids found in both heartnut and walnut, ranging from 73.07 to 80.98%, and were significantly higher in heartnut than in Persian walnuts (P < 0.001). In addition, heartnuts had significantly higher levels of 18:2n-6 and lower levels of 18:3n-3 compared to the Persian walnuts. gamma-Tocopherol was the main tocopherol homologue present in both types of nuts, followed by delta- and alpha-tocopherol. The highest concentration of gamma-tocopherol was found in Combe Persian walnut at 267.87 mug/g, followed by Lake Persian walnut and Imshu, Campbell CW1, and CW3 heartnut at 205.45, 187.33, 161.84, and 126.46 mug/g, respectively. Tocopherols, particularly the gamma-tocopherol, were found to contribute the most to the strong total antioxidant activities of both walnut and heartnut oils using either the free radical 2,2-diphenyl-1-picrylhydrazyl assay or the photochemiluminescence method. PMID:17253708

Li, Li; Tsao, Rong; Yang, Raymond; Kramer, John K G; Hernandez, Marta

2007-02-21

143

Viability, infectivity and fatty acid synthetic activity of Perkinsus marinus meront cells incubated in estuarine and artificial seawater.  

PubMed

We investigated the viability and fatty acid synthetic activity of in vitro cultured Perkinsus marinus (Dermo) in lipid-free medium and estuarine water, and the infectivity of P. marinus maintained in artificial seawater (ASW). Viability and fatty acid synthetic activity in 7 d old P. marinus meronts maintained in lipid-free medium and estuarine water were tested. The infectivity of meronts incubated in ASW was examined by first incubating P. marinus meronts in ASW for 2, 3 or 7 d, and then inoculating viable ASW-incubated meronts into the shell cavity of individual oysters Crassostrea virginica. P. marinus infection prevalence and intensity in oysters were determined 9 wk post-inoculation. Heavy mortality occurred in meronts maintained in estuarine water, a drop from an initial value of 100% viable to 7.8 and 6.1% after 3 and 14 d incubation, respectively. Viability was 85 and 67% in meronts maintained in lipid-free medium for 3 and 24 d, respectively. Meronts kept in lipid-free medium for 14 d retained their ability to synthesize fatty acids. Viable meronts incubated in ASW remained infective for up to 7 d. The infection prevalences were 85, 48 and 100%, in the treatments inoculated with viable meronts that were incubated in ASW for 2, 3 and 7 d, respectively. Infection prevalence in the group inoculated with viable meronts immediately after they were transferred to ASW ranged from 61 to 85%. Our results suggest that in nature meronts can survive for at least 14 d outside the host. Viable meronts are not only infective, but are also able to replicate and retain their fatty acid synthetic ability for 7 d. PMID:16956060

Chu, Fu-Lin E; Lund, Eric D

2006-07-25

144

Unsaturated fatty acids in the postnatally developing rat lung  

Microsoft Academic Search

Fatty acid desaturase activity specific for the C-9 position is present in lung microsomes prepared from rats of all ages.\\u000a This activity is significantly lower in neonatal rat lung compared with adult lung. A rapid increase in C-9 fatty acid desaturase\\u000a activity seen at the approximate time of weaning may be related to a decrease in the polyunsaturated fatty acid

James P. Kehrer; Anne P. Autor

1983-01-01

145

AMP-activated protein kinase and coordination of hepatic fatty acid metabolism of starved/carbohydrate-refed rats.  

PubMed

Acute increases in the concentration of malonyl-CoA play a pivotal role in mediating the decrease in fatty acid oxidation that occurs in many tissues during refeeding after a fast. In this study, we assess whether such increases in malonyl-CoA in liver could be mediated by malonyl-CoA decarboxylase (MCD), as well as acetyl-CoA carboxylase (ACC). In addition, we examine how changes in the activity of ACC, MCD, and other enzymes that govern fatty acid and glycerolipid synthesis relate temporally to alterations in the activities of the fuel-sensing enzyme AMP-activated protein kinase (AMPK). Rats starved for 48 h and refed a carbohydrate chow diet for 1, 3, 12, and 24 h were studied. Refeeding caused a 40% decrease in the activity of the alpha1-isoform of AMPK within 1 h, with additional decreases in AMPKalpha1 activity and a decrease in AMPKalpha2 occurring between 1 and 24 h. At 1 h, the decrease in AMPK activity was associated with an eightfold increase in the activity of the alpha1-isoform of ACC and a 30% decrease in the activity of MCD, two enzymes thought to be regulated by AMPK. Also, the concentration of malonyl-CoA was increased by 50%. Between 1 and 3 h of refeeding, additional increases in the activity of ACC and decreases in MCD were observed, as was a further twofold increase in malonyl-CoA. Increases in the activity (60%) and abundance (12-fold) of fatty acid synthase occurred predominantly between 3 and 24 h and increases in the activity of mitochondrial sn-glycerol-3-phosphate acyltransferase (GPAT) and acyl-CoA:diaclyglycerol acyltransferase (DGAT) at 12 and 24 h. The results strongly suggest that early changes in the activity of MCD, as well as ACC, contribute to the increase in hepatic malonyl-CoA in the starved-refed rat. They also suggest that the changes in these enzymes, and later occurring increases in enzymes regulating fatty acid and glycerolipid synthesis, could be coordinated by AMPK. PMID:15956049

Assifi, Murwarid M; Suchankova, Gabriela; Constant, Scarlet; Prentki, Marc; Saha, Asish K; Ruderman, Neil B

2005-11-01

146

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

PubMed Central

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

Bomford, R

1981-01-01

147

Synthesis and characterization of some novel fatty acid analogues: A preliminary investigation on their activity against human lung carcinoma cell line  

PubMed Central

Background Preparation of some novel heterocyclic compounds with long alkyl and alkenyl chain of cytotoxic activity. Methods Gamma linolenic acid, a poly unsaturated fatty acid and stearic acid, a saturated fatty acid were isolated from the microalga Spirulina platensis. Some novel gamma linolenic acid and stearic acid analogues having 1,3,4-oxadiazole and 1,2,4-triazole were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. Cytotoxicity of these compounds was evaluated by the growth inhibition of A-549 cells in-vitro. Results Compound 1 and 3 showed comparable cytotoxicity against the human lung carcinoma A-549 cell lines. PMID:23537396

2013-01-01

148

Palmitate activation by fatty acid transport protein 4 as a model system for hepatocellular apoptosis and steatosis.  

PubMed

Fatty acid transport protein (FATP) 4 is a minor FATP in the liver but it has some activity towards palmitate 16:0 (Pal). We here chose FATP4 as a representative model enzyme for acyl-CoA synthetases (ACSs), and FATPs to determine whether Pal activation would lead to apoptosis and alteration in lipid metabolism. By using FATP4 overexpressed (FATP4) Huh-7 cells, we showed that FATP4 was localized in the endoplasmic reticulum (ER) and mitochondria of FATP4 cells. FATP4 cells were more responsive to Pal than the control GFP cells in increasing palmitoyl-CoA and oleoyl-CoA activities as well as apoptosis by ~2-3 folds. The lipoapoptosis susceptibility by FATP4 was coupled with the increased JNK, PUMA, caspase3, PARP-1 activation as well as Rac-1-mediated cytoskeletal reorganization, and decreased insulin sensitivity. This was associated with increased contents of neutral lipids and significant alteration in composition of phospholipids and sphingolipids including increased lysophosphatidylcholine (LPC), ceramide, and hexosylceramide, as well as an increase of saturated:polyunsaturated fatty acid ratio in LPC and PC, but a decrease of this ratio in phosphatidylethanolamine pool. By use of ceramide synthase inhibitors, our results showed that FATP4-sensitized lipoapoptosis was not mediated by ceramides. Moreover, FATP4 expression was increased in fatty livers in vivo. Thus, our model system has provided a clue that Pal activation FATP4 triggers hepatocellular apoptosis via altered phospholipid composition and steatosis by acylation into complex lipids. This may be a redundant mechanism for other ER-localizing ACSs and FATPs in the liver, and hence their involvement in the development of fatty liver disease. PMID:25603556

Seeßle, Jessica; Liebisch, Gerhard; Schmitz, Gerd; Stremmel, Wolfgang; Chamulitrat, Walee

2015-05-01

149

Abundance and distribution of fatty acids within the walls of an active deep-sea sulfide chimney  

NASA Astrophysics Data System (ADS)

Abundance and distribution of total fatty acids (TFAs) were examined along the physicochemical gradient within an active hydrothermal chimney collected from the Main Endeavour segment of Juan de Fuca Ridge. Approximately 27 fatty acids are identified with a chain-length ranging from C12 to C22. From the exterior to the interior of the chimney walls, the total concentrations of TFAs (? TFAs) show a trend of evident decrease. The observed compositions of TFAs are rich in bacterial biomarkers especially monounsaturated fatty acids (MUFAs) and minor branched and cyclopropyl FAs. On the basis of the species-specific FAs and bacterial 16SrRNA gene analysis (Li et al., unpublished data), sulfur-based metabolism appears to be the essential metabolic process in the chimney. Furthermore, the sulfur oxidizing bacteria (SOB) are identified as a basic component of microbial communities at the exterior of the hydrothermal chimney, and its proportion shows an inward decrease while the sulfate reducing bacteria (SRB) have an inverse distribution.

Li, Jiwei; Zhou, Huaiyang; Peng, Xiaotong; Fu, Meiyan; Chen, Zhiqiang; Yao, Huiqiang

2011-04-01

150

Endocannabinoid activation at hepatic CB1 receptors stimulates fatty acid synthesis and contributes to diet-induced obesity  

PubMed Central

Endogenous cannabinoids acting at CB1 receptors stimulate appetite, and CB1 antagonists show promise in the treatment of obesity. CB1–/– mice are resistant to diet-induced obesity even though their caloric intake is similar to that of wild-type mice, suggesting that endocannabinoids also regulate fat metabolism. Here, we investigated the possible role of endocannabinoids in the regulation of hepatic lipogenesis. Activation of CB1 in mice increases the hepatic gene expression of the lipogenic transcription factor SREBP-1c and its targets acetyl-CoA carboxylase-1 and fatty acid synthase (FAS). Treatment with a CB1 agonist also increases de novo fatty acid synthesis in the liver or in isolated hepatocytes, which express CB1. High-fat diet increases hepatic levels of the endocannabinoid anandamide (arachidonoyl ethanolamide), CB1 density, and basal rates of fatty acid synthesis, and the latter is reduced by CB1 blockade. In the hypothalamus, where FAS inhibitors elicit anorexia, SREBP-1c and FAS expression are similarly affected by CB1 ligands. We conclude that anandamide acting at hepatic CB1 contributes to diet-induced obesity and that the FAS pathway may be a common molecular target for central appetitive and peripheral metabolic regulation. PMID:15864349

Osei-Hyiaman, Douglas; DePetrillo, Michael; Pacher, Pál; Liu, Jie; Radaeva, Svetlana; Bátkai, Sándor; Harvey-White, Judith; Mackie, Ken; Offertáler, László; Wang, Lei; Kunos, George

2005-01-01

151

Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria.  

PubMed

There is growing evidence that the role of lipids in innate immunity is more important than previously realized. How lipids interact with bacteria to achieve a level of protection, however, is still poorly understood. To begin to address the mechanisms of antibacterial activity, we determined MICs and minimum bactericidal concentrations (MBCs) of lipids common to the skin and oral cavity--the sphingoid bases D-sphingosine, phytosphingosine, and dihydrosphingosine and the fatty acids sapienic acid and lauric acid--against four Gram-negative bacteria and seven Gram-positive bacteria. Exact Kruskal-Wallis tests of these values showed differences among lipid treatments (P < 0.0001) for each bacterial species except Serratia marcescens and Pseudomonas aeruginosa. D-sphingosine (MBC range, 0.3 to 19.6 ?g/ml), dihydrosphingosine (MBC range, 0.6 to 39.1 ?g/ml), and phytosphingosine (MBC range, 3.3 to 62.5 ?g/ml) were active against all bacteria except S. marcescens and P. aeruginosa (MBC > 500 ?g/ml). Sapienic acid (MBC range, 31.3 to 375.0 ?g/ml) was active against Streptococcus sanguinis, Streptococcus mitis, and Fusobacterium nucleatum but not active against Escherichia coli, Staphylococcus aureus, S. marcescens, P. aeruginosa, Corynebacterium bovis, Corynebacterium striatum, and Corynebacterium jeikeium (MBC > 500 ?g/ml). Lauric acid (MBC range, 6.8 to 375.0 ?g/ml) was active against all bacteria except E. coli, S. marcescens, and P. aeruginosa (MBC > 500 ?g/ml). Complete killing was achieved as early as 0.5 h for some lipids but took as long as 24 h for others. Hence, sphingoid bases and fatty acids have different antibacterial activities and may have potential for prophylactic or therapeutic intervention in infection. PMID:22155833

Fischer, Carol L; Drake, David R; Dawson, Deborah V; Blanchette, Derek R; Brogden, Kim A; Wertz, Philip W

2012-03-01

152

Antibacterial Activity of Sphingoid Bases and Fatty Acids against Gram-Positive and Gram-Negative Bacteria  

PubMed Central

There is growing evidence that the role of lipids in innate immunity is more important than previously realized. How lipids interact with bacteria to achieve a level of protection, however, is still poorly understood. To begin to address the mechanisms of antibacterial activity, we determined MICs and minimum bactericidal concentrations (MBCs) of lipids common to the skin and oral cavity—the sphingoid bases d-sphingosine, phytosphingosine, and dihydrosphingosine and the fatty acids sapienic acid and lauric acid—against four Gram-negative bacteria and seven Gram-positive bacteria. Exact Kruskal-Wallis tests of these values showed differences among lipid treatments (P < 0.0001) for each bacterial species except Serratia marcescens and Pseudomonas aeruginosa. d-Sphingosine (MBC range, 0.3 to 19.6 ?g/ml), dihydrosphingosine (MBC range, 0.6 to 39.1 ?g/ml), and phytosphingosine (MBC range, 3.3 to 62.5 ?g/ml) were active against all bacteria except S. marcescens and P. aeruginosa (MBC > 500 ?g/ml). Sapienic acid (MBC range, 31.3 to 375.0 ?g/ml) was active against Streptococcus sanguinis, Streptococcus mitis, and Fusobacterium nucleatum but not active against Escherichia coli, Staphylococcus aureus, S. marcescens, P. aeruginosa, Corynebacterium bovis, Corynebacterium striatum, and Corynebacterium jeikeium (MBC > 500 ?g/ml). Lauric acid (MBC range, 6.8 to 375.0 ?g/ml) was active against all bacteria except E. coli, S. marcescens, and P. aeruginosa (MBC > 500 ?g/ml). Complete killing was achieved as early as 0.5 h for some lipids but took as long as 24 h for others. Hence, sphingoid bases and fatty acids have different antibacterial activities and may have potential for prophylactic or therapeutic intervention in infection. PMID:22155833

Fischer, Carol L.; Drake, David R.; Dawson, Deborah V.; Blanchette, Derek R.; Brogden, Kim A.

2012-01-01

153

[Omega-3 fatty acids in psychiatry].  

PubMed

The brain is one of the organs with the highest level of lipids (fats). Brain lipids, formed of fatty acids, participate in the structure of membranes, for instance 50 % fatty acids are polyunsaturated in the gray matter, 1/3 are of the omega-3 family, and are thus of dietary origin. The omega-3 fatty acids (mainly alpha-linolenic acid, ALA) participated in one of the first experimental demonstration of the effect of dietary substances (nutrients) on the structure and function of the brain. Experiments were first of all carried out on ex vivo cultured brain cells, then on in vivo brain cells (neurons, astrocytes and oligodendrocytes) from animals fed ALA deficient diet, finally on physicochemical (membrane fluidity), biochemical, physiological, neurosensory (vision an auditory responses), and behavioural or learning parameters. These findings indicated that the nature of polyunsaturated fatty acids (in particular omega-3) present in formula milks for human infants determines to a certain extend the visual, neurological, and intellectual abilities. Thus, in view of these results and of the high polyunsaturated fatty acid content of the brain, it is normal to consider that they could be involved in psychiatric diseases and in the cognitive decline of ageing. Omega-3 fatty acids appear effective in the prevention of stress, however their role as regulator of mood is a matter for discussion. Indeed, they play a role in the prevention of some disorders including depression (especially post partum), as well as in dementia, particularly Alzheimer's disease. Their role in major depression and bipolar disorder (manic-depressive disease), only poorly documented, is not clearly demonstrated. The intervention of omega-3 in dyslexia, autism, and schizophrenia has been suggested, but it does not necessarily infer a nutritional problems. The respective importance of the vascular system (where the omega-3 are actually active) and the cerebral parenchyma itself, remain to be resolved. However, the insufficient supply of omega-3 fatty acids in today diet in occidental (less than 50 % of the recommended dietary intakes values for ALA) raises the problem of how to correct inadequate dietary habits, by prescribing mainly rapeseed (canola) and walnut oils on the one hand, fatty fish (wild, or farmed, but the nature of fatty acids present in fish flesh is the direct consequence of the nature of fats with which they have been fed), and eggs from laying hens fed omega-3 fatty acids. PMID:15691497

Bourre, Jean-Marie

2005-02-01

154

Dietary ?-Polylysine Decreased Serum and Liver Lipid Contents by Enhancing Fecal Lipid Excretion Irrespective of Increased Hepatic Fatty Acid Biosynthesis-Related Enzymes Activities in Rats  

PubMed Central

?-Polylysine (EPL) is used as a natural preservative in food. However, few studies have been conducted to assess the beneficial functions of dietary EPL. The purpose of this study was to elucidate the mechanism underlying the inhibition of neutral and acidic sterol absorption and hepatic enzyme activity-related fatty acid biosynthesis following EPL intake. EPL digest prepared using an in vitro digestion model had lower lipase activity and micellar lipid solubility and higher bile acid binding capacity than casein digest. Male Wistar rats were fed an AIN-93G diet containing 1% (wt/wt) EPL or l-lysine. After 4 weeks of feeding these diets, the marked decrease in serum and liver triacylglycerol contents by the EPL diet was partly attributed to increased fecal fatty acid excretion. The activities of hepatic acetyl-coenzyme A carboxylase and glucose-6-phosphate dehydrogenase, which are key enzymes of fatty acid biosynthesis, were enhanced in rats fed EPL diet. The increased fatty acid biosynthesis activity due to dietary EPL may be prevented by the enhancement of fecal fatty acid excretion. The hypocholesterolemic effect of EPL was mediated by increased fecal neutral and acidic sterol excretions due to the EPL digest suppressing micellar lipid solubility and high bile acid binding capacity. These results show that dietary EPL has beneficial effects that could help prevent lifestyle-related diseases such as hyperlipidemia and atherosclerosis.

Hosomi, Ryota; Yamamoto, Daiki; Otsuka, Ren; Nishiyama, Toshimasa; Yoshida, Munehiro; Fukunaga, Kenji

2015-01-01

155

Structural basis for ligand regulation of the fatty acid-binding protein 5, peroxisome proliferator-activated receptor ?/? (FABP5-PPAR?/?) signaling pathway.  

PubMed

Fatty acid-binding proteins (FABPs) are a widely expressed group of calycins that play a well established role in solubilizing cellular fatty acids. Recent studies, however, have recast FABPs as active participants in vital lipid-signaling pathways. FABP5, like its family members, displays a promiscuous ligand binding profile, capable of interacting with numerous long chain fatty acids of varying degrees of saturation. Certain "activating" fatty acids induce the protein's cytoplasmic to nuclear translocation, stimulating PPAR?/? transactivation; however, the rules that govern this process remain unknown. Using a range of structural and biochemical techniques, we show that both linoleic and arachidonic acid elicit FABP5's translocation by permitting allosteric communication between the ligand-sensing ?2 loop and a tertiary nuclear localization signal within the ?-helical cap of the protein. Furthermore, we show that more saturated, nonactivating fatty acids inhibit nuclear localization signal formation by destabilizing this activation loop, thus implicating FABP5 specifically in cis-bonded, polyunsaturated fatty acid signaling. PMID:24692551

Armstrong, Eric H; Goswami, Devrishi; Griffin, Patrick R; Noy, Noa; Ortlund, Eric A

2014-05-23

156

Polyunsaturated fatty acids, neuroinflammation and well being.  

PubMed

The innate immune system of the brain is principally composed of microglial cells and astrocytes, which, once activated, protect neurons against insults (infectious agents, lesions, etc.). Activated glial cells produce inflammatory cytokines that act specifically through receptors expressed by the brain. The functional consequences of brain cytokine action (also called neuroinflammation) are alterations in cognition, mood and behaviour, a hallmark of altered well-being. In addition, proinflammatory cytokines play a key role in depression and neurodegenerative diseases linked to aging. Polyunsaturated fatty acids (PUFA) are essential nutrients and essential components of neuronal and glial cell membranes. PUFA from the diet regulate both prostaglandin and proinflammatory cytokine production. n-3 fatty acids are anti-inflammatory while n-6 fatty acids are precursors of prostaglandins. Inappropriate amounts of dietary n-6 and n-3 fatty acids could lead to neuroinflammation because of their abundance in the brain and reduced well-being. Depending on which PUFA are present in the diet, neuroinflammation will, therefore, be kept at a minimum or exacerbated. This could explain the protective role of n-3 fatty acids in neurodegenerative diseases linked to aging. PMID:20227866

Layé, Sophie

2010-01-01

157

Use of agar diffusion assay to measure bactericidal activity of alkaline salts of fatty acids against bacteria associated with poultry processing  

Technology Transfer Automated Retrieval System (TEKTRAN)

The agar diffusion assay was used to examine antibacterial activity of alkaline salts of caproic, caprylic, capric, lauric, and myristic acids. A 0.5M concentration of each fatty acid was dissolved in 1.0 M potassium hydroxide (KOH), and pH of the mixtures was adjusted to 10.5 with citric acid. Solu...

158

Fatty acid biosynthesis in actinomycetes  

PubMed Central

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

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

2011-01-01

159

Fatty acid amides and anilides, syntheses and antimicrobial properties  

Microsoft Academic Search

A series of fatty acid amides anilides was prepared and a number of compounds in the series were found to be highly active\\u000a against gram positive bacteria but ineffective against gram negative organisms. The N,N-dimethyl- and N,N-diethylamides of\\u000a C12-C14 fatty acids had minimal inhibitory concentration (MIC) values of 100 ppm or less. Substituted anilides of C6-C11 fatty acids were active

E. W. Maurer; F. D. Smith; W. M. Linfield

1980-01-01

160

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

161

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

162

Yhhu981, a novel compound, stimulates fatty acid oxidation via the activation of AMPK and ameliorates lipid metabolism disorder in ob/ob mice  

PubMed Central

Aim: Defects in fatty acid metabolism contribute to the pathogenesis of insulin resistance and obesity. In this study, we investigated the effects of a novel compound yhhu981 on fatty acid metabolism in vitro and in vivo. Methods: The capacity to stimulate fatty acid oxidation was assessed in C2C12 myotubes. The fatty acid synthesis was studied in HepG2 cells using isotope tracing. The phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) was examined with Western blot analysis. For in vivo experiments, ob/ob mice were orally treated with yhhu981 acutely (300 mg/kg) or chronically (150 or 300 mg·kg?1·d?1 for 22 d). On the last day of treatment, serum and tissue samples were collected for analysis. Results: Yhhu981 (12.5–25 ?mol/L) significantly increased fatty acid oxidation and the expression of related genes (Sirt1, Pgc1? and Mcad) in C2C12 myotubes, and inhibited fatty acid synthesis in HepG2 cells. Furthermore, yhhu981 dose-dependently increased the phosphorylation of AMPK and ACC in both C2C12 myotubes and HepG2 cells. Compound C, an AMPK inhibitor, blocked fatty acid oxidation in yhhu981-treated C2C12 myotubes and fatty acid synthesis decrease in yhhu981-treated HepG2 cells. Acute administration of yhhu981 decreased the respiratory exchange ratio in ob/ob mice, whereas chronic treatment with yhhu981 ameliorated the lipid abnormalities and ectopic lipid deposition in skeletal muscle and liver of ob/ob mice. Conclusion: Yhhu981 is a potent compound that stimulates fatty acid oxidation, and exerts pleiotropic effects on lipid metabolism by activating AMPK. PMID:25732571

Zeng, Hong-liang; Huang, Su-ling; Xie, Fu-chun; Zeng, Li-min; Hu, You-hong; Leng, Ying

2015-01-01

163

Fatty acid synthesis and elongation in yeast.  

PubMed

Fatty acids are essential compounds in the cell. Since the yeast Saccharomyces cerevisiae does not feed typically on fatty acids, cellular function and growth relies on endogenous synthesis. Since all cellular organelles are involved in--or dependent on--fatty acid synthesis, multiple levels of control may exist to ensure proper fatty acid composition and homeostasis. In this review, we summarize what is currently known about enzymes involved in cellular fatty acid synthesis and elongation, and discuss potential links between fatty acid metabolism, physiology and cellular regulation. PMID:16950653

Tehlivets, Oksana; Scheuringer, Kim; Kohlwein, Sepp D

2007-03-01

164

A single amino acid change humanizes long-chain fatty acid binding and activation of mouse peroxisome proliferator-activated receptor ?.  

PubMed

Peroxisome proliferator-activated receptor ? (PPAR?) is an important regulator of hepatic lipid metabolism which functions through ligand binding. Despite high amino acid sequence identity (>90%), marked differences in PPAR? ligand binding, activation and gene regulation have been noted across species. Similar to previous observations with synthetic agonists, we have recently reported differences in ligand affinities and extent of activation between human PPAR? (hPPAR?) and mouse PPAR? (mPPAR?) in response to long chain fatty acids (LCFA). The present study was aimed to determine if structural alterations could account for these differences. The binding of PPAR? to LCFA was examined through in silico molecular modeling and docking simulations. Modeling suggested that variances at amino acid position 272 are likely to be responsible for differences in saturated LCFA binding to hPPAR? and mPPAR?. To confirm these results experimentally, LCFA binding, circular dichroism, and transactivation studies were performed using a F272I mutant form of mPPAR?. Experimental data correlated with in silico docking simulations, further confirming the importance of amino acid 272 in LCFA binding. Although the driving force for evolution of species differences at this position are yet unidentified, this study enhances our understanding of ligand-induced regulation by PPAR? and demonstrates the efficacy of molecular modeling and docking simulations. PMID:24858253

Oswal, Dhawal P; Alter, Gerald M; Rider, S Dean; Hostetler, Heather A

2014-06-01

165

AMP kinase activation with AICAR further increases fatty acid oxidation and blunts triacylglycerol hydrolysis in contracting rat soleus muscle  

PubMed Central

Muscle contraction increases glucose uptake and fatty acid (FA) metabolism in isolated rat skeletal muscle, due at least in part to an increase in AMP-activated kinase activity (AMPK). However, the extent to which AMPK plays a role in the regulation of substrate utilization during contraction is not fully understood. We examined the acute effects of 5-aminoimidazole-4-carboxamide riboside (AICAR; 2 mm), a pharmacological activator of AMPK, on FA metabolism and glucose oxidation during high intensity tetanic contraction in isolated rat soleus muscle strips. Muscle strips were exposed to two different FA concentrations (low fatty acid, LFA, 0.2 mm; high fatty acid, HFA, 1 mm) to examine the role that FA availability may play in both exogenous and endogenous FA metabolism with contraction and AICAR. Synergistic increases in AMPK ?2 activity (+45%; P < 0.05) were observed after 30 min of contraction with AICAR, which further increased exogenous FA oxidation (LFA: +71%, P < 0.05; HFA: +46%, P < 0.05) regardless of FA availability. While there were no changes in triacylglycerol (TAG) esterification, AICAR did increase the ratio of FA partitioned to oxidation relative to TAG esterification (LFA: +65%, P < 0.05). AICAR significantly blunted endogenous TAG hydrolysis (LFA: ?294%, P < 0.001; HFA: ?117%, P < 0.05), but had no effect on endogenous oxidation rates, suggesting a better matching between TAG hydrolysis and subsequent oxidative needs of the muscle. There was no effect of AICAR on the already elevated rates of glucose oxidation during contraction. These results suggest that FA metabolism is very sensitive to AMPK ?2 stimulation during contraction. PMID:15774529

Smith, Angela C; Bruce, Clinton R; Dyck, David J

2005-01-01

166

A potential plant-derived antifungal acetylenic acid mediates its activity by interfering with fatty acid homeostasis  

Technology Transfer Automated Retrieval System (TEKTRAN)

6-Nonadecynoic acid (6-NDA), a plant-derived acetylenic acid, exhibits strong inhibitory activity against the human fungal pathogens Candida albicans, Aspergillus fumigatus, and Trichophyton mentagrophytes. In the present study, transcriptional profiling coupled with mutant and biochemical analyses...

167

Inhibition of the reductive activation of a valyl-tRNA synthetase from yeast by unsaturated fatty acids and associated observations on newly found lipophilic substances from yeast.  

PubMed

The reductive activation of a valyl-tRNA synthetase from yeast is strongly inhibited by 1-30 microM unsaturated fatty acids, and the inhibition is antagonized by 10-100 microM saturated fatty acids. Diethylstilbestrol also inhibits the activation. The possibility that unesterified palmitoleic and oleic acids are bona fide regulatory effectors is supported by a dramatic inverse relation between their cellular content and the growth rate of commercial bakers' yeast. An increase in the ratio of unsaturated to saturated acids with slowing growth in a laboratory strain, S288C, also supports the regulatory hypothesis. The free fatty acids are extracted into slightly acidified 50% alcohol together with traces of numerous novel lipophilic substances. One of these is suggested to function as a cofactor in conjunction with a heat-stable polypeptide that activates valyl-tRNA synthetase. PMID:3880744

Black, S

1985-01-10

168

Suicide Deaths of Active Duty U.S. Military and Omega-3 Fatty Acid Status: A Case Control Comparison  

PubMed Central

Background The recent escalation of US Military suicide deaths to record numbers has been an sentinel for impaired force efficacy and has accelerated the search for reversible risk factors. Objective Determine if deficiencies of neuroactive highly unsaturated omega-3 essential fatty acids (n-3 HUFA), in particular docosahexaenoic acid (DHA), are associated with increased risk of suicide death among a large random sample of active duty US military. Methods Serum fatty acids were quantified as % of total fatty acids, among US military suicide deaths (n= 800) and controls (n=800) matched for age, date of collection, sex, rank and year of incident. Participants were Active Duty US Military personnel (2002–2008). Outcome measures, included death by suicide, post deployment health assessment questionnaire and ICD-9 mental health diagnosis data. Results Risks of suicide death was 14% higher, per standard deviation [SD] lower DHA % (OR =1.14, 95% CI; 1.02–1.27, p<0.03), in adjusted logistic regressions. Among men risk of suicide death was 62% greater with low serum DHA status (adjusted Odds Ratio [OR] =1.62, 95% CI 1.12–2.34, p<0.01, comparing DHA below 1.75% [n=1,389] to above [n=141]). Risk of suicide death was 54% greater in those who reported having seen wounded, dead or killed coalition personnel (OR = 1.54, 95% CI; 1.12–2.12, p< 0.007.) Conclusion This US military population had a very low and narrow range of n-3 HUFA status. Although these data suggest that low serum DHA may be a risk factor for suicides, well designed intervention trials are needed to evaluate causality. PMID:21903029

Lewis, Michael D.; Hibbeln, Joseph R.; Johnson, Jeremiah E.; Lin, Yu Hong; Hyun, Duk Y.; Loewke, James D.

2011-01-01

169

Fatty acid flippase activity of UCP2 is essential for its proton transport in mitochondria.  

PubMed

Modulation of cellular energy expenditure is fundamental to normal and pathological cell growth and differentiation. Mitochondria stores energy as a proton gradient across their inner membrane. Uncoupling proteins (UCPs) can dissipate the gradient to produce heat or regulate metabolite fluxes. UCP-mediated proton currents require fatty acids (FAs) and are blocked by nucleotides, but the molecular basis of these processes is unknown. We find, by nuclear magnetic resonance and functional mutagenesis, that UCP2 can bind FAs laterally through its peripheral site, and this intramembrane molecular recognition is essential for UCP2-catalyzed FA flipping across the membrane, which in turn is essential for proton translocation. The antagonist GDP binds inside the UCP2 cavity and perturbs its conformation, which can displace FA from the peripheral site as a mean of inhibiting proton currents. Our data provide a biophysical perspective of the intricate interplay of UCPs, FA, and nucleotides in determining proton fluxes in mitochondria. PMID:25127353

Berardi, Marcelo J; Chou, James J

2014-09-01

170

Nutritional factors affecting the fatty acid composition of bovine milk  

Microsoft Academic Search

The predominant fatty acids in milk are the long-chain fatty acids myristic, palmitic and stearic. These saturated fatty acids account for 75 % of the total fatty acids, with a further 21 % occurring as monounsaturated fatty acids of which the most prevalent is oleic acid. Only 4 g\\/lOO g of the milk fatty acids are polyunsaturated, occurring mainly as

R. J. Mansbridge; J. S. Blake

1997-01-01

171

Essential fatty acids in clinically stable children with propionic acidaemia  

Microsoft Academic Search

Disturbances of fatty acid metabolism with accumulation of odd-chain fatty acids have been reported in propionic acidaemia (PA). It is not known whether the synthesis of long-chain polyunsaturated fatty acids (LCPUFA) is also affected. In five clinically stable children with PA (median age 8 years, range 3.5-9.5 years; median percentage fibroblast propionyl-CoA carboxylase activity 0.8, range 0.8-1.5), we determined the

T. Decsi; W. Sperl; B. Koletzko

1997-01-01

172

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

173

Regulation of the metabolism of polyunsaturated fatty acids.  

PubMed

The object of the present work has been to assess some aspects of the control of the metabolism of polyunsaturated fatty acids. In these studies we have used isolated cells; hepatocytes and cardiac myocytes from rat, and lymphocytes and fibroblasts from humans. Attention has focused on the importance of dietary and hormonal factors which can exert an effect shortly after activation of fatty acid, and thus may determine whether the fatty acid will be desaturated, chain-elongated, directly esterified or oxidized. Both the short-term and long-term regulation excerted by dietary fat have been studied in both rat and human. Profound sex-differences exist in fatty acid esterification, oxidation and fatty acid composition in lipoproteins. It is suggested that these differences, at least in part are due to a different content of intracellular fatty acid binding proteins in female and male liver. The peroxisomal retroconversion of C22-unsaturated fatty acids to their C20-homologues is probably involved in the regulation of fatty acid composition in membrane phospholipids, being a sort of "overflow valve". In several somewhat different diseases the patients have no peroxisomes or their peroxisomes are defective. In these peroxisomal diseases the beta-oxidation of very long-chain fatty acids is deficient. In this present work we show that fibroblast from patients with the peroxisomal diseases, Zellweger disease, X-linked adrenoleukodystrophy and neonatal adrenoleukodystrophy differ in their ability to shorten C22-fatty acids. PMID:3073521

Hagve, T A; Christensen, E; Grønn, M; Christophersen, B O

1988-01-01

174

AMP-Activated Protein Kinase Activation by AICAR Increases Both Muscle Fatty Acid and Glucose Uptake in White Muscle of Insulin-Resistant Rats In Vivo  

Microsoft Academic Search

Insulin-stimulated glucose uptake is increased in white but not red muscle of insulin-resistant high-fat-fed (HF) rats after administration of the AMP-activated protein kinase (AMPK) activator 5-aminoimidazole-4- carboxamide-1--D-ribofuranoside (AICAR). To investi- gate whether a lesser AICAR effect on glucose uptake in red muscle was offset by a greater effect on fatty acid (FA) uptake, we examined acute effects of AICAR on

Miguel A. Iglesias; Stuart M. Furler; Gregory J. Cooney; Edward W. Kraegen; Ji-Ming Ye

2004-01-01

175

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

176

Biochemical and Molecular Roles of Nutrients Fatty Acid Composition and Fatty Acid Elongase and Stearoyl-CoA Desaturase Activities in Tissues of Steers Fed High Oleate Sunflower Seed1'2  

Microsoft Academic Search

The effects of a high oleate sunflower seed diet on tissue composition and on fatty acid elongation and desaturation enzyme activities were investigated. Three Simmental calves were fed a standard corn-based diet (2.6% fat); three others were fed the corn-based diet containing 20% high oleate sunflower seed (10.4% fat). Blood samples and perianal adipose tissue samples were obtained at 7,

JOYCE H. P. CHANG; DAVID K. LÃœNTANDSTEPHEN; B. SMITH

177

Adiponectin stimulates glucose utilization and fatty-acid oxidation by activating AMP-activated protein kinase  

Microsoft Academic Search

Adiponectin (Ad) is a hormone secreted by adipocytes that regulates energy homeostasis and glucose and lipid metabolism. However, the signaling pathways that mediate the metabolic effects of Ad remain poorly identified. Here we show that phosphorylation and activation of the 5?-AMP-activated protein kinase (AMPK) are stimulated with globular and full-length Ad in skeletal muscle and only with full-length Ad in

T. Yamauchi; J. Kamon; Y. Minokoshi; Y. Ito; H. Waki; S. Uchida; S. Yamashita; M. Noda; S. Kita; K. Ueki; K. Eto; Y. Akanuma; P. Froguel; F. Foufelle; P. Ferre; D. Carling; S. Kimura; R. Nagai; B. B. Kahn; T. Kadowaki

2002-01-01

178

Why do polyunsaturated fatty acids lower serum  

Microsoft Academic Search

Replacement of saturated by polyunsaturated fatty acids in the diet may lower serum very low-density and low-density lipoprotein concentrations because the liver preferentially converts polyunsaturated fatty acids into ketone bodies instead of into very low-density lipoprotein triglycerides. Thus unlike saturated fatty acids, polyunsaturated fatty acids are transported to the tissues for oxidation without leaving a trail of lipoprotein remnants in

Anion C Beynen; Martijn B Katan

179

Dietary fatty acids and minerals  

Technology Transfer Automated Retrieval System (TEKTRAN)

Accumulating evidence in animals and humans shows that dietary fatty acids influence the absorption and utilization of certain mineral elements. Fat intake exceeding 10% of energy intake reduces calcium uptake and use by the body, and this effect is more pronounced with saturated compared to unsatu...

180

Flagging the fatty acid ferryman.  

PubMed

Fatty acids made in chloroplasts must be exported into the rest of the cell to be converted into commercially important plant oils. A new study identifies FAX1 as a protein that mediates this crucial transport step. Read the Research Article. PMID:25646782

Roberts, Roland G

2015-02-01

181

Hypothalamic sensing of fatty acids  

Microsoft Academic Search

Selective regions of the brain, including the hypothalamus, are capable of gathering information on the body's nutritional status in order to implement appropriate behavioral and metabolic responses to changes in fuel availability. This review focuses on direct metabolic signaling within the hypothalamus. There is growing evidence supporting the idea that fatty acid metabolism within discrete hypothalamic regions can function as

Tony K T Lam; Gary J Schwartz; Luciano Rossetti

2005-01-01

182

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

183

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

184

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2010 CFR

... 2010-04-01 2009-04-01 true Fatty acids. 172.860 Section 172.860 Food and Drugs... Multipurpose Additives § 172.860 Fatty acids. The food additive fatty acids may be safely used in food and in the...

2010-04-01

185

Histidine-41 of the cytochrome b5 domain of the borage delta6 fatty acid desaturase is essential for enzyme activity.  

PubMed

Unlike most other plant microsomal desaturases, the Delta6-fatty acid desaturase from borage (Borago officinalis) contains an N-terminal extension that shows homology to the small hemoprotein cytochrome (Cyt) b5. To determine if this domain serves as a functional electron donor for the Delta6-fatty acid desaturase, mutagenesis and functional analysis by expression in transgenic Arabidopsis was carried out. Although expression of the wild-type borage Delta6-fatty acid desaturase resulted in the synthesis and accumulation of Delta6-unsaturated fatty acids, this was not observed in plants transformed with N-terminally deleted forms of the desaturase. Site-directed mutagenesis was used to disrupt one of the axial heme-binding residues (histidine-41) of the Cyt b5 domain; expression of this mutant form of the Delta6-desaturase in transgenic plants failed to produce Delta6-unsaturated fatty acids. These data indicate that the Cyt b5 domain of the borage Delta6-fatty acid desaturase is essential for enzymatic activity. PMID:10517856

Sayanova, O; Shewry, P R; Napier, J A

1999-10-01

186

Malonyl CoA control of fatty acid oxidation in the newborn heart in response to increased fatty acid supply.  

PubMed

The concentration of fatty acids in the blood or perfusate is a major determinant of the extent of myocardial fatty acid oxidation. Increasing fatty acid supply in adult rat increases myocardial fatty acid oxidation. Plasma levels of fatty acids increase post-surgery in infants undergoing cardiac bypass operation to correct congenital heart defects. How a newborn heart responds to increased fatty acid supply remains to be determined. In this study, we examined whether the tissue levels of malonyl CoA decrease to relieve the inhibition on carnitine palmitoyltransferase (CPT) I when the myocardium is exposed to higher concentrations of long-chain fatty acids in newborn rabbit heart. We then tested the contribution of the enzymes that regulate tissue levels of malonyl CoA, acetyl CoA carboxylase (ACC), and malonyl CoA decarboxylase (MCD). Our results showed that increasing fatty acid supply from 0.4 mmol/L (physiological) to 1.2 mmol/L (pathological) resulted in an increase in cardiac fatty acid oxidation rates and this was accompanied by a decrease in tissue malonyl CoA levels. The decrease in malonyl CoA was not related to any alterations in total and phosphorylated acetyl CoA carboxylase protein or the activities of acetyl CoA carboxylase and malonyl CoA decarboxylase. Our results suggest that the regulatory role of malonyl CoA remained when the hearts were exposed to high levels of fatty acids. PMID:17218986

Onay-Besikci, Arzu; Sambandam, Nandakumar

2006-11-01

187

Differences in the intramolecular structure of structured oils do not affect pancreatic lipase activity in vitro or the absorption by rats of (n-3) fatty acids.  

PubMed

The fatty acid composition and intramolecular structure of dietary triacylglycerols (TAGs) influence their absorption. We compared the in vitro pancreatic lipase activity and the lymphatic transport in rats of fish oil and 2 enzymatically interesterified oils containing 10:0 and (n-3) PUFAs of marine origin to investigate whether the positional distribution of fatty acids influenced the overall bioavailability of (n-3) PUFAs in the body. The structured oils had the (n-3) PUFA either mainly at the sn-1,3 position (LML, M = medium-chain fatty acid, L = long-chain fatty acid) or mainly at the sn-2 position (MLM). Oils were administered to lymph-cannulated rats and lymph was collected for 24 h. The fatty acid composition as well as the lipid class distribution of lymph samples was determined. In vitro pancreatic lipase activity was greater when fish oil was the substrate than when the structured oils were the substrates (P < 0.001 at 40 min). This was consistent with a greater 8-h recovery of total fatty acids from fish oil compared with the 2 structured oils (P < 0.05). The absorption profiles of MLM and LML in rats and their in vitro rates of lipase activity did not differ. This indicates that the absorption rate is highly influenced by the lipase activity, which in turn is affected by the fatty acid composition and intramolecular structure. The lipid class distribution in lymph collected from the 3 groups of rats did not differ. In conclusion, the intramolecular structure did not affect the overall absorption of (n-3) PUFAs. PMID:15987853

Porsgaard, Trine; Xu, Xuebing; Göttsche, Jesper; Mu, Huiling

2005-07-01

188

Mechanisms of Gene Regulation by Fatty Acids12  

PubMed Central

Consumption of specific dietary fatty acids has been shown to influence risk and progression of several chronic diseases, such as cardiovascular disease, obesity, cancer, and arthritis. In recent years, insights into the mechanisms underlying the biological effects of fatty acids have improved considerably and have provided the foundation for the emerging concept of fatty acid sensing, which can be interpreted as the property of fatty acids to influence biological processes by serving as signaling molecules. An important mechanism of fatty acid sensing is via stimulation or inhibition of DNA transcription. Here, we focus on fatty acid sensing via regulation of gene transcription and address the role of peroxisome proliferator–activated receptors, sterol regulatory element binding protein 1, Toll-like receptor 4, G protein–coupled receptors, and other putative mediators. PMID:22516720

Georgiadi, Anastasia; Kersten, Sander

2012-01-01

189

Activation of peroxisome proliferator-activated receptor-{alpha} (PPAR{alpha}) suppresses postprandial lipidemia through fatty acid oxidation in enterocytes  

SciTech Connect

Highlights: {yields} PPAR{alpha} activation increased mRNA expression levels of fatty acid oxidation-related genes in human intestinal epithelial Caco-2 cells. {yields} PPAR{alpha} activation also increased oxygen consumption rate and CO{sub 2} production and decreased secretion of triglyceride and ApoB from Caco-2 cells. {yields} Orally administration of bezafibrate increased mRNA expression levels of fatty acid oxidation-related genes and CO{sub 2} production in small intestinal epithelial cells. {yields} Treatment with bezafibrate decreased postprandial serum concentration of triglyceride after oral injection of olive oil in mice. {yields} It suggested that intestinal lipid metabolism regulated by PPAR{alpha} activation suppresses postprandial lipidemia. -- Abstract: Activation of peroxisome proliferator-activated receptor (PPAR)-{alpha} which regulates lipid metabolism in peripheral tissues such as the liver and skeletal muscle, decreases circulating lipid levels, thus improving hyperlipidemia under fasting conditions. Recently, postprandial serum lipid levels have been found to correlate more closely to cardiovascular diseases than fasting levels, although fasting hyperlipidemia is considered an important risk of cardiovascular diseases. However, the effect of PPAR{alpha} activation on postprandial lipidemia has not been clarified. In this study, we examined the effects of PPAR{alpha} activation in enterocytes on lipid secretion and postprandial lipidemia. In Caco-2 enterocytes, bezafibrate, a potent PPAR{alpha} agonist, increased mRNA expression levels of fatty acid oxidation-related genes, such as acyl-CoA oxidase, carnitine palmitoyl transferase, and acyl-CoA synthase, and oxygen consumption rate (OCR) and suppressed secretion levels of both triglycerides and apolipoprotein B into the basolateral side. In vivo experiments revealed that feeding high-fat-diet containing bezafibrate increased mRNA expression levels of fatty acid oxidation-related genes and production of CO{sub 2} and acid soluble metabolites in enterocytes. Moreover, bezafibrate treatment suppressed postprandial lipidemia after oral administration of olive oil to the mice. These findings indicate that PPAR{alpha} activation suppresses postprandial lipidemia through enhancement of fatty acid oxidation in enterocytes, suggesting that intestinal lipid metabolism regulated by PPAR{alpha} activity is a novel target of PPAR{alpha} agonist for decreasing circulating levels of lipids under postprandial conditions.

Kimura, Rino [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan); Takahashi, Nobuyuki, E-mail: nobu@kais.kyoto-u.ac.jp [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan); Murota, Kaeko [Department of Life Science, School of Science and Engineering, Kinki University, Osaka 770-8503 (Japan)] [Department of Life Science, School of Science and Engineering, Kinki University, Osaka 770-8503 (Japan); Yamada, Yuko [Laboratory of Physiological Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Physiological Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan); Niiya, Saori; Kanzaki, Noriyuki; Murakami, Yoko [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan); Moriyama, Tatsuya [Department of Applied Cell Biology, Graduate School of Agriculture, Kinki University, Nara 631-8505 (Japan)] [Department of Applied Cell Biology, Graduate School of Agriculture, Kinki University, Nara 631-8505 (Japan); Goto, Tsuyoshi; Kawada, Teruo [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)] [Laboratory of Molecular Function of Food, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Uji, Kyoto 611-0011 (Japan)

2011-06-24

190

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

191

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

192

Activation of the omega-3 fatty acid receptor GPR120 mediates anti-inflammatory actions in immortalized hypothalamic neurons  

PubMed Central

Background Overnutrition and the ensuing hypothalamic inflammation is a major perpetuating factor in the development of metabolic diseases, such as obesity and diabetes. Inflamed neurons of the CNS fail to properly regulate energy homeostasis leading to pathogenic changes in glucose handling, feeding, and body weight. Hypothalamic neurons are particularly sensitive to pro-inflammatory signals derived locally and peripherally, and it is these neurons that become inflamed first upon high fat feeding. Given the prevalence of metabolic disease, efforts are underway to identify therapeutic targets for this inflammatory state. At least in the periphery, omega-3 fatty acids and their receptor, G-protein coupled receptor 120 (GPR120), have emerged as putative targets. The role for GPR120 in the hypothalamus or CNS in general is poorly understood. Methods Here we introduce a novel, immortalized cell model derived from the rat hypothalamus, rHypoE-7, to study GPR120 activation at the level of the individual neuron. Gene expression levels of pro-inflammatory cytokines were studied by quantitative reverse transcriptase-PCR (qRT-PCR) upon exposure to tumor necrosis factor ? (TNF?) treatment in the presence or absence of the polyunsaturated omega-3 fatty acid docosahexaenoic acid (DHA). Signal transduction pathway involvement was also studied using phospho-specific antibodies to key proteins by western blot analysis. Results Importantly, rHypoE-7 cells exhibit a transcriptional and translational inflammatory response upon exposure to TNF? and express abundant levels of GPR120, which is functionally responsive to DHA. DHA pretreatment prevents the inflammatory state and this effect was inhibited by the reduction of endogenous GPR120 levels. GPR120 activates both AKT (protein kinase b) and ERK (extracellular signal-regulated kinase); however, the anti-inflammatory action of this omega-3 fatty acid (FA) receptor is AKT- and ERK-independent and likely involves the GPR120-transforming growth factor-?-activated kinase 1 binding protein (TAB1) interaction as identified in the periphery. Conclusions Taken together, GPR120 is functionally active in the hypothalamic neuronal line, rHypoE-7, wherein it mediates the anti-inflammatory actions of DHA to reduce the inflammatory response to TNF?. PMID:24674717

2014-01-01

193

Nitrated fatty acids: Synthesis and measurement  

PubMed Central

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

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

2012-01-01

194

Activation of PKN, a novel 120-kDa protein kinase with leucine zipper-like sequences, by unsaturated fatty acids and by limited proteolysis.  

PubMed

PKN, a novel protein kinase with catalytic domain homologous to PKC family and unique amino terminal leucine zipper-like sequences, was purified partially from COS7 cells transfected with the cDNA construct encoding human PKN for enzymatic characterization of the enzyme. Using serine containing synthetic peptides based on PKC pseudosubstrate sites as the phosphate acceptors, kinase activities estimated from partially purified PKN were not stimulated by Ca2+/phosphatidylserine/diolein but were activated several-fold to several tens-fold by 40 microM unsaturated fatty acids, such as arachidonic acid, linoleic acid, and oleic acid. Autophosphorylation of the immunoprecipitates using anti-PKN antiserum was also stimulated by various unsaturated fatty acids. Limited proteolysis of PKN with trypsin induced an enhancement of the peptide kinase activity that was almost independent of arachidonic acid. PMID:7945381

Mukai, H; Kitagawa, M; Shibata, H; Takanaga, H; Mori, K; Shimakawa, M; Miyahara, M; Hirao, K; Ono, Y

1994-10-14

195

Specific variations of fatty acid composition of Pseudomonas aeruginosa ATCC 15442 induced by quaternary ammonium compounds and relation with resistance to bactericidal activity.  

PubMed

The role of membrane fatty acid composition in the resistance of Pseudomonas aeruginosa ATCC 15442 to the bactericidal activity of Quaternary Ammonium Compounds (QACs) was investigated. The strain was grown in a medium with increasing concentrations of a QAC, benzyldimethyltetradecylammonium chloride (C14) and two non-QACs, sodium dichloroisocyanurate and tri-sodium phosphate. In the presence of C14 only, the strain was able to grow in concentrations higher than the minimal inhibitory concentration. As the strain adapted to C14, resistance to bactericidal activity of the same biocide increased. For the non-QACs, no change was noted when cells were grown in the presence of biocides. The C14-adapted cells showed variations in membrane fatty acid composition. A hierarchical clustering analysis was used to compare all fatty acid compositions of cultures in the presence, or not, of the three biocides used here and another QAC studied previously. The clusters obtained underlined specific variations of membrane fatty acids in response to the presence of QACs. Furthermore, with a simple linear regression analysis, a relationship was shown between the membrane fatty acids and the resistance developed by the strain against the bactericidal activity of C14. PMID:10594715

Guérin-Méchin, L; Dubois-Brissonnet, F; Heyd, B; Leveau, J Y

1999-11-01

196

Antiproliferative activity, mechanism of action and oral antitumor activity of CP4126, a fatty acid derivative of gemcitabine, in in vitro and in vivo tumor models  

Microsoft Academic Search

Summary  Gemcitabine is a deoxycytidine (dCyd) analog with activity in leukemia and solid tumors, which requires phosphorylation by\\u000a deoxycytidine kinase (dCK). Decreased membrane transport is a mechanism of resistance to gemcitabine. In order to facilitate\\u000a gemcitabine uptake and prolong retention in the cell, a lipophilic pro-drug was synthesized (CP-4126), with an elaidic fatty\\u000a acid esterified at the 5?position. CP-4126 was tested

Andries M. Bergman; Auke D. Adema; Jan Balzarini; Skjalg Bruheim; Iduna Fichtner; Paul Noordhuis; Øystein Fodstad; Finn Myhren; Marit L. Sandvold; Hans R. Hendriks; Godefridus J. Peters

2011-01-01

197

c-AMP dependent protein kinase A inhibitory activity of six algal extracts from southeastern Australia and their fatty acid composition.  

PubMed

c-AMP dependent protein kinase (protein kinase A, PKA) is an important enzyme involved in the regulation of an increasing number of physiological processes including immune function, cardiovascular disease, memory disorders and cancer. The objective of this study was to evaluate the PKA inhibitory activity of a range of algal extracts, along with their fatty acid composition. Six algal species were investigated including two Chlorophyta (Codium dimorphum and Ulva lactuca), two Phaeophyta (Phyllospora comosa and Sargassum sp.) and two Rhodophyta (Prionitis linearis and Corallina vancouveriensis), with the order of PKA inhibitory activity of their extracts identified as follows: brown seaweeds > red seaweeds > green seaweeds with the brown alga Sargassum sp. exhibiting the highest PKA inhibitory activity (84% at 100 microg/mL). GC/MS analysis identified a total of 18 fatty acids in the six algal extracts accounting for 72-87% of each extract, with hexadecanoic acid and 9,12-octadecadienoic acid as the dominant components. The most active extract (Sargassum sp.) also contained the highest percentage of the saturated C14:0 fatty acid (12.8% of the total extract), which is a known to inhibit PKA. These results provide the first description of the PKA inhibitory activity of marine algae along with the first description of the fatty acid composition of these six algal species from South Eastern Australian waters. Importantly, this study reveals that abundant and readily available marine algae are a new and relatively unexplored source of PKA inhibitory compounds. PMID:22908583

Zivanovic, Ana; Skropeta, Danielle

2012-07-01

198

Triiodothyronine Activates Lactate Oxidation Without Impairing Fatty Acid Oxidation and Improves Weaning From Extracorporeal Membrane Oxygenation.  

PubMed

Background:Extracorporeal membrane oxygenation (ECMO) provides a rescue for children with severe cardiac failure. It has previously been shown that triiodothyronine (T3) improves cardiac function by modulating pyruvate oxidation during weaning. This study focused on fatty acid (FA) metabolism modulated by T3 for weaning from ECMO after cardiac injury.Methods?and?Results:Nineteen immature piglets (9.1-15.3 kg) were separated into 3 groups with ECMO (6.5 h) and wean: normal circulation (Group-C); transient coronary occlusion (10 min) for ischemia-reperfusion (IR) followed by ECMO (Group-IR); and IR with T3 supplementation (Group-IR-T3). 13-Carbon ((13)C)-labeled lactate, medium-chain and long-chain FAs, was infused as oxidative substrates. Substrate fractional contribution (FC) to the citric acid cycle was analyzed by(13)C-nuclear magnetic resonance. ECMO depressed circulating T3 levels to 40% of the baseline at 4 h and were restored in Group-IR-T3. Group-IR decreased cardiac power, which was not fully restorable and 2 pigs were lost because of weaning failure. Group-IR also depressed FC-lactate, while the excellent contractile function and energy efficiency in Group-IR-T3 occurred along with a marked FC-lactate increase and [adenosine triphosphate]/[adenosine diphosphate] without either decreasing FC-FAs or elevating myocardial oxygen consumption over Group-C or -IR.Conclusions:T3 releases inhibition of lactate oxidation following IR injury without impairing FA oxidation. These findings indicate that T3 depression during ECMO is maladaptive, and that restoring levels improves metabolic flux and enhances contractile function during weaning. PMID:25354460

Kajimoto, Masaki; Ledee, Dolena R; Xu, Chun; Kajimoto, Hidemi; Isern, Nancy G; Portman, Michael A

2014-10-28

199

Plant fatty acid hydroxylase  

SciTech Connect

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

Somerville, C.; Loo, F. van de

2000-02-22

200

Plant fatty acid hydroxylase  

DOEpatents

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

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

2000-01-01

201

Human Cytomegalovirus Induces the Activity and Expression of Acetyl-Coenzyme A Carboxylase, a Fatty Acid Biosynthetic Enzyme Whose Inhibition Attenuates Viral Replication?†  

PubMed Central

We have previously reported that human cytomegalovirus (HCMV) infection induces large-scale changes to host cell glycolytic, nucleic acid, and phospholipid metabolism. Here we explore the viral mechanisms involved in fatty acid biosynthetic activation. Our results indicate that HCMV targets ACC1, the rate-limiting enzyme of fatty acid biosynthesis, through multiple mechanisms. HCMV infection was found to activate ACC1 expression, increasing the abundance of both ACC1 mRNA and protein. Viral gene expression but not viral DNA replication was found to be necessary for HCMV-mediated induction of ACC1 levels. HCMV infection was also found to increase the proteolytic processing of SREBP-2, a transcription factor whose proteolytic cleavage is known to activate a variety of phospholipid metabolic genes. Processing of SREBP-2 was found to be dependent on mTOR activity; pharmaceutical inhibition of mTOR blocked HCMV-induced SREBP-2 processing and prevented the induction of fatty acid biosynthesis and ACC1 expression. Independent of the increases in ACC1 expression, HCMV infection also induced ACC1's enzymatic activity. Inhibition of ACC1 through either RNA interference (RNAi) or inhibitor treatment was found to attenuate HCMV replication, and HCMV replication was sensitive to ACC1 inhibition even at the later stages of infection, suggesting a late role for fatty acid biosynthesis during HCMV replication. These findings indicate that HCMV infection actively modulates numerous functional aspects of a key metabolic regulatory enzyme that is important for high-titer viral replication. PMID:21471234

Spencer, Cody M.; Schafer, Xenia L.; Moorman, Nathaniel J.; Munger, Joshua

2011-01-01

202

Chemical composition of fatty acid and unsaponifiable fractions of leaves, stems and roots of Arbutus unedo and in vitro antimicrobial activity of unsaponifiable extracts.  

PubMed

The chemical composition of the fatty acid and unsaponifiable fractions of the leaves, stems and roots of Arbutus unedo L. were determined using gas chromatography and gas chromatography-mass spectrometry. The fatty acid fractions of the leaves, stems and roots contained 38.5%, 31.3% and 14.1% palmitic acid, respectively, along with other long-chain fatty acids (up to C22). The chemical composition of the unsaponifiable fractions differed: the leaf and stem fractions contained high levels of aliphatic (32.1% and 62.6%, respectively) and terpenic compounds (49.6% and 25.7%, respectively), and the root fraction mainly contained esters, of which the most abundant was benzyl cinnamate (36.6%). The antimicrobial activities of the unsaponifiable fractions against nine species of microorganisms were assessed. The unsaponifiable leaf and stem extracts inhibited the growth of Klebsiella pneumoniae, Enterococcus faecalis and Candida albicans. PMID:20734946

Diba, Mohamed Amine; Paolini, Julien; Bendahou, Mourad; Varesi, Laurent; Allali, Hocine; Desjobert, Jean-Marie; Tabti, Boufeldja; Costa, Jean

2010-07-01

203

Increased Long Chain acyl-Coa Synthetase Activity and Fatty Acid Import Is Linked to Membrane Synthesis for Development of Picornavirus Replication Organelles  

PubMed Central

All positive strand (+RNA) viruses of eukaryotes replicate their genomes in association with membranes. The mechanisms of membrane remodeling in infected cells represent attractive targets for designing future therapeutics, but our understanding of this process is very limited. Elements of autophagy and/or the secretory pathway were proposed to be hijacked for building of picornavirus replication organelles. However, even closely related viruses differ significantly in their requirements for components of these pathways. We demonstrate here that infection with diverse picornaviruses rapidly activates import of long chain fatty acids. While in non-infected cells the imported fatty acids are channeled to lipid droplets, in infected cells the synthesis of neutral lipids is shut down and the fatty acids are utilized in highly up-regulated phosphatidylcholine synthesis. Thus the replication organelles are likely built from de novo synthesized membrane material, rather than from the remodeled pre-existing membranes. We show that activation of fatty acid import is linked to the up-regulation of cellular long chain acyl-CoA synthetase activity and identify the long chain acyl-CoA syntheatse3 (Acsl3) as a novel host factor required for polio replication. Poliovirus protein 2A is required to trigger the activation of import of fatty acids independent of its protease activity. Shift in fatty acid import preferences by infected cells results in synthesis of phosphatidylcholines different from those in uninfected cells, arguing that the viral replication organelles possess unique properties compared to the pre-existing membranes. Our data show how poliovirus can change the overall cellular membrane homeostasis by targeting one critical process. They explain earlier observations of increased phospholipid synthesis in infected cells and suggest a simple model of the structural development of the membranous scaffold of replication complexes of picorna-like viruses, that may be relevant for other (+)RNA viruses as well. PMID:23762027

Scott, Alison J.; Ford, Lauren A.; Pei, Zhengtong; Watkins, Paul A.; Ernst, Robert K.; Belov, George A.

2013-01-01

204

Activation and repression of Epstein-Barr Virus and Kaposi's sarcoma-associated herpesvirus lytic cycles by short- and medium-chain fatty acids.  

PubMed

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; Miller, George

2014-07-01

205

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

206

Activation of cholesterol synthesis in preference to fatty acid synthesis in liver and adipose tissue of transgenic mice overproducing sterol regulatory element-binding protein-2.  

PubMed Central

We produced transgenic mice that express a dominant-positive truncated form of sterol regulatory element-binding protein-2 (SREBP-2) in liver and adipose tissue. The encoded protein lacks the membrane-binding and COOH-terminal regulatory domains, and it is therefore not susceptible to negative regulation by cholesterol. Livers from the transgenic mice showed increases in mRNAs encoding multiple enzymes of cholesterol biosynthesis, the LDL receptor, and fatty acid biosynthesis. The elevations in mRNA for 3-hydroxy-3-methylglutaryl coenzyme A (HMG CoA) synthase and HMG CoA reductase were especially marked (13-fold and 75-fold, respectively). As a result, the transgenic livers showed a 28-fold increase in the rate of cholesterol synthesis and a lesser fourfold increase in fatty acid synthesis, as measured by intraperitoneal injection of [3H]water. These results contrast with previously reported effects of dominant-positive SREBP-1a, which activated fatty acid synthesis more than cholesterol synthesis. In adipose tissue of the SREBP-2 transgenics, the mRNAs for cholesterol biosynthetic enzymes were elevated, but the mRNAs for fatty acid biosynthetic enzymes were not. We conclude that SREBP-2 is a relatively selective activator of cholesterol synthesis, as opposed to fatty acid synthesis, in liver and adipose tissue of mice. PMID:9616204

Horton, J D; Shimomura, I; Brown, M S; Hammer, R E; Goldstein, J L; Shimano, H

1998-01-01

207

Changes in fatty acids metabolism during differentiation of Atlantic salmon preadipocytes; Effects of n-3 and n-9 fatty acids  

Microsoft Academic Search

Atlantic salmon (Salmo salar) preadipocytes, isolated from visceral adipose tissue, differentiate from an unspecialized fibroblast like cell type to mature adipocytes filled with lipid droplets in culture. The expression of the adipogenic gene markers peroxisome proliferated activated receptor (PPAR) ?, lipoprotein lipase (LPL), microsomal triglyceride transfer protein (MTP), fatty acid transport protein (FATP) 1 and fatty acid binding protein (FABP)

Marijana Todor?evi?; Anne Vegusdal; Tor Gjøen; Hilde Sundvold; Bente E. Torstensen; Marte A. Kjær; Bente Ruyter

2008-01-01

208

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

209

N-3 polyunsaturated fatty acids suppress insulin-induced SREBP-1c transcription via reduced trans-activating capacity of LXRalpha.  

PubMed

Insulin coordinately up-regulates lipogenic gene transcription via induction of sterol regulatory element binding protein-1c (SREBP-1c). Conversely, polyunsaturated fatty acids (PUFA) decrease lipogenic gene transcription via suppression of SREBP-1c. We therefore examined the ability of n-3 PUFA to mitigate induction of SREBP-1c and its downstream lipogenic targets by insulin in primary rat hepatocyte cultures. Insulin induced expression of SREBP-1c mRNA 5-6 fold as well as rat SREBP-1c promoter activity. These effects were prevented by the n-3 fatty acids eicosapentaenoic acid (20:5 n-3; EPA) and docosahexaenoic acid (22:6 n-3, DHA), but not by the monounsaturated fatty acid oleic acid (18:1 n-6, OLA). N-3 fatty acids also effectively prevented insulin induction of the downstream lipogenic enzyme targets fatty acid synthase (FAS) and acetyl carboxyl coenzyme acetyltransferase-1 (ACC-1), and reduced de novo lipogenesis. The SREBP-1c promoter contains an insulin response unit consisting of tandem LXRalpha response elements (LXREs) as well as sites for NF-Y, Sp1, and SREBP-1c itself. The LXREs were identified as a primary site mediating suppression of SREBP-1c transcription by n-3 PUFA. DHA effectively prevented LXRalpha-dependent activation of both the wild type SREBP-1c promoter and the synthetic LXRE-driven promoter, and significantly blunted LXRalpha-dependent activation of a Gal4-LXRalpha chimeric protein thus demonstrating that n-3 PUFA effectively mitigate induction of SREBP-1c by insulin via reduced trans-activation of LXRalpha. PMID:19716432

Howell, George; Deng, Xiong; Yellaturu, Chandrahassa; Park, Edwards A; Wilcox, Henry G; Raghow, Rajendra; Elam, Marshall B

2009-12-01

210

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

211

Genistein stimulates fatty acid oxidation in a leptin receptor-independent manner through the JAK2-mediated phosphorylation and activation of AMPK in skeletal muscle.  

PubMed

Obesity is a public health problem that contributes to the development of insulin resistance, which is associated with an excessive accumulation of lipids in skeletal muscle tissue. There is evidence that soy protein can decrease the ectopic accumulation of lipids and improves insulin sensitivity; however, it is unknown whether soy isoflavones, particularly genistein, can stimulate fatty acid oxidation in the skeletal muscle. Thus, we studied the mechanism by which genistein stimulates fatty acid oxidation in the skeletal muscle. We showed that genistein induced the expression of genes of fatty acid oxidation in the skeletal muscle of Zucker fa/fa rats and in leptin receptor (ObR)-silenced C2C12 myotubes through AMPK phosphorylation. Furthermore, the genistein-mediated AMPK phosphorylation occurred via JAK2, which was possibly activated through a mechanism that involved cAMP. Additionally, the genistein-mediated induction of fatty acid oxidation genes involved PGC1? and PPAR?. As a result, we observed that genistein increased fatty acid oxidation in both the control and silenced C2C12 myotubes, as well as a decrease in the RER in mice, suggesting that genistein can be used in strategies to decrease lipid accumulation in the skeletal muscle. PMID:24013029

Palacios-González, Berenice; Zarain-Herzberg, Angel; Flores-Galicia, Isabel; Noriega, Lilia G; Alemán-Escondrillas, Gabriela; Zariñan, Teresa; Ulloa-Aguirre, Alfredo; Torres, Nimbe; Tovar, Armando R

2014-01-01

212

Saturated Fatty Acid Requirer of Neurospora crassa  

PubMed Central

Dietary saturated fatty acids containing 12- to 18-carbon atoms satisfy growth requirements of Neurospora crassa mutant cel (previously named ol; Perkins et al., reference 11); unsaturated fatty acids are synthesized by direct desaturation when an appropriate saturate is available. Odd-chain saturates, 15 carbons and 17 carbons long, satisfy the requirement, and elaidic acid (18:1 ?9trans) results in slow growth. Oleic acid and other cis-unsaturated fatty acids do not satisfy growth requirements; however, oleic acid plus elaidic acid result in growth at a faster rate than elaidate alone. The use of a spin-label fatty acid reveals that hyphae produced by cel during a slow basal level of growth have lipids that reflect a relatively rigid state of viscosity compared to wild type. cel Supplemented with fatty acids and wild type supplemented in the same way have lipids of the same viscosities as reflected by electron spin resonance. PMID:4323964

Henry, Susan A.; Keith, Alec D.

1971-01-01

213

Serum phospholipid monounsaturated fatty acid composition and ?-9-desaturase activity are associated with early alteration of fasting glycemic status.  

PubMed

Because alterations in blood fatty acid (FA) composition by dietary lipids are associated with insulin resistance and related metabolic disorders, we hypothesized that serum phospholipid FA composition would reflect the early alteration of fasting glycemic status, even in people without metabolic syndrome (MetS). To examine this hypothesis, serum phospholipid FA, desaturase activities, fasting glycemic status, and cardiometabolic parameters were measured in study participants (n = 1022; 30-69 years; male, n = 527; female, n = 495; nondiabetics without disease) who were stratified into normal fasting glucose (NFG) and impaired fasting glucose (IFG) groups. Total monounsaturated FA (MUFA), oleic acid (OA; 18:1n-9), dihomo-?-linolenic acid (DGLA; 20:3n-6), ?-9-desaturase activity (D9D; 18:1n-9/18:0), and DGLA/linoleic acid (20:3n-6/18:2n-6) in serum phospholipids were significantly higher in IFG subjects than NFG controls. Study subjects were subdivided into 4 groups, based on fasting glucose levels and MetS status. Palmitoleic acid (16:1n-7) was highest in IFG-MetS and lowest in NFG-non-MetS subjects. Oleic acid and D9D were higher in IFG-MetS than in the other 3 groups. Dihomo-?-linolenic acid and DGLA/linoleic acid were higher in MetS than in non-MetS, regardless of fasting glucose levels. The high-sensitivity C-reactive proteins (hs-CRPs) and 8-epi-prostaglandin-F2? were higher in IFG than in NFG, regardless of MetS status. Oxidized low-density lipoproteins were higher in IFG-MetS than in the other 3 groups. Total MUFAs, OA, and D9D were positively correlated with homeostasis model assessment of insulin resistance, fasting glucose, triglyceride, hs-CRP, and 8-epi-prostaglandin-F2?. Palmitoleic acid was positively correlated with triglyceride and hs-CRP. Lastly, total MUFA, OA, palmitoleic acid, and D9D were associated with early alteration of fasting glycemic status, therefore suggesting that these may be useful markers for predicting the risk of type 2 diabetes and cardiometabolic diseases. PMID:25236425

Cho, Jae Sun; Baek, Seung Han; Kim, Ji Young; Lee, Jong Ho; Kim, Oh Yoen

2014-09-01

214

Modulation of Nitro-fatty Acid Signaling  

PubMed Central

Inflammation, characterized by the activation of both resident and infiltrated immune cells, is accompanied by increased production of oxidizing and nitrating species. Nitrogen dioxide, the proximal nitrating species formed under these conditions, reacts with unsaturated fatty acids to yield nitroalkene derivatives. These electrophilic products modulate protein function via post-translational modification of susceptible nucleophilic amino acids. Nitroalkenes react with Keap1 to instigate Nrf2 signaling, activate heat shock response gene expression, and inhibit NF-?B-mediated signaling, inducing net anti-inflammatory and tissue-protective metabolic responses. We report the purification and characterization of a NADPH-dependent liver enzyme that reduces the nitroalkene moiety of nitro-oleic acid, yielding the inactive product nitro-stearic acid. Prostaglandin reductase-1 (PtGR-1) was identified as a nitroalkene reductase by protein purification and proteomic studies. Kinetic measurements, inhibition studies, immunological and molecular biology approaches as well as clinical analyses confirmed this identification. Overexpression of PtGR-1 in HEK293T cells promoted nitroalkene metabolism to inactive nitroalkanes, an effect that abrogated the Nrf2-dependent induction of heme oxygenase-1 expression by nitro-oleic acid. These results situate PtGR-1 as a critical modulator of both the steady state levels and signaling activities of fatty acid nitroalkenes in vivo. PMID:23878198

Vitturi, Dario A.; Chen, Chen-Shan; Woodcock, Steven R.; Salvatore, Sonia R.; Bonacci, Gustavo; Koenitzer, Jeffrey R.; Stewart, Nicolas A.; Wakabayashi, Nobunao; Kensler, Thomas W.; Freeman, Bruce A.; Schopfer, Francisco J.

2013-01-01

215

The Effects of Omega-3 Fatty Acid on Vitamin D Activation in Hemodialysis Patients: A Pilot Study  

PubMed Central

The high incidence of cardiovascular disease and vitamin D deficiency in chronic kidney disease patients is well known. Vitamin D activation by omega-3 fatty acid (FA) supplementation may explain the cardioprotective effects exerted by omega-3 FA. We hypothesized that omega-3 FA and 25-hydroxyvitamin D (25(OH)D) supplementation may increase 1,25-dihydroxyvitamin D (1,25(OH)2D) levels compared to 25(OH)D supplementation alone in hemodialysis (HD) patients that have insufficient or deficient 25(OH)D levels. We enrolled patients that were treated for at least six months with 25(OH)D < 30 ng/mL (NCT01596842). Patients were randomized to treatment for 12 weeks with cholecalciferol supplemented with omega-3 FA or a placebo. Levels of 25(OH)D and 1,25(OH)2D were measured after 12 weeks. The erythrocyte membrane FA contents were also measured. Levels of 25(OH)D were increased in both groups at 12 weeks compared to baseline. The 1,25(OH)2D levels at 12 weeks compared to baseline showed a tendency to increase in the omega-3 FA group. The oleic acid and monounsaturated FA content decreased, while the omega-3 index increased in the omega-3 FA group. Omega-3 FA supplementation may be partly associated with vitamin D activation, although increased 25(OH)D levels caused by short-term cholecalciferol supplementation were not associated with vitamin D activation in HD patients. PMID:25636157

Lee, Su Mi; Son, Young Ki; Kim, Seong Eun; An, Won Suk

2015-01-01

216

Pharmacologically relevant receptor binding characteristics and 5alpha-reductase inhibitory activity of free Fatty acids contained in saw palmetto extract.  

PubMed

Saw palmetto extract (SPE), used widely for the treatment of benign prostatic hyperplasia (BPH) has been shown to bind alpha(1)-adrenergic, muscarinic and 1,4-dihydropyridine (1,4-DHP) calcium channel antagonist receptors. Major constituents of SPE are lauric acid, oleic acid, myristic acid, palmitic acid and linoleic acid. The aim of this study was to investigate binding affinities of these fatty acids for pharmacologically relevant (alpha(1)-adrenergic, muscarinic and 1,4-DHP) receptors. The fatty acids inhibited specific [(3)H]prazosin binding in rat brain in a concentration-dependent manner with IC(50) values of 23.8 to 136 microg/ml, and specific (+)-[(3)H]PN 200-110 binding with IC(50) values of 24.5 to 79.5 microg/ml. Also, lauric acid, oleic acid, myristic acid and linoleic acid inhibited specific [(3)H]N-methylscopolamine ([(3)H]NMS) binding in rat brain with IC(50) values of 56.4 to 169 microg/ml. Palmitic acid had no effect on specific [(3)H]NMS binding. The affinity of oleic acid, myristic acid and linoleic acid for each receptor was greater than the affinity of SPE. Scatchard analysis revealed that oleic acid and lauric acid caused a significant decrease in the maximal number of binding sites (B(max)) for [(3)H]prazosin, [(3)H]NMS and (+)-[(3)H]PN 200-110. The results suggest that lauric acid and oleic acid bind noncompetitively to alpha(1)-adrenergic, muscarinic and 1,4-DHP calcium channel antagonist receptors. We developed a novel and convenient method of determining 5alpha-reductase activity using LC/MS. With this method, SPE was shown to inhibit 5alpha-reductase activity in rat liver with an IC(50) of 101 microg/ml. Similarly, all the fatty acids except palmitic acid inhibited 5alpha-reductase activity, with IC(50) values of 42.1 to 67.6 microg/ml. In conclusion, lauric acid, oleic acid, myristic acid, and linoleic acid, major constituents of SPE, exerted binding activities of alpha(1)-adrenergic, muscarinic and 1,4-DHP receptors and inhibited 5alpha-reductase activity. PMID:19336899

Abe, Masayuki; Ito, Yoshihiko; Oyunzul, Luvsandorj; Oki-Fujino, Tomomi; Yamada, Shizuo

2009-04-01

217

Structural requirements for charged lipid molecules to directly increase or suppress K+ channel activity in smooth muscle cells. Effects of fatty acids, lysophosphatidate, acyl coenzyme A and sphingosine  

PubMed Central

We determined the structural features necessary for fatty acids to exert their action on K+ channels of gastric smooth muscle cells. Examination of the effects of a variety of synthetic and naturally occurring lipid compounds on K+ channel activity in cell-attached and excised membrane patches revealed that negatively charged analogs of medium to long chain fatty acids (but not short chain analogs) as well as certain other negatively charged lipids activate the channels. In contrast, positively charged, medium to long chain analogs suppress activity, and neutral analogs are without effect. The key requirements for effective compounds seem to be a sufficiently hydrophobic domain and the presence of a charged group. Furthermore, those negatively charged compounds unable to "flip" across the bilayer are effective only when applied at the cytosolic surface of the membrane, suggesting that the site of fatty acid action is also located there. Finally, because some of the effective compounds, for example, the fatty acids themselves, lysophosphatidate, acyl Coenzyme A, and sphingosine, are naturally occurring substances and can be liberated by agonist- activated or metabolic enzymes, they may act as second messengers targeting ion channels. PMID:8195783

1994-01-01

218

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...

219

Dietary (n-6) Polyunsaturated Fatty Acids Affect ß-AdrenergicReceptor Binding and Adenylate Cyclase Activity in Pig Adipocyte Plasma Membrane1  

Microsoft Academic Search

The effect of dietary (n-6) polyunsaturated fatty acids (sunflower oil) on pig adipocyte ß- adrenoreceptor and adenylate cyclase activity was ex amined. Two adipose sites (subcutaneous and perirenal) were compared. The existence of two affinity classes for ß-adrenoreceptorswas evidenced. Adenylate cyclase stimulation by isoproterenol was higher in the perirenal fat than in the subcutaneous fat, in parallel to a higher

CHRISTINE NICOLAS; DANIELE LACASA; YVES DEMARNE; BRIGITTE AGLI

220

Use of agar diffusion assay to evaluate bactericidal activity of formulations of alkaline salts of fatty acids against bacteria associated with poultry processing  

Technology Transfer Automated Retrieval System (TEKTRAN)

The agar diffusion assay was used to examine antibacterial activity of alkaline salts of fatty acids (FA). Wells in agar media seeded with bacteria were filled with FA-potassium hydroxide (KOH) solutions, plates were incubated, and zones of inhibition were measured. The relationship between bacteric...

221

The Fatty Acid Content of Ocean Water  

E-print Network

1-10% major 10% 32 assumed that the reduction in unsaturation and chain length is due to prolonged exposure of fatty acids to oxidizing conditions in deep water, then this might indicate sufficiently rapid mixing rates of top and bottom water... and unsaturated fatty acids and triglycerides during this investigation gave similar results. 13 Final acceptance of gas-liquid chromatography as a method for identifying fatty acids in sea water was based upon the results obtained from repeated analysis...

Slowey, James Frank

1960-01-01

222

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

223

Docosahexaenoic acid and n-6 docosapentaenoic acid supplementation alter rat skeletal muscle fatty acid composition  

Microsoft Academic Search

BACKGROUND: Docosahexaenoic acid (22:6n-3, DHA) and n-6 docosapentaenoic acid (22:5n-6, DPAn-6) are highly unsaturated fatty acids (HUFA, ? 20 carbons, ? 3 double bonds) that differ by a single carbon-carbon double bond at the ?19 position. Membrane 22:6n-3 may support skeletal muscle function through optimal ion pump activity of sarcoplasmic reticulum and electron transport in the mitochondria. Typically n-3 fatty

Ken D Stark; Sun-Young Lim; Norman Salem Jr

2007-01-01

224

Fatty acid composition of common dolphin blubber  

E-print Network

acids were greatest in the outer layer, while levels of saturated and polyunsaturated n-3 and n-6 fatty acids were greatest in the inner layer. In general, sexually mature animals showed a greater degree of fatty acid stratification than sexually...

Smith, Heather Rebecca

2002-01-01

225

Rosiglitazone Inhibits Acyl-CoA Synthetase Activity and Fatty Acid Partitioning to Diacylglycerol and Triacylglycerol via a Peroxisome Proliferator–Activated Receptor-?–Independent Mechanism in Human Arterial Smooth Muscle Cells and Macrophages  

PubMed Central

Rosiglitazone is an insulin-sensitizing agent that has recently been shown to exert beneficial effects on atherosclerosis. In addition to peroxisome proliferator–activated receptor (PPAR)-?, rosiglitazone can affect other targets, such as directly inhibiting recombinant long-chain acyl-CoA synthetase (ACSL)-4 activity. Because it is unknown if ACSL4 is expressed in vascular cells involved in atherosclerosis, we investigated the ability of rosiglitazone to inhibit ACSL activity and fatty acid partitioning in human and murine arterial smooth muscle cells (SMCs) and macrophages. Human and murine SMCs and human macrophages expressed Acsl4, and rosiglitazone inhibited Acsl activity in these cells. Furthermore, rosiglitazone acutely inhibited partitioning of fatty acids into phospholipids in human SMCs and inhibited fatty acid partitioning into diacylglycerol and triacylglycerol in human SMCs and macrophages through a PPAR-?–independent mechanism. Conversely, murine macrophages did not express ACSL4, and rosiglitazone did not inhibit ACSL activity in these cells, nor did it affect acute fatty acid partitioning into cellular lipids. Thus, rosiglitazone inhibits ACSL activity and fatty acid partitioning in human and murine SMCs and in human macrophages through a PPAR-?–independent mechanism likely to be mediated by ACSL4 inhibition. Therefore, rosiglitazone might alter the biological effects of fatty acids in these cells and in atherosclerosis. PMID:17259370

Askari, Bardia; Kanter, Jenny E.; Sherrid, Ashley M.; Golej, Deidre L.; Bender, Andrew T.; Liu, Joey; Hsueh, Willa A.; Beavo, Joseph A.; Coleman, Rosalind A.; Bornfeldt, Karin E.

2010-01-01

226

Hypothalamic GPR40 Signaling Activated by Free Long Chain Fatty Acids Suppresses CFA-Induced Inflammatory Chronic Pain  

PubMed Central

GPR40 has been reported to be activated by long-chain fatty acids, such as docosahexaenoic acid (DHA). However, reports studying functional role of GPR40 in the brain are lacking. The present study focused on the relationship between pain regulation and GPR40, investigating the functional roles of hypothalamic GPR40 during chronic pain caused using a complete Freund's adjuvant (CFA)-induced inflammatory chronic pain mouse model. GPR40 protein expression in the hypothalamus was transiently increased at day 7, but not at days 1, 3 and 14, after CFA injection. GPR40 was co-localized with NeuN, a neuron marker, but not with glial fibrillary acidic protein (GFAP), an astrocyte marker. At day 1 after CFA injection, GFAP protein expression was markedly increased in the hypothalamus. These increases were significantly inhibited by the intracerebroventricular injection of flavopiridol (15 nmol), a cyclin-dependent kinase inhibitor, depending on the decreases in both the increment of GPR40 protein expression and the induction of mechanical allodynia and thermal hyperalgesia at day 7 after CFA injection. Furthermore, the level of DHA in the hypothalamus tissue was significantly increased in a flavopiridol reversible manner at day 1, but not at day 7, after CFA injection. The intracerebroventricular injection of DHA (50 µg) and GW9508 (1.0 µg), a GPR40-selective agonist, significantly reduced mechanical allodynia and thermal hyperalgesia at day 7, but not at day 1, after CFA injection. These effects were inhibited by intracerebroventricular pretreatment with GW1100 (10 µg), a GPR40 antagonist. The protein expression of GPR40 was colocalized with that of ?-endorphin and proopiomelanocortin, and a single intracerebroventricular injection of GW9508 (1.0 µg) significantly increased the number of neurons double-stained for c-Fos and proopiomelanocortin in the arcuate nucleus of the hypothalamus. Our findings suggest that hypothalamic GPR40 activated by free long chain fatty acids might have an important role in this pain control system. PMID:24349089

Nakamoto, Kazuo; Nishinaka, Takashi; Sato, Naoya; Mankura, Mitsumasa; Koyama, Yutaka; Kasuya, Fumiyo; Tokuyama, Shogo

2013-01-01

227

Fatty Acids, Lipid Mediators, and T-Cell Function  

PubMed Central

Research toward the mechanisms underlying obesity-linked complications has intensified during the last years. As a consequence, it has become clear that metabolism and immunity are intimately linked. Free fatty acids and other lipids acquired in excess by current feeding patterns have been proposed to mediate this link due to their immune modulatory capacity. The functional differences between saturated and unsaturated fatty acids, in combination with their dietary intake are believed to modulate the outcome of immune responses. Moreover, unsaturated fatty acids can be oxidized in a tightly regulated and specific manner to generate either potent pro-inflammatory or pro-resolving lipid mediators. These oxidative derivatives of fatty acids have received detailed attention during the last years, as they have proven to have strong immune modulatory capacity, even in pM ranges. Both fatty acids and oxidized fatty acids have been studied especially in relation to macrophage and T-cells functions. In this review, we propose to focus on the effect of fatty acids and their oxidative derivatives on T-cells, as it is an active area of research during the past 5?years. The effect of fatty acids and their derivatives on activation and proliferation of T-cells, as well as the delicate balance between stimulation and lipotoxicity will be discussed. Moreover, the receptors involved in the interaction between free fatty acids and their derivatives with T-cells will be summarized. Finally, the mechanisms involved in modulation of T-cells by fatty acids will be addressed, including cellular signaling and metabolism of T-cells. The in vitro results will be placed in context of in vivo studies both in humans and mice. In this review, we summarize the latest findings on the immune modulatory function of lipids on T-cells and will point out novel directions for future research. PMID:25352844

de Jong, Anja J.; Kloppenburg, Margreet; Toes, René E. M.; Ioan-Facsinay, Andreea

2014-01-01

228

In vitro effects of temperature and salinity on fatty acid synthesis in the oyster protozoan parasite  

E-print Network

In vitro effects of temperature and salinity on fatty acid synthesis in the oyster protozoan on fatty acid synthetic activities in the oyster protozoan parasite, Perkinsus marinus, were tested; Oyster; Parasite; Perkinsus marinus; Protozoan; Salinity; Temperature 1. Introduction Perkinsus marinus

Hartley, Troy W.

229

METABOLITE SIGNALING; ROLE OF FATTY ACIDS IN PLANT DEFENSE  

Technology Transfer Automated Retrieval System (TEKTRAN)

Stearoyl-ACP-desaturase-mediated conversion of stearic acid (18:0) to oleic acid (18:1) is the key step regulating levels of unsaturated fatty acids (FAs) in the cell. A mutation in the ssi2 encoded S-ACP-DES results in constitutive activation of salicylic acid (SA) pathway and repression of certain...

230

Comparison of Bacillus monooxygenase genes for unique fatty acid production  

Technology Transfer Automated Retrieval System (TEKTRAN)

This paper reviews Bacillus genes encoding monooxygenase enzymes producing unique fatty acid metabolites. Specifically, it examines standard monooxygenase electron transfer schemes and related domain structures of these fused domain enzymes on route to understanding the observed oxygenase activiti...

231

Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids  

Microsoft Academic Search

Wine polyphenols were examined for their capacity to protect the lipid and protein moieties of porcine low density lipoproteins (LDL) during oxidation. The efficiency of resveratrol (3, 4?, 5, trihydroxystilbene) and defined flavonoids was compared to that of a wine extract (WE) containing 0.5 gg proanthocyanidols. The efficiency of resveratrol for protecting polyunsaturated fatty acids (PUFA) was higher than that

Lucie Frémont; Leila Belguendouz; Serge Delpal

1999-01-01

232

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

233

Antibacterial targets in fatty acid biosynthesis.  

PubMed

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

Wright, H Tonie; Reynolds, Kevin A

2007-10-01

234

Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids.  

PubMed

Wine polyphenols were examined for their capacity to protect the lipid and protein moieties of porcine low density lipoproteins (LDL) during oxidation. The efficiency of resveratrol (3, 4', 5, trihydroxystilbene) and defined flavonoids was compared to that of a wine extract (WE) containing 0.5 g/g proanthocyanidols. The efficiency of resveratrol for protecting polyunsaturated fatty acids (PUFA) was higher than that of flavonoids in copper-induced oxidation and lower in AAPH (radical initiator)-induced oxidation. The LDL receptor activity was evaluated by flow cytometry using LDL labeled with fluorescein isothiocyanate (FITC) and Chinese hamster ovary cells (CHO-K1). The incubation of CHO-K1 with FITC-LDL oxidized for 16 h reduced the proportion of fluorescent cells from 97% to 4%. At a concentration of 40 microM, resveratrol and flavonoids completely restored the uptake of copper-oxidized LDL and AAPH-oxidized LDL respectively. Total fluorescence could also be obtained with 20 mg/L of WE with both oxidation systems. These data are consistent with previous findings relative to the formation of degradative products from PUFA. They confirm that resveratrol was more effective than flavonoids as a chelator of copper and less effective as a free-radical scavenger. Moreover, they show that WE, which contained monomeric and oligomeric forms of flavonoids and phenolic acids, protected LDL by both mechanisms. PMID:10403511

Frémont, L; Belguendouz, L; Delpal, S

1999-01-01

235

Alkyl polyglucose enhancing propionic acid enriched short-chain fatty acids production during anaerobic treatment of waste activated sludge and mechanisms.  

PubMed

Adding alkyl polyglucose (APG) into an anaerobic treatment system of waste activated sludge (WAS) was reported to remarkably improve the production of short-chain fatty acids (SCFAs), especially propionic acid via simultaneously accelerating solubilization and hydrolysis, enhancing acidification, inhibiting methanogenesis and balancing carbon to nitrogen (C/N) ratio of substrate. Not only the production of SCFAs, especially propionic acid, was significantly improved by APG, but also the feasible operation time was shortened. The SCFAs yield at 0.3 g APG per gram of total suspended solids (TSS) within 4 d was 2988 ± 60 mg chemical oxygen demand (COD) per liter, much higher than that those from sole WAS or sole WAS plus sole APG. The corresponding yield of propionic acid was 1312 ± 25 mg COD/L, 7.9-fold of sole WAS. Mechanism investigation showed that during anaerobic treatment of WAS in the presence of APG both the solubilization and hydrolysis were accelerated and the acidification was enhanced, while the methanogenesis was inhibited. Moreover, the activities of key enzymes involved in WAS hydrolysis and acidification were improved through the adjustment of C/N ratio of substrates with APG. The abundance of microorganisms responsible for organic compounds hydrolysis and SCFAs production was also observed to be greatly enhanced with APG via 454 high-throughput pyrosequencing analysis. PMID:25697695

Luo, Jingyang; Feng, Leiyu; Chen, Yinguang; Sun, Han; Shen, Qiuting; Li, Xiang; Chen, Hong

2015-04-15

236

Fatty Acid Profile Including Trans Fatty Acid Content of Margarines Marketed in Mexico  

Microsoft Academic Search

In this study, the fatty acid profile of 42 margarines marketed in Mexico was identified and quantified including the total\\u000a trans fatty acids (TFA). The ratio of the sum of cholesterol-lowering fatty acids CLFA (cis-oleic, linoleic and ?-linolenic fatty acids) to the sum of cholesterol-raising fatty acids CRFA (C12:0, C14:0, C16:0, TFA)\\u000a and the ?6\\/?3 ratio were calculated to evaluate

Maylet Hernández-Martínez; Tzayhri Gallardo-Velázquez; Guillermo Osorio-Revilla

237

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

238

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

239

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

240

Genetics Home Reference: Fatty acid hydroxylase-associated neurodegeneration  

MedlinePLUS

... Recent literature OMIM Genetic disorder catalog Conditions > Fatty acid hydroxylase-associated neurodegeneration On this page: Description Genetic ... Glossary definitions Reviewed October 2012 What is fatty acid ... neurodegeneration? Fatty acid hydroxylase-associated neurodegeneration ( ...

241

75 FR 71556 - Polyoxyalkylated Glycerol Fatty Acid Esters; Tolerance Exemption  

Federal Register 2010, 2011, 2012, 2013, 2014

...FRL-8852-2] Polyoxyalkylated Glycerol Fatty Acid Esters; Tolerance Exemption AGENCY: Environmental...residues of polyoxyalkylated glycerol fatty acid esters; the mono-, di-, or triglyceride... 18 saturated and unsaturated, fatty acids containing up to 15% water by weight...

2010-11-24

242

N-3 polyunsaturated fatty acid regulation of hepatic gene transcription  

PubMed Central

Purpose of review The liver plays a central role in whole body lipid metabolism and adapts rapidly to changes in dietary fat composition. This adaption involves changes in the expression of genes involved in glycolysis, de-novo lipogenesis, fatty acid elongation, desaturation and oxidation. This review brings together metabolic and molecular studies that help explain n-3 (omega-3) polyunsaturated fatty acid regulation of hepatic gene transcription. Recent findings Dietary n-3 polyunsaturated fatty acid regulates hepatic gene expression by targeting three major transcriptional regulatory networks: peroxisome proliferator-activated receptor ?, sterol regulatory element binding protein-1 and the carbohydrate regulatory element binding protein/Max-like factor X heterodimer. 22 : 6,n-3, the most prominent n-3 polyunsaturated fatty acid in tissues, is a weak activator of peroxisome proliferator-activated receptor ?. Hepatic metabolism of 22 : 6,n-3, however, generates 20 : 5,n-3, a strong peroxisome proliferator-activated receptor ? activator. In contrast to peroxisome proliferator-activated receptor ?, 22 : 6,n-3 is the most potent fatty acid regulator of hepatic sterol regulatory element binding protein-1. 22 : 6,n-3 suppresses sterol regulatory element binding protein-1 gene expression while enhancing degradation of nuclear sterol regulatory element binding protein-1 through 26S proteasome and Erk1/2-dependent mechanisms. Both n-3 and n-6 polyunsaturated fatty acid suppress carbohydrate regulatory element binding protein and Max-like factor X nuclear abundance and interfere with glucose-regulated hepatic metabolism. Summary These studies have revealed unique mechanisms by which specific polyunsaturated fatty acids control peroxisome proliferator activated receptor ?, sterol regulatory element binding protein-1 and carbohydrate regulatory element binding protein/Max-like factor X function. As such, specific metabolic and signal transduction pathways contribute significantly to the fatty acid regulation of these transcription factors and their corresponding regulatory networks. PMID:18460914

Jump, Donald B.

2009-01-01

243

Cellular Fatty Acid Metabolism and Cancer  

PubMed Central

Cancer cells commonly have characteristic changes in metabolism. Cellular proliferation, a common feature of all cancers, requires fatty acids for synthesis of membranes and signaling molecules. Here, we provide a view of cancer cell metabolism from a lipid perspective, and we summarize evidence that limiting fatty acid availability can control cancer cell proliferation. PMID:23791484

Currie, Erin; Schulze, Almut; Zechner, Rudolf; Walther, Tobias C.; Farese, Robert V.

2013-01-01

244

Phylogenomic reconstruction of archaeal fatty acid metabolism  

PubMed Central

While certain archaea appear to synthesize and/or metabolize fatty acids, the respective pathways still remain obscure. By analyzing the genomic distribution of the key lipid-related enzymes, we were able to identify the likely components of the archaeal pathway of fatty acid metabolism, namely, a combination of the enzymes of bacterial-type ?-oxidation of fatty acids (acyl-CoA-dehydrogenase, enoyl-CoA hydratase, and 3-hydroxyacyl-CoA dehydrogenase) with paralogs of the archaeal acetyl-CoA C-acetyltransferase, an enzyme of the mevalonate biosynthesis pathway. These three ?-oxidation enzymes working in the reverse direction could potentially catalyze biosynthesis of fatty acids, with paralogs of acetyl-CoA C-acetyltransferase performing addition of C2 fragments. The presence in archaea of the genes for energy-transducing membrane enzyme complexes, such as cytochrome bc complex, cytochrome c oxidase, and diverse rhodopsins, was found to correlate with the presence of the proposed system of fatty acid biosynthesis. We speculate that because these membrane complexes functionally depend on fatty acid chains, their genes could have been acquired via lateral gene transfer from bacteria only by those archaea that already possessed a system of fatty acid biosynthesis. The proposed pathway of archaeal fatty acid metabolism operates in extreme conditions and therefore might be of interest in the context of biofuel production and other industrial applications. PMID:24818264

Dibrova, Daria V.; Galperin, Michael Y.; Mulkidjanian, Armen Y.

2014-01-01

245

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...

246

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

247

Dietary fat and the fatty acid composition of tissue lipids  

Microsoft Academic Search

Some characteristics of the fatty acid composition of animal tissue lipids are described and the origins of tissue fatty acids\\u000a are discussed briefly. The effect of dietary fat on composition of tissue lipids is discussed. Types of dietary fatty acids\\u000a for which experimental work is described include polyunsaturated fatty acids, short-chain fatty acids, fatty acids with chain\\u000a length greater than

K. K. Carroll

1965-01-01

248

Fatty acid components of larval Ostrea edulis (L.): importance of triacylglycerols as a fatty acid reserve.  

PubMed

1. The fatty acid profiles of all of the acyl-lipid classes of 1- and 10-day-old European oyster Ostrea edulis (L.) larvae were studied in detail by capillary gas-liquid chromatography. 2. No significant changes in the fatty acids were detected between the different larval stages. 3. Total lipid fatty acids showed a higher degree of unsaturation than previously reported. This may be a consequence of the extraction of lipids from the living tissues without sample storage. 4. One-third of the triacylglycerol fatty acids were polyunsaturated. In agreement with the importance of triacylglycerols in lipids of bivalve larvae, it is suggested that this lipid fraction may act as a temporary reservoir of physiologically-important polyunsaturated fatty acids. 5. Free fatty acids and fatty acids from the minor lipid classes are discussed in terms of their possible origin and physiological significances. PMID:3248373

Napolitano, G E; Ratnayake, W M; Ackman, R G

1988-01-01

249

Liver X Receptor Agonists Augment Human Islet Function through Activation of Anaplerotic Pathways and Glycerolipid/Free Fatty Acid Cycling*  

PubMed Central

Recent studies in rodent models suggest that liver X receptors (LXRs) may play an important role in the maintenance of glucose homeostasis and islet function. To date, however, no studies have comprehensively examined the role of LXRs in human islet biology. Human islets were isolated from non-diabetic donors and incubated in the presence or absence of two synthetic LXR agonists, TO-901317 and GW3965, under conditions of low and high glucose. LXR agonist treatment enhanced both basal and stimulated insulin secretion, which corresponded to an increase in the expression of genes involved in anaplerosis and reverse cholesterol transport. Furthermore, enzyme activity of pyruvate carboxylase, a key regulator of pyruvate cycling and anaplerotic flux, was also increased. Whereas LXR agonist treatment up-regulated known downstream targets involved in lipogenesis, we observed no increase in the accumulation of intra-islet triglyceride at the dose of agonist used in our study. Moreover, LXR activation increased expression of the genes encoding hormone-sensitive lipase and adipose triglyceride lipase, two enzymes involved in lipolysis and glycerolipid/free fatty acid cycling. Chronically, insulin gene expression was increased after treatment with TO-901317, and this was accompanied by increased Pdx-1 nuclear protein levels and enhanced Pdx-1 binding to the insulin promoter. In conclusion, our data suggest that LXR agonists have a direct effect on the islet to augment insulin secretion and expression, actions that should be considered either as therapeutic or unintended side effects, as these agents are developed for clinical use. PMID:20007976

Ogihara, Takeshi; Chuang, Jen-Chieh; Vestermark, George L.; Garmey, James C.; Ketchum, Robert J.; Huang, Xiaolun; Brayman, Kenneth L.; Thorner, Michael O.; Repa, Joyce J.; Mirmira, Raghavendra G.; Evans-Molina, Carmella

2010-01-01

250

Concurrent Physical Activity Modifies the Association between n3 Long-Chain Fatty Acids and Cardiometabolic Risk in Midlife Adults12  

PubMed Central

Greater consumption of n3 (?3) polyunsaturated fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) can reduce risk for cardiovascular disease events, yet their effects on metabolic risk factors and diabetes remain unclear. This cross-sectional study used a community volunteer sample to test whether the associations between n3 fatty acids and cardiometabolic risk vary as a function of physical activity. Participants were 344 generally healthy adults, 30–54 y of age, not taking fish oil supplements or confounding medications. Serum phospholipid EPA and DHA were used together (EPA+DHA) as a biomarker of n3 fatty acid exposure. Cardiometabolic risk was calculated as a continuous measure based on standardized distributions of blood pressure, waist circumference, HDL cholesterol, triglycerides, glucose, and a simple count of risk factors. Insulin resistance was estimated from the homeostatic model assessment. Physical activity was found to predict cardiometabolic risk (P ? 0.02) and insulin resistance (P ? 0.02) and to moderate the association between EPA+DHA and both cardiometabolic risk (P-interaction ? 0.02) and insulin resistance (P-interaction ? 0.02). Specifically, higher EPA+DHA was associated with lower cardiometabolic risk and insulin resistance in persons engaged in regular physical activity but not in relatively inactive individuals. These findings were noted in several components of cardiometabolic risk, in men and women separately, and in models adjusted for overall diet quality. In midlife adults, habitual physical activity may be necessary to unmask the salutary effects of n3 fatty acids on cardiometabolic risk and insulin resistance. PMID:23884386

Muldoon, Matthew F.; Erickson, Kirk I.; Goodpaster, Bret H.; Jakicic, John M.; Conklin, Sarah M.; Sekikawa, Akira; Yao, Jeffrey K.; Manuck, Stephen B.

2013-01-01

251

Cyanidin-3-O-?-glucoside regulates fatty acid metabolism via an AMP-activated protein kinase-dependent signaling pathway in human HepG2 cells  

PubMed Central

Background Hepatic metabolic derangements are key components in the development of fatty liver disease. AMP-activated protein kinase (AMPK) plays a central role in controlling hepatic lipid metabolism through modulating the downstream acetyl CoA carboxylase (ACC) and carnitine palmitoyl transferase 1 (CPT-1) pathway. In this study, cyanidin-3-O-?-glucoside (Cy-3-g), a typical anthocyanin pigment was used to examine its effects on AMPK activation and fatty acid metabolism in human HepG2 hepatocytes. Results Anthocyanin Cy-3-g increased cellular AMPK activity in a calmodulin kinase kinase dependent manner. Furthermore, Cy-3-g substantially induced AMPK downstream target ACC phosphorylation and inactivation, and then decreased malonyl CoA contents, leading to stimulation of CPT-1 expression and significant increase of fatty acid oxidation in HepG2 cells. These effects of Cy-3-g are largely abolished by pharmacological and genetic inhibition of AMPK. Conclusion This study demonstrates that Cy-3-g regulates hepatic lipid homeostasis via an AMPK-dependent signaling pathway. Targeting AMPK activation by anthocyanin may represent a promising approach for the prevention and treatment of obesity-related nonalcoholic fatty liver disease. PMID:22243683

2012-01-01

252

Fatty acid ethanolamides modulate CD36-mRNA through dietary fatty acid manipulation in Syrian Golden hamsters.  

PubMed

Fatty acids convert to fatty acid ethanolamides which associate with lipid signalling, fat oxidation, and energy balance; however, the extent to which dietary fatty acids manipulation can impact such control processes through fatty acid ethanolamides-related mechanisms remains understudied. The objective was to examine the impact of diets containing 6% corn oil, high oleic canola oil, docosahexaenoic acid + high oleic canola oil, and fish oil on plasma and organ levels of fatty acid ethanolamides, peroxisome proliferator-activated receptor-? regulatory targets, and lipid metabolism in Syrian Golden hamsters. After 29 days, in plasma, animals that were fed fish oil showed greater (p < 0.05) oleoylethanolamide and lower (p < 0.05) arachidonoylethanolamide and palmitoylethanolamide levels compared with other groups, while animals fed canola oil showed higher (p < 0.05) oleoylethanolamide levels in proximal intestine and liver than groups that were fed coin oil and fish oil. The canola oil group showed elevated (p < 0.01) fat oxidation (%) and over 3.0-fold higher (p < 0.05) hepatic-CD36 expression compared with the corn oil group. Hepatic-lipogenesis was lower (p < 0.05) in hamsters that were fed DHA-canola oil compared with the corn oil group. To conclude, dietary fatty acids produced shifts in plasma and organ levels of arachidonoylethanolamide, oleoylethanolamide, and palmitoylethanolamid, which were accompanied by changes in gene expression, lipogenesis, and energy expenditure, suggesting mechanisms through which dietary fatty acids influence disease risk. PMID:23855275

Lin, Lin; Rideout, Todd; Yurkova, Natalia; Yang, Haifeng; Eck, Peter; Jones, Peter J H

2013-08-01

253

Fatty acid transfer from intestinal fatty acid binding protein to membranes: electrostatic and hydrophobic interactions  

Microsoft Academic Search

Intestinal fatty acid binding protein (IFABP) is thought to participate in the intracellular transport of fatty ac- ids (FAs). Fatty acid transfer from IFABP to phospholipid membranes is proposed to occur during protein-membrane collisional interactions. In this study, we analyzed the partici- pation of electrostatic and hydrophobic interactions in the col- lisional mechanism of FA transfer from IFABP to membranes.

B. Corsico; Gisela R. Franchini; Kuo-Tung Hsu; Judith Storch

2005-01-01

254

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

255

Merging of multiple signals regulating ?9 fatty acid desaturase gene transcription in Saccharomyces cerevisiae  

Microsoft Academic Search

Fatty acid desaturation, which requires molecular oxygen (O 2) as an electron acceptor, is catalyzed by ?9 fatty acid desaturase, which is encoded by OLE1 in Saccharomyces cerevisiae. Transcription of the OLE1 gene is repressed by unsaturated fatty acids (UFAs) and activated by hypoxia and low temperatures via the endoplasmic reticulum membrane protein Mga2p. We previously reported the isolation of

Y. Nakagawa; A. Ueda; Y. Kaneko; S. Harashima

2003-01-01

256

Fatty acid and phytosterol content of commercial saw palmetto supplements.  

PubMed

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

2013-09-01

257

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

258

Consequences of Essential Fatty Acids  

PubMed Central

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

Lands, Bill

2012-01-01

259

Tracing fatty acid metabolism by click chemistry.  

PubMed

Fatty acids are abundant constituents of all biological systems, and their metabolism is important for normal function at all levels of an organism. Aberrations in fatty acid metabolism are associated with pathological states and have become a focus of current research, particularly due to the interest in metabolic overload diseases. Here we present a click-chemistry-based method that allows tracing of fatty acid metabolism in virtually any biological system. It combines high sensitivity with excellent linearity and fast sample turnover. Since it is free of radioactivity, it can be combined with any other modern analysis technology and can be used in high-throughput applications. Using the new method, we provide for the first time an analysis of cellular fatty metabolism with high time resolution and a comprehensive comparison of utilization of a broad spectrum of fatty acids in hepatoma and adipose cell lines. PMID:22999348

Thiele, Christoph; Papan, Cyrus; Hoelper, Dominik; Kusserow, Kalina; Gaebler, Anne; Schoene, Mario; Piotrowitz, Kira; Lohmann, Daniel; Spandl, Johanna; Stevanovic, Ana; Shevchenko, Andrej; Kuerschner, Lars

2012-12-21

260

Inhibitors of fatty acid biosynthesis in sunflower seeds.  

PubMed

During de novo fatty acid synthesis in sunflower seeds, saturated fatty acid production is influenced by the competition between the enzymes of the principal pathways and the saturated acyl-ACP thioesterases. Genetic backgrounds with more efficient saturated acyl-ACP thioesterase alleles only express their phenotypic effects when the alleles for the enzymes in the main pathway are less efficient. For this reason, we studied the incorporation of [2-(14)C]acetate into the lipids of developing sunflower seeds (Helianthus annuus L.) from several mutant lines in vivo. The labelling of different triacylglycerol fatty acids in different oilseed mutants reflects the fatty acid composition of the seed and supports the channelling theory of fatty acid biosynthesis. Incubation with methyl viologen diminished the conversion of stearoyl-ACP to oleoyl-ACP in vivo through a decrease in the available reductant power. In turn, this led to the accumulation of stearoyl-ACP to the levels detected in seeds from high stearic acid mutants. The concomitant reduction of oleoyl-ACP content inside the plastid allowed us to study the activity of acyl-ACP thioesterases on saturated fatty acids. In these mutants, we verified that the accumulation of saturated fatty acids requires efficient thioesterase activity on saturated-ACPs. By studying the effects of cerulenin on the in vivo incorporation of [2-(14)C]acetate into lipids and on the in vitro activity of beta-ketoacyl-ACP synthase II, we found that elongation to very long chain fatty acids can occur both inside and outside of the plastid in sunflower seeds. PMID:16500723

Pleite, Rafael; Martínez-Force, Enrique; Garcés, Rafael

2006-09-01

261

[Metabolism of fatty acids in the healthy myocardium and in ischemia].  

PubMed

Data on absorption and consumption in heart tissue of free and ester-bound fatty acids from blood lipids are discussed. Preferential utilization of individual fatty acids in heart tissue from blood lipids is considered. Dependence of fatty acid metabolism on the activity of tricarboxylic acid cycle, interrelationship between metabolism of endogenous and exogenous fatty acids in heart muscle are considered. The data are analyzed on pathways of exogenous fatty acids turnover in tissues, their conversion into endogenous fatty acids, specific for individual tissue, cells and their organelles. Development of syndrome of unsaturated fatty acids deficiency, induced by incomplete fatty diet, is discussed. Metabolism of fatty acids in heart under conditions of oxygen deficiency is considered. The data are reviewed on the effects of hypoxia on metabolism of fatty acids in myocardium. Carbohydrate and fatty acid consumption in heart muscle, typical alterations in fatty acid incorporation into heart lipids, effect of fatty acids excess on functioning of sarcoplasmic reticulum and mitochondrial membranes are discussed. PMID:6396941

Matiushin, I F; Boiarinov, G A; Bogdarin, Iu A

1984-01-01

262

Modification of the fatty acid composition of bovine tissues  

E-print Network

to determine if their activity rates can be influenced by dietary manipulations. Both objectives are important for the beef industry in that these areas of research can aid in the development of beef products with a modified fatty acid content... to feedings of olive oil and olive oil supplemented with medium chain triglycerides. The level of unsaturated fatty acids in these samples however did not differ significantly, and they suggest that these changes are related to the maintenance...

Chang, Joyce

1990-01-01

263

Hydroxy long-chain fatty acids in fungi  

Microsoft Academic Search

Hydroxy long-chain fatty acids occur widely in animals and plants and have important physiological activities in these eukaryotes. There are indications that these compounds are also common and important in fungi. The occurrence of hydroxy-polyunsaturated fatty acids (hydroxy-PUFAs) is of biotechnological importance, because these compounds are potentially high-value lipid products with medical applications. This review pays particular attention to the

M. S. Dyk; J. L. F. Kock; A. Botha

1994-01-01

264

Anandamide and 2-arachidonoylglycerol inhibit fatty acid amide hydrolase by activating the lipoxygenase pathway of the arachidonate cascade.  

PubMed

Treatment of intact human neuroblastoma CHP100 cells with anandamide (arachidonoylethanolamide, AEA) or 2-arachidonoylglycerol (2-AG) inhibits intracellular fatty acid amide hydrolase (FAAH). This effect was not associated with covalent modifications of FAAH, since specific inhibitors of farnesyltransferase, kinases, phosphatases, glycosyltransferase or nitric oxide synthase were ineffective. Electrophoretic analysis of (33)P-labelled proteins, Western blot with anti-phosphotyrosine antibodies, and glycan analysis of cellular proteins confirmed the absence of covalent modifications of FAAH. The inhibition by AEA was paralleled by an increased arachidonate release, which was not observed upon treatment of cells with linoleoylethanolamide, palmitoylethanolamide, or oleoylethanolamide. Moreover, cell treatment with AEA or 2-AG increased the activity of cyclooxygenase and 5-lipoxygenase, and the hydro(pero)xides generated from arachidonate by lipoxygenase were shown to inhibit FAAH, with inhibition constants in the low micromolar range. Consistently, inhibitors of 5-lipoxygenase, but not those of cyclooxygenase, significantly counteracted the inhibition of FAAH by AEA or 2-AG. PMID:11095952

Maccarrone, M; Salvati, S; Bari, M; Finazzi-Agró

2000-11-30

265

Insulin resistance reduces arterial prostacyclin synthase and eNOS activities by increasing endothelial fatty acid oxidation  

PubMed Central

Insulin resistance markedly increases cardiovascular disease risk in people with normal glucose tolerance, even after adjustment for known risk factors such as LDL, triglycerides, HDL, and systolic blood pressure. In this report, we show that increased oxidation of FFAs in aortic endothelial cells without added insulin causes increased production of superoxide by the mitochondrial electron transport chain. FFA-induced overproduction of superoxide activated a variety of proinflammatory signals previously implicated in hyperglycemia-induced vascular damage and inactivated 2 important antiatherogenic enzymes, prostacyclin synthase and eNOS. In 2 nondiabetic rodent models — insulin-resistant, obese Zucker (fa/fa) rats and high-fat diet–induced insulin-resistant mice — inactivation of prostacyclin synthase and eNOS was prevented by inhibition of FFA release from adipose tissue; by inhibition of the rate-limiting enzyme for fatty acid oxidation in mitochondria, carnitine palmitoyltransferase I; and by reduction of superoxide levels. These studies identify what we believe to be a novel mechanism contributing to the accelerated atherogenesis and increased cardiovascular disease risk occurring in people with insulin resistance. PMID:16528409

Du, Xueliang; Edelstein, Diane; Obici, Silvana; Higham, Ninon; Zou, Ming-Hui; Brownlee, Michael

2006-01-01

266

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

267

Comparative fatty acid composition of four Sargassum species (Fucales, Phaeophyta)  

NASA Astrophysics Data System (ADS)

Fatty acid composition of four Sargassum species from Qingdao and Shidao, Shandong Province was investigated. 16:0 (palmitic acid) was the major saturated fatty acid. C18 and C20 were the main polyunsaturated fatty acids (PUFAs). Arachidonic acid and eicosapentaenoic acid predominated among polyenoic acids in all the algal species examined, except for Sargassum sp. which had low concentration of eicosapentaenoic acid.

Wu, Xiang-Chun; Lu, Bao-Ren; Tseng, C. K.

1995-12-01

268

Enhanced activation of phospholipase C and insulin secretion from islets incubated in fatty acid–free bovine serum albumin  

Microsoft Academic Search

Incubation in 100 ?mol\\/L fatty acid–free bovine serum albumin (FAF-BSA) significantly amplifies insulin secretion from isolated, perifused rat islets. When compared with the responses of control islets incubated in 100 ?mol\\/L radioimmunoassay-grade BSA, insulin secretion rates were increased 2- to 3-fold when these islets were stimulated with 10 mmol\\/L glucose alone or with the combination of 10 mmol\\/L glucose, 15

Walter S. Zawalich; Kathleen C. Zawalich

2008-01-01

269

Phospholipid Fatty Acid Composition, Biomass, and Activity of Microbial Communities from Two Soil Types Experimentally Exposed to Different Heavy Metals  

PubMed Central

The phospholipid fatty acid (PLFA) pattern was analyzed in a forest humus and in an arable soil experimentally polluted with Cd, Cu, Ni, Pb, or Zn at different concentrations. In both soil types, there were gradual changes in the PLFA patterns for the different levels of metal contamination. The changes in the forest soil were similar irrespective of which metal was used, while in the arable soil the changes due to Cu contamination differed from those due to the other metals. Several PLFAs reacted similarly to the metal amendments in the two soil types, while others showed different responses. In both soils, the metal pollution resulted in a decrease in the iso-branched PLFAs i15:0 and i17:0 and in the monounsaturated 16:1?5 and 16:1?7c fatty acids, while increases were found for i16:0, the branched br17:0 and br18:0, and the cyclopropane cy17:0 fatty acids. In the forest soil, the methyl branched PLFAs 10Me16:0, 10Me17:0, and 10Me18:0 increased in metal-polluted soils, indicating an increase in actinomycetes, while in the arable soil a decrease was found for 10Me16:0 and 10Me18:0 in response to most metals. The bacterial PLFAs 15:0 and 17:0 increased in all metal-contaminated samples in the arable soil, while they were unaffected in the forest soil. Fatty acid 18:2?6, which is considered to be predominantly of fungal origin, increased in the arable soil, except in the Cu-amended samples, in which it decreased instead. Effects on the PLFA patterns were found at levels of metal contamination similar to or lower than those at which effects on ATP content, soil respiration, or total amount of PLFAs had occurred. PMID:16349080

Frostegård, Å.; Tunlid, A.; Bååth, E.

1993-01-01

270

Human serum-derived hydroxy long-chain fatty acids exhibit anti-inflammatory and anti-proliferative activity  

Microsoft Academic Search

Background  Circulating levels of novel long-chain hydroxy fatty acids (called GTAs) were recently discovered in the serum of healthy\\u000a subjects which were shown to be reduced in subjects with colorectal cancer (CRC), independent of tumor burden or disease stage.\\u000a The levels of GTAs were subsequently observed to exhibit an inverse association with age in the general population. The current\\u000a work investigates

Shawn A Ritchie; Dushmanthi Jayasinghe; Gerald F Davies; Pearson Ahiahonu; Hong Ma; Dayan B Goodenowe

2011-01-01

271

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...

272

Omega-3 fatty acids upregulate adult neurogenesis.  

PubMed

Omega-3 fatty acids play crucial roles in the development and function of the central nervous system. These components, which must be obtained from dietary sources, have been implicated in a variety of neurodevelopmental and psychiatric disorders. Furthermore, the presence of omega-6 fatty acids may interfere with omega-3 fatty acid metabolism. The present study investigated whether changes in dietary ratios of omega-3:omega-6 fatty acids influence neurogenesis in the lobster (Homarus americanus) brain where, as in many vertebrate species, neurogenesis persists throughout life. The factors that regulate adult neurogenesis are highly conserved among species, and the crustacean brain has been successfully utilized as a model for investigating this process. In this study, lobsters were fed one of three diets that differed in fatty acid content. These animals were subsequently incubated in 5-bromo-2'-deoxyuridine (BrdU) to detect cells in S-phase of the cell cycle. A quantitative analysis of the resulting BrdU-labeled cells in the projection neuron cluster in the brain shows that short-term augmentation of dietary omega-3 relative to omega-6 fatty acids results in significant increases in the numbers of S phase cells, and that the circadian pattern of neurogenesis is also altered. It is proposed that the ratio of omega-3:omega-6 fatty acids may alter neurogenesis via modulatory influences on membrane proteins, cytokines and/or neurotrophins. PMID:17240063

Beltz, Barbara S; Tlusty, Michael F; Benton, Jeanne L; Sandeman, David C

2007-03-26

273

Maternal micronutrients, omega-3 fatty acids, and placental PPAR? expression.  

PubMed

An altered one-carbon cycle is known to influence placental and fetal development. We hypothesize that deficiency of maternal micronutrients such as folic acid and vitamin B12 will lead to increased oxidative stress, reduced long-chain polyunsaturated fatty acids, and altered expression of peroxisome proliferator activated receptor (PPAR?) in the placenta, and omega-3 fatty acid supplementation to these diets will increase the expression of PPAR?. Female rats were divided into 5 groups: control, folic acid deficient, vitamin B12 deficient, folic acid deficient + omega-3 fatty acid supplemented, and vitamin B12 deficient + omega-3 fatty acid supplemented. Dams were dissected on gestational day 20. Maternal micronutrient deficiency leads to lower (p < 0.05) levels of placental docosahexaenoic acid, arachidonic acid, PPAR? expression and higher (p < 0.05) levels of plasma malonidialdehyde, placental IL-6, and TNF-?. Omega-3 fatty acid supplementation to a vitamin B12 deficient diet normalized the expression of PPAR? and lowered the levels of placental TNF-?. In the case of supplementation to a folic acid deficient diet it lowered the levels of malonidialdehyde and placental IL-6 and TNF-?. This study has implications for fetal growth as oxidative stress, inflammation, and PPAR? are known to play a key role in the placental development. PMID:24749811

Meher, Akshaya P; Joshi, Asmita A; Joshi, Sadhana R

2014-07-01

274

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

E-print Network

significantly reduced IL-2 secretion, however, only when the CD28 receptor was engaged. In the T cell subset studies, diets varied by lipid composition only containing either safflower oil (SAF), FO, or an eicosapentaenoic/docosahexaenoic (EPA/DHA) acid...

Arrington, Jennifer L

2000-01-01

275

Proto-oncogene FBI-1 (Pokemon) and SREBP-1 synergistically activate transcription of fatty-acid synthase gene (FASN).  

PubMed

FBI-1 (Pokemon/ZBTB7A) is a proto-oncogenic transcription factor of the BTB/POZ (bric-à-brac, tramtrack, and broad complex and pox virus zinc finger) domain family. Recent evidence suggested that FBI-1 might be involved in adipogenic gene expression. Coincidentally, expression of FBI-1 and fatty-acid synthase (FASN) genes are often increased in cancer and immortalized cells. Both FBI-1 and FASN are important in cancer cell proliferation. SREBP-1 is a major regulator of many adipogenic genes, and FBI-1 and SREBP-1 (sterol-responsive element (SRE)-binding protein 1) interact with each other directly via their DNA binding domains. FBI-1 enhanced the transcriptional activation of SREBP-1 on responsive promoters, pGL2-6x(SRE)-Luc and FASN gene. FBI-1 and SREBP-1 synergistically activate transcription of the FASN gene by acting on the proximal GC-box and SRE/E-box. FBI-1, Sp1, and SREBP-1 can bind to all three SRE, GC-box, and SRE/E-box. Binding competition among the three transcription factors on the GC-box and SRE/E-box appears important in the transcription regulation. FBI-1 is apparently changing the binding pattern of Sp1 and SREBP-1 on the two elements in the presence of induced SREBP-1 and drives more Sp1 binding to the proximal promoter with less of an effect on SREBP-1 binding. The changes induced by FBI-1 appear critical in the synergistic transcription activation. The molecular mechanism revealed provides insight into how proto-oncogene FBI-1 may attack the cellular regulatory mechanism of FASN gene expression to provide more phospholipid membrane components needed for rapid cancer cell proliferation. PMID:18682402

Choi, Won-Il; Jeon, Bu-Nam; Park, Hyejin; Yoo, Jung-Yoon; Kim, Yeon-Sook; Koh, Dong-In; Kim, Myung-Hwa; Kim, Yu-Ri; Lee, Choong-Eun; Kim, Kyung-Sup; Osborne, Timothy F; Hur, Man-Wook

2008-10-24

276

Omega-3 fatty acids and cardiovascular disease.  

PubMed

Cardioceuticals are nutritional supplements that contain all the essential nutrients including vitamins, minerals, omega-3-fatty acids and other antioxidants like a-lipoic acid and coenzyme Q10 in the right proportion that provide all round protection to the heart by reducing the most common risks associated with the cardiovascular disease including high low-density lipoprotein cholesterol and triglyceride levels and factors that contribute to coagulation of blood. Omega-3 fatty acids have been shown to significantly reduce the risk for sudden death caused by cardiac arrhythmias and all-cause mortality in patients with known coronary heart disease. Omega-3 fatty acids are also used to treat hyperlipidemia and hypertension. There are no significant drug interactions with omega-3 fatty acids. The American Heart Association recommends consumption of two servings of fish per week for persons with no history of coronary heart disease and at least one serving of fish daily for those with known coronary heart disease. Approximately 1 g/day of eicosapentaenoic acid plus docosahexaenoic acid is recommended for cardio protection. Higher dosages of omega-3 fatty acids are required to reduce elevated triglyceride levels (2-4 g/day). Modest decreases in blood pressure occur with significantly higher dosages of omega-3 fatty acids. PMID:25720716

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

2015-01-01

277

Enhancement of thrombin-thrombomodulin-catalysed protein C activation by phosphatidylethanolamine containing unsaturated fatty acids: possible physiological significance of phosphatidylethanolamine in anticoagulant activity of thrombomodulin.  

PubMed Central

The effects of phospholipid vesicles and their fatty acid compositions on the acceleration of Protein C activation by thrombin-thrombomodulin was studied in vitro. Four main phospholipid fractions were prepared from cultured human umbilical vein endothelial cells, and purified thrombomodulin from human placenta was reconstituted into vesicles consisting of phosphatidylcholine (PtdCho) alone, PtdCho plus phosphatidylethanolamine (PtdEtn), PtdCho plus phosphatidylserine (PtdSer) and PtdCho plus PtdIns (1:1, w/w in each case). Vesicles of PtdCho, PtdIns/PtdCho, PtdSer/PtdCho and PtdEtn/PtdCho increased thrombin-thrombomodulin-catalysed protein C activation by 1.2-, 1.9-, 4.3- and 8.4-fold respectively compared with that in the absence of phospholipid. This Protein C activation was not affected by distearoyl PtdEtn/distearoyl PtdCho, whereas it was markedly increased with increasing content of unsaturated fatty acid in PtdEtn. The thrombin-dependent Protein C activation by thrombomodulin reconstituted into dilinolenoyl PtdEtn/distearoyl PtdCho was 14.6 times that by thrombomodulin reconstituted into distearoyl PtdEtn/distearoyl PtdCho, as a result of a decrease in the dissociation constant (Kd) for thrombin and the Michaelis constant (Km) for Protein C of thrombomodulin. Binding of Protein C to PtdEtn/PtdCho fixed to a microwell plate required the presence of CaCl2 and increased with increasing degree of unsaturation of fatty acid in PtdEtn. As PtdEtn appeared on the outside of the plasma membrane in cultured human umbilical vein endothelial cells after thrombin stimulation, it was presumed that Protein C activation could be elevated by PtdEtn at the outer surface of the plasma membrane via an increased affinity between thrombomodulin, thrombin and Protein C, resulting from both increased formation of the thrombin-thrombomodulin complex via a conformational change in thrombomodulin and increased binding of Protein C to the membrane phospholipid in a Ca(2+)-dependent manner. PMID:8053894

Horie, S; Ishii, H; Hara, H; Kazama, M

1994-01-01

278

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. PMID:25756142

Koren, Gideon

2015-01-01

279

Effects of dietary protein\\/carbohydrate ratio on fat deposition and gene expression of peroxisome proliferator activated receptor ? and heart fatty acid-binding protein of finishing pigs  

Microsoft Academic Search

The present study was conducted to investigate the effect of dietary protein\\/carbohydrate (CH2O) ratio on fat deposition and expression of peroxisome proliferator activated receptor ? (PPAR?) and heart fatty acid-binding protein (H-FABP) genes in muscle and subcutaneous adipose tissue in pigs. Twenty pigs (73.9±1.2kg BW) were used in a single factorial experiment, and allocated by BW and ultrasound backfat thickness

Xiulan Guo; Renyong Tang; Wei Wang; Dayu Liu; Kangning Wang

2011-01-01

280

Developmental changes of lipoxygenase and fatty acid hydroperoxide lyase activities in cultured cells of Marchantia polymorpha  

Microsoft Academic Search

Lipoxygenase activity in Marchantia polymorpha cells rapidly increased during the lag phase of cell growth. In the logarithmically-growing cells activity tended to decrease, but again increased in the stationary phase. The two lipoxygenases enhanced in the lag and the stationary phases were purifed. Then could not be differentiated from each other by their enzymatic properties, such as pH-activity profiles, substrate

Kenji Matsui; Yoshiaki Kaji; Tadahiko Kajiwara; Akikazu Hatanaka

1996-01-01

281

Down-regulated expression of PPARalpha target genes, reduced fatty acid oxidation and altered fatty acid composition in the liver of mice transgenic for hTNFalpha.  

PubMed

The present study investigated the hepatic regulation of fatty acid metabolism in hTNFalpha transgenic mice. Reduced hepatic mRNA levels and activities of carnitine palmitoyltransferase-II (CPT-II) and mitochondrial HMG-CoA synthase were observed, accompanied by decreased fatty acid oxidation, fatty acyl-CoA oxidase and fatty acid synthase (FAS) activities and down-regulated gene expression of mitochondrial acetyl-CoA carboxylase 2 (ACC2). The mRNA levels of peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARdelta were reduced. The hepatic fatty acid composition was altered, with increased amounts of saturated and polyunsaturated fatty acids. The relative amounts of Delta(9) desaturated fatty acids were decreased, as was Delta(9)desaturase mRNA. The CPT-I mRNA level remained unchanged. The PPARalpha targeted genes CPT-II and HMG-CoA synthase are potential regulators of mitochondrial fatty acid oxidation and ketogenesis in hTNFalpha transgenic mice, and the increased propionyl-CoA level found is a possible inhibitor of these processes. Reduced mitochondrial and peroxisomal fatty acid oxidation may explain the increased hepatic triglyceride level induced by TNFalpha. This is not due to de novo fatty acid synthesis as both FAS activity and gene expression of ACC2 were reduced. PMID:15893958

Glosli, Heidi; Gudbrandsen, Oddrun Anita; Mullen, Antony J; Halvorsen, Bente; Røst, Therese H; Wergedahl, Hege; Prydz, Hans; Aukrust, Pål; Berge, Rolf K

2005-06-01

282

PPAR ? activators improve glucose homeostasis by stimulating fatty acid uptake in the adipocytes  

Microsoft Academic Search

It is currently thought that the effects of PPAR? activation on glucose homeostasis may be due to the effect of this nuclear receptor on the production of adipocyte-derived signalling molecules, which affect muscle glucose metabolism. Potential signalling molecules derived from adipocytes and modified by PPAR? activation include TNF? and leptin, which both interfere with glucose homeostasis. In addition to its

Geneviève Martin; Kristina Schoonjans; Bart Staels; Johan Auwerx

1998-01-01

283

Eicosapentaenoic and docosahexaenoic acid affect mitochondrial and peroxisomal fatty acid oxidation in relation to substrate preference  

Microsoft Academic Search

Decreased triacylglycerol synthesis within hepatocytes due to decreased diacylglycerol acyltransferase (DGAT) activity has\\u000a been suggested to be an important mechanism by which diets rich in fish oil lower plasma triacylglycerol levels. New findings\\u000a suggest that eicosapentaenoic acid (EPA), and not docosahexaenoic acid (DHA), lowers plasma triacylglycerol by increased mitochondrial\\u000a fatty acid oxidation and decreased availability of fatty acids for triacylglycerol

Lise Madsen; Arild C. Rustan; Hege Vaagenes; Kjetil Berge; Endre Dyrøy; Rolf K. Berge

1999-01-01

284

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

285

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

286

Free fatty acids induce ER stress and block antiviral activity of interferon alpha against hepatitis C virus in cell culture  

PubMed Central

Background Hepatic steatosis is recognized as a major risk factor for liver disease progression and impaired response to interferon based therapy in chronic hepatitis C (CHC) patients. The mechanism of response to interferon-alpha (IFN-?) therapy under the condition of hepatic steatosis is unexplored. We investigated the effect of hepatocellular steatosis on hepatitis C virus (HCV) replication and IFN-? antiviral response in a cell culture model. Methods Sub-genomic replicon (S3-GFP) and HCV infected Huh-7.5 cells were cultured with a mixture of saturated (palmitate) and unsaturated (oleate) long-chain free fatty acids (FFA). Intracytoplasmic fat accumulation in these cells was visualized by Nile red staining and electron microscopy then quantified by microfluorometry. The effect of FFA treatment on HCV replication and IFN-? antiviral response was measured by flow cytometric analysis, Renilla luciferase activity, and real-time RT-PCR. Results FFA treatment induced dose dependent hepatocellular steatosis and lipid droplet accumulation in the HCV replicon cells was confirmed by Nile red staining, microfluorometry, and by electron microscopy. Intracellular fat accumulation supports replication more in the persistently HCV infected culture than in the sub-genomic replicon (S3-GFP) cell line. FFA treatment also partially blocked IFN-? response and viral clearance by reducing the phosphorylation of Stat1 and Stat2 dependent IFN-? promoter activation. We show that FFA treatment induces endoplasmic reticulum (ER) stress response and down regulates the IFNAR1 chain of the type I IFN receptor leading to defective Jak-Stat signaling and impaired antiviral response. Conclusion These results suggest that intracellular fat accumulation in HCV cell culture induces ER stress, defective Jak-Stat signaling, and attenuates the antiviral response, thus providing an explanation to the clinical observation regarding how hepatocellular steatosis influences IFN-? response in CHC. PMID:22863531

2012-01-01

287

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

288

Coupling of Fatty Acid and Phospholipid Synthesis in Bacillus subtilis?  

PubMed Central

plsX (acyl-acyl carrier protein [ACP]:phosphate acyltransferase), plsY (yneS) (acyl-phosphate:glycerol-phosphate acyltransferase), and plsC (yhdO) (acyl-ACP:1-acylglycerol-phosphate acyltransferase) function in phosphatidic acid formation, the precursor to membrane phospholipids. The physiological functions of these genes was inferred from their in vitro biochemical activities, and this study investigated their roles in gram-positive phospholipid metabolism through the analysis of conditional knockout strains in the Bacillus subtilis model system. The depletion of PlsX led to the cessation of both fatty acid synthesis and phospholipid synthesis. The inactivation of PlsY also blocked phospholipid synthesis, but fatty acid formation continued due to the appearance of acylphosphate intermediates and fatty acids arising from their hydrolysis. Phospholipid synthesis ceased following PlsC depletion, but fatty acid synthesis continued at a high rate, leading to the accumulation of fatty acids arising from the dephosphorylation of 1-acylglycerol-3-P followed by the deacylation of monoacylglycerol. Analysis of glycerol 3-P acylation in B. subtilis membranes showed that PlsY was an acylphosphate-specific acyltransferase, whereas PlsC used only acyl-ACP as an acyl donor. PlsX was found in the soluble fraction of disrupted cells but was associated with the cell membrane in intact organisms. These data establish that PlsX is a key enzyme that coordinates the production of fatty acids and membrane phospholipids in B. subtilis. PMID:17557823

Paoletti, Luciana; Lu, Ying-Jie; Schujman, Gustavo E.; de Mendoza, Diego; Rock, Charles O.

2007-01-01

289

Palm oil fatty acid as an activator in carbon black filled natural rubber compounds: dynamic properties, curing characteristics, reversion and fatigue studies  

Microsoft Academic Search

The effects of palm oil fatty acid and carbon black concentration on dynamic properties, curing characteristics, reversion and fatigue life in natural rubber compounds were studied. The scorch time, t2 and cure time, t90 were found to increase with increasing palm oil fatty acid concentration. For dynamic properties, the maximum elastic torque, increased with increasing acid concentration, whereas the minimum

Hanafi Ismail; H Anuar

2000-01-01

290

Polyunsaturated fatty acid concentrates from borage and linseed oil fatty acids  

Microsoft Academic Search

A modified low-temperature solvent crystallization process was employed for the enrichment of polyunsaturated fatty acids\\u000a (PUFA) in borage and linseed oil fatty acids. The effects of solvent, operation temperature, and solvent to free fatty acid\\u000a (FFA) ratio on the concentration of PUFA were investigated. The best results were achieved when a mixture of 30% acetonitrile\\u000a and 70% acetone was used

Tor-Chern Chen; Yi-Hsu Ju

2001-01-01

291

Fatty acid composition of danish margarines and shortenings, with special emphasis on trans fatty acids  

Microsoft Academic Search

Trans fatty acids from hydrogenated vegetable and marine oils could be as hypercholesterolemic and atherogenic as saturated fatty\\u000a acids. Hence, it is important to know the fatty acid composition in major food contributors, e.g., margarines and shortenings.\\u000a In 1992 margarines were examined, and in 1995 brands covering the entire Danish market were examined. Significant amounts\\u000a oftrans-18?1 were found only in

Lars Ovesen; Torben Leth; Kirsten Hansen

1996-01-01

292

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

PubMed Central

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

1994-01-01

293

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...

294

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...

295

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

296

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

297

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

298

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

299

Polyunsaturated fatty acid supply with human milk  

Microsoft Academic Search

Polyunsaturated fatty acids in human milk may derive from diet, liberation from maternal body stores, or endogenous synthesis\\u000a from precursor fatty acids. The contribution of each of these sources has not been studied in detail. Although maternal diet\\u000a is a key factor affecting human milk composition, other factors such as gestational age, stage of lactation, nutritional status,\\u000a and genetic background

T. U. Sauerwald; H. Demmelmair; B. Koletzko

2001-01-01

300

The fatty acid composition of human colostrum  

Microsoft Academic Search

Summary   We reviewed 15 studies reporting on the fatty acid composition of colostrum lipids from 16 geographic regions: 11 European\\u000a studies and one study each from Central America, the Caribbean, Australia and Asia. The contents of essential fatty acids,\\u000a saturates and polyunsaturates were similar in the southern European countries Spain, Slovenia and France. Colostrum of St.\\u000a Lucian women was high

Natasa Fidler; Berthold Koletzko

2000-01-01

301

Crystallization Behavior of Fatty Acid Methyl Esters  

Microsoft Academic Search

Biodiesel from most agricultural feedstocks has flow properties that are prone to startup and operability problems during\\u000a cold weather. Biodiesel from soybean oil is generally a mixture of long-chain fatty acid alkyl esters composed of 0.15–0.20\\u000a mass fraction saturated esters (melting point [MP] ? 0 °C) mixed with unsaturated esters (MP < 0 °C). This work investigates\\u000a the crystallization properties of two saturated fatty acid methyl

Robert O. Dunn

2008-01-01

302

Long-Chain Polyunsaturated Fatty Acids  

Microsoft Academic Search

Long-chain polyunsaturated fatty acids (LC-PUFA) are essential for normal development. Fetal accretion of LC-PUFA occurs during the last trimester of gestation; therefore, premature infants are born with minimal LC-PUFA reserves. Recent studies indicate that the newborn can synthesize LC-PUFA from essential fatty acid precursors; however, the extent of de novo synthesis remains to be established. Postnatally, human milk provides LC-PUFA

Margit Hamosh

1998-01-01

303

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

304

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

305

Fatty acid composition in farmed great sturgeon Huso huso  

Microsoft Academic Search

In this study, fatty acid profiles in farmed great sturgeon Huso huso were determined and results compared with those of other farmed sturgeon species. C18:1, C18:2, C16:0, C18:3, and C18:0 were\\u000a the main fatty acids found in great sturgeon flesh and represented approximately 88% of total fatty acids. Monounsaturated\\u000a fatty acids were the most dominant class of fatty acids, followed

Mohammad Reza Ghomi; Mehdi Nikoo; Zeinolabedin Babaei

306

Fatty acid selectivity of lipases: ?-linolenic acid from borage oil  

Microsoft Academic Search

The ?-linolenic acid (Z,Z,Z-6,9,12-octadecatrienoic acid, GLA) present in borage oil free fatty acids was concentrated in esterification reactions that\\u000a were catalyzed by several preparations of the acyl-specific lipase ofGeotrichum candidum. In this manner, a 95% recovery of the GLA originally present in borage oil (25% GLA) was obtained as a highly enriched fatty\\u000a acid fraction with a GLA content of

Thomas A. Foglia; Philip E. Sonnet

1995-01-01

307

Seaweed extracts and unsaturated fatty acid constituents from the green alga Ulva lactuca as activators of the cytoprotective Nrf2–ARE pathway  

PubMed Central

Increased amounts of reactive oxygen species (ROS) have been implicated in many pathological conditions, including cancer. The major machinery that the cell employs to neutralize excess ROS is through the activation of the antioxidant-response element (ARE) that controls the activation of many phase II detoxification enzymes. The transcription factor that recognizes the ARE, Nrf2, can be activated by a variety of small molecules, most of which contain an ?,?-unsaturated carbonyl system. In the pursuit of chemopreventive agents from marine organisms, we built, fractionated, and screened a library of 30 field-collected eukaryotic algae from Florida. An edible green alga, Ulva lactuca, yielded multiple active fractions by ARE–luciferase reporter assay. We isolated three monounsaturated fatty acid (MUFA) derivatives as active components, including a new keto-type C18 fatty acid (1), the corresponding shorter chain C16 acid (2), and an amide derivative (3) of the C18 acid. Their chemical structures were elucidated by NMR and mass spectrometry. All three contain the conjugated enone motif between C7 and C9, which is thought to be responsible for the ARE activity. Subsequent biological studies focused on 1, the most active and abundant ARE activator isolated. C18 acid 1 induced the expression of ARE-regulated cytoprotective genes, including NAD(P)H:quinone oxidoreductase 1, heme oxygenase 1, thioredoxin reductase 1, both subunits of the glutamate–cysteine ligase (catalytic subunit and modifier subunit), and the cystine/glutamate exchange transporter, in IMR-32 human neuroblastoma cells. Its cellular activity requires the presence of Nrf2 and PI3K function, based on RNA interference and pharmacological inhibitor studies, respectively. Treatment with 1 led only to Nrf2 activation, and not the increase in production of NRF2 mRNA. To test its ARE activity and cytoprotective potential in vivo, we treated mice with a single dose of a U. lactuca fraction that was enriched with 1, which showed ARE-activating effects similar to those observed in vitro. This could be owing to this fraction's ability to stabilize Nrf2 through inhibition of Keap1-mediated Nrf2 ubiquitination and the subsequent accumulation and nuclear translocation of Nrf2. The induction of many ARE-driven antioxidant genes in vivo and most prominently in the heart agreed with the commonly recognized cardioprotective properties of MUFAs. A significant increase in Nqo1 transcript levels was also found in other mouse tissues such as the brain, lung, and stomach. Collectively, this study provides new insight into why consumption of dietary seaweed may have health benefits, and the identified compounds add to the list of chemopreventive dietary unsaturated fatty acids. PMID:23291594

Wang, Rui; Paul, Valerie J.; Luesch, Hendrik

2013-01-01

308

Seaweed extracts and unsaturated fatty acid constituents from the green alga Ulva lactuca as activators of the cytoprotective Nrf2-ARE pathway.  

PubMed

Increased amounts of reactive oxygen species (ROS) have been implicated in many pathological conditions, including cancer. The major machinery that the cell employs to neutralize excess ROS is through the activation of the antioxidant-response element (ARE) that controls the activation of many phase II detoxification enzymes. The transcription factor that recognizes the ARE, Nrf2, can be activated by a variety of small molecules, most of which contain an ?,?-unsaturated carbonyl system. In the pursuit of chemopreventive agents from marine organisms, we built, fractionated, and screened a library of 30 field-collected eukaryotic algae from Florida. An edible green alga, Ulva lactuca, yielded multiple active fractions by ARE-luciferase reporter assay. We isolated three monounsaturated fatty acid (MUFA) derivatives as active components, including a new keto-type C18 fatty acid (1), the corresponding shorter chain C16 acid (2), and an amide derivative (3) of the C18 acid. Their chemical structures were elucidated by NMR and mass spectrometry. All three contain the conjugated enone motif between C7 and C9, which is thought to be responsible for the ARE activity. Subsequent biological studies focused on 1, the most active and abundant ARE activator isolated. C18 acid 1 induced the expression of ARE-regulated cytoprotective genes, including NAD(P)H:quinone oxidoreductase 1, heme oxygenase 1, thioredoxin reductase 1, both subunits of the glutamate-cysteine ligase (catalytic subunit and modifier subunit), and the cystine/glutamate exchange transporter, in IMR-32 human neuroblastoma cells. Its cellular activity requires the presence of Nrf2 and PI3K function, based on RNA interference and pharmacological inhibitor studies, respectively. Treatment with 1 led only to Nrf2 activation, and not the increase in production of NRF2 mRNA. To test its ARE activity and cytoprotective potential in vivo, we treated mice with a single dose of a U. lactuca fraction that was enriched with 1, which showed ARE-activating effects similar to those observed in vitro. This could be owing to this fraction's ability to stabilize Nrf2 through inhibition of Keap1-mediated Nrf2 ubiquitination and the subsequent accumulation and nuclear translocation of Nrf2. The induction of many ARE-driven antioxidant genes in vivo and most prominently in the heart agreed with the commonly recognized cardioprotective properties of MUFAs. A significant increase in Nqo1 transcript levels was also found in other mouse tissues such as the brain, lung, and stomach. Collectively, this study provides new insight into why consumption of dietary seaweed may have health benefits, and the identified compounds add to the list of chemopreventive dietary unsaturated fatty acids. PMID:23291594

Wang, Rui; Paul, Valerie J; Luesch, Hendrik

2013-04-01

309

Is There a Fatty Acid Taste?  

PubMed Central

Taste is a chemical sense that aids in the detection of nutrients and guides food choice. A limited number of primary qualities comprise taste. Accumulating evidence has raised a question about whether fat should be among them. Most evidence indicates triacylglycerol is not an effective taste stimulus, though it clearly contributes sensory properties to foods by carrying flavor compounds and altering texture. However, there is increasing anatomical, electrophysiological, animal behavior, imaging, metabolic, and psychophysical evidence that free fatty acids are detectable when non-taste cues are minimized. Free fatty acids varying in saturation and chain length are detectable, suggesting the presence of multiple transduction mechanisms and/or a nonspecific mechanism in the oral cavity. However, confirmation of “fatty” as a taste primary will require additional studies that verify these observations are taste specific. Oral exposure to free fatty acids likely serves as a warning signal to discourage intake and influences lipid metabolism. PMID:19400700

Mattes, Richard D.

2010-01-01

310

An Immunomodulating Fatty Acid Analogue Targeting Mitochondria Exerts Anti-Atherosclerotic Effect beyond Plasma Cholesterol-Lowering Activity in apoE-/- Mice  

PubMed Central

Tetradecylthioacetic acid (TTA) is a hypolipidemic antioxidant with immunomodulating properties involving activation of peroxisome proliferator-activated receptors (PPARs) and proliferation of mitochondria. This study aimed to penetrate the effect of TTA on the development of atherosclerotic lesions in apolipoprotein (apo)-E-/- mice fed a high-fat diet containing 0.3% TTA for 12 weeks. These mice displayed a significantly less atherosclerotic development vs control. Plasma cholesterol was increased by TTA administration and triacylglycerol (TAG) levels in plasma and liver were decreased by TTA supplementation, the latter, probably due to increased mitochondrial fatty acid oxidation and reduced lipogenesis. TTA administration also changed the fatty acid composition in the heart, and the amount of arachidonic acid (ARA) and eicosapentaenoic acid (EPA) was reduced and increased, respectively. The heart mRNA expression of inducible nitric oxidase (NOS)-2 was decreased in TTA-treated mice, whereas the mRNA level of catalase was increased. Finally, reduced plasma levels of inflammatory mediators as IL-1?, IL-6, IL-17, TNF-? and IFN-? were detected in TTA-treated mice. These data show that TTA reduces atherosclerosis in apoE-/- mice and modulates risk factors related to atherosclerotic disorders. TTA probably acts at both systemic and vascular levels in a manner independent of changes in plasma cholesterol, and triggers TAG catabolism through improved mitochondrial function. PMID:24324736

Parolini, Cinzia; Bjørndal, Bodil; Holm, Sverre; Bohov, Pavol; Halvorsen, Bente; Brattelid, Trond; Manzini, Stefano; Ganzetti, Giulia S.; Dellera, Federica; Nygård, Ottar K.; Aukrust, Pål; Sirtori, Cesare R.; Chiesa, Giulia; Berge, Rolf K.

2013-01-01

311

An immunomodulating fatty acid analogue targeting mitochondria exerts anti-atherosclerotic effect beyond plasma cholesterol-lowering activity in apoe(-/-) mice.  

PubMed

Tetradecylthioacetic acid (TTA) is a hypolipidemic antioxidant with immunomodulating properties involving activation of peroxisome proliferator-activated receptors (PPARs) and proliferation of mitochondria. This study aimed to penetrate the effect of TTA on the development of atherosclerotic lesions in apolipoprotein (apo)-E(-/-) mice fed a high-fat diet containing 0.3% TTA for 12 weeks. These mice displayed a significantly less atherosclerotic development vs control. Plasma cholesterol was increased by TTA administration and triacylglycerol (TAG) levels in plasma and liver were decreased by TTA supplementation, the latter, probably due to increased mitochondrial fatty acid oxidation and reduced lipogenesis. TTA administration also changed the fatty acid composition in the heart, and the amount of arachidonic acid (ARA) and eicosapentaenoic acid (EPA) was reduced and increased, respectively. The heart mRNA expression of inducible nitric oxidase (NOS)-2 was decreased in TTA-treated mice, whereas the mRNA level of catalase was increased. Finally, reduced plasma levels of inflammatory mediators as IL-1?, IL-6, IL-17, TNF-? and IFN-? were detected in TTA-treated mice. These data show that TTA reduces atherosclerosis in apoE(-/-) mice and modulates risk factors related to atherosclerotic disorders. TTA probably acts at both systemic and vascular levels in a manner independent of changes in plasma cholesterol, and triggers TAG catabolism through improved mitochondrial function. PMID:24324736

Vik, Rita; Busnelli, Marco; Parolini, Cinzia; Bjørndal, Bodil; Holm, Sverre; Bohov, Pavol; Halvorsen, Bente; Brattelid, Trond; Manzini, Stefano; Ganzetti, Giulia S; Dellera, Federica; Nygård, Ottar K; Aukrust, Pål; Sirtori, Cesare R; Chiesa, Giulia; Berge, Rolf K

2013-01-01

312

Omega-3 Fatty Acids and FFAR4  

PubMed Central

The beneficial roles of omega-3 fatty acids (?3-FAs) on obesity, type 2 diabetes, and other metabolic diseases are well known. Most of these effects can be explained by their anti-inflammatory effects triggered through their receptor, free fatty acid receptor 4 (FFAR4) activation. Although the whole mechanism of action is not fully described yet, it has been shown that stimulation of ?3-FA to FFAR4 is followed by receptor phosphorylation. This makes FFAR4 to be capable of interacting with ?-arrestin-2, which in turn, results in association of ?-arrestin-2 with TAB1. This stealing of an important partaker of the inflammatory cascade leads to interruption of the pathway, resulting in reduced inflammation. Besides this regulation of the anti-inflammatory response, FFAR4 signaling also has been shown to regulate glucose homeostasis, adiposity, gastrointestinal peptide secretion, and taste preference. In this review, we summarize the current knowledge about the interaction of ?3-FAs with FFAR4 and the consequent opportunities for the application of ?3-FAs and possible FFAR4 targets. PMID:25076939

Oh, Da Young; Walenta, Evelyn

2014-01-01

313

Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat  

Microsoft Academic Search

The physiological activity of fish oil, and ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) affecting hepatic fatty acid oxidation was compared in rats. Five groups of rats were fed various experimental diets for 15 days. A group fed a diet containing 9.4% palm oil almost devoid of n-3 fatty acids served as a control. The test diets

Dang Diem Hong; Yoko Takahashi; Masay Kushiro; Takashi Ide

2003-01-01

314

[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

315

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

316

Antineoplastic unsaturated fatty acids from Fijian macroalgae  

PubMed Central

Phytochemical analysis of Fijian populations of the green alga Tydemania expeditionis led to the isolation of two new unsaturated fatty acids, 3(?)-hydroxy-octadeca-4(E),6(Z),15(Z)-trienoic acid (1) and 3(?)-hydroxy-hexadeca-4(E),6(Z)-dienoic acid (2), along with the known 3(?)-hydroxy-octadeca-4(E),6(Z)-dienoic acid (4). Investigations of the red alga Hydrolithon reinboldii led to identification of a new glycolipid, lithonoside (3), and five known compounds, 15-tricosenoic acid, hexacosa-5,9-dienoic methyl ester, ?-sitosterol, 10(S)-hydroxypheophytin A, and 10(R)-hydroxypheophytin A. The structures of 1-3 were elucidated by spectroscopic methods (1D and 2D-NMR spectroscopy and ESI-MS). Compounds 1, 2, and 4, containing conjugated double bonds, demonstrated moderate inhibitory activity against a panel of tumor cell lines (including breast, colon, lung, prostate and ovarian cells) with IC50 values ranging from 1.3 to 14.4 ?M. The similar cell selectivity patterns of these three compounds suggest that they might act by a common, but unknown, mechanism of action. PMID:18757069

Jiang, Ren-Wang; Hay, Mark E.; Fairchild, Craig R.; Prudhomme, Jacques; Le Roch, Karine; Aalbersberg, William; Kubanek, Julia

2008-01-01

317

Identification of Fatty Acids and Fatty Acid Amides in Human Meibomian Gland Secretions  

Microsoft Academic Search

PURPOSE. The complex superficial lipid layer of the tear film functions to prevent evaporation and maintain tear stability. Although classes of lipids found in the tear film have been reported, individual lipid species are currently being studied with more sophisticated methods. The purpose of this work was to show the identification of fatty acids and the fatty acid amides in

Kelly K. Nichols; Bryan M. Ham; Jason J. Nichols; Corrie Ziegler; Kari B. Green-Church

318

Modulation of fatty acid oxidation alters contact hypersensitivity to urushiols: role of aliphatic chain beta-oxidation in processing and activation of urushiols.  

PubMed

Lithraea caustica, or litre, a tree of the Anacardiaceae family that is endemic to the central region of Chile, induces a severe contact dermatitis in susceptible human beings. The allergen was previously isolated and characterized as a 3-(pentadecyl-10-enyl) catechol, a molecule belonging to the urushiol group of allergens isolated from poison ivy and poison oak plants. Because urushiols are pro-electrophilic haptens, it is believed that the reactive species are generated intracellularly by skin keratinocytes and Langerhans cells. The active species are presumed to modify self proteins which, after proteolytic processing, would generate immunogenic peptides carrying the hapten. The presence of a 15-carbon-length hydrophobic chain should impair antigen presentation of self-modified peptides by class I MHC molecules, either by steric hindrance or by limiting their sorting to the ER lumen. We have proposed that the shortening of the aliphatic chain by beta-oxidation within peroxisomes and/or mitochondria should be a requirement for the antigen presentation process. To test this hypothesis we investigated the effect of drugs that modify the fatty acid metabolism on urushiol-induced contact dermatitis in mice. Clofibrate, a peroxisomal proliferator in mice, increased the immune response to the urushiols from litre by 50%. Conversely, tetradecyl glycidic acid, an inhibitor of the uptake of fatty acids by mitochondria, decreased the hypersensitivity to the hapten. An increase in the level in glutathione by treatment of the animals with 2-oxotiazolidin-4-carboxilic acid lowered the response. Those findings strongly support a role for the fatty acid oxidative metabolism in the processing and activation of urushiols in vivo. PMID:8980288

Kalergis, A M; López, C B; Becker, M I; Díaz, M I; Sein, J; Garbarino, J A; De Ioannes, A E

1997-01-01

319

Synergistic effect of natural compounds on the fatty acid-induced autophagy of activated hepatic stellate cells.  

PubMed

Autophagy, a lysosomal pathway to maintain cellular homeostasis, is mediated via the mammalian target of rapamycin (mTOR)-dependent pathways. Hepatic stellate cells (HSCs), previously termed fat- or vitamin A-storing cells, can transdifferentiate into myofibroblast-like cells and are the most relevant cell type for overproduction of extracellular matrix (ECM) and development of liver fibrosis during injury. However, the role of autophagy in fat metabolism of HSCs remains unclear. This study investigates the regulatory effect of natural compounds on fatty acid-induced autophagy pathways of nonchemical-induced HSC (NHSC) and thioacetamide-induced HSC. Oleic acid (OA) and palmitic acid (PA) have shown a significant effect on cell proliferation with oil red O staining and Western blot confirming that OA and PA induce fat storage ability and autophagy protein expression in NHSC. Natural compounds rutin, curcumin, antroquinonol and benzyl cinnamate treatment have shown no effect on the autophagy protein expression. Nevertheless, cells pretreated with OA and PA then treated with rutin, curcumin, antroquinonol and benzyl cinnamate could significantly induce the light chain I/II (LC3 I/II) protein expression. In mTOR-dependent pathway, the PI3K-Class I, Akt, and p-mTOR proteins were decreased with PA treatment. However, there were no significant changes in PI3K-Class III and Beclin-1 protein expressions found to imply that this autophagy is unrelated to the mTOR-independent pathway. Taken together, the present study unveils rutin and curcumin as a possible effective stimulation for fatty acid-induced autophagy via mTOR-dependent pathways in NHSC. We further suggest the benefits of these natural compounds for alleviating liver fibrosis. PMID:24857031

Lee, Kuan-Wei; Thiyagarajan, Varadharajan; Sie, Huei-Wun; Cheng, Ming-Fan; Tsai, May-Jywan; Chia, Yi-Chen; Weng, Ching-Feng

2014-09-01

320

Fatty acid metabolism and thyroid hormones.  

PubMed

The importance of thyroid hormone signaling in the acute regulation of metabolic activity has been recognized for decades. Slowly, the underlying mechanisms responsible for this activity are being elucidated. A prominent characteristic of thyroid signaling is rapid increases in oxygen consumption and ATP production. This discovery implicated a non-genomic regulation of mitochondrial metabolism by thyroid hormones. Another important clue came from the discovery that thyroid hormones stimulated fatty acid oxidation (FAO) in a variety of tissues in a receptor-dependent, but transcriptional-independent manner. Recently, key linkages between thyroid hormone signaling and specific mitochondrial-targeted pathways have been discovered. This review focuses on the molecular mechanisms by which mitochondrial FAO can be increased through thyroid hormone signaling. The roles of both the full-length and shortened mitochondrial isoforms of thyroid hormone receptor will be discussed. Additionally, the impact of thyroid hormone signaling on dyslipidemias such as obesity, type II diabetes, and fatty liver disease will be considered. PMID:24436572

Sayre, Naomi L; Lechleiter, James D

2012-01-01

321

Associations between estimated fatty acid desaturase activities in serum lipids and adipose tissue in humans: links to obesity and insulin resistance  

PubMed Central

Fatty acid composition of serum lipids and adipose tissue triacylglycerols (AT-TAG) partly reflect dietary fatty acid intake. The fatty acid composition is, besides the diet, also influenced by desaturating enzymes that can be estimated using product-to-precursor fatty acid ratios. The interrelationships between desaturase indices derived from different serum lipid fractions and adipose tissue are unclear, as well as their associations with obesity and insulin resistance. We aimed to investigate cross-sectional correlations between desaturase indices as measured in serum lipid fractions (phospholipids; PL and free fatty acids; FFA) and in adipose tissue (AT-TAG). In a population-based sample of 301 healthy 60-year-old men various desaturase indices were assessed: stearoyl-CoA-desaturase (16:1n-7/16:0; SCD-16 and 18:1n-9/18:0; SCD-18, respectively), delta-6-desaturase (20:3n-6/18:2n-6; D6D) and delta-5-desaturase (20:4n-6/20:3n-6; D5D). Correlations with BMI and insulin resistance (HOMA-IR) were also examined. SCD-16 and D5D were significantly correlated between fractions and tissues (all r > 0.30), whereas SCD-18 and D6D were not. Desaturase indices in serum FFA and AT-TAG were significantly correlated; SCD-16 (r = 0.63), SCD-18 (r = 0.37), and D5D (r = 0.43). In phospholipids, SCD-16 was positively correlated to BMI (r = 0.15), while D5D negatively to both BMI (r = -0.30) and HOMA-IR (r = -0.31), all p < 0.01. D6D in both phospholipids and AT-TAG was positively correlated to HOMA-IR and BMI (all p < 0.01). In conclusion, SCD-1 and D5D activity indices showed overall strong correlations between lipid pools. SCD-1 activity index in adipose tissue is best reflected by 16:1/16:0-ratio in serum FFA, but associations with obesity and insulin resistance differ between these pools. D5D in PL was inversely related to obesity and insulin resistance, whereas D6D index showed positive associations. PMID:19712485

Warensjö, Eva; Rosell, Magdalena; Hellenius, Mai-Lis; Vessby, Bengt; De Faire, Ulf; Risérus, Ulf

2009-01-01

322

Iron translocation by free fatty acids.  

PubMed

Organic extracts of cigarette smoke and uncombusted tobacco contain substances capable of translocating iron from aqueous solutions into immiscible organic solvents. Such extracts will also effect the organic solvation of iron present in ferruginous forms of asbestos such as amosite and crocidolite (Qian and Eaton, Arch Biochem Biophys 1989, 275:280). These substances, previously detected by their iron-translocating properties, have now been purified and identified by mass spectroscopy as saturated fatty acids, predominantly stearic and palmitic acids. Organic extracts of tobacco smoke, as well as the pure fatty acids, also transfer ferrous iron into both isolated red cell membranes and intact human erythrocytes. The increased membrane iron may enhance cellular susceptibility to exogenous oxidants; erythrocyte membranes subject to fatty acid-mediated iron accumulation show elevated peroxidation of endogenous polyunsaturated fatty acids. These observations may help explain the phlogistic effects of tobacco use and suggest, in a broader context, that free fatty acids may act as physiologic and pathologic mediators of metal translocation. PMID:1750512

Qian, M W; Eaton, J W

1991-12-01

323

The nitrite-oxidizing community in activated sludge from a municipal wastewater treatment plant determined by fatty acid methyl ester-stable isotope probing.  

PubMed

Metabolically-active autotrophic nitrite oxidizers from activated sludge were labeled with (13)C-bicarbonate under exposure to different temperatures and nitrite concentrations. The labeled samples were characterized by FAME-SIP (fatty acid methyl ester-stable isotope probing). The compound cis-11-palmitoleic acid, which is the major lipid of the most abundant nitrite oxidizer in activated sludge, Candidatus Nitrospira defluvii, showed (13)C-incorporation in all samples exposed to 3 mM nitrite. Subsequently, the lipid cis-7-palmitoleic acid was labeled, and it indicated the activity of a nitrite oxidizer that was different from the known Nitrospira taxa in activated sludge. The highest incorporation of cis-7-palmitoleic acid label was found after incubation with a nitrite concentration of 0.3 mM at 17 and 22°C. While activity of Nitrobacter populations could not be detected by the FAME-SIP approach, an unknown nitrite oxidizer with the major lipid cis-9 isomer of palmitoleic acid exhibited (13)C-incorporation at 28°C with 30 mM nitrite. These results indicated flexibility of nitrite-oxidizing guilds in a complex community responding to different conditions. Labeled lipids so far not described for activated sludge-associated nitrifiers indicated the presence of unknown nitrite oxidizers in this habitat. The FAME-SIP-based information can be used to define appropriate conditions for the enrichment of nitrite-oxidizing guilds from complex samples. PMID:23921154

Kruse, Myriam; Zumbrägel, Sabine; Bakker, Evert; Spieck, Eva; Eggers, Till; Lipski, André

2013-10-01

324

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

325

Production of hydroxylated fatty acids in genetically modified plants  

SciTech Connect

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

2005-08-30

326

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

327

Specific bile acids inhibit hepatic fatty acid uptake  

PubMed Central

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

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

2012-01-01

328

Development of Escherichia coli MG1655 strains to produce long chain fatty acids by engineering fatty acid synthesis (FAS) metabolism.  

PubMed

The goal of this research was to develop recombinant Escherichia coli to improve fatty acid synthesis (FAS). Genes encoding acetyl-CoA carboxylase (accA, accB, accC), malonyl-CoA-[acyl-carrier-protein] transacylase (fabD), and acyl-acyl carrier protein thioesterase (EC 3.1.2.14 gene), which are all enzymes that catalyze key steps in the synthesis of fatty acids, were cloned and over-expressed in E. coli MG1655. The acetyl-CoA carboxylase (ACC) enzyme catalyzes the addition of CO(2) to acetyl-CoA to generate malonyl-CoA. The enzyme encoded by the fabD gene converts malonyl-CoA to malonyl-[acp], and the EC 3.1.2.14 gene converts fatty acyl-ACP chains to long chain fatty acids. All the genes except for the EC 3.1.2.14 gene were homologous to E. coli genes and were used to improve the enzymatic activities to over-express components of the FAS pathway through metabolic engineering. All recombinant E. coli MG1655 strains containing various gene combinations were developed using the pTrc99A expression vector. To observe changes in metabolism, the in vitro metabolites and fatty acids produced by the recombinants were analyzed. The fatty acids (C16) from recombinant strains were produced 1.23-2.41 times higher than that from the wild type. PMID:22112270

Jeon, Eunyoung; Lee, Sunhee; Won, Jong-In; Han, Sung Ok; Kim, Jihyeon; Lee, Jinwon

2011-06-10

329

Re-evaluation of fatty acid metabolism-related gene expression in nonalcoholic fatty liver disease.  

PubMed

Nonalcoholic fatty liver disease (NAFLD) is one of the most frequent causes of abnormal liver dysfunction, and its prevalence has markedly increased. We previously evaluated the expression of fatty acid metabolism-related genes in NAFLD and reported changes in expression that could contribute to increased fatty acid synthesis. In the present study, we evaluated the expression of additional fatty acid metabolism-related genes in larger groups of NAFLD (n=26) and normal liver (n=10) samples. The target genes for real-time PCR analysis were as follows: acetyl-CoA carboxylase (ACC) 1, ACC2, fatty acid synthase (FAS), sterol regulatory element-binding protein 1c (SREBP-1c), and adipose differentiation-related protein (ADRP) for evaluation of de novo synthesis and uptake of fatty acids; carnitine palmitoyltransferase 1a; (CPT1a), long-chain acyl-CoA dehydrogenase (LCAD), long-chain L-3-hydroxyacylcoenzyme A dehydrogenase alpha (HADHalpha), uncoupling protein 2 (UCP2), straight-chain acyl-CoA oxidase (ACOX), branched-chain acyl-CoA oxidase (BOX), cytochrome P450 2E1 (CYP2E1), CYP4A11, and peroxisome proliferator-activated receptor (PPAR)alpha for oxidation in the mitochondria, peroxisomes and microsomes; superoxide dismutase (SOD), catalase, and glutathione synthetase (GSS) for antioxidant pathways; and diacylglycerol O-acyltransferase 1 (DGAT1), PPARgamma, and hormone-sensitive lipase (HSL) for triglyceride synthesis and catalysis. In NAFLD, although fatty acids accumulated in hepatocytes, their de novo synthesis and uptake were up-regulated in association with increased expression of ACC1, FAS, SREBP-1c, and ADRP. Fatty acid oxidation-related genes, LCAD, HADHalpha, UCP2, ACOX, BOX, CYP2E1, and CYP4A11, were all overexpressed, indicating that oxidation was enhanced in NAFLD, whereas the expression of CTP1a and PPARalpha was decreased. Furthermore, SOD and catalase were also overexpressed, indicating that antioxidant pathways are activated to neutralize reactive oxygen species (ROS), which are overproduced during oxidative processes. The expression of DGAT1 was up-regulated without increased PPARgamma expression, whereas the expression of HSL was decreased. Our data indicated the following regarding NAFLD: i) increased de novo synthesis and uptake of fatty acids lead to further fatty acid accumulation in hepatocytes; ii) mitochondrial fatty acid oxidation is decreased or fully activated; iii) in order to complement the function of mitochondria (beta-oxidation), peroxisomal (beta-oxidation) and microsomal (omega-oxidation) oxidation is up-regulated to decrease fatty acid accumulation; iv) antioxidant pathways including SOD and catalase are enhanced to neutralize ROS overproduced during mitochondrial, peroxisomal, and microsomal oxidation; and v) lipid droplet formation is enhanced due to increased DGAT expression and decreased HSL expression. Further studies will be needed to clarify how fatty acid synthesis is increased by SREBP-1c, which is under the control of insulin and AMP-activated protein kinase. PMID:17671740

Kohjima, Motoyuki; Enjoji, Munechika; Higuchi, Nobito; Kato, Masaki; Kotoh, Kazuhiro; Yoshimoto, Tsuyoshi; Fujino, Tatsuya; Yada, Masayoshi; Yada, Ryoko; Harada, Naohiko; Takayanagi, Ryoichi; Nakamuta, Makoto

2007-09-01

330

CONVERSION OF OLEIC ACID TO BRANCHED-CHAIN FATTY ACIDS  

Technology Transfer Automated Retrieval System (TEKTRAN)

Oleic acid and linoleic acid are the most abundant fatty acids of cottonseed oil. As part of a project to develop new value-added industrial applications for cottonseed oil (such as biodiesel, fuel additives, and lubricants), studies were conducted in the synthetic conversion of oleic acid to branc...

331

AMPK-independent pathways regulate skeletal muscle fatty acid oxidation  

PubMed Central

The activation of AMP-activated protein kinase (AMPK) and phosphorylation/inhibition of acetyl-CoA carboxylase 2 (ACC2) is believed to be the principal pathway regulating fatty acid oxidation. However, during exercise AMPK activity and ACC Ser-221 phosphorylation does not always correlate with rates of fatty acid oxidation. To address this issue we have investigated the requirement for skeletal muscle AMPK in controlling aminoimidazole-4-carboxymide-1-?-d-ribofuranoside (AICAR) and contraction-stimulated fatty acid oxidation utilizing transgenic mice expressing a muscle-specific kinase dead (KD) AMPK ?2. In wild-type (WT) mice, AICAR and contraction increased AMPK ?2 and ?1 activities, the phosphorylation of ACC2 and rates of fatty acid oxidation while tending to reduce malonyl-CoA levels. Despite no activation of AMPK in KD mice, ACC2 phosphorylation was maintained, malonyl-CoA levels were reduced and rates of fatty acid oxidation were comparable between genotypes. During treadmill exercise both KD and WT mice had similar values of respiratory exchange ratio. These studies suggested the presence of an alternative ACC2 kinase(s). Using a phosphoproteomics-based approach we identified 18 Ser/Thr protein kinases whose phosphorylation was increased by greater than 25% in contracted KD relative to WT muscle. Utilizing bioinformatics we predicted that extracellular regulated protein-serine kinase (ERK1/2), inhibitor of nuclear factor (NF)-?B protein-serine kinase ? (IKK?) and protein kinase D (PKD) may phosphorylate ACC2 at Ser-221 but during in vitro phosphorylation assays only AMPK phosphorylated ACC2. These data demonstrate that AMPK is not essential for the regulation of fatty acid oxidation by AICAR or muscle contraction. PMID:18845612

Dzamko, Nicolas; Schertzer, Jonathan D; Ryall, James G; Steel, Rohan; Macaulay, S Lance; Wee, Sheena; Chen, Zhi-Ping; Michell, Belinda J; Oakhill, Jonathan S; Watt, Matthew J; Jørgensen, Sebastian Beck; Lynch, Gordon S; Kemp, Bruce E; Steinberg, Gregory R

2008-01-01

332

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

333

Fatty acid compositions of six wild edible mushroom species.  

PubMed

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

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

2013-01-01

334

Engineering oilseeds to produce nutritional fatty acids.  

PubMed

There is a growing body of evidence suggesting that regular consumption of foods rich in omega-3 long chain polyunsaturated fatty acids has multiple positive health benefits. The fats and oils from marine fish contain high contents of these beneficial fatty acids but increased consumer demand has also increased strain on the ability of the world's fisheries to meet demand from wild capture. Many consumers are choosing fish oil supplements or are eating foods that have been complemented with fish oils instead of consuming fish directly. However, removing undesirable odors, flavors and contaminants is expensive. In contrast, oils derived from land plants such as soybean are inexpensive and contaminant free. Recent strides in plant molecular biology now allow the engineering of oilseeds for the production of novel fats and oils, including those synthesized by complex, multigene biosynthetic pathways such as the omega-3 long chain polyunsaturated fatty acids. Given the potential benefits to the environment with regards to overfishing and the health prospects of increased consumption of these healthy fatty acids, producing these fatty acids in oilseeds is a desirable and worthy goal. In this review, we will describe the recent advances in this field along with some of the technical hurdles encountered thus far. PMID:18251865

Damude, Howard G; Kinney, Anthony J

2008-01-01

335

Antioxidant activity of phenolic compounds added to a functional emulsion containing omega-3 fatty acids and plant sterol esters.  

PubMed

The effect of eleven compounds extracted from red propolis on the oxidative stability of a functional emulsion was evaluated. Emulsions prepared with Echium oil as omega 3 (?-3 FA) source, containing 1.63g/100mL of ?-linolenic acid (ALA), 0.73g/100mL of stearidonic acid (SDA) and 0.65g/100mL of plant sterol esters (PSE) were prepared without or with phenolic compounds (vanillic acid, caffeic acid, trans-cinnamic acid, 2,4-dihydroxycinnamic acid, p-coumaric acid, quercetin, trans-ferulic acid, trans,trans-farnesol, rutin, gallic acid or sinapic acid). tert-Butylhydroquinone and a mixture containing ascorbic acid and FeSO4 were applied as negative and positive controls of the oxidation. Hydroperoxide, thiobarbituric acid reactive substances (TBARS), malondialdehyde and phytosterol oxidation products (POPs) were evaluated as oxidative markers. Based on hydroperoxide and TBARS analysis, sinapic acid and rutin (200ppm) showed the same antioxidant activity than TBHQ, representing a potential alternative as natural antioxidant to be applied in a functional emulsion containing ?-3 FA and PSE. PMID:25842314

Espinosa, Raquel Rainho; Inchingolo, Raffaella; Alencar, Severino Matias; Rodriguez-Estrada, Maria Teresa; Castro, Inar Alves

2015-09-01

336

[The effect of diet ratio of polyunsaturated fatty acids of omega-3 and omega-6 families on activity of aminotransferases and gamma-glutamyltransferase in rat blood serum].  

PubMed

The effect of diet fat compositions with various ratio of omega-3 and omega-6 polyunsaturated fatty acids (PUFAs) on alanine aminotransferase (ALT), aspartate aminotransferase (AST) and gamma-glutamyltransferase (GGT) activities in blood serum of 45 white mongrel rats weighing 90-110 g (9 animals in group) has been investigated. Fat components in the semi-synthetic diet, compiled on the basis of AIN-93 diet, and sources of omega-6 and omega-3 PUFA were presented by sunflower oil, soybean oil and fish oil. It has been shown that four-week inclusion of linoleic acid (LA) and alpha-linolenic acid (alpha-LNA) in a ratio of 7:1 into the diet (soybean oil) as well as use of only omega-6 PUFA (sunflower oil) has lead to an increase in the activity of ALT and GGT in rat blood serum compared to control animals treated with the complex of linolenic, eicosapentaenoic (EPA) and docosahexaenoic (DHA) acid through the mixture of sunflower oil and fish oil (9:1) with the ratio of omega-6 and omega-3 PUFA 7:1. Along with this, the AST:ALT ratio (de Ritis ratio) was lower (p < 0.05) as compared with the control group of rat, amounting respectively 0.92 +/- 0.08 and 0.79 +/- 0.12 vs 1.26 +/- 0.10. The use of high doses of omega-3 fatty acids (600 mg EPA and 400 mg DHA per kg of animal weight per day coming through fish oil) did not affect the activity of ALT and GGT, but increased AST serum activity (0.47 +/- 0.04 micromoles/min per mg protein) and the de Ritis ratio (2.53 +/- 0.23). The diet deprived with fat increased enzyme activity of ALT, AST and GGT in rat blood serum. PMID:25059053

Ketsa, O V; Marchenko, M M

2014-01-01

337

Effect of long-term administration of arachidonic acid on n-3 fatty acid deficient mice.  

PubMed

The effect of long-term oral administration of arachidonic acid (ARA, 240mg/kg/day) on brain function was assessed for mice maintained on an n-3 fatty acid adequate or deficient diet. The administration of ARA for 13 weeks resulted in an elevation of spontaneous motor activity, or the tendency thereof, in both the n-3 fatty acid adequate and deficient groups. However, the n-3 fatty acid deficient mice that were administered with ARA revealed marked deterioration in motor function in a motor coordination test. In the experiment to investigate changes over time, the motor activity of the ARA-administered group continued to increase mildly in n-3 deficient mice, although that of the control group showed a decrease involving habituation for both diet groups from the second week. The fatty acid composition of the brain at the end of the behavioral experiments indicated an increase in the levels of ARA and other n-6 fatty acids, as well as a decrease in the levels of docosahexaenoic acid. These results suggest that long-term administration of ARA causes an increase of futile spontaneous motor activity and the diminution of motor function by aggravation of n-3 fatty acid deficiency. PMID:25650363

Harauma, Akiko; Tomita, Makiko; Muto, Daiki; Moriguchi, Toru

2015-04-01

338

Molar extinction coefficients of some fatty acids  

NASA Astrophysics Data System (ADS)

The attenuation of gamma rays in some fatty acids, viz. formic acid (CH 2O 2), acetic acid (C 2H 4O 2), propionic acid (C 3H 6O 2), butyric acid (C 4H 8O 2), n-hexanoic acid (C 6H 12O 2), n-caprylic acid (C 8H 16O 2), lauric acid (C 12H 24O 2), myristic acid (C 14H 28O 2), palmitic acid (C 16H 32O 2), oleic acid (C 18H 34O 2) and stearic acid (C 18H 36O 2), has been measured at the photon energies 81, 356, 511, 662, 1173 and 1332 keV. Experimental values for the molar extinction coefficient, the effective atomic number and the electron density have been derived and compared with theoretical calculations. There is good agreement between experiment and theory.

Sandhu, G. K.; Singh, Kulwant; Lark, B. S.; Gerward, L.

2002-10-01

339

The significance of polyunsaturated fatty acids in cutaneous biology  

Microsoft Academic Search

The skin epidermis displays a highly active metabolism of polyunsaturated fatty acids (PUFA). Dietary deficiency of linoleic\\u000a acid (LA) and 18-carbon (n-6) PUFA results in characteristic scaly skin disorder and excessive epidermal water loss. Arachidonic\\u000a acid, a 20-carbon (n-6) PUFA is metabolized via the cyclooxygenase pathway into predominantly prostaglandin E2 (PGE2) PGF2?? and PGD2 and via the lipoxygenase pathway into

Vincent A. Ziboh

1996-01-01

340

Nicotine-induced activation of AMP-activated protein kinase inhibits fatty acid synthase in 3T3L1 adipocytes: a role for oxidant stress.  

PubMed

Recent studies suggest that the AMP-activated protein kinase (AMPK) acts as a major energy sensor and regulator in adipose tissues. The objective of this study was to investigate the role of AMPK in nicotine-induced lipogenesis and lipolysis in 3T3L1 adipocytes. Exposure of 3T3L1 adipocytes to smoking-related concentrations of nicotine increased lipolysis and inhibited fatty acid synthase (FAS) activity in a time- and dose-dependent manner. The effects of nicotine on FAS activity were accompanied by phosphorylation of both AMPK (Thr(172)) and acetyl-CoA carboxylase (ACC; Ser(79)). Nicotine-induced AMPK phosphorylation appeared to be mediated by reactive oxygen species based on the finding that nicotine significantly increased superoxide anions and 3-nitrotyrosine-positive proteins, exogenous peroxynitrite (ONOO(-)) mimicked the effects of nicotine on AMPK, and N-acetylcysteine (NAC) abolished nicotine-enhanced AMPK phosphorylation. Inhibition of AMPK using either pharmacologic (insulin, compound C) or genetic means (overexpression of dominant negative AMPK; AMPK-DN) abolished FAS inhibition induced by nicotine or ONOO(-). Conversely, activation of AMPK by pharmacologic (nicotine, ONOO(-), metformin, and AICAR) or genetic (overexpression of constitutively active AMPK) means inhibited FAS activity. Notably, AMPK activation increased threonine phosphorylation of FAS, and this effect was blocked by adenovirus encoding dominant negative AMPK. Finally, AMPK-dependent FAS phosphorylation was confirmed by (32)P incorporation into FAS in adipocytes. Taken together, our results strongly suggest that nicotine, via ONOO(-) activates AMPK, resulting in enhanced threonine phosphorylation and consequent inhibition of FAS. PMID:17635921

An, Zhibo; Wang, Hong; Song, Ping; Zhang, Miao; Geng, Xuemei; Zou, Ming-Hui

2007-09-14

341

AMP-activated protein kinase activation by AICAR increases both muscle fatty acid and glucose uptake in white muscle of insulin-resistant rats in vivo.  

PubMed

Insulin-stimulated glucose uptake is increased in white but not red muscle of insulin-resistant high-fat-fed (HF) rats after administration of the AMP-activated protein kinase (AMPK) activator 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside (AICAR). To investigate whether a lesser AICAR effect on glucose uptake in red muscle was offset by a greater effect on fatty acid (FA) uptake, we examined acute effects of AICAR on muscle glucose and FA fluxes in HF rats. HF rats received AICAR (250 mg/kg) subcutaneously. At 30 min, a mixture of either (3)H-(R)-2-bromopalmitate/(14)C-palmitate or (3)H-2-deoxyglucose/(14)C-glucose was administered intravenously to assess muscle FA and glucose uptake. AICAR decreased plasma levels of glucose (approximately 25%), insulin (approximately 60%), and FAs (approximately 30%) at various times over the next 46 min (P < 0.05 vs. controls). In white muscle, AICAR increased both FA (2.4-fold) and glucose uptake (4.9-fold), associated with increased glycogen synthesis (6-fold). These effects were not observed in red muscle. We conclude that both glucose and FA fluxes are enhanced by AICAR more in white versus red muscle, consistent with the relative degree of activation of AMPK. Therefore, a lesser effect of AICAR to alleviate muscle insulin resistance in red versus white muscle is not explained by a relatively greater effect on FA uptake in the red muscle. PMID:15220186

Iglesias, Miguel A; Furler, Stuart M; Cooney, Gregory J; Kraegen, Edward W; Ye, Ji-Ming

2004-07-01

342

Betulinic acid alleviates non-alcoholic fatty liver by inhibiting SREBP1 activity via the AMPK-mTOR-SREBP signaling pathway.  

PubMed

Non-alcoholic fatty liver disease (NAFLD) is emerging as the most common liver disease in industrialized countries. The discovery of food components that can ameliorate NAFLD is therefore of interest. Betulinic acid (BA) is a triterpenoid with many pharmacological activities, but the effect of BA on fatty liver is as yet unknown. To explore the possible anti-fatty liver effects and their underlying mechanisms, we used insulin-resistant HepG2 cells, primary rat hepatocytes and liver tissue from ICR mice fed a high-fat diet (HFD). Oil Red O staining revealed that BA significantly suppressed excessive triglyceride accumulation in HepG2 cells and in the livers of mice fed a HFD. Ca(+2)-calmodulin dependent protein kinase kinase (CAMKK) and AMP-activated protein kinase (AMPK) were both activated by BA treatment. In contrast, the protein levels of sterol regulatory element-binding protein 1 (SREBP1), mammalian target of rapamycin (mTOR) and S6 kinase (S6K) were all reduced when hepatocytes were treated with BA for up to 24h. We found that BA activates AMPK via phosphorylation, suppresses SREBP1 mRNA expression, nuclear translocation and repressed SREBP1 target gene expression in HepG2 cells and primary hepatocytes, leading to reduced lipogenesis and lipid accumulation. These effects were completely abolished in the presence of STO-609 (a CAMKK inhibitor) or compound C (an AMPK inhibitor), indicating that the BA-induced reduction in hepatic steatosis was mediated via the CAMKK-AMPK-SREBP1 signaling pathway. Taken together, our results suggest that BA effectively ameliorates intracellular lipid accumulation in liver cells and thus is a potential therapeutic agent for the prevention of fatty liver disease. PMID:23435355

Quan, Hai Yan; Kim, Do Yeon; Kim, Soo Jung; Jo, Hee Kyung; Kim, Go Woon; Chung, Sung Hyun

2013-05-01

343

Improvements in glucose tolerance and insulin sensitivity after lifestyle intervention are related to changes in serum fatty acid profile and desaturase activities: the SLIM study  

Microsoft Academic Search

Aims\\/hypothesis  The aim of this study was to investigate whether lifestyle intervention-induced changes in serum fatty acid profile of cholesteryl\\u000a esters and estimated desaturase activities are related to improvements in insulin sensitivity in subjects at risk of type\\u000a 2 diabetes.\\u000a \\u000a \\u000a \\u000a Materials and methods  In the Study on Lifestyle Intervention and Impaired Glucose Tolerance Maastricht (SLIM), 97 men and women with IGT were

E. Corpeleijn; E. J. M. Feskens; E. H. J. M. Jansen; M. Mensink; W. H. M. Saris; T. W. A. de Bruin; E. E. Blaak

2006-01-01

344

The fatty acids of dormant tung buds  

Microsoft Academic Search

Conclusions and Summary  The methyl esters of the fatty acids in the wax of dormant tung buds were prepared and fractionated in a column packed with\\u000a a spiral screen. Myristic, palmitic, linoleic, oleic, and stearic acids were identified in some of the fractions by the saponification\\u000a equivalents and by the melting points of the p-bromophenacyl derivatives of the saturated acids and

Harold M. Sell; Seymour G. Gilbert

1947-01-01

345

Oxygenated fatty acid constituents of soybean phosphatidylcholines  

Microsoft Academic Search

Bitter-tasting phosphatidylcholines from hexane-defatted soybean flakes were chromatographically separable from ordinary soy\\u000a phosphatidylcholines (SPC). The bitter-tasting SPC contain 32% oxygenated fatty acids in addition to palmitic, stearic, oleic,\\u000a linoleic, and linolenic acids. Identification of these oxygenated acids was based on infrared, ultraviolet, proton nuclear\\u000a magnetic resonance, and mass spectral characteristics of methyl ester derivatives which were separated and purified by

D. J. Sessa; H. W. Gardner; R. Kleiman; D. Weisleder

1977-01-01

346

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

347

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

348

Enhancement of polyunsaturated fatty acid production by cerulenin treatment in polyunsaturated fatty acid-producing bacteria  

Microsoft Academic Search

When docosahexaenoic acid (DHA)-producing Moritella marina strain MP-1 was cultured in the medium containing 0.5 ? g cerulenin ml?1, an inhibitor for fatty acid biosynthesis, the cells grew normally, but the?content of DHA in the total fatty acids increased from 5.9–19.4%. The DHA yield of M. marina strain MP-1 cells also increased from 4 to 13.7 mg l?1 by cerulenin treatment.

Naoki Morita; Takanori Nishida; Mika Tanaka; Yutaka Yano; Hidetoshi Okuyama

2005-01-01

349

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

350

Very long chain fatty acid synthesis in sunflower kernels.  

PubMed

Most common seed oils contain small amounts of very long chain fatty acids (VLCFAs), the main components of oils from species such as Brassica napus or Lunnaria annua. These fatty acids are synthesized from acyl-CoA precursors in the endoplasmic reticulum through the activity of a dissociated enzyme complex known as fatty acid elongase. We studied the synthesis of the arachidic, behenic, and lignoceric VLCFAs in sunflower kernels, in which they account for 1-3% of the saturated fatty acids. These VLCFAs are synthesized from 18:0-CoA by membrane-bound fatty acid elongases, and their biosynthesis is mainly dependent on NADPH equivalents. Two condensing enzymes appear to be responsible for the synthesis of VLCFAs in sunflower kernels, beta-ketoacyl-CoA synthase-I (KCS-I) and beta-ketoacyl-CoA synthase-II (KCS-II). Both of these enzymes were resolved by ion exchange chromatography and display different substrate specificities. While KCS-I displays a preference for 20:0-CoA, 18:0-CoA was more efficiently elongated by KCS-II. Both enzymes have different sensitivities to pH and Triton X-100, and their kinetic properties indicate that both are strongly inhibited by the presence of their substrates. In light of these results, the VLCFA composition of sunflower oil is considered in relation to that in other commercially exploited oils. PMID:15796615

Salas, Joaquín J; Martínez-Force, Enrique; Garcés, Rafael

2005-04-01

351

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...

352

Resistance to Freezing and Frozen Storage of Streptococcus thermophilus Is Related to Membrane Fatty Acid Composition  

Microsoft Academic Search

The resistance to freezing and frozen storage of Strep- tococcus thermophilus was related to the fatty acid com- position of the cell membrane. The effects of four experi- mental factors were investigated on the fatty acid con- centrations and on the recovery of acidification activity of S. thermophilus stored at ?20°C by using a complete experimental design: incorporating oleic acid

C. Beal; F. Fonseca; G. Corrieu

2001-01-01

353

Current Progress and Future Research on the Production of Oxygenated Fatty Acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

Oxygenated (hydroxy-, epoxy-) fatty acids such as ricinoleic, vernolic and /or sebacic acids are high value chemicals and can be used to produce polymers and specialty chemicals. Oxygenated fatty acids also have many bioactive properties, such as antimicrobial activity against Salmonella, Staphyloc...

354

Differential regulation of placental amino acid transport by saturated and unsaturated fatty acids.  

PubMed

Fatty acids are critical for normal fetal development but may also influence placental function. We have previously reported that oleic acid (OA) stimulates amino acid transport in primary human trophoblasts (PHTs). In other tissues, saturated and unsaturated fatty acids have distinct effects on cellular signaling, for instance, palmitic acid (PA) but not OA reduces I?B? expression. We hypothesized that saturated and unsaturated fatty acids differentially affect trophoblast amino acid transport and cellular signaling. To test this hypothesis, PHTs were cultured in docosahexaenoic acid (DHA; 50 ?M), OA (100 ?M), or PA (100 ?M). DHA and OA were also combined to test whether DHA could counteract the OA stimulatory effect on amino acid transport. The effects of fatty acids were compared against a vehicle control. Amino acid transport was measured by isotope-labeled tracers. Activation of inflammatory-related signaling pathways and the mechanistic target of rapamycin (mTOR) pathway were determined by Western blot analysis. Exposure of PHTs to DHA for 24 h reduced amino acid transport and phosphorylation of p38 MAPK, STAT3, mTOR, eukaryotic initiation factor 4E-binding protein 1, and ribosomal protein (rp)S6. In contrast, OA increased amino acid transport and phosphorylation of ERK, mTOR, S6 kinase 1, and rpS6. The combination of DHA with OA increased amino acid transport and rpS6 phosphorylation. PA did not affect amino acid transport but reduced I?B? expression. In conclusion, these fatty acids differentially regulated placental amino acid transport and cellular signaling. Taken together, these findings suggest that dietary fatty acids could alter the intrauterine environment by modifying placental function, thereby having long-lasting effects on the developing fetus. PMID:25143349

Lager, Susanne; Jansson, Thomas; Powell, Theresa L

2014-10-15

355

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

356

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

PubMed Central

Background 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. Results 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. Conclusions 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. PMID:21612656

2011-01-01

357

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

358

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

359

Detection and Quantification of Protein Adduction by Electrophilic Fatty Acids: Mitochondrial Generation of Fatty Acid Nitroalkene Derivatives  

PubMed Central

Nitroalkene fatty acid derivatives manifest a strong electrophilic nature, are clinically detectable and induce multiple transcriptionally-regulated anti-inflammatory responses. At present, the characterization and quantification of endogenous electrophilic lipids is compromised by their Michael addition with protein and small molecule nucleophilic targets. Herein, we report a trans-nitroalkylation reaction of nitro-fatty acids with ?-mercaptoethanol (BME) and apply this reaction to the unbiased identification and quantification of reaction with nucleophilic targets. Trans-nitroalkylation yields are maximal at pH 7 to 8, and occur with physiological concentrations of target nucleophiles. This reaction also amenable to sensitive mass spectrometry-based quantification of electrophilic fatty acid-protein adducts upon electrophoretic resolution of proteins. In-gel trans-nitroalkylation reactions also permit the identification of protein targets without the bias and lack of sensitivity of current proteomic approaches. Using this approach, it was observed that fatty acid nitroalkenes are rapidly metabolized in vivo by a nitroalkene reductase activity and mitochondrial ?-oxidation, yielding a variety of electrophilic and non-electrophilic products that could be structurally characterized upon BME-based transnitroalkylation reaction. This strategy was applied to the detection and quantification of fatty acid nitration in mitochondria in response to oxidative inflammatory conditions induced by myocardial ischemia-reoxygenation. PMID:19353781

Schopfer, F.J.; Batthyany, C.; Baker, P.R.S.; Bonacci, G.; Cole, M.P.; Rudolph, V.; Groeger, A.; Rudolph, T.K.; Nadtochiy, S.; Brookes, P.S.; Freeman, B.A.

2011-01-01

360

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2010 CFR

40 Protection of Environment 30 2010-07-01 ...Triethanolamine salts of fatty acids. 721.3629 Section 721.3629 Protection of Environment ENVIRONMENTAL PROTECTION...Triethanolamine salts of fatty acids. (a) Chemical...

2010-07-01

361

40 CFR 721.3627 - Branched synthetic fatty acid.  

Code of Federal Regulations, 2010 CFR

40 Protection of Environment 30 2010-07-01 ...Branched synthetic fatty acid. 721.3627 Section 721.3627 Protection of Environment ENVIRONMENTAL PROTECTION...Branched synthetic fatty acid. (a) Chemical...

2010-07-01

362

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2011 CFR

40 Protection of Environment 31 2011-07-01 ...Triethanolamine salts of fatty acids. 721.3629 Section 721.3629 Protection of Environment ENVIRONMENTAL PROTECTION...Triethanolamine salts of fatty acids. (a) Chemical...

2011-07-01

363

40 CFR 721.3627 - Branched synthetic fatty acid.  

Code of Federal Regulations, 2011 CFR

40 Protection of Environment 31 2011-07-01 ...Branched synthetic fatty acid. 721.3627 Section 721.3627 Protection of Environment ENVIRONMENTAL PROTECTION...Branched synthetic fatty acid. (a) Chemical...

2011-07-01

364

Fatty acids in cell signaling: Historical perspective and future outlook.  

PubMed

Fatty acids are not only important metabolic substrates and building blocks of lipids but are also increasingly being recognized for their modulatory roles in a wide variety of cellular processes including gene expression, together referred to as the 'message-modulator' function of fatty acids. Crucial for this latter role is the bioavailability of fatty acids, which is governed by their interaction with soluble proteins capable of binding fatty acids, i.e., plasma albumin and cytoplasmic fatty acid-binding protein (FABPc), and with both the lipid and protein components of biological membranes, including membrane-associated fatty acid-binding proteins such as the transmembrane protein CD36. Manipulating fatty acid availability holds promise as therapeutic approach for chronic diseases that are characterized by a perturbed fatty acid metabolism. PMID:24690372

Glatz, Jan F C; Luiken, Joost J F P

2015-01-01

365

65 FR 10396 - Polyoxyethylated Sorbitol Fatty Acid Esters; Tolerance Exemption  

Federal Register 2010, 2011, 2012, 2013, 2014

...FRL-6490-8] RIN 2070-AB78 Polyoxyethylated Sorbitol Fatty Acid Esters; Tolerance Exemption AGENCY...for residues of the polymers polyoxyethylated sorbitol fatty acid esters; the sorbitol solution containing up to 15% water is...

2000-02-28

366

Immunomodulation by Polyunsaturated Fatty Acids: Mechanisms and Effects  

Microsoft Academic Search

Polyunsaturated fatty acids (PUFAs) modulate immune responses, thereby exerting beneficial effects in a variety of inflammatory disorders. PUFAs of the n-3 series that are found in marine fish oils are particularly effective. A variety of molecular mechanisms have been found to explain how PUFAs could interfere with immune cell function. PUFAs alter eicosanoid (prostaglandin, leukotriene) synthesis, orphan nuclear receptor activation

Thomas M. Stulnig

2003-01-01

367

Elevated serum free fatty acid concentrations inhibit T lymphocyte signaling  

Microsoft Academic Search

Unbound cis-unsaturated free (i.e., nonesterified) fatty acids (FFA) inhibit T lymphocyte activation in vitro and therefore may exert immuno- suppressive effects. However, in blood serum the major proportion of FFA is tightly bound to albumin, whereas unbound FFA are hardly detectable. Since serum FFA elevation occurs under pathological con- ditions like insulin resistance or cancer, which are often associated with

THOMAS M. STULNIG; MARKUS BERGER; MICHAEL RODEN; HARALD STINGL; DANIEL RAEDERSTORFF; WERNER WALDHAUSL

368

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

369

Fatty Acids as Surfactants on Aerosol Particles  

NASA Astrophysics Data System (ADS)

Fatty acids (n-alcanoic acids) are common compounds in numerous anthropogenic and natural emissions. According to Rogge et al. (1993), catalyst-equipped automobiles emitted more than 600 ?g km-1 of fatty acids which was over 50% of all identified organics in fine aerosol emissions. Coal burning produces fatty acids ranging from about 1700 mg kg-1 for bituminous coal to over 10000 mg kg-1 for lignite (Oros and Simoneit, 2000). Similarly, biomass burning is an important source for aerosol fatty acids. They are the major identified compound group in deciduous tree smoke, their total emission factor being measured as 1589 mg kg-1 which was 56% of all identified organic compounds (Oros and Simoneit, 2001a). Large amounts of fatty acid are also emitted from burning of conifer trees and grass (Oros and Simoneit, 2001a; Simoneit, 2002). Fatty acids have been reported to be major constituents of marine aerosols in many investigations (Barger and Garrett, 1976; Gagosian et. al, 1981; Sicre et al., 1990; Stephanou, 1992). It has been suggested that as the marine aerosol particles form, they acquire a coating of organic surfactants (Blanchard, 1964; Gill et al., 1983; Middlebrook et al., 1998; Ellison et al., 1999). Amphiphilic molecules, including lipids, can be assembled as monomolecular layers at air/water interfaces as well as transported to a solid support. Recently, we could show by time-of-flight secondary ion mass spectrometry that fatty acids are important ingredients of the outermost surface layer of the sea-salt aerosol particles (Tervahattu et al., 2002). In their TOF-SIMS studies on the surface composition of atmospheric aerosols, Peterson and Tyler (2002) found fatty acids on the surface of Montana forest fire particles. In this work we have studied by TOF-SIMS the surface chemical composition of aerosol particles emitted from field fires in the Baltic and other East European countries and transported to Finland as well as aerosol particles transported from Russian forest and peat fires. Fatty acids were commonly observed on the surface layer of these particles. The chain length composition was characteristic to each emission source. In our previous work (Tervahattu et al., 2002), fatty acids on sea-salt particles were originated from dead sea plankton organisms with major peaks ranging from C14 to C18 and maximum at C16 (palmitic acid). Major peaks on the surface of forest fire particles ranged from C16 to C30 with the maximum at C24. This composition indicates the involvement of the smoke from both conifer trees and peat (Oros and Simoneit, 2000; 2001b). On the other hand, TOF-SIMS analysis of the surface of field fire particles showed major peaks from C14 to C30 with two maximums at C16 (highest intensity) and C22. It was concluded that the results indicate emissions from both grass burning and fossil fuels (Simoneit, 2002; Oros and Simoneit, 2000). The presence of surface film on aerosol particles may have an impact on their chemical, physical and optical properties and change their role in light scattering and as cloud condensation nuclei as well as interactions with human tissue.

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

2003-12-01

370

Evidence for dissolution of fatty acids in sediment traps: Impact on flux estimates  

NASA Astrophysics Data System (ADS)

The effect of dissolution from particulates into the supernatant solution in sediment trap sample cups has been measured for fatty acids. A mooring array with time series sediment traps was deployed in the northeast Atlantic Ocean (59°N, 21°W) for 14 months. Selected representative samples from the trap at 2200 m (poisoned with NaN3) were analyzed for total and free fatty acids in both the solution and particulate phase by means of gas chromatography-mass spectrometry with an ion trap detector. The flux contribution of the dissolved total fatty acids (? DTFA) was found to be between 15 and 75% of the total flux (? TTFA, sum of the fluxes of total fatty acids in both particles and supernatants). Dissolved free fatty acids (? DFFA) represented 25-88% of the total flux of free fatty acids (? TFFA). Absolute concentrations of total and free fatty acids in both compartments are discussed in terms of the processes controlling the distribution between the two phases, for example, readsorption. Sample handling, poisoning, bacterial activity, and swimmers may also affect fatty acid distribution. Flux data (sum of particulate and dissolved fluxes) are presented for individual fatty acids. Also, the degree of dissolution of individual fatty acids is shown for one sample (dissolved fraction ranging between 16 and 98% of total flux).

KöRtzinger, Arne; Schulz-Bull, Detlef E.; Petrick, Gert; Duinker, Jan C.

1994-02-01

371

Reduced total energy expenditure and physical activity in cachectic patients with pancreatic cancer can be modulated by an energy and protein dense oral supplement enriched with n-3 fatty acids  

Microsoft Academic Search

The aim of the study was to assess the total energy expenditure (TEE), resting energy expenditure (REE) and physical activity level (PAL) in home-living cachectic patients with advanced pancreatic cancer. The influence of an energy and protein dense oral supplement either enriched with or without the n-3 fatty acid eicosapentaenoic acid (EPA) and administered over an 8-week period was also

A W G Moses; C Slater; T Preston; M D Barber; K C H Fearon; KCH Fearon

2004-01-01

372

Plasma Acylcarnitine Profiles Suggest Incomplete Fatty Acid ß-Oxidation and Altered Tricarboxylic Cycle Activity in Type 2 Diabetic African-American Women  

Technology Transfer Automated Retrieval System (TEKTRAN)

Inefficient muscle long-chain fatty acid (LCFA) combustion is associated with insulin resistance, but molecular links between mitochondrial fat catabolism and insulin action remain controversial. We hypothesized that plasma acylcarnitine profiling would identify distinct metabolite patterns reflect...

373

Insulin restores fatty acid composition earlier in liver microsomes than erythrocyte membranes in streptozotocin-induced diabetic rats  

Microsoft Academic Search

Alterations of fatty acid composition have been observed in a number of tissues in both experimental and human diabetes. Suppression of ?6 desaturase in the liver, a key enzyme of fatty acid desaturation, has been reported to be responsible for these phenomena. We measured the fatty acid composition of the liver and the erythrocytes, and examined ?6 desaturase activities to

C. S. Shin; M. K. Lee; K. S. Park; S. Y. Kim; B. Y. Cho; H. K. Lee; C.-S. Koh; H. K. Min

1995-01-01

374

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...

375

Interleukin-6 increases insulin-stimulated glucose disposal in humans and glucose uptake and fatty acid oxidation in vitro via AMP-activated protein kinase.  

PubMed

Although interleukin-6 (IL-6) has been associated with insulin resistance, little is known regarding the effects of IL-6 on insulin sensitivity in humans in vivo. Here, we show that IL-6 infusion increases glucose disposal without affecting the complete suppression of endogenous glucose production during a hyperinsulinemic-euglycemic clamp in healthy humans. Because skeletal muscle accounts for most of the insulin-stimulated glucose disposal in vivo, we examined the mechanism(s) by which IL-6 may affect muscle metabolism using L6 myotubes. IL-6 treatment increased fatty acid oxidation, basal and insulin-stimulated glucose uptake, and translocation of GLUT4 to the plasma membrane. Furthermore, IL-6 rapidly and markedly increased AMP-activated protein kinase (AMPK). To determine whether the activation of AMPK mediated cellular metabolic events, we conducted experiments using L6 myotubes infected with dominant-negative AMPK alpha-subunit. The effects described above were abrogated in AMPK dominant-negative-infected cells. Our results demonstrate that acute IL-6 treatment enhances insulin-stimulated glucose disposal in humans in vivo, while the effects of IL-6 on glucose and fatty acid metabolism in vitro appear to be mediated by AMPK. PMID:17003332

Carey, Andrew L; Steinberg, Gregory R; Macaulay, S Lance; Thomas, Walter G; Holmes, Anna G; Ramm, Georg; Prelovsek, Oja; Hohnen-Behrens, Cordula; Watt, Matthew J; James, David E; Kemp, Bruce E; Pedersen, Bente K; Febbraio, Mark A

2006-10-01

376

Digestion and absorption of polyunsaturated fatty acids  

E-print Network

and in- flammatory diseases. Dietary sources of essential fatty acids are vegetable oils for either, and to some authors explains differences observed between vegetable and fish oil absorption. So additional, Absorption and Food Science, 11-13 September 1990, held under the auspices of the Association Française de

Boyer, Edmond

377

Plasma Fatty Acid Profile and Alternative Nutrition  

Microsoft Academic Search

Plasma profile of fatty acids was examined in a group of children consisting of 7 vegans, 15 lactoovovegetarians and 10 semivegetarians. The children were 11-15 years old and the average period of alternative nutrition was 3.4 years. The results were compared with a group of 19 omnivores that constituted an average sample with respect to biochemical and hematological parameters from

A. Béderová; J. Klvanová

1997-01-01

378

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

379

Lipid and fatty acid requirements of tilapias  

Technology Transfer Automated Retrieval System (TEKTRAN)

Tilapia have been shown to have a dietary requirement for linoleic (n-6) series fatty acids (18:2n-6 or 20:4n-6). The optimum dietary levels of n-6 reported were 0.5 and 1% for redbelly tilapia (Tilapia zillii) and Nile tilapia (Oreochromis niloticus), respectively. Tilapia have been suggested to al...

380

Polyunsaturated fatty acids and gene expression  

Technology Transfer Automated Retrieval System (TEKTRAN)

Purpose of review. This review focuses on the effect(s) of n-3 polyunsaturated fatty acids (PUFA) on gene transcription as determined from data generated using cDNA microarrays. Introduced within the past decade, this methodology allows detection of the expression of thousands of genes simultaneo...

381

OMEGA-3 FATTY ACID SUPPLEMENTATION AND SLEEP  

E-print Network

symptoms. Participants were randomly assigned either to a treatment condition, with a daily supplement of 1500 mg omega-3 fatty acid and 30 IU of vitamin E, or a control group that received 30 IU daily of vitamin E. Sleep was monitored over a 28 day period...

Prohaska, Jennifer A.

2008-10-24

382

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...

383

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

384

Fat deposition, fatty acid composition and meat quality: A review  

Microsoft Academic Search

This paper reviews the factors affecting the fatty acid composition of adipose tissue and muscle in pigs, sheep and cattle and shows that a major factor is the total amount of fat. The effects of fatty acid composition on meat quality are also reviewed. Pigs have high levels of polyunsaturated fatty acids (PUFA), including the long chain (C20-22) PUFA in

J. D. Wood; M. Enser; A. V. Fisher; G. R. Nute; P. R. Sheard; R. I. Richardson; S. I. Hughes; F. M. Whittington

2008-01-01

385

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

386

21 CFR 172.863 - Salts of fatty acids.  

Code of Federal Regulations, 2011 CFR

...3 2011-04-01 2011-04-01 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...

2011-04-01

387

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

388

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

389

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...

390

Selective mobilisation of fatty acids from human adipose tissue  

Microsoft Academic Search

Background: Adipose tissue is a storage organ for dietary fat. During fasting, fatty acids are released into serum as free fatty acids (FFA). Experimental studies indicate that fatty acids are selectively mobilised from adipose tissue into serum. The aim of this study was to investigate whether the composition of the serum FFA fraction reflects selective mobilisation in the fasting state

Paula Yli-Jama; Thomas S. Haugen; Hege M. Rebnord; Jetmund Ringstad; Jan I. Pedersen

2001-01-01

391

21 CFR 172.863 - Salts of fatty acids.  

Code of Federal Regulations, 2010 CFR

...2010-04-01 2009-04-01 true Salts of fatty acids. 172.863 Section 172.863 Food and...Multipurpose Additives § 172.863 Salts of fatty acids. The food additive salts of fatty acids may be safely used in food and in the...

2010-04-01

392

21 CFR 172.859 - Sucrose fatty acid esters.  

Code of Federal Regulations, 2010 CFR

...2010-04-01 2009-04-01 true Sucrose fatty acid esters. 172.859 Section 172.859 Food and...Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified in this section may be...

2010-04-01

393

21 CFR 172.854 - Polyglycerol esters of fatty acids.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 true Polyglycerol esters of fatty acids. 172.854 Section 172.854 Food and Drugs...Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol esters of fatty acids, up to and including the decaglycerol...

2010-04-01

394

21 CFR 172.848 - Lactylic esters of fatty acids.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 true Lactylic esters of fatty acids. 172.848 Section 172.848 Food and Drugs...Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty