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1

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.

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

1967-01-01

2

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

Microsoft Academic Search

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

Seung Hun Cha; Zhiyuan Hu; Shigeru Chohnan

2005-01-01

3

Influence of Unsaturation on Fibrinolytic Activity of Fatty Acids.  

National Technical Information Service (NTIS)

Long-chain saturated fatty acids are known to accelerate blood clotting and artificial thrombus formation in vitro, and to produce massive thrombosis and death in dogs and mice. We have found that some long-chain fatty acids induce fibrinolytic activity o...

M. J. Surgalla E. D. Beesley R. R. Brubaker

1967-01-01

4

Elevated expression of fatty acid synthase and fatty acid synthetic activity in colorectal neoplasia.  

PubMed Central

Expression of the primary enzyme catalyzing the synthesis of fatty acids, ie, fatty acid synthase (FAS), and ex vivo fatty acid synthetic activity were examined in colorectal epithelium and neoplasms, including the relationship to tumor progression and prognosis. Immunohistochemistry for FAS showed only faint staining of native colorectal mucosa, but increased expression was found in all sporadic adenomas (n = 18), adenomas associated with familial adenomatous polyposis (n = 7), hyperplastic polyps (n = 3), dysplasias arising in ulcerative colitis (n = 17), and colorectal carcinomas (n = 130) including 11 with contiguous adenomas. The intensity of staining was strong in 53% of carcinomas, intermediate in 38%, and weak in 9%. Activity of the fatty acid synthetic pathway measured by labeling of six surgical specimens with [U-14C]acetate was 2- to 7-fold higher in colorectal carcinomas than adjacent native mucosa (P = 0.006) and 6- to 16-fold higher than serosal fat (P = 0.01). Activity correlated with immunohistochemical expression (Spearman's rank correlation coefficient = 0.85; P < 0.001). There was no statistically significant association between patient survival and FAS staining intensity of carcinomas. Our study shows that FAS is expressed in all colorectal neoplasms and there is a concomitant increase in fatty acid synthesis. FAS may therefore represent a potential therapeutic target. Images Figure 1

Rashid, A.; Pizer, E. S.; Moga, M.; Milgraum, L. Z.; Zahurak, M.; Pasternack, G. R.; Kuhajda, F. P.; Hamilton, S. R.

1997-01-01

5

Activation of polyunsaturated fatty acids by rat tissues in vitro  

SciTech Connect

The conversion of labeled palmitic, linoleic, arachidonic and docosahexaenoic acids to their respective acyl CoA's was studied in homogenates and microsomes of rat tissues. The highest activity, both in homogenates and microsomes, was seen in liver and heart. There was moderate activity in retina, brain, lung, kidney and testes and the lowest activity was found in spleen. Docosahexaenoic acid was activated much less actively in heart tissue than the other fatty acids. In all tissues examined, the highest activation was observed with arachidonic acid and the lowest with docosahexaenoic acid. Except for liver, those tissues that contained high levels of docosahexaenoic acid also had the highest activation capacity for this fatty acid.

Reddy, T.S.; Bazan, N.G.

1984-12-01

6

Activation of fatty acids by non-glyoxysomal peroxisomes  

Microsoft Academic Search

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

H. Gerbling; B. Gerhardt

1987-01-01

7

The role of fatty acids and caveolin-1 in tumor necrosis factor ?–induced endothelial cell activation  

Microsoft Academic Search

Hypertriglyceridemia and associated high circulating free fatty acids are important risk factors for atherosclerosis. In contrast to omega-3 fatty acids, linoleic acid, the major omega-6 unsaturated fatty acid in the American diet, may be atherogenic by amplifying an endothelial inflammatory response. We hypothesize that omega-6 and omega-3 fatty acids can differentially modulate tumor necrosis factor ? (TNF-?)–induced endothelial cell activation

Lei Wang; Eun-Jin Lim; Michal Toborek; Bernhard Hennig

2008-01-01

8

Electrophilic Fatty Acids Regulate Matrix Metalloproteinase Activity and Expression*  

PubMed Central

Nitro-fatty acids (NO2-FA) are electrophilic signaling mediators formed by reactions of nitric oxide and nitrite. NO2-FA exert anti-inflammatory signaling actions through post-translational protein modifications. We report that nitro-oleic acid (OA-NO2) stimulates proMMP-7 and proMMP-9 proteolytic activity via adduction of the conserved cysteine switch domain thiolate. Biotin-labeled OA-NO2 showed this adduction occurs preferentially with latent forms of MMP, confirming a role for thiol alkylation by OA-NO2 in MMP activation. In addition to regulating pro-MMP activation, MMP expression was modulated by OA-NO2 via activation of peroxisome proliferator-activated receptor-?. MMP-9 transcription was decreased in phorbol 12-myristate 13-acetate-stimulated THP-1 macrophages to an extent similar to that induced by the peroxisome proliferator-activated receptor-? agonist Rosiglitazone. This was affirmed using a murine model of atherosclerosis, ApoE?/? mice, where in vivo OA-NO2 administration suppressed MMP expression in atherosclerotic lesions. These findings reveal that electrophilic fatty acid derivatives can serve as effectors during inflammation, first by activating pro-MMP proteolytic activity via alkylation of the cysteine switch domain, and then by transcriptionally inhibiting MMP expression, thereby limiting the further progression of inflammatory processes.

Bonacci, Gustavo; Schopfer, Francisco J.; Batthyany, Carlos I.; Rudolph, Tanja K.; Rudolph, Volker; Khoo, Nicholas K. H.; Kelley, Eric E.; Freeman, Bruce A.

2011-01-01

9

Influence of ethylenediaminetetraacetic acid (EDTA) on the bactericidal activity of fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

The effect of ethylenediaminetetraacetic acid (EDTA) on the bactericidal activity of alkaline salts of fatty acids was examined. A 0.5 M concentration of caproic, caprylic, capric, and lauric acids was dissolved in 1.0 M potassium hydroxide (KOH), and then supplemented with 0, 5, or 10 mM of EDTA. T...

10

The inhibition of endothelial activation by unsaturated fatty acids.  

PubMed

Dietary long-chain fatty acids (FA) may influence pathological processes involving endothelial activation and leukocyte-endothelial interactions, such as inflammation and atherosclerosis. We previously showed that the n-3 FA docosahexaenoate (22:6n-3, DHA) inhibits cytokine-stimulated expression of endothelial-leukocyte adhesion molecules and soluble cytokines in the range of nutritionally achievable plasma concentrations. More recently we assessed structural determinants of VCAM-1 inhibition by FA. Cultured endothelial cells were incubated first with various saturated, monounsaturated, n-6 or n-3 polyunsaturated FA alone and then together with interleukin-1 or tumor necrosis factor. Saturated FA did not inhibit cytokine-induced endothelial activation, while a progressive increase in inhibitory activity was observed, for the same chain length, with the increase in double bonds accompanying the transition from monounsaturates to n-6 and, further, to n-3 FA. Comparison of various FA indicated no role of the double-bond position or configuration; the greater number of double bonds could explain the greater inhibitory activity of n-3 vs. n-6 FA. In order to ascertain mechanisms for these effects, we demonstrated inhibition of nuclear factor-kappaB (NF-kappaB) activation by DHA in parallel with a reduction in hydrogen peroxide (a critical mediator of NF-kappaB activation) released by endothelial cells either extracellularly or intracellularly. This suggests that a property related to fatty acid peroxidability (the presence of multiple double bonds) is related to inhibitory properties of hydrogen peroxide release and, consequently, of endothelial activation. PMID:10419145

De Caterina, R; Spiecker, M; Solaini, G; Basta, G; Bosetti, F; Libby, P; Liao, J

1999-01-01

11

Antimicrobial activity of fatty acid methyl esters of some members of Chenopodiaceae.  

PubMed

Fatty acid methyl ester (FAME) extracts of four halophytic plants, viz. Arthrocnemum indicum, Salicornia brachiata, Suaeda maritima and Suaeda monoica belonging to the family Chenopodiaceae, were prepared and their composition was analyzed by GC-MS. The FAME extracts were also screened for antibacterial and antifungal activities. The GC-MS analysis revealed the presence of more saturated fatty acids than unsaturated fatty acids. Among the fatty acids analyzed, the relative percentage of lauric acid was high in S. brachiata (61.85%). The FAME extract of S. brachiata showed the highest antibacterial and antifungal activities among the extracts tested. The other three extracts showed potent antibacterial and moderate anticandidal activities. PMID:18669016

Chandrasekaran, Manivachagam; Kannathasan, Krishnan; Venkatesalu, Venugopalan

12

Fatty acid activation of peroxisome proliferator-activated receptor (PPAR)  

Microsoft Academic Search

Peroxisome proliferators such as clofibric acid, nafenopin, and WY-14,643 have been shown to activate peroxisome proliferator-activated receptor (PPAR), a member of the steroid nuclear receptor superfamily. We have cloned the cDNA from rat that is homologous to that from mouse, which encodes a 97% similar protein. To search for physiologically occurring activators, we established a transcriptional transaction assay by stably

Carlos Bocos; Martin Göttlicher; Katy Gearing; Carol Banner; Eva Enmark; Michčle Teboul; Anja Crickmore; Jan-Ĺke Gustaffson

1995-01-01

13

Defining the Molecular Actions of Dietary Fatty Acids in Breast Cancer: Selective Modulation of Peroxisome Proliferator-Activated Receptor Gamma.  

National Technical Information Service (NTIS)

Stark differences in the actions of lenoleic acid (LAA), an omega-6 fatty acid, and eicosapentaenoic acid (EPA), an omega-3 fatty acid, on breast cancer tumors have been described. We propose that transactivation of peroxisome proliferators-activated rece...

C. D. Allred

2005-01-01

14

The fungicidal activity of the unsaturated fatty acids and quaternary salts prepared from fish oils  

Microsoft Academic Search

Summary  Saturated and unsaturated fatty acids and 10 unsaturated fatty acid fractions and ethyl esters of unsaturated fatty acid fractions\\u000a prepared from fish oils were tested on their inhibitory activity againstCandida albicans.\\u000a \\u000a Oxidation of highly unsaturated fractions from fish oil and ethyl esters of unsaturated fatty acid fractions of menhaden,\\u000a pilchard, and cod liver oils increases their antifungal activity.\\u000a \\u000a \\u000a \\u000a Saturated and

Boris Sokoloff; Masamichi Toyomizu; Walter Trauner; George Renninger

1959-01-01

15

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

PubMed Central

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

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

2010-01-01

16

Fatty acids and neurodevelopment.  

PubMed

Knowledge of the importance of docosahexaenoic acid (DHA), arachidonic acid (AA), and long-chain polyunsaturated fatty acids (LCPUFAs) in neurodevelopment was originally obtained from animal studies. These fatty acids are rapidly accreted in brain during the first postnatal year in animal and human infants, and they are found in high concentrations in breast milk. Reports of enhanced intellectual development in breast-fed children, and reports linking LCPUFA deficiency with neurodevelopmental disorders have stressed the physiological importance of DHA in visual and neural systems. In addition to high concentrations of fatty acids in breast milk, they are also present in fish and algae oil and have recently been added to infant formulas. Esterified poplyunsaturated fatty acids act in cellular membranes, in signal transduction, in neurotransmission, and in the formation of lipid rafts. Nonesterified polyunsaturated fatty acids can modulate gene expression and ion channel activities, thus becoming neuroprotective agents. The conversion of linoleic acid and alpha-linolenic acid into ARA and DHA have led to randomized clinical trials that have studied whether infant formulas supplemented with DHA or both DHA and ARA would enhance visual and cognitive development. This review gives an overview of fatty acids and neurodevelopment, focusing on the findings from these studies. PMID:18667917

Belkind-Gerson, J; Carreón-Rodríguez, A; Contreras-Ochoa, C O; Estrada-Mondaca, S; Parra-Cabrera, M S

2008-08-01

17

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

PubMed Central

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 the fatty acid distribution in the inflamed ileal mucosa was significantly characterised by (a) a decrease of 18:2 n6 and 18:3 n3 accompanied by a substantial increase of the highly polyunsaturated fatty acids 20:4 n6, 22:4 n6, and 22:6 n3 and (b) a higher unsaturation index of total fatty acids compared with controls. These changes were similar in the inflamed colon. Additionally, both the inflamed and the macroscopically normal colonic mucosa showed an increase of saturated (18:0) and a decrease of monounsaturated fatty acids (18:1 n9). Fatty acid profiles of ileum and colon showed side variations in controls, but not in the Crohn's disease group. These data suggest that in Crohn's disease changes in the distribution of polyunsaturated fatty acids seem to be the general feature of inflamed mucosa in small and large intestine. Results further suggest that colonic fatty acid metabolism in Crohn's disease is altered by degrees, showing changes in saturated and monounsaturated fatty acids as an additional, primary event.

Buhner, S; Nagel, E; Korber, J; Vogelsang, H; Linn, T; Pichlmayr, R

1994-01-01

18

Fatty acids regulate perilipin5 in muscle by activating PPAR?.  

PubMed

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

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

2013-04-20

19

Serum Paraoxonase 1 Activity Is Associated with Fatty Acid Composition of High Density Lipoprotein  

PubMed Central

Introduction. Cardioprotective effect of high density lipoprotein (HDL) is, in part, dependent on its related enzyme, paraoxonase 1 (PON1). Fatty acid composition of HDL could affect its size and structure. On the other hand, PON1 activity is directly related to the structure of HDL. This study was designed to investigate the association between serum PON1 activity and fatty acid composition of HDL in healthy men. Methods. One hundred and forty healthy men participated in this research. HDL was separated by sequential ultracentrifugation, and its fatty acid composition was analyzed by gas chromatography. PON1 activity was measured spectrophotometrically using paraxon as substrate. Results. Serum PON1 activity was directly correlated with the amount of stearic acid and dihomo-gamma-linolenic acid (DGLA). PON1/HDL-C was directly correlated with the amount of miristic acid, stearic acid, and DGLA and was inversely correlated with total amount of ?6 fatty acids of HDL. Conclusion. The fatty acid composition of HDL could affect the activity of its associated enzyme, PON1. As dietary fats are the major determinants of serum lipids and lipoprotein composition, consuming some special dietary fatty acids may improve the activity of PON1 and thereby have beneficial effects on health.

Boshtam, Maryam; Pourfarzam, Morteza; Ani, Mohsen; Naderi, Gholam Ali; Basati, Gholam; Mansourian, Marjan; Dinani, Narges Jafari; Asgary, Seddigheh; Abdi, Soheila

2013-01-01

20

AMPK activation increases fatty acid oxidation in skeletal muscle by activating PPAR? and PGC1  

Microsoft Academic Search

AMP-activated protein kinase (AMPK) activation increases fatty acid oxidation in skeletal muscle by decreasing malonyl CoA concentrations. However, this may not explain the long-term effects of AMPK activation. Here we show that AMPK activation by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR) increases mRNA expression of PPAR? target genes and PGC-1 in cultured muscle cells and mouse skeletal muscle, and that inhibition of PPAR?

Woo Je Lee; Mina Kim; Hye-Sun Park; Hyoun Sik Kim; Min Jae Jeon; Ki Sook Oh; Eun Hee Koh; Jong Chul Won; Min-Seon Kim; Goo Taeg Oh; Michung Yoon; Ki-Up Lee; Joong-Yeol Park

2006-01-01

21

Evaluation of antioxidant activity and the fatty acid profile of the leaves of Vernonia amygdalina growing in South Africa  

Microsoft Academic Search

The leaves of Vernonia amygdalina were examined for antioxidant activity and analysed for their fatty acids content. Using transesterification and GC–MS analysis, 12 fatty acids were identified, which accounted for 74.1% of the lipid content. Two essential fatty acids (EFA), linoleic and ?-linolenic acid were found in abundance in the oil. Using DPPH and a ABTS radical scavenging experiments, acetone,

Paul Erasto; Donald S. Grierson; Anthony J. Afolayan

2007-01-01

22

Fatty Acids as Modulators of Membrane Functions: Catecholamine-Activated Adenylate Cyclase of the Turkey Erythrocyte  

Microsoft Academic Search

Activation of the adenylate cyclase [ATP pyrophosphate-lyase (cyclizing), EC 4.6.1.1] from turkey erythrocytes by isoproterenol decreased precipitously below 26 degrees. Certain unsaturated fatty acids enhanced the activation by isoproterenol up to 25-fold at reduced temperatures. The fatty acid also enhanced the formation of a persistent active state of the enzyme which was produced by preincubation with guanosine 5'-(beta ,gamma -imino)triphosphate

Joseph Orly; Michael Schramm

1975-01-01

23

Plant fatty acid hydroxylases  

DOEpatents

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

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

2001-01-01

24

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.

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

2011-01-01

25

FATP1 mediates fatty acid-induced activation of AMPK in 3T3-L1 adipocytes  

Microsoft Academic Search

Fatty acid transport proteins are integral membrane acyl-CoA synthetases implicated in adipocyte fatty acid influx and esterification. FATP-dependent production of AMP was evaluated using FATP4 proteoliposomes, and fatty acid-dependent activation of AMP-activated protein kinase (AMPK) was assessed in 3T3-L1 adipocytes. Insulin-stimulated fatty acid influx (palmitate or arachidonate) into cultured adipocytes resulted in an increase in the phosphorylation of AMPK and

Brian M. Wiczer; Sandra Lobo; G. Luke Machen; Lee M. Graves; David A. Bernlohr

2009-01-01

26

Morphological alterations and ganglioside sialyltransferase activity induced by small fatty acids in HeLa cells  

Microsoft Academic Search

Incubation of HeLa cells in the presence of millimolar concentrations of propionate, butyrate, or pentanoate increases the specific activity of CMPosialic acid:lactosylceramide sialyltransferase 7-20-fold within 24 h. Longer-chain saturated fatty acids or acetate are much less effective, decanoate showing no induction. Unsaturated fatty acid analogs of butyrate and other compounds are ineffective. Only the three most effective compounds also produce

JEFFREY L. SIMMONS; PETER H. FISHMAN; ERNEST FREESE; ROSCOE O. BRADY

1975-01-01

27

Fatty acid-binding protein activities in bovine muscle, liver and adipose tissue  

SciTech Connect

Subcutaneous adipose tissue, sternomandibularis muscle and liver were obtained from steers immediately postmortem. Muscle strips and adipose tissue snips were incubated with 0.75 mM (1- UC)palmitate and 5 mM glucose. Muscle strips esterified palmitate at the rate of 2.5 nmol/min per gram tissue, which was 30% of the rate observed for adipose tissue. Fatty acid-binding protein activity was measured in 104,000 x g supernatant fractions of liver, muscle and adipose tissue homogenates. Muscle and adipose tissue fractions bound 840 and 140 pmol (1- UC)palmitoyl-CoA per gram tissue, respectively. Fatty acid-binding protein activity was greater in adipose tissue than in muscle when data were expressed per milligram protein. Fatty acid binding-protein activity was correlated with the rate of palmitate esterification within each tissue. Liver contained the highest fatty acid-binding protein activity.

Smith, S.B.; Ekeren, P.A.; Sanders, J.O.

1985-11-01

28

Dietary polyunsaturated fatty acids enhance hepatic AMP-activated protein kinase activity in rats  

Microsoft Academic Search

Polyunsaturated fatty acids (PUFA) and a number of drugs (metformin, thiazolidinediones) and hormones (leptin, adiponectin) that activate AMP-activated protein kinase (AMPK) have been reported to improve insulin sensitivity. To determine whether PUFA activate AMPK, Sprague–Dawley rats were adapted to a 3h meal-feeding regimen using a fat-free diet (FFD) supplemented with fish oil (n?3) or triolein (n?9) for 7 days. No

Gabriela Suchankova; Michael Tekle; Asish K. Saha; Neil B. Ruderman; Steven D. Clarke; Thomas W. Gettys

2005-01-01

29

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.

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

2012-01-01

30

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.

Elner, Victor M

2002-01-01

31

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

32

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

33

MODULATION OF ENDOTHELIAL CELL ACTIVATION BY OMEGA6 AND OMEGA3 FATTY ACIDS  

Microsoft Academic Search

Endothelial activation is considered to be an early and critical event in the pathology of atherogenesis which can be modified by environmental factors such as diet, pollutants, and lifestyle habits. Dietary andamp;ugrave;-6 and andamp;ugrave;-3 fatty acids have been reported to either amplify or diminish inflammatory responses related to atherosclerosis development. However, the interactions of andamp;ugrave;-6 and andamp;ugrave;-3 fatty acids with

Lei Wang

2007-01-01

34

Fatty acids and hypolipidemic drugs regulate peroxisome proliferator-activated receptors - and -mediated gene expression via liver fatty acid binding protein: A signaling path to the nucleus  

Microsoft Academic Search

Peroxisome proliferator-activated receptor (PPAR) is a key regulator of lipid homeostasis in hepatocytes and target for fatty acids and hypolipidemic drugs. How these signaling molecules reach the nuclear receptor is not known; however, similarities in ligand specificity suggest the liver fatty acid binding protein (L-FABP) as a possible candidate. In localization studies using laser-scanning microscopy, we show that L-FABP and

Christian Wolfrum; Carola M. Borrmann; Torsten Börchers; Friedrich Spener

2001-01-01

35

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...

36

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 ...

37

Purification and Identification of Bovine Cheese Whey Fatty Acids Exhibiting In Vitro Antifungal Activity  

Microsoft Academic Search

Milk lipids contain several bioactive factors exhib- iting antimicrobial activity against bacteria, viruses, and fungi. In the present study, we demonstrate that free fatty acids (FFA) derived from the saponification of bovine whey cream lipids are active in vitro at inhib- iting the germination of Candida albicans, a morpho- logical transition associated with pathogenicity. This activity was found to be

M. Clément; J. Tremblay; M. Lange; J. Thibodeau; P. Belhumeur

2008-01-01

38

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.

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

2012-01-01

39

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

40

Identification and egg hatching activity of monohydroxy fatty acid eicosanoids in the barnacle Balanus balanoides.  

PubMed

Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography-mass spectrometry (GC-MS) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17-eicosapentaenoic acid (8-HEPE) was the only MHFA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8(R) conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10(-7) M whereas the enantiomer 8(S)-HEPE was inactive. PMID:1348120

Hill, E M; Holland, D L

1992-01-22

41

High saturated fatty acids proportion in Escherichia coli enhances the activity of ice-nucleation protein from Pantoea ananatis.  

PubMed

The ice-nucleation protein (INP) from Pantoea ananatis was expressed in Escherichia coli. INP expression increased the freezing point of the E. coli culture by a few degrees. Deletion of FabH, an important enzyme in fatty acid biosynthesis, significantly inhibited the ice-nucleation activity. Increased unsaturated fatty acids in the fabH mutant cells decreased the ice-nucleation activity. Adding exogenous saturated fatty acids increased both E. coli fatty acid saturation and the ice-nucleation activity. In contrast, adding unsaturated fatty acids exhibited the opposite effects. Furthermore, an E. coli MG1655-fadR strain with high saturated fatty acids content was constructed, in which the INP activity was enhanced by about 17% compared with its activity in the wild-type MG1655 strain. PMID:23763336

Yu, Feifei; Liu, Xiping; Tao, Yong; Zhu, Kun

2013-07-01

42

Antimicrobial agents derived from fatty acids  

Microsoft Academic Search

The author reviews his research, since 1966, for the ideal germicide. The relationship between structure of fatty acids, their\\u000a corresponding esters, and antimicrobial activity is presented. Saturated fatty acids have their highest activity when the\\u000a chain length is twelve carbons (C12) long; monounsaturated fatty acids reach their peak with palmitoleic acid (C16?1); the most active polyunsaturated fatty acid is linoleic.Trans

John J. Kabara

1984-01-01

43

Molecular Recognition of Fatty Acids by Peroxisome Proliferator–Activated Receptors  

Microsoft Academic Search

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

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

1999-01-01

44

? 9 desaturase activity in bovine subcutaneous adipose tissue of different fatty acid compositiondesaturase activity in bovine subcutaneous adipose tissue of different fatty acid composition  

Microsoft Academic Search

Two experiments were conducted to investigate the relationship between ?9 desaturase (stearoyl-coenzyme A desaturase) activity and fatty acid composition in subcutaneous adipose tissue from cattle\\u000a of different backgrounds. In Experiment 1, subcutaneous adipose tissue samples were taken from carcasses of pasture-fed cattle\\u000a and feedlot cattle fed for 100, 200, or 300 d. Adipose tissue from pasture-fed cattle had significantly lower

A. Yang; T. W. Larsen; S. B. Smith; R. K. Tume

1999-01-01

45

Peroxisome proliferator-activated receptor alpha agonist, clofibrate, has profound influence on myocardial fatty acid composition.  

PubMed

The hypolipidemic fibrates have been identified as agonists of the peroxisome proliferator-activated receptor alpha (PPARalpha), which plays a critical role in the regulation of cardiac fatty acid metabolism. Despite the widespread clinical use of fibrates, their role in myocardial oxidative stress and fatty acid composition is less known. In this study, male Sprague-Dawley rats were treated with either vehicle (olive oil, 1 ml/kg) or clofibrate (300 mg/kgday i.p.) for 1-14 days. Lipid peroxidation in heart homogenate was determined by thiobarbituric acid reactive substance (TBARS) assay. Results show that hearts from clofibrate-treated rats are more susceptible to FeSO(4)-induced TBARS production. The antioxidants including catalase and glutathione-related enzymes were marginally affected. We demonstrated that myocardial fatty acid composition was dramatically altered by clofibrate treatment. In hearts from clofibrate-treated rats, the principal n-6 polyunsaturated fatty acids (PUFAs), linoleic acid (C18:2 n-6) and arachidonic acid (C20:4 n-6), was significantly reduced, while the content of the principal n-3 PUFA, docosahexaenoic acid (C22:6 n-3), was markedly increased. The overall effect was to reduce n-6/n-3 ratio and increase the unsaturation extent of myocardial fatty acids. Functional study showed that hearts from clofibrate-treated rats had an improved recovery of post-ischemic contractile function and reduced ischemia/reperfusion (I/R)-induced infarct size. The data shows that clofibrate has a profound impact on cardiac fatty acid composition, which may contribute to its cardioprotective effect. PMID:16540100

Tian, Qi; Grzemski, Felicity A; Panagiotopoulos, Sianna; Ahokas, Jorma T

2006-03-15

46

Defining the Molecular Actions of Dietary Fatty Acids in Breast Cancer: Selective Modulation of Peroxisome Proliferator-Activated Receptor Gamma. Addendum.  

National Technical Information Service (NTIS)

Stark differences in the actions of linoleic acid (LAA), an omega-6 fatty acid, and eicosapentaenoic acid (EPA), an omega-3 fatty acid, on breast cancer tumors have been described. We propose that transactivation of peroxisome proliferators-activated rece...

C. D. Allred M. W. Kilgore

2008-01-01

47

Liver fatty acid composition and peroxisomal fatty acid oxidase activity in blue foxes (Alopex lagopus) and mink (Mustela vison) fed diets containing different levels of fish oil.  

PubMed

At the time of pelting (Nov.), blue foxes had a lower liver lipid content (4-5%) than mink (7-10%), whereas the phospholipid (PL) content was 0.5-1% in both species. Dietary fat content had little influence on total liver fat content but affected the liver fatty acid composition. Levels of n3 fatty acids were higher in the PL fraction than in the remaining fraction of liver lipids in both species. Because PL accounted for a larger part of the total liver lipids in blue foxes than in mink, the proportion of the total liver lipids accounted for by n3 fatty acids was highest in blue foxes. On the other hand, the mink and foxes had about the same quantity of n3 per gram liver owing to higher fat content of mink liver. Analyses of liver lipid fatty acid composition did not reveal any differences between the species in their ability to metabolize n3 fatty acids originating from fish oil. Peroxisomal beta-oxidation activity in the liver was significantly higher in blue foxes than in mink. For both species the total activity rose as the level of dietary fish oil increased. PMID:9185341

Ahlstrřm, O; Skrede, A

1997-05-01

48

Biocatalytic acylation of carbohydrates with fatty acids from palm fatty acid distillates  

Microsoft Academic Search

Palm fatty acid distillates (PFAD) are by-products of the palm oil refining process. Their use as the source of fatty acids, mainly palmitate, for the biocatalytic synthesis of carbohydrate fatty acid esters was investigated. Esters could be prepared in high yields from unmodified acyl donors and non-activated free fatty acids obtained from PFAD with an immobilized Candida antarctica lipase preparation.

Thanongsak Chaiyaso; Aran H-kittikun; Wolfgang Zimmermann

2006-01-01

49

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

PubMed Central

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

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

2010-01-01

50

Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids.  

PubMed

This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. PMID:24103427

Rodrigues, Marieli O; Cantos, Jéssica B; D'Oca, Caroline R Montes; Soares, Karina L; Coelho, Tatiane S; Piovesan, Luciana A; Russowsky, Dennis; da Silva, Pedro A; D'Oca, Marcelo G Montes

2013-09-20

51

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

PubMed

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

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

2011-03-01

52

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...

53

Cytochrome b? coexpression increases Tetrahymena thermophila ?6 fatty acid desaturase activity in Saccharomyces cerevisiae.  

PubMed

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 b? protein sequences identified from the genome of T. thermophila included one sequence with two conserved cytochrome b? domains. Desaturation by the ?6 enzyme increased as much as 10-fold when T. thermophila cytochrome b?s were coexpressed with the desaturase. Coexpression of a cytochrome b? from Arabidopsis thaliana with the ?6 enzyme also increased desaturation. A split ubiquitin growth assay indicated that the strength of interaction between cytochrome b? 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; Browse, John

2013-04-12

54

Essential-oil and fatty-acid composition, and antioxidant activity of extracts of Ficaria kochii.  

PubMed

The essential-oil and fatty-acid composition of the aerial parts of Ficaria kochii (Ledeb.) Iranshahr & Rech.f. native to Iran, and the antioxidant activity of various extracts of this plant were examined. The study by GC-FID and GC/MS analysis of the essential oil resulted in the identification of 61 compounds, representing 86.01% of the total oil composition. Phytol (10.49%), farnesol (7.72%), methyl linoleate (5.57%), and ?-farnesene (4.96%) were the main components. The fatty-acid composition of the aerial parts of F. kochii was also analyzed by GC/MS. The major components were palmitic acid (25.9%), linolenic acid (25.3%), and linoleic acid (17.5%). Polyunsaturated fatty acids (PUFAs) were found in higher amounts than saturated fatty acids. The possible antioxidant activity of various extracts (prepared by using solvents with different polarity) of the F. kochii aerial parts was evaluated by screening for their 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity, Fe(III) -reducing power, total antioxidant activity, and inhibitory activity in the linoleic acid-peroxidation system. H(2) O proved to be the most efficient solvent for the extraction of antioxidants, as the H(2) O extract contained the highest amount of phenolic compounds (2.78±0.23 GAE/g dry matter) and also exhibited the strongest antioxidant capacity in all the assays used. The results of the present investigation demonstrated that the aerial parts of F. kochii can be used as natural and safe nutrition supplement in place of synthetic ones. PMID:23255443

Tavakoli, Rahmatollah; Mohadjerani, Maryam; Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Naqinezhad, Alireza

2012-12-01

55

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

PubMed

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

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

2013-04-18

56

Antioxidant, antimicrobial activities and fatty acid components of flower, leaf, stem and seed of Hypericum scabrum.  

PubMed

The hexane extracts of flower, leaf, stem, and seed of Hypericum scabrum, which were collected from northwestern Iran, were obtained by extraction in a Soxhlet apparatus. The fatty acids were converted to methyl esters and determined by gas chromatography/flame ionization detector (GC/FID) and gas chromatography/mass spectrometry (GC/MS) systems. The hexane extract from the flower, leaf, stem, and seed contained 39.1%, 43.2%, 29.0%, and 37.6% of omega-3 fatty acids, respectively. The other main components of the flower extract were tetracosane (12.2%) and palmitic acid (9.3%), and that of the leaf extract was palmitic acid (7.4%). The stem and seed extracts contained bis(2-ethylhexyl)phthalate (18.7% and 35.7%), nonacosane (11.7% and 3.9%) and linoleic acid (6.5% and 6.9%) as major components. The hexane extracts of different parts from H. scabrum represent an important source of omega-3 fatty acids in several Hypericum species. The antioxidant activity of all hexane extracts was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The results indicate that hexane extracts from different parts of H. scabrum possess considerable antioxidant activity. The highest radical scavenging activity was detected in seed, which had an IC50 = 165 microg/mL. The antimicrobial activity of the extracts of those samples were determined against seven Gram-positive and Gram-negative bacteria (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae), as well as three fungi (Candida albicans, Saccharomyces cerevisiae, and Aspergillus niger). The bioassay showed that the oil exhibited moderate antimicrobial activity. This study reveals that the all parts of this plant are attractive sources of fatty acid components, especially the essential ones, as well as of effective natural antioxidants. PMID:22224301

Shafaghat, Ali

2011-11-01

57

Influence of fatty acids on ammonia and amino acid flux from active human muscle.  

PubMed

This study examined the dynamics of ammonia and amino acid exchange of human muscle during prolonged steady-state one-legged exercise at 80% of knee extensor maximal work capacity. Subjects (n = 10) performed leg extensor exercise for 1 h (control series), rested for 40 min while an infusion of Intralipid and heparin was begun, and then exercised the contralateral leg with the identical protocol [free fatty acid (FFA) series]. In the control series, ammonia efflux rose progressively, and 4.4 +/- 0.6 mmol were released in 1 h compared with 2.4 +/- 0.5 mmol (P less than 0.05) in the FFA series. The exercise was associated with large effluxes of total amino acids from the active muscle over the hour (12.8 +/- 4.3 and 10.3 +/- 3.3 mmol for control and FFA, respectively). Glutamine and alanine accounted for 47 and 64% of the efflux for the control and FFA series, respectively, while comparable values for essential amino acids were 24 and 20%. The latter implies that a net muscle protein catabolism was occurring during the exercise. The FFA treatment was associated not only with a reduced muscle ammonia release but also with a decreased (P less than 0.05) arterial concentration of nine amino acids (alanine, methionine, lysine, hydroxyproline, serine, glycine, proline, asparagine, and ornithine). Interpretation is limited due to the treatment order effect, but these data are compatible with the hypothesis that plasma clearance was affected by FFA. PMID:1872380

Graham, T E; Kiens, B; Hargreaves, M; Richter, E A

1991-08-01

58

Polyunsaturated fatty acids, inflammation and immunity  

Microsoft Academic Search

Consumption of n-6 polyunsaturated fatty acids greatly exceeds that of n-3 polyunsaturated fatty acids. The n-6 polyunsaturated fatty acid arachidonic gives rise to the eicosanoid family of inflammatory mediators (prostaglandins, leukotrienes and related metabolites) and through these regulates the activities of inflammatory cells, the production of cytokines and the various balances within the immune system. Fish oil and oily fish

PC Calder; RF Grimble

2002-01-01

59

Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms  

PubMed Central

Objective This study is to assess the antibacterial activity of omega-6, -7, -9 (n-6, n-7, n-9) fatty acids against various oral microorganisms. Methods The n-6, n-7, n-9 fatty acids, such as ?-linoleic acid (GLA), linoleic acid (LA), arachidonic acid (ARA), palmitoleic acid (PA), and oleic acid (OA), their fatty acid ethyl esters, GLA-EE, LA-EE, ARA-EE, PA-EE, OA-EE, and their fatty acid methyl esters, GLA-ME, LA-ME, ARA-ME, PA-ME, OA-ME were investigated for antimicrobial activity against oral pathogens Streptococcus mutans, Candida albicans, Aggregatibacter actinomycetemcomitans, Fusobacterium nucleatum, and Porphyromonas gingivalis. Various concentrations of the fatty acids, their methyl and ethyl esters were tested against various oral pathogens in 96-well plates and blood-agar plate. The plates were incubated anaerobically or aerobically at 37°C for 48 hours, and the colony forming units (CFU) were determined. Results The data demonstrated that select n-6, n-7, n-9 fatty acids and their esters exhibited strong antimicrobial activity against these oral microorganisms, demonstrating some specificity for individual microbial species. Conclusion The potential use or the combinations of the n-6, n-7, n-9 fatty acids and/or their esters, provided in a local delivery vehicle to infected sites in the oral cavity, could be considered as an additional therapeutic approach to improving oral health.

Huang, Chifu B.; George, Brian; Ebersole, Jeffery L.

2010-01-01

60

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

Microsoft Academic Search

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)

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

2011-01-01

61

Recent developments in the antiprotozoal and anticancer activities of the 2-alkynoic fatty acids.  

PubMed

The 2-alkynoic fatty acids are an interesting group of synthetic compounds that display antimycobacterial, antifungal, anticancer, and pesticidal activities but their antiprotozoal activity has received little attention until recently. In this review we have summarized our present knowledge of the biomedical potential of the 2-hexadecynoic acid (2-HDA) and 2-octadecynoic acid (2-ODA) together with several mechanistic pieces of work attesting to the fact that these compounds, and their metabolites, are good fatty acid biosynthesis inhibitors. The antiprotozoal activity of 2-HDA and 2-ODA against Leishmania donovani and Plasmodium falciparum, parasites responsible for visceral leishmaniasis and malaria, respectively, is also reviewed. The evidence obtained so far supports the fact that these fatty acids are good inhibitors of the L. donovani DNA topoisomerase IB enzyme (LdTopIB) and the potency of LdTopIB inhibition is chain length dependent. We also demonstrate the generality of the antiprotozoal activity of 2-HDA and 2-ODA against P. falciparum, and review our present knowledge of their inhibition of key P. falciparum enzymes such as PfFabZ, PfFabG, and PfFabI together with some possible modes of inhibition. Recent research by our group has also demonstrated that 2-ODA displays antineoplastic activity, specifically against the neuroblastoma SH-SY5Y cell line via lactate dehydrogenase (LDH) release, which is a cell death mechanism principally associated to necrosis. This is the first comprehensive review of the medicinal chemistry of this interesting group of acetylenic fatty acids. PMID:23727443

Carballeira, Néstor M

2013-05-28

62

Mouse GPR40 heterologously expressed in Xenopus oocytes is activated by short-, medium-, and long-chain fatty acids.  

PubMed

Several orphan G protein-coupled receptors, including GPR40, have recently been shown to be responsive to fatty acids. Although previous reports have suggested GPR40 detects medium- and long-chain fatty acids, it has been reported to be unresponsive to short chain fatty acids. In this study, we have heterologously expressed mouse GPR40 in Xenopus laevis oocytes and measured fatty acid-induced increases in intracellular Ca(2+), via two electrode voltage clamp recordings of the endogenous Ca(2+)-activated chloride conductance. Exposure to 500 muM linoleic acid (C18:2), a long-chain fatty acid, stimulated significant currents in mGPR40-injected oocytes (P < 0.01, ANOVA), but not in water-injected control oocytes (not significant, ANOVA). These currents were confirmed as Ca(2+)-activated chloride conductances because they were biphasic, sensitive to changes in external pH, and inhibited by DIDS. Similar currents were observed with medium-chain fatty acids, such as lauric acid (C12:0) (P < 0.01, ANOVA), and more importantly, with short-chain fatty acids, such as butyric acid (C4:0) (P < 0.01, ANOVA). In contrast, no responses were observed in mGPR40-injected oocytes exposed to either acetic acid (C2:0) or propionic acid (C3:0). Therefore, GPR40 has the capacity to respond to fatty acids with chain lengths of four or greater. This finding has important implications for understanding the structure:function relationship of fatty acid sensors, and potentially for short-chain fatty acid sensing in the gastrointestinal tract. PMID:16267104

Stewart, Gavin; Hira, Tohru; Higgins, Andrew; Smith, Craig P; McLaughlin, John T

2005-11-02

63

Anaerobic decomposition of benzoic acid during methane fermentation: Specific activity of fatty acid intermediates and postion of radioactive label  

SciTech Connect

A study of the pathway of anaerobic decomposition of benzoic acid by a mixed methanogenic culture of bacteria was conducted. Specific activities of the possible fatty acid intermediates cyclohexanecarboxylic acid, propanoic acid, and acetic acid were determined. In the case of propanoic acid, the position of the radioactive label was also determined by isotropic trapping and Phares-Schmidt degradation of the intermediate. The specific activities of cyclohexanecarboxylic acid and propanoic acid are the same as the benzoate substrate fed to the mixed methanogenic cultures. These fatty acids must be direct breakdown products from the aromatic ring. When (4{minus}{sup 14}C) benzoate is the substrate, the propanoic acid produced is labeled exclusively in the carboxyl position. This supports the pathway proposed by Keith et al. (1978), but would be unlikely for the pathway proposed by Evans (1977). The specific activity of the acetic acid isolated from a culture fed (4{minus}{sup 14}C) benzoate is 42% of the specific activity of the substrate. This is possible only if the methylmalonyl-CoA pathway for the conversion of propanoate to acetate is not being utilized. The amount of various intermediates found indicates that at least three syntrophically linked organisms are present in the mixed methanogenic culture. One is responsible for the production of cyclohexanecarboxylic acid, one for the production of acetate from propanoate, and one for the production of methane.

Bridges, R.L.

1990-01-01

64

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

65

Animal Fatty Acid Synthase: Functional Mapping and Cloning and Expression of the Domain I Constituent Activities  

Microsoft Academic Search

Animal fatty acid synthase (FAS; EC 2.3.1.85) is a homodimer of a multifunctional subunit protein and catalyzes the synthesis of palmitate from acetyl-CoA, malonyl-CoA, and NADPH. The subunit (Mr≈ 270,000) carries seven distinct component activities and a site for the prosthetic group 4'-phosphopantetheine (acyl carrier protein). Based on proteolytic mapping, the organization of the activity domains along the subunit polypeptide

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

1997-01-01

66

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

PubMed Central

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

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

2013-01-01

67

n-3 polyunsaturated fatty acids inhibit lipopolysaccharide-induced microglial activation and dopaminergic injury in rats.  

PubMed

Increasing evidence indicates that neuroinflammation plays an important role in neurotoxins-induced neurodegenerations. Microglia are a type of glial cells in the brain and play as the first and main form of active immune defense in the central nervous system. Accumulated data suggest that the activation of microglia plays a critical role in neurotoxicities induced by environmental toxicants. So the inhibition of microglia has been proven to be an effective strategy against neurotoxic effects. In the present study, we found that n-3 polyunsaturated fatty acids can inhibit both microglial activation and dopaminergic injury in the substantia nigra of Sprague-Dawley rats induced by lipopolysaccharide, one of the major constituents of the outer membrane of Gram-negative bacteria. Moreover, n-3 polyunsaturated fatty acids inhibited lipopolysaccharide-induced activation of nuclear factor-?B, an important transcription factor involved in microglial activation. Taken together, our results provided the first in vivo evidence that n-3 polyunsaturated fatty acids can inhibit the damage of dopaminergic neurons induced by lipopolysaccharide through their inhibitory effects on nuclear factor-?B-dependent microglial activation. PMID:22406923

Ji, Ailing; Diao, Huan; Wang, Xiaohui; Yang, Ruihua; Zhang, Jianbin; Luo, Wenjing; Cao, Rui; Cao, Zipeng; Wang, Feng; Cai, Tongjian

2012-03-08

68

Saturated fatty acids activate TLR-mediated proinflammatory signaling pathways[S  

PubMed Central

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 suggested that SFA-induced TLR activation in cell culture systems is due to contaminants in BSA used for solubilizing fatty acids. This report raised doubt about proinflammatory effects of SFAs. Our studies herein demonstrate that sodium palmitate (C16:0) or laurate (C12:0) without BSA solubilization induced phosphorylation of inhibitor of nuclear factor-?B ?, c-Jun N-terminal kinase (JNK), p44/42 mitogen-activated-kinase (ERK), and nuclear factor-?B subunit p65, and TLR target gene expression in THP1 monocytes or RAW264.7 macrophages, respectively, when cultured in low FBS (0.25%) medium. C12:0 induced NF?B activation through TLR2 dimerized with TLR1 or TLR6, and through TLR4. Because BSA was not used in these experiments, contaminants in BSA have no relevance. Unlike in suspension cells (THP-1), BSA-solubilized C16:0 instead of sodium C16:0 is required to induce TLR target gene expression in adherent cells (RAW264.7). C16:0-BSA transactivated TLR2 dimerized with TLR1 or TLR6 and through TLR4 as seen with C12:0. These results and additional studies with the LPS sequester polymixin B and in MyD88?/? macrophages indicated that SFA-induced activation of TLR2 or TLR4 is a fatty acid-specific effect, but not due to contaminants in BSA or fatty acid preparations.

Huang, Shurong; Rutkowsky, Jennifer M.; Snodgrass, Ryan G.; Ono-Moore, Kikumi D.; Schneider, Dina A.; Newman, John W.; Adams, Sean H.; Hwang, Daniel H.

2012-01-01

69

Activation of peroxisome proliferator-activated receptor ? induces fatty acid ?-oxidation in skeletal muscle and attenuates metabolic syndrome  

PubMed Central

In this study, we defined the role of peroxisome proliferator-activated receptor ?/? (PPAR?) in metabolic homeostasis by using subtype selective agonists. Analysis of rat L6 myotubes treated with the PPAR? subtype-selective agonist, GW501516, by the Affymetrix oligonucleotide microarrays revealed that PPAR? controls fatty acid oxidation by regulating genes involved in fatty acid transport, ?-oxidation, and mitochondrial respiration. Similar PPAR?-mediated gene activation was observed in the skeletal muscle of GW501516-treated mice. Accordingly, GW501516 treatment induced fatty acid ?-oxidation in L6 myotubes as well as in mouse skeletal muscles. Administration of GW501516 to mice fed a high-fat diet ameliorated diet-induced obesity and insulin resistance, an effect accompanied by enhanced metabolic rate and fatty acid ?-oxidation, proliferation of mitochondria, and a marked reduction of lipid droplets in skeletal muscles. Despite a modest body weight change relative to vehicle-treated mice, GW501516 treatment also markedly improved diabetes as revealed by the decrease in plasma glucose and blood insulin levels in genetically obese ob/ob mice. These data suggest that PPAR? is pivotal to control the program for fatty acid oxidation in the skeletal muscle, thereby ameliorating obesity and insulin resistance through its activation in obese animals.

Tanaka, Toshiya; Yamamoto, Joji; Iwasaki, Satoshi; Asaba, Hiroshi; Hamura, Hiroki; Ikeda, Yukio; Watanabe, Mitsuhiro; Magoori, Kenta; Ioka, Ryoichi X.; Tachibana, Keisuke; Watanabe, Yuichiro; Uchiyama, Yasutoshi; Sumi, Koichi; Iguchi, Haruhisa; Ito, Sadayoshi; Doi, Takefumi; Hamakubo, Takao; Naito, Makoto; Auwerx, Johan; Yanagisawa, Masashi; Kodama, Tatsuhiko; Sakai, Juro

2003-01-01

70

Trans fatty acids (image)  

MedlinePLUS

Trans fatty acids are manufactured fats created during a process called hydrogenation, which is aimed at stabilizing polyunsaturated oils to prevent them from becoming rancid and to keep them solid at room temperature. They may ...

71

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

PubMed Central

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

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

2001-01-01

72

Different Impacts of Short-Chain Fatty Acids on Saturated and Polyunsaturated Fatty Acid Biosynthesis in Aurantiochytrium sp. SD116.  

PubMed

Aurantiochytrium is an important docosahexaenoic acid (DHA) producer containing two kinds of fatty acid synthesis pathways, that is, the fatty acid synthase pathway (FAS) for saturated fatty acid synthesis and the polyketide synthase pathway (PKS) for polyunsaturated fatty acid synthesis. To understand the regulation mechanism between the two pathways, the impacts of six short-chain fatty acids on the fatty acid synthesis of Aurantiochytrium sp. SD116 were studied. All short-chain fatty acids showed little effect on the cell growth, but some of them significantly affected lipid accumulation and fatty acid composition. Pentanoic acid and isovaleric acid greatly inhibited the synthesis of saturated fatty acids, whereas the polyunsaturated fatty acid synthesis was not affected. Analysis of malic enzyme activity, which supplied NADPH for saturated fatty acids biosynthesis, indicated that the two fatty acid synthesis pathways can utilize different substrates and possess independent sources of NADPH. PMID:24053543

Song, Xiaojin; Tan, Yanzhen; Liu, Yajun; Zhang, Jingtao; Liu, Guanglei; Feng, Yingang; Cui, Qiu

2013-10-07

73

Understanding Fatty Acid Metabolism through an Active Learning Approach  

ERIC Educational Resources Information Center

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

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

2010-01-01

74

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.

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

2013-01-01

75

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

2013-01-11

76

Formation of fatty acid conjugates of ciclesonide active metabolite in the rat lung after 4-week inhalation of ciclesonide  

Microsoft Academic Search

Ciclesonide, an inhaled corticosteroid (ICS) with prolonged anti-inflammatory activity, is being developed for the treatment of asthma. Fatty acid conjugation of ICS is thought to be related to prolonged ICS activity. In vitro studies demonstrated that ciclesonide is converted to an active metabolite, desisobutyryl-ciclesonide (des-CIC), which undergoes reversible fatty acid conjugation. We tested the in vivo metabolism of ciclesonide in

R. Nave; W. Meyer; R. Fuhst; K. Zech

2005-01-01

77

Unsaturated fatty acids prevent activation of NLRP3 inflammasome in human monocytes/macrophages.  

PubMed

The NLRP3 inflammasome is involved in many obesity-associated diseases, such as type 2 diabetes, atherosclerosis, and gouty arthritis, through its ability to induce interleukin (IL)-1? release. The molecular link between obesity and inflammasome activation is still unclear, but free fatty acids have been proposed as one triggering event. Here we reported opposite effects of saturated fatty acids (SFAs) compared with unsaturated fatty acids (UFAs) on NLRP3 inflammasome in human monocytes/macrophages. Palmitate and stearate, both SFAs, triggered IL-1? secretion in a caspase-1/ASC/NLRP3-dependent pathway. Unlike SFAs, the UFAs oleate and linoleate did not lead to IL-1? secretion. In addition, they totally prevented the IL-1? release induced by SFAs and, with less efficiency, by a broad range of NLRP3 inducers, including nigericin, alum, and monosodium urate. UFAs did not affect the transcriptional effect of SFAs, suggesting a specific effect on the NLRP3 activation. These results provide a new anti-inflammatory mechanism of UFAs by preventing the activation of the NLRP3 inflammasome and, therefore, IL-1? processing. By this way, UFAs might play a protective role in NLRP3-associated diseases. PMID:24006511

L'homme, Laurent; Esser, Nathalie; Riva, Laura; Scheen, André; Paquot, Nicolas; Piette, Jacques; Legrand-Poels, Sylvie

2013-09-03

78

Saturated fatty acids activate ERK signaling to downregulate hepatic sortilin 1 in obese and diabetic mice.  

PubMed

Hepatic VLDL overproduction is a characteristic feature of diabetes and an important contributor to diabetic dyslipidemia. Hepatic sortilin 1 (Sort1), a cellular trafficking receptor, is a novel regulator of plasma lipid metabolism and reduces plasma cholesterol and triglycerides by inhibiting hepatic apolipoprotein B production. Elevated circulating free fatty acids play key roles in hepatic VLDL overproduction and the development of dyslipidemia. This study investigated the regulation of hepatic Sort1 in obesity and diabetes and the potential implications in diabetic dyslipidemia. Results showed that hepatic Sort1 protein was markedly decreased in mouse models of type I and type II diabetes and in human individuals with obesity and liver steatosis, whereas increasing hepatic Sort1 expression reduced plasma cholesterol and triglycerides in mice. Mechanistic studies showed that the saturated fatty acid palmitate activated extracellular signal-regulated kinase (ERK) and inhibited Sort1 protein by mechanisms involving Sort1 protein ubiquitination and degradation. Consistently, hepatic ERK signaling was activated in diabetic mice, whereas blocking ERK signaling by an ERK inhibitor increased hepatic Sort1 protein in mice. These results suggest that increased saturated fatty acids downregulate liver Sort1 protein, which may contribute to the development of dyslipidemia in obesity and diabetes. PMID:23904453

Bi, Lipeng; Chiang, John Y L; Ding, Wen-Xing; Dunn, Winston; Roberts, Benjamin; Li, Tiangang

2013-07-31

79

Fatty acid levels and phospholipase activity in erythrocytes in the presence of radiation sickness with prior administration of cystamine  

Microsoft Academic Search

The levels of free fatty acids and phospholipase activity in rabbit erythrocytes at various stages in the development of radiation injury were investigated. The effect of pretreatment with intravenous injection of cystamine on these indices was also discussed.

Serebrennikova

1978-01-01

80

Lipolytic Products Activate Peroxisome Proliferator-activated Receptor (PPAR) ? and ? in Brown Adipocytes to Match Fatty Acid Oxidation with Supply*  

PubMed Central

?-adrenergic receptors (?-ARs) promote brown adipose tissue (BAT) thermogenesis by mobilizing fatty acids and inducing the expression of oxidative genes. ?-AR activation increases the expression of oxidative genes by elevating cAMP, but whether lipolytic products can modulate gene expression is not known. This study examined the role that adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL) plays in the induction of gene expression. Activation of brown adipocytes by ?-AR agonism or 8-bromo-cyclic AMP increased the expression of PGC1?, PDK4, PPAR?, uncoupling protein 1 (UCP1), and neuron-derived orphan receptor-1 (NOR-1), and concurrent inhibition of HSL reduced the induction of PGC1?, PDK4, PPAR?, and UCP1 but not NOR-1. Similar results were observed in the BAT of mice following pharmacological or genetic inhibition of HSL and in brown adipocytes with stable knockdown of ATGL. Conversely, treatments that increase endogenous fatty acids elevated the expression of oxidative genes. Pharmacological antagonism and siRNA knockdown indicate that PPAR? and PPAR? modulate the induction of oxidative genes by ?-AR agonism. Using a live cell fluorescent reporter assay of PPAR activation, we demonstrated that ligands for PPAR? and -?, but not PPAR?, were rapidly generated at the lipid droplet surface and could transcriptionally activate PPAR? and -?. Knockdown of ATGL reduced cAMP-mediated induction of genes involved in fatty acid oxidation and oxidative phosphorylation. Consequently, ATGL knockdown reduced maximal oxidation of fatty acids, but not pyruvate, in response to cAMP stimulation. Overall, the results indicate that lipolytic products can activate PPAR? and PPAR? in brown adipocytes, thereby expanding the oxidative capacity to match enhanced fatty acid supply.

Mottillo, Emilio P.; Bloch, Ainsley E.; Leff, Todd; Granneman, James G.

2012-01-01

81

Lipolytic products activate peroxisome proliferator-activated receptor (PPAR) ? and ? in brown adipocytes to match fatty acid oxidation with supply.  

PubMed

?-Adrenergic receptors (?-ARs) promote brown adipose tissue (BAT) thermogenesis by mobilizing fatty acids and inducing the expression of oxidative genes. ?-AR activation increases the expression of oxidative genes by elevating cAMP, but whether lipolytic products can modulate gene expression is not known. This study examined the role that adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL) plays in the induction of gene expression. Activation of brown adipocytes by ?-AR agonism or 8-bromo-cyclic AMP increased the expression of PGC1?, PDK4, PPAR?, uncoupling protein 1 (UCP1), and neuron-derived orphan receptor-1 (NOR-1), and concurrent inhibition of HSL reduced the induction of PGC1?, PDK4, PPAR?, and UCP1 but not NOR-1. Similar results were observed in the BAT of mice following pharmacological or genetic inhibition of HSL and in brown adipocytes with stable knockdown of ATGL. Conversely, treatments that increase endogenous fatty acids elevated the expression of oxidative genes. Pharmacological antagonism and siRNA knockdown indicate that PPAR? and PPAR? modulate the induction of oxidative genes by ?-AR agonism. Using a live cell fluorescent reporter assay of PPAR activation, we demonstrated that ligands for PPAR? and -?, but not PPAR?, were rapidly generated at the lipid droplet surface and could transcriptionally activate PPAR? and -?. Knockdown of ATGL reduced cAMP-mediated induction of genes involved in fatty acid oxidation and oxidative phosphorylation. Consequently, ATGL knockdown reduced maximal oxidation of fatty acids, but not pyruvate, in response to cAMP stimulation. Overall, the results indicate that lipolytic products can activate PPAR? and PPAR? in brown adipocytes, thereby expanding the oxidative capacity to match enhanced fatty acid supply. PMID:22685301

Mottillo, Emilio P; Bloch, Ainsley E; Leff, Todd; Granneman, James G

2012-06-08

82

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

83

Activity of the acyl-CoA synthetase ACSL6 isoforms: role of the fatty acid Gate-domains  

Microsoft Academic Search

BACKGROUND: Activation of fatty acids by acyl-CoA synthetase enzymes is required for de novo lipid synthesis, fatty acid catabolism, and remodeling of biological membranes. Human long-chain acyl-CoA synthetase member 6, ASCL6, is a form present in the plasma membrane of cells. Splicing events affecting the amino-terminus and alternative motifs near the ATP-binding site generate different isoforms of ACSL6. RESULTS: Isoforms

Eric Soupene; Nghi Phuong Dinh; Melvin Siliakus; Frans A Kuypers

2010-01-01

84

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. ...

85

Linking autotrophic activity in environmental samples with specific bacterial taxa by detection of 13C-labelled fatty acids.  

PubMed

A method for the detection of physiologically active autotrophic bacteria in complex microbial communities was developed based on labelling with the stable isotope 13C. Labelling of autotrophic nitrifying, sulphur-oxidizing and iron-oxidizing populations was performed in situ by incubation with NaH[13C]O3. Incorporated label into fatty acid methyl esters (FAMEs) was detected and quantified using gas chromatography-mass spectrometry in single ion monitoring mode. Before the analyses of different environmental samples, the protocol was evaluated in pure culture experiments. In different environmental samples a selective labelling of fatty acids demonstrated which microbial taxa were responsible for the respective chemolithoautotrophic activity. The most strongly labelled fatty acids of a sample from a sulphide treating biofilter from an animal rendering plant were cis-7-hexadecenoic acid (16:1 cis7) and 11-methyl hexadecanoic acid (16:0 11methyl), which are as-yet not known for any sulphide-oxidizing autotroph. The fatty acid labelling pattern of an experimental biotrickling filter sample supplied with dimethyl disulphide clearly indicated the presence and activity of sulphide-oxidizing bacteria of the genus Thiobacillus. For a third environmental sample from an acid mining lake sediment, the assignment of autotrophic activity to bacteria of the genus Leptospirillum but not to Acidithiobacillus could be made by this method, as the fatty acid patterns of these bacteria show clear differences. PMID:14641595

Knief, Claudia; Altendorf, Karlheinz; Lipski, André

2003-11-01

86

Differential Activation of Nuclear Receptors by Perfluorinated Fatty Acid Analogs and Natural Fatty Acids: A Comparison of Human, Mouse, and Rat Peroxisome Proliferator-Activated Receptor , - , and - , Liver X Receptor , and Retinoid X Receptor  

Microsoft Academic Search

Administration of ammonium salts of perfluorooctanoate (PFOA) to rats results in peroxisome proliferation and benign liver tumors, events associated with activation of the nuclear receptor (NR) peroxisome proliferator-activated receptor-a (PPARa). Due to its fatty acid structure, PFOA may activate other NRs, such as PPARb ,P PARg, liver X receptor (LXR), or retinoid X receptor (RXR). In this study, the activation

John P. Vanden Heuvel; Jerry T. Thompson; Steven R. Frame; Peter J. Gillies

2006-01-01

87

Fatty acids from lipids of marine organisms: molecular biodiversity, roles as biomarkers, biologically active compounds, and economical aspects.  

PubMed

Because of their characteristic living environments, marine organisms produce a variety of lipids. Fatty acids constitute the essential part of triglycerides and wax esters, which are the major components of fats and oils. Nevertheless, phospholipids and glycolipids have considerable importance and will be taken into account, especially the latter compounds that excite increasing interest regarding their promising biological activities. Thus, in addition to the major polyunsaturated fatty acids (PUFA) such as eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids, a great number of various fatty acids occur in marine organisms, e.g. saturated, mono- and diunsaturated, branched, halogenated, hydroxylated, methoxylated, non-methylene-interrupted. Various unprecedented chemical structures of fatty acids, and lipid-containing fatty acids, have recently been discovered, especially from the most primitive animals such as sponges and gorgonians. This review of marine lipidology deals with recent advances in the field of fatty acids since the end of the 1990s. Different approaches will be followed, mainly developing biomarkers of trophic chains in marine ecosystems and of chemotaxonomic interest, reporting new structures, especially those with biological activities or biosynthetic interest. An important part of this review will be devoted to the major PUFA, their relevance to health and nutrition, their biosynthesis, their sources (usual and promising) and market. PMID:16566089

Bergé, Jean-Pascal; Barnathan, Gilles

2005-01-01

88

Saturated fatty acids induce c-Src clustering within membrane subdomains leading to JNK activation  

PubMed Central

Saturated fatty acids (FA) exert adverse health effects and are more likely to cause insulin resistance and type 2 diabetes than unsaturated FA, some of which exert protective and beneficial effects. Saturated FA, but not unsaturated FA, activate Jun N terminal kinase (JNK), which has been linked to obesity and insulin resistance in mice and men. However, it is unknown how saturated and unsaturated FA are discriminated. We now demonstrate that saturated FA activate JNK and induce insulin resistance by altering the membrane distribution of c-Src, causing it to partition into intracellular membrane subdomains where it may become activated. Conversely, unsaturated FA with known beneficial effects on glucose metabolism prevent c-Src membrane partitioning and activation, which are dependent on its myristoylation, and block JNK activation. Consumption of a diabetogenic high fat diet causes the partitioning and activation of c-Src within detergent insoluble membrane subdomains of adipocytes.

Holzer, Ryan G.; Park, Eek-Joong; Li, Ning; Tran, Helen; Chen, Monica; Choi, Crystal; Solinas, Giovanni; Karin, Michael

2011-01-01

89

Fatty acid signaling in Arabidopsis  

Microsoft Academic Search

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

Edward E. Farmer; Hans Weber; Sabine Vollenweider

1998-01-01

90

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

91

Targeting of Acyl-CoA synthetase 5 decreases jejunal fatty acid activation with no effect on dietary long-chain fatty acid absorption  

PubMed Central

Background The absorption of dietary long chain fatty acids (LCFA) largely occurs in the jejunum. LCFA are activated via conjugation with Coenzyme A (CoA), a reaction catalyzed by Acyl-CoA synthetases (ACS). Acyl-CoA sythesis is critical for dietary LCFA absorption; yet, the jejunal ACS enzymes that catalyze the reaction are largely unknown. Findings High throughput mRNA sequencing of the mouse jejunum revealed that the expression of acyl-CoA synthetase 5 (Acsl5) and fatty-acid transport protein 4 (Fatp4) largely exceeded all other annotated ACS genes that activate LCFA. Interestingly, Acsl5 knockout (KO) mice displayed a decrease of 60% in jejunal total long chain acyl-CoA synthesis rate. Nevertheless, and despite of this decrease, dietary LCFA absorption and body-weight gain in response to high fat diet remained unaffected. Conclusion Acsl5 is a major activator of dietary LCFA, yet in Acsl5 KO mice residual ACS activity is sufficient for maintaining a normal LCFA absorption. Our findings provide further evidence for a robust small intestine LCFA absorption capacity.

2013-01-01

92

Facultative alkaliphiles lack fatty acid desaturase activity and lose the ability to grow at near-neutral pH when supplemented with an unsaturated fatty acid.  

PubMed Central

Two obligate alkaliphiles were found to have high levels of fatty acid desaturase, whereas two facultative alkaliphiles had no detectable activity. Supplementation of the growth medium of one facultative strain with palmitoleic acid, but not palmitic acid, at pH 7.5 inhibited growth. The obligate strain outgrows the facultative strain in a chemostat at a very high pH, whereas the converse is true at a pH of 7.5, and the two strains grow equally well at pH 9.0. Thus, the obligate strain is compromised at a near-neutral pH but is better adapted than a related facultative alkaliphile to an extremely alkaline pH.

Dunkley, E A; Guffanti, A A; Clejan, S; Krulwich, T A

1991-01-01

93

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

PubMed

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

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

2013-03-26

94

Dietary trans fatty acids increase serum cholesterylester transfer protein activity in man  

Microsoft Academic Search

The average diet may provide some 8–10 g\\/day of unsaturated fatty acids with a trans double bond. Previous studies showed that dietary trans fatty acids may simultaneously raise low-density lipoprotein (LDL) cholesterol and reduce high-density lipoprotein (HDL) cholesterol. Human plasma contains a protein (CETP) which transfers cholesterylesters from HDL to lipoproteins of lower density. We hypothesized that CETP could play

Arie van Tol; Peter L Zock; Teus van Gent; Leo M Scheek; Martijn B Katan

1995-01-01

95

(Radioiodinated free fatty acids)  

SciTech Connect

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

Knapp, Jr., F. F.

1987-12-11

96

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

97

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

PubMed Central

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?-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-?B (NF-?B). A4/J4-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 (NaBH4), which concurrently abrogated A4/J4-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 A4/J4NPs in the oxidized DHA sample. Treatment of cells with oxidized eicosapentaenoic acid (EPA, 20:5?-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 A4/J4-NPs as mediators of omega-3 fatty acid-mediated protection against the endothelial toxicity of coplanar PCBs.

Majkova, Zuzana; Layne, Joseph; Sunkara, Manjula; Morris, Andrew J.; Toborek, Michal; Hennig, Bernhard

2011-01-01

98

Antifeedant activity of fatty acid esters and phytosterols from Echium wildpretii.  

PubMed

Crude extracts and fractions from Echium wildpretii H. Pearson ex Hook. f. subsp. wildpretii (Boraginaceae) have been tested against insect species Spodoptera littoralis, Leptinotarsa decemlineata, and the aphids Myzus persicae, Diuraphis noxia, Metopolophium dirhodum, Rhopalosiphum maidis, and Rhopalosiphum padi. The EtOH extract and the lipid and steroidal fractions of E. wildpretii exhibited significant antifeedant activities against the aphids and L. decemlineata. Two bioactive mixtures composed of fatty acid esters and n-alkanes were obtained from the lipid fraction. The bioguided fractionation of the steroidal fraction resulted in the isolation of glutinol, ?-sitosterol, (3?,7?)-stigmast-5-ene-3,7-diol, and (3?,7?)-7-methoxystigmast-5-en-3-ol. The latter two compounds exhibited potent antifeedant activities against L. decemlineata indicating that the presence of an O-bearing C(7) was responsible for the activities of these molecules. PMID:22422524

Santana, Omar; Reina, Matias; Fraga, Braulio M; Sanz, Jesús; González-Coloma, Azucena

2012-03-01

99

Free fatty acids enhance breast cancer cell migration through plasminogen activator inhibitor-1 and SMAD4  

PubMed Central

Obesity is a risk factor for breast cancer and is associated with increased plasma concentrations of free fatty acids (FFAs). We and others have demonstrated that FFA induces plasminogen activator inhibitor-1 (PAI-1) expression in a variety of cells. Emerging evidence supports elevation of PAI-1 as a prognostic marker for breast cancer. Therefore, we hypothesized that FFAs might increase expression of PAI-1 in breast cancer cells and facilitate breast cancer progression. Secreted PAI-1 was higher in invasive and metastatic MDA-MB-231 cells compared with less invasive and non-metastatic Hs578T cells. Utilizing FFAs with different saturation and chain lengths, we demonstrated that linoleic acid induced expression of PAI-1 in MDA-MB-231 cells. Linoleic acid also induced in vitro migration of MDA-MB-231. By contrast, other FFAs tested had little or no effect on PAI-1 expression or migration. Linoleic acid-induced breast cancer cell migration was completely inhibited by virally expressed antisense PAI-1 RNA. Furthermore, increased expression of PAI-1 by FFAs was not detected in the SMAD4-deficient MDA-MB-468 breast carcinoma cells. Electrophoretic mobility-shift assay confirmed that linoleic acid-induced expression of PAI-1 was mediated, at least in part, by SMAD4 in MDA-MB-231 cells. That linoleic acid induces PAI-1 expression in breast cancer cells through SMAD4 provides a novel insight into understanding the relationships between two migration-associated molecules, FFAs, and PAI-1.

Byon, Chang Hyun; Hardy, Robert W; Ren, Changchun; Ponnazhagan, Selvarangan; Welch, Danny R; McDonald, Jay M; Chen, Yabing

2010-01-01

100

Fatty acid shifts and metabolic activity changes of Schizochytrium sp. S31 cultured on glycerol.  

PubMed

DHA production by Schizochytrium sp. S31 was studied in batch cultures on glycerol with stepwise dissolved oxygen strategy. Three growth stages were identified as cell growth, lipid accumulation and lipid turnover. It was revealed that fatty acid (FA) shifts during the three growth stages involved the activity changes of glycerol kinase (GK), FAD(+)-dependent glycerol-3-phosphate dehydrogenase (FAD(+)-G-3-PDH), malic enzyme (ME), ATP citrate lyase (ACL) and NAD(+)-dependent isocitrate dehydrogenase (NAD(+)-ICDH). Glycerol dissimilation in Schizochytrium sp. S31 was suggested via a phosphorylation by GK and a following oxidation by FAD(+)-G-3-PDH. Lipid accumulation of this strain was a growth-associated process, but the assimilable nitrogen depletion enhanced the accumulation of lipids. The exhaustion of glycerol induced the lipid turnover stage, where the short chain fatty acids were preferentially degraded and converted into lipid-free biomass (Xf) which was correlated to the increase of DHA content in biomass. PMID:23743430

Chang, Guifang; Luo, Zhenglin; Gu, Sitian; Wu, Qinghang; Chang, Ming; Wang, Xingguo

2013-05-16

101

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

PubMed

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

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

2012-10-19

102

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

PubMed Central

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

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

1995-01-01

103

BIOSYNTHESIS OF TETRAHYDROFURANYL FATTY ACIDS  

Technology Transfer Automated Retrieval System (TEKTRAN)

Clavibacter sp. ALA2 converts linoleic acid into many novel oxygenated products including hydroxy fatty acids and tetrahydrofuranyl unsaturated fatty acids (THFAs). One of them was tentatively identified by GC/MS as 12,13,16-trihydroxy-9(z)-octadecenoic acid (12,13,16-THOA, Hou et al. J Am. Oil Che...

104

The Influence of Polyunsaturated Fatty Acids on the Phospholipase D Isoforms Trafficking and Activity in Mast Cells  

PubMed Central

The impact of polyunsaturated fatty acid (PUFA) supplementation on phospholipase D (PLD) trafficking and activity in mast cells was investigated. The enrichment of mast cells with different PUFA including ?-linolenic acid (LNA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), linoleic acid (LA) or arachidonic acid (AA) revealed a PUFA-mediated modulation of the mastoparan-stimulated PLD trafficking and activity. All PUFA examined, except AA, prevented the migration of the PLD1 to the plasma membrane. For PLD2 no PUFA effects on trafficking could be observed. Moreover, PUFA supplementation resulted in an increase of mastoparan-stimulated total PLD activity, which correlated with the number of double bonds of the supplemented fatty acids. To investigate, which PLD isoform was affected by PUFA, stimulated mast cells were supplemented with DHA or AA in the presence of specific PLD-isoform inhibitors. It was found that both DHA and AA diminished the inhibition of PLD activity in the presence of a PLD1 inhibitor. By contrast, only AA diminished the inhibition of PLD activity in the presence of a PLD2 inhibitor. Thus, PUFA modulate the trafficking and activity of PLD isoforms in mast cells differently. This may, in part, account for the immunomodulatory effect of unsaturated fatty acids and contributes to our understanding of the modulation of mast cell activity by PUFA.

Basiouni, Shereen; Fuhrmann, Herbert; Schumann, Julia

2013-01-01

105

Novel surface-active oligofructose fatty acid mono-esters by enzymatic esterification.  

PubMed

This article describes the synthesis of a series of oligofructose monoesters with fatty acids of different chain length (C8, C12, C16 and C18) to obtain food-grade surfactants with a range of amphiphilicity. Reactions were performed in a mixture of DMSO/Bu(t)OH (10/90 v/v) at 60°C and catalysed by immobilised Candida antarctica lipase B. MALDI-TOF-MS analysis showed that the crude reaction products were mixtures of unmodified oligofructose and mostly mono-esters. The conversion into mono-esters increased with the length of the fatty acid chain, reflecting the specificity of the lipase towards more lipophilic substrates. Reverse phase solid phase extraction was used to fractionate the products, which lead to sufficient purity (>93%) of the fatty acid esters for functionality testing. It was shown that derivatives of longer (C16 and C18) fatty acids were more efficient in lowering surface tension and gave a much higher dilatational modulus than derivatives of the shorter (C8 and C12) fatty acids. PMID:23411321

van Kempen, Silvia E H J; Boeriu, Carmen G; Schols, Henk A; de Waard, Pieter; van der Linden, Erik; Sagis, Leonard M C

2012-11-16

106

Effects of intracerebroventricular injections of free fatty acids, lysophospholipids, or platelet activating factor in a mouse model of orofacial pain  

Microsoft Academic Search

The present study was carried out to determine the effects of central nervous free fatty acids, lysophospholipids, or platelet activating factor (PAF), in a mouse facial carrageenan injection model of orofacial pain. Mice that received intracerebroventricular (I.C.V.) injection of arachidonic acid or oleic acid showed significantly reduced allodynia and behavioral responses to von Frey hair stimulation of a carrageenan-injected area

Wajiha H. Vahidy; Wei-Yi Ong; Akhlaq A. Farooqui; Jin-Fei Yeo

2006-01-01

107

trans Fatty acids in milkfat  

Microsoft Academic Search

Milkfat is extremely complex, with ca. 500 different fatty acids reported in the triglycerides. Seasonal feed variation results\\u000a in higher unsaturated fatty acid levels in summer than in winter. Rumen microbes hydrogenate unsaturated feed lipids to yield\\u000a a mixture of geometrical and positional isomers which are transmitted to the milk. Total isolatedtrans fatty acids in milkfat reported in the literature

L. Deman; J. M. Deman

1983-01-01

108

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

2011-12-30

109

The role of fatty acids and caveolin-1 in tumor necrosis factor alpha-induced endothelial cell activation.  

PubMed

Hypertriglyceridemia and associated high circulating free fatty acids are important risk factors for atherosclerosis. In contrast to omega-3 fatty acids, linoleic acid, the major omega-6 unsaturated fatty acid in the American diet, may be atherogenic by amplifying an endothelial inflammatory response. We hypothesize that omega-6 and omega-3 fatty acids can differentially modulate tumor necrosis factor alpha (TNF-alpha)-induced endothelial cell activation and that functional plasma membrane microdomains called caveolae are required for endothelial cell activation. Caveolae are particularly abundant in endothelial cells and play a major role in endothelial trafficking and the regulation of signaling pathways associated with the pathology of vascular diseases. To test our hypothesis, endothelial cells were preenriched with either linoleic acid or alpha-linolenic acid before TNF-alpha-induced endothelial activation. Measurements included oxidative stress and nuclear factor kappaB-dependent induction of cyclooxygenase-2 (COX-2) and prostaglandin E(2) (PGE(2)) under experimental conditions with intact caveolae and with cells in which caveolin-1 was silenced by small interfering RNA. Exposure to TNF-alpha induced oxidative stress and inflammatory mediators, such as p38 mitogen-activated protein kinase (MAPK), nuclear factor kappaB, COX-2, and PGE(2), which were all amplified by preenrichment with linoleic acid but blocked or reduced by alpha-linolenic acid. The p38 MAPK inhibitor SB203580 blocked TNF-alpha-mediated induction of COX-2 protein expression, suggesting a regulatory mechanism through p38 MAPK signaling. Image overlay demonstrated TNF-alpha-induced colocalization of TNF receptor type 1 with caveolin-1. Caveolin-1 was significantly induced by TNF-alpha, which was further amplified by linoleic acid and blocked by alpha-linolenic acid. Furthermore, silencing of the caveolin-1 gene completely blocked TNF-alpha-induced production of COX-2 and PGE(2) and significantly reduced the amplified response of linoleic acid plus TNF-alpha. These data suggest that omega-6 and omega-3 fatty acids can differentially modulate TNF-alpha-induced inflammatory stimuli and that caveolae and its fatty acid composition play a regulatory role during TNF-alpha-induced endothelial cell activation and inflammation. PMID:18803934

Wang, Lei; Lim, Eun-Jin; Toborek, Michal; Hennig, Bernhard

2008-10-01

110

Age-related changes in fatty acid profile and locomotor activity rhythms in Nothobranchius korthausae.  

PubMed

The life cycle of Nothobranchius korthausae, a Cyprinodontiformes fish, was studied in our laboratory to characterise the ageing process. Some morphological changes, such as spine curvature, skin colour, and fin and eye appearance are described. Growth and survival curves reflected a fast life cycle with rapid initial growth until 4weeks of age, after which the fish grew more slowly before reaching their final size in week 40. Senescence onset was established at week 48 with a decrease in spawn size and viability and a general decline in the animal's appearance (weight and colouration losses, caudal fin degradation, and cataractogenesis). The fatty acid composition changed with age, with high unsaturation in the adult stage as reflected by a high peroxidation index, a condition that is associated with high susceptibility to oxidative damage if elevated reactive oxygen species (ROS) production occurs. Senescent fish had an increase in monounsaturated fatty acid proportions and a lower peroxidation index (226.5±19.7 in adults versus 120.2±19.1 in senescent fish, P<0.05). The circadian system, as reflected by locomotor activity rhythms, showed noticeable changes with age. Twenty-four-week-old fish (adults) had a robust diurnal rhythm that showed a decrease in total activity, an increase in rhythm fragmentation, and a fall in amplitude and regularity with age. Changes were clearly reflected in the Circadian Function Index variations (0.56, 0.47 and 0.25 at 24, 48 and 72weeks of age, respectively). In conclusion, N. korthausae appears to be a species with appropriate characteristics for ageing studies because it manifests clear signs of progressive ageing. Comparing species of Nothobranchius genus with different lifespans may be useful for increasing our understanding of the ageing process. PMID:21896325

Lucas-Sánchez, A; Almaida-Pagán, P F; Madrid, J A; de Costa, J; Mendiola, P

2011-08-28

111

Increased flow of fatty acids toward beta-oxidation in developing seeds of Arabidopsis deficient in diacylglycerol acyltransferase activity or synthesizing medium-chain-length fatty acids.  

PubMed

Synthesis of polyhydroxyalkanoates (PHAs) from intermediates of fatty acid beta-oxidation was used as a tool to study fatty acid degradation in developing seeds of Arabidopsis. Transgenic plants expressing a peroxisomal PHA synthase under the control of a napin promoter accumulated PHA in developing seeds to a final level of 0. 06 mg g(-1) dry weight. In plants co-expressing a plastidial acyl-acyl carrier protein thioesterase from Cuphea lanceolata and a peroxisomal PHA synthase, approximately 18-fold more PHA accumulated in developing seeds. The proportion of 3-hydroxydecanoic acid monomer in the PHA was strongly increased, indicating a large flow of capric acid toward beta-oxidation. Furthermore, expression of the peroxisomal PHA synthase in an Arabidopsis mutant deficient in the enzyme diacylglycerol acyltransferase resulted in a 10-fold increase in PHA accumulation in developing seeds. These data indicate that plants can respond to the inadequate incorporation of fatty acids into triacylglycerides by recycling the fatty acids via beta-oxidation and that a considerable flow toward beta-oxidation can occur even in a plant tissue primarily devoted to the accumulation of storage lipids. PMID:10594123

Poirier, Y; Ventre, G; Caldelari, D

1999-12-01

112

Increased Flow of Fatty Acids toward ?-Oxidation in Developing Seeds of Arabidopsis Deficient in Diacylglycerol Acyltransferase Activity or Synthesizing Medium-Chain-Length Fatty Acids1  

PubMed Central

Synthesis of polyhydroxyalkanoates (PHAs) from intermediates of fatty acid ?-oxidation was used as a tool to study fatty acid degradation in developing seeds of Arabidopsis. Transgenic plants expressing a peroxisomal PHA synthase under the control of a napin promoter accumulated PHA in developing seeds to a final level of 0.06 mg g?1 dry weight. In plants co-expressing a plastidial acyl-acyl carrier protein thioesterase from Cuphea lanceolata and a peroxisomal PHA synthase, approximately 18-fold more PHA accumulated in developing seeds. The proportion of 3-hydroxydecanoic acid monomer in the PHA was strongly increased, indicating a large flow of capric acid toward ?-oxidation. Furthermore, expression of the peroxisomal PHA synthase in an Arabidopsis mutant deficient in the enzyme diacylglycerol acyltransferase resulted in a 10-fold increase in PHA accumulation in developing seeds. These data indicate that plants can respond to the inadequate incorporation of fatty acids into triacylglycerides by recycling the fatty acids via ?-oxidation and that a considerable flow toward ?-oxidation can occur even in a plant tissue primarily devoted to the accumulation of storage lipids.

Poirier, Yves; Ventre, Giovanni; Caldelari, Daniela

1999-01-01

113

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

114

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

115

Intestinal metabolism of fatty acids  

PubMed Central

1. The effect of concentration on the oxidation and incorporation into lipids of lauric acid and linoleic acid by rings of rat small intestine has been studied in vitro. 2. In the absence of glucose, the oxidation of lauric acid in the range 0·01–5·0mm showed a maximum at 0·1mm. In the presence of glucose the maximum was at 0·5mm. The oxidation of linoleic acid in the presence of glucose increased throughout the concentration range 0·01–5·0mm. 3. The incorporation of lauric acid into lipids was maximal at 0·5–0·6mm in the presence of glucose, but at 10mm in the absence of glucose. At 0·8mm-lauric acid, in the presence of glucose, over 75% of the incorporated lauric acid was in triglycerides, but at 10mm they only contained 30%. The incorporation of glucose carbon into glycerides paralleled the incorporation of lauric acid. 4. In the range 0·01–2·5mm-linoleic acid the quantity incorporated into lipids increased. In the range 0·01–0·4mm linoleic acid was incorporated predominantly into triglycerides, but between 0·4 and 1·0mm most was in diglycerides, and between 2·5 and 5·0mm most was in monoglycerides. 5. The relationship of fatty acid concentration to the mechanism of absorption is discussed, together with the correlation between the distribution of the absorbed fatty acids within the tissue lipids and the lipase activity of intestinal mucosa.

Enser, M.

1965-01-01

116

Impact of fatty acids on human UDP-glucuronosyltransferase 1A1 activity and its expression in neonatal hyperbilirubinemia  

PubMed Central

While breast milk has been known as a cause of neonatal hyperbilirubinemia, the underlying mechanism of breast milk-induced jaundice has not been clarified. Here, the impact of fatty acids on human UDP-glucuronosyltransferase (UGT) 1A1 – the sole enzyme that can metabolize bilirubin – were examined. Oleic acid, linoleic acid, and docosahexaenoic acid (DHA) strongly inhibited UGT1A1 activity. Forty-eight hours after a treatment with a lower concentration of DHA (10?mg/kg), total bilirubin significantly increased in neonatal hUGT1 mice, which are human neonatal jaundice models. In contrast, treatments with higher concentrations of fatty acids (0.1–10?g/kg) resulted in a decrease in serum bilirubin in hUGT1 mice. It was further demonstrated that the treatment with higher concentrations of fatty acids induced UGT1A1, possibly by activation of peroxisome proliferator-activated receptors. Our data indicates that activation of peroxisome proliferator-activated receptors would increase UGT1A1 expression, resulting in reduction of serum bilirubin levels in human infants.

Shibuya, Ayako; Itoh, Tomoo; Tukey, Robert H.; Fujiwara, Ryoichi

2013-01-01

117

Basic Biological Sciences The Effects of Fatty Acids and Their Monoesters on the Metabolic Activity of Dental Plaque  

Microsoft Academic Search

We examined the effects of the saturated series of fatty acids and their esters on plaque bacterial metabolism. Fatty acids with a chain length of 8-15 carbons inhibited Streptococcus mutans and dental plaque in vitro. The glycerol monoesters with a fatty acid chain of 10-14 carbons were inhibitory to a similar extent. The glycolipid (sucrose monolaurate) reduced plaque bacterial glycolysis

M. L. Hayes

1984-01-01

118

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

Microsoft Academic Search

The effects on drug metabolizing enzymes of cyclopropenoid fatty acids present in baobab seed oil were evaluated in rats fed either a diet with baobab seed oil (1.27% cyclopropenoid fatty acids in the diet) or a diet with heated baobab seed oil (0.046% cyclopropenoid fatty acids in the diet). Comparison was made with rats fed a mixture of oils that

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

1995-01-01

119

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

PubMed

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

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

2013-02-07

120

Biological denitrification of brine: the effect of compatible solutes on enzyme activities and fatty acid degradation.  

PubMed

The effect of the addition of compatible solutes (ectoine and trehalose) on the denitrification process of saline wastewater was studied. In saline wastewater, it was observed that the initial concentration of nitrates was 500 mg N l?ą. A fatty substance isolated from oiled bleaching earth (waste of vegetable oil refining process) was used as a source of carbon.The consortium, which was responsible for the denitrification process originated from the wastewater of the vegetable oil industry. The consortium of microorganisms was identified by the use of restriction fragment length polymorphism of 16S rRNA gene amplicons and sequencing techniques. It was noted that ectoine affects significantly the activity of lipase and nitrate reductase, and resulted in faster denitrification compared to saline wastewater with the addition of trehalose or control saline wastewater (without compatible solutes). It was observed that relative enzyme activities of lipase and nitrate reductase increased by 32 and 35%, respectively, in the presence of 1 mM ectoine. This resulted in an increase in specific nitrate reduction rate in the presence of 1 mM ectoine to 5.7 mg N g?ą VSS h?ą, which was higher than in the absence of ectoine (3.2 mg N g?ą VSS h?ą). The addition of trehalose did not have an effect on nitrate removals. Moreover, it was found that trehalose was used up completely by bacteria as a source of carbon in the denitrification process. The fatty acids were biodegraded by 74% in the presence of 1 mM ectoine. PMID:22286267

Cyplik, Pawe?; Piotrowska-Cyplik, Agnieszka; Marecik, Roman; Czarny, Jakub; Drozdzy?ska, Agnieszka; Chrzanowski, ?ukasz

2012-09-01

121

Fatty acid amide hydrolase inhibitors. 3: tetra-substituted azetidine ureas with in vivo activity.  

PubMed

We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. PMID:22209458

Roughley, Stephen D; Browne, Helen; Macias, Alba T; Benwell, Karen; Brooks, Teresa; D'Alessandro, Jalanie; Daniels, Zoe; Dugdale, Sarah; Francis, Geraint; Gibbons, Ben; Hart, Terance; Haymes, Timothy; Kennett, Guy; Lightowler, Sean; Matassova, Natalia; Mansell, Howard; Merrett, Angela; Misra, Anil; Padfield, Anthony; Parsons, Rachel; Pratt, Robert; Robertson, Alan; Simmonite, Heather; Tan, Kiri; Walls, Steven B; Wong, Melanie

2011-12-13

122

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

Microsoft Academic Search

The cell intrinsic innate immune responses provide a first line of defense against viral infection, and often function by targeting cellular pathways usurped by the virus during infection. In particular, many viruses manipulate cellular lipids to form complex structures required for viral replication, many of which are dependent on de novo fatty acid synthesis. We found that the energy regulator

Theresa S. Moser; Daniel Schieffer; Sara Cherry

2012-01-01

123

Aedes aegypti (Diptera: Culicidae) Biting Deterrence: Structure- Activity Relationship of Saturated and Unsaturated Fatty Acids.  

National Technical Information Service (NTIS)

In this study we evaluated the biting deterrent effects of a series of saturated and unsaturated fatty acids against Aedes aegypti (L), yellow fever mosquito (Diptera: Culicidae) using the K &D bioassay module system. Saturated(C6:0 to C16:0 and C18:0) an...

A. Ali C. L. Cantrell J. C. Schneider S. O. Duke U. R. Bernier

2012-01-01

124

Fatty Acids and Atherosclerotic Risk  

Microsoft Academic Search

Most research concerning the effects of dietary fatty acids on atherosclerotic risk has focused on their effects on lipid and lipoprotein metabolism. However, it is known that fatty acids also influence a number of other relevant mechanisms involved in atherosclerosis such as lipid peroxidation, inflammation and haemostasis. The most favourable distribution of cholesterol over the various lipoproteins is achieved when

M. A. Thijssen; R. P. Mensink

125

Peroxisome-proliferator-activated receptor delta mediates the effects of long-chain fatty acids on post-confluent cell proliferation.  

PubMed Central

Nutritional long-chain fatty acids control adipose tissue mass by regulating the number and the size of adipocytes. It is now established that peroxisome-proliferator-activated receptors (PPARs) play crucial functions in the control of gene expression and the level of cell differentiation. PPARgamma, which is activated by specific prostanoids, is a key factor in activating terminal differentiation and adipogenesis. We have recently demonstrated that PPARdelta, once activated by fatty acids, drives the expression of a limited set of genes, including that encoding PPARgamma, thereby inducing adipose differentiation. Thus far, the mechanism of action of fatty acids in the control of preadipocyte proliferation has remained unknown. We show here that PPARdelta is directly implicated in fatty acid-induced cell proliferation. Ectopic expression of PPARdelta renders 3T3C2 cells capable of responding to treatment with long-chain fatty acids by a resumption of mitosis, and this effect is limited to a few days after confluence. This response is restricted to PPARdelta activators and, for fatty acids, takes place within the range of concentrations found to trigger differentiation of preadipocytes both in vitro and in vivo. Furthermore, the use of a mutated inactive PPARdelta demonstrated that transcriptional activity of the nuclear receptor is required to mediate fatty acid-induced proliferation. These data demonstrate that PPARdelta, as a transcription factor, is directly implicated in fatty acid-induced proliferation, and this could explain the hyperplastic development of adipose tissue that occurs in high-fat-fed animals.

Jehl-Pietri, C; Bastie, C; Gillot, I; Luquet, S; Grimaldi, P A

2000-01-01

126

Fatty acids with antibacterial activity from the cyanobacterium Oscillatoria redekei HUB 051  

Microsoft Academic Search

Bioassay-guided fractionation of the n-hexane extract prepared from the biomass of the cyanobacterium Oscillatoria redekei syn. Limnothrix redekei HUB 051 by silica gel and RP-18 column chromatography followed by HPLC resulted in the isolation of a mixture of two unsaturated hydroxy fatty acids. Their further separation using normal phase HPLC resulted in the identification of a-dimorphecolic acid, a 9-hydroxy-10E, 12Z-octadecadienoic

Sabine Mundt; Susann Kreitlow; Rolf Jansen

2003-01-01

127

An ethanol extract of Artemisia iwayomogi activates PPAR? leading to activation of fatty acid oxidation in skeletal muscle.  

PubMed

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

2012-03-27

128

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

Microsoft Academic Search

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

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

2004-01-01

129

[Determination of three active ingredients in food additive sucrose fatty acid ester by TLC scanning].  

PubMed

A method of separation and quantitation of monoester, diester and triester in food additive sucrose fatty acid esters by TLC with dual-wavelength TLC scanner in the sawtooth scanning mode is described. The detective wavelength was 530 nm and the reference wavelength was 700 nm. A mixture of chloroform, methanol, acetic acid and water (80:10:8:1, V/V) was used as mobile phase. The calibration curve was linear over a range from 4 micrograms to 60 micrograms with correlation coefficients of 0.9949-0.9980. The average recoveries were 96.45%-98.73% (n = 3, RSD = 2.7%-3.2%). This method is accurate, simple and dependable, with a wide range of linearity. It has been applied to the analysis of various samples and can be used for the quality control of the food additive sucrose fatty acid ester. PMID:12541521

Xie, X T; Zhang, H P; Zheng, P; Luo, C Y

2000-07-01

130

Fatty acid remodeling in cellular glycerophospholipids following the activation of human T cells.  

PubMed

Changes in fatty acid (FA) and glycerophospholipid (GPL) metabolism associated with cell cycle entry are not fully understood. In this study FA-GPL remodeling was investigated in resting and proliferating primary human T cells. Significant changes were measured in the composition and distribution of FAs in GPLs following receptor activation of human T cells. The FA distribution of proliferating T cells was very similar to that of the human Jurkat T cell line and when the stimulus was removed from proliferating T cells, they stopped proliferating and the FA distribution largely reverted back to that of resting T cells. The cellular content of saturated and monounsaturated FAs was significantly increased in proliferating cells, which was associated with an induction of FA synthase and stearoyl-CoA desaturase-1 gene expression. Additionally, cellular arachidonate was redistributed in GPLs in a distinct pattern that was unlike any other FAs. This redistribution was associated with an induction of CoA-dependent and CoA-independent remodeling. Accordingly, significant changes in the expression of several acyl-CoA synthetases, lysophospholipid acyltransferases, and phospholipase A2 were measured. Overall, these results suggest that metabolic pathways are activated in proliferating T cells that may represent fundamental changes associated with human cell proliferation. PMID:23894206

Robichaud, Philippe Pierre; Boulay, Katherine; Munganyiki, Jean Éric; Surette, Marc E

2013-07-26

131

Antioxidative activity of phenolic acids on triacylglycerols and fatty acid methyl esters from olive oil  

Microsoft Academic Search

The autoxidation of kinetically pure triacylglycerols and methyl esters of olive oil (TGOO and MEOO) in the presence of four different concentrations of p-coumaric, ferulic and caffeic acids at 100 °C was studied. It was established that effectiveness and strength of the phenolic acids were greater in MEOO than in TGOO. In both lipid substates the molecules of phenolic acids

Emma M. Marinova; Nedjalka Vl. Yanishlieva

1996-01-01

132

Role of fatty acid transporters in epidermis  

PubMed Central

Skin epidermis is an active site of lipid synthesis. The intercellular lipids of human stratum corneum (SC) are unique in composition and quite different from the lipids found in most biological membranes. The three major lipids in the SC are free fatty acids, cholesterol and ceramides. Fatty acids can be synthesized by keratinocytes de novo and, in addition, need to be taken up from the circulation. The latter process has been shown to be protein mediated, and several fatty acid transporters are expressed in skin. Recent studies of transgenic and knockout animal models for fatty acid transporters and the identification of fatty acid transport protein 4 (FATP4 or SLC27A4) mutations as causative for Ichthyosis Prematurity Syndrome highlight the vital roles of fatty acid transport and metabolism in skin homeostasis. This review provides an overview of our current understanding of the role of fatty acids and their transporters in cutaneous biology, including their involvement in epidermal barrier generation and skin inflammation.

Miner, Jeffrey H; Jahnsen, Frode

2011-01-01

133

Enzymatic preparation of polyethylene glycol esters of castor oil fatty acids and their surface-active properties  

Microsoft Academic Search

This study concerns the preparation and evaluation of nonionic surfactants prepared from polyethylene glycol (PEG) esters\\u000a of castor oil fatty acid, a source of hydroxy fatty acid. A lipase-catalyzed esterification reaction has been employed to\\u000a prepare PEG esters of hydroxy acid to overcome problems associated with chemical processes. Castor oil fatty acid (85% ricinoleic\\u000a acid) was mixed with PEG of

M. Ghosh; D. K. Bhattacharyya

1998-01-01

134

Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.  

PubMed

Two major isoforms of human carboxylesterases (CEs) are found in metabolically active tissues, CES1 and CES2. These hydrolytic enzymes are involved in xenobiotic and endobiotic metabolism. CES1 is abundantly expressed in human liver and monocytes/macrophages, including the THP1 cell line; CES2 is expressed in liver but not in monocytes/macrophages. The cholesteryl ester hydrolysis activity in human macrophages has been attributed to CES1. Here, we report the direct inhibitory effects of several endogenous oxysterols and fatty acids on the CE activity of THP1 monocytes/macrophages and recombinant human CES1 and CES2. Using THP1 whole-cell lysates we found: (1) 27-hydroxycholesterol (27-HC) is a potent inhibitor of carboxylesterase activity (IC50=33 nM); (2) 24(S),25-epoxycholesterol had moderate inhibitory activity (IC(50)=8.1 microM); and (3) cholesterol, 7-ketocholesterol, 22(R)-hydroxycholesterol, 24(S)-hydroxycholesterol, and 25-hydroxycholesterol each had little inhibitory activity. 27-HC was a partially noncompetitive inhibitor of recombinant CES1 (K(iapp)=10 nM) and impaired intracellular CES1 activity following treatment of intact THP1 cells. In contrast, recombinant CES2 activity was not inhibited by 27-HC, suggesting isoform-selective inhibition by 27-HC. Furthermore, unsaturated fatty acids were better inhibitors of CES1 activity than saturated fatty acids, while CES2 activity was unaffected by any fatty acid. Arachidonic acid (AA) was the most potent fatty acid inhibitor of recombinant CES1 and acted by a noncompetitive mechanism (K(iapp)=1.7 microM); when not complexed to albumin, exogenous AA penetrated intact THP1 cells and inhibited CES1. Inhibition results are discussed in light of recent structural models for CES1 that describe ligand binding sites separate from the active site. In addition, oxysterol-mediated inhibition of CES1 activity was demonstrated by pretreatment of human liver homogenates or intact THP1 cells with exogenous 27-HC, which resulted in significantly reduced hydrolysis of the pyrethroid insecticide bioresmethrin, a CES1-specific xenobiotic substrate. Collectively, these findings suggest that CE activity of recombinant CES1, cell lysates, and intact cells can be impaired by naturally occurring lipids, which may compromise the ability of CES1 to both detoxify environmental pollutants and metabolize endogenous compounds in vivo. PMID:19761868

Crow, J Allen; Herring, Katye L; Xie, Shuqi; Borazjani, Abdolsamad; Potter, Philip M; Ross, Matthew K

2009-09-15

135

Mammalian Fatty Acid Synthase Activity From Crude Tissue Lysates Tracing [13C]-Substrates Using GC Mass Spectrometry  

PubMed Central

Fatty Acid Synthase (FASN, FAS; EC 2.3.1.85) is the sole mammalian enzyme to synthesize fatty acids de novo from acetyl and malonyl coenzyme A esters. A new method is described that directly quantifies uniformly labeled [13C]16-palmitate by tracing [13C]2-acetyl-CoA and [13C]3-malonyl-CoA using an in vitro FASN assay. This method used GC-MS to detect [13C]16-palmitate carboxylate anions (m/z 271) of pentafluorobenzyl derivatives and was highly sensitive at femtomole quantities. Uniformly incorporated [13C]16-palmitate was the primary product of both recombinant and crude tissue lysate FASN. Quantification of FASN protein within crude tissue lysates assured equal FASN amounts, preserved steady state kinetics, and enabled calculation of FASN specific activity. FASN activity determined by [13C]16-palmitate synthesis was consistent with values obtained from NADPH oxidation assays. Analysis of FASN activity from tissue extracts was not hampered by contaminating enzymes or pre-existing fatty acids. Crude mammary gland and liver lysates had significantly different activities at 82 and 65 nmoles minute?1 mg?1 respectively, suggesting tissue specific activity levels differ in a manner unrelated to FASN amount. GC-MS quantification of [13C]16-palmitate synthesis permits sensitive evaluation of FASN activity from tissues of varied physiologic states, and of purified FASN activity in the presence of modifying proteins, enzymes, or drugs.

Rudolph, Michael C.; Maluf, N. Karl; Wellberg, Elizabeth A.; Johnson, Chris A.; Murphy, Robert C.; Anderson, Steve M.

2012-01-01

136

Choline-phosphate cytidyltransferase activity and phosphatidylcholine synthesis in rat granular pneumocytes are increased with exogenous fatty acids.  

PubMed

We investigated the effect of exogenous fatty acids on phosphatidylcholine (PC) and disaturated phosphatidylcholine (DSPC) synthesis by rat granular pneumocytes in primary culture. Synthesis of PC and DSPC from [3H-methyl]choline, as evaluated by increasing specific activity (pmol choline incorporated/microgram phosphorus), was linear for 3 h. Exogenous palmitic, oleic, linoleic, or linolenic acid (100 microM each) increased the synthesis of PC by approx. 50% during incubation for 3 h. In contrast, synthesis of DSPC was increased only by palmitic acid. The increase in DSPC synthesis was approx. 150% after 3 h. Conversion of choline phosphate to PC was increased in the presence of palmitic or oleic acid as indicated by pulse-chase studies with [3H-methyl]choline in the intact cells. Cells incubated for 3 h with either oleic or palmitic acid showed increased choline-phosphate cytidyltransferase activity in the cells and the microsomal fraction. In addition, oleic acid increased the activity of this enzyme in the cytosolic fraction. The distribution of this enzyme in cytosolic and microsomal fraction was 24 and 76% in the cells incubated with palmitic acid and 32 and 68% in control cells. These results suggest that exogenous fatty acids stimulate the de novo pathway of PC synthesis in granular pneumocytes by increasing the microsomal choline-phosphate cytidyltransferase activity. PMID:2893643

Chander, A; Fisher, A B

1988-02-19

137

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

138

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

139

Carbon flux and fatty acid synthesis in plants  

Microsoft Academic Search

The de novo synthesis of fatty acids in plants occurs in the plastids through the activity of fatty acid synthetase. The synthesis of the malonyl-coenzyme A that is required for acyl-chain elongation requires the import of metabolites from the cytosol and their subsequent metabolism. Early studies had implicated acetate as the carbon source for plastidial fatty acid synthesis but more

Stephen Rawsthorne

2002-01-01

140

Fatty acid synthesizing enzymes intrinsic to myelin  

Microsoft Academic Search

A recent study showing incorporation of acetyl groups from neuronal N-acetylaspartate into myelin lipids suggested the presence of fatty acid synthesizing enzymes in myelin that utilize the acetyl groups liberated by myelin-associated aspartoacylase [J. Neurochem. 78 (2001) 736]. We report here detection of the fatty acid synthase (FAS) complex and acetyl-CoA carboxylase (ACC) in purified myelin. The activity of myelin

Goutam Chakraborty; Robert Ledeen

2003-01-01

141

Omega-3 fatty acids lower blood pressure by directly activating large-conductance Ca˛?-dependent K? channels.  

PubMed

Long-chain polyunsaturated omega-3 fatty acids such as docosahexaenoic acid (DHA), found abundantly in oily fish, may have diverse health-promoting effects, potentially protecting the immune, nervous, and cardiovascular systems. However, the mechanisms underlying the purported health-promoting effects of DHA remain largely unclear, in part because molecular signaling pathways and effectors of DHA are only beginning to be revealed. In vascular smooth muscle cells, large-conductance Ca(2+)- and voltage-activated K(+) (BK) channels provide a critical vasodilatory influence. We report here that DHA with an EC50 of ?500 nM rapidly and reversibly activates BK channels composed of the pore-forming Slo1 subunit and the auxiliary subunit ?1, increasing currents by up to ?20-fold. The DHA action is observed in cell-free patches and does not require voltage-sensor activation or Ca(2+) binding but involves destabilization of the closed conformation of the ion conduction gate. DHA lowers blood pressure in anesthetized wild-type but not in Slo1 knockout mice. DHA ethyl ester, contained in dietary supplements, fails to activate BK channels and antagonizes the stimulatory effect of DHA. Slo1 BK channels are thus receptors for long-chain omega-3 fatty acids, and these fatty acids--unlike their ethyl ester derivatives--activate the channels and lower blood pressure. This finding has practical implications for the use of omega-3 fatty acids as nutraceuticals for the general public and also for the critically ill receiving omega-3-enriched formulas. PMID:23487785

Hoshi, Toshinori; Wissuwa, Bianka; Tian, Yutao; Tajima, Nobuyoshi; Xu, Rong; Bauer, Michael; Heinemann, Stefan H; Hou, Shangwei

2013-03-04

142

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

PubMed Central

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

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

2008-01-01

143

High activity of fatty acid oxidation enzymes in human placenta: Implications for fetal-maternal disease  

Microsoft Academic Search

As the human fetus and placenta are considered to be primarily dependent on glucose oxidation for energy metabolism, the cause\\u000a of the remarkable association between severe maternal pregnancy complications and the carriage of a fetus with an inborn error\\u000a of mitochondrial long-chain fatty acid oxidation (FAO) has remained obscure. We analysed human term placenta and chorionic\\u000a villus samples for the

N. A. Oey; M. E. J. Den Boer; J. P. N. Ruiter; R. J. A. Wanders; M. Duran; H. R. Waterham; K. Boer; J. A. M. van der Post; F. A. Wijburg

2003-01-01

144

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

PubMed

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 alpha2 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

2005-03-17

145

Inhibitors of Fatty Acid Amide Hydrolase.  

National Technical Information Service (NTIS)

The present invention relates to inhibitors of fatty acid hydrolase. More particularly, the invention relates to inhibitors of fatty acid hydrolase employing a heterocyclic pharmacophore. One aspect of the invention is directed to an inhibitor of fatty ac...

D. L. Boger

2005-01-01

146

Dietary Medium-Chain Fatty Acids Raise and (n-3) Polyunsaturated Fatty Acids Lower Hepatic Triacylglycerol Synthesis in Rats12  

Microsoft Academic Search

The hypothesis tested was that dietary medium-chain or (n-3) polyunsaturated fatty acids, when compared with (n-6) polyunsaturated fatty acids, alter plasma triacylglycerol levels by affecting hepatic triacylglycerol synthesis as reflected by the activities of acetyl-CoA carboxylase, fatty acid synthase and di- acylglycerol acyltransferase in liver. In two separate experiments rats were fed purified diets containing (n-6) polyunsaturated fatty acids in

MATH J. H. GEELEN; WILLY J. SCHOOTS; C. BEYNEN

147

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.

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

148

Inhibition of c-Jun-N-terminal Kinase Increases Cardiac Peroxisome Proliferator-activated Receptor ? Expression and Fatty Acid Oxidation and Prevents Lipopolysaccharide-induced Heart Dysfunction*  

PubMed Central

Septic shock results from bacterial infection and is associated with multi-organ failure, high mortality, and cardiac dysfunction. Sepsis causes both myocardial inflammation and energy depletion. We hypothesized that reduced cardiac energy production is a primary cause of ventricular dysfunction in sepsis. The JNK pathway is activated in sepsis and has also been implicated in impaired fatty acid oxidation in several tissues. Therefore, we tested whether JNK activation inhibits cardiac fatty acid oxidation and whether blocking JNK would restore fatty acid oxidation during LPS treatment. LPS treatment of C57BL/6 mice and adenovirus-mediated activation of the JNK pathway in cardiomyocytes inhibited peroxisome proliferator-activated receptor ? expression and fatty acid oxidation. Surprisingly, none of the adaptive responses that have been described in other types of heart failure, such as increased glucose utilization, reduced ?MHC:?MHC ratio or induction of certain microRNAs, occurred in LPS-treated mice. Treatment of C57BL/6 mice with a general JNK inhibitor (SP600125) increased fatty acid oxidation in mice and a cardiomyocyte-derived cell line. JNK inhibition also prevented LPS-mediated reduction in fatty acid oxidation and cardiac dysfunction. Inflammation was not alleviated in LPS-treated mice that received the JNK inhibitor. We conclude that activation of JNK signaling reduces fatty acid oxidation and prevents the peroxisome proliferator-activated receptor ? down-regulation that occurs with LPS.

Drosatos, Konstantinos; Drosatos-Tampakaki, Zoi; Khan, Raffay; Homma, Shunichi; Schulze, P. Christian; Zannis, Vassilis I.; Goldberg, Ira J.

2011-01-01

149

Biological Control of Phytopathogenic Fungi by Fatty Acids  

Microsoft Academic Search

The aim of the present study was to evaluate the antifungal activity of fatty acids against phytopathogenic fungi. Two pot\\u000a experiments were conducted by mixing palmitic and oleic acids in the soil in which poor plant growth was observed. In addition,\\u000a the antifungal activities of nine fatty acids (butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic\\u000a acid,

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

2008-01-01

150

C1qTNF-related protein-6 mediates fatty acid oxidation via the activation of the AMP-activated protein kinase.  

PubMed

C1qTNF-related proteins (CTRPs) are involved in diverse processes including metabolism, inflammation host defense, apoptosis, cell differentiation, autoimmunity, hibernation, and organogenesis. However, the physiological role of CTRP6 remains poorly understood. Here we demonstrate that the globular domain of CTRP6 mediates the phosphorylation and activation of the 5'-AMP-activated protein kinase (AMPK) in skeletal muscle cells. In parallel with the activation of AMPK, CTRP6 induces the phosphorylation of acetyl coenzyme A carboxylase (ACC) and fatty acid oxidation in myocytes. Thus, CTRP6 plays a role in fatty acid metabolism via the AMPK-ACC pathway. PMID:20102710

Lee, Wan; Kim, Mi-Jin; Park, Eun-Ju; Choi, Young-Jin; Park, Seung-Yoon

2010-01-26

151

Biosynthesis of cyclopentenyl fatty acids. Cyclopentenylglycine, a non-proteinogenic amino acid as precursor of cyclic fatty acids in Flacourtiaceae.  

PubMed

In seeds of Hydnocarpus anthelminthica of Flacourtiaceae, cyclopentenylglycine and cyclopentenyl fatty acids are found naturally. The non-proteinogenic amino acid may serve as precursor of cyclopentenyl fatty acids via aleprolic acid, the starter molecule for these long-chain compounds. After administration of cyclopentenyl[2-14C]glycine to maturing seeds of H. anthelminthica, labelled cyclopentenyl fatty acids were synthesized. Comparative activities were observed, when [1-14C]aleprolic acid was supplied to the seeds. Incorporation studies with [1-14C]acetate revealed that the chain-lengthening systems for straight-chain and cyclic fatty acids were still functioning in mature seeds. Endosperm and embryo of H. Anthelminthica seeds synthesized cyclopentenyl fatty acids from cyclopentenyl[2-14C]glycine, [1-14C]aleprolic acid and [1-14C]acetate. In embryonic tissue, a dilution experiment proved the following path for cyclopentenyl fatty acid biosynthesis: cyclopentenylglycine leads to aleprolic acid leads to cyclopentenyl fatty acids. The conversion of cyclopentenylglycine to aleprolic acid may occur via transamination and oxidative decarboxylation; activated aleprolic acid is then lengthened by C2-units to cyclopentenyl fatty acids. PMID:856584

Cramer, U; Spener, F

1977-04-15

152

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2013 CFR

...acids and their associated fatty acids manufactured from fats and oils derived from edible sources: Capric acid, caprylic acid, lauric acid, myristic acid, oleic acid, palmitic acid, and stearic acid. (b) The food additive meets the...

2013-04-01

153

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2010 CFR

...acids and their associated fatty acids manufactured from fats and oils derived from edible sources: Capric acid, caprylic acid, lauric acid, myristic acid, oleic acid, palmitic acid, and stearic acid. (b) The food additive meets the...

2009-04-01

154

21 CFR 172.860 - Fatty acids.  

Code of Federal Regulations, 2010 CFR

...acids and their associated fatty acids manufactured from fats and oils derived from edible sources: Capric acid, caprylic acid, lauric acid, myristic acid, oleic acid, palmitic acid, and stearic acid. (b) The food additive meets the...

2010-01-01

155

Effects of dietary saturated and Trans fatty acids on tissue lipid composition and serum LCAT activity in the rat  

Microsoft Academic Search

Groups of rats were fed from weaning with diets containing 5% by wt of hydrogenated coconut oil (HCO), safflower oil, or a\\u000a concentrate of ethyl elaidate and linolelaidate (TRANS) as the sole source of dietary fat. Fatty acid composition of the lipid\\u000a classes from serum, liver, heart, and kidney was determined, and the serum lecithin: cholesterol acyl transferase (LCAT) activities

T. Takatori; F. C. Phillips; H. Shimasaki; O. S. Privett

1976-01-01

156

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

Microsoft Academic Search

Observations were carried out on volatile fatty acid (VFA) concentrations, enzyme activities and the microflora of the rumen contents in heifers during transition from winter to pasture feeding and in the subsequent gazing cycles. After turn?out to pasture, total VFA concentrations in the rumen contents of heifers significantly decreased from 107.7 to 88.7 mmol.l (P < 0.01). After subsequent increase

R. Žit?an; A. Sommer; J. Gallo; A. Lauková; A. Bomba; J. Venglovský

1994-01-01

157

EFFECTS OF VITAMIN E ON ANTIOXIDANT ENZYME ACTIVITIES AND FATTY ACID COMPOSITIONS IN JUVENILE ABALONE HALIOTIS DISCUS HANNAI INO  

Microsoft Academic Search

A 240-day feeding trial was conducted in a recirculated water system to investigate the effects of dietary vitamin E on the activities of antioxidant enzymes (catalase, CAT; superoxide dismutase, SOD; glutathione peroxidase, GPX) and the composition of fatty acids in abalone, Haliotis discus hannai Ino. Triplicate groups of juvenile abalone (initial weight: 0.71± 0.00 g; initial shell length: 15.49± 0.04

JINGHUA FU; WENBING ZHANG; KANGSEN MAI; XIUNI FENG; WEI XU; ZHIGUO LIUFU; HONGMING MA; QINGHUI AI

2007-01-01

158

Kinetic analysis of waste activated sludge hydrolysis and short-chain fatty acids production at pH 10  

Microsoft Academic Search

The accumulation of short-chain fatty acids (SCFAs), a preferred carbon source for enhanced biological phosphorus removal microbes, was significantly improved when waste activated sludge (WAS) was fermented at pH 10. The kinetics of WAS hydrolysis and SCFAs production at pH 10 was investigated. It was observed that during WAS anaerobic fermentation the accumulation of SCFAs was limited by the hydrolysis

Leiyu FENG; Yuanyuan YAN; Yinguang CHEN

2009-01-01

159

Omega-3 fatty acid supplementation changes intracellular phospholipase A2 activity and membrane fatty acid profiles in individuals at ultra-high risk for psychosis.  

PubMed

The identification of an ultra-high risk (UHR) profile for psychosis and a greater understanding of its prodrome have led to increasing interest in early intervention to delay or prevent the onset of psychotic illness. In a randomized placebo-controlled trial, we have identified long-chain ?-3 (?-3) polyunsaturated fatty acid (PUFA) supplementation as potentially useful, as it reduced the rate of transition to psychosis by 22.6% 1 year after baseline in a cohort of 81 young people at UHR of transition to psychosis. However, the mechanisms whereby the ?-3 PUFAs might be neuroprotective are incompletely understood. Here, we report on the effects of ?-3 PUFA supplementation on intracellular phospholipase A2 (inPLA2) activity, the main enzymes regulating phospholipid metabolism, as well as on peripheral membrane lipid profiles in the individuals who participated in this randomized placebo-controlled trial. Patients were studied cross-sectionally (n=80) and longitudinally (n=65) before and after a 12-week intervention with 1.2?g per day ?-3 PUFAs or placebo, followed by a 40-week observation period to establish the rates of transition to psychosis. We investigated inPLA2 and erythrocyte membrane FAs in the treatment groups (?-3 PUFAs vs placebo) and the outcome groups (psychotic vs non-psychotic). The levels of membrane ?-3 and ?-6 PUFAs and inPLA2 were significantly related. Some of the significant associations (that is, long-chain ?-6 PUFAs, arachidonic acid) with inPLA2 activity were in opposite directions in individuals who did (a positive correlation) and who did not (a negative correlation) transition to psychosis. Supplementation with ?-3 PUFA resulted in a significant decrease in inPLA2 activity. We conclude that ?-3 PUFA supplementation may act by normalizing inPLA2 activity and ?-6-desaturase-mediated metabolism of ?-3 and ?-6 PUFAs, suggesting their role in neuroprogression of psychosis.Molecular Psychiatry advance online publication, 12 March 2013; doi:10.1038/mp.2013.7. PMID:23478748

Smesny, S; Milleit, B; Hipler, U-C; Milleit, C; Schäfer, M R; Klier, C M; Holub, M; Holzer, I; Berger, G E; Otto, M; Nenadic, I; Berk, M; McGorry, P D; Sauer, H; Amminger, G P

2013-03-12

160

Exchanging saturated fatty acids for (n-6) polyunsaturated fatty acids in a mixed meal may decrease postprandial lipemia and markers of inflammation and endothelial activity in overweight men.  

PubMed

Postprandial lipemia, low-grade systemic inflammation, and endothelial activity are related to metabolic disorders. It is well known that dietary fatty acid composition modulates postprandial lipemia, but information on the other metabolic risk markers is limited. We therefore studied the acute effects of a meal rich in SFA compared with those of a meal rich in (n-6) PUFA on postprandial responses in overweight men who are at an increased risk to develop the metabolic syndrome and its comorbidities. In a crossover design, the effects of 50 g butter (rich in SFA) on lipemia and markers for inflammation and endothelial activity were compared with those of 50 g sunflower oil [rich in (n-6) PUFA] during an 8-h postprandial mixed meal tolerance test in 13 overweight men. Postprandial changes in serum TG were comparable between the meals (P = 0.38), except for a reduction in the incremental area under the curve (P = 0.046) in the late postprandial phase after (n-6) PUFA (125 ± 96 mmol?min?L(-1)) compared with SFA (148 ± 98 mmol?min?L(-1)). Compared with the SFA meal, the (n-6) PUFA meal decreased plasma IL-6 (P = 0.003), TNF? (P = 0.005), soluble TNF receptors I and II (sTNFr; P = 0.024 and P < 0.001, respectively), and soluble vascular cell adhesion molecule-1 (sVCAM-1; P = 0.030) concentrations. These results indicate that exchanging SFA from butterfat for (n-6) PUFA in a mixed meal may decrease postprandial lipemia and concentrations of IL-6, TNF?, sTNFr-I and -II, and sVCAM-1 in overweight men. PMID:21430255

Masson, Christiaan J; Mensink, Ronald P

2011-03-23

161

Supercritical carbon dioxide extraction of seed oil from winter melon (Benincasa hispida) and its antioxidant activity and fatty acid composition.  

PubMed

In the present study, supercritical carbon dioxide (SC-CO(2)) extraction of seed oil from winter melon (Benincasa hispida) was investigated. The effects of process variables namely pressure (150-300 bar), temperature (40-50 °C) and dynamic extraction time (60-120 min) on crude extraction yield (CEY) were studied through response surface methodology (RSM). The SC-CO(2) extraction process was modified using ethanol (99.9%) as co-solvent. Perturbation plot revealed the significant effect of all process variables on the CEY. A central composite design (CCD) was used to optimize the process conditions to achieve maximum CEY. The optimum conditions were 244 bar pressure, 46 °C temperature and 97 min dynamic extraction time. Under these optimal conditions, the CEY was predicted to be 176.30 mg-extract/g-dried sample. The validation experiment results agreed with the predicted value. The antioxidant activity and fatty acid composition of crude oil obtained under optimized conditions were determined and compared with published results using Soxhlet extraction (SE) and ultrasound assisted extraction (UAE). It was found that the antioxidant activity of the extract obtained by SC-CO(2) extraction was strongly higher than those obtained by SE and UAE. Identification of fatty acid composition using gas chromatography (GC) showed that all the extracts were rich in unsaturated fatty acids with the most being linoleic acid. In contrast, the amount of saturated fatty acids extracted by SE was higher than that extracted under optimized SC-CO(2) extraction conditions. PMID:23322066

Bimakr, Mandana; Rahman, Russly Abdul; Taip, Farah Saleena; Adzahan, Noranizan Mohd; Sarker, Md Zaidul Islam; Ganjloo, Ali

2013-01-15

162

A novel method for the measurement of in vitro fatty acid 2-hydroxylase activity by gas chromatography-mass spectrometry  

Microsoft Academic Search

Fatty acid 2-hydroxylase (FA2H), encoded by the FA2H gene, is an enzyme responsible for the de novo syn- thesis of sphingolipids containing 2-hydroxy fatty acids. 2-Hydroxy sphingolipids are highly abundant in the brain, as major myelin galactolipids (galactosylceramide and sulfatide) contain a uniquely high proportion ( ? 50%) of 2-hydroxy fatty acids. Other tissues, such as epidermis, epi- thelia of

Nathan L. Alderson; Michael D. Wall; Hiroko Ham

2005-01-01

163

Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity  

Microsoft Academic Search

Lipase-catalyzed synthesis of different sugar fatty acid esters was performed in high yields in 2-methyl-2-butanol at atmospheric pressure and in supercritical carbon dioxide (SC CO2) at 10MPa. Influence of molecular sieves concentration on conversion in SC CO2 was studied. Growth inhibitory effect of commercial sucrose fatty acid esters and enzymatically synthesized sucrose and fructose fatty acid esters on Gram-positive and

Maja Habulin; Saša Šabeder; Željko Knez

2008-01-01

164

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.

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

2013-01-01

165

Long chain polyunsaturated fatty acid synthesis in a marine vertebrate: ontogenetic and nutritional regulation of a fatty acyl desaturase with ?4 activity.  

PubMed

Solea senegalensis is an unusual marine teleost as it has very low dietary requirement for long-chain polyunsaturated fatty acids (LC-PUFA) during early development. Aquaculture is rapidly becoming the main source of health-beneficial fish products for human consumption. This, associated with limited supply of LC-PUFA-rich ingredients for fish feeds, render S. senegalensis a highly interesting species in which to study the LC-PUFA biosynthesis pathway. We have cloned and functionally characterized fatty acyl desaturase and elongase cDNAs corresponding to ?4fad (with some ?5 activity for the n-3 series) and elovl5 with the potential to catalyze docosahexaenoic acid (DHA) biosynthesis from eicosapentaenoic acid (EPA). Changes in expression of both transcripts were determined during embryonic and early larval development, and transcriptional regulation in response to higher or lower dietary n-3 LC-PUFA was assessed during larval and post-larval stages. There was a marked pattern of regulation during early ontogenesis, with both transcripts showing peak expression coinciding with the start of exogenous feeding. Although elovl5 transcripts were present in fertilized eggs, ?4fad only appeared at hatching. However, eggs have high proportions of DHA (~20%) and high DHA/EPA ratio (~11) to meet the high demands for early embryonic development. The fatty acid profile of larvae after the start of exogenous feeding closely reflected dietary composition. Nonetheless, ?4fad was significantly up-regulated in response to LC-PUFA-poor diets, which may suggest biological relevance of this pathway in reducing LC-PUFA dietary requirements in this species, compared to other marine teleosts. These results indicate that sole is capable of synthesizing DHA from EPA through a Sprecher-independent pathway. PMID:22245719

Morais, Sofia; Castanheira, Filipa; Martinez-Rubio, Laura; Conceiçăo, Luis E C; Tocher, Douglas R

2012-01-08

166

REGULATION OF FATTY ACID SYNTHESIS.  

PubMed

All plant cells produce fatty acids from acetyl-CoA by a common pathway localized in plastids. Although the biochemistry of this pathway is now well understood, much less is known about how plants control the very different amounts and types of lipids produced in different tissues. Thus, a central challenge for plant lipid research is to provide a molecular understanding of how plants regulate the major differences in lipid metabolism found, for example, in mesophyll, epidermal, or developing seed cells. Acetyl-CoA carboxylase (ACCase) is one control point that regulates rates of fatty acid synthesis. However, the biochemical modulators that act on ACCase and the factors that in turn control these modulators are poorly understood. In addition, little is known about how the expression of genes involved in fatty acid synthesis is controlled. This review evaluates current knowledge of regulation of plant fatty metabolism and attempts to identify the major unanswered questions. PMID:15012259

Ohlrogge, John B.; Jaworski, Jan G.

1997-06-01

167

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.

168

Fatty acid-induced beta cell hypersensitivity to glucose. Increased phosphofructokinase activity and lowered glucose-6-phosphate content.  

PubMed Central

Diabetic states are characterized by a raised serum/islet level of long chain fatty acids and a lowered ED50 for glucose-induced insulin secretion. Prolonged culture (> 6 h) of islets with long chain fatty acids replicates the basal insulin hypersecretion. We examined this effect in rat islets cultured for 24 h with 0.25 mM oleate. Insulin secretion at 2.8 mM glucose was doubled in combination with a 60% lowered islet content of glucose-6-phosphate (G6P). Investigation of the lowered G6P showed: (a) increased glucose usage from 0.5 to 100 mM glucose with identical values measured by [2-3H]glucose and [5-3H]glucose, (c) indicating little glucose- 6-phosphatase activity, (b) unchanged low pentose phosphate shunt activity, (c) 50% increased phosphofructokinase (PFK) Vmax, (d) a normal ATP/ADP ratio, and (e) unchanged fructose 2,6 bisphosphate content. Triacsin C, an inhibitor of fatty acyl-CoA synthetase, prevented the increase in PFK activity and the lowered G6P content. These results suggest that long chain acyl-CoA mediates the rise in PFK activity, which in turn lowers the G6P level. We speculate that the inhibition of hexokinase by G6P is thus attenuated, thereby causing the basal insulin hypersecretion.

Liu, Y Q; Tornheim, K; Leahy, J L

1998-01-01

169

Identification of transforming activity of free fatty acid receptor 2 by retroviral expression screening.  

PubMed

Gallbladder cancer (GBC) is a highly fatal malignancy in humans. Genetic alterations in KRAS or TP53 as well as overexpression of ERBB2 have been shown to contribute to the development of certain types of GBC. However, many cases of GBC do not harbor such genetic changes, with other transforming events awaiting discovery. We here tried to identify novel cancer-promoting genes in GBC, with the use of a retroviral cDNA expression library. A retroviral cDNA expression library was constructed from a surgically resected clinical specimen of GBC, and was used to infect 3T3 fibroblasts in a focus formation assay. cDNA incorporated into the transformed foci was rescued by PCR. One such cDNA was found to encode free fatty acid receptor 2 (FFAR2), a G protein-coupled receptor for short-chain fatty acids. The oncogenic potential of FFAR2 was confirmed both in vitro with the focus formation assay and by evaluation of cell growth in soft agar as well as in vivo with a tumorigenicity assay in nude mice. The isolated FFAR2 cDNA had no sequence alterations, suggesting that upregulation of FFAR2 expression may contribute to malignant transformation. Indeed, all of quantitative RT-PCR, in situ hybridization, and immunohistochemical analyses showed that the amount of FFAR2 mRNA and its protein product was increased in digestive tract cancer specimens. Furthermore, short-chain fatty acids potentiated the mitogenic action of FFAR2 in 3T3 cells. Our data thus, for the first time, implicate FFAR2 in carcinogenesis of the digestive tract. PMID:19780758

Hatanaka, Hisashi; Tsukui, Mamiko; Takada, Shuji; Kurashina, Kentaro; Choi, Young Lim; Soda, Manabu; Yamashita, Yoshihiro; Haruta, Hidenori; Hamada, Toru; Ueno, Toshihide; Tamada, Kiichi; Hosoya, Yoshinori; Sata, Naohiro; Yasuda, Yoshikazu; Nagai, Hideo; Sugano, Kentaro; Mano, Hiroyuki

2009-09-04

170

Link between light and fatty acid synthesis: thioredoxin-linked reductive activation of plastidic acetyl-CoA carboxylase.  

PubMed

Fatty acid synthesis in chloroplasts is regulated by light. The synthesis of malonyl-CoA, which is catalyzed by acetyl-CoA carboxylase (ACCase) and is the first committed step, is modulated by light/dark. Plants have ACCase in plastids and the cytosol. To determine the possible involvement of a redox cascade in light/dark modulation of ACCase, the effect of DTT, a known reductant of S-S bonds, was examined in vitro for the partially purified ACCase from pea plant. Only the plastidic ACCase was activated by DTT. This enzyme was activated in vitro more efficiently by reduced thioredoxin, which is a transducer of redox potential during illumination, than by DTT alone. Chloroplast thioredoxin-f activated the enzyme more efficiently than thioredoxin-m. The ACCase also was activated by thioredoxin reduced enzymatically with NADPH and NADP-thioredoxin reductase. These findings suggest that the reduction of ACCase is needed for activation of the enzyme, and a redox potential generated by photosynthesis is involved in its activation through thioredoxin as for enzymes of the reductive pentose phosphate cycle. The catalytic activity of ACCase was maximum at pH 8 and 2-5 mM Mg2+, indicating that light-produced changes in stromal pH and Mg2+ concentration modulate ACCase activity. These results suggest that light directly modulates a regulatory site of plastidic prokaryotic form of ACCase via a signal transduction pathway of a redox cascade and indirectly modulates its catalytic activity via stromal pH and Mg2+ concentration. A redox cascade is likely to link between light and fatty acid synthesis, resulting in coordination of fatty acid synthesis with photosynthesis. PMID:9380765

Sasaki, Y; Kozaki, A; Hatano, M

1997-09-30

171

Link between light and fatty acid synthesis: Thioredoxin-linked reductive activation of plastidic acetyl-CoA carboxylase  

PubMed Central

Fatty acid synthesis in chloroplasts is regulated by light. The synthesis of malonyl-CoA, which is catalyzed by acetyl-CoA carboxylase (ACCase) and is the first committed step, is modulated by light/dark. Plants have ACCase in plastids and the cytosol. To determine the possible involvement of a redox cascade in light/dark modulation of ACCase, the effect of DTT, a known reductant of S-S bonds, was examined in vitro for the partially purified ACCase from pea plant. Only the plastidic ACCase was activated by DTT. This enzyme was activated in vitro more efficiently by reduced thioredoxin, which is a transducer of redox potential during illumination, than by DTT alone. Chloroplast thioredoxin-f activated the enzyme more efficiently than thioredoxin-m. The ACCase also was activated by thioredoxin reduced enzymatically with NADPH and NADP-thioredoxin reductase. These findings suggest that the reduction of ACCase is needed for activation of the enzyme, and a redox potential generated by photosynthesis is involved in its activation through thioredoxin as for enzymes of the reductive pentose phosphate cycle. The catalytic activity of ACCase was maximum at pH 8 and 2–5 mM Mg2+, indicating that light-produced changes in stromal pH and Mg2+ concentration modulate ACCase activity. These results suggest that light directly modulates a regulatory site of plastidic prokaryotic form of ACCase via a signal transduction pathway of a redox cascade and indirectly modulates its catalytic activity via stromal pH and Mg2+ concentration. A redox cascade is likely to link between light and fatty acid synthesis, resulting in coordination of fatty acid synthesis with photosynthesis.

Sasaki, Yukiko; Kozaki, Akiko; Hatano, Mika

1997-01-01

172

Role of ? -oxidation in inhibiting Lactobacillus leichmanii by fatty acids  

Microsoft Academic Search

The effect of saturated fatty acids from 6:0 to 16:0 and oleic acid onLactobacillus leichmanii ATCC 4797 growing in non-skim-milk media was determined. The inhibition by lauric acid was higher than that obtained with any other fatty acid. A mutant (MC12) resistant to the fatty acid inhibition with high ß-oxidation activity was also studied. A positive correlation between the ability

Martha S. Núńez de Kairúz; Guillermo Oliver; Aída A. Pesce de Ruiz Holgado; Ricardo N. Farías

1983-01-01

173

Conversion of Fatty Acids by Bacillus sphaericus Like Organisms  

Microsoft Academic Search

Bacillus sphaericus species are mesophilic round-spored organisms that readily utilize fatty acid-based surfactants during growth, but their\\u000a ability to modify fatty acids is unknown. Among 57 B. sphaericus-like strains tested for fatty acid transformation activity in Wallen fermentation (WF) medium, ten converted oleic acid to\\u000a a new product determined by gas chromatography – mass spectrometry (GC-MS) to be 10-ketostearic acid

Tsung Min Kuo; Lawrence K. Nakamura; Alan C. Lanser

2002-01-01

174

Suppression of plasma free fatty acids upregulates peroxisome proliferator-activated receptor (PPAR)   and   and PPAR coactivator 1  in human skeletal muscle, but not lipid regulatory genes  

Microsoft Academic Search

Fatty acids are an important ligand for peroxisome proliferator-activated receptor (PPAR) activation and transcriptional regulation of metabolic genes. To examine whether reduced plasma free fatty acid (FFA) availability affects the mRNA content of proteins involved in fuel metabolism in vivo, the skeletal muscle mRNA content of various transcription factors, transcriptional coactivators and genes encoding for lipid regulatory proteins were examined

M J Watt; R J Southgate; A G Holmes; M A Febbraio

2004-01-01

175

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.

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

2011-01-01

176

Delta 6-desaturase activity in liver microsomes of rats fed diets enriched with cholesterol and/or omega 3 fatty acids.  

PubMed Central

The effect of feeding semipurified diets enriched in linseed (rich in C18:3, omega 3 fatty acid) or fish (rich in C20:5, omega 3 and C22:6, omega 3 fatty acid) oil with and without cholesterol supplementation on the desaturation of linoleic acid (C18:2, omega 6) by rat liver microsomal fractions was investigated. Animals fed diets supplemented with beef tallow were used as equal-energy controls. Both linseed-oil and fish-oil diets, without added cholesterol, decrease conversion of C18:2, omega 6 fatty acid to gamma-linolenic acid (C18:3, omega 6). Reduction in delta 6-desaturation was significantly greater for animals fed the diet containing fish oil than with animals fed the linseed-oil diet. The major effect of cholesterol supplementation was to decrease the rate of desaturation of C18:2, omega 6, when fed in combination with the beef-tallow diet, whereas delta 6-desaturation was unaffected when cholesterol was fed along with diets high in omega 3 fatty acids (linseed oil or fish oil). The activity of the delta 6-desaturase in vitro is consistent with the fatty acid composition observed for the microsomal membranes on which this enzyme is localized. Dietary linseed oil and fish oil lowered the arachidonic (C20:4, omega 6) acid content of rat liver microsomes, with an accompanying increase in membrane eicosapentaenoic (C20:5, omega 3) and docosahexaenoic (C22:6, omega 3) acid content, in comparison with the group fed beef tallow. Inclusion of cholesterol into the beef-tallow or linseed-oil diets resulted in decreased membrane C20:4, omega 6-fatty-acid content, with concomitant increase in C18:2, omega 6-fatty-acid content. However, addition of cholesterol to the fish-oil diet did not alter the microsomal membrane content of C20:4, omega 6 fatty acid. Thus it is suggested that (1) the decrease in prostaglandin E2, thromboxane and prostacyclin levels generally observed after fish-oil consumption may be at least partly due to inhibition of C20:4, omega 6-fatty-acid synthesis from C18:2, omega 6 fatty acid; and (2) consumption of fish oil prevents the further decrease in C20:4, omega 6-fatty-acid levels by dietary cholesterol that is apparent when cholesterol is fed in combination with diets high in saturated fat or C18:3, omega 3 fatty acid.

Garg, M L; Sebokova, E; Thomson, A B; Clandinin, M T

1988-01-01

177

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

PubMed

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

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

2013-08-19

178

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

PubMed Central

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

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

2013-01-01

179

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.

2013-01-01

180

Partial separation of individual enzyme activities of an ACP-dependent fatty acid synthetase from barley chloroplasts  

Microsoft Academic Search

An acyl carrier protein (ACP) dependent fatty acid synthetase (fas) from barley chloroplast stroma was purified five-fold\\u000a by ammonium sulphate precipitation and gel filtration on Sephacryl S-300. The ?-ketoacyl-ACP reductase, ?-ketoacyl-ACP synthetase,\\u000a acetyl-CoA:ACP transacylase and malonyl-CoA:ACP transacylase activities were resolved on the Sephacryl S-300 column with apparent\\u000a molecular weights of respectively 125, 92, 82 and 41 kilodalton. The fas activity

Peter Bordier Hřj; Jřrn Dalgaard Mikkelsen

1982-01-01

181

Chemical composition and antioxidant activity of the essential oil and fatty acids of the flowers of Rhanterium adpressum.  

PubMed

The essential oil obtained by hydrodistillation of the flowers of Rhanterium adpressum Coss. & Durieu was analyzed using GC and GC-MS. The essential oil was very rich in monoterpene compounds. The major components identified were the monoterpene hydrocarbons: camphene (21.8%), myrcene (19.3%) and alpha-pinene (17.4%). Other compounds, including limonene, beta-pinene and terpinol-4-ol, were present in low content (4-6%). The composition of the fatty acids in the lipid extract obtained from the flowers was also investigated by GC and GC-MS. The main fatty acids identified were palmitic (47.4%), oleic (12.9%) and stearic acids (10.6%). The total phenolic contents and the antioxidant activities were also evaluated for both extracts. The total phenolic contents were determined using the Folin-Ciocalteu reagent and the antioxidant activities were measured using three different assays: DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activity, FRAP (ferric reducing antioxidant potential) and a molybdenum assay. As a result of these tests, the lipid extract exhibited the highest antioxidant activities in comparison with the essential oil extract. PMID:24079197

Hamia, Chahrazed; Gourine, Nadhir; Boussoussa, Hadjer; Saidi, Mokhtar; Gaydou, Emile M; Yousfi, Mohamed

2013-08-01

182

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

PubMed

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

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

2013-09-18

183

Fatty acid-induced NF-kappaB activation and insulin resistance in skeletal muscle are chain length dependent.  

PubMed

The saturated fatty acid (SFA) palmitate induces insulin resistance in cultured skeletal muscle cells, which may be related to NF-kappaB activation. The aim of this study was to evaluate whether other SFAs also exert these effects on skeletal muscle and whether these relate to chain length. Therefore, we incubated L6 and C(2)C(12) skeletal muscle cells with four different fatty acids, caprylate (C8:0), laurate (C12:0), palmitate (C16:0), and stearate (C18:0), to study effects on GLUT4 translocation, deoxyglucose uptake, and NF-kappaB activation. Incubation of L6 cells with the long-chain FAs C16:0 and C18:0 reduced insulin-stimulated GLUT4 translocation and deoxyglucose uptake, whereas L6 cells incubated with the medium-chain FAs C8:0 and C12:0 remained insulin sensitive. Besides increasing NF-kappaB DNA binding activity in both L6 and C(2)C(12) cells, C16:0 also induced NF-kappaB transcriptional activity. C18:0 showed comparable effects, whereas the SFAs with shorter chain lengths were not able to elevate NF-kappaB transcriptional activity. Collectively, these results demonstrate that SFA-induced NF-kappaB activation coincides with insulin resistance and depends on FA chain length. PMID:18957619

Hommelberg, Pascal P H; Plat, Jogchum; Langen, Ramon C J; Schols, Annemie M W J; Mensink, Ronald P

2008-10-28

184

Nitro-fatty acids: novel anti-inflammatory lipid mediators.  

PubMed

Nitro-fatty acids are formed and detected in human plasma, cell membranes, and tissue, modulating metabolic as well as inflammatory signaling pathways. Here we discuss the mechanisms of nitro-fatty acid formation as well as their key chemical and biochemical properties. The electrophilic properties of nitro-fatty acids to activate anti-inflammatory signaling pathways are discussed in detail. A critical issue is the influence of nitroarachidonic acid on prostaglandin endoperoxide H synthases, redirecting arachidonic acid metabolism and signaling. We also analyze in vivo data supporting nitro-fatty acids as promising pharmacological tools to prevent inflammatory diseases. PMID:24068188

Rubbo, H

2013-09-06

185

Lipophilization of somatostatin analog RC-160 with long chain fatty acid improves its antiproliferative and antiangiogenic activity in vitro.  

PubMed

The therapeutic potential of the somatostatin analogue RC-160 having antiproliferative activity, is limited by its short serum half life. To overcome this limitation, fatty acids namely butanoic acid and myristic acid were conjugated to the N-terminal residue of RC-160. The lipophilized derivatives of RC-160 were synthesized, purified by reverse phase HPLC and characterized by ES-mass spectroscopy. The antiproliferative activity of lipophilized derivatives of RC-160 on the growth of MIA-PaCa2 (human pancreatic carcinoma), DU145 (human prostate carcinoma), ECV304 (human umbilical chord endothelioma), as well as their antiangiogenic activity was evaluated in vitro. The relative stability of myristoyl-RC-160 towards degradation by proteases and serum was also determined. Myristoyl-RC-160 exhibited significantly higher antiproliferative efficacy than RC-160, on the above cell lines (P<0.01). Receptor binding assays, demonstrated that the affinity of RC-160 towards somatostatin receptors remains unaltered by myristoylation. Unlike RC-160, the myristoylated derivative was found to have significantly greater resistance to protease and serum degradation (P<0.01). Myristoyl-RC-160 exhibited significantly greater antiproliferative activity on ECV304, than RC-160 (P<0.01). Myristoyl RC-160 could also inhibit capillary tube formation more efficiently than RC-160 in a dose dependent manner, suggesting that it possessed enhanced antiangiogenic activity in vitro (P<0.001). Lipophilization of RC-160 with long chain fatty acids like myristic acid endows it with improved antiproliferative and antiangiogenic activity, stability and therapeutic index. British Journal of Pharmacology (2000) 109, 101 - 109 PMID:10694208

Dasgupta, P; Mukherjee, R

2000-01-01

186

Lipophilization of somatostatin analog RC-160 with long chain fatty acid improves its antiproliferative and antiangiogenic activity in vitro  

PubMed Central

The therapeutic potential of the somatostatin analogue RC-160 having antiproliferative activity, is limited by its short serum half life. To overcome this limitation, fatty acids namely butanoic acid and myristic acid were conjugated to the N-terminal residue of RC-160. The lipophilized derivatives of RC-160 were synthesized, purified by reverse phase HPLC and characterized by ES-mass spectroscopy. The antiproliferative activity of lipophilized derivatives of RC-160 on the growth of MIA-PaCa2 (human pancreatic carcinoma), DU145 (human prostate carcinoma), ECV304 (human umbilical chord endothelioma), as well as their antiangiogenic activity was evaluated in vitro. The relative stability of myristoyl-RC-160 towards degradation by proteases and serum was also determined. Myristoyl-RC-160 exhibited significantly higher antiproliferative efficacy than RC-160, on the above cell lines (P<0.01). Receptor binding assays, demonstrated that the affinity of RC-160 towards somatostatin receptors remains unaltered by myristoylation. Unlike RC-160, the myristoylated derivative was found to have significantly greater resistance to protease and serum degradation (P<0.01). Myristoyl-RC-160 exhibited significantly greater antiproliferative activity on ECV304, than RC-160 (P<0.01). Myristoyl RC-160 could also inhibit capillary tube formation more efficiently than RC-160 in a dose dependent manner, suggesting that it possessed enhanced antiangiogenic activity in vitro (P<0.001). Lipophilization of RC-160 with long chain fatty acids like myristic acid endows it with improved antiproliferative and antiangiogenic activity, stability and therapeutic index.

Dasgupta, P; Mukherjee, R

2000-01-01

187

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

188

Effect of ?-3 fatty acid supplementation on endothelial function, endogenous fibrinolysis and platelet activation in patients with a previous myocardial infarction: a randomised controlled trial  

PubMed Central

Objective The mechanisms through which ?-3 fatty acids reduce adverse cardiac events remain uncertain. We aimed to investigate the effect of ?-3 fatty acid supplementation on endothelial vasomotor function, endogenous fibrinolysis, and platelet and monocyte activation in patients with coronary heart disease. Design Randomised, double-blind, placebo-controlled, cross-over trial. Setting Academic cardiac centre. Participants 20 male patients with a previous myocardial infarction. Intervention ?-3 Fatty acid supplementation (2?g/day for 6?weeks) versus olive oil placebo. Outcome measures Peripheral blood was taken for analysis of platelet and monocyte activation, and forearm blood flow (FBF) was assessed in a subset of 12 patients during intrabrachial infusions of acetylcholine, substance P and sodium nitroprusside. Stimulated plasma tissue plasminogen activator (t-PA) concentrations were measured during substance P infusion. Results All vasodilators caused dose-dependent increases in FBF (p<0.0001). ?-3 Fatty acid supplementation did not affect endothelium-dependent vasodilation with acetylcholine and substance P compared with placebo (p=0.5 and 0.9). Substance P caused a dose-dependent increase in plasma t-PA concentrations (p<0.0001), which was not affected by ?-3 fatty acid supplementation (p=0.9). ?-3 Fatty acids did not affect platelet–monocyte aggregation, platelet P-selectin or CD40L, or monocyte CD40. Conclusions We have demonstrated that dietary supplementation with ?-3 fatty acids does not affect endothelial vasomotor function, endothelial t-PA release, or platelet and monocyte activation in patients with coronary heart disease. Cardiac benefits conferred by ?-3 fatty acids in coronary heart disease are unlikely to be mediated through effects on these systems.

Din, Jehangir N; Sarma, Jaydeep; Harding, Scott A; Lyall, Karin; Newby, David E; Flapan, Andrew D

2013-01-01

189

Adipocyte-type fatty acid-binding protein as inter-compartmental shuttle for peroxisome proliferator activated receptor ? agonists in cultured cell  

Microsoft Academic Search

We and others showed earlier that liver-type, epidermal-type and adipocyte-type (A-) fatty acid-binding proteins (FABPs) mediate peroxisome proliferator activated receptor (PPAR) dependent gene expression by channelling their ligand (fatty acid or drug) to the nuclear receptors via direct protein\\/protein interaction. To clarify mechanistic details of this signaling path, we address here A-FABP import into the nucleus and its interaction with

Anne Adida; Friedrich Spener

2006-01-01

190

The influence of the long chain fatty acid on the antagonistic activities of Rhizobium sin-1 lipid A  

PubMed Central

The lipid A from nitrogen-fixing bacterial species R. sin-1 is structurally unusual due to lack of phosphates and the presence of a 2-aminogluconolactone and a very long chain fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0), moiety. This structurally unusual lipid A can antagonize TNF-? production by human monocytes induced by E. coli LPS. To establish the relevance of the unusual long chain 27-hydroxyoctacosanoic acid for antagonistic properties, a highly convergent strategy for the synthesis of several derivatives of the lipid A of Rhizobium sin-1 has been developed. Compound 1 is a natural R. sin-1 lipid A having a 27-hydroxyoctacosanoic acid at C-2?, compound 2 contains an octacosanoic acid moiety at this position, and compound 3 is modified by a short chain tetradecanoic acid. Cellular activation studies with a human monocytic cell line have shown that the octacosanoic acid is important for optimal antagonistic properties. The hydroxyl of the natural 27-hydroxyoctacosanoic moiety does, however, not account for inhibitory activity. The resulting structure activity relationships are important for the design of compounds for the treatment of septic shock.

Zhang, Yanghui; Wolfert, Margreet A.; Boons, Geert-Jan

2007-01-01

191

Possible involvement of long chain fatty acids in the spores of Ganoderma lucidum (Reishi Houshi) to its anti-tumor activity.  

PubMed

During our isolation of biologically active substances from the spores of Ganoderma lucidum (Reishi Houshi, G. lucidum) guided by the inhibitory activity on HL-60 cell proliferation, NMR spectroscopic and mass spectrometric data indicate the substance contains a mixture of several long chain fatty acids. Hence, in this study, we have examined the inhibitory effects of an ethanolic extract of the spores of G. lucidum as the spore extract, on the proliferation of various human cancer cell lines by comparison with several authentic long chain fatty acids. Of the fatty acids we examined nonadecanoic acid (C19:0) showed the highest inhibitory activity for HL-60 cell proliferation with IC(50) values of 68+/-7 microM followed by heptadecanoic acid (C17:0, 120+/-23 microM), octa- (C18:0, 127+/-4 microM) and hexadecanoic acids (C16:0, 132+/-25 microM), respectively. The corresponding unsaturated fatty acids containing one double bond such as cis-10-nonadecenoic acid (C19:1), cis-9-octadecenoic acid (C18:1), cis-10-heptadecenoic acid (C17:1) and cis-9-hexadecenoic acid (C16:1) were less effective. The ethanolic extract of spores of G. lucidum were shown by annexin-V FITC/PI double staining to induce apoptosis of HL-60 cells in a similar way to cis-10-nonadecenoic acid (C19:1). These unsaturated fatty acids probably inhibit tumor necrosis factor production induced by lipopolysaccharide in a mouse macrophage preparation. Our results suggest the spores of G. lucidum contain 19-carbon fatty acids as one of the components for characteristics of its physiological effects. PMID:18827358

Fukuzawa, Masataka; Yamaguchi, Rie; Hide, Izumi; Chen, Zhiqing; Hirai, Yuko; Sugimoto, Akiko; Yasuhara, Tadashi; Nakata, Yoshihiro

2008-10-01

192

Metabolomics of Dietary Fatty Acid Restriction in Patients with Phenylketonuria  

PubMed Central

Background Patients with phenylketonuria (PKU) have to follow a lifelong phenylalanine restricted diet. This type of diet markedly reduces the intake of saturated and unsaturated fatty acids especially long chain polyunsaturated fatty acids (LC-PUFA). Long-chain saturated fatty acids are substrates of mitochondrial fatty acid oxidation for acetyl-CoA production. LC-PUFA are discussed to affect inflammatory and haemostaseological processes in health and disease. The influence of the long term PKU diet on fatty acid metabolism with a special focus on platelet eicosanoid metabolism has been investigated in the study presented here. Methodology/Principal Findings 12 children with PKU under good metabolic control and 8 healthy controls were included. Activated fatty acids (acylcarnitines C6–C18) in dried blood and the cholesterol metabolism in serum were analyzed by liquid chromatographic tandem mass spectrometry (LC-MS/MS). Fatty acid composition of plasma glycerophospholipids was determined by gas chromatography. LC-PUFA metabolites were analyzed in supernatants by LC-MS/MS before and after platelet activation and aggregation using a standardized protocol. Patients with PKU had significantly lower free carnitine and lower activated fatty acids in dried blood compared to controls. Phytosterols as marker of cholesterol (re-) absorption were not influenced by the dietary fatty acid restriction. Fatty acid composition in glycerophospholipids was comparable to that of healthy controls. However, patients with PKU showed significantly increased concentrations of y-linolenic acid (C18:3n-6) a precursor of arachidonic acid. In the PKU patients significantly higher platelet counts were observed. After activation with collagen platelet aggregation and thromboxane B2 and thromboxane B3 release did not differ from that of healthy controls. Conclusion/Significance Long-term dietary fatty acid restriction influenced the intermediates of mitochondrial beta-oxidation. No functional influence on unsaturated fatty acid metabolism and platelet aggregation in patients with PKU was detected.

Mutze, Ulrike; Beblo, Skadi; Kortz, Linda; Matthies, Claudia; Koletzko, Berthold; Bruegel, Mathias; Rohde, Carmen; Thiery, Joachim; Kiess, Wieland; Ceglarek, Uta

2012-01-01

193

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

194

Phosphorus-based fatty acid methyl esters.  

PubMed

With the aim of designing novel transformable fatty acid diesters, various strategies for introducing phosphorus arms to the fatty backbone have been examined. While lithiated phosphine reacts classically to brominated fatty esters to afford the mono-addition product, the synthesis of phosphorylated diesters was found to be difficult, a fact related to the bulkiness of fatty acids and phosphine reagents. A base-induced dehydrochlorination reaction using ArPCl2 and hydroxy-terminated fatty esters resulted in metastable diester for which hydrolytic cleavage undergo phosphine oxidation and expulsion of one fatty chain. Alternatively, ArPOCl2 alleviates this drawback and provides stable, phosphorylated fatty acid diesters. PMID:23845998

Katir, Nadia; El Kadib, Abdelkrim; Castel, Annie

2013-07-08

195

Enhancement of neutrophil-mediated killing of Plasmodium falciparum asexual blood forms by fatty acids: importance of fatty acid structure.  

PubMed Central

Effects of fatty acids on human neutrophil-mediated killing of Plasmodium falciparum asexual blood forms were investigated by using a quantitative radiometric assay. The results showed that the antiparasitic activity of neutrophils can be greatly increased (>threefold) by short-term treatment with fatty acids with 20 to 24 carbon atoms and at least three double bonds. In particular, the n-3 polyenoic fatty acids, eicosapentaenoic and docosahexaenoic acids, and the n-6 fatty acid, arachidonic acid, significantly enhanced neutrophil antiparasitic activity. This effect was >1.5-fold higher than that induced by an optical concentration of the known agonist cytokine tumor necrosis factor alpha (TNF-alpha). At suboptimal concentrations, the combination of arachidonic acid and TNF-alpha caused a synergistic increase in neutrophil-mediated parasite killing. The fatty acid-induced effect was independent of the availability of serum opsonins but dependent on the structure of the fatty acids. The length of the carbon chain, degree of unsaturation, and availability of a free carboxyl group were important determinants of fatty acid activity. The fatty acids which increased neutrophil-mediated killing primed the enhanced superoxide radical generation of neutrophils in response to P. falciparum as detected by chemiluminescence. Scavengers of oxygen radicals significantly reduced the fatty acid-enhanced parasite killing, but cyclooxygenase and lipoxygenase inhibitors had no effect. These findings have identified a new class of immunoenhancers that could be exploited to increase resistance against Plasmodium species.

Kumaratilake, L M; Ferrante, A; Robinson, B S; Jaeger, T; Poulos, A

1997-01-01

196

Fatty Acid Based Biodegradable Polymer  

Microsoft Academic Search

Synthetic polymers have become an indispensable part of the daily?life of human beings and the biodegradable class of polymers hold immense value in therapeutics. Fatty acid incorporation in biodegradable polymers renders flexibility, low melting point, hydrophobicity, and pliability properties. At the same time, degradation into naturally occurring compounds makes them environmentally friendly besides their utility in various applications like drug

Jay Prakash Jain; Marina Sokolsky; Neeraj Kumar; A. J. Domb

2008-01-01

197

REGULATION OF FATTY ACID SYNTHESIS  

Microsoft Academic Search

All plant cells produce fatty acids from acetyl-CoA by a common pathway localized in plastids. Although the biochemistry of this pathway is now well understood, much less is known about how plants control the very different amounts and types of lipids produced in different tissues. Thus, a central challenge for plant lipid research is to provide a molecular understanding of

John B. Ohlrogge; Jan G. Jaworski

1997-01-01

198

Oxidative stability of fatty acids  

Technology Transfer Automated Retrieval System (TEKTRAN)

The use of polyunsaturated fatty acids in poultry feeds follows the recent trend in the food industry to fortify processed foods with health promoting supplements. The chemical structure of these compounds presents a challenge to the feed formulator and producer that must contend with such unstable ...

199

The effects of trans fatty acids on fatty acyl ?5 desaturation by human skin fibroblasts  

Microsoft Academic Search

The effectiveness of different fatty acids as inhibitors of fatty acyl ?5 desaturation activity in human skin fibroblasts\\u000a has been investigated. When incubated with 2.25 ?M [14C] eicosatrienoate (20?3?6) in otherwise lipid-free medium, these cells rapidly incorporate the radiolabeled fatty acid into\\u000a cellular glycerolipids and desaturate it to produce both [14C] arachidonate and [14C] docosatetraenoate. The ?5 desaturation activity can

Miriam D. Rosenthal; Mark A. Doloresco

1984-01-01

200

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

2013-09-07

201

Plastid Metabolic Pathways for Fatty Acid Metabolism  

Microsoft Academic Search

Fatty acid metabolism is important for storage oil synthesis as well as membrane biogenesis in plant cells. In the past few\\u000a decades, attention has been paid to the pathways, mechanisms, regulation and genetic manipulation of fatty acid metabolism\\u000a in oil-accumulating tissues, because plant oil provides nutritious fatty acids and even renewable feedstock for industry.\\u000a The fatty acid synthesis in plant

Ikuo Nishida

202

Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides  

PubMed Central

Inspired by the anti-human immunodeficiency virus (HIV) activity of analogues of ?-galactosylceramide (GalCer), a set of mono- and di- saccharide fatty acid esters were designed as GalCer mimetics and their binding to the V3 loop peptide of HIV-1 and anti-HIV activity evaluated. 1,1-linked Gal-Man and Glu-Man disaccharides with an ester on the Man subunit bound the V3 loop peptide and inhibited HIV infectivity in single round infection assays with the TZM-bl cell line. IC50's were in the 50 ?M range with no toxicity to the cells at concentrations up to 200 ?M. These compounds appear to inhibit virus entry at early steps in viral infection since they were inactive if added post viral entry. Although these compounds were found to bind to the V3 loop peptide of gp120, it is not clear that this interaction is responsible for their anti-HIV activity because the relative binding affinity of closely related analogues did not correlate with their antiviral behavior. The low cytotoxicity of these 1,1-linked disaccharide fatty acid esters, combined with the easy accessibility to structurally diverse analogues make these molecules attractive leads for new topical anti-viral agents.

Bachan, Stewart; Fantini, Jacques; Joshi, AnJali; Garg, Himanshu; Mootoo, David R.

2011-01-01

203

Intake of fatty acids in Western Europe with emphasis on trans fatty acids: The TRANSFAIR study  

Microsoft Academic Search

Objective: To assess the intake of trans fatty acids (TFA) and other fatty acids in 14 Western European countries.Design and subjects: A maximum of 100 foods per country were sampled and centrally analysed. Each country calculated the intake of individual trans and other fatty acids, clusters of fatty acids and total fat in adults and\\/or the total population using the

K. F. A. M. Hulshof; MA van Erp-Baart; M. Antttolainen; W. Becker; S. M. Church; C. Couet; E Hermann-Kunz; H Kesteloot; T Leth; I Martins; O Moreiras; J Moschandreas; L Pizzoferrato; AH Rimestad; H Thorgeirsdottir; JMN van Amelsvoort; A Aro; AG Kafatos; D Lanzmann-Petithory; G van Poppel; KFAM Hulshof

1999-01-01

204

Manipulating Membrane Fatty Acid Compositions of Whole Plants with Tween-Fatty Acid Esters 1  

PubMed Central

This paper describes a method for manipulating plant membrane fatty acid compositions without altering growth temperature or other conditions. Tween-fatty acid esters carrying specific fatty acids were synthesized and applied to various organs of plants growing axenically in glass jars. Treated plants incorporated large amounts of exogenous fatty acids into all acylated membrane lipids detected. Fatty acids were taken up by both roots and leaves. Fatty acids applied to roots were found in leaves, while fatty acids applied to leaves appeared in both leaves higher on the plant and in roots, indicating translocation (probably in the phloem). Foliar application was most effective; up to 20% of membrane fatty acids of leaves above the treated leaf and up to 40% of root membrane fatty acids were exogenously derived. Plants which took up exogenous fatty acids changed their patterns of fatty acid synthesis such that ratios of saturated to unsaturated fatty acids remained essentially unaltered. Fatty acid uptake was most extensively studied in soybean (Glycine max [L.] Merr.), but was also observed in other species, including maize (Zea mays L.), mung beans (Vigna radiata L.), peas (Pisum sativum L.), petunia (Petunia hybrida L.) and tomato (Lycopersicon esculentum Mill.). Potential applications of this system include studying internal transport of fatty acids, regulation of fatty acid and membrane synthesis, and influences of membrane fatty acid composition on plant physiology. Images Figure 2

Terzaghi, William B.

1989-01-01

205

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

206

Fatty Acids Suppress Autophagic Turnover in ?-Cells*  

PubMed Central

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

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

2011-01-01

207

Trans Fatty Acids in Membranes: The Free Radical Path  

Microsoft Academic Search

The double bond geometry of most of the naturally occurring unsaturated fatty acid residues is cis. Due to the relevance of fatty acids as structural components of cell membranes and as biologically active molecules, the\\u000a change of the cis geometry means a change of the associated functions and activities. The finding that the cis to trans isomerization is effective in

Carla Ferreri; Maria Panagiotaki; Chryssostomos Chatgilialoglu

2007-01-01

208

Glucose Amplifies Fatty Acid-Induced Endoplasmic Reticulum Stress in Pancreatic ?-Cells via Activation of mTORC1  

PubMed Central

Background Palmitate is a potent inducer of endoplasmic reticulum (ER) stress in ?-cells. In type 2 diabetes, glucose amplifies fatty-acid toxicity for pancreatic ?-cells, leading to ?-cell dysfunction and death. Why glucose exacerbates ?-cell lipotoxicity is largely unknown. Glucose stimulates mTORC1, an important nutrient sensor involved in the regulation of cellular stress. Our study tested the hypothesis that glucose augments lipotoxicity by stimulating mTORC1 leading to increased ?-cell ER stress. Principal Findings We found that glucose amplifies palmitate-induced ER stress by increasing IRE1? protein levels and activating the JNK pathway, leading to increased ?-cell apoptosis. Moreover, glucose increased mTORC1 activity and its inhibition by rapamycin decreased ?-cell apoptosis under conditions of glucolipotoxicity. Inhibition of mTORC1 by rapamycin did not affect proinsulin and total protein synthesis in ?-cells incubated at high glucose with palmitate. However, it decreased IRE1? expression and signaling and inhibited JNK pathway activation. In TSC2-deficient mouse embryonic fibroblasts, in which mTORC1 is constitutively active, mTORC1 regulated the stimulation of JNK by ER stressors, but not in response to anisomycin, which activates JNK independent of ER stress. Finally, we found that JNK inhibition decreased ?-cell apoptosis under conditions of glucolipotoxicity. Conclusions/Significance Collectively, our findings suggest that mTORC1 mediates glucose amplification of lipotoxicity, acting through activation of ER stress and JNK. Thus, mTORC1 is an important transducer of ER stress in ?-cell glucolipotoxicity. Moreover, in stressed ?-cells mTORC1 inhibition decreases IRE1? protein expression and JNK activity without affecting ER protein load, suggesting that mTORC1 regulates the ?-cell stress response to glucose and fatty acids by modulating the synthesis and activity of specific proteins involved in the execution of the ER stress response. This novel paradigm may have important implications for understanding ?-cell failure in type 2 diabetes.

Bachar, Etti; Ariav, Yafa; Ketzinel-Gilad, Mali; Cerasi, Erol; Kaiser, Nurit; Leibowitz, Gil

2009-01-01

209

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.

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

2011-01-01

210

Polyhydric alcohol esters of ?-sulfo fatty acids  

Microsoft Academic Search

Direct esterification of ?-sulfopalmitic and ?-sulfostearic acids with excess ethylene glycol, glycerol, pentaerythritol and\\u000a 2-methoxyethanol was carried out in carbon tetrachloride to give products containing essentially monoesters. Surface active\\u000a properties of these compounds were measured with emphasis on washing ability in combination with soap. The detergency of these\\u000a esters was compared with those of hexitol and sucrose ?-sulfo fatty acid

T. Micich; M. Sucharski; J. K. Weil; A. J. Stirton

1972-01-01

211

Pyruvate dehydrogenase kinase 4 expression is synergistically induced by AMP-activated protein kinase and fatty acids  

Microsoft Academic Search

.  Organs are flexible as to which substrates they will use to maintain energy homeostasis. Under well-fed conditions, glucose\\u000a is a preferred substrate for oxidation. During fasting, fatty acid oxidation will become a more important energy source. Glucose\\u000a oxidation is decreased by fatty acids, a process in which the pyruvate dehydrogenase complex (PDH) and its regulator pyruvate\\u000a dehydrogenase kinase 4 (PDK4)

S. M. Houten; M. Chegary; H. te Brinke; W. J. Wijnen; J. F. C. Glatz; J. J. F. P. Luiken; F. A. Wijburg; R. J. A. Wanders

2009-01-01

212

Effect of carbohydrate fatty acid esters on Streptococcus sobrinus and glucosyltransferase activity.  

PubMed

Mutans streptococci are oral bacteria with a key role in the initiation of dental caries, because their glucosyltransferases synthesize polysaccharides from sucrose that allow them to colonize the tooth surface. Among the strategies to prevent dental caries that are being investigated are (1) the inhibition of bacterial growth of mutans streptococci or (2) the inhibition of glucosyltransferases involved in polysaccharide formation. Pure fatty acid esters of sucrose, maltose and maltotriose were synthesized by an enzyme-catalyzed process and tested as inhibitors of two glucosyltransferases of great homology, those from Streptococcus sobrinus and Leuconostoc mesenteroides NRRL B-512F. In spite of having their nonreducing end glucose blocked at 6-OH, they did not inhibit dextran synthesis. However, their effect on the growth of S. sobrinus in the solid and liquid phase was notable. 6-O-Lauroylsucrose, 6'-O-lauroylmaltose and 6"-O-lauroylmaltotriose at 100 microg/mL showed complete inhibition of S. sobrinus in agar plates. Consequently, these nontoxic derivatives are very promising for inclusion in oral-hygiene products aimed at disrupting plaque formation and preventing caries. PMID:15063188

Devulapalle, Kumari S; Gómez de Segura, Aranzazu; Ferrer, Manuel; Alcalde, Miguel; Mooser, Gregory; Plou, Francisco J

2004-04-28

213

New radiohalogenated alkenyl tellurium fatty acids  

SciTech Connect

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

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

1987-01-01

214

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

PubMed

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

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

2009-09-01

215

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

PubMed Central

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

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

2010-01-01

216

Activation of peroxisome proliferator-activated receptor-{delta} by GW501516 prevents fatty acid-induced nuclear factor-{kappa}B activation and insulin resistance in skeletal muscle cells.  

PubMed

Elevated plasma free fatty acids cause insulin resistance in skeletal muscle through the activation of a chronic inflammatory process. This process involves nuclear factor (NF)-kappaB activation as a result of diacylglycerol (DAG) accumulation and subsequent protein kinase Ctheta (PKCtheta) phosphorylation. At present, it is unknown whether peroxisome proliferator-activated receptor-delta (PPARdelta) activation prevents fatty acid-induced inflammation and insulin resistance in skeletal muscle cells. In C2C12 skeletal muscle cells, the PPARdelta agonist GW501516 prevented phosphorylation of insulin receptor substrate-1 at Ser(307) and the inhibition of insulin-stimulated Akt phosphorylation caused by exposure to the saturated fatty acid palmitate. This latter effect was reversed by the PPARdelta antagonist GSK0660. Treatment with the PPARdelta agonist enhanced the expression of two well known PPARdelta target genes involved in fatty acid oxidation, carnitine palmitoyltransferase-1 and pyruvate dehydrogenase kinase 4 and increased the phosphorylation of AMP-activated protein kinase, preventing the reduction in fatty acid oxidation caused by palmitate exposure. In agreement with these changes, GW501516 treatment reversed the increase in DAG and PKCtheta activation caused by palmitate. These effects were abolished in the presence of the carnitine palmitoyltransferase-1 inhibitor etomoxir, thereby indicating that increased fatty acid oxidation was involved in the changes observed. Consistent with these findings, PPARdelta activation by GW501516 blocked palmitate-induced NF-kappaB DNA-binding activity. Likewise, drug treatment inhibited the increase in IL-6 expression caused by palmitate in C2C12 and human skeletal muscle cells as well as the protein secretion of this cytokine. These findings indicate that PPARdelta attenuates fatty acid-induced NF-kappaB activation and the subsequent development of insulin resistance in skeletal muscle cells by reducing DAG accumulation. Our results point to PPARdelta activation as a pharmacological target to prevent insulin resistance. PMID:20185762

Coll, Teresa; Alvarez-Guardia, David; Barroso, Emma; Gómez-Foix, Anna Maria; Palomer, Xavier; Laguna, Juan C; Vázquez-Carrera, Manuel

2010-02-25

217

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; Řystein Fodstad; Finn Myhren; Marit L. Sandvold; Hans R. Hendriks; Godefridus J. Peters

2011-01-01

218

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

PubMed

Saccharomyces cerevisiae shows great potential for development of bioreactor systems geared toward 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 addition of an N-terminal epitope tag sequence (either Myc or hemagglutinin) to oleate desaturase (FAD2) or omega-3 linoleate desaturase (FAD3) enzymes from plants, which catalyze consecutive reactions in the production of long chain omega-3 fatty acids, significantly increases their activity up to fourfold when expressed in yeast cells. Quantitative protein blotting using an antibody specific for native FAD2 revealed that the steady-state amount of the epitope-tagged FAD2 protein was also approximately fourfold higher than that of its untagged counterpart, demonstrating a direct relationship between the epitope tag-induced increase in enzyme amount and fatty acid product formation. Protein half-life and RNA blotting experiments indicated that the half-lives and mRNA content of the tagged and untagged FAD2 proteins were essentially the same, suggesting that the epitope tags increased protein abundance by improving translational efficiency. Taken together, these results indicate that the addition of an epitope tag sequence to a plant fatty acid desaturase (FAD) not only provides a useful means for protein immunodetection using highly specific, commercially available antibodies, but that it also significantly increases FAD activity and the production of polyunsaturated fatty acids in yeast cells. PMID:19137289

O'Quin, Jami B; Mullen, Robert T; Dyer, John M

2009-01-10

219

Effect of maternal micronutrients (folic acid, vitamin B12) and omega 3 fatty acids on liver fatty acid desaturases and transport proteins in Wistar rats.  

PubMed

A disturbed fatty acid metabolism increases the risk of adult non-communicable diseases. This study examines the effect of maternal micronutrients on the fatty acid composition, desaturase activity, mRNA levels of fatty acid desaturases and transport proteins in the liver. Pregnant female rats were divided into 6 groups at 2 levels of folic acid both in the presence and absence of vitamin B(12). The vitamin B(12) deficient groups were supplemented with omega 3 fatty acid. An imbalance of maternal micronutrients reduces liver docosahexaenoic acid, increases ?5 desaturase activity but decreases mRNA levels, decreases ?6 desaturase activity but not mRNA levels as compared to control. mRNA level of ?5 desaturase reverts back to the levels of the control group as a result of omega 3 fatty acid supplementation. Our data for the first time indicates that maternal micronutrients differentially alter the activity and expression of fatty acid desaturases in the liver. PMID:22133376

Wadhwani, Nisha S; Manglekar, Rupali R; Dangat, Kamini D; Kulkarni, Asmita V; Joshi, Sadhana R

2011-11-30

220

CTRP1 Protein Enhances Fatty Acid Oxidation via AMP-activated Protein Kinase (AMPK) Activation and Acetyl-CoA Carboxylase (ACC) Inhibition*  

PubMed Central

We previously described the adipokine CTRP1, which has up-regulated expression following exposure to the anti-diabetic drug rosiglitazone and increased circulating levels in adiponectin-null mice (Wong, G. W., Krawczyk, S. A., Kitidis-Mitrokostas, C., Revett, T., Gimeno, R., and Lodish, H. F. (2008) Biochem. J. 416, 161–177). Although recombinant CTRP1 lowers blood glucose in mice, its physiological function, mechanisms of action, and roles in metabolic stress remain unknown. Here, we show that circulating levels of CTRP1 are strikingly reduced in diet-induced obese mice. Overexpressing CTRP1 in transgenic mice improved insulin sensitivity and decreased high-fat diet-induced weight gain. Reduced adiposity resulted from enhanced fatty acid oxidation and energy expenditure, effects mediated by AMP-activated protein kinase (AMPK). In skeletal muscle of transgenic mice, AMPK? and its downstream target, acetyl-CoA carboxylase (ACC), were hyperphosphorylated, indicative of AMPK activation and ACC inhibition. Inactivation of ACC promotes mitochondrial fat oxidation. Consistent with the direct effect of CTRP1 on AMPK signaling, recombinant CTRP1 administration acutely stimulated muscle AMPK? and ACC phosphorylation in vivo. In isolated soleus muscle, recombinant CTRP1 activated AMPK signaling to increase fatty acid oxidation ex vivo, an effect abrogated by an AMPK inhibitor. These results provide the first in vivo evidence that CTRP1 is a novel regulator of fatty acid metabolism.

Peterson, Jonathan M.; Aja, Susan; Wei, Zhikui; Wong, G. William

2012-01-01

221

Cardiac lipoprotein lipase activity in the hypertrophied heart may be regulated by fatty acid flux  

PubMed Central

Cardiac hypertrophy is characterised by an imbalance between lipid uptake and fatty acid ?-oxidation leading to an accumulation of lipids, particularly triacylglycerol (TAG). It is unclear whether uptake mechanisms such as lipoprotein lipase (LPL) can be attenuated to diminish this uptake. Rats were cold acclimated to induce cardiac hypertrophy and increase cardiac LPL. Lipid uptake and metabolism were altered by feeding a ‘Western-style’ high fat diet (WSD) or feeding oxfenicine (2 g/L) in the drinking water. Diastolic stiffness (increased volume change/unit pressure change) was induced in hypertrophied hearts for rats fed WSD (P < 0.05) or WSD + oxfenicine (P < 0.01), although absolute performance of cardiac muscle, estimated from stress–strain calculations was unchanged. Cold acclimation increased cardiac endothelial LPL (P < 0.05) but this was diminished following oxfenicine. Following WSD LPL was further decreased below WSD-fed control hearts (P < 0.05) with no further decrease by oxfenicine supplementation. A negative correlation was noted between plasma TAG and endothelial LPL (correlation coefficient = ? 0.654; P < 0.001) but not cardiac TAG concentration. Transcript levels of angiopoietin-like protein-4 (ANGPTL4) were increased 6-fold by WSD (P < 0.05) and increased 15-fold following WSD + oxfenicine (P < 0.001). For CA-hearts fed WSD or WSD + oxfenicine ANGPTL4 mRNA levels were preserved at chow-fed levels. VLDLR protein levels were increased 10-fold (P < 0.01) by CA. ANGPTL4 protein levels were increased 2-fold (P < 0.05) by WSD, but restored following oxfenicine. For CA-hearts WSD increased ANGPTL4 protein levels 3-fold (P < 0.01) with WSD + oxfenicine increasing ANGPTL4 protein 4-fold (P < 0.01). These data suggest that endothelial LPL levels in the heart are altered to maintain FA flux and may exploit ANGPTL4.

Hauton, David; Caldwell, Germaine M.

2012-01-01

222

New phenstatin-fatty acid conjugates: Synthesis and evaluation.  

PubMed

New phenstatin-fatty acid conjugates have been synthesized and tested against the KB-3-1, H460, MCF-7 and HEK293 cell lines, with an increase in anti-proliferative activity being observed at the micro-molar level paralleling an increase in un-saturation in the fatty acid component. PMID:23932339

Chen, Jinhui; Brown, David P; Wang, Yi-Jun; Chen, Zhe-Sheng

2013-07-24

223

A comparison of acyltransferase activities in vitro with the distribution of fatty acids in lecithins and triglycerides in vivo  

Microsoft Academic Search

The location and configuration of a double bond in a fatty acid influences the rate of its acyltransferase-catalyzed esterification\\u000a to form lecithin and its distribution in vivo between the primary and secondary positions of triglycerides and lecithins.\\u000a \\u000a Saturated acids of shorter chain length are transferred at rates similar to the long chain unsaturated acids.\\u000a \\u000a \\u000a The positional distributions of acids in

W. E. M. Lands; M. L. Blank; L. J. Nutter; O. S. Privett

1966-01-01

224

Changes in microsomal membrane phospholipids and fatty acids and in activities of membrane-bound enzyme in diabetic rat heart.  

PubMed

Diabetes mellitus is associated with alterations in lipid metabolism and cardiac dysfunction despite an absence of coronary arteriosclerotic changes. To investigate mechanisms of cardiac dysfunction in diabetic cardiomyopathy, we studied the relation between activities of membrane-bound enzymes and surrounding phospholipids in rats with diabetes induced with a single intravenous injection of streptozotocin (65 mg/kg). We found that total phospholipid content of sarcoplasmic reticulum membrane increased significantly 8 weeks after treatment with streptozotocin owing to increases in phosphatidylcholine and phosphatidylethanolamine, a decrease in arachidonic acid, and an increase in docosahexaenoic acid in the early stage of diabetes. Sarcolemmal Na+/K(+)-ATPase activity and the number of receptors decreased in isolated cardiomyocytes of diabetic rats 8 weeks after streptozotocin administration. The Ca2+ uptake of both sarcoplasmic reticulum and mitochondria decreased simultaneously in permeabilized, isolated cardiomyocytes from diabetic rats. The depression of membrane-bound enzyme activities was correlated with alterations in phospholipids, which are closely related to the microenvironment of membrane-bound enzymes and influence intracellular Ca2+ metabolism. Because these changes in phospholipids and fatty acids were reversible with insulin therapy, they are diabetes-specific and might be a cause of cardiac dysfunction in diabetes. PMID:9342428

Kuwahara, Y; Yanagishita, T; Konno, N; Katagiri, T

1997-08-01

225

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

226

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.

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

2013-01-01

227

Role of fatty acid-binding protein in cardiac fatty acid oxidation.  

PubMed

Although abundant in most biological tissues and chemically well characterized, the fatty acid-binding protein (FABP) was until recently in search of a function. Because of its strong affinity for long chain fatty acids and its cytoplasmic origin, this protein was repeatedly claimed in the literature to be the transcytoplasmic fatty acid carrier. However, techniques to visualize and quantify the movements of molecules in the cytoplasm are still in their infancy. Consequently the carrier function of FABP remains somewhat speculative. However, FABP binds not only fatty acids but also their CoA and carnitine derivatives, two typical molecules of mitochondrial origin. Moreover, it has been demonstrated and confirmed that FABP is not exclusively cytoplasmic, but also mitochondrial. A function for FABP in the mitochondrial metabolism of fatty acids plus CoA and carnitine derivatives would therefore be anticipated. Using spin-labelling techniques, we present here evidence that FABP is a powerful regulator of acylcarnitine flux entering the mitochondrial beta-oxidative system. In this perspective FABP appears to be an active link between the cytoplasm and the mitochondria, regulating the energy made available to the cell. This active participation of FABP is shown to be the consequence of its gradient-like distribution in the cardiac cell, and also of the coexistence of multispecies of this protein produced by self-aggregation. PMID:2266957

Fournier, N C; Richard, M A

228

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

PubMed Central

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

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

2012-01-01

229

Polyunsaturated fatty acids, inflammation, and immunity  

Microsoft Academic Search

The fatty acid composition of inflammatory and immune cells is sensitive to change according to the fatty acid composition\\u000a of the diet. In particular, the proportion of different types of polyunsaturated fatty acids (PUFA) in these cells is readily\\u000a changed, and this provides a link between dietary PUFA intake, inflammation, and immunity. The n?6 PUFA arachidonic acid (AA)\\u000a is the

Philip C. Calder

2001-01-01

230

Fatty Acid Biosynthesis and Regulation in Plants  

Microsoft Academic Search

\\u000a Fatty acids are aliphatic unbranched monocarboxylic acids that serve as the building blocks of membrane and storage lipids.\\u000a Plastids are the site for fatty acid biosynthesis with acetyl-CoA as its precursor. Carboxylation of acetyl-CoA is regulated\\u000a by covalent and allosteric modifications. Fatty acid synthase catalyzes repetitive series of reactions involving condensation,\\u000a reduction, dehydration, and second reduction. Acyl chain length is

R. Rajasekharan; V. Nachiappan

231

Peroxisome Proliferator-Activated Receptor-? in Capillary Endothelia Promotes Fatty Acid Uptake by Heart During Long-Term Fasting  

PubMed Central

Background Endothelium is a crucial blood–tissue interface controlling energy supply according to organ needs. We investigated whether peroxisome proliferator?activated receptor?? (PPAR?) induces expression of fatty acid–binding protein 4 (FABP4) and fatty acid translocase (FAT)/CD36 in capillary endothelial cells (ECs) to promote FA transport into the heart. Methods and Results Expression of FABP4 and CD36 was induced by the PPAR? agonist pioglitazone in human cardiac microvessel ECs (HCMECs), but not in human umbilical vein ECs. Real?time PCR and immunohistochemistry of the heart tissue of control (Ppargfl/null) mice showed an increase in expression of FABP4 and CD36 in capillary ECs by either pioglitazone treatment or 48 hours of fasting, and these effects were not found in mice deficient in endothelial PPAR? (Pparg?EC/null). Luciferase reporter constructs of the Fabp4 and CD36 promoters were markedly activated by pioglitazone in HCMECs through canonical PPAR?responsive elements. Activation of PPAR? facilitated FA uptake by HCMECs, which was partially inhibited by knockdown of either FABP4 or CD36. Uptake of an FA analogue, 125I?BMIPP, was significantly reduced in heart, red skeletal muscle, and adipose tissue in Pparg?EC/null mice as compared with Ppargfl/null mice after olive oil loading, whereas those values were comparable between Ppargfl/null and Pparg?EC/null null mice on standard chow and a high?fat diet. Furthermore, Pparg?EC/null mice displayed slower triglyceride clearance after olive oil loading. Conclusions These findings identified a novel role for capillary endothelial PPAR? as a regulator of FA handing in FA?metabolizing organs including the heart in the postprandial state after long?term fasting.

Goto, Kosaku; Iso, Tatsuya; Hanaoka, Hirofumi; Yamaguchi, Aiko; Suga, Toshihiro; Hattori, Akinari; Irie, Yasunori; Shinagawa, Yuji; Matsui, Hiroki; Syamsunarno, Mas Rizky A. A.; Matsui, Miki; Haque, Anwarul; Arai, Masashi; Kunimoto, Fumio; Yokoyama, Tomoyuki; Endo, Keigo; Gonzalez, Frank J.; Kurabayashi, Masahiko

2013-01-01

232

3,5-Diiodo-L-thyronine rapidly enhances mitochondrial fatty acid oxidation rate and thermogenesis in rat skeletal muscle: AMP-activated protein kinase involvement.  

PubMed

Triiodothyronine regulates energy metabolism and thermogenesis. Among triiodothyronine derivatives, 3,5-diiodo-l-thyronine (T(2)) has been shown to exert marked effects on energy metabolism by acting mainly at the mitochondrial level. Here we investigated the capacity of T(2) to affect both skeletal muscle mitochondrial substrate oxidation and thermogenesis within 1 h after its injection into hypothyroid rats. Administration of T(2) induced an increase in mitochondrial oxidation when palmitoyl-CoA (+104%), palmitoylcarnitine (+80%), or succinate (+30%) was used as substrate, but it had no effect when pyruvate was used. T(2) was able to 1) activate the AMPK-ACC-malonyl-CoA metabolic signaling pathway known to direct lipid partitioning toward oxidation and 2) increase the importing of fatty acids into the mitochondrion. These results suggest that T(2) stimulates mitochondrial fatty acid oxidation by activating several metabolic pathways, such as the fatty acid import/beta-oxidation cycle/FADH(2)-linked respiratory pathways, where fatty acids are imported. T(2) also enhanced skeletal muscle mitochondrial thermogenesis by activating pathways involved in the dissipation of the proton-motive force not associated with ATP synthesis ("proton leak"), the effect being dependent on the presence of free fatty acids inside mitochondria. We conclude that skeletal muscle is a target for T(2), and we propose that, by activating processes able to enhance mitochondrial fatty acid oxidation and thermogenesis, T(2) could play a role in protecting skeletal muscle against excessive intramyocellular lipid storage, possibly allowing it to avoid functional disorders. PMID:19116374

Lombardi, A; de Lange, P; Silvestri, E; Busiello, R A; Lanni, A; Goglia, F; Moreno, M

2008-12-30

233

Volatile fatty acids productivity by anaerobic co-digesting waste activated sludge and corn straw: Effect of feedstock proportion.  

PubMed

Volatile fatty acids (VFAs) are the most suitable and biodegradable carbon substrates for many bioprocesses. This study explored a new approach to improve the VFAs production from anaerobic co-digesting waste activated sludge (WAS) with corn straw (CS). The effect of feedstock proportion on the acidification efficiency was investigated. The maximum VFAs yield (corresponding fermentation time) was substantially increased 69% (96h), 45% (72h), 13% (120h) and 12% (120h) with 50%, 35%, 25% and 20% CS proportion of feedstock, respectively. HAc (acetic acid) was consistently the most abundant, followed by HPr (propionic acid) and n-HBu (butyric acid) in the co-digesting tests. The increase of CS in feedstock led to more production of HAc and HPr. Moreover, the consumption of protein and carbohydrate were also improved remarkably from 2955 and 249mg COD/L (individual WAS fermentation) to 6575 and 815mg COD/L (50%WAS:50%CS co-digestion) from 120 onward, respectively. The highest contribution of CS to additional VFAs production was1113mg VFAs (as COD)/g CS/L in the 65%WAS:35%CS co-digesting test. Our study indicated a valuable method to improve VFAs production from anaerobic co-digesting WAS and CS. PMID:23751505

Zhou, Aijuan; Guo, Zechong; Yang, Chunxue; Kong, Fanying; Liu, Wenzong; Wang, Aijie

2013-06-08

234

Waste activated sludge hydrolysis and short-chain fatty acids accumulation under mesophilic and thermophilic conditions: Effect of pH  

Microsoft Academic Search

The effect of pH (4.0–11.0) on waste activated sludge (WAS) hydrolysis and short-chain fatty acids (SCFAs) accumulation under mesophilic and thermophilic conditions were investigated. The WAS hydrolysis increased markedly in thermophilic fermentation compared to mesophilic fermentation at any pH investigated. The hydrolysis at alkaline pHs (8.0–11.0) was greater than that at acidic pHs, but both of the acidic and alkaline

Peng Zhang; Yinguang Chen; Qi Zhou

2009-01-01

235

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.

Carballeira, Nestor M.; Montano, Nashbly; Cintron, Gabriel A.; Marquez, Carmary; Rubio, Celia Fernandez; Prada, Christopher Fernandez; Balana-Fouce, Rafael

2010-01-01

236

Altered fatty acid desaturation and microsomal fatty acid composition in the streptozotocin diabetic rat  

Microsoft Academic Search

Streptozotocin diabetes in the rat diminishes the synthesis of both monounsaturated and polyunsaturated fatty acids. Rat liver\\u000a microsomal fatty acid composition and fatty acid desaturation were studied in the streptozotocin diabetic rat. The major alterations\\u000a in fatty acid composition found in the diabetic rat were decreased proportions of palmitoleic, oleic and arachidonic acids\\u000a and an increased proportion of linoleic and

Fred H. Faas; William J. Carter

1980-01-01

237

PPAR? Activation Rescues Pancreatic ?-Cell Line INS-1E from Palmitate-Induced Endoplasmic Reticulum Stress through Enhanced Fatty Acid Oxidation  

PubMed Central

One of the key factors responsible for the development of type 2 diabetes is the loss of functional pancreatic ? cells. This occurs due to a chronic exposure to a high fatty acid environment. ER stress is caused by an accumulation of irreversible misfold or unfold protein: these trigger the death of functional pancreatic ? cells. PPAR? is an orphan nuclear receptor. It plays a pivotal role in regulating the metabolism of dietary lipids and fats. However, the correlation between PPAR? of fatty acids and ER stress of pancreatic ? cells is not quite clear till date. Here, we show that PPAR? attenuates palmitate-induced ER stress of pancreatic ? cells. On the other hand, PPAR? agonist inhibits both abnormal changes in ER structure and activation of signaling cascade, which is downstream ER stress. Further, we illustrate that PPAR? attenuates palmitate-induced ER stress by promoting fatty acid oxidation through treatment with etomoxir, an inhibitor of fatty acid oxidation. It dramatically abolishes PPAR?-mediated inhibition of ER stress. Finally, we show that PPAR? could protect pancreatic ? cells from palmitate-induced cell death and dysfunction of insulin secretion. Our work elucidates the protective effect of PPAR? on the fatty-acid-induced toxicity of pancreatic ? cells.

Cao, Mingming; Tong, Yuzhen; Lv, Qingguo; Chen, Xiang; Long, Yang; Jiang, Li; Wan, Jun; Zhang, Yuwei; Zhang, Fang; Tong, Nanwei

2012-01-01

238

Virucidal activities of medium- and long-chain fatty alcohols, fatty acids and monoglycerides against herpes simplex virus types 1 and 2: comparison at different pH levels.  

PubMed

Previous studies have shown that certain lipids and fatty alcohols have microbicidal activities against a number of pathogens. In this study, virucidal activities of fatty alcohols and lipids were tested against HSV types 1 and 2 at various concentrations, times, and pH levels. The aim was first, to determine which compounds are most virucidal against HSV and could possibly be used as active ingredients in topical drug formulations and second, to attempt to throw light on the mode of action of virucidal lipids. Good agreement was found between the activities for HSV-1 and HSV-2. The activity of a compound depends on the concentration and time of contact and most of the compounds are more active at pH 4.2 than at pH 7. This information may be helpful in the formulation of pharmaceutical dosage forms for treatment of herpes lesions in skin and mucosa. The difference between the polar groups of alcohols and fatty acids, i.e. hydroxyl group versus carboxyl group, and the corresponding difference in their hydrophile-lipophile balance (HLB) may explain their different virucidal activities against HSV. However, in most cases HLB numbers cannot explain the different virucidal activities of fatty alcohols and lipids, particularly not their increased activity at low pH. It is more likely that the acidic environment makes HSV more sensitive, possibly by ionic changes in the envelope proteins. PMID:15676016

Hilmarsson, Hilmar; Kristmundsdóttir, Thórdís; Thormar, Halldor

2005-01-01

239

Regulation of hepatic gene expression by saturated fatty acids  

PubMed Central

Diets rich in saturated fatty acids have long been associated with increased plasma cholesterol concentrations and hence increased risk of cardiovascular disease. More recently, they have also been suggested to promote the development of non-alcoholic fatty liver disease. While there is now considerable evidence to suggest that polyunsaturated fatty acids exert many of their effects through regulating the activity of transcription factors, including peroxisome proliferator activated receptors, sterol regulatory binding proteins (SREBPs) and liver X receptor, our understanding of how saturated fatty acids act is still limited. Here we review the potential mechanisms whereby saturated fatty acids modulate hepatic lipid metabolism thereby impacting on the synthesis, storage and secretion of lipids. Evidence is presented that their effects are, at least partly, mediated through modulation of the activity of the SREBP family of transcription factors.

Vallim, T.; Salter, A.M.

2010-01-01

240

Do trans Fatty Acids Impair Linoleic Acid Metabolism in Children?  

Microsoft Academic Search

Trans isomeric fatty acids disturb themetabolism of essential polyunsaturated fatty acids in animals and in premature infants. We assessed whether similar effects may also occur in healthy children. Plasma phospholipid fatty acid composition was analysed in 53 apparently healthy children aged 1-15 years (mean 7.5 years). Trans fatty acids were found in all samples and contributed 1.78 ± 0.10% (w\\/w,

Tamĺs Decsi; Berthold Koletzko

1995-01-01

241

Polyunsaturated fatty acids and cardiovascular disease  

Microsoft Academic Search

Replacing saturated with polyunsaturated (PUFAs) rather than monounsaturated fatty acids or carbohydrates results in cardiovascular\\u000a prevention over a wide range of intakes. The mechanisms by which PUFAs reduce cardiovascular risk are manifold, and the extent\\u000a and precise nature of their activities is the subject of several investigations, spanning from in vitro mechanistic studies\\u000a to human intervention trials. This article reviews

Doriane Richard; Pedro Bausero; Charlotte Schneider; Francesco Visioli

2009-01-01

242

Parallel activation of mitochondrial oxidative metabolism with increased cardiac energy expenditure is not dependent on fatty acid oxidation in pigs  

PubMed Central

Steady state concentrations of ATP and ADP in vivo are similar at low and high cardiac workloads; however, the mechanisms that regulate the activation of substrate metabolism and oxidative phosphorylation that supports this stability are poorly understood. We tested the hypotheses that (1) there is parallel activation of mitochondrial and cytosolic dehydrogenases in the transition from low to high workload, which increases NADH/NAD+ ratio in both compartments, and (2) this response does not require an increase in fatty acid oxidation (FAO). Anaesthetized pigs were subjected to either sham treatment, or an abrupt increase in cardiac workload for 5 min with dobutamine infusion and aortic constriction. Myocardial oxygen consumption and FAO were increased 3- and 2-fold, respectively, but ATP and ADP concentrations did not change. NADH-generating pathways were rapidly activated in both the cytosol and mitochondria, as seen in a 40% depletion in glycogen stores, a 3.6-fold activation of pyruvate dehydrogenase, and a 50% increase in tissue NADH/NAD+. Simulations from a multicompartmental computational model of cardiac energy metabolism predicted that parallel activation of glycolysis and mitochondrial metabolism results in an increase in the NADH/NAD+ ratio in both cytosol and mitochondria. FAO was blocked by 75% in a third group of pigs, and a similar increase in and the NAHD/NAD+ ratio was observed. In conclusion, in the transition to a high cardiac workload there is rapid parallel activation of substrate oxidation that results in an increase in the NADH/NAD+ ratio.

Zhou, Lufang; Cabrera, Marco E; Huang, Hazel; Yuan, Celvie L; Monika, Duda K; Sharma, Naveen; Bian, Fang; Stanley, William C

2007-01-01

243

Effect of the degree of hydrogenation of dietary fish oil on the trans fatty acid content and enzymatic activity of rat hepatic microsomes.  

PubMed

The degree of fat hydrogenation and the trans fatty acid content of the diet affect the fatty acid composition of membranes, and the amount and the activity of some membrane enzymes. We describe the effects of four isocaloric diets containing either sunflower oil (SO, 0% trans), fish oil (FO, 0.5% trans), partially hydrogenated fish oil (PHFO, 30% trans), or highly hydrogenated fish oil (HHFO, 3.6% trans) as fat sources on the lipid composition and the trans fatty acid content of rat hepatic microsomes. We also describe the effect of these diets on the cytochrome P-450 content and on the aminopyrine N-demethylase, aniline hydroxylase, and UDP-glucuronyl transferase microsomal activities. Cytochrome P-450 content was dependent on the degree of unsaturation of the diet, being higher for the FO-containing diet and lower for the HHFO diet. Aminopyrine N-demethylase activity also correlated with the degree of unsaturation of the diet as did the cytochrome P-450 content did (FO > SO > PHFO > HHFO). Aniline hydroxylase activity appeared to be independent of the degree of unsaturation of the dietary fat, but correlated with the trans fatty acid content of the diet, which was also reflected in the trans content of the microsomal membranes. UDP-glucuronyl transferase activity was higher for the FO-containing diet than for the SO diet, showing intermediate values after the PHFO and HHFO diets. PMID:9688169

Morgado, N; Galleguillos, A; Sanhueza, J; Garrido, A; Nieto, S; Valenzuela, A

1998-07-01

244

?-3 fatty acids effect on wound healing  

PubMed Central

Physiological events in the initial inflammatory stage of cutaneous wound healing influence subsequent stages. Proinflammatory cytokines coordinate molecular and cellular processes during the inflammatory stage. Polyunsaturated fatty acids (PUFA) alter proinflammatory cytokine production, but how this phenomenon specifically influences wound healing is not clearly understood. In the present study, effects of marine-derived ?-3 eicosapentaenoic and docosahexaenoic PUFA on proinflammatory cytokines in wound serum and time to complete healing in healthy, human skin were evaluated. We compared plasma fatty acid levels in two groups (N=30) at baseline and after 4 weeks of eicosapentaenoic/ docosahexaenoic PUFA supplements (active) or placebo (control). Eight small blisters on participants’ forearms were created. Proinflammatory cytokines interleukin-1? (IL-1?), IL-6, and tumor necrosis factor-? were quantified in blister fluid at 5 and 24 hours after creation. Wound area was calculated daily. Eicosapentaenoic and docosahexaenoic plasma fatty acid levels were significantly higher in the active group. Additionally, we found significantly higher IL-1? levels in blister fluid in the active group and time to complete wound closure was somewhat longer. These results suggest that eicosapentaenoic and docosahexaenoic PUFA may increase proinflammatory cytokine production at wound sites and thus, depending on the clinical context, have noninvasive, therapeutic potential to affect cutaneous wound healing

McDaniel, Jodi C.; Belury, Martha; Ahijevych, Karen; Blakely, Wendy

2008-01-01

245

Metabolic aspects of trans fatty acids  

Microsoft Academic Search

The consumption of trans isomers of unsaturated fatty acids has been associated withuntoward metabolic effects. Several clinical investigations demonstrated that trans fatty acids increase plasma LDL-cholesterol and lipoprotein (a) and reduce HDL-cholesterol concentrations. These alterations of plasma lipid profiles indicate an atherogenic effect of trans fatty acids. Both in preterm infants and in healthy children aged 1–15 years, we found

B. Koletzko; T. Decsi

1997-01-01

246

Fatty acid content of selected seed oils.  

PubMed

Fatty acid content of selected seed oils from world-wide edible fruits, Ceratonia ciliqua (carob) from Caesalpiniaceae family, Diospyros kaki (persimmon) from Ebenaceae family, Zizyphus jujuba (jujube) from Rhamnaceae family, and Persea gratissima (avocado pear) from Lauraceae family, were determined by capillary gas chromatography- mass spectrometry (GC-MS) to find new natural sources for essential fatty acids. Among the seed oils analyzed, Ceratonia ciliqua has been found to have the highest essential fatty acid content. PMID:15277087

Orhan, Ilkay; Sener, Bilge

2002-01-01

247

Esterification of Fatty Acid by Zirconic Catalysts  

Microsoft Academic Search

Sulfated zirconia (SO4\\u000a 2?\\/ZrO2) was proved as an efficient catalyst for the esterification of fatty acids and alcohols, the alkyl esters of long chain fatty\\u000a acids are wildly used in industry and daily life. In this paper, the esterification of long chain fatty acid (both saturated\\u000a and unsaturated) with simple alcohol catalyzed by SZ catalyst was presented. It is found

Xiaoting Hu; Zheng Zhou; Defang Sun; Yuantao Wang; Zhibing Zhang

2009-01-01

248

Dietary fatty acids and insulin resistance  

Microsoft Academic Search

High-fat diets have been associated with insulin resistance, a risk factor for both Type II diabetes and heart disease. The\\u000a effect of dietary fat on insulin varies depending on the type of fatty acid consumed. Saturated fatty acids have been consistently\\u000a associated with insulin resistance. On the other hand, medium and long-chain fatty acid intakes are associated with insulin\\u000a sensitivity,

Jennifer C. Lovejoy

1999-01-01

249

Water-deficit impact on fatty acid and essential oil composition and antioxidant activities of cumin (Cuminum cyminum L.) aerial parts.  

PubMed

This study is designed to examine the effect of water deficit on growth, fatty acid and essential oil composition, and antioxidant activities of Cuminum cyminum aerial part extracts. Plants were treated with different levels of water deficit: control (C), moderate water deficit (MWD), and severe water deficit (SWD). Plant growth (height, fresh and dry matter weights) as well as yield components were significantly increased under moderate water deficit and conversely reduced at severe level. Total fatty acid content decreased significantly with severity of constraint. Drought reduced considerably the proportions of major fatty acids and the unsaturated to saturated fatty acid ratio. The essential oil yield was 0.14% (based on the dry weight); it increased by 2.21-fold at MWD but decreased by 42.8% under SWD in comparison to the control. Drought results in the modification of the essential oil chemotype from 1-phenyl-1-butanol to 1-phenyl-1,2-ethanediol. Antioxidant activities of the acetone extracts were determined by two complementary test systems, namely, DPPH and ?-carotene/linoleic acid. The highest activity was exhibited by moderately stressed plants and was reduced significantly under SWD. In control plants, the total phenolic amount was 10.23 mg GAE/g DW, which increased by 1.5-fold under MWD and decreased by 42% under SWD. PMID:21141890

Bettaieb, Iness; Knioua, Sana; Hamrouni, Ibtissem; Limam, Ferid; Marzouk, Brahim

2010-12-08

250

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

PubMed Central

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

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

2012-01-01

251

Polyunsaturated fatty acids regulate lipogenic and peroxisomal gene expression by independent mechanisms  

Microsoft Academic Search

Polyunsaturated fatty acids of the (n-6) and (n-3) families uniquely coordinate hepatic lipid synthesis and oxidation by suppressing the transcription of hepatic genes encoding lipogenic and glycolytic enzymes while concomitantly inducing the activity of enzymes in mitochondrial and peroxisomal fatty acid oxidation. Recently a group of fatty acid activated nuclear transcription factors termed peroxisome proliferator activated receptors (PPARs) were cloned.

S. D. Clarke; M. Turini; D. Jump

1997-01-01

252

Fatty acids for use as a medicament  

US Patent & Trademark Office Database

The invention relates to fatty acid stimulation of rectal mucosa initiating the process of defecation, acting as a laxative. Furthermore, the invention relates to the usage of free fatty acids, fatty acid mixtures and fatty acid extracts from marine lipids in pharmaceutical formulations such as suppositories, ointments, tablets and gelatin capsules for treatment and prevention of multiple disorders like constipation, hemorrhoids, bacterial infections (e.g. helicobacter pylori), viral infections (e.g. herpes simplex virus infections) and inflammations, as well as against fissura ani and pruritus ani.

Loftsson; Thorsteinn (Reykjavik, IS); Stefansson; Einar (Reykjavik, IS)

2013-02-12

253

Melittin Exerts Multiple Effects on the Release of Free Fatty Acids from L1210 Cells: Lack of Selective Activation of Phospholipase A 2 by Melittin  

Microsoft Academic Search

Melittin is known as a phospholipase A2 (PLA2) activator, but the selectivity of its effect on PLA2 is uncertain. We examined the selectivity of melittin effect on the release of free fatty acids (FFAs) from L1210 cells using various inhibitors. A systemic lipid analysis by HPLC and GLC revealed that melittin induced release of various FFAs including saturated, monounsaturated, and

Sang Yoon Lee; Heung Soon Park; Soo Jae Lee; Myung-Un Choi

2001-01-01

254

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...

255

AcetylCoA carboxylase and fatty acid synthase activity and immunodetectable protein in adipose tissues of ruminants: Effect of temperature and feeding level1,2  

Microsoft Academic Search

To gain insights into the regulation of fat synthesis, we have investigated the effect of cold environmental exposure and feed restriction of sheep on activity and immunodetectable protein content of acetyl-CoA carboxylase (ACC) and fatty acid synthase in adipose tissue. Subcutaneous and mesenteric adi- pose tissues were collected at slaughter from sheep ex- posed to either cold (0 ± 2°C)

J. A. Moibi; E. D. Ekpe; R. J. Christopherson

256

Early events in the perception of lipopolysaccharides in the brown alga Laminaria digitata include an oxidative burst and activation of fatty acid oxidation cascades  

Microsoft Academic Search

This study provides evidence that bacterial lipopoly- saccharides can be strong triggers of early events of defence reactions in the brown algal kelp Laminaria digitata, constituting the first report of a biological activity of this class of macromolecules in a marine alga. The early events include an oxidative burst, re- lease of free saturated and unsaturated fatty acids (FFAs) and

Frithjof C. Kupper; Emmanuel Gaquerel; Eva-Maria Boneberg; Siegfried Morath; Jean-Pierre Salaun; Philippe Potin

2006-01-01

257

?-Oxidation of ?-Chlorinated Fatty Acids  

PubMed Central

Myeloperoxidase-derived HOCl targets tissue- and lipoprotein-associated plasmalogens to generate ?-chlorinated fatty aldehydes, including 2-chlorohexadecanal. Under physiological conditions, 2-chlorohexadecanal is oxidized to 2-chlorohexadecanoic acid (2-ClHA). This study demonstrates the catabolism of 2-ClHA by ?-oxidation and subsequent ?-oxidation from the ?-end. Mass spectrometric analyses revealed that 2-ClHA is ?-oxidized in the presence of liver microsomes with initial ?-hydroxylation of 2-ClHA. Subsequent oxidation steps were examined in a human hepatocellular cell line (HepG2). Three different ?-chlorinated dicarboxylic acids, 2-chlorohexadecane-(1,16)-dioic acid, 2-chlorotetradecane-(1,14)-dioic acid, and 2-chloroadipic acid (2-ClAdA), were identified. Levels of 2-chlorohexadecane-(1,16)-dioic acid, 2-chlorotetradecane-(1,14)-dioic acid, and 2-ClAdA produced by HepG2 cells were dependent on the concentration of 2-ClHA and the incubation time. Synthetic stable isotope-labeled 2-ClHA was used to demonstrate a precursor-product relationship between 2-ClHA and the ?-chlorinated dicarboxylic acids. We also report the identification of endogenous 2-ClAdA in human and rat urine and elevations in stable isotope-labeled urinary 2-ClAdA in rats subjected to intraperitoneal administration of stable isotope-labeled 2-ClHA. Furthermore, urinary 2-ClAdA and plasma 2-ClHA levels are increased in LPS-treated rats. Taken together, these data show that 2-ClHA is ?-oxidized to generate ?-chlorinated dicarboxylic acids, which include ?-chloroadipic acid that is excreted in the urine.

Brahmbhatt, Viral V.; Albert, Carolyn J.; Anbukumar, Dhanalakshmi S.; Cunningham, Bryce A.; Neumann, William L.; Ford, David A.

2010-01-01

258

Ergosterol profiles, fatty acid composition, and antioxidant activities of button mushrooms as affected by tissue part and developmental stage.  

PubMed

This article investigated the mycochemical profiles and the antioxidant activities of the lipophilic extracts of the white and brown button mushrooms. We found that only free ergosterols were present in both mushrooms at 2.04-4.82 mg/g dry matter (DM). Ergosterol concentration was higher in early growth stages but decreased as the mushrooms grew, and it distributed evenly between the caps and stems during early developmental stages but accumulated more in the caps after maturation. The photochemiluminescence (PCL) values of the two mushrooms were 5.49-10.48 nmol trolox equivalent/mg DM, and the EC50 values of 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay ranged 20.19-41.49 mg DM/?g DPPH. The ergosterol content positively correlated with the antioxidant activities (r2>0.89). The total fatty acid content was 8.7 mg/g DM in the white and 5.1 mg/g DM in the brown button mushroom and contained mainly linoleic, palmitic, and stearic acids. Our data provide guidance for optimized harvesting time of mushrooms and maximized health benefits. PMID:20961043

Shao, Suqin; Hernandez, Marta; Kramer, John K G; Rinker, Danny L; Tsao, Rong

2010-10-20

259

Fatty acid metabolism in freshwater fish with particular reference to polyunsaturated fatty acids  

Microsoft Academic Search

Fatty acids in fish can arise from two sources: synthesis de novo from non?lipid carbon sources within the animal, or directly from dietary lipid. Acetyl?CoA derived mainly from protein can be converted to saturated fatty acids via the combined action of acetyl?CoA carboxylase and fatty acid synthetase. The actual rate of fatty acid synthesis de novo is inversely related to

R. J. Henderson

1996-01-01

260

Effects of medium-chain fatty acids and oleic acid on blood lipids, lipoproteins, glucose, insulin, and lipid transfer protein activities1-3  

Microsoft Academic Search

Background: Dietary medium-chain fatty acids (MCFAs) are of nutritional interest because they are more easily absorbed from di- etary medium-chain triacylglycerols (MCTs) than are long-chain fatty acids from, for example, vegetable oils. It has generally been claimed that MCFAs do not increase plasma cholesterol, although this claim is poorly documented. Objective: We compared the effects of a diet rich in

Tine Tholstrup; Christian Ehnholm; Matti Jauhiainen; Martin Petersen; Carl-Erik Hřy; Pia Lund; Brittmarie Sandström

261

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.

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

262

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.

Lands, Bill

2012-01-01

263

Oleuropein reduces free fatty acid-induced lipogenesis via lowered extracellular signal-regulated kinase activation in hepatocytes.  

PubMed

Oleuropein, a bitter glucoside found in green olive leaves, and its metabolite hydroxytyrosol display powerful antioxidant activity both in vivo and in vitro. In this study, we hypothesized that the antioxidant activity of oleuropein could attenuate hepatic steatosis. To test this hypothesis, we established steatotic hepatocytes using HepG2 and FL83B cells treated with free fatty acids (FFAs) (oleate:palmitate, 2:1). To confirm hepatic steatosis, the intracellular lipid levels were quantitatively measured by Nile Red staining, and the sizes and distributions of lipid droplets were visualized by transmission electron microscopy. The expression of PAT family proteins as well as of adipose differentiation-related protein and tail interacting protein (TIP47) was evaluated by reverse transcriptase polymerase chain reaction and immunoblotting. To examine the cellular and molecular events associated with oleuropein, annexin V/propidium iodide staining and immunoblotting were performed. Oleuropein decreased the number and size of lipid droplets in FFA-treated cells and reduced intracellular triglyceride accumulation. However, it did not affect the expression of lipid droplets-associated PAT family proteins, including adipose differentiation-related protein and TIP47. In addition, oleuropein reduced FFA-induced extracellular signal-regulated kinase activation but had no effect on c-Jun N-terminal kinase or AKT activation. Given its protective effects against FFA-induced hepatocellular steatosis, oleuropein may be a lipid-lowering agent. PMID:23146775

Hur, Wonhee; Kim, Sung Woo; Lee, Young Ki; Choi, Jung Eun; Hong, Sung Woo; Song, Myeong Jun; Bae, Si Hyun; Park, Taesun; Um, Soo-Jong; Yoon, Seung Kew

2012-08-09

264

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

PubMed

Incubation in 100 micromol/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 micromol/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 mmol/L KCl, and 100 micromol/L diazoxide. These amplified secretory responses were paralleled by significant increases in the phospholipase C (PLC) activation monitored by fractional increases in (3)H-inositol efflux from these same islets. Amplified PLC responses were also observed with the cholinergic agonist carbachol (50 micromol/L). No differences in the secretory responses to the protein kinase C activator phorbol 12-myristate 13-acetate (200 nmol/L) could be detected between control and FAF-BSA-pretreated rat islets. Mouse islets were also immune to the amplifying impact of this treatment protocol. These findings demonstrate that short-term incubation in FAF-BSA significantly augments the activation of PLC in rat islets by a number of agonists. This proximal event provides the impetus for the distal activation of protein kinase C. If applicable to human islets, this manipulation may provide a mechanism to enhance the secretory responses from islets destined for transplantation, thus improving their in vivo secretory capacity. PMID:18191063

Zawalich, Walter S; Zawalich, Kathleen C

2008-02-01

265

Enhanced Activation of Phospholipase C and Insulin Secretion from Islets Incubated in Fatty Acid-Free BSA  

PubMed Central

Incubation in 100 ?M fatty acid-free BSA (FAF-BSA) significantly amplifies insulin secretion from isolated, perifused rat islets. When compared to the responses of control islets incubated in 100 ?M RIA grade BSA insulin secretion rates were increased 2-3 fold when these islets were stimulated with 10 mM glucose alone or with the combination of 10 mM glucose, 15 mM KCl and 100 ?M diazoxide. These amplified secretory responses were paralleled by significant increases in the phospholipase C (PLC) activation monitored by fractional increases in 3H-inositol efflux from these same islets. Amplified PLC responses were also observed to the cholinergic agonist carbachol (50 ?M). No differences in the secretory responses to the protein kinase C activator phorbol 12-myristate 13-acetate (200 nM) could be detected between control and FAF-BSA pretreated rat islets. Mouse islets were also immune to the amplifying impact of this treatment protocol. These findings demonstrate that short-term incubation in FAF-BSA significantly augments the activation of PLC in rat islets by a number of agonists. This proximal event provides the impetus for the distal activation of PKC. If applicable to human islets, this manipulation may provide a mechanism to enhance the secretory responses from islets destined for transplantation, thus improving their in vivo secretory capacity.

Zawalich, Walter S.; Zawalich, Kathleen C.

2008-01-01

266

Fatty acid composition of Costa Rican foods including trans fatty acid content  

Microsoft Academic Search

To further understand the fatty acid–disease relationships in an epidemiologic context, detailed composition tables are required. The composition of the major saturated, monounsaturated, and polyunsaturated fatty acids that are most abundant in the diet, is available for numerous foods in many countries, but data on the content of individual fatty acids with relative low abundance are scarce. We conducted a

Ana Baylin; Xinia Siles; Amy Donovan-Palmer; Xinia Fernandez; Hannia Campos

2007-01-01

267

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

268

Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants  

Microsoft Academic Search

Phospholipid hydroperoxide glutathione peroxidase (GPx4) is the only antioxidant enzyme known to directly reduce phospholipid hydroperoxides within membranes and lipoproteins, acting in conjunction with ?-tocopherol to inhibit lipid peroxidation. Peroxidation of lipids has been implicated in a number of pathophysiological processes, including inflammation and atherogenesis. We investigated the relative positive and negative effects of specific polyunsaturated fatty acids (PUFAs) and

Alan A. Sneddon; Hsin-Chieh Wu; Andrew Farquharson; Ian Grant; John R. Arthur; Dino Rotondo; Sun-Nam Choe; Klaus W. J. Wahle

2003-01-01

269

International Union of Pharmacology. LXXI. Free Fatty Acid Receptors FFA1, -2, and -3: Pharmacology and Pathophysiological Functions  

Microsoft Academic Search

Identification of G protein-coupled re- ceptors that are activated by free fatty acids has led to considerable interest in their pharmacology and func- tion because of the wide range of normal physiology and disease states in which fatty acids have been im- plicated. Free fatty acid receptor (FFA) 1 is activated by medium- to long-chain fatty acids and is expressed

LEIGH A. STODDART; NICOLA J. SMITH; GRAEME MILLIGAN

2008-01-01

270

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...

271

Macrophage ?1 AMP-activated Protein Kinase (?1AMPK) Antagonizes Fatty Acid-induced Inflammation through SIRT1*  

PubMed Central

In this study, we aim to determine cellular mechanisms linking nutrient metabolism to the regulation of inflammation and insulin resistance. The nutrient sensors AMP-activated protein kinase (AMPK) and SIRT1 show striking similarities in nutrient sensing and regulation of metabolic pathways. We find that the expression, activity, and signaling of the major isoform ?1AMPK in adipose tissue and macrophages are substantially down-regulated by inflammatory stimuli and in nutrient-rich conditions, such as exposure to lipopolysaccharide (LPS), free fatty acids (FFAs), and diet-induced obesity. Activating AMPK signaling in macrophages by 5-aminoimidazole-4-carboxamide-1-?4-ribofuranoside or constitutively active ?1AMPK (CA-?1) significantly inhibits; although inhibiting ?1AMPK by short hairpin RNA knock-down or dominant-negative ?1AMPK (DN-?1) increases LPS- and FFA-induced tumor necrosis factor ? expression. Chromatin immunoprecipitation and luciferase reporter assays show that activation of AMPK by CA-?1 in macrophages significantly inhibits LPS- or FFA-induced NF-?B signaling. More importantly, in a macrophage-adipocyte co-culture system, we find that inactivation of macrophage AMPK signaling inhibits adipocyte insulin signaling and glucose uptake. Activation of AMPK by CA-?1 increases the SIRT1 activator NAD+ content and SIRT1 expression in macrophages. Furthermore, ?1AMPK activation mimics the effect of SIRT1 on deacetylating NF-?B, and the full capacity of AMPK to deacetylate NF-?B and inhibit its signaling requires SIRT1. In conclusion, AMPK negatively regulates lipid-induced inflammation, which acts through SIRT1, thereby contributing to the protection against obesity, inflammation, and insulin resistance. Our study defines a novel role for AMPK in bridging the signaling between nutrient metabolism and inflammation.

Yang, Zhenggang; Kahn, Barbara B.; Shi, Hang; Xue, Bing-zhong

2010-01-01

272

Desaturation of fatty acids in Trypanosoma cruzi  

SciTech Connect

Uptake and metabolism of saturated (16:0, 18:0) and unsaturated (18:1(n-9), 18:2(n-6), 18:3(n-3)) fatty acids by cultured epimastigotes of Trypanosoma cruzi were studied. Between 17.5 and 33.5% of the total radioactivity of (1-/sup 14/C)labeled fatty acids initially added to the culture medium was incorporated into the lipids of T. cruzi and mostly choline and ethanolamine phospholipids. As demonstrated by argentation thin layer chromatography, gas liquid chromatography and ozonolysis of the fatty acids synthesized, exogenous palmitic acid was elongated to stearic acid, and the latter was desaturated to oleic acid and 18:2 fatty acid. The 18:2 fatty acid was tentatively identified as linoleic acid with the first bond in the delta 9 position and the second bond toward the terminal methyl end. Exogenous stearic acid was also desaturated to oleic and 18:2 fatty acid, while oleic acid was only converted into 18:2. All of the saturated and unsaturated fatty acids investigated were also converted to a small extent (2-4%) into polyunsaturated fatty acids. No radioactive aldehyde methyl ester fragments of less than nine carbon atoms were detected after ozonolysis of any of the fatty acids studied. These results demonstrate the existence of delta 9 and either delta 12 or delta 15 desaturases, or both, in T. cruzi and suggest that delta 6 desaturase or other desaturases of the animal type are likely absent in cultured forms of this organism.

de Lema, M.G.; Aeberhard, E.E.

1986-11-01

273

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...

274

Essential Fatty Acids and Human Brain  

Microsoft Academic Search

3 Abstract- The human brain is nearly 60 percent fat. We've learned in recent years that fatty acids are among the most crucial molecules that determine your brain's integrity and ability to perform. Essential fatty acids (EFAs) are required for maintenance of optimal health but they can not synthesized by the body and must be obtained from dietary sources. Clinical

Chia-Yu Chang; Jen-Yin Chen

2009-01-01

275

Analysis of fatty acids in ecstasy tablets  

Microsoft Academic Search

Fatty acids are the basis of so-called stearates which are frequently used as lubricants in the production of ecstasy tablets. Being a product added at the initial tablet production step its composition does not change once the compression is performed. The analysis of fatty acids can therefore provide useful information for a drug intelligence purpose. In this context an appropriate

Ines Baer; Pierre Margot

2009-01-01

276

Nitro-Fatty acids: formation, redox signaling, and therapeutic potential.  

PubMed

Abstract Significance: Nitrated derivatives of unsaturated fatty acids (nitro-fatty acids) are being formed and detected in human plasma, cell membranes, and tissue, triggering signaling cascades via covalent and reversible post-translational modifications of susceptible nucleophilic amino acids in transcriptional regulatory proteins and enzymes. Recent Advances: Nitro-fatty acids modulate metabolic as well as inflammatory signaling pathways, including the p65 subunit of nuclear factor ?B and the transcription factor peroxisome proliferator-activated receptor-?. Moreover, nitro-fatty acids can activate heat shock as well as phase II antioxidant responses. As electrophiles, they also activate the Nuclear factor erythroid 2-related factor 2 pathway. Critical Issues: We first discuss the mechanisms of nitro-fatty acid formation as well as their key chemical and biochemical properties, including their capacity to release nitric oxide and exert antioxidant actions. The electrophilic properties of nitro-fatty acids to activate anti-inflammatory signaling pathways are discussed in detail. A critical issue is the influence of nitroarachidonic acid on prostaglandin endoperoxide H synthases, modulating inflammatory processes through redirection of arachidonic acid metabolism and signaling. Future Directions: Based on this information, we analyze in vivo data supporting nitro-fatty acids as promising pharmacological tools to prevent inflammatory diseases associated with oxidative and nitrative stress conditions. A key future issue is to evaluate whether nitro-fatty acid supplementation would be useful for human diseases linked to inflammation as well as their potential toxicity when administered by long periods of time. Antioxid. Redox Signal. 19, 1257-1265. PMID:23256873

Trostchansky, Andrés; Bonilla, Lucía; González-Perilli, Lucía; Rubbo, Homero

2012-12-20

277

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

PubMed

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

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

2013-01-12

278

21 CFR 172.859 - Sucrose fatty acid esters.  

Code of Federal Regulations, 2010 CFR

... 3 2009-04-01 2009-04-01 false Sucrose fatty acid esters. 172.859 Section 172...CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified in this...

2009-04-01

279

21 CFR 172.859 - Sucrose fatty acid esters.  

Code of Federal Regulations, 2010 CFR

... 3 2010-01-01 2009-04-01 true Sucrose fatty acid esters. 172.859 Section 172...CONSUMPTION Multipurpose Additives § 172.859 Sucrose fatty acid esters. Sucrose fatty acid esters identified in this...

2010-01-01

280

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

Code of Federal Regulations, 2013 CFR

...2013-07-01 false Acetylated fatty acid glycerides (generic). 721.10520 Section...721.10520 Acetylated fatty acid glycerides (generic). (a) Chemical substance...generically as acetylated fatty acid glycerides (PMN P-11-160) is...

2013-07-01

281

Wax Esters of Vegetable Oil Fatty Acids Useful as Lubricants.  

National Technical Information Service (NTIS)

Wax esters are prepared entirely from acids obtained from hydrogenated vegetable oils. Fatty alcohols, prepared by hydrogenolysis of the fatty acids, are esterified with the fatty acids to yield the wax esters. These esters have properties similar to thos...

E. W. Bell

1978-01-01

282

Modification of fatty acid composition of lipid accumulating yeasts with cyclopropene fatty acid desaturase inhibitors  

Microsoft Academic Search

The effect of cyclopropene fatty acids, sterculic and malvalic, on the lipids of yeasts grown under nitrogen limiting, lipid accumulating, conditions was studied. The ratio of stearic to oleic acid showed a dose response effect, with an increase in stearic acid content as the dose of cyclopropene fatty acid increased, and a corresponding reduction in oleic acid. Linoleic and linolenic

R. S. Moreton

1985-01-01

283

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

284

Biosynthesis, degradation, and pharmacological importance of the fatty acid amides  

PubMed Central

The identification of two biologically active fatty acid amides, N-arachidonoylethanolamine (anandamide) and oleamide, has generated a great deal of excitement and stimulated considerable research. However, anandamide and oleamide are merely the best-known and best-understood members of a much larger family of biologically-occurring fatty acid amides. In this review, we will outline which fatty acid amides have been isolated from mammalian sources, detail what is known about how these molecules are made and degraded in vivo, and highlight their potential for the development of novel therapeutics.

Farrell, Emma K.; Merkler, David J.

2008-01-01

285

Oxidized LDL activates phospholipase A2 to supply fatty acids required for cholesterol esterification  

Microsoft Academic Search

We examined the roles of phospholipase A 2 (PLA 2 ) in oxidized LDL (oxLDL)-induced cholesteryl ester forma- tion in macrophages. In ( 3 H)oleic acid-labeled RAW264.7 cells and mouse peritoneal macrophages, oxLDL induced ( 3 H)cholesteryl oleate formation with an increase in free ( 3 H)oleic acid and a decrease in ( 3 H)phosphatidylcholine. The changes in these lipids

Satoshi Akiba; Yukimasa Yoneda; Satoshi Ohno; Megumi Nemoto; Takashi Sato

2003-01-01

286

An intronic peroxisome proliferator-activated receptor-binding sequence mediates fatty acid induction of the human carnitine palmitoyltransferase 1A.  

PubMed

The liver plays a central role in the response to fasting. The hormonal profile in this condition, low insulin, and high concentrations of glucagon in plasma, induce the release of large amounts of fatty acids from adipose tissue. Prolonged starvation can therefore induce a dramatic change in the fatty acid oxidative capacity of liver metabolism. Modulation of gene expression by PPARalpha plays a crucial role in this response. While a major role for PPARalpha in the liver is to produce ketone bodies as fuel through beta-oxidation for peripheral tissues during fast, its participation in the control of CPT1A, the rate-limiting step of the pathway, remains controversial. Using Web-based software (VISTA) combining transcription factor binding site database searches with comparative sequence analyses, we have localized a conserved functional PPAR responsive element downstream of the transcriptional start site of the human CPT1A gene. We have shown that this sequence is fundamental for fatty acids or PGC1-induced transcriptional activation of the CPT1A gene. These results corroborate the hypothesis that PPARalpha regulates the limiting step in the oxidation of fatty acids in liver mitochondria. PMID:16271724

Napal, Laura; Marrero, Pedro F; Haro, Diego

2005-10-21

287

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

2012-10-02

288

Essential fatty acids in visual and brain development.  

PubMed

Essential fatty acids are structural components of all tissues and are indispensable for cell membrane synthesis; the brain, retina and other neural tissues are particularly rich in long-chain polyunsaturated fatty acids (LC-PUFA). These fatty acids serve as specific precursors for eicosanoids, which regulate numerous cell and organ functions. Recent human studies support the essential nature of n-3 fatty acids in addition to the well-established role of n-6 essential fatty acids in humans, particularly in early life. The main findings are that light sensitivity of retinal rod photoreceptors is significantly reduced in newborns with n-3 fatty acid deficiency, and that docosahexaenoic acid (DHA) significantly enhances visual acuity maturation and cognitive functions. DHA is a conditionally essential nutrient for adequate neurodevelopment in humans. Comprehensive clinical studies have shown that dietary supplementation with marine oil or single-cell oil sources of LC-PUFA results in increased blood levels of DHA and arachidonic acid, as well as an associated improvement in visual function in formula-fed infants matching that of human breast-fed infants. The effect is mediated not only by the known effects on membrane biophysical properties, neurotransmitter content, and the corresponding electrophysiological correlates but also by a modulating gene expression of the developing retina and brain. Intracellular fatty acids or their metabolites regulate transcriptional activation of gene expression during adipocyte differentiation and retinal and nervous system development. Regulation of gene expression by LC-PUFA occurs at the transcriptional level and may be mediated by nuclear transcription factors activated by fatty acids. These nuclear receptors are part of the family of steroid hormone receptors. DHA also has significant effects on photoreceptor membranes and neurotransmitters involved in the signal transduction process; rhodopsin activation, rod and cone development, neuronal dendritic connectivity, and functional maturation of the central nervous system. PMID:11724460

Uauy, R; Hoffman, D R; Peirano, P; Birch, D G; Birch, E E

2001-09-01

289

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.

Penugonda, Kavitha; Lindshield, Brian L.

2013-01-01

290

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.

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

2006-01-01

291

Endurance training has little effect on active muscle free fatty acid, lipoprotein cholesterol, or triglyceride net balances  

Microsoft Academic Search

ABSTRACT We evaluated the hypothesis that net leg total free fatty acid (FFA), LDL cholesterol (LDL-C), and triglyceride (TG) uptake and HDL cholesterol (HDL-C) release during moderate ,intensity cycling exercise would ,be increased following endurance training. Eight sedentary men (26 ± 1 yr, 77.4 ± 3.7 kg) were studied in the postprandial state during 90 min of rest and 60

Kevin. A. Jacobs; Jill A. Fattor; Michael A. Horning; Anne L. Friedlander; Todd A. Hagobian; Eugene E. Wolfel; George A. Brooks

2006-01-01

292

Link between Light and Fatty Acid Synthesis: Thioredoxin-Linked Reductive Activation of Plastidic AcetylCoA Carboxylase  

Microsoft Academic Search

Fatty acid synthesis in chloroplasts is regulated by light. The synthesis of malonyl-CoA, which is catalyzed by acetyl-CoA carboxylase (ACCase) and is the first committed step, is modulated by light\\/dark. Plants have ACCase in plastids and the cytosol. To determine the possible involvement of a redox cascade in light\\/dark modulation of ACCase, the effect of DTT, a known reductant of

Yukiko Sasaki; Akiko Kozaki; Mika Hatano

1997-01-01

293

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

294

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.

Frostegard, A.; Tunlid, A.; Baath, E.

1993-01-01

295

Long chain omega-3 fatty acids: micronutrients in disguise.  

PubMed

Considerable information has accumulated to show that DHA and EPA have unique roles that differ from other n-3 fatty acids and the n-6 fatty acids, with increasing understanding of the mechanisms through which these fatty acids reduce risk of disease. DHA and EPA regulate hepatic lipid and glucose metabolism, but are present in foods of animal origin, which are generally high in protein with variable triglycerides and low carbohydrate. Biological activity at intakes too low to provide significant amounts of energy is consistent with the definition of a vitamin for which needs are modified by life-stage, diet and genetic variables, and disease. Recent studies reveal that DHA may play a central role in co-coordinating complex networks that integrate hepatic glucose, fatty acid and amino acid metabolism for the purpose of efficient utilization of dietary protein, particularly during early development when the milk diet provides large amounts of energy from fat. PMID:22709913

Innis, S M; Novak, E M; Keller, B O

2012-06-17

296

Hypotonic shocks activate rat TRPV4 in yeast in the absence of polyunsaturated fatty acids  

Microsoft Academic Search

Transient-receptor-potential channels (TRPs) underlie the sensing of chemicals, heat, and mechanical force. We expressed the rat TRPV1 and TRPV4 subtypes in yeast and monitored their activities in vivo as Ca2+ rise using transgenic aequorin. Heat and capsaicin activate TRPV1 but not TRPV4 in yeast. Hypotonic shocks activate TRPV4 but not TRPV1. Osmotic swelling is modeled to activate enzyme(s), producing polyunsaturated

Stephen H. Loukin; Zhenwei Su; Ching Kung

2009-01-01

297

Hepatic mitochondrial dysfunction induced by fatty acids and ethanol.  

PubMed

Understanding the key aspects of the pathogenesis of alcoholic fatty liver disease particularly alterations to mitochondrial function remains to be resolved. The role of fatty acids in this regard requires further investigation due to their involvement in fatty liver disease and obesity. This study aimed to characterize the early effects of saturated and unsaturated fatty acids alone on liver mitochondrial function and during concomitant ethanol exposure using isolated liver mitochondria and VA-13 cells (Hep G2 cells that efficiently express alcohol dehydrogenase). Liver mitochondria or VA-13 cells were treated with increasing concentrations of palmitic or arachidonic acid (1 to 160 ?M) for 24 h with or without 100 mM ethanol. The results showed that in isolated liver mitochondria both palmitic and arachidonic acids significantly reduced state 3 respiration in a concentration-dependent manner (P<0.001), implicating their ionophoric activities. Increased ROS production occurred in a dose-dependent manner especially in the presence of rotenone (complex I inhibitor), which was significantly more prominent in arachidonic acid at 80 ?M (+970%, P<0.001) than palmitic acid (+40%, P<0.01). In VA-13 cells, ethanol alone and both fatty acids (40 ?M) were able to decrease the mitochondrial membrane potential and cellular ATP levels and increase lipid formation. ROS production was significantly increased with arachidonic acid (+110%, P<0.001) exhibiting a greater effect than palmitic acid (+39%, P<0.05). While in the presence of ethanol, the drop in the mitochondrial membrane potential, cellular ATP levels, and increased lipid formation were further enhanced by both fatty acids, but with greater effect in the case of arachidonic acid, which also correlated with significant cytotoxicity (P<0.001). This study confirms the ability of fatty acids to promote mitochondrial injury in the development of alcoholic fatty liver disease. PMID:23010494

Gyamfi, Daniel; Everitt, Hannah E; Tewfik, Ihab; Clemens, Dahn L; Patel, Vinood B

2012-09-23

298

Methyl esters in the fatty acid industry  

Microsoft Academic Search

Methyl esters, derived from natural fats or oils, can be used as alternatives to fatty acids in the production of a number\\u000a of derivatives. The derivatives that can be made from methyl esters include fatty alkanolamides, fatty alcohols, isopropyl\\u000a esters, and sucrose polyesters. By using methyl esters as the raw materials, several benefits may be realized, such as, the\\u000a ability

R. D. Farris

1979-01-01

299

Effect of the degree of hydrogenation of fish oil on the enzymatic activity and on the fatty acid composition of hepatic microsomes from young and aged rats.  

PubMed

By modifying the degree of hydrogenation of dietary fat, it is possible to modify the fatty acid composition and the biochemical activity of cellular tissues. The age can be another variable influencing these modifications. The effect of isocaloric diets containing oils with different degrees of hydrogenation: fish oil (FO, 0.3% TRANS), partially hydrogenated fish oil (PHFO, 29% TRANS), or highly hydrogenated fish oil (HHFO, 2.3% TRANS), in the fatty acid composition (CIS and TRANS isomers) of hepatic microsomes from young (70-day-old) and aged (18-month-old) rats, in the microsomal cytochrome P-450 (C-450) content, and in the aminopyrine N-demethylase (AND), aniline hydroxylase (AH), NADPH cytochrome P-450 reductase (NCR), UDP-glucuronyl transferase (UGT), and GSH-S transferase (GST) enzymatic activities were studied. Fatty acid composition and n-6/n-3 ratio of microsomal membranes was modified to a higher extent in young rats. C-450 content and AND activity were reduced when the degree of hydrogenation of dietary fat was increased in the young and the aged rats. AH activity was higher after the PHFO diet in the young rats only. NCR activity was reduced in the young animals when the hydrogenation of the fat was increased. However, in aged rats the enzyme exhibited a higher activity after the PHFO and HHFO diet. UGT and GST activities where not affected by the level of hydrogenation of the dietary fat in both the young and the aged rats. However, UGT activity was higher in the young rats, while GST activity was higher in the aged animals. We conclude that hydrogenation of dietary fat can modify the fatty acid composition of hepatic microsomes, young animals being more sensitive to these changes than aged animals. These effects were also reflected in the amount and/or the activity of some molecular components of the hepatic microsomal mixed-function oxidase enzyme system. Microsomal TRANS fatty acid composition is not affecting the activity of the enzymes, the age of the animals being the most important factor. PMID:12743463

Morgado, Nora; Sanhueza, Julio; Nieto, Susana; Valenzuela, Alfonso

2003-01-01

300

Carbon flux and fatty acid synthesis in plants.  

PubMed

The de novo synthesis of fatty acids in plants occurs in the plastids through the activity of fatty acid synthetase. The synthesis of the malonyl-coenzyme A that is required for acyl-chain elongation requires the import of metabolites from the cytosol and their subsequent metabolism. Early studies had implicated acetate as the carbon source for plastidial fatty acid synthesis but more recent experiments have provided data that argue against this. A range of cytosolic metabolites including glucose 6-phosphate, malate, phosphoenolpyruvate and pyruvate support high rates of fatty acid synthesis by isolated plastids, the relative utilisation of which depends upon the plant species and the organ from which the plastids are isolated. The import of these metabolites occurs via specific transporters on the plastid envelope and recent advances in the understanding of the role of these transporters are discussed. Chloroplasts are able to generate the reducing power and ATP required for fatty acid synthesis by capture of light energy in the reactions of photosynthetic electron transport. Regulation of chloroplast fatty acid synthesis is mediated by the response of acetyl-CoA carboxylase to the redox state of the plastid, which ensures that the carbon metabolism is linked to the energy status. The regulation of fatty acid synthesis in plastids of heterotrophic cells is much less well understood and is of particular interest in the tissues that accumulate large amounts of the storage oil, triacylglycerol. In these heterotrophic cells the plastids import ATP and oxidise imported carbon sources to produce the required reducing power. The sequencing of the genome of Arabidopsis thaliana has now enabled a number of aspects of plant fatty acid synthesis to be re-addressed, particularly those areas in which in vitro biochemical analysis had provided equivocal answers. Examples of such aspects and future opportunities for our understanding of plant fatty acid synthesis are presented and discussed. PMID:11755683

Rawsthorne, Stephen

2002-03-01

301

Regulation of adipocyte gene expression by polyunsaturated fatty acids  

Microsoft Academic Search

A wide number of adipocyte genes are regulated by exogenous polyunsaturated fatty acids (PUFA) through the actions of the peroxisome proliferator activated receptor. Such genes include the adipocyte lipid-binding protein (ALBP or aP2) which plays a central role in facilitating the trafficking of fatty acids within adipocytes. Work from a number of laboratories has suggested the key elements of the

Ann Vogel Hertzel; David A. Bernlohr

1998-01-01

302

Fatty Acid Synthesis from Lactate in Growing Cattle1  

Microsoft Academic Search

Rates of fatty acid synthesis from láclateand acetate and activ ities of selected lipogenic and NADPH-generating enzymes were determined in subcutaneous, intermuscular and intramuscular adipose tissues of cattle that were 11-19 months of age. Fatty acid synthesis from lactate and acetate in creased from 11 to 13 months of age in subcutaneous and intermuscular adipose tissues; synthesis from lactate increased

GARNETT B. WHITEHURST; DONALD C. BEITZ; DANILO CIANZIO; ANDDAVID G. TOPEL

2010-01-01

303

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

Genevičve Martin; Kristina Schoonjans; Bart Staels; Johan Auwerx

1998-01-01

304

Oxylipins: Structurally diverse metabolites from fatty acid oxidation  

Microsoft Academic Search

Oxylipins are lipophilic signaling molecules derived from the oxidation of polyunsaturated fatty acids. Initial fatty acid oxidation occurs mainly by the enzymatic or chemical formation of fatty acid hydroperoxides. An array of alternative reactions further converting fatty acid hydroperoxides gives rise to a multitude of oxylipin classes, many with reported signaling functions in plants. Oxylipins include the phytohormone, jasmonic acid,

Alina Mosblech; Ivo Feussner; Ingo Heilmann

2009-01-01

305

Seasonal Variations in Fatty Acid Composition and the N-6\\/N-3 Fatty Acid Ratio of Pikeperch (Sander LUCIOPERCA) Muscle Lipids  

Microsoft Academic Search

Total lipid, fatty acid composition and the N-6\\/N-3 fatty acid ratios of muscle of pikeperch (Sander lucioperca) was determined once every two months. The ratio of unsaturated fatty acids (UFA) was higher than half of the total fatty acid content, and the monounsaturated fatty acid (MUFA) was higher than the polyunsaturated fatty acid (PUFA) ratio. The n-3 fatty acids were

Kazim Uysal; M. Yasar Aksoylar

2005-01-01

306

Bacterial sphingophospholipids containing non-hydroxy fatty acid activate murine macrophages via Toll-like receptor 4 and stimulate bacterial clearance.  

PubMed

Sphingobacterium spiritivorum has five unusual sphingophospholipids (SPLs). Our previous study determined the complete chemical structures of these SPLs. The compositions of the long-chain bases/fatty acids in the ceramide portion, isoheptadecasphingosine/isopentadecanoate or isoheptadecasphingosine/2-hydroxy isopentadecanoate, are characteristic. The immune response against bacterial lipid components is considered to play important roles in microbial infections. It is reported that several bacterial sphingolipids composed of ceramide are recognized by CD1-restricted T and NKT cells and that a non-peptide antigen is recognized by ?? T cells. In this study, we demonstrated that these bacterial SPLs activated murine bone marrow macrophages (BMMs) via Toll-like receptor (TLR) 4 but not TLR2, although they slightly activated CD1d-restricted NKT and ??T cells. Interestingly, this TLR 4-recognition pathway of bacterial SPLs involves the fatty acid composition of ceramide in addition to the sugar moiety. A non-hydroxy fatty acid composed of ceramide was necessary to activate murine BMMs. The bacterial survival was significantly higher in TLR4-KO mice than in TLR2-KO and wild-type mice. The results indicate that activation of the TLR4-dependent pathway of BMMs by SPLs induced an innate immune response and contributed to bacterial clearance. PMID:23545566

Fujiwara, Nagatoshi; Porcelli, Steven A; Naka, Takashi; Yano, Ikuya; Maeda, Shinji; Kuwata, Hirotaka; Akira, Shizuo; Uematsu, Satoshi; Takii, Takemasa; Ogura, Hisashi; Kobayashi, Kazuo

2013-03-29

307

Ferritin couples iron and fatty acid metabolism  

PubMed Central

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

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

2012-01-01

308

Effect of tanniniferous Terminalia chebula extract on rumen biohydrogenation, ?(9)-desaturase activity, CLA content and fatty acid composition in longissimus dorsi muscle of kids.  

PubMed

Conjugated linoleic acid, a fatty acid found in milk fat and ruminant meat is one of the functional food components. Modifying fatty acid composition so as to increase CLA and other beneficial PUFA/MUFA level and reducing SFA levels might be a key to enhance the neutraceutical and therapeutic value of ruminant-derived food products. In the present experiment, the effect of supplementation of polyphenol rich Terminalia chebula plant extract at different concentrations (1.06g/kg and 3.18g/kg of body weight in T1 and T2 groups, respectively) was investigated on fatty acid composition of rumen fluid, plasma, intramuscular fat and ?9-desaturase activity in longissimus dorsi muscle of crossbred kids. Total MUFA and PUFA content in muscle were enhanced by 25 and 35%, respectively, whereas SFA was reduced by 20% thereby improving the desaturation index. ?9-desaturase activity also increased by 47% resulting in an enhancement of total CLA content (58.73%) in muscle. PMID:22019314

Rana, Madhu Suman; Tyagi, A; Hossain, Sk Asraf; Tyagi, A K

2011-09-25

309

Dietary enhancement of selected fatty acid biosynthesis in the digestive gland of Mytilus galloprovincialis Lmk.  

PubMed

The fatty acid composition of the digestive gland from the mussel Mytilus galloprovincialis subjected to three different dietary regimens for 30 days was analyzed. Samples were collected at the beginning and end of the trial to obtain a comprehensive picture of fatty acid dynamics. Group A was unfed; group B received a diet consisting of 100% Thalassiosira weissflogii and, thus, similar to natural food; and group C received a diet consisting of 100% wheat germ conferring a 18:2?-6 abundance. Results indicate that fatty acid composition of lipid and phospholipid classes was affected by dietary treatments. However, adult mussel homeostatic skills minimized effects, and thus, only wheat germ diet deeply modified the fatty acid composition. Furthermore, in group C, the occurrence of the non-methylene-interrupted trienoic fatty acids was indicative of de novo fatty acid synthesis presumably because of active fatty acid elongation and ?5 desaturation system, also supported by the general ?-3 polyunsaturated fatty acid decrease. PMID:23298257

Ventrella, Vittoria; Pagliarani, Alessandra; Nesci, Salvatore; Trombetti, Fabiana; Pirini, Maurizio

2013-01-18

310

Enhancement of lipase catalyzed-fatty acid methyl esters production from waste activated bleaching earth by nullification of lipase inhibitors.  

PubMed

This study sought to identify inhibitory factors of lipase catalyzed-fatty acid methyl esters (FAME) production from waste activated bleaching earth (wABE). During the vegetable oil refinery process, activated bleaching earth (ABE) is used for removing the impure compounds, but adsorbs vegetable oil up to 35-40% as on a weight basis, and then the wABE is discarded as waste material. The impurities were extracted from the wABE with methanol and evaluated by infra-red (IR) spectroscopy, which revealed that some were chlorophyll-plant pigments. The chlorophylls inhibited the lipase during FAME conversion from wABE. The inhibition by a mixture of chlorophyll a and b was found to be competitive. The inhibition of the enzymatic hydrolysis of waste vegetable oil contained in wABE by chlorophyll a alone was competitive, while the inhibition by chlorophyll b alone was non-competitive. Furthermore, the addition of a small amount of alkali nullified this inhibitory effect and accelerated the FAME production rate. When 0.9% KOH (w/w wABE) was added to the transesterification reaction with only 0.05% lipase (w/w wABE), the maximum FAME production rate improved 120-fold, as compared to that without the addition of KOH. The alkali-combined lipase significantly enhanced the FAME production rate from wABE, in spite of the presence of the plant pigments, and even when a lower amount of lipase was used as a catalyst. PMID:19726181

Dwiarti, Lies; Ali, Ehsan; Park, Enoch Y

2009-09-01

311

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.

2012-01-01

312

Free fatty acid fractions from some vegetable oils exhibit reduced survival time-shortening activity in stroke-prone spontaneously hypertensive rats  

Microsoft Academic Search

Previously, we demonstrated that several vegetable oils that included low-erucic rapeseed oil markedly shortened the survival\\u000a time (by ?40%) of stroke-prone spontaneously hypertensive (SHRSP) rats as compared with perilla oil, soybean oil, and fish\\u000a oil. We considered that a factor other than fatty acids is toxic to SHRSP rats, because the survival time-shortening activity\\u000a could not be accounted for by

Makoto Miyazaki; Min-Zhao Huang; Naoya Takemura; Shiro Watanabe; Harumi Okuyama

1998-01-01

313

The Coactivator PGC1 Cooperates with Peroxisome Proliferator-Activated Receptor a in Transcriptional Control of Nuclear Genes Encoding Mitochondrial Fatty Acid Oxidation Enzymes  

Microsoft Academic Search

Peroxisome proliferator-activated receptor a (PPARa) plays a key role in the transcriptional control of genes encoding mitochondrial fatty acid b-oxidation (FAO) enzymes. In this study we sought to determine whether the recently identified PPAR gamma coactivator 1 (PGC-1) is capable of coactivating PPARa in the transcriptional control of genes encoding FAO enzymes. Mammalian cell cotransfection experiments demon- strated that PGC-1

RICK B. VEGA; JANICE M. HUSS; DANIEL P. KELLY

314

The Coactivator PGC1 Cooperates with Peroxisome Proliferator-Activated Receptor alpha in Transcriptional Control of Nuclear Genes Encoding Mitochondrial Fatty Acid Oxidation Enzymes  

Microsoft Academic Search

Peroxisome proliferator-activated receptor a (PPARa) plays a key role in the transcriptional control of genes encoding mitochondrial fatty acid b-oxidation (FAO) enzymes. In this study we sought to determine whether the recently identified PPAR gamma coactivator 1 (PGC-1) is capable of coactivating PPARa in the transcriptional control of genes encoding FAO enzymes. Mammalian cell cotransfection experiments demon- strated that PGC-1

RICK B. VEGA; JANICE M. HUSS; DANIEL P. KELLY

2000-01-01

315

Oil-water interfacial activation of lipase for interesterification of triglyceride and fatty acid  

Microsoft Academic Search

Lipase usually has little interesterification activity in organic solvents, probably owing to the absence of an oil-water\\u000a interface. Lipases were processed in a two-phase hydrocarbon-water system that had an oil-water interface. Crude lipase (from\\u000a Rhizopus japonicus) in a buffer and a small volume of aliphatic hydrocarbon as an oil phase were mixed and then lyophilized to remove the aqueous\\u000a and

Tatsuo Maruyama; Mitsutoshi Nakajima; Sosaku Uchikawa; Hiroshi Nabetani; Shintaro Furusaki; Minoru Seki

2000-01-01

316

Activation of PPAR-? in isolated rat skeletal muscle switches fuel preference from glucose to fatty acids  

Microsoft Academic Search

Aims\\/hypothesis  GW501516, an agonist of peroxisome proliferator-activated receptor-? (PPAR-?), increases lipid combustion and exerts antidiabetic action in animals, effects which are attributed mainly to direct effects on skeletal muscle. We explored such actions further in isolated rat skeletal muscle.Materials and methods  Specimens of rat skeletal muscle were pretreated with GW501516 (0.01–30 ?mol\\/l) for 0.5, 4 or 24 h and rates of fuel metabolism were

B. Brunmair; K. Staniek; J. Dörig; Z. Szöcs; K. Stadlbauer; V. Marian; F. Gras; C. Anderwald; H. Nohl; W. Waldhäusl; C. Fürnsinn

2006-01-01

317

Plasma fatty acid profile and alternative nutrition.  

PubMed

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 larger study of health and nutritional status of children in Slovakia. Alternative nutrition groups had significantly lower values of saturated fatty acids. The content of oleic acid was identical to omnivores. A significant increase was observed for linoleic and alpha-linolenic (n-3) acids. The dihomo-gamma-linolenic (n-6) acid and arachidonic (n-6) acid values were comparable to omnivores for all alternative nutrition groups. Values of n-3 polyunsaturated fatty acids in lactoovovegetarians were identical to those of omnivores whereas they were significantly increased in semivegetarians consuming fish twice a week. Due to the total exclusion of animal fats from the diet, vegans had significantly reduced values of palmitoleic acid as well as eicosapentaenoic (n-3) acid and docosahexaenoic (n-3) acid resulting in an increased n-6/n-3 ratio. Values of plasma fatty acids found in alternative nutrition groups can be explained by the higher intake of common vegetable oils (high content of linoleic acid), oils rich in alpha-linolenic acid (cereal germs, soybean oil, walnuts), as well as in n-3 polyunsaturated fatty acids (fish). The results of fatty acids (except n-3 in vegans) and other lipid parameters confirm the beneficial effect of vegetarian nutrition in the prevention of cardiovascular diseases. PMID:9491192

Krajcovicová-Kudlácková, M; Simoncic, R; Béderová, A; Klvanová, J

1997-01-01

318

trans fatty acids. 4. Effects on fatty acid composition of colostrum and milk  

Microsoft Academic Search

trans Isometric fatty acids of partially hydrogenated fish oil (PHFO) consist oftrans 20?1 andtrans 22?1 in addition to thetrans isomers of 18?1, which are abundant in hydrogenated vegetable oils, such as in partially hydrogenated soybean oil (PHSBO).\\u000a The effects of dietarytrans fatty acids in PHFO and PHSBO on the fatty acid composition of milk were studied at 0 (colostrum) and

Jan Pettersen; Johannes Opstvedt

1991-01-01

319

Determination of Fatty Acid Composition and Total Trans Fatty Acids in Cereal-Based Turkish Foods  

Microsoft Academic Search

The fatty acid composition and trans fatty acids of 13 cereal-based foods produced by Turkish companies were analysed by capillary gas-liquid chromatography. The total fat contents of the samples ranged from 1.8 to 37.9%. Traditional Turkish white bread and bulgur had the lowest fat content (1.8% and 2.3% respectively) and wafer the highest (37.9%). The major fatty acids in the

320

Plasma lipids and fatty acid synthase activity are regulated by short-chain fructo-oligosaccharides in sucrose-fed insulin-resistant rats.  

PubMed

The aim of this study was to evaluate the chronic effects of a short-chain fructo-oligosaccharide (FOS)-containing diet on plasma lipids and the activity of fatty acid synthase (FAS) in insulin-resistant rats. Normal male Sprague-Dawley rats, 5 wk old, were randomly assigned to two groups and fed either a sucrose-rich diet (S, 575 g sucrose /kg diet and 140 g lipids/kg diet) or a sucrose-rich diet supplemented with 10 g/100 g short-chain fructo-oligosaccharides (S/FOS). A third reference group (R) was fed a standard nonpurified diet (g/kg, 575 g starch, 50 g fat). After 3 wk the sucrose-fed rats (compared with the R group) were characterized by the following: 1) higher insulin responses after a glucose challenge (P < 0.05); 2) heavier liver (P < 0.001) and retroperitoneal adipose tissue (P < 0.01); 3) hypertriglyceridemia (P < 0.0001) and higher plasma free fatty acids (P < 0.0001); and 4) higher fatty acid synthase activity in the liver but a low activity in the adipose tissue (P < 0.001). The addition of FOS to the diet resulted in 11% lower liver weight than in the S group (P < 0.05) and tended to result in lower adipose tissue weight (P < 0.11). Plasma triglycerides and plasma free fatty acids were lower in S/FOS- than in S-fed rats (P < 0.05). Chylomicrons + VLDL, and intermediate density lipoprotein (IDL) concentrations did not differ between groups, nor was plasma cholesterol influenced by diet. Hepatic FAS activity was lower in S/FOS-fed rats than in the S-fed rats (P < 0.05). In adipose tissue, however, this activity tended to be greater in rats fed S/FOS than in rats fed the S diet (P < 0.07). In conclusion, in a rat model of diet-induced (57.5% sucrose and 14% lipids) insulin resistance, the addition of short-chain FOS prevented some lipid disorders, lowered fatty acid synthase activity in the liver and tended to raise this activity in the adipose tissue. Short-chain FOS, in addition to being a nondigestible sweetener with good bulking capacity, might be useful in the treatment of insulin resistance and hyperlipidemia. PMID:9687545

Agheli, N; Kabir, M; Berni-Canani, S; Petitjean, E; Boussairi, A; Luo, J; Bornet, F; Slama, G; Rizkalla, S W

1998-08-01

321

Health Aspects of Dietary 'Trans' Fatty Acids.  

National Technical Information Service (NTIS)

The report of an ad hoc Review Panel examines the available information on the health aspects of dietary trans fatty acids. The report concludes that the available scientific information suggests little reason for concern with the safety of dietary trans ...

1985-01-01

322

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...

323

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

Microsoft Academic Search

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

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

2001-01-01

324

Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1  

PubMed Central

Prostaglandins (PG) are known to induce pain perception indirectly by sensitizing nociceptors. Accordingly, the analgesic action of nonsteroidal anti-inflammatory drugs (NSAIDs) results from inhibition of cyclooxygenases and blockade of PG biosynthesis. Cyclopentenone PGs, 15-d-PGJ2, PGA2, and PGA1, formed by dehydration of their respective parent PGs, PGD2, PGE2, and PGE1, possess a highly reactive ?,?-unsaturated carbonyl group that has been proposed to gate the irritant transient receptor potential A1 (TRPA1) channel. Here, by using TRPA1 wild-type (TRPA1+/+) or deficient (TRPA1?/?) mice, we show that cyclopentenone PGs produce pain by direct stimulation of nociceptors via TRPA1 activation. Cyclopentenone PGs caused a robust calcium response in dorsal root ganglion (DRG) neurons of TRPA1+/+, but not of TRPA1?/? mice, and a calcium-dependent release of sensory neuropeptides from the rat dorsal spinal cord. Intraplantar injection of cyclopentenone PGs stimulated c-fos expression in spinal neurons of the dorsal horn and evoked an instantaneous, robust, and transient nociceptive response in TRPA1+/+ but not in TRPA1?/? mice. The classical proalgesic PG, PGE2, caused a slight calcium response in DRG neurons, increased c-fos expression in spinal neurons, and induced a delayed and sustained nociceptive response in both TRPA1+/+ and TRPA1?/? mice. These results expand the mechanism of NSAID analgesia from blockade of indirect nociceptor sensitization by classical PGs to inhibition of direct TRPA1-dependent nociceptor activation by cyclopentenone PGs. Thus, TRPA1 antagonism may contribute to suppress pain evoked by PG metabolites without the adverse effects of inhibiting cyclooxygenases.

Materazzi, Serena; Nassini, Romina; Andre, Eunice; Campi, Barbara; Amadesi, Silvia; Trevisani, Marcello; Bunnett, Nigel W.; Patacchini, Riccardo; Geppetti, Pierangelo

2008-01-01

325

Fatty acid methodology for heated oils  

Microsoft Academic Search

Criticisms have been voiced concerning the methods employed for determining the fatty acid composition of vegetable oils used\\u000a in processing of fried foods. In the present study seveveral different vegetable oils were heated under standardized conditions,\\u000a at frying temperatures and under air, for various periods of time, and then subjected to analyses for fatty acid composition.\\u000a The methods employed were:

Arthur E. Waltking; Helen Zmachinski

1970-01-01

326

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

327

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

328

Genetic variability of milk fatty acids  

Microsoft Academic Search

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

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

2009-01-01

329

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...

330

Disruption of fatty acid amide hydrolase activity prevents the effects of chronic stress on anxiety and amygdalar microstructure.  

PubMed

Hyperactivation of the amygdala following chronic stress is believed to be one of the primary mechanisms underlying the increased propensity for anxiety-like behaviors and pathological states; however, the mechanisms by which chronic stress modulates amygdalar function are not well characterized. The aim of the current study was to determine the extent to which the endocannabinoid (eCB) system, which is known to regulate emotional behavior and neuroplasticity, contributes to changes in amygdalar structure and function following chronic stress. To examine the hypothesis, we have exposed C57/Bl6 mice to chronic restraint stress, which results in an increase in fatty acid amide hydrolase (FAAH) activity and a reduction in the concentration of the eCB N-arachidonylethanolamine (AEA) within the amygdala. Chronic restraint stress also increased dendritic arborization, complexity and spine density of pyramidal neurons in the basolateral nucleus of the amygdala (BLA) and increased anxiety-like behavior in wild-type mice. All of the stress-induced changes in amygdalar structure and function were absent in mice deficient in FAAH. Further, the anti-anxiety effect of FAAH deletion was recapitulated in rats treated orally with a novel pharmacological inhibitor of FAAH, JNJ5003 (50?mg per kg per day), during exposure to chronic stress. These studies suggest that FAAH is required for chronic stress to induce hyperactivity and structural remodeling of the amygdala. Collectively, these studies indicate that FAAH-mediated decreases in AEA occur following chronic stress and that this loss of AEA signaling is functionally relevant to the effects of chronic stress. These data support the hypothesis that inhibition of FAAH has therapeutic potential in the treatment of anxiety disorders, possibly by maintaining normal amygdalar function in the face of chronic stress. PMID:22776900

Hill, M N; Kumar, S A; Filipski, S B; Iverson, M; Stuhr, K L; Keith, J M; Cravatt, B F; Hillard, C J; Chattarji, S; McEwen, B S

2012-07-10

331

Are free fatty acids related to plasma plasminogen activator inhibitor 1 in android obesity?  

PubMed

Plasminogen activator inhibitor 1 (PAI-1) levels are elevated in obese insulin-resistant subjects. However the mechanism underlying increased PAI-1 levels is unknown. To determine the impact of diabetes on PAI-1 levels and its possible relationship to insulin resistance, hyperinsulinemic euglycemic clamp studies were performed in nine lean control subjects, nine non-diabetic obese subjects and eight obese patients with NIDDM. Fasting plasma PAI-1 levels were 4.0 to 4.7 fold higher in the two obese groups than in the control group. During the 40 mU/m2 x min insulin infusion, suppression of FFA concentration was correlated with fasting plasma PAI-1 levels in both obese non-diabetic and obese NIDDM subjects. It is concluded that (1) obesity rather than diabetes itself plays a major role for the increased PAI-1 levels in NIDDM; (2) resistance to the antilipolytic effect of insulin, resulting in increased FFA concentrations, may participate in producing elevated PAI-1 levels in android obese subjects. PMID:8589788

Bastard, J P; Bruckert, E; Robert, J J; Ankri, A; Grimaldi, A; Jardel, C; Hainque, B

1995-11-01

332

Dietary omega-3 fatty acids for women.  

PubMed

This review details the specific needs of women for omega-3 fatty acids, including alpha linoleic acid (ALA) and the very long chain fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Omega-3 fatty acid (dietary or in capsules) ensures that a woman's adipose tissue contains a reserve of these fatty acids for the developing fetus and the breast-fed newborn infant. This ensures the optimal cerebral and cognitive development of the infant. The presence of large quantities of EPA and DHA in the diet slightly lengthens pregnancy, and improves its quality. Human milk contains both ALA and DHA, unlike that of other mammals. Conditions such as diabetes can alter the fatty acid profile of mother's milk, while certain diets, like those of vegetarians, vegans, or even macrobiotic diets, can have the same effect, if they do not include seafood. ALA, DHA and EPA, are important for preventing ischemic cardiovascular disease in women of all ages. Omega-3 fatty acids can help to prevent the development of certain cancers, particularly those of the breast and colon, and possibly of the uterus and the skin, and are likely to reduce the risk of postpartum depression, manic-depressive psychosis, dementias (Alzheimer's disease and others), hypertension, toxemia, diabetes and, to a certain extend, age-related macular degeneration. Omega-3 fatty acids could play a positive role in the prevention of menstrual syndrome and postmenopausal hot flushes. The normal western diet contains little ALA (less than 50% of the RDA). The only adequate sources are rapeseed oil (canola), walnuts and so-called "omega-3" eggs (similar to wild-type or Cretan eggs). The amounts of EPA and DHA in the diet vary greatly from person to person. The only good sources are fish and seafood, together with "omega-3" eggs. PMID:17254747

Bourre, Jean-Marie

2007-01-02

333

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 Dyrřy; Rolf K. Berge

1999-01-01

334

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

335

Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni).  

PubMed

A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM). PMID:20032599

Akihisa, Toshihiro; Seino, Ken-ichi; Kaneko, Etsuyo; Watanabe, Kensuke; Tochizawa, Shun; Fukatsu, Makoto; Banno, Norihiro; Metori, Koichi; Kimura, Yumiko

2010-01-01

336

Sex Steroid Modulation of Fatty Acid Utilization and Fatty Acid Binding Protein Concentration in Rat Liver  

PubMed Central

The mechanism by which sex steroids influence very low density hepatic lipoprotein triglyceride production has not been fully elucidated. In previous studies we showed that [14C]oleate utilization and incorporation into triglycerides were greater in hepatocyte suspensions from adult female rats than from males. The sex differences were not related to activities of the enzymes of triglyceride biosynthesis, whereas fatty acid binding protein (FABP) concentration in liver cytosol was greater in females. These findings suggested that sex differences in lipoprotein could reflect a sex steroid influence on the availability of fatty acids for hepatocellular triglyceride biosynthesis. In the present studies, sex steroid effects on hepatocyte [14C]oleate utilization and FABP concentration were investigated directly. Hepatocytes from immature (30-d-old) rats exhibited no sex differences in [14C]oleate utilization. With maturation, total [14C]oleate utilization and triglyceride biosynthesis increased moderately in female cells and decreased markedly in male cells; the profound sex differences in adults were maximal by age 60 d. Fatty acid oxidation was little affected. Rats were castrated at age 30 d, and received estradiol, testosterone, or no hormone until age 60 d, when hepatocyte [14C]oleate utilization was studied. Castration virtually eliminated maturational changes and blunted the sex differences in adults. Estradiol or testosterone largely reproduced the appropriate adult pattern of [14C]oleate utilization regardless of the genotypic sex of the treated animal. In immature females and males, total cytosolic FABP concentrations were similar. In 60-d-old animals, there was a striking correlation among all groups (females, males, castrates, and hormone-treated) between mean cytosolic FABP concentration on the one hand, and mean total [14C]oleate utilization (r = 0.91) and incorporation into triglycerides (r = 0.94) on the other. In 30-d-old animals rates of [14C]oleate utilization were greater, relative to FABP concentrations, than in 60-d-old animals. The sex differences that characterize fatty acid utilization in adult rat hepatocytes are not present in cells from immature animals, and reflect in part the influence of sex steroids. It remains to be determined whether the observed relationship of hepatic FABP concentration to [14C]oleate utilization in adult cells is causal or secondary to changes in cellular fatty acid uptake effected through another mechanism. In either case, modulation of triglyceride-rich lipoprotein production by six steroids appears to be mediated to a significant extent by their effects on hepatic fatty acid utilization.

Ockner, Robert K.; Lysenko, Nina; Manning, Joan A.; Monroe, Scott E.; Burnett, David A.

1980-01-01

337

Changes in Na+/K+-ATPase activity, unsaturated fatty acids and metallothioneins in gills of the shore crab Carcinus aestuarii after dilute seawater acclimation.  

PubMed

We have assessed the activity of Na(+)/K(+)-ATPase, cAMP, free fatty acids (FFA) and metallothionein (MT) in the posterior gills of the brackish water shore crab Carcinus aestuarii during acclimation to 10 ppt dilute seawater (DSW). Following 3-18 days acclimation in DSW specific activity of Na(+)/K(+)-ATPase in native gill homogenates and partially purified membrane vesicles was progressively increased, from 1.7- to 3.9-fold. After short-term acclimation of crabs in DSW with added sucrose to make media isosmotic with the haemolymph the specific Na(+)/K(+)-ATPase activity in homogenates was not increased, relative to SW enzyme activity. Moreover, hyposmotic conditions led to depletion of cAMP in gills. In partially purified membrane vesicles isolated from posterior gills, fatty acids with compositions 16:0, 18:0, 18:1, 20:4 and 20:5 dominated in both SW- and DSW-acclimated Carcinus. During a year in which the metabolic activity of crabs was increased, the arachidonic/linoleic acids ratio (ARA/LA) for DSW-acclimated crabs was markedly increased relative to that in SW. Increased Na(+)+K(+)-ATPase activity under hyposmotic stress may be modulated at least partially by the changed proportion of fatty acids in the purified membranes of posterior gills. Long-term acclimation of shore crabs to DSW resulted in a 2.6-fold increase in cytosolic metallothionein (MT) content in posterior gills over those in SW crabs. Assuming an antioxidant role of MT associated with intracellular zinc partitioning, the observed MT induction in posterior gills may be considered an adaptive response of C. aestuarii to hyposmotic stress. PMID:18325806

Lucu, C; Pavici?, J; Ivankovi?, D; Pavici?-Hamer, D; Najdek, M

2008-02-02

338

Effect of a high-linolenic acid diet on lipogenic enzyme activities, fatty acid composition, and meat quality in the growing pig.  

PubMed

Forty-eight Duroc-cross gilts (40 kg initial BW) were fed a control or a linseed diet containing 60 g of whole crushed linseed/kg. Both diets were supplemented with 150 mg of vitamin E/kg. Eight pigs from each dietary treatment were slaughtered at 20, 60, or 100 d after the start of the experiment. There was no effect (P > 0.05) of diet on growth, carcass characteristics, or foreloin tissue composition. Feeding the linseed diet increased (P < 0.05) the content of n-3 PUFA in plasma, muscle, and adipose tissue, but docosahexaenoic acid was not (P > 0.05) altered by diet. The proportions of n-3 PUFA were highest (P < 0.01) in pigs fed the linseed-diet for 60 d, regardless of tissue (plasma, muscle, or adipose tissue) or lipid (neutral lipids and phospholipids) class. The linseed diet produced a PUFA:saturated fatty acid ratio > or = 0.4 in all groups and tissues, which is close to the recommended value for the entire diet of humans, as well as a robust decrease in the n-6:n-3 ratio. The decrease (P < 0.01) in the percentage of oleic acid in adipose tissue of pigs fed the linseed diet for 60 d could be attributed to a 40% decrease (P < 0.001) in stearoyl-CoA-desaturase activity. Diet did not (P > 0.05) affect the activities of acetyl-CoA-carboxylase, malic enzyme, or glucose-6-phosphate-dehydrogenase in any tissues. Muscle vitamin E content was decreased (P < 0.001) 30% in pigs fed crushed linseed for 60 d, whereas lower (P < 0.001) concentrations of skatole in pork fat were observed in linseed-fed pigs at all slaughter times. Inclusion of linseed (flaxseed) in swine diets is a valid method of improving the nutritional value of pork without deleteriously affecting organoleptic characteristics, oxidation, or color stability. PMID:12926779

Kouba, M; Enser, M; Whittington, F M; Nute, G R; Wood, J D

2003-08-01

339

n-3 and n-6 Polyunsaturated fatty acids induce the expression of COX2 via PPAR? activation in human keratinocyte HaCaT cells  

Microsoft Academic Search

Polyunsaturated fatty acids (PUFA) n-3 inhibit inflammation, in vivo and in vitro in keratinocytes. We examined in HaCaT keratinocyte cell line whether eicosapentaenoic acid (EPA) a n-3 PUFA, gamma-linoleic acid (GLA) a n-6 PUFA, and arachidic acid a saturated fatty acid, modulate expression of cyclooxygenase-2 (COX-2), an enzyme pivotal to skin inflammation and reparation. We demonstrate that only treatment of

Gérald Chęne; Marc Dubourdeau; Patricia Balard; Laure Escoubet-Lozach; Claudine Orfila; Antoine Berry; José Bernad; Marie-Françoise Aries; Marie Charveron; Bernard Pipy

2007-01-01

340

Acute regulation of 5?-AMP-activated protein kinase by long-chain fatty acid, glucose and insulin in rat primary adipocytes  

PubMed Central

Palmitate increased AMPK (5?-AMP-activated protein kinase) activity, glucose utilization and 2-DOG (2-deoxyglucose) transport in rat adipocytes. All three effects were blocked by the AMPK inhibitor Compound C, leading to the conclusion that in response to an increase in long-chain NEFA (non-esterified fatty acid) concentration AMPK mediated an enhancement of adipocyte glucose transport, thereby providing increased glycerol 3-phosphate for FA (fatty acid) esterification to TAG (triacylglycerol). Activation of AMPK in response to palmitate was not due to an increase in the adipocyte AMP:ATP ratio. Glucose decreased AMPK activity and effects of palmitate and glucose on AMPK activity were antagonistic. While insulin had no effect on basal AMPK activity insulin did decrease AMPK activity in the presence of palmitate and also decreased the percentage effectiveness of palmitate to increase the transport of 2-DOG. It is suggested that activation of adipocyte AMPK by NEFA, as well as decreasing the activity of hormone-sensitive lipase, could modulate adipose tissue dynamics by increasing FA esterification and, under certain circumstances, FA synthesis.

Hebbachi, Abdel; Saggerson, David

2012-01-01

341

Essential fatty acids of pitaya (dragon fruit) seed oil  

Microsoft Academic Search

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

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

2009-01-01

342

Linoleic acid requirement of rats fed trans fatty acids  

Microsoft Academic Search

The amount of linoleic acid required to prevent undesirable effects of C18trans fatty acids was investigated. In a first experiment, six groups of rats were fed diets with a high content oftrans fatty acids (20% of energy [en%]), and increasing amounts of linoleic acid (0.4 to 7.1 en%). In a second experiment, four\\u000a groups of rats were fed diets designed

J. L. Zevenbergen; U. M. T. Houtsmuller; J. J. Gottenbos

1988-01-01

343

Effect of dietary intake on the levels of biliary unsaturated free Fatty acids having inhibitory activity on mutagens.  

PubMed

Unsaturated free fatty acids (FFAs), such as palmitoleic, oleic, linoleic, linolenic and arachidonic acids, have inhibitory actions on mutagenesis. These FFAs in bile may play a role in preventing cholecystopathy and their levels may be influenced by diet. However, the effects of dietary intake on biliary FFAs levels are not known. In order to examine possible associations between dietary habits and biliary FFAs levels, bile samples were collected from resected gallbladders of 114 Chilean female patients with gallstones, and FFAs were measured with an HPLC system. The long-term dietary intake of the patients was investigated through a semi-quantitative food frequency questionnaire. A high intake of vegetables was negatively correlated with the total FFA level (r = -0.264, P = 0.010). Positive correlations were found between fruit consumption and the lauric acid level (r = 0.200, P = 0.041), fish consumption and the levels of oleic (r = 0.370, P <0.0001), linolenic (r = 0.197, P = 0.038) and arachidonic (r = 0.200, P =0.035) acids, and consumption of foods fried in vegetable oil and the linoleic acid level (r = 0.269, P =0.004). Linoleic, linolenic, and arachidonic acids which may have an inhibitory effect on actions of unknown mutagens in bile appear to be increased by consumption of high levels of fish and fried foods. PMID:20104986

Serra, Iván; Tsuchiya, Yasuo; Hori, Yasushi; Villegas, Rodrigo; Oyama, Mari; Makiguchi, Tomoo; Yamamoto, Masaharu; Nakamura, Kazutoshi

2009-01-01

344

Omega-3 fatty acids and inflammation.  

PubMed

Dietary omega-3 (n-3) fatty acids have a variety of anti-inflammatory and immune-modulating effects that may be of relevance to atherosclerosis and its clinical manifestations of myocardial infarction, sudden death, and stroke. The n-3 fatty acids that appear to be most potent in this respect are the long-chain polyunsaturates derived from marine oils, namely eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), and this review is restricted to these substances. A variety of biologic effects of EPA and DHA have been demonstrated from feeding studies with fish or fish oil supplements in humans and animals. These include effects on triglycerides, high-density lipoprotein cholesterol, platelet function, endothelial and vascular function, blood pressure, cardiac excitability, measures of oxidative stress, pro- and anti-inflammatory cytokines, and immune function. Epidemiologic studies provide evidence for a beneficial effect of n-3 fatty acids on manifestations of coronary heart disease and ischemic stroke, whereas randomized, controlled, clinical feeding trials support this, particularly with respect to sudden cardiac death in patients with established disease. Clinically important anti-inflammatory effects in man are further suggested by trials demonstrating benefits of n-3 fatty acids in rheumatoid arthritis, psoriasis, asthma, and inflammatory bowel disorders. Given the evidence relating progression of atherosclerosis to chronic inflammation, the n-3 fatty acids may play an important role via modulation of the inflammatory processes. PMID:15485592

Mori, Trevor A; Beilin, Lawrence J

2004-11-01

345

Ferritin couples iron and fatty acid metabolism.  

PubMed

A physiological relationship between iron, oxidative injury, and fatty acid metabolism exists, but transduction mechanisms are unclear. We propose that the iron storage protein ferritin contains fatty acid binding sites whose occupancy modulates iron uptake and release. Using isothermal microcalorimetry, we found that arachidonic acid binds ferritin specifically and with 60 ?M affinity. Arachidonate binding by ferritin enhanced iron mineralization, decreased iron release, and protected the fatty acid from oxidation. Cocrystals of arachidonic acid and horse spleen apoferritin diffracted to 2.18 ? and revealed specific binding to the 2-fold intersubunit pocket. This pocket shields most of the fatty acid and its double bonds from solvent but allows the arachidonate tail to project well into the ferrihydrite mineralization site on the ferritin L-subunit, a structural feature that we implicate in the effects on mineralization by demonstrating that the much shorter saturated fatty acid, caprylate, has no significant effects on mineralization. These combined effects of arachidonate binding by ferritin are expected to lower both intracellular free iron and free arachidonate, thereby providing a previously unrecognized mechanism for limiting lipid peroxidation, free radical damage, and proinflammatory cascades during times of cellular stress. PMID:22362897

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

2012-02-23

346

Influence of fatty acid profile of total parenteral nutrition emulsions on the fatty acid composition of different tissues of piglets.  

PubMed

Total parenteral nutrition (TPN) studies in human babies of very-low-birth-weight suggest that the lipid emulsions currently available are not optimum for neonatal nutrition. Since fatty acid metabolism in human and pigs is very similar, the present study examines how lipid emulsions used in clinical TPN (i.e. ClinOleic, Intralipid, Lipofundin or Omegaven), with different fatty acid compositions, administered to neonatal piglets for 7 days, influenced their tissue fatty acid composition as compared to those enterally fed with a sow milk replacer. A positive linear relationship was found between the proportion of all individual fatty acids in the lipid emulsions or in the milk replacer versus those in plasma, skeletal muscle, subcutaneous fat, liver, heart, pancreas, stomach or intestine total lipids or in brain phospholipids, the latter showing the lowest correlation coefficient. With the exception of brain, the proportion of either oleic acid or alpha-linolenic acid in the individual tissues was correlated with those present in the corresponding lipid emulsion or milk replacer, whereas the proportion of linoleic acid correlated significantly with all the tissues studied. With the exception of brain phospholipids, both eicosapentaenoic and docosahexaenoic acids were higher in the tissues of piglets receiving Omegaven than in all other groups. In conclusion, with the exception of the brain, fatty acid composition of plasma and different tissues in piglets are strongly influenced by the fatty acid profile of TPN emulsions. Fatty acid composition of brain phospholipids are, however, much less influenced by dietary composition, indicating an active and efficient metabolism that ensures its appropriate composition at this key stage of development. PMID:18491157

Amusquivar, E; Sánchez, M; Hyde, M J; Laws, J; Clarke, L; Herrera, E

2008-05-09

347

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

PubMed Central

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

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

2013-01-01

348

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

2013-01-04

349

The synthesis of fatty acid ethyl ester by carboxylester lipase.  

PubMed

Carboxylester lipase obtained from pig pancreas is associated with fatty acid ethyl ester synthase as judged by their elution in the same fraction from a heparin-Sepharose column, coprecipitations by antibody against purified carboxylester lipase and identical profiles of inhibition by diisopropyl fluorophosphate. Only one polypeptide of molecular mass 74-kDa in purified carboxylester lipase was labeled by immunostaining and affinity labeling with [3H]diisopropyl fluorosphate. Bovine serum albumin decreased the fatty-acid-ethyl-ester-synthesizing activity in a concentration-dependent manner. On incubation of purified carboxylester lipase with trioleylglycerol in an ethanol/water mixture, fatty acid ethyl ester was formed in the presence of a high concentration of bovine serum albumin. The acyltransfer activities from trioleylglycerol to ethanol (ethanolysis) were approximately 25-30 times higher than the acyltransfer activities to water (hydrolysis). When cholesterol was used as an acceptor, acyltransfer activity from trioleylglycerol to cholesterol (cholesterolysis) was also observed. We propose the following mechanism of fatty acid ethyl ester formation from triacyl glycerol. The enzyme attacks triacyl glycerol forming an acyl-enzyme intermediate, and during the deacylation process, alcohol binds to fatty acid as an acceptor. These results suggest that during lipid (triacyl glycerol) degradation, carboxylester lipase contributes to non-oxidative ethanol metabolism in the intestinal lumen. PMID:8076651

Tsujita, T; Okuda, H

1994-08-15

350

Fatty acid profile and in vitro antioxidant and antibacterial activities of red grape (Vitis vinifera L. cvs. Oküzgözü and Bo?azkere) Marc extracts.  

PubMed

The marcs of two red grape (V. vinifera L.) varieties (Bo?azkere and Oküzgözü), grown in eastern Anatolia (Elazig), were evaluated for their fatty acid composition, and antioxidant and antibacterial activities. The hexane extracts of both varieties were found to contain linoleic, palmitic, stearic and oleic acids by GC-MS analyses. The major fatty acid (linoleic acid) was detected relatively as 57.13% in Oküzgözü and 59.07% in Bogazkere in methylated hexane extracts. In addition, myristic and palmitoleic acids were observed in Bo?azkere as minor components. The free radical (DPPH) scavenging activity of Oküzgözü was higher than that of Bogazkere. The IC50 values were calculated as 403.0 +/- 7.8 microg/mL for Oküzgozü and 552.0 +/- 23.6 microg/mL for Bogazkere. The extracts were found to be effective on the four gram (+) and four gram (-) test bacteria, but not as good as standard antibiotic, gentamycine by MIC method. PMID:19413121

Cibik, Bilge; Ozaydin, Zuhal; Böke, Nazli; Karabay, Ulkü; Pekmez, Murat; Arda, Nazhi; Kirmizigüla, Süheyla

2009-03-01

351

Soil bacterial biomass, activity, phospholipid fatty acid pattern, and pH tolerance in an area polluted with alkaline dust deposition  

SciTech Connect

In a study of response of soil microbes to emissions from an iron and steel works, microbial biomass in the humus horizon of the forest was similar in polluted sites (soil pH of 6.6) and unpolluted areas (soil pH of 4.1). However, drastic changes in the microfungal species composition in polluted areas was also found in an earlier study. The extend of changes in the bacterial community is more difficult to study. Phospholipid fatty acid (PLFA) patterns of a soil can overcome this since different groups of bacteria are characterized by specific PFLA profiles. A changed tolerance pattern of the bacteria, examined through the thymidine incorporation technique, can also be used. This study investigates the effect of increased pH on the biomass, growth rate, PLFA pattern, and pH tolerance of the soil bacterial community. The effects of alkaline pollution are very similar to the effects found after liming a forest soil including the following: increased bacterial activity; decreased turnover time; increase in gram-negative bacterial fatty acids and decrease in gram-positive bacterial fatty acids; altered pH tolerance.

Baath, E.; Frostegaard, A. (Lund Univ. (Sweden)); Fritze, H. (Finnish Forest Research Inst., Vantaa (Finland))

1992-12-01

352

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.

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

2008-01-01

353

Occurrence of fatty alcohol oxidase in alkane-and fatty-acid-utilising yeasts and moulds  

Microsoft Academic Search

Preparations of membrane fractions from 16 yeasts and three moulds were assayed for long-chain fatty alcohol oxidase (FAOD) activities after being grown on hexadecane or glucose and, in nine cases, on oleic acid. The enzyme was usually repressed in glucose-grown cells but in Candida bombicola ATCC 22 214 and Debaryomyces hansenii NCYC 33 appeared to be constitutive. Highest activities occurred

Glen D. Kemp; F. Mark Dickinson; Colin Ratledge

1994-01-01

354

Production of hydroxylated fatty acids in genetically modified plants  

Microsoft Academic Search

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

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

2011-01-01

355

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

Microsoft Academic Search

Background  Cyclopropane fatty acids (CPA) have been found in certain gymnosperms, Malvales, Litchi and other Sapindales. The presence\\u000a of their unique strained ring structures confers physical and chemical properties characteristic of unsaturated fatty acids\\u000a with the oxidative stability displayed by saturated fatty acids making them of considerable industrial interest. While cyclopropenoid\\u000a fatty acids (CPE) are well-known inhibitors of fatty acid desaturation

Xiao-Hong Yu; Richa Rawat; John Shanklin

2011-01-01

356

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

Microsoft Academic Search

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

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

2008-01-01

357

2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani.  

PubMed

2-Alkynoic fatty acids display antimycobacterial, antifungal, and pesticidal activities but their antiprotozoal activity has received little attention. In this work we synthesized the 2-octadecynoic acid (2-ODA), 2-hexadecynoic acid (2-HDA), and 2-tetradecynoic acid (2-TDA) and show that 2-ODA is the best inhibitor of the Leishmania donovani DNA topoisomerase IB enzyme (LdTopIB) with an EC(50)=5.3±0.7?M. The potency of LdTopIB inhibition follows the trend 2-ODA>2-HDA>2-TDA, indicating that the effectiveness of inhibition depends on the fatty acid carbon chain length. All of the studied 2-alkynoic fatty acids were less potent inhibitors of the human topoisomerase IB enzyme (hTopIB) as compared to LdTopIB. 2-ODA also displayed in vitro activity against Leishmania donovani (IC(50)=11.0?M), but it was less effective against other protozoa, Trypanosoma cruzi (IC(50)=48.1?M) and Trypanosoma brucei rhodesiense (IC(50)=64.5?M). The antiprotozoal activity of the 2-alkynoic fatty acids, in general, followed the trend 2-ODA>2-HDA>2-TDA. The experimental information gathered so far indicates that 2-ODA is a promising antileishmanial compound. PMID:22932312

Carballeira, Néstor M; Cartagena, Michelle; Sanabria, David; Tasdemir, Deniz; Prada, Christopher F; Reguera, Rosa M; Balańa-Fouce, Rafael

2012-08-10

358

2-Alkynoic fatty acids inhibit Topoisomerase IB from Leishmania donovani  

PubMed Central

2-Alkynoic fatty acids display antimycobacterial, antifungal, and pesticidal activities but their antiprotozoal activity has received little attention. In this work we synthesized the 2-octadecynoic acid (2-ODA), 2-hexadecynoic acid (2-HDA), and 2-tetradecynoic acid (2-TDA) and show that 2-ODA is the best inhibitor of the Leishmania donovani DNA topoisomerase IB enzyme (LdTopIB) with an EC50 = 5.3 ± 0.7 ?M. The potency of LdTopIB inhibition follows the trend 2-ODA> 2-HDA> 2-TDA, indicating that the effectiveness of inhibition depends on the fatty acid carbon chain length. All of the studied 2-alkynoic fatty acids were less potent inhibitors of the human topoisomerase IB enzyme (hTopIB) as compared to LdTopIB. 2-ODA also displayed in vitro activity against Leishmania donovani (IC50 = 11.0 ?M), but it was less effective against other protozoa, Trypanosoma cruzi (IC50 = 48.1 ?M) and T. brucei rhodesiense (IC50 = 64.5 ?M). The antiprotozoal activity of the 2-alkynoic fatty acids, in general, followed the trend 2-ODA> 2-HDA> 2-TDA. The experimental information gathered so far indicates that 2-ODA is a promising antileishmanial compound.

Carballeira, Nestor M.; Cartagena, Michelle; Sanabria, David; Kaiser, Marcel; Tasdemir, Deniz; Prada, Christopher F.; Reguera, Rosa M.; Balana-Fouce, Rafael

2012-01-01

359

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

360

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.

Warensjo, Eva; Rosell, Magdalena; Hellenius, Mai-Lis; Vessby, Bengt; De Faire, Ulf; Riserus, Ulf

2009-01-01

361

Intrinsic acyl-CoA thioesterase activity of a peroxisomal ATP binding cassette transporter is required for transport and metabolism of fatty acids.  

PubMed

Peroxisomes are organelles that perform diverse metabolic functions in different organisms, but a common function is ?-oxidation of a variety of long chain aliphatic, branched, and aromatic carboxylic acids. Import of substrates into peroxisomes for ?-oxidation is mediated by ATP binding cassette (ABC) transporter proteins of subfamily D, which includes the human adrenoleukodystropy protein (ALDP) defective in X-linked adrenoleukodystrophy (X-ALD). Whether substrates are transported as CoA esters or free acids has been a matter of debate. Using COMATOSE (CTS), a plant representative of the ABCD family, we demonstrate that there is a functional and physical interaction between the ABC transporter and the peroxisomal long chain acyl-CoA synthetases (LACS)6 and -7. We expressed recombinant CTS in insect cells and showed that membranes from infected cells possess fatty acyl-CoA thioesterase activity, which is stimulated by ATP. A mutant, in which Serine 810 is replaced by asparagine (S810N) is defective in fatty acid degradation in vivo, retains ATPase activity but has strongly reduced thioesterase activity, providing strong evidence for the biological relevance of this activity. Thus, CTS, and most likely the other ABCD family members, represent rare examples of polytopic membrane proteins with an intrinsic additional enzymatic function that may regulate the entry of substrates into the ?-oxidation pathway. The cleavage of CoA raises questions about the side of the membrane where this occurs and this is discussed in the context of the peroxisomal coenzyme A (CoA) budget. PMID:23288899

De Marcos Lousa, Carine; van Roermund, Carlo W T; Postis, Vincent L G; Dietrich, Daniela; Kerr, Ian D; Wanders, Ronald J A; Baldwin, Stephen A; Baker, Alison; Theodoulou, Frederica L

2013-01-03

362

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

363

Prolonged feeding of mice with conjugated linoleic acid increases hepatic fatty acid synthesis relative to oxidation  

Microsoft Academic Search

Feeding mice conjugated linoleic acid (9 cis,11 trans\\/9 trans,11 cis-and 10 trans,12 cis-CLA in equal amounts) resulted in triacylglycerol accumulation in the liver. The objective of this study was to examine whether this steatosis is associated with changes in hepatic fatty acid synthesis and oxidation. Therefore, we measured the activities of key enzymes of fatty acid synthesis, i.e., acetyl-CoA carboxylase

Marjan Javadi; Anton C. Beynen; Robert Hovenier; Ćgidius Lankhorst; Arnoldina G. Lemmens; Antonius H. M. Terpstra; Math J. H. Geelen

2004-01-01

364

Fatty acid production in Schizochytrium sp.: Involvement of a polyunsaturated fatty acid synthase and a type I fatty acid synthase  

Microsoft Academic Search

Schizochytrium sp. is a marine microalga that has been developed as a commercial source for docosahexaenoic acid (DHA, C22?6 ??3), enriched\\u000a biomass, and oil. Previous work suggested that the DHA, as well as docosapentaenoic acid (DPA, C22?5 ??6), that accumulate\\u000a in Schizochytrium are products of a multi-subunit polyunsaturated fatty acid (PUFA) synthase (1). Here we show data to support this

A. Hauvermale; J. Kuner; B. Rosenzweig; D. Guerra; S. Diltz; J. G. Metz

2006-01-01

365

Fatty acid production in Schizochytrium sp.: Involvement of a polyunsaturated fatty acid synthase and a type I fatty acid synthase.  

PubMed

Schizochytrium sp. is a marine microalga that has been developed as a commercial source for docosahexaenoic acid (DHA, C22:6 (omega-3), enriched biomass, and oil. Previous work suggested that the DHA, as well as docosapentaenoic acid (DPA, C22:5 omega-6), that accumulate in Schizochytrium are products of a multi-subunit polyunsaturated fatty acid (PUFA) synthase (1). Here we show data to support this view and also provide information on other aspects of fatty acid synthesis in this organism. Three genes encoding subunits of the PUFA synthase were isolated from genomic DNA and expressed in E. coli along with an essential accessory gene encoding a phosphopantetheinyl transferase (PPTase). The resulting transformants accumulated both DHA and DPA. The ratio of DHA to DPA was approximately the same as that observed in Schizochytrium. Treatment of Schizochytrium cells with certain levels of cerulenin resulted in inhibition of 14C acetate incorporation into short chain fatty acids without affecting labeling of PUFAs, indicating distinct biosynthetic pathways. A single large gene encoding the presumed short chain fatty acid synthase (FAS) was cloned and sequenced. Based on sequence homology and domain organization, the Schizochytrium FAS resembles a fusion of fungal FAS beta and alpha subunits. PMID:17120926

Hauvermale, A; Kuner, J; Rosenzweig, B; Guerra, D; Diltz, S; Metz, J G

2006-08-01

366

Elevated hepatic fatty acid elongase-5 activity corrects dietary fat-induced hyperglycemia in obese BL/6J mice[S  

PubMed Central

Elevated hepatic fatty acid elongase-5 (Elovl5) activity lowers blood glucose in fasted chow-fed C57BL/6J mice. As high-fat diets induce hyperglycemia and suppress hepatic Elovl5 activity, we tested the hypothesis that elevated hepatic Elovl5 expression attenuates hyperglycemia in high-fat-diet-induced obese mice. Increasing hepatic Elovl5 activity by a recombinant adenoviral approach restored blood glucose and insulin, HOMA-IR, and glucose tolerance to normal values in obese mice. Elevated Elovl5 activity increased hepatic content of Elovl5 products (20:3,n-6, 22:4,n-6) and suppressed levels of enzymes (Pck1, G6Pc) and transcription factors (FoxO1 and PGC1?, but not CRTC2) involved in gluconeogenesis. Effects of Elovl5 on FoxO1 nuclear abundance correlated with increased phosphorylation of FoxO1, Akt, and the catalytic unit of PP2A, as well as a decline in cellular abundance of TRB3. Such changes are mechanistically linked to the regulation of FoxO1 nuclear abundance and gluconeogenesis. These results show that Elovl5 activity impacts the hepatic abundance and phosphorylation status of multiple proteins involved in gluconeogenesis. Our findings establish a link between fatty acid elongation and hepatic glucose metabolism and suggest a role for regulators of Elovl5 activity in the treatment of diet-induced hyperglycemia.

Tripathy, Sasmita; Torres-Gonzalez, Moises; Jump, Donald B.

2010-01-01

367

Glucose and Fatty Acids Synergize to Promote B-Cell Apoptosis through Activation of Glycogen Synthase Kinase 3? Independent of JNK Activation  

PubMed Central

Background The combination of elevated glucose and free-fatty acids (FFA), prevalent in diabetes, has been suggested to be a major contributor to pancreatic ?-cell death. This study examines the synergistic effects of glucose and FFA on ?-cell apoptosis and the molecular mechanisms involved. Mouse insulinoma cells and primary islets were treated with palmitate at increasing glucose and effects on apoptosis, endoplasmic reticulum (ER) stress and insulin receptor substrate (IRS) signaling were examined. Principal Findings Increasing glucose (5–25 mM) with palmitate (400 µM) had synergistic effects on apoptosis. Jun NH2-terminal kinase (JNK) activation peaked at the lowest glucose concentration, in contrast to a progressive reduction in IRS2 protein and impairment of insulin receptor substrate signaling. A synergistic effect was observed on activation of ER stress markers, along with recruitment of SREBP1 to the nucleus. These findings were confirmed in primary islets. The above effects associated with an increase in glycogen synthase kinase 3? (Gsk3?) activity and were reversed along with apoptosis by an adenovirus expressing a kinase dead Gsk3?. Conclusions/Significance Glucose in the presence of FFA results in synergistic effects on ER stress, impaired insulin receptor substrate signaling and Gsk3? activation. The data support the importance of controlling both hyperglycemia and hyperlipidemia in the management of Type 2 diabetes, and identify pancreatic islet ?-cell Gsk3? as a potential therapeutic target.

Tanabe, Katsuya; Liu, Yang; Hasan, Syed D.; Martinez, Sara C.; Cras-Meneur, Corentin; Welling, Cris M.; Bernal-Mizrachi, Ernesto; Tanizawa, Yukio; Rhodes, Christopher J.; Zmuda, Erik; Hai, Tsonwin; Abumrad, Nada A.; Permutt, M. Alan

2011-01-01

368

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.

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

369

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 3mM 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 0.3mM 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 30mM 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

2013-08-04

370

Thermodynamic study of fatty acids adsorption on different adsorbents  

Microsoft Academic Search

This work has as objective the study about the adsorption behavior of fatty acids (acetic, propionic, and butyric) on activated carbon and on modified and unmodified montmorillonite clays as a function of temperature and initial concentration of the adsorbate, through adsorption isotherms and their thermodynamic parameters (?G, ?H, and ?S). The activated carbon presented a higher adsorption capacity due to

A. F. Freitas; M. F. Mendes; G. L. V. Coelho

2007-01-01

371

Presence of Two Polypeptide Chains Comprising Fatty Acid Synthetase  

Microsoft Academic Search

Highly purified fatty acid synthetases of chicken and rat livers have molecular weights of 500,000 and dissociate in solutions of low ionic strength into subunits of molecular weight 250,000 with loss of synthetase activity. The subunits can be reassociated in phosphate buffer with full restoration of the activity. In the presence of sodium dodecyl sulfate or guanidine HCl, the synthetases

James K. Stoops; Michael J. Arslanian; Yang H. Oh; Kirk C. Aune; Thomas C. Vanaman; Salih J. Wakil

1975-01-01

372

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

2013-06-06

373

Fatty Acid Compositions of Six Wild Edible Mushroom Species  

PubMed Central

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.

Gunc Ergonul, Pelin; Akata, Ilgaz; Kalyoncu, Fatih; Ergonul, Bulent

2013-01-01

374

Hydroxy-Conjugated Fatty Acids.  

National Technical Information Service (NTIS)

This invention relates to a method of producing hydroxy-conjugated octadecadienoic acid from linoleic acid contained in vegetable oils and soap stocks from alkali-refined vegetable oils. Linoleic acid soaps are dispersed in an aqueous medium containing di...

E. A. Emkeu

1973-01-01

375

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...

376

Alpha-fetoprotein-mediated uptake of fatty acids by human T lymphocytes.  

PubMed

The binding to resting and activated T lymphocytes of two radiolabelled fatty acids (oleic and arachidonic) was studied in the presence or in the absence of alpha-fetoprotein (AFP) as carrier protein. Fatty acid binding by resting and activated T lymphocytes was determined at 4 degrees C as a function of the concentration of fatty acid and AFP. Under the conditions employed, the following observations were made: (1) in the presence of AFP, fatty acids (oleic and arachidonic acid) are bound to cells by a two-component pathway; one is a saturable process, evidenced when the fatty acid to AFP (FA/AFP) molar ratio was fixed at 1 and the concentration of the fatty acid and the protein varied from 0.1 to 3.2 microM, and the second is a nonsaturable function of FA/AFP molar ratio and was linearly related to the unbound fatty acid concentration in the medium over the entire range studied; (2) in the absence of AFP, the nonsaturable process appears to be the only component of fatty acid binding; 3) at all tested concentrations of free (unbound) fatty acid in the medium, net fatty acid binding by either resting or activated T cells was considerably greater in the presence than in the absence of AFP; (4) in the presence of AFP, fatty acid binding was much higher in activated T cells than in resting T cells, whereas in the absence of AFP, nonsignificant differences were observed between activated and resting T cells; and (5) the time course of fatty acid and AFP binding at 4 degrees C revealed that, at equilibrium, the number of fatty acid molecules bound to the cell was much greater than that of AFP suggesting an accelerated dissociation of the fatty acid upon interaction of the AFP-fatty acid complex with putative cell receptors. It is concluded to the existence of an AFP/AFP-receptor pathway that facilitates the binding of fatty acids to T lymphocytes, particularly upon their blast transformation. This pathway may fulfill the increased requirement for fatty acids characteristic of proliferating cells and may serve to regulate the endocytosis of fatty acids with modulatory effects on lymphocyte function and to protect cells from their cytotoxic potential when internalized in excess. PMID:1371512

Torres, J M; Anel, A; Uriel, J

1992-03-01

377

INCORPORATION OF BRANCHED-CHAIN FATTY ACIDS INTO MYXOVIRUSES*  

PubMed Central

The incorporation of free fatty acids into myxoviruses was shown, using branched-chain fatty acids as molecular markers. The presence of isostearic or phytanic acid was detected by gas-liquid chromatography in the phospholipid fraction of the A0/PR8/34 strain of influenza virus. Uptake of free fatty acids into the virus varied from 8 to 11 per cent and was accompanied by a shift in the fatty acid profile. Infected allantoic fluids from eggs treated with branched-chain acids possessed higher hemagglutinin activity when compared to fluids infected under normal conditions. Attempts to detect branched-chain acids in Sendai virus were unsuccessful. Shifts in acyl chain composition persisted after three passages of modified viruses in the absence of branched-chain acids. Force-area curves at an air-water interface revealed the cross-sectional area of branched-chain acids to be greater than their straight-chain homologs. It is suggested that hydrophobic interactions can alter the configuration of envelope proteins. Such changes may have an important role in the selection of fragments of influenza viral genome and can conceivably alter viral genotype.

Blough, Herbert A.; Tiffany, John M.

1969-01-01

378

Why does brain metabolism not favor burning of fatty acids to provide energy? - Reflections on disadvantages of the use of free fatty acids as fuel for brain.  

PubMed

It is puzzling that hydrogen-rich fatty acids are used only poorly as fuel in the brain. The long-standing belief that a slow passage of fatty acids across the blood-brain barrier might be the reason. However, this has been corrected by experimental results. Otherwise, accumulated nonesterified fatty acids or their activated derivatives could exert detrimental activities on mitochondria, which might trigger the mitochondrial route of apoptosis. Here, we draw attention to three particular problems: (1) ATP generation linked to ?-oxidation of fatty acids demands more oxygen than glucose, thereby enhancing the risk for neurons to become hypoxic; (2) ?-oxidation of fatty acids generates superoxide, which, taken together with the poor anti-oxidative defense in neurons, causes severe oxidative stress; (3) the rate of ATP generation based on adipose tissue-derived fatty acids is slower than that using blood glucose as fuel. Thus, in periods of extended continuous and rapid neuronal firing, fatty acid oxidation cannot guarantee rapid ATP generation in neurons. We conjecture that the disadvantages connected with using fatty acids as fuel have created evolutionary pressure on lowering the expression of the ?-oxidation enzyme equipment in brain mitochondria to avoid extensive fatty acid oxidation and to favor glucose oxidation in brain. PMID:23921897

Schönfeld, Peter; Reiser, Georg

2013-08-07

379

Fatty acids and early detection of pathogens.  

PubMed

Early in interactions between plants and pathogens, plants recognize molecular signatures in microbial cells, triggering a form of immunity that may help resist infection and colonization by pathogens. Diverse molecules provide these molecular signatures, called pathogen-associated molecular patterns (PAMPs), including proteins, polysaccharides, and lipids. Before and concurrent with the onset of PAMP-triggered immunity, there are alterations in plant membrane lipid composition, modification of membrane fluidity through desaturase-mediated changes in unsaturated fatty acid levels, and enzymatic and non-enzymatic genesis of bioactive lipid mediators such as oxylipins. These complex lipid changes produce a myriad of potential molecular signatures that are beginning to be found to have key roles in the regulation of transcriptional networks. Further, research on fatty acid action in various biological contexts, including plant-pathogen interactions and stress network signaling, is needed to fully understand fatty acids as regulatory signals that transcend their established role in membrane structure and function. PMID:23845737

Walley, Justin W; Kliebenstein, Daniel J; Bostock, Richard M; Dehesh, Katayoon

2013-07-08

380

Effect of fish oils containing different amounts of EPA, DHA, and antioxidants on plasma and brain fatty acids and brain nitric oxide synthase activity in rats  

PubMed Central

Background The interest in n-3 polyunsaturated fatty acids (PUFAs) has expanded significantly in the last few years, due to their many positive effects described. Consequently, the interest in fish oil supplementation has also increased, and many different types of fish oil supplements can be found on the market. Also, it is well known that these types of fatty acids are very easily oxidized, and that stability among supplements varies greatly. Aims of the study In this pilot study we investigated the effects of two different types of natural fish oils containing different amounts of the n-3 PUFAs eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and antioxidants on plasma and brain fatty acids, blood lipids, vitamin E, and in vivo lipid peroxidation, as well as brain nitric oxide synthase (NOS) activity, an enzyme which has been shown to be important for memory and learning ability. Methods Sprague-Dawley rats were divided into four groups and fed regular rat chow pellets enriched with 5% (w/w) of butter (control group), a natural fish oil (17.4% EPA and 11.7% DHA, referred to as EPA-rich), and a natural fish oil rich in DHA (7.7% EPA and 28.0% DHA, referred to as DHA-rich). Both of the fish oils were stabilized by a commercial antioxidant protection system (Pufanox®) at production. The fourth group received the same DHA-rich oil, but without Pufanox® stabilization (referred to as unstable). As an index of stability of the oils, their peroxide values were repeatedly measured during 9 weeks. The dietary treatments continued until sacrifice, after 10 days. Results Stability of the oils varied greatly. It took the two stabilized oils 9 weeks to reach the same peroxide value as the unstable oil reached after only a few days. Both the stabilized EPA- and DHA-rich diets lowered the triacylglycerols and total cholesterol compared to control (-45%, P < 0.05 and -54%, P < 0.001; -31%, P < 0.05 and -25%, P < 0.01) and so did the unstable oil, but less efficiently. Only the unstable oil increased in vivo lipid peroxidation significantly compared to control (+40%, P < 0.001). Most of the fatty acids in the plasma phospholipids were significantly affected by both the EPA- and DHA-rich diets compared to control, reflecting their specific fatty acid pattern. The unstable oil diet resulted in smaller changes, especially in n-3 PUFAs. In the brain phospholipids the changes were less pronounced, and only the diet enriched with the stabilized DHA-rich oil resulted in a significantly greater incorporation of DHA (+13%, P < 0.01), as well as total n-3 PUFAs (+13%, P < 0.01) compared to control. Only the stabilized DHA-rich oil increased the brain NOS activity (+33%, P < 0.01). Conclusions Both the EPA- and DHA-rich diets affected the blood lipids in a similarly positive manner, and they both had a large impact on plasma phospholipid fatty acids. It was only the unstable oil that increased in vivo lipid peroxidation. However, the intake of DHA was more important than that of EPA for brain phospholipid DHA enrichment and brain NOS activity, and the stability of the fish oil was also important for these effects.

Engstrom, Karin; Saldeen, Ann-Sofie; Yang, Baichun; Mehta, Jawahar L.

2009-01-01

381

Polyhydroxy Fatty Acids Derived from Sophorolipids  

Microsoft Academic Search

Starting from 17-hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy\\u000a fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other\\u000a functional groups. The added hydroxy groups can be incorporated in the C18 chain in a variety of geometries, for example spaced widely throughout the

Jonathan A. Zerkowski; Daniel K. Y. Solaiman

2007-01-01

382

Essential fatty acid transfer and fetal development  

Microsoft Academic Search

Docosahexaenoic acid (22:6n-3) and arachidonic acid (20:4n-6) are important structural components of the central nervous system. These fatty acids are transferred across the placenta, and are accumulated in the brain and other organs during fetal development. Depletion of 22:6n-3 from the retina and brain results in reduced visual function and learning deficits: these may involve critical roles of 22:6n-3 in

S. M. Innis

2005-01-01

383

The effect of n-3 long chain fatty acids supplementation on plasma peroxisome proliferator activated receptor gamma and thyroid hormones in obesity  

PubMed Central

Background: Peroxisome proliferator-activated receptor gamma (PPAR ?) is a transcription factor, which is abundantly expressed in adipose tissue and has a direct link to adiposity. It seems that long-chain polyunsaturated fatty acids (LC-PUFAs) can regulate PPAR ? expression. The purpose of this study was to investigate the effects of n-3LC PUFA supplementation on plasma levels of PPAR ? and thyroid hormones in obesity. Materials and Methods: In a randomized double-blind controlled trial, 66 subjects with obesity were assigned to 2 groups. Participants in intervention group consumed omega3 capsules contained 1000 mg n-3 fatty acids (180 mg of eicosapentaenoic acid [EPA] and 120 mg of docosahexaenoic acid [DHA]) and placebo group consumed placebo capsules contained paraffin twice a day for 4 wk. Fasting blood samples and weight measurements were collected at the baseline and at the end of the trial. Plasma PPAR ? and thyroid hormones were measured by ELISA. Data were analyzed using a repeated measure model-two factor for comparing two groups in two times. Results: No significant changes were observed in PPAR ? levels between and within the groups after supplementation (P>0.05). N-3LC PUFA supplementation significantly increased T4 levels after 4 wk (P<0.05) but T3 and TSH did not change significantly. Conclusion: Our study showed that n-3LC PUFAs supplementation increased T4 levels. However, no significant changes in T3, TSH and PPAR ? plasma levels were observed in obese adults.

Taraghijou, Parizad; Safaeiyan, Abdolrasoul; Mobasseri, Majid; Ostadrahimi, Alireza

2012-01-01

384

Changes in fatty acid composition and degree of unsaturation of (brady)rhizobia as a response to phases of growth, reduced water activities and mild desiccation.  

PubMed

The effects of growth phase, reductions in the water activity (a(w)) of the growth medium and mild desiccation on the composition and the degree of unsaturation of cellular fatty acids (CFA) of Sinorhizobium meliloti, Bradyrhizobium elkanii and Bradyrhizobium japonicum were studied. During the course of growth, an interchange of cis-vaccenic with lactobacillic acid and a slight increase in palmitic acid were observed while other fatty acids remained constant. The degree of unsaturation was significantly higher in the exponential phase of growth. Reductions in the a(w) of the medium led to an increase in lag phase, a reduction in growth rate and maximal optical densities (OD) in stationary phase cells. A decrease in the degree of unsaturation of CFA was also observed as the a(w) was reduced from 0.999 to 0.969 and after desiccation to 83.5% relative humidity (R.H.). The changes in the degree of unsaturation of CFA observed after growth at reduced a(w) may be one of the pre-adaptation steps to endure more severe desiccation. PMID:11392487

Boumahdi, M; Mary, P; Hornez, J P

2001-01-01

385

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

PubMed

Intestinal fatty acid binding protein (IFABP) is thought to participate in the intracellular transport of fatty acids (FAs). Fatty acid transfer from IFABP to phospholipid membranes is proposed to occur during protein-membrane collisional interactions. In this study, we analyzed the participation of electrostatic and hydrophobic interactions in the collisional mechanism of FA transfer from IFABP to membranes. Using a fluorescence resonance energy transfer assay, we examined the rate and mechanism of transfer of anthroyloxy-fatty acid analogs a) from IFABP to phospholipid membranes of different composition; b) from chemically modified IFABPs, in which the acetylation of surface lysine residues eliminated positive surface charges; and c) as a function of ionic strength. The results show clearly that negative charges on the membrane surface and positive charges on the protein surface are important for establishing the "collisional complex", during which fatty acid transfer occurs. In addition, changes in the hydrophobicity of the protein surface, as well as the hydrophobic volume of the acceptor vesicles, also influenced the rate of fatty acid transfer. Thus, ionic interactions between IFABP and membranes appear to play a primary role in the process of fatty acid transfer to membranes, and hydrophobic interactions can also modulate the rates of ligand transfer. PMID:15863832

Córsico, Betina; Franchini, Gisela R; Hsu, Kuo-Tung; Storch, Judith

2005-05-01

386

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

Microsoft Academic Search

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

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

2006-01-01

387

Cyclopropenoid fatty acid content and fatty acid composition of crude cottonseed oils from successive solvent extractions  

Microsoft Academic Search

The fatty acid composition and properties of six fractions of oil successively extracted from cottonseed meats has been investigated.\\u000a The cyclopropenoid fatty acid concn increased regularly from 0.30–1.06%, a 3.5-fold increase. This suggests that the cyclopropenoid\\u000a constituents of the oil in the seed are less accessible to the solvent. The linoleic acid concn decreased from 56.3–53.1%\\u000a accounting for a slight

A. V. Bailey; W. A. Pons; E. L. Skau

1965-01-01

388

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

389

Free fatty acid-induced muscle insulin resistance and glucose uptake dysfunction: Evidence for PKC activation and oxidative stress-activated signaling pathways  

PubMed Central

In the present study, we examined the effects of free fatty acids (FFAs) on insulin sensitivity and signaling cascades in the C2C12 skeletal muscle cell culture system. Our data clearly manifested that the inhibitory effects of PKC on insulin signaling may at least in part be explained by the serine/threonine phosphorylation of IRS-1. Both oleate and palmitate treatment were able to increase the Serine307 phosphorylation of IRS-1. IRS-1 Serine307 phosphorylation is inducible which causes the inhibition of IRS-1 tyrosine phosphorylation by either I?B-kinase (IKK) or c-jun N-terminal kinase (JNK) as seen in our proteomic kinases screen. Furthermore, our proteomic data have also manifested that the two FFAs activate the IKK?/?, the stress kinases S6 kinase p70 (p70SK), stress-activated protein kinase (SAPK), JNK, as well as p38 MAP kinase (p38MAPK). On the other hand, the antioxidant, Taurine at 10 mM concentrations was capable of reversing the oleate-induced insulin resistance in myocytes as manifested from the glucose uptake data. Our current data point out the importance of FFA-induced insulin resistance via multiple signaling mechanisms.

Ragheb, Rafik; Shanab, Gamila M.L.; Medhat, Amina M.; Seoudi, Dina M.; Adeli, K.; Fantus, I.G.

2010-01-01

390

Polyunsaturated fatty acid production by marine bacteria.  

PubMed

Polyunsaturated fatty acids are important in maintaining human health. Limitations associated with current sources of ?-3 fatty acids and ?-6 fatty acids, from animal and plant sources, have led to increased interest in microbial production. Marine bacteria may provide a suitable alternative, although the isolation of production strains and the identification of operating conditions must be addressed before manufacturing processes become economically viable. Marine isolate 560 was identified as an eicosapentaenoic acid (EPA) producer via GC/MS. The isolate was initially identified as Vibrio cyclitrophicus by 16S rRNA sequencing. Statistically based experimental designs were applied to the optimisation of medium components and environmental factors for the production of EPA. A Plackett-Burman design was used to screen for the effect of temperature, pH, and media components. Subsequently, the concentrations of NaCl, yeast extract, and peptone, identified as significant factors, were optimised using a central composite design. The predicted optimal combination of media components for maximum EPA production (4.8 mg/g dry weight) was determined as 7.9 g/l peptone, 16.2 g/l NaCl, and 6.2 g/l yeast extract. On transfer of this process to bioreactor cultivation, where a range of pH and DO values were tested, the maximum amount of EPA produced increased to 7.5 mg/g dry weight and 10 % of the total fatty acid. PMID:23525832

Abd Elrazak, Ahmed; Ward, Alan C; Glassey, Jarka

2013-03-23

391

Omega-3 Fatty Acids from Fish Oil Lower Anxiety, Improve Cognitive Functions and Reduce Spontaneous Locomotor Activity in a Non-Human Primate  

PubMed Central

Omega-3 (?3) polyunsaturated fatty acids (PUFA) are major components of brain cells membranes. ?3 PUFA-deficient rodents exhibit severe cognitive impairments (learning, memory) that have been linked to alteration of brain glucose utilization or to changes in neurotransmission processes. ?3 PUFA supplementation has been shown to lower anxiety and to improve several cognitive parameters in rodents, while very few data are available in primates. In humans, little is known about the association between anxiety and ?3 fatty acids supplementation and data are divergent about their impact on cognitive functions. Therefore, the development of nutritional studies in non-human primates is needed to disclose whether a long-term supplementation with long-chain ?3 PUFA has an impact on behavioural and cognitive parameters, differently or not from rodents. We address the hypothesis that ?3 PUFA supplementation could lower anxiety and improve cognitive performances of the Grey Mouse Lemur (Microcebus murinus), a nocturnal Malagasy prosimian primate. Adult male mouse lemurs were fed for 5 months on a control diet or on a diet supplemented with long-chain ?3 PUFA (n?=?6 per group). Behavioural, cognitive and motor performances were measured using an open field test to evaluate anxiety, a circular platform test to evaluate reference spatial memory, a spontaneous locomotor activity monitoring and a sensory-motor test. ?3-supplemented animals exhibited lower anxiety level compared to control animals, what was accompanied by better performances in a reference spatial memory task (80% of successful trials vs 35% in controls, p<0.05), while the spontaneous locomotor activity was reduced by 31% in ?3-supplemented animals (p<0.001), a parameter that can be linked with lowered anxiety. The long-term dietary ?3 PUFA supplementation positively impacts on anxiety and cognitive performances in the adult mouse lemur. The supplementation of human food with ?3 fatty acids may represent a valuable dietary strategy to improve behavioural and cognitive functions.

Vinot, Nina; Jouin, Melanie; Lhomme-Duchadeuil, Adrien; Guesnet, Philippe; Alessandri, Jean-Marc; Aujard, Fabienne; Pifferi, Fabien

2011-01-01

392

Antineoplastic unsaturated fatty acids from Fijian macroalgae  

Microsoft Academic Search

Phytochemical analysis of Fijian populations of the green alga Tydemania expeditionis led to the isolation of two 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 glycolipid, lithonoside (3), and five known compounds, 15-tricosenoic acid, hexacosa-5,9-dienoic methyl ester, ?-sitosterol, 10(S)-hydroxypheophytin

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

2008-01-01

393

Flaxseed supplementation improves fatty acid profile of cow milk.  

PubMed

The objective of the study was to determine the effects of adding flaxseed or fish oil to the diet on the milk fatty acid profile of cows. The experiment was conducted in the summer of 2006 and involved 24 Friesian cows that were divided into 3 groups of 8 animals according to different type of fat supplementation: a traditional diet with no fat supplementation, a diet supplemented with whole flaxseed, and a diet supplemented with fish oil. Results suggested that whole flaxseed supplementation positively affects the milk fatty acid profile during summer. In particular, milk from cows receiving flaxseed supplementation showed a decrease in saturated fatty acid, an increase in monounsaturated fatty acid, and, together with the milk from fish oil-supplemented cows, an increase in polyunsaturated fatty acid content compared with milk from control cows. As expected, both fish oil and flaxseed supplementation increased the content of n-3 polyunsaturated fatty