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1

Original article Antimicrobial activity of fatty acids  

E-print Network

. For example, while myr- istic acid (14:0) was only slightly active (10 mm inhibition zone), myristoleic acidOriginal article Antimicrobial activity of fatty acids against Bacillus larvae, the causative agent and unsaturated free fatty acids were tested for their antibiotic activ- ity against Bacillus larvae

Paris-Sud XI, Université de

2

Antioxidant and cyclooxygenase activities of fatty acids found in food.  

PubMed

Several commercially available C-8 to C-24 saturated and unsaturated fatty acids (1-29) were assayed for cyclooxygenase-I (COX-I) and cyclooxygenase-II (COX-II) inhibitory and antioxidant activities. Among the saturated fatty acids tested at 60 microg mL(-1), there was an increase in antioxidant activity with increasing chain length from octanoic acid to myristic acid (C-8-C-14) and a decrease thereafter. All unsaturated fatty acids tested at 60 microg mL(-1) showed good antioxidant activity except for undecylenic acid (12), cis-5-dodecenoic acid (13), and nervonic acid (29). The highest inhibitory activities among the saturated fatty acids tested on cyclooxygenase enzymes COX-I and COX-II were observed for decanoic acid to lauric acid (3-5) at 100 microg mL(-1). Similarly, among the unsaturated fatty acids tested, the highest activities were observed for cis-8,11,14-eicosatrienoic acid (25) and cis-13,16-docosadienoic acid (27) at 100 microg mL(-1). PMID:11929276

Henry, Geneive E; Momin, Rafikali A; Nair, Muraleedharan G; Dewitt, David L

2002-04-10

3

Peroxisomal and Mitochondrial Fatty Acid -Oxidation in Mice Nullizygous for Both Peroxisome Proliferator-activated  

E-print Network

Peroxisomal and Mitochondrial Fatty Acid -Oxidation in Mice Nullizygous for Both Peroxisome Proliferator-activated Receptor and Peroxisomal Fatty Acyl-CoA Oxidase GENOTYPE CORRELATION WITH FATTY LIVER 20892 Fatty acid -oxidation occurs in both mitochondria and peroxisomes. Long chain fatty acids are also

Omiecinski, Curtis

4

Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase  

Microsoft Academic Search

The effects of fatty acids, octanoic acid, (2E, 4E)-hexa-2,4-dienoic acid, hexanoic acid, (2E)-but-2-enoic acid, and butyric acid on the activities of mushroom tyrosinase have been investigated. The results showed that\\u000a the fatty acids can potently inhibit both monophenolase activity and diphenolase activity of tyrosinase, and that the unsaturated\\u000a fatty acids exhibited stronger inhibitory effect against tyrosinase than the corresponding saturated

Yun-Ji Guo; Zhi-Zhen Pan; Chao-Qi Chen; Yong-Hua Hu; Feng-Jiao Liu; Yan Shi; Jiang-Hua Yan; Qing-Xi Chen

2010-01-01

5

Analysis of fatty acid amide hydrolase activity in plants.  

PubMed

N-Acylethanolamines (NAEs) are fatty acid derivatives amide-linked to ethanolamine. NAEs vary in chain lengths and numbers of double bonds and generally reflect the fatty acids found in membrane lipids in the tissues in which they reside. NAEs are present naturally in trace amounts and occur in a wide range of organisms including plants, animals, and microbes. Some NAE types are known to be involved in the endocannabinoid signaling system of vertebrates, and in plants they may play important regulatory roles in several physiological processes, such as root growth, seedling development, stress responses, and pathogen interactions. The biological effects of NAEs are terminated through their hydrolysis into the ethanolamine and free fatty acid by a membrane enzyme known as the fatty acid amide hydrolase (FAAH). Thus, FAAH represents an important target to better understand the function of these lipid mediators in numerous cellular processes. FAAH has been extensively characterized in mammalian and plant systems, and they share a conserved Ser-Ser-Lys catalytic mechanism. Here we describe procedures and experimental conditions to assay and characterize recombinant and endogenous FAAH enzymatic activity derived from plant tissues. PMID:23681529

Kim, Sang-Chul; Faure, Lionel; Chapman, Kent D

2013-01-01

6

Saturated fatty acids activate TLR-mediated proinflammatory signaling pathways.  

PubMed

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. PMID:22766885

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

2012-09-01

7

Fatty Acid-Elongating Activity in Rapidly Expanding Leek Epidermis.  

PubMed Central

A microsomal fatty acid elongase activity measured in epidermis of rapidly expanding leek (Allium porrum L.) was 10-fold higher in specific activity than preparations from store-bought leek. These preparations elongated acyl chains effectively using endogenous or supplied primers. Elongation of C20:0 was specifically inhibited by 2 [mu]M cerulenin, and labeling experiments with [3H]cerulenin labeled two polypeptides (65 and 88 kD). ATP was required for maximal elongase activity in expanding leaves but was lost in nonexpanding tissues. Both [14C]stearoyl-coenzyme A (CoA) and [14C]stearate were maximally elongated in the presence of ATP. Addition of fully reduced CoA, however, inhibited [14C]stearate elongation, suggesting that stearoyl-CoA synthesis was not a prerequisite for elongation. Furthermore, microsomes preincubated with [14C]stearoyl-CoA plus ATP resulted in loss of radiolabel from the acyl-CoA pool without a corresponding loss in elongating activity. The lack of correlation between elongating activity and the label retained in the putative acyl-CoA substrate pool suggests that acyl-CoAs may not be the immediate precursors for elongation and that ATP plays a critical, yet undefined, role in the elongation process. We propose that an ATP-dependent elongating activity may generate the long-chain fatty acids required for wax biosynthesis. PMID:12228624

Evenson, K. J.; Post-Beittenmiller, D.

1995-01-01

8

Mechanistic and functional insights into fatty acid activation in Mycobacterium tuberculosis  

Microsoft Academic Search

The recent discovery of fatty acyl-AMP ligases (FAALs) in Mycobacterium tuberculosis (Mtb) provided a new perspective of fatty acid activation. These proteins convert fatty acids to the corresponding adenylates, which are intermediates of acyl-CoA–synthesizing fatty acyl-CoA ligases (FACLs). Presently, it is not evident how obligate pathogens such as Mtb have evolved such new themes of functional versatility and whether the

Pooja Arora; Aneesh Goyal; Vivek T Natarajan; Eerappa Rajakumara; Priyanka Verma; Radhika Gupta; Malikmohamed Yousuf; Omita A Trivedi; Debasisa Mohanty; Anil Tyagi; Rajan Sankaranarayanan; Rajesh S Gokhale

2009-01-01

9

A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs  

Microsoft Academic Search

Fatty acids, which are essential nutritional components, are also involved in cardiovascular and metabolic diseases. Here we report a human cell surface receptor that we name free fatty acid receptor (FFAR), because it is specifically activated by medium to long-chain free fatty acids. The receptor belongs to the class of seven-transmembrane, G-protein coupled receptors (GPCRs) and also mediates responses to

Knut Kotarsky; Niclas E. Nilsson; Erik Flodgren; Christer Owman; Björn Olde

2003-01-01

10

Mammalian Fatty Acid Elongases  

PubMed Central

Summary Very long chain fatty acids confer functional diversity on cells by variations in their chain length and degree of unsaturation. Microsomal fatty acid elongation represents the major pathway for determining the chain length of saturated, monounsaturated, and polyunsaturated fatty acids in cellular lipids. The overall reaction for fatty acid elongation involves four enzymes and utilizes malonyl CoA, NADPH, and fatty acyl CoA as substrates. While the fundamental pathway and its requirements have been known for many years, recent advances have revealed a family of enzymes involved in the first step of the reaction, i.e., the condensation reaction. Seven fatty acid elongase subtypes (Elovl #1–7) have been identified in the mouse, rat, and human genomes. These enzymes determine the rate of overall fatty acid elongation. Moreover, these enzymes also display differential substrate specificity, tissue distribution, and regulation, making them important regulators of cellular lipid composition as well as specific cellular functions. Herein, methods are described to measure elongase activity, analyze elongation products, and alter cellular elongase expression. PMID:19763486

Jump, Donald B.

2009-01-01

11

Mapping human brain fatty acid amide hydrolase activity with PET  

PubMed Central

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

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

2013-01-01

12

Expression of Putative Fatty Acid Transporter Genes Are Regulated by Peroxisome Proliferator-activated Receptor  

E-print Network

Expression of Putative Fatty Acid Transporter Genes Are Regulated by Peroxisome Proliferator (mAspAT), and fatty acid transport protein (FATP), by drugs that activate peroxisome proliferator course in the liver was slower for FAT and FATP mRNA than that of an mRNA encoding a peroxisomal enzyme

Omiecinski, Curtis

13

Effect of pasteurization on long chain polyunsaturated fatty acid levels and enzyme activities of human milk  

Microsoft Academic Search

Milk fatty acids, including the polyunsaturated long chain fatty acids essential for retinal function and brain development, are not affected by pasteurization (62.5° C for 30 min). Milk lipases are completely destroyed by pasteurization, whereas amylase lost only 15% of initial activity. Thus, certain bioactive components are stable to pasteurization of donor milk and can benefit the recipient infants. (J

Theresa R. Henderson; Terese N. Fay; Margit Hamosh

1998-01-01

14

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. PMID:24167374

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

2013-01-01

15

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

16

Significant inverse associations of serum n-6 fatty acids with plasma plasminogen activator inhibitor-1  

PubMed Central

Objective Epidemiological studies suggested that n-6 fatty acids, especially linoleic acid (LA), have beneficial effects on coronary heart disease (CHD), whereas some in vitro studies suggested that n-6 fatty acids, specifically arachidonic acid (AA), may have harmful effects. We examined the association of serum n-6 fatty acids with plasminogen activator inhibitor-1 (PAI-1). Methods and Results A population-based cross-sectional study recruited 926 randomly selected men aged 40–49 without cardiovascular disease during 2002 to 2006 (310 Caucasian, 313 Japanese, and 303 Japanese-American men). Plasma PAI-1 was analyzed in free form, both active and latent. Serum fatty acids were measured with gas-capillary-liquid-chromatography. To examine the association between total n-6 fatty acids (including LA and AA, respectively) and PAI-1, multivariate regression models were used. After adjusting for confounders, total n-6 fatty acids, LA, and AA were inversely and significantly associated with PAI-1 levels. These associations were consistent across three populations. Conclusions Among 915 middle-aged men, serum n-6 fatty acids had significant inverse associations with PAI-1. PMID:21846428

Lee, Sunghee; Curb, J. David; Kadowaki, Takashi; Evans, Rhobert W.; Miura, Katsuyuki; Takamiya, Tomoko; Shin, Chol; El-Saed, Aiman; Choo, Jina; Fujiyoshi, Akira; Otake, Teruo; Kadowaki, Sayaka; Seto, Todd; Masaki, Kamal; Edmundowicz, Daniel; Ueshima, Hirotsugu; Kuller, Lewis H.; Sekikawa, Akira

2011-01-01

17

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

18

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

PubMed Central

Since the first fatty acid amino acid conjugate (FAC) was isolated from regurgitant of Spodoptera exigua larvae in 1997 [volicitin: N-(17-hydroxylinolenoyl)-l-glutamine], their role as elicitors of induced responses in plants has been well documented. However, studies of the biosyntheses and the physiological role of FACs in the insect have been minimal. By using 14C-labeled glutamine, glutamic acid, and linolenic acid in feeding studies of Spodoptera litura larvae, combined with tissue analyses, we found glutamine in the midgut cells to be a major source for biosynthesis of FACs. Furthermore, 20% of the glutamine moiety of FACs was derived from glutamic acid and ammonia through enzymatic reaction of glutamine synthetase (GS). To determine whether FACs improve GS productivity, we studied nitrogen assimilation efficiency of S. litura larvae fed on artificial diets containing 15NH4Cl and glutamic acid. When the diet was enriched with linolenic acid, the nitrogen assimilation efficiency improved from 40% to >60%. In the lumen, the biosynthesized FACs are hydrolyzed to fatty acids and glutamine, which are reabsorbed into tissues and hemolymph. These results strongly suggested that FACs play an active role in nitrogen assimilation in Lepidoptera larva and that glutamine containing FACs in the gut lumen may function as a form of storage of glutamine, a key compound of nitrogen metabolism. PMID:18997016

Yoshinaga, Naoko; Aboshi, Takako; Abe, Hiroaki; Nishida, Ritsuo; Alborn, Hans T.; Tumlinson, James H.; Mori, Naoki

2008-01-01

19

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

20

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

PubMed

Fatty acid synthase is over-expressed in many cancers and its activity is required for cancer cell survival, but the role of endogenously synthesized fatty acids in cancer is unknown. It has been suggested that endogenous fatty acid synthesis is either needed to support the growth of rapidly dividing cells, or to maintain elevated glycolysis (the Warburg effect) that is characteristic of cancer cells. Here, we investigate both hypotheses. First, we compared utilization of fatty acids synthesized endogenously from (14)C-labeled acetate to those supplied exogenously as (14)C-labeled palmitate in the culture medium in human breast cancer (MCF-7 and MDA-MB-231) and untransformed breast epithelial cells (MCF-10A). We found that cancer cells do not produce fatty acids that are different from those derived from exogenous palmitate, that these fatty acids are esterified to the same lipid and phospholipid classes in the same proportions, and that their distribution within neutral lipids is not different from untransformed cells. These results suggest that endogenously synthesized fatty acids do not fulfill a specific function in cancer cells. Furthermore, we observed that cancer cells excrete endogenously synthesized fatty acids, suggesting that they are produced in excess of requirements. We next investigated whether lipogenic activity is involved in the maintenance of high glycolytic activity by culturing both cancer and non-transformed cells under anoxic conditions. Although anoxia increased glycolysis 2-3 fold, we observed no concomitant increase in lipogenesis. Our results indicate that breast cancer cells do not have a specific qualitative or quantitative requirement for endogenously synthesized fatty acids and that increased de novo lipogenesis is not required to sustain elevations in glycolytic activity induced by anoxia in these cells. PMID:24200503

Hopperton, Kathryn E; Duncan, Robin E; Bazinet, Richard P; Archer, Michael C

2014-01-15

21

Free fatty acids and protein kinase C activation induce GPR120 (free fatty acid receptor 4) phosphorylation.  

PubMed

GPR120, free fatty acid receptor 4, is a recently deorphanized G protein-coupled receptor that seems to play cardinal roles in the regulation of metabolism and in the pathophysiology of inflammatory and metabolic disorders. In the present work a GPR120-Venus fusion protein was expressed in HEK293 Flp-In T-REx cells and its function (increase in intracellular calcium) and phosphorylation were studied. It was observed that the fusion protein migrated in sodium dodecyl sulfate-polyacrylamide gels as a band with a mass of ?70-75kDa, although other bands of higher apparent weight (>130kDa) were also detected. Cell stimulation with docosahexaenoic acid or ?-linolenic acid induced concentration-dependent increases in intracellular calcium and GPR120 phosphorylation. Activation of protein kinase C with phorbol esters also induced a marked receptor phosphorylation but did not alter the ability of 1µM docosahexaenoic acid to increase the intracellular calcium concentration. Phorbol ester-induced GPR120 phosphorylation, but not that induced with docosahexaenoic acid, was blocked by protein kinase C inhibitors (bis-indolyl-maleimide I and Gö 6976) suggesting that conventional kinase isoforms mediate this action. The absence of effect of protein kinase C inhibitors on agonist-induced GPR120 phosphorylation indicates that this kinase does not play a major role in agonist-induced receptor phosphorylation. Docosahexaenoic acid action was associated with marked GPR120 internalization whereas that induced with phorbol esters was smaller at early times. PMID:24239485

Sánchez-Reyes, Omar B; Romero-Ávila, M Teresa; Castillo-Badillo, Jean A; Takei, Yoshinori; Hirasawa, Akira; Tsujimoto, Gozoh; Villalobos-Molina, Rafael; García-Sáinz, J Adolfo

2014-01-15

22

Fatty acid analogs  

DOEpatents

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

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

1985-01-01

23

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

24

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

25

Phytanic acid is ligand and transcriptional activator of murine liver fatty acid binding protein  

Microsoft Academic Search

Branched-chain phytanic acid is metabolized in liver peroxisomes. Sterol carrier protein 2\\/sterol carrier protein x (SCP2\\/SCPx) knockout mice, which develop a phenotype with a deficiency in phytanic acid degradation, accumulate dramatically high concentrations of this fatty acid in serum (Seedorf at al. 1998. Genes Dev. 12: 1189- 1201) and liver. Concomitantly, a 6.9-fold induction of liver fatty acid binding protein

Christian Wolfrum; Peter Ellinghaus; Manfred Fobker; Udo Seedorf; Gerd Assmann; Torsten Börchers; Friedrich Spener

26

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

27

Omega-3 fatty acid deficiency selectively up-regulates delta6-desaturase expression and activity indices in rat liver: prevention by normalization of omega-3 fatty acid status.  

PubMed

This study investigated the effects of perinatal dietary omega-3 (n-3) fatty acid depletion and subsequent repletion on the expression of genes that regulate long-chain (LC) polyunsaturated fatty acid biosynthesis in rat liver and brain. It was hypothesized that chronic n-3 fatty acid deficiency would increase liver Fads1 and Fads2 messenger RNA (mRNA) expression/activity and that n-3 fatty acid repletion would normalize this response. Adult rats fed the n-3-free diet during perinatal development exhibited significantly lower erythrocyte, liver, and frontal cortex LCn-3 fatty acid composition and reciprocal elevations in LC omega-6 (n-6) fatty acid composition compared with controls (CONs) and repleted rats. Liver Fads2, but not Fads1, Elovl2, or Elovl5, mRNA expression was significantly greater in n-3-deficient (DEF) rats compared with CONs and was partially normalized in repleted rats. The liver 18:3n-6/18:2n-6 ratio, an index of delta6-desturase activity, was significantly greater in DEF rats compared with CON and repleted rats and was positively correlated with Fads2 mRNA expression among all rats. The liver 18:3n-6/18:2n-6 ratio, but not Fads2 mRNA expression, was also positively correlated with erythrocyte and frontal cortex LCn-6 fatty acid compositions. Neither Fads1 or Fads2 mRNA expression was altered in brain cortex of DEF rats. These results confirm previous findings that liver, but not brain, delta6-desaturase expression and activity indices are negatively regulated by dietary n-3 fatty acids. PMID:22024496

Hofacer, Rylon; Jandacek, Ronald; Rider, Therese; Tso, Patrick; Magrisso, I Jack; Benoit, Stephen C; McNamara, Robert K

2011-09-01

28

Fatty Acid Accumulation and Resulting PPAR? Activation in Fibroblasts due to Trifunctional Protein Deficiency  

PubMed Central

To examine fatty acid accumulation and its toxic effects in cells, we analyzed skin fibroblasts from six patients with mitochondrial trifunctional protein deficiency, who had abnormalities in the second through fourth reactions in fatty acid ?-oxidation system. We found free fatty acid accumulation, enhanced three acyl-CoA dehydrogenases, catalyzing the first reaction in the ?-oxidation system and being assumed to have normal activities in these patients, and PPAR? activation that was confirmed in the experiments using MK886, a PPAR? specific antagonist and fenofibrate, a PPAR? specific agonist. These novel findings suggest that the fatty acid accumulation and the resulting PPAR? activation are major causes of the increase in the ?-oxidation ability as probable compensation for fatty acid metabolism in the patients' fibroblasts, and that enhanced cell proliferation and increased oxidative stress due to the PPAR? activation relate to the development of specific clinical features such as hypertrophic cardiomyopathy, slight hepatomegaly, and skeletal myopathy. Additionally, significant suppression of the PPAR? activation by means of MK886 treatment is assumed to provide a new method of treating this deficiency. PMID:22654897

Wakabayashi, Masato; Kamijo, Yuji; Nakajima, Takero; Tanaka, Naoki; Sugiyama, Eiko; Yangyang, Tian; Kimura, Takefumi; Aoyama, Toshifumi

2012-01-01

29

Fatty Acids Homeostasis; the search for  

E-print Network

Schizophrenia Bipolar and attention deficit hyperactivityBipolar and attention deficit hyperactivity DepressionDepression Mood disordersMood disorders #12;Activation of Fatty AcidActivation of Fatty Acid Synthetase transcriptional activityFatty Acids affect NR transcriptional activity What are genetic responses to the alteredWhat

Knyazev, Andrew

30

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

PubMed Central

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

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

2012-01-01

31

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

32

Microbicidal activity of tripotassium phosphate and fatty acids toward spoilage and pathogenic bacteria associated with poultry.  

PubMed

The ability of solutions of tripotassium phosphate (TPP) and fatty acids (lauric and myristic acids) to reduce populations of spoilage and pathogenic microorganisms associated with processed poultry was examined. In vitro studies were conducted with cultures of bacteria (Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, Pseudomonas aeruginosa, Salmonella Typhimurium, and Staphylococcus aureus) and yeasts (Candida ernobii and Yarrowia lipolytica). Cultures of the bacteria and yeasts were suspended in solutions of TPP or mixtures of TPP with lauric or myristic acid and mixed for 5 min. Viable numbers (log CFU per milliliter) in the suspensions were enumerated on microbiological agar. Results indicated that TPP solutions are highly bactericidal toward gram-negative bacteria and that mixtures of TPP and fatty acids are highly microbicidal toward gram-negative bacteria, gram-positive bacteria, and yeasts. The microbicidal activity of mixtures of TPP and fatty acids toward the native bacterial flora of skin of processed broiler carcasses was also examined. Skin samples were washed in mixtures of TPP and fatty acid, and the populations of total aerobic bacteria, campylobacters, enterococci, E. coli, lactic acid bacteria, pseudomonads, staphylococci, and yeasts in the skin rinsates were enumerated on the appropriate microbiological media. Results indicated that washing the skin in mixtures of TPP and fatty acids produced significant reductions in the number of aerobic bacteria, campylobacters, E. coli, pseudomonads, and yeasts recovered from skin rinsates, but there was no significant reduction in the populations of enterococci, lactic acid bacteria, or staphylococci. These findings indicate that mixtures of TPP and fatty acids possess microbicidal activity against several microorganisms associated with processed poultry and that these solutions could be useful as microbicides to reduce the populations of some bacteria and yeasts associated with some poultry processing operations. PMID:16013388

Hinton, Arthur; Ingram, Kimberly D

2005-07-01

33

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

PubMed

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

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

2013-12-01

34

Omega-3 fatty acids moderate effects of physical activity on cognitive function.  

PubMed

Greater amounts of physical activity (PA) and omega-3 fatty acids have both been independently associated with better cognitive performance. Because of the overlapping biological effects of omega-3 fatty acids and PA, fatty acid intake may modify the effects of PA on neurocognitive function. The present study tested this hypothesis by examining whether the ratio of serum omega-6 to omega-3 fatty acid levels would moderate the association between PA and executive and memory functions in 344 participants (Mean age=44.42 years, SD=6.72). The Paffenbarger Physical Activity Questionnaire (PPAQ), serum fatty acid levels, and performance on a standard neuropsychological battery were acquired on all subjects. A principal component analysis reduced the number of cognitive outcomes to three factors: n-back working memory, Trail Making test, and Logical Memory. We found a significant interaction between PA and the ratio of omega-6 to omega-3 fatty acid serum levels on Trail Making performance and n-back performance, such that higher amounts of omega-3 levels offset the deleterious effects of lower amounts of PA. These effects remained significant in a subsample (n=299) controlling for overall dietary fat consumption. There were no significant additive or multiplicative benefits of higher amounts of both omega-3 and PA on cognitive performance. Our results demonstrate that a diet high in omega-3 fatty acids might mitigate the effect of lower levels of PA on cognitive performance. This study illuminates the importance of understanding dietary and PA factors in tandem when exploring their effects on neurocognitive health. PMID:24813150

Leckie, Regina L; Manuck, Stephen B; Bhattacharjee, Neha; Muldoon, Matthew F; Flory, Janine M; Erickson, Kirk I

2014-07-01

35

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

Microsoft Academic Search

This work demonstrates that spermatozoa from five avian species (chicken, turkey, guinea fowl, duck and goose) are all characterised by high proportions of polyunsaturated fatty acids, from 46 (turkey) to 55% (duck) of total. For each of the species, the most abundant fatty acids were arachidonic (20:4n–6) and docosatetraenoic (22:4n–6) acids, representing between 22 (turkey) and 40% (chicken) of total.

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

1998-01-01

36

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. PMID:20548930

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

2010-01-01

37

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

E-print Network

A FAD2 homologue from Lesquerella lindheimeri has predominantly fatty acid hydroxylase activity Abstract A genomic sequence encoding a polypeptide with 91% sequence identity to the Lesquerella fendleri bifunctional oleate 12-hydroxylase:- desaturase was amplified by PCR from Lesquerella lindheimeri. Expression

Kunst, Ljerka

38

VASP Increases Hepatic Fatty Acid Oxidation by Activating AMPK in Mice  

PubMed Central

Activation of AMP-activated protein kinase (AMPK) signaling reduces hepatic steatosis and hepatic insulin resistance; however, its regulatory mechanisms are not fully understood. In this study, we sought to determine whether vasodilator-stimulated phosphoprotein (VASP) signaling improves lipid metabolism in the liver and, if so, whether VASP’s effects are mediated by AMPK. We show that disruption of VASP results in significant hepatic steatosis as a result of significant impairment of fatty acid oxidation, VLDL-triglyceride (TG) secretion, and AMPK signaling. Overexpression of VASP in hepatocytes increased AMPK phosphorylation and fatty acid oxidation and reduced hepatocyte TG accumulation; however, these responses were suppressed in the presence of an AMPK inhibitor. Restoration of AMPK phosphorylation by administration of 5-aminoimidazole-4-carboxamide riboside in Vasp?/? mice reduced hepatic steatosis and normalized fatty acid oxidation and VLDL-TG secretion. Activation of VASP by the phosphodiesterase-5 inhibitor, sildenafil, in db/db mice reduced hepatic steatosis and increased phosphorylated (p-)AMPK and p-acetyl CoA carboxylase. In Vasp?/? mice, however, sildendafil treatment did not increase p-AMPK or reduce hepatic TG content. These studies identify a role of VASP to enhance hepatic fatty acid oxidation by activating AMPK and to promote VLDL-TG secretion from the liver. PMID:23349495

Tateya, Sanshiro; Rizzo-De Leon, Norma; Handa, Priya; Cheng, Andrew M.; Morgan-Stevenson, Vicki; Ogimoto, Kayoko; Kanter, Jenny E.; Bornfeldt, Karin E.; Daum, Guenter; Clowes, Alexander W.; Chait, Alan; Kim, Francis

2013-01-01

39

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

PubMed Central

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

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

2013-01-01

40

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

PubMed

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 & Dbioassay module system. Saturated (C6:0 to C16:0 and C18:0) and unsaturated fatty acids (C11:1 to C14:1, C16:1, C18:1, and C18:2) showed biting deterrence index (BDI) values significantly greater than ethanol, the negative control. Among the saturated fatty acids, mid chain length acids (C10:0 to C13:0) showed higher biting deterrence than short (C6:0 to C9:0) and long chain length acids (C14:0 to C18:0), except for C8:0 and C16:0 that were more active than the other short and long chain acids. The BDI values of mid chain length acids (C10:0 to C13:0) were not significantly less than N, N-diethyl-meta-toluamide (DEET), the positive control. Among the unsaturated fatty acids, C11:1 showed the highest activity (BDI = 1.05) and C18:2 had the lowest activity (BDI = 0.7). In C11:1, C12:1, and C14:1 BDI values were not significantly less than DEET. After the preliminary observations, residual activity bioassays were performed on C11:0, C12:0, C11:1, and C12:1 over a 24-h period. All the fatty acids (C11:0, C12:0, C11:1, and C12:1) and DEET showed significantly higher activity at all test intervals than the solvent control. At treatment and 1-h posttreatment, all fatty acids showed proportion not biting (PNB) values not significantly less than DEET. At 3-, 6-, and 12-h posttreatment, all fatty acids showed PNB values significantly greater than DEET. At 24-h posttreatment, only the PNB value for C12:0 was significantly higher than DEET. The dose-responses of C12:0 and DEET were determined at concentrations of 5-25 nmol/cm2. As in the residual activity bioassays, the PNB values for C12:0 and DEET at 25 nmol/cm(2) were not significantly different. However, at lower concentrations, the PNB values for C12:0 were significantly greater than DEET. These results clearly indicate that mid chain length fatty acids not only have levels of biting deterrence similar to DEET at 25 nmnol/cm(2) in our test system, but also appeared to be more persistent than DEET. In contrast, in vivo cloth patch assay system showed that the mid-chain length fatty acids, C11:0, C11:1, C12:0, and C12:1 had minimum effective dose (MED) values greater than DEET against Ae. aegypti and their relative repellency varied according to species tested. The MED values of 120 (C11:0), 145 (C12:0) and 116 (C11:1) nmol/cm(2) against Anopheles quadrimaculatus Say, indicated that these acids were not as potent as DEET with a MED of 54 nmol/cm(2). The MED ratio of the C11:0 and C11:1 for all three mosquito species indicated the C11 saturated and unsaturated acids as more repellent than their corresponding C12:0 and C12:1 homologues. PMID:23270165

Ali, Abbas; Cantrell, Charles L; Bernier, Ulrich R; Duke, Stephen O; Schneider, John C; Agramonte, Natasha M; Khan, Ikhlas

2012-11-01

41

Dietary trans fatty acids in early life: a review  

Microsoft Academic Search

Trans fatty acids are unsaturated fatty acids with at least a double trans configuration, resulting in a more rigid molecule close to a saturated fatty acid. These appear in dairy fat because of ruminal activity, and in hydrogenated oils; margarines, shortenings and baked goods contain relatively high levels of trans fatty acids. These fatty acids can be incorporated into both

Elvira Larqué; Salvador Zamora; Angel Gil

2001-01-01

42

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

PubMed Central

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

Mohadjerani, Maryam; Tavakoli, Rahmatollah; Hosseinzadeh, Rahman

2014-01-01

43

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

E-print Network

Altered Constitutive Expression of Fatty Acid-metabolizing Enzymes in Mice Lacking the Peroxisome University School of Medicine, Matsumoto, Nagano 390, Japan Peroxisome proliferator-activated receptor (PPAR of peroxisomal and mitochondrial fatty acid metabolizing enzymes were deter- mined in the PPAR null mouse

Omiecinski, Curtis

44

Abiotic synthesis of fatty acids  

NASA Technical Reports Server (NTRS)

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

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

1978-01-01

45

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

NASA Astrophysics Data System (ADS)

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

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

46

Fatty Acid Carcass Mapping  

E-print Network

FATTY ACID CARCASS MAPPING A Thesis by STACEY NICOLE TURK Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE May 2008... Major Subject: Animal Science FATTY ACID CARCASS MAPPING A Thesis by STACEY NICOLE TURK Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE...

Turk, Stacey N.

2010-01-14

47

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

PubMed

The antibacterial activity of selected fatty acids and essential oils was examined against two gram-negative (Pseudomonas fluorescens and Serratia liquefaciens) and four gram-positive (Brochothrix thermosphacta, Carnobacterium piscicola, Lactobacillus curvatus, and Lactobacillus sake) bacteria involved in meat spoilage. Various amounts of each preservative were added to brain heart infusion or MRS (deMan, Rogosa and Sharpe) agars, and the minimum inhibitory concentration was determined for each organism. Essential oils were analysed by gas-liquid chromatography to determine the concentration of selected components commonly found in spices. B. thermosphacta, P. fluorescens and S. liquefaciens were not affected by fatty acids, and generally overcame the inhibitory effect of essential oils after 24 h of exposure. Among the fatty acids, lauric and palmitoleic acids exhibited the greatest inhibitory effect with minimum inhibitory concentrations of 250 to 500 micrograms/ml, while myristic, palmitic, stearic and oleic acids were completely ineffective. For essential oils, clove, cinnamon, pimento, and rosemary were found to be the most active. The 1/100 dilution of those oils inhibited at least five of the six tested organisms. A relationship was found between the inhibitory effect of essential oils and the presence of eugenol and cinnamaldehyde. PMID:9310850

Ouattara, B; Simard, R E; Holley, R A; Piette, G J; Bégin, A

1997-07-22

48

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. PMID:14676330

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

49

Omega-3 Fatty Acids and Pregnancy  

PubMed Central

Omega-3 fatty acids are essential fatty acids that must be consumed in the diet. Adequate consumption of omega-3 fatty acids is vitally important during pregnancy as they are critical building blocks of fetal brain and retina. Omega-3 fatty acids may also play a role in determining the length of gestation and in preventing perinatal depression. The most biologically active forms of omega-3 fatty acids are docosahexaenoic acid and eicosapentaenoic acid, which are primarily derived from marine sources such as seafood and algae. Recent surveys, however, indicate that pregnant women in the United States and in other countries eat little fish and therefore do not consume enough omega-3 fatty acids, primarily due to concern about the adverse effects of mercury and other contaminants on the developing fetus. This review discusses the benefits of omega-3 fatty acid consumption during pregnancy and provides guidelines for obstetricians advising patients. PMID:21364848

Coletta, Jaclyn M; Bell, Stacey J; Roman, Ashley S

2010-01-01

50

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

Microsoft Academic Search

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

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

1997-01-01

51

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

Microsoft Academic Search

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

Andrew P. Desbois; Valerie J. Smith

2010-01-01

52

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

53

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

PubMed Central

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

Xu, Xiaojun; Gopalacharyulu, Peddinti; Seppanen-Laakso, Tuulikki; Ruskeepaa, Anna-Liisa; Aye, Cho Cho; Carson, Brian P.; Mora, Silvia; Oresic, Matej; Teleman, Aurelio A.

2012-01-01

54

Structure-activity relationships of fatty acid amide ligands in activating and desensitizing G protein-coupled receptor 119.  

PubMed

The purpose of the current study was to apply a high throughput assay to investigate the structure-activity relationships of fatty acid amides for activating and desensitizing G protein-coupled receptor 119, a promising therapeutic target for both type 2 diabetes and obesity. A cell-based, homogenous time resolved fluorescence (HTRF) method for measuring G protein-coupled receptor 119-mediated increase of cyclic adenosine monophosphate (cAMP) levels was validated and applied in this study. Using novel fatty acid amides and detailed potency and efficacy analyses, we have demonstrated that degree of saturation in acyl chain and charged head groups of fatty acid amides have profound effects on the ability of these compounds to activate G protein-coupled receptor 119. In addition, we have demonstrated for the first time that pretreatments with G protein-coupled receptor 119 agonists desensitize the receptor and the degrees of desensitization caused by fatty acid amides correlate well with their structure-activity relationships in activating the receptor. PMID:24184668

Kumar, Pritesh; Kumar, Akhilesh; Song, Zhao-Hui

2014-01-15

55

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

PubMed

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

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

2013-12-01

56

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. PMID:22685301

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

2012-01-01

57

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

Microsoft Academic Search

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

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

2002-01-01

58

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

Microsoft Academic Search

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

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

1993-01-01

59

[The effect of the new Russian concentrate of n-3 polyunsaturated fatty acids epaden on thrombocyte functional activity in vitro].  

PubMed

Epaden, the new domestic concentrate of n-3 polyunsaturated fatty acids (PUFA), is capable of inhibiting in vitro the human thrombocyte aggregation induced by ADP, collagen, and thrombin. It was established that the effect can hardly be related to the action of cyclooxygenase metabolites of eicosapentadienoic acid (entering into the epaden composition). The activity of epaden is probably explained by the effect of lipoxygenase metabolites of the n-3 polyunsaturated fatty acids or by the ligand properties of polyene acids entering into epaden. In addition, epaden is capable of reducing the release of thrombocyte factor 4 and tissue type plasminogen activator inhibitor from activated thrombocytes. PMID:10763110

Kalugin, S A; Petrukhina, G N; Makarov, V A; Gandel', V G

2000-01-01

60

Free fatty acid-induced platelet aggregation: studies with solubilized and nonsolubilized fatty acids.  

PubMed

The aggregation response of washed porcine platelets to the sodium salts of stearic, oleic, palmitic, and myristic acids was analyzed turbidometrically. The fatty acids were prepared as aqueous suspensions and as taurocholate- or albumin-solubilized systems. The final concentration of fatty acid in the platelet preparation varied between 70 and 600 microM. This range was within or below the normal physiological limits of 300-1200 microM. Platelet aggregation was observed with both the suspended and taurocholate-solubilized fatty acids. The extent of platelet aggregate formation increased with the fatty acid concentration and chain length. With the exception of stearate, the taurocholate-solubilized fatty acids were more active than the suspensions. Albumin-solubilized fatty acids were devoid of platelet aggregating activity. Particle-size analysis of the solubilized fatty acids indicated that fatty acid precipitation had occurred subsequent to the addition of taurocholate-solubilized fatty acids to the platelets. This precipitation did not occur with the albumin-solubilized systems, suggesting that the fatty acids must assume a particulate physical state to induce aggregation. Platelet aggregation induced by fatty acids was not inhibited by 80 nM epoprostenol, 75 microM alprostadil, or 150 microM indomethacin. This finding indicated that the fatty acid-induced platelet aggregation was independent of cyclic AMP-related calcium shift, cyclooxygenase-arachidonate, or granular nucleotide release mechanisms. PMID:6101166

Zentner, G M; Cardinal, J R; Kim, S W

1981-09-01

61

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

PubMed Central

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

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

2009-01-01

62

Electrophilic Nitro-fatty Acids Activate NRF2 by a KEAP1 Cysteine 151-independent Mechanism*  

PubMed Central

Nitro-fatty acids (NO2-FAs) are electrophilic signaling mediators formed in vivo via nitric oxide (NO)- and nitrite (NO2?)-dependent reactions. Nitro-fatty acids modulate signaling cascades via reversible covalent post-translational modification of nucleophilic amino acids in regulatory proteins and enzymes, thus altering downstream signaling events, such as Keap1-Nrf2-antioxidant response element (ARE)-regulated gene expression. In this study, we investigate the molecular mechanisms by which 9- and 10-nitro-octadec-9-enoic acid (OA-NO2) activate the transcription factor Nrf2, focusing on the post-translational modifications of cysteines in the Nrf2 inhibitor Keap1 by nitroalkylation and its downstream responses. Of the two regioisomers, 9-nitro-octadec-9-enoic acid was a more potent ARE inducer than 10-nitro-octadec-9-enoic acid. The most OA-NO2-reactive Cys residues in Keap1 were Cys38, Cys226, Cys257, Cys273, Cys288, and Cys489. Of these, Cys273 and Cys288 accounted for ?50% of OA-NO2 reactions in a cellular milieu. Notably, Cys151 was among the least OA-NO2-reactive of the Keap1 Cys residues, with mutation of Cys151 having no effect on net OA-NO2 reaction with Keap1 or on ARE activation. Unlike many other Nrf2-activating electrophiles, OA-NO2 enhanced rather than diminished the binding between Keap1 and the Cul3 subunit of the E3 ligase for Nrf2. OA-NO2 can therefore be categorized as a Cys151-independent Nrf2 activator, which in turn can influence the pattern of gene expression and therapeutic actions of nitroalkenes. PMID:21357422

Kansanen, Emilia; Bonacci, Gustavo; Schopfer, Francisco J.; Kuosmanen, Suvi M.; Tong, Kit I.; Leinonen, Hanna; Woodcock, Steven R.; Yamamoto, Masayuki; Carlberg, Carsten; Yla-Herttuala, Seppo; Freeman, Bruce A.; Levonen, Anna-Liisa

2011-01-01

63

Reconstitution of the Fatty Acid Hydroxylase Activity of Cytochrome P450BM3 Utilizing Its Functional Domains  

Microsoft Academic Search

Cytochrome P450BM-3, a catalytically self-sufficient fatty acid monooxygenase fromBacillus megaterium,is a multidomain protein containing heme, FAD, and FMN. Previous attempts to reconstitute the fatty acid monooxygenase activity of intact P450BM-3 utilizing equimolar concentrations of the separate heme (BMP) and reductase (BMR) domains, have been unsuccessful because two-electron reduced FMN, which rapidly accumulates, is incapable of electron transfer to the heme

Irina Sevrioukova; Gilles Truan; Julian A. Peterson

1997-01-01

64

Altered Constitutive Expression of Fatty Acid-metabolizing Enzymes in Mice Lacking the Peroxisome Proliferator-activated Receptor a (PPARa)  

Microsoft Academic Search

Peroxisome proliferator-activated receptor a (PPARa )i s a member of the steroid\\/nuclear receptor superfamily and mediates the biological and toxicological effects of peroxi- some proliferators. To determine the physiological role of PPARa in fatty acid metabolism, levels of peroxisomal and mitochondrial fatty acid metabolizing enzymes were deter- mined in the PPARa null mouse. Constitutive liver b-oxida- tion of the long

Toshifumi Aoyama; Jeffrey M. Peters; Nobuko Iritanii; Tamie Nakajima; Kenichi Furihata; Takashi Hashimoto; Frank J. Gonzalez

1998-01-01

65

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

66

Regulatory Activity of Polyunsaturated Fatty Acids in T-Cell Signaling  

PubMed Central

n-3 polyunsaturated fatty acids (PUFA) are considered to be authentic immunosuppressors and appear to exert beneficial effects with respect to certain immune-mediated diseases. In addition to promoting T-helper 1 (Th1) cell to T-helper 2 (Th2) cell effector T-cell differentiation, n-3 PUFA may also exert anti-inflammatory actions by inducing apoptosis in Th1 cells. With respect to mechanisms of action, effects range from the modulation of membrane receptors to gene transcription via perturbation of a number of second messenger cascades. In this review, the putative targets of anti-inflammatory n-3 PUFA, activated during early and late events of T-cell activation will be discussed. Studies have demonstrated that these fatty acids alter plasma membrane micro-organization (lipid rafts) at the immunological synapse, the site where T-cells and antigen presenting cells (APC) form a physical contact for antigen initiated T-cell signaling. In addition, the production of diacylglycerol and the activation of different isoforms of protein kinase C (PKC), mitogen activated protein kinase (MAPK), calcium signaling, and nuclear translocation/activation of transcriptional factors, can be modulated by n-3 PUFA. Advantages and limitations of diverse methodologies to study the membrane lipid raft hypothesis, as well as apparent contradictions regarding the effect of n-3 PUFA on lipid rafts will be critically presented. PMID:20176053

Kim, Wooki; Khan, Naim A.; McMurray, David N.; Prior, Ian A.; Wang, Naisyin; Chapkin, Robert S.

2010-01-01

67

Fatty acids, sterols, phenols and antioxidant activity of Phoenix theophrasti fruits growing in Crete, Greece.  

PubMed

In the present study we report the chemical composition of the Cretan Phoenix theophrasti Gr. fruits, in comparison with dates, from its close relative Phoenix dactylifera L. for their nutritional value and their potential exploitation as a source of bioactive components such as phytosterols, lipids and polyphenols. The non polar dichloromethane (CH2Cl2) extract of the fruits was analysed by several techniques (TLC, CC, GC and GC-MS) and was found to consist mainly from fatty acids, hydrocarbons and phytosterols. Palmitic acid was the most abundant fatty acid, 12.49% of total saponifiables, while beta-sitosterol was the most prevalent phytosterol, 29.46% of total unsaponifiable lipid fraction. The polar methanolic extract was examined for its total phenolic content, by the Folin-Ciocalteu assay, as well as for its antioxidant activity through DPPH assay, in comparison with previous studies on the fruits of several Phoenix dactylifera varieties. This fraction was found to possess strong antioxidant activity despite its lower content of phenolic compounds in comparison with previously studied Phoenix dactylifera specimens. PMID:19030994

Liolios, C C; Sotiroudis, G T; Chinou, I

2009-03-01

68

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

PubMed Central

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

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

2013-01-01

69

(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

70

Fatty Acid Composition, Oxidative Stability, and Radical Scavenging Activity of Vegetable Oil Blends with Coconut Oil  

Microsoft Academic Search

Coconut (Cocos nucifera) contains 55–65% oil, having C12:0 as the major fatty acid. Coconut oil has >90% saturates and is deficient in monounsaturates\\u000a (6%), polyunsaturates (1%), and total tocopherols (29 mg\\/kg). However, coconut oil contains medium chain fatty acids (58%),\\u000a which are easily absorbed into the body. Therefore, blends of coconut oil (20–80% incorporation of coconut oil) with other\\u000a vegetable oils

A. S. Bhatnagar; P. K. Prasanth Kumar; J. Hemavathy; A. G. Gopala Krishna

2009-01-01

71

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. PMID:21130106

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

2011-01-01

72

The Homolytic and Heterolytic Fatty Acid Hydroperoxide Lyase-like Activities of Hematin  

Microsoft Academic Search

Pentenols and pentene dimers are biosynthetized in plants by homolytic fatty acid hydroperoxide lyase (HPL) or HPL-like enzymes. It has been found that these compounds can modify the flavor of olive oil. Reactions between hematin and 13-hydroperoxyoctadecatrienoic acid resulted in the formation of the same compounds via a free radical reaction in which an alkoxyl radical derived from linolenic acid

Jerome Delcarte; Philippe Jacques; Marie-Laure Fauconnier; Phryne Hoyaux; Kenji Matsui; Michel Marlier; Philippe Thonart

2001-01-01

73

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

SciTech Connect

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

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

1993-12-01

74

Modulation of (Na,K)-ATPase activity by membrane fatty acid composition: therapeutic implications in human hypertension.  

PubMed

Abstract Oxidative stress (OS) plays a key role in the pathophysiology of essential hypertension and is associated with changes in the cell membrane fatty acid composition and fluidity. As (Na,K)-ATPase is modulated by the surrounding lipid microenvironment, lipid peroxidation could alter the interactions of this enzyme with the membrane components. Thus, modifications in the membrane fatty acid profile will translate into effects on (Na,K)-ATPase activity. Accordingly, a decrease in this enzyme activity has been reported in hypertensive patients. The aim of this study was to evaluate the relationship between membrane fluidity and fatty acid composition and (Na,K)-ATPase activity in erythrocytes of essential hypertensive patients supplemented with antioxidant vitamins C and E. A double-blind, randomized, placebo-controlled study was conducted in 120 men with essential hypertension assigned to receive vitamin C (1 g/day)?+E (400 IU/day) or placebo for 8 weeks. Measurements included OS related parameters: GSH/GSSG ratio, F2-isoprostanes and antioxidant capacity of plasma, (Na,K)-ATPase activity and erythrocytes membrane fatty acid composition (PUFA, polyunsaturated fatty acids; SAFA, saturated fatty acids). Associations were assessed by Pearson correlation and the differences by Student t-test (p<0.05). Supplemented hypertensive patients showed higher activity of (Na,K)-ATPase and proportion of PUFA, and lower blood pressure, OS markers and proportion of SAFA, versus placebo. The activity of (Na,K)-ATPase correlated negatively with the proportion of SAFA, but positively with that of PUFA in both groups. Supplementation with vitamins C+E resulted in decreased OS and increased fluidity and PUFA proportion in the membrane, both of which positively modulate (Na,K)-ATPase activity, accounting for the blood pressure reduction. PMID:23659494

Rodrigo, Ramón; Miranda-Merchak, Andres; Valenzuela Grau, Rodrigo; Bachler, Juan P; Vergara, Leonardo

2014-01-01

75

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

PubMed

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

Zheng, Xuqin; Sun, Tao; Wang, Xiaodong

2013-07-01

76

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

PubMed Central

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

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

2014-01-01

77

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

PubMed

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

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

2014-01-21

78

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

PubMed

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

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

2013-10-15

79

Fatty Acid Elongation Is Independent of Acyl-Coenzyme A Synthetase Activities in Leek and Brassica napus1  

PubMed Central

In both animal and plant acyl elongation systems, it has been proposed that fatty acids are first activated to acyl-coenzyme A (CoA) before their elongation, and that the ATP dependence of fatty acid elongation is evidence of acyl-CoA synthetase involvement. However, because CoA is not supplied in standard fatty acid elongation assays, it is not clear if CoA-dependent acyl-CoA synthetase activity can provide levels of acyl-CoAs necessary to support typical rates of fatty acid elongation. Therefore, we examined the role of acyl-CoA synthetase in providing the primer for acyl elongation in leek (Allium porrum L.) epidermal microsomes and Brassica napus L. cv Reston oil bodies. As presented here, fatty acid elongation was independent of CoA and proceeded at maximum rates with CoA-free preparations of malonyl-CoA. We also showed that stearic acid ([1-14C]18:0)-CoA was synthesized from [1-14C]18:0 in the presence of CoA-free malonyl-CoA or acetyl-CoA, and that [1-14C]18:0-CoA synthesis under these conditions was ATP dependent. Furthermore, the appearance of [1-14C]18:0 in the acyl-CoA fraction was simultaneous with its appearance in phosphatidylcholine. These data, together with the s of a previous study (A. Hlousek-Radojcic, H. Imai, J.G. Jaworski [1995] Plant J 8: 803–809) showing that exogenous [14C]acyl-CoAs are diluted by a relatively large endogenous pool before they are elongated, strongly indicated that acyl-CoA synthetase did not play a direct role in fatty acid elongation, and that phosphatidylcholine or another glycerolipid was a more likely source of elongation primers than acyl-CoAs.

Hlousek-Radojcic, Alenka; Evenson, Kimberly J.; Jaworski, Jan G.; Post-Beittenmiller, Dusty

1998-01-01

80

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

Microsoft Academic Search

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

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

2007-01-01

81

Fatty acid-producing hosts  

SciTech Connect

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

Pfleger, Brian F; Lennen, Rebecca M

2013-12-31

82

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

PubMed

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

Desbois, Andrew P; Lawlor, Keelan C

2013-01-01

83

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. PMID:10594123

Poirier, Yves; Ventre, Giovanni; Caldelari, Daniela

1999-01-01

84

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

PubMed Central

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

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

2014-01-01

85

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

PubMed

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

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

2014-01-01

86

Comparative topical pheromonotropic activity of insect pyrokinin\\/PBAN amphiphilic analogs incorporating different fatty and\\/or cholic acid components  

Microsoft Academic Search

This study presents a comparison of the topical pheromonotropic activity in the tobacco budworm moth of a series of amphiphilic pseudopeptide analogs of the insect pyrokinin\\/PBAN peptide class incorporating fatty acids of varying chain lengths. While the C16 analog fails to penetrate the moth cuticle, and the C12 only moderately so, shorter chain analogs transmigrate the moth cuticle readily with

Ronald J. Nachman; Peter E. A. Teal; Istvan Ujvary

2001-01-01

87

DIETARY (n-3) FATTY ACIDS INCREASE SUPEROXIDE DISMUTASE ACTIVITY AND DECREASE THROMBOXANE PRODUCTION IN THE RAT HEART  

Microsoft Academic Search

The aims of the present studies were to examine the effects of fish oil (containing (n-3) polyunsaturated fatty acids) on myocardial thromboxane and prostacyclin production, superoxide dismutase (SOD) activity and malondialdehyde (MDA) production in the rat. Male rats were fed standard pellet diets and the same diets enriched with 7% (w\\/w) stabilized fish oil or 7% butter (saturated fat) for

Riitta Luostarinen; Rolf Wallin; Tom Saldeen

1997-01-01

88

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

89

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

Microsoft Academic Search

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

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

90

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

SciTech Connect

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

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

2013-07-05

91

Inhibition of antibacterial activity of himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus, by fatty acid sodium salts.  

PubMed Central

Himastatin, a cyclohexadepsipeptide antibiotic, had in vivo antitumor activity against localized P388 leukemia and B16 melanoma but had no distal site antitumor activity. An in vitro Bacillus subtilis well-agar diffusion assay was employed to test the hypothesis that himastatin was enzymatically inactivated. The activity of himastatin against B. subtilis was inhibited when himastatin was mixed with mouse liver S9 fraction and microsomes. However, subsequent investigations demonstrated that the markedly decreased antibacterial activity was not enzymatic in nature but was related to the presence of certain fatty acid salts. Saturated fatty acid sodium salts with a carbon chain number of 8 or more reduced the antimicrobial activity of himastatin 50 to 100 times. If antibiotics such as ampicillin, bacitracin, chloramphenicol, and tunicamycin were used in place of himastatin, no meaningful reduction in antibacterial activity occurred. However, the antibacterial activity of the membrane-active peptide antibiotic polymyxin B, but not that of polymyxin E (colistin), was reduced in a manner similar to that of himastatin. Importantly, the activity of himastatin against HCT-116 colon adenocarcinoma cells in soft agar was markedly reduced in the presence of sodium palmitate as the reference fatty acid salt. The data indicate that himastatin may be trapped in micelles in vitro. It may be speculated that the lack of distal site antitumor activity resulted from similar complex formation between himastatin and lipids in vivo. The results also suggest that the cancer cytotoxic and antimicrobial effects of himastatin may result from interactions with the cell membrane. PMID:7872760

Mamber, S W; Brookshire, K W; Dean, B J; Firestone, R A; Leet, J E; Matson, J A; Forenza, S

1994-01-01

92

Fatty Acids and Eicosanoids Regulate Gene Expression through Direct Interactions with Peroxisome Proliferator-Activated Receptors alpha and gamma  

Microsoft Academic Search

Peroxisome proliferator-activated receptors (PPARs) alpha and gamma are key regulators of lipid homeostasis and are activated by a structurally diverse group of compounds including fatty acids, eicosanoids, and hypolipidemic drugs such as fibrates and thiazolidinediones. While thiazolidinediones and 15-deoxy-Delta 12,14-prostaglandin J2 have been shown to bind to PPARgamma , it has remained unclear whether other activators mediate their effects through

Steven A. Kliewer; Scott S. Sundseth; Stacey A. Jones; Peter J. Brown; G. Bruce Wisely; Cecilia S. Koble; Pallavi Devchand; Walter Wahli; Timothy M. Willson; James M. Lenhard; Jurgen M. Lehmann

1997-01-01

93

Digestion and absorption of polyunsaturated fatty acids  

E-print Network

bring to light the esterification step, particularly the integration of polyunsatura- ted fatty acids. polyunsaturated fatty acid / digestion / absorption pathway / enterocyte esterification / intesti- nal lipoprotein

Boyer, Edmond

94

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

PubMed

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

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

2008-03-12

95

Directed tagging of the Arabidopsis FATTY ACID ELONGATION1 (FAE1) gene with the maize transposon activator.  

PubMed Central

The FATTY ACID ELONGATION1 (FAE1) gene of Arabidopsis is required for the synthesis of very long chain fatty acids in the seed. The product of the FAE1 gene is presumed to be a condensing enzyme that extends the chain length of fatty acids from C18 to C20 and C22. We report here the cloning of FAE1 by directed transposon tagging with the maize element Activator (Ac). An unstable fae1 mutant was isolated in a line carrying Ac linked to the FAE1 locus on chromosome 4. Cosegregation and reversion analyses established that the new mutant was tagged by Ac. A DNA fragment flanking Ac was cloned by inverse polymerase chain reaction and used to isolate FAE1 genomic clones and a cDNA clone from a library made from immature siliques. The predicted amino acid sequence of the FAE1 protein shares homology with those of other condensing enzymes (chalcone synthase, stilbene synthases, and beta-ketoacyl-acyl carrier protein synthase III), supporting the notion that FAE1 is the structural gene for a synthase or condensing enzyme. FAE1 is expressed in developing seed, but not in leaves, as expected from the effect of the fae1 mutation on the fatty acid compositions of those tissues. PMID:7734965

James, D W; Lim, E; Keller, J; Plooy, I; Ralston, E; Dooner, H K

1995-01-01

96

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. PMID:21695012

Miner, Jeffrey H; Jahnsen, Frode

2011-01-01

97

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

PubMed Central

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

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

2012-01-01

98

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

PubMed Central

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.

2013-01-01

99

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

PubMed Central

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

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

2013-01-01

100

Detection of lyso-platelet-activating factor by high-performance liquid chromatography after derivatisation with fluorescent fatty acids.  

PubMed

Lyso-platelet-activating factor (lyso-PAF) was derivatised with 9-anthracenepropionic acid in the presence of dicyclohexylcarbodiimide, p-toluenesulfonic acid and 4-dimethylaminopyridine. The reaction yield exceeded 90% when the fatty acid was present in double molar amounts versus lyso-PAF. The procedure was equally effective in the derivatisation of other lysophospholipids. The derivatized phospholipids are detected by ultraviolet absorption (lambda = 253 nm) or fluorescence detection (using excitation at 254 nm and emission at 450 nm). The technique was applied successfully to the detection of lyso-PAF in complement activated rabbit plasma. PMID:2387879

Salari, H; Eigendorf, G K

1990-05-18

101

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

102

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. PMID:22728958

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

2012-01-01

103

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

104

An ortholog of farA of Aspergillus nidulans is implicated in the transcriptional activation of genes involved in fatty acid utilization in the yeast Yarrowia lipolytica  

SciTech Connect

Research highlights: {yields} POR1 is a Yarrowia lipolytica ortholog of farA involved in fatty acid response in A. nidulans. {yields} Deletion of POR1 caused growth defects on fatty acids. {yields} {Delta}por1 strain exhibited defects in the induction of genes involved in fatty acid utilization. -- Abstract: The yeast Yarrowia lipolytica effectively utilizes hydrophobic substrates such as fatty acids and n-alkanes. To identify a gene(s) regulating fatty acid utilization in Y. lipolytica, we first studied homologous genes to OAF1 and PIP2 of Saccharomyces cerevisiae, but their disruption did not change growth on oleic acid at all. We next characterized a Y. lipolytica gene, POR1 (primary oleate regulator 1), an ortholog of farA encoding a transcriptional activator that regulates fatty acid utilization in Aspergillus nidulans. The deletion mutant of POR1 was defective in the growth on various fatty acids, but not on glucose, glycerol, or n-hexadecane. It exhibited slight defect on n-decane. The transcriptional induction of genes involved in {beta}-oxidation and peroxisome proliferation by oleate was distinctly diminished in the {Delta}por1 strains. These data suggest that POR1 encodes a transcriptional activator widely regulating fatty acid metabolism in Y. lipolytica.

Poopanitpan, Napapol; Kobayashi, Satoshi; Fukuda, Ryouichi; Horiuchi, Hiroyuki [Department of Biotechnology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657 (Japan)] [Department of Biotechnology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657 (Japan); Ohta, Akinori, E-mail: aaohta@mail.ecc.u-tokyo.ac.jp [Department of Biotechnology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657 (Japan)] [Department of Biotechnology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657 (Japan)

2010-11-26

105

Modulation of antioxidant enzyme activities, platelet aggregation and serum prostaglandins in rats fed spray-dried milk containing n-3 fatty acid  

Microsoft Academic Search

Spray-dried milk enriched with n-3 fatty acids from linseed oil (LSO) or fish oil (FO) were fed to rats to study its influence on liver lipid peroxides, hepatic antioxidant enzyme activities, serum prostaglandins and platelet aggregation. Significant level of ? linolenic acid, eicosapentaenoic acid and docosahexaenoic acid were accumulated at the expense of arachidonic acid in the liver of rats

T. R. Ramaprasad; V. Baskaran; T. P. Krishnakantha; B. R. Lokesh

2005-01-01

106

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

PubMed Central

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

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

2008-01-01

107

The Peroxisome Proliferator-Activated Receptor Regulates Mitochondrial Fatty Acid Oxidative Enzyme Gene Expression  

Microsoft Academic Search

Medium-chain acyl-CoA dehydrogenase (MCAD) catalyzes a pivotal reaction in mitochondrial fatty acid (FA) beta-oxidation. To examine the potential role of FAs and their metabolites in the regulation of MCAD gene expression, we measured MCAD mRNA levels in animals fed inhibitors of mitochondrial long-chain FA import. Administration of carnitine palmitoyltransferase I inhibitors to mice or rats resulted in tissue-limited increases in

Tod Gulick; Sharon Cresci; Teresa Caira; David D. Moore; Daniel P. Kelly

1994-01-01

108

Increased Mitochondrial Activity in BMP7-Treated Brown Adipocytes, Due to Increased CPT1- and CD36-Mediated Fatty Acid Uptake  

PubMed Central

Abstract Aims: Brown adipose tissue dissipates chemical energy in the form of heat and regulates triglyceride and glucose metabolism in the body. Factors that regulate fatty acid uptake and oxidation in brown adipocytes have not yet been fully elucidated. Bone morphogenetic protein 7 (BMP7) is a growth factor capable of inducing brown fat mitochondrial biogenesis during differentiation from adipocyte progenitors. Administration of BMP7 to mice also results in increased energy expenditure. To determine if BMP7 is able to affect the mitochondrial activity of mature brown adipocytes, independent of the differentiation process, we delivered BMP7 to mature brown adipocytes and measured mitochondrial activity. Results: We found that BMP7 increased mitochondrial activity, including fatty acid oxidation and citrate synthase activity, without increasing the mitochondrial number. This was accompanied by an increase in fatty acid uptake and increased protein expression of CPT1 and CD36, which import fatty acids into the mitochondria and the cell, respectively. Importantly, inhibition of either CPT1 or CD36 resulted in a blunting of the mitochondrial activity of BMP7-treated cells. Innovation: These findings uncover a novel pathway regulating mitochondrial activities in mature brown adipocytes by BMP7-mediated fatty acid uptake and oxidation. Conclusion: In conclusion, BMP7 increases mitochondrial activity in mature brown adipocytes via increased fatty acid uptake and oxidation, a process that requires the fatty acid transporters CPT1 and CD36. Antioxid. Redox Signal. 19, 243–257. PMID:22938691

Townsend, Kristy L.; An, Ding; Lynes, Matthew D.; Huang, Tian Lian; Zhang, Hongbin; Goodyear, Laurie J.

2013-01-01

109

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

PubMed Central

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

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

2012-01-01

110

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

E-print Network

polyunsaturated fatty acid (PUFA) diet, a high saturated fatty acid (SFA) diet or a mixed fatty acid control (CTLEffects of dietary fatty acid composition on the regulation of carnitine palmitoyltransferase (CPT Peroxisome proliferator activated receptor Polyunsaturated fatty acids Rainbow trout Dietary fatty acid

McClelland, Grant B.

111

Peroxisome proliferator-activated receptor ? promotes very low-density lipoprotein-derived fatty acid catabolism in the macrophage  

PubMed Central

Significant attention has focused on the role of low-density lipoprotein (LDL) in the pathogenesis of atherosclerosis. However, recent advances have identified triglyceride-rich lipoproteins [e.g., very LDL (VLDL)] as independent risk predictors for this disease. We have previously demonstrated peroxisome proliferator-activated receptor (PPAR)?, but not PPAR?, is the major nuclear VLDL sensor in the macrophage, which is a crucial component of the atherosclerotic lesion. Here, we show that, in addition to ?-oxidation and energy dissipation, activation of PPAR? by VLDL particles induces key genes involved in carnitine biosynthesis and lipid mobilization mediated by a recently identified TG lipase, transport secretion protein 2 (also named desnutrin, iPLA2?, and adipose triglyceride lipase), resulting in increased fatty acid catabolism. Unexpectedly, deletion of PPAR? results in derepression of target gene expression, a phenotype similar to that of ligand activation, suggesting that unliganded PPAR? suppresses fatty acid utilization through active repression, which is reversed upon ligand binding. This unique transcriptional mechanism assures a tight control of the homeostasis of VLDL-derived fatty acid and provides a therapeutic target for other lipid-related disorders, including dyslipidemia and diabetes, in addition to coronary artery disease. PMID:16467150

Lee, Chih-Hao; Kang, Kihwa; Mehl, Isaac R.; Nofsinger, Russell; Alaynick, William A.; Chong, Ling-Wa; Rosenfeld, John M.; Evans, Ronald M.

2006-01-01

112

Inhibition of the thioesterase activity of human fatty acid synthase by 1,4- and 9,10-diones.  

PubMed

Fatty acid synthase (FASN) is the enzyme that synthesizes fatty acids de novo in human cells. Although FASN is generally expressed at low levels in most normal tissues, its expression is highly upregulated in many cancers. Consistent with this notion, inhibition of FASN activity has demonstrated potential to halt proliferation and induce cell death in vitro and to block tumor growth in vivo. Consequently, FASN is widely recognized as a valuable therapeutic target. In this report, we describe a variety of 1,4-quinones and 9,10-anthraquinones, including several natural compounds and some newly synthesized compounds, that potently inhibit the thioesterase (TE) domain of FASN. Inhibition of recombinant TE activity, inhibition of cellular FASN, and cytotoxicity in human prostate cancer cell lines and normal fibroblasts, is shown for the most potent inhibitors. Collectively, the data illustrate the novel inhibitory capacity of the 1,4-quinone and 9,10-anthraquinone pharmacophores against FASN. PMID:25177021

Odens, Herman; Lowther, Todd; Kridel, Steven; Watts, Laura; Filipponi, Lauren; Schmitt, Jeffrey

2014-01-01

113

Fasciola hepatica Fatty Acid Binding Protein Induces the Alternative Activation of Human Macrophages.  

PubMed

The liver fluke Fasciola hepatica is a highly evolved parasite that uses sophisticated mechanisms to evade the host immune response. The immunosuppressive capabilities of the parasite have been associated with antigens secreted through the parasite's tegument, called excretory-secretory products (ESPs). Proteomic studies have identified the fatty acid binding protein (FABP) as one of molecules present in the parasite ESPs. Although FABP has been investigated for potential use in the development of vaccines against fascioliasis, its direct interaction with cells of immune system has not been studied. In this study, FABP was purified in native form from soluble extracts of F. hepatica adult flukes using a combination of molecular sieving chromatography and preparative isoelectric focusing. The immunological effect of the purified protein, termed Fh12, was assayed in vitro using monocyte-derived macrophages (MDM) obtained from healthy human donors. Results from the assay indicate that Fh12 produced a significantly increased arginase expression and activity and induced the expression of chitinase-3-like protein (CHI3L1). The assay also showed that Fh12 downregulated the production of nitric oxide (NO) and the expression of nitric oxide synthase (NOS2). This indicates that Fh12 induced the production of alternatively activated macrophages (AAM?). The results also demonstrated the ability of Fh12 to downregulate the secretion of the proinflammatory and inflammatory cytokines tumor necrosis factor alpha (TNF-?), interleukin-12 (IL-12), and IL-1?B, even after stimulation with lipopolysaccharide (LPS), as well as its ability to stimulate the overexpression of IL-10. These results suggest a potent anti-inflammatory role for Fh12, which could occur via targeting of Toll-like receptor 4 (TLR4). PMID:25225247

Figueroa-Santiago, Olgary; Espino, Ana M

2014-12-01

114

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

PubMed

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

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

2014-04-01

115

[Fatty acids--2. Clinical and physiological significance].  

PubMed

Fatty acids play multiple roles in humans and other organisms. In triglycerides they are the source of metabolic energy, in adipose tissue they serve also as temperature and mechanical isolators, in the form of phospholipids they are structural components of membranes. Fatty acids originating from the sn-2 glycerol carbon of phosphatidylcholine can influence the activity of diglycerides as second messengers. Unsaturated FA with 18-20 carbon atoms are precursors of prostaglandins, leucotrienes and thromboxanes, which have a broad scale of regulatory properties and have autocrine as well as paracrine effects. Fatty acids are ligands of several nuclear receptors, which take part in the subcellular control of a number of metabolic pathways. Covalent modification of proteins by FA (acylation) enables FA incorporation into the membranes. Number of pathological stages is accompanied with changes in fatty acid composition, often expressed as decreased content of unsaturated and increased content of saturated fatty acids (e.g. dyslipidemia, malnutrition, inflammation and inherited diseases). Polyunsaturated fatty acids as dietary supplements are used in prevention and in the therapy of cardiovascular diseases and other metabolic disturbances. PMID:19634271

Tvrzická, E; Stanková, B; Vecka, M; Zák, A

2009-01-01

116

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.

117

Inhibition of hepatic glutathione-S-transferases by fatty acids and fatty acid esters.  

PubMed

Micromolar concentrations of polyunsaturated fatty acids and ascorbate esters of saturated fatty acids were found to cause a marked inhibition of rat and mouse hepatic glutathione-S-transferase (GST) activity towards 1-chloro-2,4-dinitrobenzene. Arachidonic acid was approximately 25 times more potent in inhibiting rat GST than palmitic acid which was the least effective. Both linoleic and arachidonic acids did not inhibit rat liver GST when ethacrynic acid was used as substrate while the reverse was true with 1,2-dichoro-4-nitrobenzene. In contrast, all the chemicals tested inhibited rat liver GST activity towards 4-nitropyridine N-oxide, indicating isozyme specificity. PMID:1949072

Mitra, A; Govindwar, S; Kulkarni, A P

1991-10-01

118

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

PubMed Central

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

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

2013-01-01

119

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; Conceição, Luis E C; Tocher, Douglas R

2012-04-01

120

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

NASA Astrophysics Data System (ADS)

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

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

2014-10-01

121

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

NASA Astrophysics Data System (ADS)

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

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

2014-08-01

122

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

PubMed

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

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

2014-10-01

123

Antimicrobial lipids: Natural and synthetic fatty acids and monoglycerides  

Microsoft Academic Search

Over 40 natural or synthetic lipophilic compounds were screened for antimicrobial activity. Gram (+) bacteria and yeasts but\\u000a not Gram (?) bacteria were affected by these agents. Epimino and selena fatty acids are more active than their corresponding\\u000a straight chain unsubstituted fatty acids. The position of selenium influenced the antimicrobial activity of the fatty acid.\\u000a The presence and position of

J. J. Kabara; R. Vrable

1977-01-01

124

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

NASA Astrophysics Data System (ADS)

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

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

2011-04-01

125

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

PubMed Central

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

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

2013-01-01

126

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

PubMed Central

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

2013-01-01

127

N-3 fatty acids inhibit vascular calcification via the p38-mitogen-activated protein kinase and peroxisome proliferator-activated receptor-gamma pathways.  

PubMed

Fish oil supplementation is associated with lower risk of coronary artery disease in humans, and it has been shown to reduce ectopic calcification in an animal model. However, whether N-3 fatty acids, active ingredients of fish oil, have direct effects on calcification of vascular cells is not clear. In this report, we investigated the effects of eicosapentaenoic acid and docosahexaenoic acid (DHA) on osteoblastic differentiation and mineralization of calcifying vascular cells (CVCs), a subpopulation of bovine aortic medial cells that undergo osteoblastic differentiation and form calcified matrix in vitro. Results showed that N-3 fatty acids inhibited alkaline phosphatase (ALP) activity and mineralization of vascular cells, suggesting that they directly affect osteoblastic differentiation in vascular cells. By Western blot analysis, DHA activated p38-mitogen-activated protein kinase (MAPK) but not extracellular-regulated kinase (ERK) or Akt. An inhibitor of p38-MAPK partially reversed the inhibitory effects of DHA on osteoblastic differentiation and mineralization. Transient transfection experiments showed that DHA also activated peroxisome proliferator-activated receptor-gamma (PPAR-gamma). Both p38-MAPK activator and PPAR-gamma agonists reproduced the inhibitory effects of DHA on CVC mineralization. Pretreatment with DHA also inhibited interleukin-6-induced ALP activity and mineralization. Together, these results suggest that N-3 fatty acids directly inhibit vascular calcification, and that the inhibitory effects are mediated by the p38-MAPK and PPAR-gamma pathways. PMID:16514067

Abedin, M; Lim, J; Tang, T B; Park, D; Demer, L L; Tintut, Y

2006-03-31

128

Inhibition of lymphocyte proliferation by free fatty acids. II. Toxicity of stearic acid towards phytohaemagglutinin-activated T cells.  

PubMed Central

Studies were performed to further characterize the effects of saturated fatty acids on murine T lymphocyte proliferation. Flow cytometry was used to show that the inhibitory effects of stearic acid (18:0) on [3H]thymidine uptake can be correlated with changes in cellular DNA content. Additional studies using flow cytometry and fluorescein diacetate as a viability stain showed that exogenous 18:0 was toxic for phytohemagglutinin (PHA)-stimulated T cells, whereas the viability of unstimulated T cells was less affected by 18:0. The inhibitory effects of 18:0 on T cell proliferation were evident as early as 4 hr after fatty acid addition and after a 10-hr exposure, the effects of 18:0 could not be reversed by washing the cells or by adding oleic acid (18:1). It is proposed that the inhibitory effects of 18:0 are dependent upon PHA-induced changes in T cell lipid metabolism. PMID:6333387

Buttke, T M; Cuchens, M A

1984-01-01

129

Nitro-fatty acids: novel anti-inflammatory lipid mediators  

PubMed Central

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.

2013-01-01

130

Influence of dietary essential fatty acid level on fatty acid composition in peripheral nerve and muscle  

E-print Network

fatty acids, in the presence of a very high linoleic acid level, the PUFA of the (n-6) series decreased of polyunsaturated fatty acids (Kishimoto et al., 1969). This observation may be related to the highly specializedInfluence of dietary essential fatty acid level on fatty acid composition in peripheral nerve

Paris-Sud XI, Université de

131

Distinction among isomeric unsaturated fatty acids as lithiated adducts by electrospray ionization mass spectrometry using low energy collisionally activated dissociation on a triple stage quadrupole instrument  

Microsoft Academic Search

Features of tandem mass spectra of dilithiated adduct ions of unsaturated fatty acids obtained by electrospray ionization\\u000a mass spectrometry with low-energy collisionally activated dissociation (CAD) on a triple stage quadrupole instrument are described.\\u000a These spectra distinguish among isomeric unsaturated fatty acids and permit assignment of double-bond location. Informative\\u000a fragment ions reflect cleavage of bonds remote from the charge site on

Fong-Fu Hsu; John Turk

1999-01-01

132

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

PubMed Central

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

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

2012-01-01

133

Fatty acid signalling in a mouse enteroendocrine cell line involves fatty acid aggregates rather than free fatty acids  

PubMed Central

Fatty acids induce cholecystokinin (CCK) secretion both in humans and from murine enteroendocrine cell lines. In both cases, only fatty acids above a critical acyl chain length (C10) are capable of inducing a response. Using the enteroendocrine cell line STC-1, the aim of this study was to determine whether this acyl chain length dependency is related to the fact that longer chain fatty acids are relatively insoluble in aqueous solutions and, if so, whether it is insoluble aggregates of fatty acids rather than free fatty acids which evoke CCK secretion. Solutions of fatty acids (chain length C8–C14), which were judged by filtration and Zeta sizer measurement to contain no fatty acid aggregates, never evoked CCK secretion from STC-1 cells. Filtering fatty acid solutions (of chain length C10, C12 and C14) through polytetrafluoroethylene (PTFE) filters (0.45 ?m pore size) revealed a narrow concentration range for each acid over which the amount of fatty acid removed from the solution increased sharply due to the formation of fatty acid aggregates. Filtration experiments, in which suspensions of C10, C12 and C14 fatty acids were passed through pore sizes of 0.2, 0.45 or 1.2 ?m, suggested that STC-1 cells did not respond to fatty acid aggregates of greater than 1.2 ?m, while at least 50 % of the CCK response was mediated by aggregates which were smaller than 0.45 ?m. Fatty acids induce CCK secretion from STC-1 cells by elevating intracellular Ca2+ concentration ([Ca2+]i). We therefore measured the effects on [Ca2+]i of filtered C10, C12 and C14 fatty acids. In all cases, [Ca2+]i responses were closely correlated with CCK secretion. Interestingly, while filtrates of fatty acid solutions evoked CCK secretion and elevated [Ca2+]i, freshly prepared solutions of fatty acids at the same concentration as the filtrates did not. This suggested that fatty acid aggregates were not in equilibrium with the solvent after filtration. The observation that the ability of C10, C12 and C14 filtrates to elevate [Ca2+]i decayed with time was consistent with this hypothesis. Furthermore, sonication of the filtrates abolished their ability to elevate [Ca2+]i. These data further suggest that it is a physical property of the fatty acid solution (the presence of insoluble fatty aggregates) which is responsible for the observed cellular responses. We conclude that Ca2+ mobilisation and CCK secretion in STC-1 cells is driven by a signal transduction mechanism that senses insoluble fatty acid aggregates, rather than free fatty acids in solution. PMID:11773321

Benson, R S P; Sidhu, S S; Jones, M N; Case, R M; Thompson, D G

2002-01-01

134

Contribution of nonesterified fatty acids to mitogen-activated protein kinase activation in human skeletal muscle during endurance exercise.  

PubMed

Mitogen-activated protein kinase (MAPK) pathways are activated in skeletal muscle during endurance exercise, but the upstream molecular events are incompletely resolved. As an increase in plasma nonesterified fatty acids (NEFA) is a common feature of long-lasting exercise, the authors tested the hypothesis that NEFA contribute to the activation of MAPK during endurance exercise. Acipimox was used before and during endurance exercise to prevent the elevation of plasma NEFA levels in healthy subjects and patients with diabetes. In 2 separate studies, healthy subjects cycled for 2 hr and patients with diabetes for 1 hr at 50% Wmax. In control conditions, plasma NEFA concentrations increased from 0.35 to 0.90 mM during exercise in healthy subjects and from 0.55 to 0.70 mM in patients with diabetes (p < .05). Phosphorylation states of extracellularly regulated kinase 1 and 2 (ERK1/2), p38, and c-Jun NH2-terminal kinases (JNK) were significantly increased after exercise in the vastus lateralis in both groups. Acipimox blocked the increase in plasma NEFA concentrations and almost completely repressed any rise in ERK1/2 and p38 but not in JNK. In conclusion, the data support a role for plasma NEFA in the activation of p38 and ERK1/2 in skeletal-muscle tissue of healthy and diabetic subjects during endurance exercise. Further investigation will be required to determine the molecular link between NEFA and MAPK activation during exercise in human skeletal muscle. PMID:23114833

Zbinden-Foncea, Hermann; van Loon, Luc J C; Raymackers, Jean-Marc; Francaux, Marc; Deldicque, Louise

2013-06-01

135

Conjugated Fatty Acid Synthesis  

PubMed Central

Conjugated linolenic acids (CLNs), 18:3 ?9,11,13, lack the methylene groups found between the double bonds of linolenic acid (18:3 ?9,12,15). CLNs are produced by conjugase enzymes that are homologs of the oleate desaturases FAD2. The goal of this study was to map the domain(s) within the Momordica charantia conjugase (FADX) responsible for CLN formation. To achieve this, a series of Momordica FADX-Arabidopsis FAD2 chimeras were expressed in the Arabidopsis fad3fae1 mutant, and the transformed seeds were analyzed for the accumulation of CLN. These experiments identified helix 2 and the first histidine box as a determinant of conjugase product partitioning into punicic acid (18:3 ?9cis,11trans,13cis) or ?-eleostearic acid (18:3 ?9cis,11trans,13trans). This was confirmed by analysis of a FADX mutant containing six substitutions in which the sequence of helix 2 and first histidine box was converted to that of FAD2. Each of the six FAD2 substitutions was individually converted back to the FADX equivalent identifying residues 111 and 115, adjacent to the first histidine box, as key determinants of conjugase product partitioning. Additionally, expression of FADX G111V and FADX G111V/D115E resulted in an approximate doubling of eleostearic acid accumulation to 20.4% and 21.2%, respectively, compared with 9.9% upon expression of the native Momordica FADX. Like the Momordica conjugase, FADX G111V and FADX D115E produced predominantly ?-eleostearic acid and little punicic acid, but the FADX G111V/D115E double mutant produced approximately equal amounts of ?-eleostearic acid and its isomer, punicic acid, implicating an interactive effect of residues 111 and 115 in punicic acid formation. PMID:22451660

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

2012-01-01

136

Modulation of antioxidant enzyme activities, platelet aggregation and serum prostaglandins in rats fed spray-dried milk containing n -3 fatty acid  

Microsoft Academic Search

Spray-dried milk enriched with n-3 fatty acids from linseed oil or fish oil were fed to rats to study its influence on liver lipid peroxides, hepatic antioxidant\\u000a enzyme activities, serum prostaglandins and platelet aggregation. Significant level of ? linolenic acid, eicosapentaenoic\\u000a acid and docosahexaenoic acid were accumulated at the expense of arachidonic acid in the liver of rats fed n-3

T. R. Ramaprasad; V. Baskaran; T. P. Krishnakantha; B. R. Lokesh

2005-01-01

137

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

PubMed Central

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

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

2014-01-01

138

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

PubMed

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

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

2011-05-01

139

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

140

Fatty Acids Suppress Autophagic Turnover in ?-Cells*  

PubMed Central

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

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

2011-01-01

141

Fatty acid, carotenoid and tocopherol compositions of 20 Canadian lentil cultivars and synergistic contribution to antioxidant activities.  

PubMed

Understanding the profile of lipophilic phytochemicals in lentils is necessary to better understand the health benefits of lentils. The fatty acid, carotenoid and tocopherol compositions and antioxidant activities of the lipophilic extracts of 20 lentil cultivars (10 red and 10 green) were therefore examined. Lentils contained 1.52-2.95% lipids, of which 77.5-81.7% were unsaturated essential fatty acids. Total tocopherols ranged from 37 to 64?g/g DW, predominantly ?-tocopherol (96-98% of the tocopherol content), followed by ?- and ?-tocopherol. trans-Lutein was the primary and major carotenoid (64-78%) followed by trans-zeaxanthin (5-13%). Carotenoids and tocopherols showed weak correlation with 2,2-diphenyl-1-picrylhydrazyl (DPPH) activity (r=0.4893 and 0.3259, respectively), but good correlation when combined (r=0.6688), suggesting they may act synergistically. Carotenoids were found to contribute the most to the strong antioxidant activity measured by photochemiluminescence (PCL) assay. Results from this study contribute to the development of lentil cultivars and related functional foods with increased health benefits. PMID:24837953

Zhang, Bing; Deng, Zeyuan; Tang, Yao; Chen, Peter; Liu, Ronghua; Ramdath, D Dan; Liu, Qiang; Hernandez, Marta; Tsao, Rong

2014-10-15

142

Structure-activity analysis of harmful algae inhibition by congeneric compounds: case studies of fatty acids and thiazolidinediones.  

PubMed

The occurrence of harmful algal blooms has been increasing significantly around the world. In order to ensure the safety of drinking water, procedures to screen potential materials as effective algicides are needed, and predictive methods which save both the labor and time compared with traditional experimental approaches, are particularly desirable. In this study, data from previous studies on the algal-growth inhibitory action of two kinds of compounds, namely, the action of fatty acids and thiazolidinediones on the harmful algae Heterosigma akashiwo and Chattonella marina, were modeled using multiple linear regression (MLR) based on quantitative structure-activity relationships (QSAR). The models were shown to have highly predictive ability and stability, and provided insight into the inhibitory mechanisms of congeneric compounds. The main descriptors in the fatty-acid models were the Connolly accessible area and the number of rotatable bonds, illustrating that molecular surface area and shape are important in their algicidal actions. In the thiazolidinedione models, the critical volume, octanol-water partition coefficient (LogP), and Connolly solvent-excluded volume were found to be significant, indicating that hydrophobicity, substituent group size, and mode of action are mechanistically important. Our results showed the algicidal activity of a series of compounds on different algae could be modeled, and each model is efficacious for compounds that fall into the application domain of the QSAR model. This work demonstrates how reliable predictions of the algicidal activity of novel compounds and explanations of their inhibitory mechanisms can be obtained. PMID:24562453

Huang, Haomin; Xiao, Xi; Shi, Jiyan; Chen, Yingxu

2014-06-01

143

Separation of saturated\\/unsaturated fatty acids  

Microsoft Academic Search

Fatty acid mixtures can be separated into one fraction rich in saturated fatty acids and the other rich in unsaturated acids.\\u000a Since saturated fatty acids have a higher melting point than unsaturated, liquid mixture to be fractionated is cooled to a\\u000a temperature at which the larger part of the saturated acids crystallize, while the greater part of unsaturated acids remain

G. Haraldsson

1984-01-01

144

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

Microsoft Academic Search

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

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

2004-01-01

145

Plant fatty acid hydroxylase  

DOEpatents

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

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

2000-01-01

146

Plant fatty acid hydroxylase  

SciTech Connect

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

Somerville, C.; Loo, F. van de

2000-02-22

147

Biological control of phytopathogenic fungi by fatty acids.  

PubMed

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

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

2008-08-01

148

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

PubMed Central

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

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

2013-01-01

149

Omega-3 fatty acids protect the brain against ischemic injury by activating Nrf2 and upregulating heme oxygenase 1.  

PubMed

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

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

2014-01-29

150

Nitrated fatty acids: Synthesis and measurement  

PubMed Central

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

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

2012-01-01

151

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

152

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

PubMed

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

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

2012-11-01

153

Fatty acid synthase dimers containing catalytically active beta-ketoacyl synthase or malonyl/acetyltransferase domains in only one subunit can support fatty acid synthesis at the acyl carrier protein domains of both subunits.  

PubMed

A double-tagging, dual affinity chromatographic procedure, which permits isolation of dimers independently mutated in each subunit, has been exploited to probe the functional topology of the animal fatty acid synthase. Dimers were engineered in which the chain-terminating thioesterase reaction was compromised by mutation of the (active-site) serine residue in both subunits; these dimers assembled two long-chain fatty acyl moieties, which remained covalently linked to the 4'-phosphopantetheine residues of the two acyl carrier protein domains. Significantly, dimers that contained an additional mutation that compromised the activity of either the beta-ketoacyl synthase or malonyl/acetyltransferase activity in only one subunit also assembled two long-chain acyl moieties. In contrast, in a control experiment, introduction of an additional mutation that compromised the function of the acyl carrier protein domain in only one subunit resulted in the assembly of only one long-chain acyl moiety per dimer. Because the beta-ketoacyl synthase and malonyl/acetyltransferase domains are located near the amino terminus of the polypeptide and the acyl carrier protein domain near the carboxyl terminus, these results support a modified model for the animal fatty acid synthase in which head-to-tail functional contacts are possible both within as well as between subunits. PMID:9857025

Rangan, V S; Joshi, A K; Smith, S

1998-12-25

154

Fatty acid biosynthesis in pea root plastids  

SciTech Connect

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

Stahl, R.J.; Sparace, S.A. (McGill Univ., Quebec (Canada))

1989-04-01

155

ON EXTRACELLULAR AND INTRACELLULAR VENOM ACTIVATORS OF THE BLOOD, WITH ESPECIAL REFERENCE TO LECITHIN AND FATTY ACIDS AND THEIR COMPOUNDS.  

PubMed

In normal serums of the majority of mammalian and avian blood there exists certain substances capable of activating venom haemolysin. They are extractable from serum by means of ether, and are capable of conferring upon the originally non-activating serum a power to activate venom, when mixed with the latter. The ethereal extract consists of fatty acids, neutral fats and possibly also some ether soluble organic soaps. The fatty acids and soaps, especially of the oleinic series, acquire certain characteristics of complements in general, when they are mixed with serum. They are inactive without the venom in the mixture; they are inactivable with calcium chloride; they exhibit a tendency to go off in activity with age; they are inactive or only weakly active at 0 degrees C., and they are extractable by ether. In testing the serum from which the ether soluble substances are removed, it is found that no venom activating property is left. Warm alcoholic extraction of such serum yields, however, a large quantity of lecithin. In the case of non-activating serums no venom activating fats appear in the ethereal extract. Lecithin exists in such serum in no less quantity than in the activating kind. The addition of oleinic acid or its soluble soaps to a non-activating serum, in a ratio which corresponds to the percentage of fatty acids or soaps contained in some of the easily activating serums, will make the serum highly active in regard to venom. In normal serum of dog there exists, besides the group of activators already mentioned, another kind of venom activators which has been identified as a lecithin compound acting in the manner of free lecithin. A very sharp differentiation of the haemolysis produced by this activator and by the other groups of activators is obtained by means of calcium chloride, which is powerless against lecithin or lecithin compounds, but effective in removing the action of the latter. This lecithin containing proteid can be precipitated by half saturation with ammonium sulphate, but is perfectly soluble in water, and is not coagulated in neutral alkaline salt solutions upon boiling. Alcohol precipitates a proteid-like coagulum and extracts lecithin from it; ether does not extract lecithin from this compound. Non-activating serums do not contain any such lecithin compound. Lecithin contained in other serum proteids, mainly as lecithalbumin, and perhaps as contained in globulin, is not able to activate venom. This is true of all the serums with which I worked; it matters not whether these fractions (obtained with ammonium sulphate) belong to the most activating serum (dog) or to the non-activating serum (ox). The non-coagulable portion of all heated serum contains a venom activator of the nature of lecithin. This activator is contained in a non-coagulable proteid described by Howell which is identical with Chabrie's albumon. As there is no ether-extractable lecithin in this portion of the serum, the activating property of heated serum must be due to this proteid compound of lecithin. That this lecithin proteid does not pre-exist in normal serum but is produced by the action of high temperature is true of all serums except that of the dog. In venom activation we know now that lecithin becomes reactive with venom when it is transformed from other proteid compounds into the non-coagulable form, the albumon. Howell's view of the non-existence of the non-coagulable proteid in normal serum seems to receive a biological support from venom haemolysis. Ovovitellin derived from hen's egg is one of the best venom activators of the lecithin proteid type. The cause of venom susceptibility of various kinds of blood corpuscles does not depend upon the existence of lecithin in the corpuscles, but solely upon the amount of fatty acids, and perhaps, also, soaps and fats, contained in the corpuscles. The protection which calcium chloride gives against venom haemolysis is proof of the absence of lecithin activation. From the stroma of susceptible corpuscles fatty acids or some fats can be extracted with ether. After ethereal e

Noguchi, H

1907-07-17

156

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

2010-04-01

157

8, 687725, 2008 Effect of fatty acids  

E-print Network

, high contents of humic acids in the aerosol, a struc- turally inhomogeneous, quite water solubleACPD 8, 687�725, 2008 Effect of fatty acids on HNO3 uptake to aqueous aerosol K. Stemmler et al Chemistry and Physics Discussions The effect of fatty acid surfactants on the uptake of nitric acid

Paris-Sud XI, Université de

158

Long-chain polyunsaturated fatty acids stimulate cellular fatty acid uptake in human placental choriocarcinoma (BeWo) cells.  

PubMed

Supplementation of long-chain polyunsaturated fatty acids (LCPUFAs) is advocated during pregnancy in some countries although very little information is available on their effects on placental ability to take up these fatty acids for fetal supply to which the fetal growth and development are critically dependent. To identify the roles of LCPUFAs on placental fatty acid transport function, we examined the effects of LCPUFAs on the uptake of fatty acids and expression of fatty acid transport/metabolic genes using placental trophoblast cells (BeWo). Following 24 h incubation of these cells with 100 microM of LCPUFAs (arachidonic acid, 20:4n-6, eicosapentaenoic acid, 20:5n-3, or docosahexaenoic acid, 22:6n-3), the cellular uptake of [(14)C] fatty acids was increased by 20-50%, and accumulated fatty acids were preferentially incorporated into phospholipid fractions. Oleic acid (OA, 18:1n-9), on the other hand, could not stimulate fatty acid uptake. LCPUFAs and OA increased the gene expression of ADRP whilst decreased the expression of ASCL3, ACSL4, ACSL6, LPIN1, and FABP3 in these cells. However, LCPUFAs but not OA increased expression of ACSL1 and ACSL5. Since acyl-CoA synthetases are involved in cellular uptake of fatty acids via activation for their channelling to lipid metabolism and/or for storage, the increased expression of ACSL1 and ACLS5 by LCPUFAs may be responsible for the increased fatty acid uptake. These findings demonstrate that LCPUFA may function as an important regulator of general fatty acid uptake in trophoblast cells and may thus have impact on fetal growth and development. PMID:19880178

Johnsen, G M; Weedon-Fekjaer, M S; Tobin, K A R; Staff, A C; Duttaroy, A K

2009-12-01

159

Estrogenic activities of Fatty acids and a sterol isolated from royal jelly.  

PubMed

We have previously reported that royal jelly (RJ) from honeybees (Apis mellifera) has weak estrogenic activity mediated by interaction with estrogen receptors that leads to changes in gene expression and cell proliferation. In this study, we isolated four compounds from RJ that exhibit estrogenic activity as evaluated by a ligand-binding assay for the estrogen receptor (ER) beta. These compounds were identified as 10-hydroxy-trans-2-decenoic acid, 10-hydroxydecanoic acid, trans-2-decenoic acid and 24-methylenecholesterol. All these compounds inhibited binding of 17beta-estradiol to ERbeta, although more weakly than diethylstilbestrol or phytoestrogens. However, these compounds had little or no effect on the binding of 17beta-estradiol to ERalpha. Expression assays suggested that these compounds activated ER, as evidenced by enhanced transcription of a reporter gene containing an estrogen-responsive element. Treatment of MCF-7 cells with these compounds enhanced their proliferation, but concomitant treatment with tamoxifen blocked this effect. Exposure of immature rats to these compounds by subcutaneous injection induced mild hypertrophy of the luminal epithelium of the uterus, but was not associated with an increase in uterine weight. These findings provide evidence that these compounds contribute to the estrogenic effect of RJ. PMID:18830443

Suzuki, Kazu-Michi; Isohama, Yoichiro; Maruyama, Hiroe; Yamada, Yayoi; Narita, Yukio; Ohta, Shozo; Araki, Yoko; Miyata, Takeshi; Mishima, Satoshi

2008-09-01

160

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

PubMed Central

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

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

2013-01-01

161

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

PubMed

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

Gorres, Kelly L; Daigle, Derek; Mohanram, Sudharshan; Miller, George

2014-07-01

162

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. PMID:23525438

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

163

PPAR? activation in human myotubes increases mitochondrial fatty acid oxidative capacity and reduces glucose utilization by a switch in substrate preference.  

PubMed

The role of peroxisome proliferator-activated receptor ? (PPAR?) activation on global gene expression and mitochondrial fuel utilization were investigated in human myotubes. Only 21 genes were up-regulated and 3 genes were down-regulated after activation by the PPAR? agonist GW501516. Pathway analysis showed up-regulated mitochondrial fatty acid oxidation, TCA cycle and cholesterol biosynthesis. GW501516 increased oleic acid oxidation and mitochondrial oxidative capacity by 2-fold. Glucose uptake and oxidation were reduced, but total substrate oxidation was not affected, indicating a fuel switch from glucose to fatty acid. Cholesterol biosynthesis was increased, but lipid biosynthesis and mitochondrial content were not affected. This study confirmed that the principal effect of PPAR? activation was to increase mitochondrial fatty acid oxidative capacity. Our results further suggest that PPAR? activation reduced glucose utilization through a switch in mitochondrial substrate preference by up-regulating pyruvate dehydrogenase kinase isozyme 4 and genes involved in lipid metabolism and fatty acid oxidation. PMID:23991827

Feng, Yuan Z; Nikoli?, Nataša; Bakke, Siril S; Boekschoten, Mark V; Kersten, Sander; Kase, Eili T; Rustan, Arild C; Thoresen, G Hege

2014-02-01

164

PPARalpha L162V polymorphism alters the potential of n-3 fatty acids to increase lipoprotein lipase activity.  

PubMed

Omega-3 fatty acids (FAs) may accelerate plasma triglyceride (TG) clearance by altering lipoprotein lipase (LPL) activity. Yet, the ability of n-3 FAs to increase LPL activity is dependent on transcription factors such as peroxisome proliferator-activated receptor alpha (PPARalpha). The objective was to examine the effects of n-3 FAs on LPL activity considering the occurrence of PPARalpha L162V polymorphism. First, 14 pairs of men either L162 homozygotes or carriers of the V162 allele were supplemented with n-3 FAs. Second, transient transfections in HepG2 cells, for the L162- and V162-PPARalpha variants with the peroxisome proliferator-response element from the human LPL gene, were transactivated with n-3 FAs. In vivo results demonstrate that the LPL activity increased non-significantly by 14.4% in L162 homozygotes compared with 6.6% in carriers of the PPARalpha-V162 allele, after n-3 FA supplementation. Additionally, the L162 homozygotes tended towards an inverse correlation between LPL activities and plasma TG levels. Conversely, carriers of the V162 allele showed no such relationship. In vitro data demonstrates that transcription rates of LPL tended to be higher for the L162-PPARalpha than V162-PPARalpha after n-3 FAs activation. Overall, these results indicate that n-3 FA supplementation increases the transcription rate of LPL to a greater extent in L162-PPARalpha than V162-PPARalpha. PMID:19937854

Rudkowska, Iwona; Caron-Dorval, Dominique; Verreault, Mélanie; Couture, Patrick; Deshaies, Yves; Barbier, Olivier; Vohl, Marie-Claude

2010-04-01

165

Derivatives of the cationic plant alkaloids berberine and palmatine amplify protonophorous activity of fatty acids in model membranes and mitochondria.  

PubMed

Previously it has been shown by our group that berberine and palmatine, penetrating cations of plant origin, when conjugated with plastoquinone (SkQBerb and SkQPalm), can accumulate in isolated mitochondria or in mitochondria of living cells and effectively protect them from oxidative damage. In the present work, we demonstrate that SkQBerb, SkQPalm, and their analogs lacking the plastoquinone moiety (C10Berb and C10Palm) operate as mitochondria-targeted compounds facilitating protonophorous effect of free fatty acids. These compounds induce proton transport mediated by small concentrations of added fatty acids both in planar and liposomal model lipid membranes. In mitochondria, such an effect can be carried out by endogenous fatty acids and the adenine nucleotide translocase. PMID:23026390

Pustovidko, Antonina V; Rokitskaya, Tatiana I; Severina, Inna I; Simonyan, Ruben A; Trendeleva, Tatiana A; Lyamzaev, Konstantin G; Antonenko, Yuri N; Rogov, Anton G; Zvyagilskaya, Renata A; Skulachev, Vladimir P; Chernyak, Boris V

2013-09-01

166

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

PubMed

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

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

2014-01-01

167

Modulation of Nitro-fatty Acid Signaling  

PubMed Central

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

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

2013-01-01

168

Fatty acid-binding protein-hormone-sensitive lipase interaction. Fatty acid dependence on binding.  

PubMed

Adipose lipolysis is mediated, in part, via interaction of fatty acid-binding protein (FABP) with hormone-sensitive lipase (HSL). Mice with reduced FABP content in fat (adipocyte FABP null) exhibit diminished fat cell lipolysis, whereas transgenic mice with increased FABP content in fat (epithelial FABP transgenic) exhibit enhanced lipolysis. To examine the relationship between the binding of FABP to HSL and activation of catalytic activity, isothermal titration microcalorimetry as well as kinetic analysis using a variety of FABP isoforms have been employed. In the absence of fatty acids, no FABP-HSL association could be demonstrated for any FABP form. However, in the presence of 10 microm oleate, A-FABP and E-FABP each bound to HSL with high affinity (Kd of 0.5 and 3 nM, respectively) in a approximately 1:1 molar stoichiometry, whereas liver FABP and intestinal FABP did not exhibit any association. To compare binding to catalysis, each FABP isoform was incubated with HSL in vitro, and enzymatic activity was assessed. Importantly, each FABP form stimulated HSL activity approximately 2-fold using cholesteryl oleate as substrate but exhibited no activation using p-nitrophenyl butyrate. The activation by A-FABP was dependent upon its fatty acid binding properties because a non-fatty acid binding mutant, R126Q, failed to activate HSL. These results suggest that binding and activation of HSL by FABPs are separate and distinct functions and that HSL contains a site for fatty acid binding that allows for FABP association. PMID:13129924

Jenkins-Kruchten, Anne E; Bennaars-Eiden, Assumpta; Ross, James R; Shen, Wen-Jun; Kraemer, Fredric B; Bernlohr, David A

2003-11-28

169

Short Communication: Characterization of Madin-Darby Bovine Kidney Cell Line for Peroxisome Proliferator-Activated Receptors: Temporal Response and Sensitivity to Fatty Acids  

Microsoft Academic Search

The peroxisome proliferator-activated receptors (PPAR)arecriticalforlipidmetabolism,andmanyfatty acids are PPAR agonists. Madin-Darby bovine kidney (MDBK) cells were tested as an in vitro bovine model for PPAR activation, and preliminary evaluation of the effect of fatty acids on bovine PPAR was performed. Cells were treated with Wy-14643 (WY, specific PPAR? agonist) and rosiglitazone (ROSI, specific PPAR? ago- nist).Thegene expressionofspecificPPAR?-responsive genes such as carnitine

M. Bionaz; C. R. Baumrucker; E. Shirk; J. P. Vanden Heuvel; E. Block; G. A. Varga

2008-01-01

170

Fatty Acids are Key in 4-Hydroxy-2-Nonenal-Mediated Activation of Uncoupling Proteins 1 and 2  

PubMed Central

The production of reactive oxygen species (ROS) in mitochondria is very sensitive to the proton motive force and may be decreased by mild uncoupling, mediated e.g. by mitochondrial uncoupling proteins (UCPs). UCPs were conversely hypothesized to be activated by ROS. Conclusions from experiments studying the reactive product of lipid peroxidation 4-hydroxy-2-nonenal (HNE) in isolated mitochondria and UCP knock-out mice are highly controversial. Here we investigated the molecular mechanism of HNE action by evaluating the separate contributions of lipid and protein phases of the membrane and by comparing UCP1 and UCP2, which were reconstituted in planar lipid bilayers. We demonstrated that aldehyde does not directly activate either UCP1 or UCP2. However, HNE strongly potentiated the membrane conductance increase (Gm) mediated by different long-chain fatty acids in UCP-containing and in UCP-free membranes and this suggest the involvement of both lipid-mediated and protein-mediated mechanisms with FA playing the central role. Gm increase was concentration-dependent and exhibited a typical saturation kinetic with the binding constant 0.3 mM. By using Electron Paramagnetic Resonance, membrane fluidity change could be excluded as a cause for the HNE-mediated increase in the presence of FA. The impact of the HNE binding to definite positively charged UCP amino acid residues is discussed as a possible protein-mediated mechanism of the UCP activation. PMID:24204965

Gille, Lars; Jovanovic, Olga; Jezek, Petr; Jaburek, Martin; Pohl, Elena E.

2013-01-01

171

Preparation of Allylic Fatty Acid Amides in High Yield by Condensation of Fatty Acids with Allylisothiocyanate  

Microsoft Academic Search

We describe a new synthetic method for preparation in high yield of allylic fatty acid amides by heterogeneously catalyzed condensation of allylisothiocyanate with fatty acids in a concentrated mixture.

V. Delaveau; Z. Mouloungui; et A. Gaset

1996-01-01

172

?-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. PMID:20956542

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

2010-01-01

173

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

PubMed Central

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

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

2012-01-01

174

Polyunsaturated fatty acid metabolism in prostate cancer  

PubMed Central

Polyunsaturated fatty acids (PUFA) play important roles in the normal physiology and in pathological states including inflammation and cancer. While much is known about the biosynthesis and biological activities of eicosanoids derived from ?6 PUFA, our understanding of the corresponding ?3 series lipid mediators is still rudimentary. The purpose of this review is not to offer a comprehensive summary of the literature on fatty acids in prostate cancer but rather to highlight some of the areas where key questions remain to be addressed. These include substrate preference and polymorphic variants of enzymes involved in the metabolism of PUFA, the relationship between de novo lipid synthesis and dietary lipid metabolism pathways, the contribution of cyclooxygenases and lipoxygenases as well as terminal synthases and prostanoid receptors in prostate cancer, and the potential role of PUFA in angiogenesis and cell surface receptor signaling. PMID:22015690

Berquin, Isabelle M.; Edwards, Iris J.; Kridel, Steven J.

2013-01-01

175

Applying a multitarget rational drug design strategy: the first set of modulators with potent and balanced activity toward dopamine D3 receptor and fatty acid amide hydrolase.  

PubMed

Combining computer-assisted drug design and synthetic efforts, we generated compounds with potent and balanced activities toward both D3 dopamine receptor and fatty acid amide hydrolase (FAAH) enzyme. By concurrently modulating these targets, our compounds hold great potential toward exerting a disease-modifying effect on nicotine addiction and other forms of compulsive behavior. PMID:24691497

De Simone, Alessio; Ruda, Gian Filippo; Albani, Clara; Tarozzo, Glauco; Bandiera, Tiziano; Piomelli, Daniele; Cavalli, Andrea; Bottegoni, Giovanni

2014-05-18

176

The Fatty Acid Signaling Molecule cis-2-Decenoic Acid Increases Metabolic Activity and Reverts Persister Cells to an Antimicrobial-Susceptible State.  

PubMed

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

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

2014-11-15

177

Fatty Acids, Lipid Mediators, and T-Cell Function  

PubMed Central

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

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

2014-01-01

178

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

179

[The fatty acid composition of ordinary flax seed oil (Linum usitatissimum L.) cultivated in Georgia and its byological activity].  

PubMed

The aim of the study was individual quantitatively and qualitatively determination of fatty acids in ordinary flax seed oil (Linum usitatissimum L.), cultivated in Georgia. The neutral lipids extracts were fractionated and analyzed by high performance liquid chromatography (PTC-1, Waters) with refractory detector R-401. Analitical column (150,0x3,0 mm) was filled with reversphase Bondopak C18). Software OASIS-740 is used. The correction retention times of each fatty acids is compared with comformity standard. The investigation showed that in flax seed oil linoleic (31,3±2,1 mg%) and linolenic (40,2±2,9 mg%) acids were predominant and together constitute principal basic of research composition. The flax seed oil contained also palmitic and stearic acids in less quantitaty. PMID:24632654

2014-02-01

180

The increase of cell-membranous phosphatidylcholines containing polyunsaturated fatty acid residues induces phosphorylation of p53 through activation of ATR  

PubMed Central

Summary The G1 phase of the cell cycle is marked by the rapid turnover of phospholipids. This turnover is regulated by CTP:phosphocholine-cytidylyltransferase (CCT) and group VIA Ca2+-independent-phospholipase A2 (iPLA2). We previously reported that inhibition of iPLA2 arrests cells in G1 phase of the cell cycle by activating the p53-p21 checkpoint. Here we further characterize the mechanism of p53 activation. We show that specific inhibition of iPLA2 induces a time dependent phosphorylation of Ser15 in p53 in the absence of DNA damage. This phosphorylation requires the kinase ataxia-telangiectasia and Rad-3-related (ATR) but not the ataxia-telangiectasia-mutated (ATM) kinase. Moreover, we identify in cell membranes a significant increase of phosphatidylcholines (PCs) containing chains of polyunsaturated fatty acids and a decrease of PCs containing saturated fatty acids in response to inhibition of iPLA2. The time course of phosphorylation of Ser15 in p53 correlates with increasing levels of PCs containing polyunsaturated fatty acids. We further demonstrate that the PCs with linoleic acid in their sn-2 position (18:2n6) induce phosphorylation of Ser15 in p53 in an ATR-dependent manner. Our findings establish that cells can regulate the levels of polyunsaturated fatty acids in phospholipids through iPLA2-mediated deacylation of PCs. Disruption of this regulation increases the proportions of PCs containing polyunsaturated fatty acids and activates the ATR-p53 signalling pathway. PMID:18032786

Zhang, Xu Hannah; Zhao, Chunying; Ma, Zhongmin Alex

2010-01-01

181

Cellular Fatty Acid Metabolism and Cancer  

PubMed Central

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

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

2013-01-01

182

Phylogenomic reconstruction of archaeal fatty acid metabolism.  

PubMed

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

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

2014-04-01

183

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

SciTech Connect

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

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

2010-10-08

184

40 CFR 721.10323 - Glycerol fatty acid ester (generic).  

Code of Federal Regulations, 2012 CFR

...2012-07-01 2012-07-01 false Glycerol fatty acid ester (generic). 721...Chemical Substances § 721.10323 Glycerol fatty acid ester (generic). ...chemical substance identified generically as glycerol fatty acid ester (PMN...

2012-07-01

185

40 CFR 721.10323 - Glycerol fatty acid ester (generic).  

Code of Federal Regulations, 2013 CFR

...2013-07-01 2013-07-01 false Glycerol fatty acid ester (generic). 721...Chemical Substances § 721.10323 Glycerol fatty acid ester (generic). ...chemical substance identified generically as glycerol fatty acid ester (PMN...

2013-07-01

186

21 CFR 172.854 - Polyglycerol esters of fatty acids.  

...Polyglycerol esters of fatty acids. Polyglycerol esters of fatty acids, up to and including the...cottonseed oil, lard, palm oil from fruit, peanut oil, safflower oil...oil, and tallow and the fatty acids derived from these...

2014-04-01

187

Consequences of Essential Fatty Acids  

PubMed Central

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

Lands, Bill

2012-01-01

188

Radioiodinated fatty acid analogs for myocardial imaging  

SciTech Connect

Fatty acids are the preferred substrate for the normoxic heart. About sixty percent of the energy required by the myocardium is provided by fatty acid [beta]-oxidation. Many scientists have focused on the alterations in fatty acid metabolism in the ischemic heart for the development of radiolabelled fatty acids for functional imaging of the heart. Three main categories of compounds were synthesized: tetrazoles (1 and 2), glycidic and [alpha]-methylene acids (3-5), and analogs of oleic acid (6,7 and 7A). The tetrazole group has a similar pKa and size to that of a carboxyl group; however, such fatty acid analogs cannot undergo normal fatty acid metabolism. Glycidic and [alpha]-methylene analogs are potential irreversible inhibitors of fatty acid metabolism. Oleic acid analogs were investigated to assess the affect of stereochemical consequences on biodistribution. The key intermediates in the synthesis of the target compounds were [omega]-nitrophenyl alkylcarboxylic acids and alcohols, which were made using a variety of cross-coupling reactions. The Wittig reaction, which was used in the synthesis of tetrazole 1 and glycidic acid 3, gave low yields of the cross-coupled products. The remaining target compounds were synthesized by condensation of appropriate RCu (CN) ZnI and substituted benzyl bromides or by Pd[sup II] catalyzed cross-coupling of substituted arylhalides with suitable alkynes. The latter two reactions produced much higher yields of the desired products. All of the target compounds were radiolabeled with [sup 125]I by various Cu(I) catalyzed radioiodine exchange procedures and were then subjected to tissue biodistribution (TD) studies in rats. Except for the 15-(4-iodophenyl)-2-methylene-pentadecanoic acid (5), all of the fatty acid analogs failed to surpass clinically-used 15-(4-iodophenyl)pentadecanoic acid (IPPA) in their ability to be taken up and retained by the rat myocardium.

Ruyan, M.K.

1993-01-01

189

Polyunsaturated Fatty Acid Suppression of Hepatic Fatty Acid Synthase and S14 Gene Expression Does Not Require Peroxisome  

E-print Network

Not Require Peroxisome Proliferator-activated Receptor * (Received for publication, March 21, 1996, Maryland 20892 Dietary polyunsaturated fatty acids (PUFA) induce hepatic peroxisomal and microsomal fatty (CYP4A2)), and peroxisomal (acyl-CoA oxidase (AOX)) enzymes. PUFA ingestion in- duced mRNAAOX (2.3-fold

Omiecinski, Curtis

190

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

PubMed

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

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

2013-08-01

191

Cellular fatty acid profile and H(+)-ATPase activity to assess acid tolerance of Bacillus sp. for potential probiotic functional attributes.  

PubMed

The present study has been focused widely on comparative account of probiotic qualities of Bacillus spp. for safer usage. Initially, 170 heat resistant flora were isolated and selected for non-pathogenic cultures devoid of cytK, hblD, and nhe1 virulence genes. Subsequently, through biochemical tests along with 16S rRNA gene sequencing and fatty acid profiling, the cultures were identified as Bacillus megaterium (AR-S4), Bacillus subtilis (HR-S1), Bacillus licheniformis (Csm1-1a and HN-S1), and Bacillus flexus (CDM4-3c and CDM3-1). The selected cultures showed 70-80 % survival under simulated gastrointestinal condition which was also confirmed through H(+)-ATPase production. The amount of H(+)-ATPase increased by more than 2-fold when grown at pH 2 which support for the acid tolerance ability of Bacillus isolates. The study also examined the influence of acidic pH on cellular fatty acid composition of Bacillus spp. A remarkable shift in the fatty acid profile was observed at acidic pH through an increased amount of even numbered fatty acid (C16 and C18) in comparison with odd numbered (C15 and C17). Additionally, the cultures exhibited various probiotic functional properties. Overall, the study increases our understanding of Bacillus spp. and will allow both industries and consumers to choose for well-defined probiotic with possible health benefits. PMID:25125040

Shobharani, P; Halami, Prakash M

2014-11-01

192

Heterogeneity of Fatty Acids from Royal Jelly  

Microsoft Academic Search

THE presence of hydroxy fatty acids as the major component of the lipid portion of royal jelly was indicated many years ago by Townsend and Lucas1 and was confirmed recently by Butenandt and Rembold2. The latter authors characterized the major component as 10-hydroxy-2-decenoic acid. A trans configuration has been assigned to the double bond3,4. This unusual fatty acid has been

Nevin Weaver; JOHN H. LAW

1960-01-01

193

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

E-print Network

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

Arrington, Jennifer L

2012-06-07

194

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

PubMed Central

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

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

2013-01-01

195

Liposomes as fatty acids carriers in isolated rat liver: effect on energy metabolism and on isolated mitochondria activity  

Microsoft Academic Search

The effects of fatty acids (FA)-carrier, egg-lecithin liposomes (LIPO) as alternative to BSA, on ATP, glycogen and glucose\\u000a contents in isolated perfused liver of fed rats were non-invasively studied using31P\\/13C nuclear magnetic resonance (NMR). Oxidative phosohorylation was studied in isolated mitochondria from the same liver consecutively\\u000a to the NMR experiments. ATP content decreased slowly and ATP turnover was similar during

M. C. Delmas-Beauvieux; N. Leducq; E. Thiaudière; P. Diolez; H. Gin; P. Canioni; J. L. Gallis

2000-01-01

196

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

197

n-3 PUFA as Regulators of Cardiac Gene Transcription: A New Link between PPAR Activation and Fatty Acid Composition  

Microsoft Academic Search

The fatty acids regulate gene expression directly binding to nuclear receptors or affecting the protein content of transcription\\u000a factors. In this work, supplementing primary cultures of neonatal rat cardiomyocytes with 60 µM EPA or DHA, we demonstrated\\u000a by an ELISA assay an increased PPAR ?\\/? binding to DNA. n-3 PUFA supplementation deeply changed the acyl composition of both\\u000a cytosolic and nuclear

Mattia Di Nunzio; Francesca Danesi; Alessandra Bordoni

2009-01-01

198

Sulfonated branched chain fatty acids and esters  

Microsoft Academic Search

In continuation of work reported a year ago describing branched chain fatty acids, a series of monosodium methyl 2-sulfo-2-alkylalkanoates\\u000a [RR'C (SO3Na) CO2CH3] were synthesized. The surface active properties of these compounds were evaluated and compared with the corresponding disodium\\u000a 2-sulfo-2-alkylalkanoates [RR'C (SO3Na)CO2Na]. Alkaline hydrolysis rates show that the sodium methyl esters are stable. Relative to the disodium salts, these compounds

T. J. Micich; E. A. Diamond; R. G. Bistline; A. J. Stirton; W. C. Ault

1966-01-01

199

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

E-print Network

to high water temperatures. D 2004 Elsevier B.V. All rights reserved. Keywords: Fatty acid synthesisIn vitro effects of temperature and salinity on fatty acid synthesis in the oyster protozoan on fatty acid synthetic activities in the oyster protozoan parasite, Perkinsus marinus, were tested

Hartley, Troy W.

200

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

PubMed Central

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

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

2013-01-01

201

Fatty acid breakdown in developing embryos of Brassica napus L.  

PubMed

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

Chia, T; Rawsthorne, S

2000-12-01

202

In vitro antioxidant, anticholinesterase and antimicrobial activity studies on three Agaricus species with fatty acid compositions and iron contents: A comparative study on the three most edible mushrooms  

Microsoft Academic Search

The fatty acids of Agaricus essettei, Agaricus bitorquis and Agaricus bisporus were investigated by using GC and GC–MS. The dominant fatty acids were found to be linoleic (61.82–67.29%) and palmitic (12.67–14.71%) acids among the 13 fatty acids detected in the oils. Total unsaturation for the oils was calculated as 77.50%, 77.44%, and 79.72%, respectively. In vitro antioxidant, anticholinesterase and antimicrobial

Mehmet Öztürk; Mehmet Emin Duru; ?eyda Kivrak; Nazime Mercan-Do?an; Aziz Türkoglu; Mehmet Ali Özler

2011-01-01

203

The Fatty Acid Content of Ocean Water  

E-print Network

Typical Elution Curve obtained with a Differential Detector 10 Separation of Methyl Esters of Fatty Acids in @later of 10 Meter Depth at Station I on Cruise 59-H-I 23 CHAPTER I INTRODUCTION During the past fifty years. much effort has been expended... technique described by James and Martin (10). They showed that micro quantities of fatty acids could be separated and identified rapidly by this method (11). The extension of gas chromatographic separation to the methyl esters of the fatty acids...

Slowey, James Frank

2012-06-07

204

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

NASA Astrophysics Data System (ADS)

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

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

1995-12-01

205

Modulation of eosinophil chemotactic activities to leukotriene B4 by n-3 polyunsaturated fatty acids.  

PubMed

Eosinophil accumulation induced by leukotriene B4 appears to be involved in the pathogenesis of allergic diseases. We evaluated the effects of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) on chemotaxis to leukotriene B4 in guinea pig peritoneal eosinophils. Guinea pigs that were sensitized to polymyxin B were administered an intraperitoneal injection of polymyxin B (1 mg/animal) alone or combined with DHA (15 or 50 mg/kg, i.p.), EPA (50 or 100 mg/kg, i.p.), or with linoleic acid (LA) (100 mg/kg, i.p.). Forty hours later, eosinophils were obtained from the intraperitoneal lavage fluid and purified. The chemotactic and chemokinetic responses of eosinophils to leukotriene B4 were measured using a 96-well microchemotaxis chamber. DHA significantly decreased the chemotactic and chemokinetic responses of eosinophils in a dose-dependent fashion. A higher dose of EPA also significantly inhibited both of those responses, whereas LA had no effect. Our results suggested a possible mechanism for the improvement of allergic diseases by dietary supplementation with n-3 PUFA. PMID:9610849

Kikuchi, S; Sakamoto, T; Ishikawa, C; Yazawa, K; Torii, S

1998-03-01

206

Enzymatic acylation of isoorientin and isovitexin from bamboo-leaf extracts with fatty acids and antiradical activity of the acylated derivatives.  

PubMed

This study enzymatically acrylates two flavonoids from bamboo-leaf extracts, isoorientin and isovitexin, with different fatty acids as acyl donors using Candida antarctica lipase B (CALB). The conversion yield ranged from 35 to 80% for fatty acids with different chain lengths. Higher isoorientin and isovitexin conversion yields (>75%) were obtained using lauric acid in tert-amyl-alcohol as the reaction medium. (1)H and (13)C nuclear magnetic resonance spectroscopy analysis showed that, in the presence of CALB, acylation occurred at the isoorientin and isovitexin primary hydroxyl group of glucose moiety and only monoesters were detected. Introducing an acyl group into isoorientin and isovitexin significantly improved their lipophilicity but reduced their antiradical activity. PMID:23057589

Ma, Xiang; Yan, Rian; Yu, Shuqi; Lu, Yuyun; Li, Zhuo; Lu, Haohao

2012-10-31

207

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

PubMed

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

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

2014-12-01

208

CYP4 Enzymes as potential drug targets: focus on enzyme multiplicity, inducers and inhibitors, and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid ?-hydroxylase activities  

PubMed Central

The Cytochrome P450 4 (CYP4) family of enzymes in humans is comprised of thirteen isozymes that typically catalyze the ?-oxidation of endogenous fatty acids and eicosanoids. Several CYP4 enzymes can biosynthesize 20-hydroxyeicosatetraenoic acid or 20-HETE, an important signaling eicosanoid involved in regulation of vascular tone and kidney reabsorption. Additionally, accumulation of certain fatty acids is a hallmark of the rare genetic disorders, Refsum disease and X-ALD. Therefore, modulation of CYP4 enzyme activity, either by inhibition or induction, is a potential strategy for drug discovery. Here we review the substrate specificities, sites of expression, genetic regulation, and inhibition by exogenous chemicals of the human CYP4 enzymes, and discuss the targeting of CYP4 enzymes in the development of new treatments for hypertension, stroke, certain cancers and the fatty acid-linked orphan diseases. PMID:23688133

Edson, Katheryne Z.; Rettie, Allan E.

2014-01-01

209

DPPH radical scavenging activity of a mixture of fatty acids and peptide-containing compounds in a protein hydrolysate of Jatropha curcas seed cake.  

PubMed

Jatropha curcas, a tropical plant, has great potential commercial relevance as its seeds have high oil content. The seeds can be processed into high-quality biofuel producing seed cake as a byproduct. The seed cake, however, has not gotten much attention toward its potential usefulness. This work was aimed to determine the antioxidant activity of different fractions of a protein hydrolysate from J. curcas seed cake and to elucidate the molecular structures of the antioxidants. Seed cake was first processed into crude protein isolate and the protein was hydrolyzed by Neutrase. The hydrolysate obtained from 1 h of Neutrase hydrolysis showed the strongest antioxidant activity against DPPH radical (2,2-diphenyl-1-picrylhydrazyl). After a purification series of protein hydrolysate by liquid chromatography, chemicals acting as DPPH radical inhibitors were found to be a mixture of fatty acids, fatty acid derivatives, and a small amount of peptides characterized by mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. PMID:24191657

Phengnuam, Thanyarat; Goroncy, Alexander K; Rutherfurd, Shane M; Moughan, Paul J; Suntornsuk, Worapot

2013-12-01

210

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

PubMed Central

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

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

2014-01-01

211

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

PubMed

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

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

2014-04-01

212

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

213

OMEGA-3 FATTY ACID SUPPLEMENTATION AND SLEEP  

E-print Network

Previous research has found omega-3 fatty acid supplementation advantageous in reducing depressive symptoms. One of the central diagnostic symptoms of depression is sleep disturbance. Accordingly, this study was designed to examine the effects...

Prohaska, Jennifer A.

2008-10-24

214

Nrf2 affects the efficiency of mitochondrial fatty acid oxidation  

PubMed Central

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

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

2014-01-01

215

Dietary trans fatty acids and composition of human atheromatous plaques  

Microsoft Academic Search

Summary. Dietary fatty acids are incorporated into atheromatous plaques mainly in the form of cholesterol esters. Physicochemical properties of the plaque (e. g. mechanical strength) depend on its fatty acid composition. Trans isomers of unsaturated fatty acids (TFA) are known to reduce the availability of fatty acid precursors for the synthesis of anticoagulant PG 1 and PG 3 prostaglandins. The

Ewa Stachowska; Barbara Do??gowska; Dariusz Chlubek; Teresa Weso?owska; Kazimierz Ciechanowski; Piotr Gutowski; Halina Szumi?owicz; Rados?aw Turowski

2004-01-01

216

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

Microsoft Academic Search

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

Madhu Suman Rana; A. Tyagi; Sk Asraf Hossain

217

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

218

Cardiovascular benefits of omega-3 fatty acids  

Microsoft Academic Search

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

Clemens von Schacky; William S. Harris

2007-01-01

219

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

220

Effect of extracellular fatty acids on lipid metabolism in cultured rabbit articular chondrocytes  

SciTech Connect

Rabbit articular chondrocytes were cultured for 8 h in the presence of various concentrations (5-500 microM) of {sup 14}C oleic, {sup 14}C linoleic, and {sup 3H} arachidonic acids. The radioactive unsaturated fatty acids were incorporated into triacylglycerol (TG) and phosphatidylcholine (PC) in a concentration-dependent manner; more fatty acids were incorporated into TG than into PC, at higher concentrations of extracellular fatty acids. Among these fatty acids, arachidonic acid was incorporated into TG much more than into PC, in spite of a very low concentration of arachidonic acid in TG. After transfer of the labeled cells to maintenance medium, the radioactivity in TG declined rapidly and {sup 3}H arachidonic acid radioactivity in PC increased continuously during the chase time periods. Palmitoyl-unsaturated species were mainly formed in PC when cultured at a concentration of 5 microM of each fatty acid. However, when cultured at 500 microM, unsaturated-unsaturated species, specific for each unsaturated fatty acid were actively formed. These findings indicate that (1) fatty acid composition of TG and PC in articular chondrocytes is influenced by the degree of fatty acid supply, (2) formation and turnover of TG plays a role in fatty acid metabolism of cells, and (3) fatty acid pairing in PC is modulated by extracellular fatty acid concentrations.

Nagao, M.; Ishii, S.; Murata, Y.; Akino, T. (Sapporo Medical College (Japan))

1991-05-01

221

Is There a Fatty Acid Taste?  

PubMed Central

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

Mattes, Richard D.

2010-01-01

222

Fatty acid phytyl ester synthesis in chloroplasts of Arabidopsis.  

PubMed

During stress or senescence, thylakoid membranes in chloroplasts are disintegrated, and chlorophyll and galactolipid are broken down, resulting in the accumulation of toxic intermediates, i.e., tetrapyrroles, free phytol, and free fatty acids. Chlorophyll degradation has been studied in detail, but the catabolic pathways for phytol and fatty acids remain unclear. A large proportion of phytol and fatty acids is converted into fatty acid phytyl esters and triacylglycerol during stress or senescence in chloroplasts. We isolated two genes (PHYTYL ESTER SYNTHASE1 [PES1] and PES2) of the esterase/lipase/thioesterase family of acyltransferases from Arabidopsis thaliana that are involved in fatty acid phytyl ester synthesis in chloroplasts. The two proteins are highly expressed during senescence and nitrogen deprivation. Heterologous expression in yeast revealed that PES1 and PES2 have phytyl ester synthesis and diacylglycerol acyltransferase activities. The enzymes show broad substrate specificities and can employ acyl-CoAs, acyl carrier proteins, and galactolipids as acyl donors. Double mutant plants (pes1 pes2) grow normally but show reduced phytyl ester and triacylglycerol accumulation. These results demonstrate that PES1 and PES2 are involved in the deposition of free phytol and free fatty acids in the form of phytyl esters in chloroplasts, a process involved in maintaining the integrity of the photosynthetic membrane during abiotic stress and senescence. PMID:22623494

Lippold, Felix; vom Dorp, Katharina; Abraham, Marion; Hölzl, Georg; Wewer, Vera; Yilmaz, Jenny Lindberg; Lager, Ida; Montandon, Cyrille; Besagni, Céline; Kessler, Felix; Stymne, Sten; Dörmann, Peter

2012-05-01

223

Fatty Acid Metabolism, the Central Nervous System, and Feeding  

Microsoft Academic Search

A potential role for fatty acid metabolism in the regulation of energy balance in the brain or in the periphery has been considered only recently. Fatty acid synthase (FAS) catalyzes the synthesis of long-chain fatty acids, whereas the breakdown of fatty acids by ?-oxidation is regulated by carnitine palmitoyltransferase-1, the rate-limiting enzyme for the entry of fatty acids into the

Gabriele V. Ronnett; Amy M. Kleman; Eun-Kyoung Kim; Leslie E. Landree; Yajun Tu

2006-01-01

224

Functional characterization of flax fatty acid desaturase FAD2 and FAD3 isoforms expressed in yeast reveals a broad diversity in activity.  

PubMed

With 45 % or more oil content that contains more than 55 % alpha linolenic (LIN) acid, linseed (Linum usitatissimum L.) is one of the richest plant sources of this essential fatty acid. Fatty acid desaturases 2 (FAD2) and 3 (FAD3) are the main enzymes responsible for the ?12 and ?15 desaturation in planta. In linseed, the oilseed morphotype of flax, two paralogous copies, and several alleles exist for each gene. Here, we cloned three alleles of FAD2A, four of FAD2B, six of FAD3A, and seven of FAD3B into a pYES vector and transformed all 20 constructs and an empty construct in yeast. The transformants were induced in the presence of oleic (OLE) acid substrate for FAD2 constructs and linoleic (LIO) acid for FAD3. Conversion rates of OLE acid into LIO acid and LIO acid into LIN acid were measured by gas chromatography. Conversion rate of FAD2 exceeded that of FAD3 enzymes with FAD2B having a conversion rate approximately 10 % higher than FAD2A. All FAD2 isoforms were active, but significant differences existed between isoforms of both FAD2 enzymes. Two FAD3A and three FAD3B isoforms were not functional. Some nonfunctional enzymes resulted from the presence of nonsense mutations causing premature stop codons, but FAD3B-C and FAD3B-F seem to be associated with single amino acid changes. The activity of FAD3A-C was more than fivefold greater than the most common isoform FAD3A-A, while FAD3A-F was fourfold greater. Such isoforms could be incorporated into breeding lines to possibly further increase the proportion of LIN acid in linseed. PMID:24522837

Radovanovic, Natasa; Thambugala, Dinushika; Duguid, Scott; Loewen, Evelyn; Cloutier, Sylvie

2014-07-01

225

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

226

Indentification and Localization of the Fatty Acids in Haemophilus parainfluenzae  

PubMed Central

Haemophilus parainfluenzae was capable of synthesizing 22 fatty acids. These fatty acids were equivalent to 4% of the bacterial dry weight. These fatty acids were localized in the membrane-wall complex, which contained the respiratory pigments, the quinone, and the phospholipids. The fatty acids which could be extracted with organic solvents comprised 86% of the total fatty acids of the cell. These fatty acids were distributed as 98% in the phospholipids and 1.9% in the neutral lipids, of which 0.5% were free fatty acids. Palmitic, palmitoleic, oleic, and vaccenic acids comprised 72% of the total fatty acids and were found almost exclusively in the phospholipids. The phospholipids also contained the cyclopropane fatty acids. The neutral lipids contained significant proportions of the odd-numbered branched and straight-chain fatty acids. The principal free fatty acids were n-dodecanoic and pentadecenoic acids. The nonextractable wall complex contained 14% of the total fatty acids. These wall fatty acids were rendered soluble only after saponification. The wall fraction contained all of the ?-hydroxymyristic acid and most of the myristoleic and pentadecenoic acids. The significance of the distribution of fatty acids between nonesterified, neutral lipid, phospholipid, and nonextractible wall remains to be determined. PMID:6025415

White, David C.; Cox, Richard H.

1967-01-01

227

Iron translocation by free fatty acids.  

PubMed Central

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

Qian, M. W.; Eaton, J. W.

1991-01-01

228

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

Microsoft Academic Search

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

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

2009-01-01

229

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

230

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

PubMed Central

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

Parolini, Cinzia; Bj?rndal, Bodil; Holm, Sverre; Bohov, Pavol; Halvorsen, Bente; Brattelid, Trond; Manzini, Stefano; Ganzetti, Giulia S.; Dellera, Federica; Nygard, Ottar K.; Aukrust, Pal; Sirtori, Cesare R.; Chiesa, Giulia; Berge, Rolf K.

2013-01-01

231

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

PubMed

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

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

2013-04-01

232

Hypothalamic-pituitary-adrenal axis activation and immune regulation in heat-stressed sheep after supplementation with polyunsaturated fatty acids.  

PubMed

The aim of this study was to assess the effects of supplementation with polyunsaturated fatty acids from different sources on immune regulation and hypothalamic-pituitary-adrenal (HPA) axis activation in heat-stressed sheep. The experiment was carried out during the summer 2012. Thirty-two Comisana ewes were divided into 4 groups (8 sheep/group): (1) supplemented with whole flaxseed (FS); (2) supplemented with Ascophyllum nodosum (AG); (3) supplemented with a combination of flaxseed and A. nodosum (FS+AG); and (4) control (C; no supplementation). On d 22 of the experiment, cortisol concentrations in sheep blood were measured after an injection of ACTH. Cellular immune response was evaluated by intradermic injection of phytohemagglutinin (PHA) at 0, 15, and 30 d of the trial. Humoral response to ovalbumin (OVA) was measured at 0, 15, and 30 d. At 0, 15, and 30 d of the experiment, blood samples were collected from each ewe to determine production of T-helper (Th)1 cytokines (IL-12 and IFN-?), and Th2 cytokines (IL-10, IL-4, IL-13), and concentrations of heat shock proteins (HSP) 70 and 90. Ewes supplemented with flaxseed alone had greater cortisol concentrations and a longer-lasting cell-mediated immune response compared with ewes in the control and other groups. Anti-OVA IgG concentrations increased in all groups throughout the trial, even though ewes in the FS+AG group had the lowest anti-OVA IgG concentrations at 15 d. The level of IL-10 increased in all groups throughout the experiment; the FS+AG group had the lowest IL-13 concentration at 15 and 30 d. The concentration of HSP 70 increased in AG ewes at the end of the experiment and decreased in FS ewes, whereas that of HSP 90 increased in FS ewes compared with FS+AG ewes. Flaxseed supplementation was found to influence in vivo HPA activation in heat-stressed sheep, resulting in increased cortisol concentrations, probably to meet increased energy demand for thermoregulation. Flaxseed supplementation also supported Th1 response via a complex cross-talk between IL-10, IL-12, and IFN-? production. PMID:24792803

Caroprese, M; Ciliberti, M G; Annicchiarico, G; Albenzio, M; Muscio, A; Sevi, A

2014-07-01

233

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

PubMed

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

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

2014-04-01

234

Specific bile acids inhibit hepatic fatty acid uptake  

PubMed Central

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

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

2012-01-01

235

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

236

Omega3 Fatty Acids in the Treatment of Psychiatric Disorders  

Microsoft Academic Search

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

Malcolm Peet; Caroline Stokes

2005-01-01

237

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. PMID:23844377

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

2013-01-01

238

Fatty acid compositions of six wild edible mushroom species.  

PubMed

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

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

2013-01-01

239

AMPK-independent pathways regulate skeletal muscle fatty acid oxidation  

PubMed Central

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

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

2008-01-01

240

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

241

New applications for fatty acids and derivatives  

Microsoft Academic Search

The early development of the American fatty acid industry during 1900–1920 is usually associated with the use of stearic acid\\u000a in candles for lighting purposes. Today, the use of stearic acid in candle manufacture continues; the volume consumed for\\u000a this application is not small, but the use is for ornamental, decorative or festival purposes, only incidentally for emergency\\u000a lighting purposes.

M. Weiss; R. Rosberg; N. O. V. Sonntag; S. Eng

1979-01-01

242

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

243

A Dual Function ?-Dioxygenase-Peroxidase and NAD+ Oxidoreductase Active Enzyme from Germinating Pea Rationalizing ?-Oxidation of Fatty Acids in Plants12  

PubMed Central

An enzyme with fatty acid ?-oxidation activity (49 nkat mg?1; substrate: lauric acid) was purified from germinating pea (Pisum sativum) by a five-step procedure to apparent homogeneity. The purified protein was found to be a 230-kD oligomer with two dominant subunits, i.e. a 50-kD subunit with NAD+ oxidoreductase activity and a 70-kD subunit, homolog to a pathogen-induced oxygenase, which in turn shows significant homology to animal cyclooxygenase. On-line liquid chromatography-electrospray ionization-tandem mass spectrometry revealed rapid ?-oxidation of palmitic acid incubated at 0°C with the purified ?-oxidation enzyme, leading to (R)-2-hydroperoxypalmitic acid as the major product together with (R)-2-hydroxypalmitic acid, 1-pentadecanal, and pentadecanoic acid. Inherent peroxidase activity of the 70-kD fraction decreased the amount of the (R)-2-hydroperoxy product rapidly and increased the level of (R)-2-hydroxypalmitic acid. Incubations at room temperature accelerated the decline toward the chain-shortened aldehyde. With the identification of the dual function ?-dioxygenase-peroxidase (70-kD unit) and the related NAD+ oxidoreductase (50-kD unit) we provided novel data to rationalize all steps of the classical scheme of ?-oxidation in plants. PMID:10938370

Saffert, Alexander; Hartmann-Schreier, Jenny; Schon, Astrid; Schreier, Peter

2000-01-01

244

Effect of very long chain fatty acids on peroxisomal ?-oxidation in primary rat hepatocyte cultures  

Microsoft Academic Search

Previous studies have demonstrated that certain high fat diets can induce peroxisomal fatty acid ?-oxidation in rodent liver\\u000a and that this may be due to their content oftrans 22?1 fatty acids. In this study we have examined the effects ofcis andtrans 22?1 fatty acids (erucic and brassidic) and oleic acid (18?1) on palmitoyl-CoA oxidation, carnitine acetyltransferase and\\u000a carnitine palmitoyltransferase activities

Erling N. Christiansen; Tim J. B. Gray; Brian G. Lake

1985-01-01

245

Effects of squalene/squalane on dopamine levels, antioxidant enzyme activity, and fatty acid composition in the striatum of Parkinson's disease mouse model.  

PubMed

Active oxygen has been implicated in the pathogenesis of Parkinson's disease (PD); therefore, antioxidants have attracted attention as a potential way to prevent this disease. Squalene, a natural triterpene and an intermediate in the biosynthesis of cholesterol, is known to have active oxygen scavenging activities. Squalane, synthesized by complete hydrogenation of squalene, does not have active oxygen scavenging activities. We examined the effects of oral administration of squalene or squalane on a PD mouse model, which was developed by intracerebroventricular injection of 6-hydroxydopamine (6-OHDA). Squalene administration 7 days before and 7 days after one 6-OHDA injection prevented a reduction in striatal dopamine (DA) levels, while the same administration of squalane enhanced the levels. Neither squalene nor squalane administration for 7 days changed the levels of catalase, glutathione peroxidase, or superoxide dismutase activities in the striatum. Squalane increased thiobarbituric acid reactive substances, a marker of lipid peroxidation, in the striatum. Both squalane and squalene increased the ratio of linoleic acid/linolenic acid in the striatum. These results suggest that the administration of squalene or squalane induces similar changes in the composition of fatty acids and has no effect on the activities of active oxygen scavenging enzymes in the striatum. However, squalane increases oxidative damage in the striatum and exacerbates the toxicity of 6-OHDA, while squalene prevents it. The effects of squalene or squalane treatment in this model suggest their possible uses and risks in the treatment of PD. PMID:23357814

Kabuto, Hideaki; Yamanushi, Tomoko T; Janjua, Najma; Takayama, Fusako; Mankura, Mitsumasa

2013-01-01

246

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

PubMed

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

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

2013-05-01

247

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

PubMed Central

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

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

2014-01-01

248

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

PubMed

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

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

2014-01-01

249

Variability in fatty acids and fatty aldehydes in different organs of two prosobranch gastropod mollusks  

Microsoft Academic Search

The distribution of fatty acids and fatty aldehydes of total lipids in mantle, foot and digestive gland of two prosobranch gastropod mollusks, Bellamya bengalensis and Pila globosa, from India were studied. The individual volatile compounds, e.g., acids and aldehydes, were separated by serially coupled capillary columns with different polarity stationary phase and identified by gas chromatography-mass spectrometry. Saturated fatty acids

K. K Misra; I Shkrob; S Rakshit; V. M Dembitsky

2002-01-01

250

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

PubMed Central

Background Cyclopropane fatty acids (CPA) have been found in certain gymnosperms, Malvales, Litchi and other Sapindales. The presence of their unique strained ring structures confers physical and chemical properties characteristic of unsaturated fatty acids with the oxidative stability displayed by saturated fatty acids making them of considerable industrial interest. While cyclopropenoid fatty acids (CPE) are well-known inhibitors of fatty acid desaturation in animals, CPE can also inhibit the stearoyl-CoA desaturase and interfere with the maturation and reproduction of some insect species suggesting that in addition to their traditional role as storage lipids, CPE can contribute to the protection of plants from herbivory. Results Three genes encoding cyclopropane synthase homologues GhCPS1, GhCPS2 and GhCPS3 were identified in cotton. Determination of gene transcript abundance revealed differences among the expression of GhCPS1, 2 and 3 showing high, intermediate and low levels, respectively, of transcripts in roots and stems; whereas GhCPS1 and 2 are both expressed at low levels in seeds. Analyses of fatty acid composition in different tissues indicate that the expression patterns of GhCPS1 and 2 correlate with cyclic fatty acid (CFA) distribution. Deletion of the N-terminal oxidase domain lowered GhCPS's ability to produce cyclopropane fatty acid by approximately 70%. GhCPS1 and 2, but not 3 resulted in the production of cyclopropane fatty acids upon heterologous expression in yeast, tobacco BY2 cell and Arabidopsis seed. Conclusions In cotton GhCPS1 and 2 gene expression correlates with the total CFA content in roots, stems and seeds. That GhCPS1 and 2 are expressed at a similar level in seed suggests both of them can be considered potential targets for gene silencing to reduce undesirable seed CPE accumulation. Because GhCPS1 is more active in yeast than the published Sterculia CPS and shows similar activity when expressed in model plant systems, it represents a strong candidate gene for CFA accumulation via heterologous expression in production plants. PMID:21612656

2011-01-01

251

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

PubMed Central

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

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

2010-01-01

252

Essential fatty acids and phenolic acids from extracts and leachates of southern cattail ( Typha domingensis P.)  

Microsoft Academic Search

We have been able to isolate several phytotoxic compounds from aqueous extracts and leachates of cattails (Typha domingensis) using activated charcoal as an absorbant, followed by successive extraction with organic solvents, analysis by GC\\/MS, and structural elucidation by NMR spectroscopy when possible. The phytotoxins were identified as essential fatty acids (linoleic acid and ?-linolenic acid) and phenolic compounds of known

Maria T Gallardo-Williams; Cherie L Geiger; Joseph A Pidala; Dean F Martin

2002-01-01

253

Trans fatty acids and weight gain  

Microsoft Academic Search

Increasing rates of obesity have stimulated research into possible contributing factors, including specific dietary components such as trans fatty acids (TFAs). This review considers the evidence for an association between TFA intake and weight gain. It concludes that there is limited but consistent evidence from epidemiological studies, and from a primate model, that increased TFA consumption may result in a

A K Thompson; A-M Minihane; C M Williams

2011-01-01

254

Fatty acid compositions in local sea cucumber  

Microsoft Academic Search

Fatty acid profile from crude extracts of local sea cucumber Stichopus chloronotus was determined using gas chromatography (GC) technique. The extracts were prepared separately in methanol, ethanol, phosphate buffer saline (PBS), and distilled water as part of our study to look at the affinity of these solvents in extracting the lipid from sea cucumber. The PBS and distilled water extractions

B. D. Fredalina; B. H. Ridzwan; A. A. Zainal Abidin; M. A. Kaswandi; H. Zaiton; I. Zali; P. Kittakoop; A. M. Mat Jais

1999-01-01

255

21 CFR 172.860 - Fatty acids.  

...aldrin (RA) between 10 and 25, using the gas chromatographic-electron capture method prescribed in paragraph (c)(3) of this...ibr_locations.html. (3) The gas chromatographic-electron capture method for testing fatty acids for chick-edema...

2014-04-01

256

Fatty acid composition of California grown almonds.  

PubMed

Eight almond (Prunus dulcis L.) cultivars from 12 different California counties, collected during crop years 2004 to 2005 and 2005 to 2006, were extracted with petroleum ether. The extracts were subjected to GC-MS analyses to determine fatty acid composition of soluble lipids. Results indicated palmitic (C16:0), oleic (C18:1), linoleic (C18:2), and alpha-linolenic (C18:3) acid, respectively, accounted for 5.07% to 6.78%, 57.54% to 73.94%, 19.32% to 35.18%, and 0.04% to 0.10%; of the total lipids. Oleic and linoleic acid were inversely correlated (r=-0.99, P= 0.05) and together accounted for 91.16% to 94.29% of the total soluble lipids. Statistically, fatty acid composition was significantly affected by cultivar and county. PMID:19021789

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

2008-11-01

257

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

SciTech Connect

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

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

2013-11-15

258

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

PubMed

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

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

2014-01-01

259

Immunomodulation by Polyunsaturated Fatty Acids: Mechanisms and Effects  

Microsoft Academic Search

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

Thomas M. Stulnig

2003-01-01

260

Essential fatty acids in visual and brain development  

Microsoft Academic Search

Essential fatty acids are structural components of all tissues and are indispensable for cell membrane synthesis; the brain,\\u000a retina and other neural tissues are particularly rich in long-chain polyunsaturated fatty acids (LC-PUFA). These fatty acids\\u000a serve as specific precursors for eicosanoids, which regulate numerous cell and organ functions. Recent human studies support\\u000a the essential nature of n-3 fatty acids in

Ricardo Uauy; Dennis R. Hoffman; Patricio Peirano; David G. Birch; Eileen E. Birch

2001-01-01

261

Cloning and functional characterisation of polyunsaturated fatty acid elongases of marine and freshwater teleost fish.  

PubMed

Enzymes that lengthen the carbon chain of polyunsaturated fatty acids are key to the biosynthesis of the highly unsaturated fatty acids, arachidonic, eicosapentaenoic and docosahexaenoic acids from linoleic and alpha-linolenic acids. A Mortierella alpina cDNA polyunsaturated fatty acid elongase sequence identified mammalian, amphibian, zebrafish and insect expressed sequence tags (ESTs) in GenBank. Consensus primers were designed in conserved motifs and used to isolate full length cDNA from livers of several fish species by Rapid Amplification of cDNA Ends (RACE). The amplified cDNAs encoded putative open reading frames (ORFs) of 288-294 amino acids that were highly conserved among the fish species. Heterologous expression in yeast, Saccharomyces cerevisiae, demonstrated that all of the ORFs encoded elongases with the ability to lengthen polyunsaturated fatty acid substrates with chain lengths from C18 to C22 and also monounsaturated fatty acids, but not saturated fatty acids. There were differences in the functional competence of the elongases from different fish species. Most of the fish elongases showed a pattern of activity towards different fatty acid substrates in the rank order C18>C20>C22, although the tilapia and turbot elongases had similar activity towards 18:4n-3 and 20:5n-3. The fish elongases generally showed greater activity or similar activities with n-3 than with n-6 homologues, with the exception of the cod enzyme which was more active towards n-6 fatty acids. PMID:16183312

Agaba, Morris K; Tocher, Douglas R; Zheng, Xiaozhong; Dickson, Cathryn A; Dick, James R; Teale, Alan J

2005-11-01

262

Fatty acid metabolism in young oysters, Crassostrea gigas : Polyunsaturated fatty acids  

Microsoft Academic Search

Tetraselmis suecica andDunaliella tertiolecta were grown for 24 hr in the presence of14C sodium bicarbonate and then fed separately to batches of juvenile oysters,Crassostrea gigas, for 3 days.D. tertiolecta contained fatty acids no longer than C18; 22?6?3 was absent inT. suecica. Analysis of the oyster fatty acids by radio gas chromatography (GC) showed that oysters were able to incorporate some

M. J. Waldock; D. L. Holland

1984-01-01

263

Plasma free fatty acid and lipoproteins as sources of polyunsaturated fatty acid for the brain  

Microsoft Academic Search

Polyunsaturated fatty acids (PUFA), which comprise 25–30% of the fatty acids in the human brain, are necessary for normal\\u000a brain development and function. PUFA cannot be synthesized de novo and must be supplied to the brain by the plasma. It is necessary to know the PUFA content and composition of the various\\u000a plasma lipids and lipoproteins in order to understand

Arthur A. Spector

2001-01-01

264

Fatty acid-regulated transcription factors in the liver.  

PubMed

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

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

2013-01-01

265

Fatty Acid-Regulated Transcription Factors in the Liver  

PubMed Central

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

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

2014-01-01

266

Fatty Acid Production from Amino Acids and ?-Keto Acids by Brevibacterium linens BL2†  

PubMed Central

Low concentrations of branched-chain fatty acids, such as isobutyric and isovaleric acids, develop during the ripening of hard cheeses and contribute to the beneficial flavor profile. Catabolism of amino acids, such as branched-chain amino acids, by bacteria via aminotransferase reactions and ?-keto acids is one mechanism to generate these flavorful compounds; however, metabolism of ?-keto acids to flavor-associated compounds is controversial. The objective of this study was to determine the ability of Brevibacterium linens BL2 to produce fatty acids from amino acids and ?-keto acids and determine the occurrence of the likely genes in the draft genome sequence. BL2 catabolized amino acids to fatty acids only under carbohydrate starvation conditions. The primary fatty acid end products from leucine were isovaleric acid, acetic acid, and propionic acid. In contrast, logarithmic-phase cells of BL2 produced fatty acids from ?-keto acids only. BL2 also converted ?-keto acids to branched-chain fatty acids after carbohydrate starvation was achieved. At least 100 genes are potentially involved in five different metabolic pathways. The genome of B. linens ATCC 9174 contained these genes for production and degradation of fatty acids. These data indicate that brevibacteria have the ability to produce fatty acids from amino and ?-keto acids and that carbon metabolism is important in regulating this event. PMID:15528496

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

2004-01-01

267

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2010 CFR

...2010-07-01 false Triethanolamine salts of fatty acids. 721.3629...721.3629 Triethanolamine salts of fatty acids. (a) Chemical...generically as triethanolamine salts of fatty acids (PMN Nos...present a risk of injury to human health, the employer must...

2010-07-01

268

40 CFR 721.3629 - Triethanolamine salts of fatty acids.  

Code of Federal Regulations, 2011 CFR

...2011-07-01 false Triethanolamine salts of fatty acids. 721.3629...721.3629 Triethanolamine salts of fatty acids. (a) Chemical...generically as triethanolamine salts of fatty acids (PMN Nos...present a risk of injury to human health, the employer must...

2011-07-01

269

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

Federal Register 2010, 2011, 2012, 2013

...EPA-HQ-OPP-2009-0061; FRL-8852-2] Polyoxyalkylated Glycerol Fatty Acid Esters; Tolerance Exemption...tolerance for residues of polyoxyalkylated glycerol fatty acid esters; the mono-, di...oxide, also known as polyoxyalkylated glycerol fatty acid esters, when used as...

2010-11-24

270

Free Fatty Acids and the Flavor of Dairy Products  

Microsoft Academic Search

Studies in our laboratory have been aimed at the quantitative deternfination and sensory evaluation of free fatty acids in dairy products. Quantitative methods have been developed for free fatty acids in milk, butter, cheeses, and anhydrous milk fat; and sensory evaluation has aided in reveal- ing the relative importance of free fatty acids in these products. Flavor panel re- sults

D. D. Bills; R. A. Scanlan; R. C. Lindsay; Lois Sather

1969-01-01

271

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

PubMed Central

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

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

2006-01-01

272

Comparison of Rapid Methods for Analysis of Bacterial Fatty Acids  

PubMed Central

When rapid gas-liquid chromatography methods for determination of bacterial fatty acids were compared, results showed that saponification was required for total fatty acid analysis. Transesterification with boron-trihalide reagents (BF3-CH3OH, BCl3-CH3OH) caused extensive degradation of cyclopropane acids and was less effective than saponification in releasing cellular hydroxy fatty acids. Digestion of cells with tetramethylammonium hydroxide was unsatisfactory because of extraneous gas-liquid chromatography peaks and because of lower recovery of branched-chain and hydroxy fatty acids. A simple, rapid saponification procedure which can be used for total cellular fatty acid analysis of freshly grown cells is described. PMID:4844271

Moss, C. Wayne; Lambert, M. A.; Merwin, W. H.

1974-01-01

273

Peroxisomal very long-chain fatty acid [beta]-oxidation in human skin fibroblasts: activity in Zellweger syndrome and other peroxisomal disorders  

Microsoft Academic Search

Since very long-chain fatty acids with a chain length of 24 carbons or more are known to accumulate in tissues and body fluids from patients with the cerebro-hepato-renal (Zellweger) syndrome, infantile Refsum disease, neonatal adrenoleukodystrophy and X-linked adrenoleukodystrophy, we studied very long-chain fatty acid oxidation in cultured skin fibroblasts from these patients. In this paper, we report that in accordance

R. J. A. Wanders; C. W. T. van Roermund; M. J. A. van Wijland; J. Heikoop; R. B. H. Schutgens; A. W. Schram; J. M. Tager; H. van den Bosch; B. T. Poll-Thé; J. M. Saudubray; H. W. Moser; A. B. Moser

1987-01-01

274

Enhanced cAMP\\/PKA pathway by seabuckthorn fatty acids in aged rats  

Microsoft Academic Search

Seabuckthorn fatty acids were extracted by crushing and centrifuging from china seabuckthorn fruit. We detected cyclic nucleotides concentration in serum of different stages in aged rats (from 16 to 21 months), cyclic nucleotides concentration, PKA activity and PDE activity in hepatic tissue in aged rats by seabuckthorn fatty acids. Our data showed that the serum cAMP concentration decreased, accompany with

Rui Hu; Bingxiang Yuan; Xiazhen Wei; Limei Zhao; Junjie Tang; Dong Chen

2007-01-01

275

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

NASA Astrophysics Data System (ADS)

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

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

276

Escherichia coli cyclopropane fatty acid synthase.  

PubMed

Escherichia coli fatty acid cyclopropane synthase (CFAS) was overproduced and purified as a His6-tagged protein. This recombinant enzyme is as active as the native enzyme with a Km of 90 microm for S-AdoMet and a specific activity of 5 x 10(-2) micromol.min(-1).mg(-1). The enzyme is devoid of organic or metal cofactors and is unable to catalyze the wash-out of the methyl protons of S-AdoMet to the solvent, data that do not support the ylide mechanism. Inactivation of the enzyme by 5,5'-dithiobis-(2-nitrobenzoic acid) (DTNB), a pseudo first-order process with a rate constant of 1.2 m(-1).s(-1), is not protected by substrates. Graphical analysis of the inactivation by DTNB revealed that only one cysteine is responsible for the inactivation of the enzyme. The three strictly conserved Cys residues among cyclopropane synthases, C139, C176 and C354 of the E. coli enzyme, were mutated to serine. The relative catalytic efficiency of the mutants were 16% for C139S, 150% for C176S and 63% for C354S. The three mutants were inactivated by DTNB at a rate comparable to the rate of inactivation of the His6-tagged wild-type enzyme, indicating that the Cys responsible for the loss of activity is not one of the conserved residues. Therefore, none of the conserved Cys residues is essential for catalysis and cannot be involved in covalent catalysis or general base catalysis. The inactivation is probably the result of steric hindrance, a phenomenon irrelevant to catalysis. It is very likely that E. coli CFAS operates via a carbocation mechanism, but the base and nucleophile remain to be identified. PMID:15606764

Courtois, Fabienne; Guérard, Christine; Thomas, Xavier; Ploux, Olivier

2004-12-01

277

Complementation analysis of fatty acid oxidation disorders.  

PubMed Central

We assayed [9,10(n)-3H]palmitate oxidation by fibroblast monolayers from patients with fatty acid oxidation disorders. Activities in the different disorders were (percent control): short-chain acyl-coenzyme A (CoA) dehydrogenase deficiency (115%), medium chain acyl-CoA dehydrogenase deficiency (18%), long-chain acyl-CoA dehydrogenase deficiency (28%), multiple acyl-CoA dehydrogenation disorder, mild and severe variants (49% and 7%), and palmityl-carnitine transferase deficiency (4%). Multiple acyl-CoA dehydrogenation disorder, medium chain acyl-CoA dehydrogenase-deficient lines, and long-chain acyl-CoA dehydrogenase-deficient lines all complemented one another after polyethylene glycol fusion, with average activity increases of 31-83%. We detected two complementation groups in the severe multiple acyl-CoA dehydrogenation disorder lines, consistent with deficiencies of either electron transfer flavoprotein or electron transfer flavoprotein:ubiquinone oxidoreductase. The metabolic block in the latter cell lines is threefold more severe than in the former (P less than 0.001). No intragenic complementation was observed within either group. We assigned two patients with previously unreported severe multiple acyl-CoA dehydrogenation disorder to the electron transfer flavoprotein:ubiquinone oxido-reductase-deficient group. PMID:3793932

Moon, A; Rhead, W J

1987-01-01

278

The effect of variations in dietary fatty acids on the fatty acid composition of erythrocyte phosphatidyicholine and phosphatidylethanolamine in human  

Microsoft Academic Search

Human milk, or one of two formulas that derive their fat from vegetable oil, was fed to infants from birth until 4.5 to 6 months of age. Infants fed human milk received 2% of total fatty acids as 20 to 22 carbon polyunsaturated fatty acids. These fatty acids which are not found in vegetable oils, are synthesized by animals from

Jane C. Putnam; Susin E. Carlson; Phillip W. De Voe; Lewis A. Barness

279

Fatty Acid Composition and Volatile Constituents of Protaetia brevitarsis Larvae  

PubMed Central

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

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

2013-01-01

280

Omega3 fatty acids and heart failure  

Microsoft Academic Search

During the past three decades, the protective role of omega (n)-3 polyunsaturated fatty acids (PUFA), mainly eicosapentaenoic\\u000a acid and docosahexaenoic acid, in patients with coronary heart disease has been widely reported. The Gruppo Italiano per lo\\u000a Studio della Sopravvivenza nell’Infarto Miocardico-Heart Failure (GISSI-HF) study, a large-scale clinical trial, recently\\u000a showed that n-3 PUFA (850–882 mg\\/d) reduced mortality and admission to

Roberto Marchioli; Maria Giuseppina Silletta; Giacomo Levantesi; Raffaella Pioggiarella

2009-01-01

281

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

PubMed

Ammonolysis of fatty acids to the corresponding fatty acid amides is efficiently catalysed by Candida antartica lipase (Novozym 435). In the present paper lipase-catalysed synthesis of erucamide by ammonolysis of erucic acid and urea in organic solvent medium was studied and optimal conditions for fatty amides synthesis were established. In this process erucic acid gave 88.74 % pure erucamide after 48 hour and 250 rpm at 60 degrees C with 1:4 molar ratio of erucic acid and urea, the organic solvent media is 50 ml tert-butyl alcohol (2-methyl-2-propanol). This process for synthesis is economical as we used urea in place of ammonia or other amidation reactant at atmospheric pressure. The amount of catalyst used is 3 %. PMID:17898456

Awasthi, Neeraj Praphulla; Singh, R P

2007-01-01

282

Synthesis and release of fatty acids by human trophoblast cells in culture  

SciTech Connect

In order to determine whether placental cells can synthesize and release fatty acids, trophoblast cells from term human placentas were established in monolayer culture. The cells continued to secrete placental lactogen and progesterone and maintained specific activities of critical enzymes of triacylglycerol and phosphatidylcholine biosynthesis for 24 to 72 hr in culture. Fatty acid was rapidly synthesized from (/sup 14/C)acetate and released by the cells. Palmitoleic, palmitic, and oleic acids were the major fatty acids synthesized from (/sup 14/C)acetate and released. Small amounts of lauric, myristic, and stearic acids were also identified. (/sup 14/C)acetate was also incorporated into cellular triacylglycerol, phospholipid, and cholesterol, but radiolabeled free fatty acid did not accumulate intracellularly. In a pulse-chase experiment, cellular glycerolipids were labeled with (1-/sup 14/C)oleate; trophoblast cells then released /sup 14/C-labeled fatty acid into the media as the cellular content of labeled phospholipid and triacylglycerol decreased without intracellular accumulation of free fatty acid. Twenty percent of the /sup 14/C-label lost from cellular glycerolipid could not be recovered as a chloroform-extractable product, suggesting that some of the hydrolyzed fatty acid had been oxidized. These data indicate that cultured placenta trophoblast cells can release fatty acids that have either been synthesized de novo or that have been hydrolyzed from cellular glycerolipids. Trophoblast cells in monolayer culture should provide an excellent model for molecular studies of placental fatty acid metabolism and release.

Coleman, R.A.; Haynes, E.B.

1987-11-01

283

Cellular fatty acid composition of Plesiomonas shigelloides.  

PubMed Central

The cellular fatty acid compositions of 29 strains of Plesiomonas shigelloides and 5 strains of Aeromonas hydrophila were studied. The cellular fatty acid compositions of all the Plesiomonas strains were identical and characterized by the presence of hexadecanoate (16:0) (33%), hexadecenoate (16:1) (28%), octadecenoate (18:1) (9%), and octadecanoate (18:0) (6%). The cellular fatty acid composition of A. hydrophila was similar to that of the Plesiomonas strains, except that the former contained an average of 25% 16:0, 29% 16:1, 12% 18:1, and 2% 18:0 acids compared with 33, 28, 9, and 6%, respectively, for the latter. The percentage ratios of 16:1 to 16:0 and 18:1 to 18:0 could be used to differentiate P. shigelloides from A. hydrophila. These ratios were 0.8 and 1.5 for the former and 1.2 and 6.0 for the latter. PMID:2056045

Chou, S; Aldova, E; Kasatiya, S

1991-01-01

284

The peroxisomal enzyme L-PBE is required to prevent the dietary toxicity of medium-chain fatty acids.  

PubMed

Specific metabolic pathways are activated by different nutrients to adapt the organism to available resources. Although essential, these mechanisms are incompletely defined. Here, we report that medium-chain fatty acids contained in coconut oil, a major source of dietary fat, induce the liver ?-oxidation genes Cyp4a10 and Cyp4a14 to increase the production of dicarboxylic fatty acids. Furthermore, these activate all ?- and ?-oxidation pathways through peroxisome proliferator activated receptor (PPAR) ? and PPAR?, an activation loop normally kept under control by dicarboxylic fatty acid degradation by the peroxisomal enzyme L-PBE. Indeed, L-pbe(-/-) mice fed coconut oil overaccumulate dicarboxylic fatty acids, which activate all fatty acid oxidation pathways and lead to liver inflammation, fibrosis, and death. Thus, the correct homeostasis of dicarboxylic fatty acids is a means to regulate the efficient utilization of ingested medium-chain fatty acids, and its deregulation exemplifies the intricate relationship between impaired metabolism and inflammation. PMID:24075987

Ding, Jun; Loizides-Mangold, Ursula; Rando, Gianpaolo; Zoete, Vincent; Michielin, Olivier; Reddy, Janardan K; Wahli, Walter; Riezman, Howard; Thorens, Bernard

2013-10-17

285

Atherosclerosis, Dyslipidemia, and Inflammation: The Significant Role of Polyunsaturated Fatty Acids  

PubMed Central

Phospholipids play an essential role in cell membrane structure and function. The length and number of double bonds of fatty acids in membrane phospholipids are main determinants of fluidity, transport systems, activity of membrane-bound enzymes, and susceptibility to lipid peroxidation. The fatty acid profile of serum lipids, especially the phospholipids, reflects the fatty acid composition of cell membranes. Moreover, long-chain n-3 polyunsatured fatty acids decrease very-low-density lipoprotein assembly and secretion reducing triacylglycerol production. N-6 and n-3 polyunsatured fatty acids are the precursors of signalling molecules, termed “eicosanoids,” which play an important role in the regulation of inflammation. Eicosanoids derived from n-6 polyunsatured fatty acids have proinflammatory actions, while eicosanoids derived from n-3 polyunsatured fatty acids have anti-inflammatory ones. Previous studies showed that inflammation contributes to both the onset and progression of atherosclerosis: actually, atherosclerosis is predominantly a chronic low-grade inflammatory disease of the vessel wall. Several studies suggested the relationship between long-chain n-3 polyunsaturated fatty acids and inflammation, showing that fatty acids may decrease endothelial activation and affect eicosanoid metabolism. PMID:24049656

Dessì, Mariarita; Noce, Annalisa; Bertucci, Pierfrancesco; Manca di Villahermosa, Simone; Zenobi, Rossella; Castagnola, Veronica; Addessi, Eliana

2013-01-01

286

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

Microsoft Academic Search

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

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

2011-01-01

287

Recovery of fatty acid lights from still vapors  

Microsoft Academic Search

A fatty acids still operating primarily on coconut oil fatty acids has two condensers in series to condense the top product.\\u000a Nonetheless, until recently 1% to 2% of fatty acid lights normally passed through to the hot well. Here the caproic, caprylic\\u000a and capric acids dissolved in the warm water and these dissolved acids ultimately found their way to the

C. T. Atwood; C. L. Woody

1971-01-01

288

Hyperinsulinemia and skeletal muscle fatty acid trafficking.  

PubMed

We hypothesized that insulin alters plasma free fatty acid (FFA) trafficking into intramyocellular (im) long-chain acylcarnitines (imLCAC) and triglycerides (imTG). Overnight-fasted adults (n = 41) received intravenous infusions of [U-¹³C]palmitate (0400-0900 h) and [U-¹³C]oleate (0800-1400 h) to label imTG and imLCAC. A euglycemic-hyperinsulinemic (1.0 mU·kg fat-free mass?¹·min?¹) clamp (0800-1400 h) and two muscle biopsies (0900 h, 1400 h) were performed. The patterns of [U-¹³C]palmitate incorporation into imTG-palmitate and palmitoylcarnitine were similar to those we reported in overnight postabsorptive adults (saline control); the intramyocellular palmitoylcarnitine enrichment was not different from and correlated with imTG-palmitate enrichment for both the morning (r = 0.38, P = 0.02) and afternoon (r = 0.44, P = 0.006) biopsy samples. Plasma FFA concentrations, flux, and the incorporation of plasma oleate into imTG-oleate during hyperinsulinemia were ~1/10th of that observed in the previous saline control studies (P < 0.001). At the time of the second biopsy, the enrichment in oleoylcarnitine was <25% of that in imTG-oleate and was not correlated with imTG-oleate enrichment. The intramyocellular nonesterified fatty acid-palmitate-to-imTG-palmitate enrichment ratio was greater (P < 0.05) in women than men, suggesting that sex differences in intramyocellular palmitate trafficking may occur under hyperinsulinemic conditions. We conclude that plasma FFA trafficking into imTG during hyperinsulinemia is markedly suppressed, and these newly incorporated FFA fatty acids do not readily enter the LCAC preoxidative pools. Hyperinsulinemia does not seem to inhibit the entry of fatty acids from imTG pools that were labeled under fasting conditions, possibly reflecting the presence of two distinct imTG pools that are differentially regulated by insulin. PMID:23820622

Kanaley, Jill A; Shadid, Samyah; Sheehan, Michael T; Guo, ZengKui; Jensen, Michael D

2013-08-15

289

Densities of vegetable oils and fatty acids  

Microsoft Academic Search

Complete data for density as a function of temperature have been measured for a number of vegetable oils (crambe, rapeseed,\\u000a corn, soybean, milkweed, coconut, lesquerella), as well as eight fatty acids in the range C9 to C22 at temperatures from above their melting points to 110C (230F). The specific gravity and density measurements were performed\\u000a according to American Society for

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

1992-01-01

290

Cardiovascular Effects of Trans Fatty Acids  

Microsoft Academic Search

\\u000a The position of the double bond in the carbon chain of a fatty acid is indicated in several ways. When counted from the carboxyl\\u000a end (–COOH) of the molecule, the position (x) is denoted by the “?–x”-nomenclature, while the “n–x” classification is used when counting starts from the methyl end (–CH3). Thus, “n–3” means that the double bond is located

Ronald P. Mensink

291

Performance of sulfoxylated fatty acid methyl esters  

Microsoft Academic Search

Sulfoxidation of fatty acid methyl esters with SO2, O2, and ultraviolet light of appropriate wavelength has led to the synthesis of methyl esters sulfonates or sulfoxylates known\\u000a as ?-MES because of the possible random position of SO3 group in the alkyl chain. This work describes experimental measurements of physical properties such as solubility and viscosity\\u000a of sodium ?-MES water solutions.

Leon Cohen; Francisco Trujillo

1999-01-01

292

Saturated Very-Long-Chain Fatty Acids Promote Cotton Fiber and Arabidopsis Cell Elongation by Activating Ethylene Biosynthesis[W][OA  

PubMed Central

Fatty acids are essential for membrane biosynthesis in all organisms and serve as signaling molecules in many animals. Here, we found that saturated very-long-chain fatty acids (VLCFAs; C20:0 to C30:0) exogenously applied in ovule culture medium significantly promoted cotton (Gossypium hirsutum) fiber cell elongation, whereas acetochlor (2-chloro-N-[ethoxymethyl]-N-[2-ethyl-6-methyl-phenyl]-acetamide; ACE), which inhibits VLCFA biosynthesis, abolished fiber growth. This inhibition was overcome by lignoceric acid (C24:0). Elongating fibers contained significantly higher amounts of VLCFAs than those of wild-type or fuzzless-lintless mutant ovules. Ethylene nullified inhibition by ACE, whereas C24:0 was inactive in the presence of the ethylene biosynthesis inhibitor (l-[2-aminoethoxyvinyl]-glycine), indicating that VLCFAs may act upstream of ethylene. C24:0 induced a rapid and significant increase in ACO (for 1-aminocyclopropane-1-carboxylic acid oxidase) transcript levels that resulted in substantial ethylene production. C24:0 also promoted Ser palmitoyltransferase expression at a later stage, resulting in increased sphingolipid biosynthesis. Application of C24:0 not only stimulated Arabidopsis thaliana root cell growth but also complemented the cut1 phenotype. Transgenic expression of Gh KCS13/CER6, encoding the cotton 3-ketoacyl-CoA synthase, in the cut1 background produced similar results. Promotion of Arabidopsis stem elongation was accompanied by increased ACO transcript levels. Thus, VLCFAs may be involved in maximizing the extensibility of cotton fibers and multiple Arabidopsis cell types, possibly by activating ethylene biosynthesis. PMID:17993622

Qin, Yong-Mei; Hu, Chun-Yang; Pang, Yu; Kastaniotis, Alexander J.; Hiltunen, J. Kalervo; Zhu, Yu-Xian

2007-01-01

293

Unsaturated fatty acids, desaturases, and human health.  

PubMed

With the increasing concern for health and nutrition, dietary fat has attracted considerable attention. The composition of fatty acids in a diet is important since they are associated with major diseases, such as cancers, diabetes, and cardiovascular disease. The biosynthesis of unsaturated fatty acids (UFA) requires the expression of dietary fat-associated genes, such as SCD, FADS1, FADS2, and FADS3, which encode a variety of desaturases, to catalyze the addition of a double bond in a fatty acid chain. Recent studies using new molecular techniques and genomics, as well as clinical trials have shown that these genes and UFA are closely related to physiological conditions and chronic diseases; it was found that the existence of alternative transcripts of the desaturase genes and desaturase isoforms might affect human health and lipid metabolism in different ways. In this review, we provide an overview of UFA and desaturases associated with human health and nutrition. Moreover, recent findings of UFA, desaturases, and their associated genes in human systems are discussed. Consequently, this review may help elucidate the complicated physiology of UFA in human health and diseases. PMID:24460221

Lee, Hyungjae; Park, Woo Jung

2014-02-01

294

Lipidomics of oxidized polyunsaturated fatty acids  

PubMed Central

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

Massey, Karen A.; Nicolaou, Anna

2013-01-01

295

Production of hydroxylated fatty acids in genetically modified plants  

DOEpatents

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

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

2001-01-01

296

Inhibition by arachidonic acid and other fatty acids of dopamine uptake at the human dopamine transporter  

Microsoft Academic Search

It is known that arachidonic acid, in addition to promoting release of dopamine, can inhibit its transport. The present study provides preliminary information on structure–activity relationships for uptake inhibition by rotating disk voltammetry in human embryonic kidney-293 cells expressing the human dopamine transporter. Except for anandamide, all other fatty acids studied at a pretreatment concentration of 80 ?M caused significant

Nianhang Chen; Michael Appell; Janet L. Berfield; Maarten E. A. Reith

2003-01-01

297

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

MedlinePLUS

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

298

Overview of Omega-3 Fatty Acid Therapies  

PubMed Central

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

Bradberry, J. Chris; Hilleman, Daniel E.

2013-01-01

299

Temperature Affects Fatty Acids In Methylococcus Capsulatus  

NASA Technical Reports Server (NTRS)

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

Jahnke, Linda L.

1993-01-01

300

Separation of cis-fatty acids from saturated and trans-fatty acids by nanoporous polydicyclopentadiene membranes.  

PubMed

This article describes the separation of mixtures of fatty acid salts using a new organic solvent nanofiltration membrane based on polydicyclopentadiene (PDCPD). Mixtures of free fatty acids could not be separated by the membranes because they permeated at similar rates. When triisobutylamine was added to the fatty acids, the cis-fatty acid salts (oleic, petroselinic, vaccenic, linoleic, and linolenic acid) had slower permeation though the membranes than saturated (stearic acid) and trans-fatty acid (elaidic acid) salts. The reason for the difference in permeation was due to the formation of stable salt pairs between the amine and fatty acids that increased their cross-sectional areas. The fatty acid salts derived from saturated and trans-fatty acids were smaller than the critical area cutoff for the PDCPD membranes, so they readily permeated. In contrast, the fatty acid salts derived from the cis-fatty acids had critical areas larger than critical area cutoff of the PDPCD membranes and had slowed permeation. The partitioning coefficients of fatty acids and fatty acid salts were investigated to demonstrate that they were not responsible for the difference in permeation. The use of pressure was investigated to greatly accelerate the permeation through the membranes. For a solvent mixture of 35/65 (v/v) toluene/hexanes, the permeation of solvent was approximately 39 L m(-2) h(-1). This value is similar to values reported for permeation through membranes used in industry. The separation of a mixture of fatty acids based on the composition of soybean oil was investigated using pressure. The saturated fatty acid salts were almost completely removed from the cis-fatty acid salts when iBu(3)N was used as the amine to form the salt pairs. The separation of the cis-fatty acids found in soybean oil was investigated with Pr(3)N as the amine. The oleic acid salt (oleic acid has one cis double bond) preferentially permeated the membrane while the linoleic (two cis double bonds) and linolenic (three cis double bonds) salts were partly retained. The separation of fatty acids using membranes may have real applications in industry to purify fatty acids on a large scale. PMID:23281782

Gupta, Abhinaba; Bowden, Ned B

2013-02-01

301

The effects of unsaturated fatty acids on hepatic microsomal drug metabolism and cytochrome P-450  

PubMed Central

1. The effects of unsaturated fatty acids on drug-metabolizing enzymes in vitro were measured by using rat and rabbit hepatic 9000g supernatant fractions. 2. Unsaturated fatty acids inhibited the hepatic microsomal metabolism of `type I' drugs with inhibition increasing with unsaturation: arachidonic acid>linolenic acid>linoleic acid>oleic acid. Inhibition was independent of lipid peroxidation. Linoleic acid competitively inhibited the microsomal O-demethylation of p-nitroanisole and the N-demethylation of (+)-benzphetamine. 3. The hepatic microsomal metabolism of `type II' substrates, aniline and (?)-amphetamine, was not affected by unsaturated fatty acids. 4. The rate of reduction of p-nitrobenzoic acid and Neoprontosil was accelerated by unsaturated fatty acids. 5. Linoleic acid up to 3·5mm did not decelerate the generation of NADPH by rat liver soluble fraction, nor the activity of NADPH–cytochrome c reductase of rat liver microsomes. Hepatic microsomal NADPH oxidase activity was slightly enhanced by added linoleic acid. 6. No measurable disappearance of exogenously added linoleic acid occurred when this fatty acid was incubated with rat liver microsomes and an NADPH source. 7. The unsaturated fatty acids used in this study produced type I spectra when added to rat liver microsomes, and affected several microsomal enzyme activities in a manner characteristic of type I ligands. PMID:4390924

Di Augustine, Richard P.; Fouts, James R.

1969-01-01

302

Fatty Acid and Volatile Oil Compositions of Allomyrina dichotoma Larvae  

PubMed Central

Thirty-two different volatile oils were identified from Allomyrina dichotoma (A. dichotoma) larvae by gas chromatography/mass spectrometry (GC/MS). The major volatile components were 2,2,4-trimethyl-3-carboxyisopropyl pentanoic acid isobutyl ester (5.83%), phenol,2,6-bis(a,a-dimethyl ethyl)-4-(1-methyl-1-phenylethyl) (5.72%), heptacosane (5.49%) and phenol,2,4-bis(1-methyl-1-phenylethyl) (5.47%). The composition of the fatty acids in A. dichotoma larvae was also determined by gas chromatography (GC) and fourteen constituents were identified. Oleic acid (19.13%) was the most abundant fatty acid followed by palmitic acid (12.52%), palmitoleic acid (3.71%) and linoleic acid (2.08%) in 100 g of A. dichotoma larvae on a dry weight basis. The quantity of unsaturated fatty acids (64.00%) were higher than that of saturated ones (36.00%). The predominant fatty acids in A. dichotoma consist of monounsaturated fatty acid (MUFA, 57.70%) such as oleic acid, myristoleic acid and palmitoleic acid, followed by saturated fatty acids (36.00%) and polyunsaturated fatty acids (PUFA, 6.50%). In particular, the presence of essential fatty acids, such as linoleic (5.30%) and linolenic acid (0.40%) give A. dichotoma larvae considerable nutritional and functional value and it may be a useful source for food and/or industrial utilization. PMID:24471102

Youn, Kumju; Kim, Ji-Young; Yeo, Hyelim; Yun, Eun-Young; Hwang, Jae-Sam; Jun, Mira

2012-01-01

303

Efficient free fatty acid production in Escherichia coli using plant acyl-ACP thioesterases.  

PubMed

Microbial biosynthesis of fatty acid-like chemicals from renewable carbon sources has attracted significant attention in recent years. Free fatty acids can be used as precursors for the production of fuels or chemicals. Free fatty acids can be produced by introducing an acyl-acyl carrier protein thioesterase gene into Escherichia coli. The presence of the acyl-ACP thioesterase will break the fatty acid elongation cycle and release free fatty acid. Depending on their sequence similarity and substrate specificity, class FatA thioesterase is active on unsaturated acyl-ACPs and class FatB prefers saturated acyl group. Different acyl-ACP thioesterases have different degrees of chain length specificity. Although some of these enzymes have been characterized from a number of sources, information on their ability to produce free fatty acid in microbial cells has not been extensively examined until recently. In this study, we examined the effect of the overexpression of acyl-ACP thioesterase genes from Diploknema butyracea, Gossypium hirsutum, Ricinus communis and Jatropha curcas on free fatty acid production. In particular, we are interested in studying the effect of different acyl-ACP thioesterase on the quantities and compositions of free fatty acid produced by an E. coli strain ML103 carrying these constructs. It is shown that the accumulation of free fatty acid depends on the acyl-ACP thioesterase used. The strain carrying the acyl-ACP thioesterase gene from D. butyracea produced approximately 0.2g/L of free fatty acid while the strains carrying the acyl-ACP thioesterase genes from R. communis and J. curcas produced the most free fatty acid at a high level of more than 2.0 g/L at 48 h. These two strains accumulated three major straight chain free fatty acids, C14, C16:1 and C16 at levels about 40%, 35% and 20%, respectively. PMID:22001432

Zhang, Xiujun; Li, Mai; Agrawal, Arpita; San, Ka-Yiu

2011-11-01

304

Oxalic acid alleviates chilling injury in peach fruit by regulating energy metabolism and fatty acid contents.  

PubMed

The effects of postharvest oxalic acid (OA) treatment on chilling injury, energy metabolism and membrane fatty acid content in 'Baifeng' peach fruit stored at 0°C were investigated. Internal browning was significantly reduced by OA treatment in peaches. OA treatment markedly inhibited the increase of ion leakage and the accumulation of malondialdehyde. Meanwhile, OA significantly increased the contents of adenosine triphosphate and energy charge in peach fruit. Enzyme activities of energy metabolism including H(+)-adenosine triphosphatase, Ca(2+)-adenosine triphosphatase, succinic dehydrogenase and cytochrome C oxidase were markedly enhanced by OA treatment. The ratio of unsaturated/saturated fatty acid in OA-treated fruit was significantly higher than that in control fruit. These results suggest that the alleviation in chilling injury by OA may be due to enhanced enzyme activities related to energy metabolism and higher levels of energy status and unsaturated/saturated fatty acid ratio. PMID:24837925

Jin, Peng; Zhu, Hong; Wang, Lei; Shan, Timin; Zheng, Yonghua

2014-10-15

305

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

PubMed Central

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

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

2013-01-01

306

Mechanisms of Peroxisome Proliferation by Perfluorooctanoic Acid and Endogenous Fatty Acids  

Microsoft Academic Search

1.The effects of endogenous fatty acids and perfluorooctanoic acid (PFOA) and its analogs on peroxisomal acyl CoA oxidase (ACO) and microsomal laurate hydroxylase (LH) activities were evaluated in primary cultures of rat hepatocytes and activation of peroxisome proliferator-activated receptor ? (PPAR?) in CV-1 cells. The rank order for the stimulation of ACO activity in hepatocytes for selected compounds was PFOA>>octanoic

Urusa Intrasuksri; Shamina M. Rangwala; O’Brien; Daniel J. Noonan; Dennis R. Feller

1998-01-01

307

Trans fatty acids and cardiovascular health: research completed?  

PubMed

This review asks the question if further research on trans fatty acids and cardiovascular health is needed. We therefore review the evidence from human studies on trans fatty acids and cardiovascular health, and provide a quantitative review of effects of trans fatty acid intake on lipoproteins. The results show that the effect of industrially produced trans fatty acids on heart health seen in observational studies is larger than predicted from changes in lipoprotein concentrations. There is debate on the effect of ruminant trans fatty acids and cardiovascular disease. Of special interest is conjugated linoleic acid (CLA), which is produced industrially for sale as supplements. Observational studies do not show higher risks of cardiovascular disease with higher intakes of ruminant trans fatty acids. However, CLA, industrial and ruminant trans fatty acids all raise plasma low-density lipoprotein and the total to high-density lipoprotein ratio. Gram for gram, all trans fatty acids have largely the same effect on blood lipoproteins. In conclusion, the detrimental effects of industrial trans fatty acids on heart health are beyond dispute. The exact size of effect will remain hard to determine. Further research is warranted on the effects of ruminant trans fatty acids and CLA on cardiovascular disease and its risk factors. PMID:23531781

Brouwer, I A; Wanders, A J; Katan, M B

2013-05-01

308

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

ERIC Educational Resources Information Center

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

Raz, Raanan; Gabis, Lidia

2009-01-01

309

A dual action of saturated fatty acids on electrical activity in rat pancreatic ?-cells. Role of volume-regulated anion channel and KATP channel currents  

PubMed Central

Abstract Free fatty acids (FFAs) exert complex actions on pancreatic ?-cells. Typically, an initial potentiation of insulin release is followed by a gradual impairment of ?-cell function, the latter effect being of possible relevance to hyperlipidaemia in type 2 diabetes mellitus. The molecular actions of FFAs are poorly understood. The present study investigated the acute effects of saturated FFAs on electrophysiological responses of rat pancreatic ?-cells. Membrane potential and KATP channel activity were recorded using the perforated patch technique. Volume-regulated anion channel (VRAC) activity was assessed from conventional whole-cell recordings. Cell volume regulation was measured using a video-imaging technique. Addition of octanoate caused a transient potentiation of glucose-induced electrical activity, followed by a gradual hyperpolarisation and a prolonged inhibition of electrical activity. Octanoate caused an initial increase in VRAC activity followed by a secondary inhibition coinciding with increased KATP channel activity. Similar effects were observed with palmitate and 2-bromopalmitate whereas butyrate was virtually ineffective. Octanoate and palmitate also exerted a dual effect on electrical activity evoked by tolbutamide. Octanoate significantly attenuated cell volume regulation in hypotonic solutions, consistent with VRAC inhibition. It is concluded that medium and long chain FFAs have a dual action on glucose-induced electrical activity in rat pancreatic ?-cells: an initial stimulatory effect followed by a secondary inhibition. These effects appear to be the result of reciprocal actions on VRAC and KATP channel currents, and could contribute towards the stimulatory and inhibitory actions of FFAs on pancreatic ?-cell function. PMID:21242256

Best, L; Jarman, E; Brown, P D

2011-01-01

310

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

PubMed Central

Background Saturated fatty acids are thought to be of relevance for the development of non-alcoholic fatty liver disease and obesity. However, the underlying mechanisms are poorly understood. In previous studies we found that food-derived carbohydrates such as fructose alter the intestinal serotonergic system while inducing fatty liver disease in mice. Here, we examined the effect of fatty acid quantity (11% versus 15%) and quality (saturated, monounsaturated, or polyunsaturated fatty acids) on hepatic fat accumulation, intestinal barrier and the intestinal serotonergic system. Methods C57BL/6 mice had free access to diets enriched with one of the three fatty acids or standard diet, for 8 weeks. In an additional experiment mice were fed diets enriched with saturated, monounsaturated fatty acids or standard diet supplemented with tryptophan (0.4 g/(kg.d), 8 weeks) or not. Hepatic fat accumulation, small intestinal barrier impairment and components of the serotonergic system were measured with RT-PCR, western blot or immunoassays. For statistical analysis t-test and one-way ANOVA with Tukey’s post hoc test and Bartlett’s test for equal variances was used. Results Hepatic triglycerides, liver weight and liver to body weight ratio were significantly changed depending on the fat quality but not fat quantity. In contrast, fat quantity but not quality decreased the expression of the tight junction proteins occludin and claudin-1 in the small intestine. These changes seemed to result in enhanced portal vein endotoxin concentrations and fatty liver disease after feeding diet enriched with saturated and monounsaturated fatty acids but not polyunsaturated fatty acids. Neither fatty acid quantity nor quality significantly influenced the intestinal serotonergic system. Similarly, tryptophan supplementation had no impact on small intestinal barrier or fatty liver disease. Conclusion In conclusion, diets rich in saturated or monounsaturated fatty acids promote the development of fatty liver disease in mice, likely by a dysfunction of the small intestinal mucosal barrier. PMID:24321090

2013-01-01

311

Omega3 fatty acids from fish oils and cardiovascular disease  

Microsoft Academic Search

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

Darren J. Holub; Bruce J. Holub

2004-01-01

312

The composition of furan fatty acids in the crayfish  

Microsoft Academic Search

Capillary gas chromatography-mass spectrometry (GC-MS) analysis of the sterol ester fatty acid methyl esters of the crayfish\\u000a hepatopancreas revealed the presence of at least 30 kinds of unusual furan fatty acids (F acids), which accounted for 28.49%\\u000a of the total sterol ester fatty acids. On the other hand, only small amounts were found in triacylglycerols (0.5%) and phospholipids\\u000a (0.7%). Among

Kazuo Ishii; Haruo Okajima; Tsuyoshi Koyamatsu; Youji Okada; Hiroshi Watanabe

1988-01-01

313

Fatty Acids in the Causation and Therapy of Metabolic Syndrome  

Microsoft Academic Search

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

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

314

Role of Fatty Acid Binding Proteins and Long Chain Fatty Acids in Modulating Nuclear Receptors and Gene Transcription  

Microsoft Academic Search

Abnormal energy regulation may significantly contribute to the pathogenesis of obesity, diabetes mellitus, cardiovascular\\u000a disease, and cancer. For rapid control of energy homeostasis, allosteric and posttranslational events activate or alter activity\\u000a of key metabolic enzymes. For longer impact, transcriptional regulation is more effective, especially in response to nutrients\\u000a such as long chain fatty acids (LCFA). Recent advances provide insights into

Friedhelm Schroeder; Anca D. Petrescu; Huan Huang; Barbara P. Atshaves; Avery L. McIntosh; Gregory G. Martin; Heather A. Hostetler; Aude Vespa; Danilo Landrock; Kerstin K. Landrock; H. Ross Payne; Ann B. Kier

2008-01-01

315

Improvement of Medium Chain Fatty Acid Content and Antimicrobial Activity of Coconut Oil via Solid-State Fermentation Using a Malaysian Geotrichum candidum  

PubMed Central

Coconut oil is a rich source of beneficial medium chain fatty acids (MCFAs) particularly lauric acid. In this study, the oil was modified into a value-added product using direct modification of substrate through fermentation (DIMOSFER) method. A coconut-based and coconut-oil-added solid-state cultivation using a Malaysian lipolytic Geotrichum candidum was used to convert the coconut oil into MCFAs-rich oil. Chemical characteristics of the modified coconut oils (MCOs) considering total medium chain glyceride esters were compared to those of the normal coconut oil using ELSD-RP-HPLC. Optimum amount of coconut oil hydrolysis was achieved at 29% moisture content and 10.14% oil content after 9 days of incubation, where the quantitative amounts of the modified coconut oil and MCFA were 0.330?mL/g of solid media (76.5% bioconversion) and 0.175?mL/g of solid media (53% of the MCO), respectively. MCOs demonstrated improved antibacterial activity mostly due to the presence of free lauric acid. The highest MCFAs-rich coconut oil revealed as much as 90% and 80% antibacterial activities against Staphylococcus aureus and Escherichia coli, respectively. The results of the study showed that DIMOSFER by a local lipolytic G. candidum can be used to produce MCFAs as natural, effective, and safe antimicrobial agent. The produced MCOs and MCFAs could be further applied in food and pharmaceutical industries. PMID:23971051

Khoramnia, Anahita; Ebrahimpour, Afshin; Ghanbari, Raheleh; Ajdari, Zahra; Lai, Oi-Ming

2013-01-01

316

Fatty Acid Composition of the Complex Lipids of Staphylococcus aureus During the Formation of the Membrane-bound Electron Transport System  

PubMed Central

In Staphylococcus aureus, 64 fatty acids could be separated by gas-liquid chromatography. The fatty acids consisted of normal, iso, and anteiso saturated fatty acids of from 10 to 21 carbon atoms. Of the total fatty acids, 2 to 4% were normal, iso, and anteiso monoenoic fatty acids. Positional isomers of the normal monoenoic fatty acids could be detected. The fatty acids could be extracted, leaving 1 to 2% of the total fatty acids in the residue. The proportions of the fatty acids in the residue and the total lipids differed significantly. The lipid extract contained less than 0.12% free fatty acid. Between 5 and 10% of the lipid fatty acids were associated with neutral lipids. The majority of the fatty acids were associated with the complex lipids: mono- and diglucosyl diglyceride, phosphatidyl glycerol, lysyl phosphatidyl glycerol, and cardiolipin. The proportions of the fatty acids changed markedly between bacteria grown anaerobically (no membrane-bound electron transport system) and those grown aerobically (containing a functional electron transport system). In each of the complex lipids, the proportions of the fatty acids, as well as the magnitude and direction of change in the molar quantity of the fatty acids per bacterium, changed dramatically between these growth conditions. Since the glucosyl diglycerides and phospholipids were formed from the same pool of diglyceride intermediates, the marked differences in fatty acids indicate that acyl transferase activities must be an important part of complex lipid metabolism in S. aureus. PMID:5669897

White, David C.; Frerman, Frank E.

1968-01-01

317

DOCOSAHEXAENOIC ACID AND ARACHIDONIC ACID PREVENT ESSENTIAL FATTY ACID DEFICIENCY AND HEPATIC STEATOSIS  

PubMed Central

Objectives Essential fatty acids are important for growth, development, and physiologic function. Alpha-linolenic acid and linoleic acid are the precursors of docosahexaenoic and arachidonic acid, respectively, and have traditionally been considered the essential fatty acids. However, we hypothesized that docosahexaenoic acid and arachidonic acid can function as the essential fatty acids. Methods Using a murine model of essential fatty acid deficiency and consequent hepatic steatosis, we provided mice with varying amounts of docosahexaenoic and arachidonic acids to determine whether exclusive supplementation of docosahexaenoic and arachidonic acids could prevent essential fatty acid deficiency and inhibit or attenuate hepatic steatosis. Results Mice supplemented with docosahexaenoic and arachidonic acids at 2.1% or 4.2% of their calories for 19 days had normal liver histology and no biochemical evidence of essential fatty acid deficiency, which persisted when observed after 9 weeks. Conclusion Supplementation of sufficient amounts of docosahexaenoic and arachidonic acids alone without alpha-linolenic and linoleic acids meets essential fatty acid requirements and prevents hepatic steatosis in a murine model. PMID:22038210

Le, Hau D.; Meisel, Jonathan A.; de Meijer, Vincent E.; Fallon, Erica M.; Gura, Kathleen M.; Nose, Vania; Bistrian, Bruce R.; Puder, Mark

2012-01-01

318

[The fatty acids of membranes of erythrocytes in women with ischemic heart disease under effect of statins].  

PubMed

The technique of evaluation of metabolism of fatty acids in vivo consists in detection of content of fatty acids in phospholipids of membranes of erythrocytes. The fatty acids are received with food, through synthesis on liver from carbohydrates and by katabolism of very long-chain polyolefinic fatty acids of food in peroxisomes of hepatocytes (oxidation, saturation and desaturation). In position sn-1 phospholipids more often than palmitic fatty acid (14%) stearic fatty acid is esterified (21% of all fatty acids). The palmitic, stearic and lignoceric saturated fatty acids are esterified into sn-1 phospholipids as 2:3:1. The simvastatin (80 mg per day) increased content of margarine, tricosanoic and hexacosanoic fatty acids by decrease of level of palmitic fatty acid. The ratio omega-3 polyolefinic fatty acids/omega-6 polyolefinic fatty acids reliably increased. The statins increase content of omega-3 polyolefinic fatty acids. In practice, it is necessary to differentiate the terms "atherosclerosis" and "atheromatosis". The atherosclerosis is a syndrome of intracellular deficiency of polyolefinic fatty acids, derangement of function of cells in vivo under decrease of biological availability for all cells (absorption blockage). The atheromatosis is such most significant clinically symptom of atherosclerosis as accumulation of non-saturated and polyolefinic fatty acids in pool of collection and utilization of biological "garbage" from blood plasma, in intima of elastic type arteries. The statins activate absorption of low density lipoproteins by cells and normalize biological availability of polyolefinic fatty acids which have a positive effect under atherosclerosis and on formation of atheromatosis. PMID:25080788

Dyga?, A M; Kotlovski?, M Iu; Kirichenko, D A; Iakimovich, I Iu; Trereshina, D S; Kotlovski?, Iu V; Titiov, V N

2014-03-01

319

Structural and functional organization of the animal fatty acid synthase.  

PubMed

The entire pathway of palmitate synthesis from malonyl-CoA in mammals is catalyzed by a single, homodimeric, multifunctional protein, the fatty acid synthase. Each subunit contains three N-terminal domains, the beta-ketoacyl synthase, malonyl/acetyl transferase and dehydrase separated by a structural core from four C-terminal domains, the enoyl reductase, beta-ketoacyl reductase, acyl carrier protein and thiosterase. The kinetics and specificities of the substrate loading reaction catalyzed by the malonyl/acetyl transferase, the condensation reaction catalyzed by beta-ketoacyl synthase and chain-terminating reaction catalyzed by the thioesterase ensure that intermediates do not leak off the enzyme, saturated chains exclusively are elongated and palmitate is released as the major product. Only in the fatty acid synthase dimer do the subunits adopt conformations that facilitate productive coupling of the individual reactions for fatty acid synthesis at the two acyl carrier protein centers. Introduction of a double tagging and dual affinity chromatographic procedure has permitted the engineering and isolation of heterodimeric fatty acid synthases carrying different mutations on each subunit. Characterization of these heterodimers, by activity assays and chemical cross-linking, has been exploited to map the functional topology of the protein. The results reveal that the two acyl carrier protein domains engage in substrate loading and condensation reactions catalyzed by the malonyl/acetyl transferase and beta-ketoacyl synthase domains of either subunit. In contrast, the reactions involved in processing of the beta-carbon atom, following each chain elongation step, together with the release of palmitate, are catalyzed by the cooperation of the acyl carrier protein with catalytic domains of the same subunit. These findings suggest a revised model for the fatty acid synthase in which the two polypeptides are oriented such that head-to-tail contacts are formed both between and within subunits. PMID:12689621

Smith, Stuart; Witkowski, Andrzej; Joshi, Anil K

2003-07-01

320

Nitroalkene fatty acids mediate activation of Nrf2/ARE-dependent and PPAR?-dependent transcription by distinct signaling pathways and with significantly different potencies†  

PubMed Central

Naturally occurring nitroalkene fatty acids (NAs) derived from oleic (NO2-OA) and linoleic (NO2-LA) acids mediate a variety of cellular responses. We examined the signaling pathways involved in NA activation of Nrf2/ARE-dependent versus PPAR?/PPRE-dependent transcription in human MCF7 breast cancer cells. Additionally, we compared the relative potencies of NO2-OA and NO2-LA in activating these two transcriptional programs. Here it is demonstrated that, in addition to the direct adduct formation of NA with the Nrf2 inhibitory protein, Keap1, shown by others, NA activation of Nrf2/ARE-mediated transcription results from increased nuclear Nrf2 levels and depends upon activation of the PI3K/AKT and PKC, but not ERK and JNK MAPK, signaling pathways. Examination of the relationship between NA stimulation of the Nrf2/ARE versus PPAR?/PPRE transcriptional programs revealed concentration-dependent activation of distinct signaling pathways that were readily distinguished by selective attenuation of Nrf2/ARE-dependent, but not PPAR?-dependent, transcription by inhibitors of PI3K and PKC. Moreover, measurable, statistically significant activation of PPAR?/PPRE-dependent transcription occurred at nanomolar concentrations of NAs—the 12-NO2 isomer of NO2-LA showing the most potent activity—whereas significant activation of Nrf2/ARE-dependent transcription occurred at much higher NA concentrations (? 3 micromolar) with the NO2-OA isomers the most potent. These findings have implications for the physiological roles of NAs suggesting that, at concentrations likely to be encountered in vivo, their direct activation of PPAR? transcription will dominate over their electrophilic activation of Nrf2 antioxidant/protective responses. PMID:21827153

Bates, Darcy J. P.; Smitherman, Pamela K.; Townsend, Alan J.; King, S. Bruce; Morrow, Charles S.

2011-01-01

321

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

PubMed Central

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

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

2012-01-01

322

AMP-activated Protein Kinase ?2 Subunit Is Required for the Preservation of Hepatic Insulin Sensitivity by n-3 Polyunsaturated Fatty Acids  

PubMed Central

OBJECTIVE The induction of obesity, dyslipidemia, and insulin resistance by high-fat diet in rodents can be prevented by n-3 long-chain polyunsaturated fatty acids (LC-PUFAs). We tested a hypothesis whether AMP-activated protein kinase (AMPK) has a role in the beneficial effects of n-3 LC-PUFAs. RESEARCH DESIGN AND METHODS Mice with a whole-body deletion of the ?2 catalytic subunit of AMPK (AMPK?2?/?) and their wild-type littermates were fed on either a low-fat chow, or a corn oil-based high-fat diet (cHF), or a cHF diet with 15% lipids replaced by n-3 LC-PUFA concentrate (cHF+F). RESULTS Feeding a cHF diet induced obesity, dyslipidemia, hepatic steatosis, and whole-body insulin resistance in mice of both genotypes. Although cHF+F feeding increased hepatic AMPK?2 activity, the body weight gain, dyslipidemia, and the accumulation of hepatic triglycerides were prevented by the cHF+F diet to a similar degree in both AMPK?2?/? and wild-type mice in ad libitum-fed state. However, preservation of hepatic insulin sensitivity by n-3 LC-PUFAs required functional AMPK?2 and correlated with the induction of adiponectin and reduction in liver diacylglycerol content. Under hyperinsulinemic-euglycemic conditions, AMPK?2 was essential for preserving low levels of both hepatic and plasma triglycerides, as well as plasma free fatty acids, in response to the n-3 LC-PUFA treatment. CONCLUSIONS Our results show that n-3 LC-PUFAs prevent hepatic insulin resistance in an AMPK?2-dependent manner and support the role of adiponectin and hepatic diacylglycerols in the regulation of insulin sensitivity. AMPK?2 is also essential for hypolipidemic and antisteatotic effects of n-3 LC-PUFA under insulin-stimulated conditions. PMID:20693347

Jelenik, Tomas; Rossmeisl, Martin; Kuda, Ondrej; Jilkova, Zuzana Macek; Medrikova, Dasa; Kus, Vladimir; Hensler, Michal; Janovska, Petra; Miksik, Ivan; Baranowski, Marcin; Gorski, Jan; Hébrard, Sophie; Jensen, Thomas E.; Flachs, Pavel; Hawley, Simon; Viollet, Benoit; Kopecky, Jan

2010-01-01

323

Localization of chloroplastic fatty acid synthesis de novo in the stroma.  

PubMed Central

The synthesis of fatty acids de novo from [2-14C]malonyl-CoA was studied in fractions from lettuce (Lactuca sativa) and pea (Pisum sativum) chloroplasts. When lettuce chloroplasts were subjected to osmotic lysis, disintegration through a Yeda press and high-speed centrifugation, essentially all of the fatty-acid-synthetic activity was found to be soluble. The distribution of the activity in various chloroplast fractions was similar to that of soluble marker enzymes such as ribulose-1,5-bisphosphate carboxylase and NADP+-linked glyceraldehyde-3-phosphate dehydrogenase. Marked differences were apparent in the quality of products from fatty acid synthesis de novo in the various fractions of chloroplasts. Thus soluble fractions produced predominantly stearate, whereas those containing membranes produced a greater proportion of palmitate. In pea chloroplasts, osmotic lysis released almost all of the fatty acid synthetase into the stromal fraction. In this instance, no major alterations in the products of fatty acid synthesis were observed. The fatty-acid-synthetic activity of the stromal fraction was still soluble after prolonged ultracentrifugation. The results show clearly the soluble nature of fatty acid synthesis de novo in lettuce and pea chloroplasts. Thus fatty acid synthesis measured in microsomal fractions from such plant tissues is not due to the presence of chloroplastic membranes. PMID:3994672

Walker, K A; Harwood, J L

1985-01-01

324

Polyphenol fatty acid esters as serine protease inhibitors: a quantum-chemical QSAR analysis.  

PubMed

We investigated the ability of polyphenol fatty acid esters to inhibit the activity of serine proteases trypsin, thrombin, elastase and urokinase. Potent protease inhibition in micromolar range was displayed by rutin and rutin derivatives esterified with medium and long chain, mono- and polyunsaturated fatty acids (1e-m), followed by phloridzin and esculin esters with medium and long fatty acid chain length (2a-d, 3a-d), while unmodified compounds showed only little or no effect. QSAR study of the compounds tested provided the most significant parameters for individual inhibition activities, i.e. number of hydrogen bond donors for urokinase, molecular volume for thrombin, and solvation energy for elastase. According to the statistical analysis, the action of elastase inhibitors is opposed to those of urokinase and thrombin. Cluster analysis showed two groups of compounds: original polyphenols together with rutin esters with short fatty acid chain length and rutin esters with long fatty acid chain length. PMID:21981000

Viskupicova, Jana; Danihelova, Martina; Majekova, Magdalena; Liptaj, Tibor; Sturdik, Ernest

2012-12-01

325

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

Microsoft Academic Search

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

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

2004-01-01

326

Marine polyunsaturated fatty acids and cancer therapy  

PubMed Central

Polyunsaturated fatty acids (PUFAs) derived from marine sources, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), are widely consumed as supplements within the community. However, the use of marine PUFAs in a therapeutic context is also increasing in patients receiving treatment for a range of cancer types. On balance, the literature suggests that marine PUFAs have potential as an effective adjuvant to chemotherapy treatment, may have direct anticancer effects, and may help ameliorate some of the secondary complications associated with cancer. Although a range of doses have been trialled, it would appear that supplementation of fish oil (>3?g per day) or EPA/DHA (>1?g EPA and >0.8?g DHA per day) is associated with positive clinical outcomes. However, further research is still required to determine the mechanisms via which marine PUFAs are mediating their effects. This review summarises our current understanding of marine PUFAs and cancer therapy. PMID:23299528

Vaughan, V C; Hassing, M-R; Lewandowski, P A

2013-01-01

327

Odd- and branched-chain fatty acids in milk fat - characteristic and health properties.  

PubMed

This review analyzes the current state of knowledge on odd- and branched-chain fatty acids present in milk fat. Special attention is devoted to the characteristic, synthesis in ruminants, factors affecting their content in milk fat and pro-health properties of these compounds. The group of odd- and branched-chain fatty acids includes mainly saturated fatty acids with one or more methyl branches in the iso or anteiso position. These fatty acids are largely derived from ruminal bacteria and they have been transferred to ruminant tissue (milk and meat). For that reason they have been used as biomarkers of rumen fermentation. Odd- and branched-chain fatty acids are exogenous products for humans, and therefore have specific properties. The results of research from recent decades show that odd- and branched-chain fatty acids have anti-cancer activity. Branched-chain fatty acids may reduce the incidence of necrotizing enterocolitis. Additionally, these compounds have a beneficial effect on proper tissue function and on functioning and development of the infant gut, whereas odd-chain fatty acids are considered as biomarkers of milk fat intake by humans. So far, not all the mechanisms of activity of these compounds are known thoroughly. They should be more carefully studied for application of their biological effects in prevention and treatment. PMID:25228507

Adamska, Agata; Rutkowska, Jaros?awa

2014-01-01

328

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

PubMed

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

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

2012-07-01

329

Liver Fatty Acid Binding Protein and Obesity  

PubMed Central

While low levels of unesterified long chain fatty acids (LCFAs) are normal metabolic intermediates of dietary and endogenous fat, LCFAs are also potent regulators of key receptors/enzymes, and at high levels become toxic detergents within the cell. Elevated levels of LCFAs are associated with diabetes, obesity, and metabolic syndrome. Consequently, mammals evolved fatty acid binding proteins (FABPs) that bind/sequester these potentially toxic free fatty acids in the cytosol and present them for rapid removal in oxidative (mitochondria, peroxisomes) or storage (endoplasmic reticulum, lipid droplets) organelles. Mammals have a large (15 member) family of FABPs with multiple members occurring within a single cell type. The first described FABP, liver-FABP (L-FABP, or FABP1), is expressed in very high levels (2-5% of cytosolic protein) in liver as well as intestine and kidney. Since L-FABP facilitates uptake and metabolism of LCFAs in vitro and in cultured cells, it was expected that abnormal function or loss of L-FABP would reduce hepatic LCFA uptake/oxidation and thereby increase LCFAs available for oxidation in muscle and/or storage in adipose. This prediction was confirmed in vitro with isolated liver slices and cultured primary hepatocytes from L-FABP gene-ablated mice. Despite unaltered food consumption when fed a control diet ad libitum, the L-FABP null mice exhibited age- and sex-dependent weight gain and increased fat tissue mass. The obese phenotype was exacerbated in L-FABP null mice pair-fed a high fat diet. Taken together with other findings, these data suggest that L-FABP could have an important role in preventing age- or diet-induced obesity. PMID:20537520

Atshaves, B.P.; Martin, G.G.; Hostetler, H.A.; McIntosh, A.L.; Kier, A.B.; Schroeder, F.

2010-01-01

330

Applications of cellular fatty acid analysis.  

PubMed Central

More than ever, new technology is having an impact on the tools of clinical microbiologists. The analysis of cellular fatty acids by gas-liquid chromatography (GLC) has become markedly more practical with the advent of the fused-silica capillary column, computer-controlled chromatography and data analysis, simplified sample preparation, and a commercially available GLC system dedicated to microbiological applications. Experience with applications in diagnostic microbiology ranges from substantial success in work with mycobacteria, legionellae, and nonfermentative gram-negative bacilli to minimal involvement with fungi and other nonbacterial agents. GLC is a good alternative to other means for the identification of mycobacteria or legionellae because it is rapid, specific, and independent of other specialized testing, e.g., DNA hybridization. Nonfermenters show features in their cellular fatty acid content that are useful in identifying species and, in some cases, subspecies. Less frequently encountered nonfermenters, including those belonging to unclassified groups, can ideally be characterized by GLC. Information is just beginning to materialize on the usefulness of cellular fatty acids for the identification of gram-positive bacteria and anaerobes, despite the traditional role of GLC in detecting metabolic products as an aid to identification of anaerobes. When species identification of coagulase-negative staphylococci is called for, GLC may offer an alternative to biochemical testing. Methods for direct analysis of clinical material have been developed, but in practical and economic terms they are not yet ready for use in the clinical laboratory. Direct analysis holds promise for detecting markers of infection due to an uncultivable agent or in clinical specimens that presently require cultures and prolonged incubation to yield an etiologic agent. PMID:1747860

Welch, D F

1991-01-01

331

Metabolic Activity of Fatty Acid-Oxidizing Bacteria and the Contribution of Acetate, Propionate, Butyrate, and CO2 to Methanogenesis in Cattle Waste at 40 and 60°C  

PubMed Central

The quantitative contribution of fatty acids and CO2 to methanogenesis was studied by using stirred, 3-liter bench-top digestors fed on a semicontinuous basis with cattle waste. The fermentations were carried out at 40 and 60°C under identical loading conditions (6 g of volatile solids per liter of reactor volume per day, 10-day retention time). In the thermophilic digestor, acetate turnover increased from a prefeeding level of 16 ?M/min to a peak (49 ?M/min) 1 h after feeding and then gradually decreased. Acetate turnover in the mesophilic digestor increased from 15 to 40 ?M/min. Propionate turnover ranged from 2 to 5.2 and 1.5 to 4.5 ?M/min in the thermophilic and mesophilic digestors, respectively. Butyrate turnover (0.7 to 1.2 ?M/min) was similar in both digestors. The proportion of CH4 produced via the methyl group of acetate varied with time after feeding and ranged from 72 to 75% in the mesophilic digestor and 75 to 86% in the thermophilic digestor. The contribution from CO2 reduction was 24 to 29% and 19 to 27%, respectively. Propionate and butyrate turnover accounted for 20% of the total CH4 produced. Acetate synthesis from CO2 was greatest shortly after feeding and was higher in the thermophilic digestor (0.5 to 2.4 ?M/min) than the mesophilic digestor (0.3 to 0.5 ?M/min). Counts of fatty acid-degrading bacteria were related to their turnover activity. PMID:16345789

Mackie, Roderick I.; Bryant, Marvin P.

1981-01-01

332

Polyunsaturated fatty acids as putative cognitive enhancers.  

PubMed

Polyunsaturated essential fatty acids (PUFAs) play a pivotal role in mediating cognitive, learning, and memory functions. We propose that PUFAs directly affect the neuronal membrane. PUFAs serve to stabilize and protect the structure and functions of the neuronal membrane. PUFAs exert many effects on the brain with respect to physiology, brain biochemistry, and disorders of the central nervous system. Many of these functions have effects at the cognitive level. This summary demonstrates that a deficiency in brain PUFAs will lead to cognitive deficits, while supplementation of PUFAs can rehabilitate cognitive deficits, as manifested in attention deficit hyperactivity disorder, stress/anxiety, and aging. PMID:22800804

Yehuda, S

2012-10-01

333

Lipid and fatty acid biosynthesis by Rhodotorula minuta  

Microsoft Academic Search

Demand for fatty acids is increasing at an annual rate of 17%, due to their increased use in the oleochemical and transport\\u000a industries. Presently, vegetable oils are the major source of fatty acids, whereas lipids with fatty acids similar to those\\u000a of some vegetable oils have been reported to be synthesized by oleaginous microorganisms. In the present study, the culturing

Vani Saxena; C. D. Sharma; S. D. Bhagat; V. S. Saini; D. K. Adhikari

1998-01-01

334

Relationship between central and peripheral fatty acids in humans  

PubMed Central

Background In recent years the physiological and pathological importance of fatty acids in both the periphery and central nervous system (CNS) has become increasingly apparent. However surprisingly limited research has been conducted comparing the fatty acid composition of central and peripheral lipid stores. Methods The present study compared the distribution of polyunsaturated (PUFA), as well as specific saturated (SFA) and monounsaturated (MUFA) fatty acids in the whole blood and cerebrospinal fluid (CSF) of humans. Gas chromatography with flame ionization detection was used to determine the fatty acid profiles of twenty-eight matched CSF and whole blood samples. Multiple linear regression modeling, controlling for age, was used to identify significant relationships. Results A significant positive relationship was seen between whole blood total omega-3 fatty acids and the CSF omega-3 subfractions, docosapentaenoic acid (DPA) (P?=?0.019) and docosahexaenoic acid (DHA) (P?=?0.015). A direct association was also observed between the whole blood and CSF omega-6 PUFA, arachidonic acid (AA) (P?=?0.045). Interestingly an inverse association between central and peripheral oleic acid was also found (P?=?0.045). Conclusions These findings indicate a relationship between central and peripheral fatty acids of varying degrees of unsaturation and chain length and support the view that some systemic fatty acids are likely to cross the human blood brain barrier (BBB) and thereby influence central fatty acid concentrations. PMID:23710642

2013-01-01

335

Fatty acids profiles of some Spanish wild vegetables  

Microsoft Academic Search

Polyunsaturated fatty acids play an important role in human nutrition, being associated with several health benefits. The analyzed vegetables, in spite of its low fat content, lower than 2%, present a high proportion of polyunsaturated fatty acids of n-3, n-6 and n-9 series, such as ?-linolenic, linoleic and oleic acids, respectively. Wild edible plants contain in general a good balance

P Morales; ICFR Ferreira; AM Carvalho; MC Sánchez-Mata; M Cámara; J Tardío

2012-01-01

336

Novel branched-chain fatty acids in certain fish oils.  

PubMed

Methyl-branched fatty acids, which are usually minor components (equal or less than 0.1%) in fish oils, were concentrated in the non-urea-complexing fraction along with polyunsaturated fatty acids during the enrichment of omega-3 fatty acids from certain fish oils via the urea complexation process. The methyl-branched fatty acids in the omega-3 polyunsaturated fatty acid concentrates, which were prepared from three fish body oils, were characterized by gas chromatography and gas chromatography/mass spectrometry. Among the major branched-chain fatty acids expected and identified were the known isoprenoid acids--mainly 4,8,12-trimethyltridecanoic, pristanic, and phytanic--and the well-known iso and anteiso structures. Two novel phytol-derived multimethyl-branched fatty acids, 2,2,6,10,14-pentamethylpentadecanoic and 2,3,7,11,15-pentamethylhexadecanoic, were identified in redfish (Sebastes sp.) oil. These two fatty acids were absent in oils from menhaden (Brevoortia tyrannus) and Pacific salmon (mixed, but mostly from sockeye, Oncorhynchus nerka). The major branched-chain fatty acid in the salmon oil, 7-methyl-7-hexadecenoic acid, was also present to a moderate extent in menhaden oil. A novel vicinal dimethyl-branched fatty acid, 7,8-dimethyl-7-hexadecenoic was detected in all of the fish oils examined, but was most important in the salmon oil. Three monomethyl-branched fatty acids, 11-methyltetradecanoic acid, and 11- and 13-methylhexadecanoic, hitherto undescribed in fish lipids, were also detected in salmon, redfish and menhaden oils. PMID:2779367

Ratnayake, W M; Olsson, B; Ackman, R G

1989-07-01

337

Is acetylcarnitine a substrate for fatty acid synthesis in plants  

SciTech Connect

Long-chain fatty acid synthesis from [1-[sup 14]C]acetylcarnitine by chloroplasts isolated from spinach (Spinacia oleracea), pea (Pisum sativum), amaranthus (Amaranthus lividus), or maize (Zea mays) occurred at less than 2% of the rate of fatty acid synthesis from [1-[sup 14]C]acetate irrespective of the maturity of the leaves or whether the plastids were purified using sucrose or Percoll medium. [1-[sup 14]C]Acetylcarnitine was not significantly utilized by highly active chloroplasts rapidly prepared from pea and spinach using methods not involving density gradient centrifugation. [1-[sup 14]C]Acetylcarnitine was recovered quantitatively from chloroplast incubations following 10 min in the light. Unlabeled acetyl-L-carnitine (0.4 mM) did not compete with [1-[sup 14]C]acetate (0.2 mM) as a substrate for fatty acid synthesis by any of the more than 70 chloroplast preparations tested in this study. Carnitine acetyltransferase activity was not detected in any chloroplast preparation and was present in whole leaf homogenates at about 0.1% of the level of acetyl-coenzyme A synthetase activity. When supplied to detached pea shoots and detached spinach, amaranthus, and maize leaves via the transpiration stream, 1 to 4% of the [1-[sup 14]C]acetylcarnitine and 47 to 57% of the [1-[sup 14]C]acetate taken up was incorporated into lipids. Most (78--82%) of the [1-[sup 14]C]acetylcarnitine taken up was recovered intact. It is concluded that acetylcarnitine is not a major precursor for fatty acid synthesis in plants. 29 refs., 5 tabs.

Roughan, G. (Horticulture Research Inst., Auckland (New Zealand)); Post-Beittenmiller, D.; Ohlrogge, J. (Michigan State Univ., East Lansing (United States)); Browse, J. (Washington State Univ., Pullman (United States))

1993-04-01

338

Fatty acid biosynthesis and lipogenic enzyme activities in subcutaneous adipose tissue of feedlot steers fed supplementary palm oil or soybean oil.  

PubMed

We hypothesized that supplementing finishing diets with palm oil would promote adipocyte differentiation in subcutaneous adipose tissue of feedlot steers, and that soybean oil supplementation would depress adipocyte differentiation. Twenty-eight Angus steers were assigned randomly to 3 groups of 9 or 10 steers and fed a basal diet without additional fat (control), with 3% palm oil (rich in palmitic acid), or with 3% soybean oil (rich in polyunsaturated fatty acids), for 10 wk, top-dressed daily. Palm oil had no effect (P > 0.05) on ADG, food intake, or G:F, whereas soybean oil depressed ADG (P = 0.02), food intake (P = 0.04), and G:F (P = 0.05). Marbling scores tended (P = 0.09) to be greater in palm oil-fed steers (Modest(09)) than in soybean oil-fed steers (Small(55)). Subcutaneous adipocyte mean volume was greater in palm oil-fed steers (515.9 pL) than in soybean-supplemented cattle (395.6 pL; P = 0.01). Similarly, glucose and acetate incorporation into total lipids in vitro was greater in subcutaneous adipose tissue of palm oil-fed steers (119.9 and 242.8 nmol·3h(-1)·10(5) cells, respectively) than adipose tissue of soybean oil-fed steers in (48.9 and 95.8 nmol·3h(-1)·10(5) cells, respectively). Glucose-6-phosphate dehydrogenase and NADP-malate dehydrogenase activities were greater (P ? 0.05) in subcutaneous adipose tissue of palm oil-fed steers than in adipose tissue of control steers. Palm oil did not increase palmitic acid or decrease oleic acid in subcutaneous adipose tissue or LM, but decreased (P ? 0.05) myristoleic, palmitoleic, and cis-vaccenic acid in adipose tissue, indicating a depression in stearoyl-coenzyme A desaturase activity. Soybean oil increased the proportion of ?-linolenic acid in adipose tissue and muscle and increased linoleic acid and 18:1trans-10 in muscle. We conclude that palm oil supplementation promoted lipid synthesis in adipose tissue without depressing feed efficiency or increasing the palmitic acid content of beef. PMID:23463571

Choi, S H; Gang, G O; Sawyer, J E; Johnson, B J; Kim, K H; Choi, C W; Smith, S B

2013-05-01

339

21 CFR 862.1290 - Fatty acids test system.  

Code of Federal Regulations, 2013 CFR

...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Chemistry Test Systems § 862.1290 Fatty acids test system. (a)...

2013-04-01

340

21 CFR 862.1290 - Fatty acids test system.  

...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Chemistry Test Systems § 862.1290 Fatty acids test system. (a)...

2014-04-01

341

21 CFR 862.1290 - Fatty acids test system.  

Code of Federal Regulations, 2011 CFR

...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Chemistry Test Systems § 862.1290 Fatty acids test system. (a)...

2011-04-01

342

21 CFR 862.1290 - Fatty acids test system.  

Code of Federal Regulations, 2010 CFR

...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) MEDICAL DEVICES CLINICAL CHEMISTRY AND CLINICAL TOXICOLOGY DEVICES Clinical Chemistry Test Systems § 862.1290 Fatty acids test system. (a)...

2010-04-01

343

Density estimation for fatty acids and vegetable oils based on their fatty acid composition  

Microsoft Academic Search

The liquid density of fatty acids can be accurately estimated by the modified Rackett equation over a wide range of temperatures.\\u000a The modified Rackett equation requires the critical properties and an empirical parameter,Z\\u000a \\u000a RA\\u000a , for each acid as the basis for computing density as a function of temperature. The liquid density of vegetable oils can\\u000a be estimated by using

J. D. Halvorsen; L. D. Clements

1993-01-01

344

Omega3 Fatty Acids from Fish Oil Lower Anxiety, Improve Cognitive Functions and Reduce Spontaneous Locomotor Activity in a Non-Human Primate  

Microsoft Academic Search

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

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

2011-01-01

345

Inhibition of Insulin Sensitivity by Free Fatty Acids Requires Activation of Multiple Serine Kinases in 3T3-L1 Adipocytes  

Microsoft Academic Search

Insulin receptor substrate (IRS) has been sug- gested as a molecular target of free fatty acids (FFAs) for insulin resistance. However, the signal- ing pathways by which FFAs lead to the inhibition of IRS function remain to be established. In this study, we explored the FFA-signaling pathway that contributes to serine phosphorylation and degra- dation of IRS-1 in adipocytes and

ZHANGUO GAO; XIAOYING ZHANG; AAMIR ZUBERI; DANIEL HWANG; MICHAEL J. QUON; MICHAEL LEFEVRE; JIANPING YE

2004-01-01

346

Transcriptional regulation of fatty acid biosynthesis in mycobacteria.  

PubMed

The main purpose of our study is to understand how mycobacteria exert control over the biosynthesis of their membrane lipids and find out the key components of the regulatory network that control fatty acid biosynthesis at the transcriptional level. In this article we describe the identification and purification of FasR, a transcriptional regulator from Mycobacterium sp. that controls the expression of the fatty acid synthase (fas) and the 4-phosphopantetheinyl transferase (acpS) encoding genes, whose products are involved in the fatty acid and mycolic acid biosynthesis pathways. In vitro studies demonstrated that fas and acpS genes are part of the same transcriptional unit and that FasR specifically binds to three conserved operator sequences present in the fas-acpS promoter region (Pfas). The construction and further characterization of a fasR conditional mutant confirmed that FasR is a transcriptional activator of the fas-acpS operon and that this protein is essential for mycobacteria viability. Furthermore, the combined used of Pfas-lacZ fusions in different fasR backgrounds and electrophoretic mobility shift assays experiments, strongly suggested that long-chain acyl-CoAs are the effector molecules that modulate the affinity of FasR for its DNA binding sequences and therefore the expression of the essential fas-acpS operon. PMID:23721164

Mondino, S; Gago, G; Gramajo, H

2013-07-01

347

Transcriptional regulation of fatty acid biosynthesis in mycobacteria  

PubMed Central

SUMMARY The main purpose of our study is to understand how mycobacteria exert control over the biosynthesis of their membrane lipids and find out the key components of the regulatory network that control fatty acid biosynthesis at the transcriptional level. In this paper we describe the identification and purification of FasR, a transcriptional regulator from Mycobacterium sp. that controls the expression of the fatty acid synthase (fas) and the 4-phosphopantetheinyl transferase (acpS) encoding genes, whose products are involved in the fatty acid and mycolic acid biosynthesis pathways. In vitro studies demonstrated that fas and acpS genes are part of the same transcriptional unit and that FasR specifically binds to three conserved operator sequences present in the fas-acpS promoter region (Pfas). The construction and further characterization of a fasR conditional mutant confirmed that FasR is a transcriptional activator of the fas-acpS operon and that this protein is essential for mycobacteria viability. Furthermore, the combined used of Pfas-lacZ fusions in different fasR backgrounds and electrophoretic mobility shift assays experiments, strongly suggested that long-chain acyl-CoAs are the effector molecules that modulate the affinity of FasR for its DNA binding sequences and therefore the expression of the essential fas-acpS operon. PMID:23721164

Mondino, S.; Gago, G.; Gramajo, H.

2013-01-01

348

Improving the fatty acid profile of fairy shrimp, Streptocephalus dichotomus, using a lipid emulsion rich in highly unsaturated fatty acids.  

PubMed

Fatty acids are the largest component of lipids and have become a useful tool in the determination of live feeds to a variety of cultured species. Bioencapsulation is a technique which allows high-level incorporation of desired components (i.e., fatty acids, vitamins, antibiotics, etc.) in live feeds, which in turn can be supplemented to the consumer organisms. The procedure described in the present study serves as a platform of technology for enriching the Streptocephalus dichotomus. Uptake of two enrichment diets (ALGAMAC2000 and DHA-SELCO) by adult S. dichotomus was investigated. The fatty acid profile supports the hypothesis that the enrichment diet increases the level of essential fatty acids, such as linolic, linolenic, eicosapentenoic, and docosahexaenoic acids. The average content (percent of total fatty acids detected) of the enriched organism by different highly unsaturated fatty acid (HUFA) products were as follows: ALGAMAC2000 showed 14-22% saturated fatty acid (SFA), 17-18% monounsaturated fatty acid (MUFA), 28-41% polyunsaturated fatty acid (PUFA), 23-34% n-3, and 4.9-7.5% n-6, whereas DHA-SELCO showed about 20-23% SFA, 20-26% MUFA, 38% PUFA, 28-31% n-3, and 7.5-10% n-6. Our present investigation proves that both HUFA-rich diets appear to be an appropriate enrichment diet, and further provides an additional rationale for using fairy shrimp as a maturation diet for any cultivable freshwater organism. PMID:15537314

Velu, Chinavenmeni S; Munuswamy, Natesan

2004-11-17

349

Conformational Flexibility of Metazoan Fatty Acid Synthase Enables Catalysis  

PubMed Central

The metazoan cytosolic fatty acid synthase (FAS) contains all of the enzymes required for de novo fatty acid biosynthesis covalently linked around two reaction chambers. While the 3D architecture of FAS has been mostly defined, it is unclear how reaction intermediates can transfer between distant catalytic domains. Using single-particle electron microscopy we have identified a near continuum of conformations consistent with remarkable flexibility of FAS. The distribution of conformations was influenced by the presence of substrates and altered by different catalytic mutations suggesting a direct correlation between conformation and specific enzymatic activities. 3D reconstructions were interpreted by docking high-resolution structures of individual domains and illustrate that the substrate loading and condensation domains dramatically swing and swivel to access substrates within either reaction chamber. Concomitant rearrangement of the ?-carbon processing domains synchronizes acyl-chain reduction in one chamber with acyl-chain elongation in the other. PMID:19151726

Brignole, Edward J.; Smith, Stuart; Asturias, Francisco J.

2008-01-01

350

Process for enzymatic hydrolysis of fatty acid triglycerides with oat caryopses  

SciTech Connect

This patent describes the process for enzymatic hydrolysis of fatty acid triglycerides to obtain free fatty acids and glycerol. It comprises: increasing the water content of dehulled whole oat caryopses to a total water content of 17 to 44% the thus moistened caryopses having active oat lipase associated with the outer surfaces thereof; contacting the moistened whole caryopses with a liquid medium, continuing the contacting until at least 20% by volume of the triglyceride reactant has been hydrolyzed to free fatty acids and glycerol, most of the free fatty acids dissolving in the oil phase external to the caryopses and most of the glycerol being absorbed into the water within the caryopses; and separating the glycerol-containing caryopses from the fatty acid-containing oil phase.

Hammond, E.G.; Lee, I.

1992-02-18

351

TRPA1 Is a Polyunsaturated Fatty Acid Sensor in Mammals  

PubMed Central

Fatty acids can act as important signaling molecules regulating diverse physiological processes. Our understanding, however, of fatty acid signaling mechanisms and receptor targets remains incomplete. Here we show that Transient Receptor Potential Ankyrin 1 (TRPA1), a cation channel expressed in sensory neurons and gut tissues, functions as a sensor of polyunsaturated fatty acids (PUFAs) in vitro and in vivo. PUFAs, containing at least 18 carbon atoms and three unsaturated bonds, activate TRPA1 to excite primary sensory neurons and enteroendocrine cells. Moreover, behavioral aversion to PUFAs is absent in TRPA1-null mice. Further, sustained or repeated agonism with PUFAs leads to TRPA1 desensitization. PUFAs activate TRPA1 non-covalently and independently of known ligand binding domains located in the N-terminus and 5th transmembrane region. PUFA sensitivity is restricted to mammalian (rodent and human) TRPA1 channels, as the drosophila and zebrafish TRPA1 orthologs do not respond to DHA. We propose that PUFA-sensing by mammalian TRPA1 may regulate pain and gastrointestinal functions. PMID:22723860

Motter, Arianne L.; Ahern, Gerard P.

2012-01-01

352

The fat of the matter: how dietary Fatty acids can affect exercise performance.  

PubMed

Fatty-acid composition of fat stores affects exercise performance in a variety of vertebrates although few such studies focus on flying vertebrates such as migratory birds, which are exceptional exercisers. We first discuss the natural variation in quality of fat available in natural foods eaten by migratory birds and their behavioral preferences for specific fatty acids in these foods. We then outline three proposed hypotheses for how dietary fatty acids can affect exercise performance, and some of the evidence to date that pertains to these hypotheses with special emphasis on the exercise performance of migratory birds. In theory, selectively feeding on certain long-chain unsaturated fatty acids may be advantageous because (1) such fatty acids may be metabolized more quickly and may stimulate key facets of aerobic metabolism (fuel hypothesis); (2) such fatty acids may affect composition and key functions of lipid-rich cell membranes (membrane hypothesis); and (3) such fatty acids may directly act as signaling molecules (signal hypothesis). Testing these hypotheses requires cleverly designed experiments that can distinguish between them by demonstrating that certain fatty acids stimulate oxidative capacity, including gene expression and activity of key oxidative enzymes, and that this stimulation changes during exercise. PMID:25009307

Pierce, Barbara J; McWilliams, Scott R

2014-11-01

353

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

E-print Network

consisting of a control soybean meal diet and 2 test diets containing either 10y. or 20K canola oil (CO). Twelve Angus X Hereford steers were assigned to either a control high energy diet or a test diet consisting of 20y rapeseed at the expense of 20.... Significant increases in "oiliness" and decreases in fat firmness were observed when increasing levels of canola oil were fed to the swine. All sensory traits from the pork chops were not changed significantly as a result of treatment. No change in fatty...

St. John, Lori Ceanne

2012-06-07

354

Analysis of ?12-fatty acid desaturase function revealed that two distinct pathways are active for the synthesis of PUFAs in T. aureum ATCC 34304  

PubMed Central

Thraustochytrids are known to synthesize PUFAs such as docosahexaenoic acid (DHA). Accumulating evidence suggests the presence of two synthetic pathways of PUFAs in thraustochytrids: the polyketide synthase-like (PUFA synthase) and desaturase/elongase (standard) pathways. It remains unclear whether the latter pathway functions in thraustochytrids. In this study, we report that the standard pathway produces PUFA in Thraustochytrium aureum ATCC 34304. We isolated a gene encoding a putative ?12-fatty acid desaturase (Tau?12des) from T. aureum. Yeasts transformed with the tau?12des converted endogenous oleic acid (OA) into linoleic acid (LA). The disruption of the tau?12des in T. aureum by homologous recombination resulted in the accumulation of OA and a decrease in the levels of LA and its downstream PUFAs. However, the DHA content was increased slightly in tau?12des-disruption mutants, suggesting that DHA is primarily produced in T. aureum via the PUFA synthase pathway. The transformation of the tau?12des-disruption mutants with a tau?12des expression cassette restored the wild-type fatty acid profiles. These data clearly indicate that Tau?12des functions as ?12-fatty acid desaturase in the standard pathway of T. aureum and demonstrate that this thraustochytrid produces PUFAs via both the PUFA synthase and the standard pathways. PMID:22368282

Matsuda, Takanori; Sakaguchi, Keishi; Hamaguchi, Rie; Kobayashi, Takumi; Abe, Eriko; Hama, Yoichiro; Hayashi, Masahiro; Honda, Daiske; Okita, Yuji; Sugimoto, Shinichi; Okino, Nozomu; Ito, Makoto

2012-01-01

355

Understanding diet and modeling changes in the omega-3 and omega-6 Fatty Acid composition of u.s. Garrison foods for active duty personnel.  

PubMed

Research indicates that dietary omega-3 and omega-6 polyunsaturated fatty acids (PUFAs) are important in reducing the risk of mental illness. We used the DoD Survey of Health Related Behaviors among Active Duty Military Personnel (HRBS) to assess current military dietary patterns and meal locations. We used the Lands Equation to model PUFAs in a sample Garrison diet and the nutritional impact of substitution of foods higher in omega-3 PUFAs and lower in omega-6 PUFAs on tissue composition. The military diet was very poor quality compared to 2010 Healthy People Guidelines. A representative Garrison diet does not meet our estimated healthy n-3 HUFA intake at 3.5 g/d, corresponding with a tissue composition of 60% n-3 in HUFA (i.e., 40% n-6 in HUFA). Substitution of n-3 rich eggs, poultry, pork and other food commodities, combined with use on low linoleic acid oils, may contribute significantly to attaining healthier n-6/n-3 proportions in the tissue. PMID:25373102

Marriott, Bernadette P; Yu, Karina; Majchrzak-Hong, Sharon; Johnson, Jeremiah; Hibbeln, Joseph R

2014-11-01

356

A condensing enzyme from the seeds of Lesquerella fendleri that specifically elongates hydroxy fatty acids.  

PubMed

Lesquerella fendleri seed oil contains up to 60% hydroxy fatty acids, nearly all of which is the 20-carbon hydroxy fatty acid lesquerolic acid (D-14-hydroxyeicos-cis-11-enoic acid). Previous work suggested that lesquerolic acid in L. fendleri was formed by the elongation of the 18-carbon hydroxy fatty acid, ricinoleic acid. To identify a gene encoding the enzyme involved in hydroxy fatty acid elongation, an L. fendleri genomic DNA library was screened using the coding region of the Arabidopsis Fatty Acid Elongation1 gene as a probe. A gene, LfKCS3, with a high sequence similarity to known very long-chain fatty acid condensing enzymes, was isolated. LfKCS3 has a 2,062-bp open reading frame interrupted by two introns, which encodes a polypeptide of 496 amino acids. LfKCS3 transcripts accumulated only in the embryos of L. fendleri and first appeared in the early stages of development. Fusion of the LfKCS3 promoter to the uidA reporter gene and expression in transgenic Arabidopsis resulted in a high level of beta-glucuronidase activity exclusively in developing embryos. Seeds of Arabidopsis plants transformed with LfKCS3 showed no change in their very long-chain fatty acid content. However, when these Arabidopsis plants were crossed with the transgenic plants expressing the castor oleate 12-hydroxylase, significant amounts of 20-carbon hydroxy fatty acids accumulated in the seed, indicating that the LfKCS3 condensing enzyme specifically catalyzes elongation of 18-carbon hydroxy fatty acids. PMID:11743108

Moon, H; Smith, M A; Kunst, L

2001-12-01

357

A Condensing Enzyme from the Seeds of Lesquerella fendleri That Specifically Elongates Hydroxy Fatty Acids1  

PubMed Central

Lesquerella fendleri seed oil contains up to 60% hydroxy fatty acids, nearly all of which is the 20-carbon hydroxy fatty acid lesquerolic acid (d-14-hydroxyeicos-cis-11-enoic acid). Previous work suggested that lesquerolic acid in L. fendleri was formed by the elongation of the 18-carbon hydroxy fatty acid, ricinoleic acid. To identify a gene encoding the enzyme involved in hydroxy fatty acid elongation, an L. fendleri genomic DNA library was screened using the coding region of the Arabidopsis Fatty Acid Elongation1 gene as a probe. A gene, LfKCS3, with a high sequence similarity to known very long-chain fatty acid condensing enzymes, was isolated. LfKCS3 has a 2,062-bp open reading frame interrupted by two introns, which encodes a polypeptide of 496 amino acids. LfKCS3 transcripts accumulated only in the embryos of L. fendleri and first appeared in the early stages of development. Fusion of the LfKCS3 promoter to the uidA reporter gene and expression in transgenic Arabidopsis resulted in a high level of ?-glucuronidase activity exclusively in developing embryos. Seeds of Arabidopsis plants transformed with LfKCS3 showed no change in their very long-chain fatty acid content. However, when these Arabidopsis plants were crossed with the transgenic plants expressing the castor oleate 12-hydroxylase, significant amounts of 20-carbon hydroxy fatty acids accumulated in the seed, indicating that the LfKCS3 condensing enzyme specifically catalyzes elongation of 18-carbon hydroxy fatty acids. PMID:11743108

Moon, Hangsik; Smith, Mark A.; Kunst, Ljerka

2001-01-01

358

Stimulation of tumor-associated fatty acid synthase expression by growth factor activation of the sterol regulatory element-binding protein pathway.  

PubMed

Increased expression of fatty acid synthase (FAS) is observed in a clinically aggressive subset of various common cancers and interference with FAS offers promising opportunities for selective chemotherapeutic intervention. The mechanisms by which FAS expression is (up)-regulated in these tumors remain, however, largely unknown. Recently we demonstrated that in LNCaP prostate cancer cells FAS expression is markedly elevated by androgens via an indirect pathway involving sterol regulatory element-binding proteins (SREBPs). Here, we also show that growth factors such as EGF are able to stimulate FAS mRNA, protein and activity. Several observations also indicate that the effects of EGF on FAS expression are ultimately mediated by SREBPs. EGF stimulates SREBP-1c mRNA expression and induces an increase in mature nuclear SREBP-1. Moreover, in transient transfection studies EGF stimulates the transcriptional activity of a 178 bp FAS promoter fragment harboring a complex SREBP-binding site. Deletion or mutation of this binding site abolishes these effects and ectopic expression of dominant negative SREBP-1 inhibits FAS expression and induction in intact LNCaP cells. Given the frequent dysregulation of growth factor signaling in cancer and the key role of SREBP-1 in lipid homeostasis, growth factor-induced activation of the SREBP pathway is proposed as one of the mechanisms responsible for up-regulation of lipogenic gene expression in a subset of cancer cells. PMID:11064454

Swinnen, J V; Heemers, H; Deboel, L; Foufelle, F; Heyns, W; Verhoeven, G

2000-10-26

359

Measuring Oral Fatty Acid Thresholds, Fat Perception, Fatty Food Liking, and Papillae Density in Humans  

PubMed Central

Emerging evidence from a number of laboratories indicates that humans have the ability to identify fatty acids in the oral cavity, presumably via fatty acid receptors housed on taste cells. Previous research has shown that an individual's oral sensitivity to fatty acid, specifically oleic acid (C18:1) is associated with body mass index (BMI), dietary fat consumption, and the ability to identify fat in foods. We have developed a reliable and reproducible method to assess oral chemoreception of fatty acids, using a milk and C18:1 emulsion, together with an ascending forced choice triangle procedure. In parallel, a food matrix has been developed to assess an individual's ability to perceive fat, in addition to a simple method to assess fatty food liking. As an added measure tongue photography is used to assess papillae density, with higher density often being associated with increased taste sensitivity. PMID:24961177

Haryono, Rivkeh Y.; Sprajcer, Madeline A.; Keast, Russell S. J.

2014-01-01

360

Unexpected functional diversity in the fatty acid desaturases of the flour beetle Tribolium castaneum and identification of key residues determining activity.  

PubMed

Desaturases catalyse modifications to fatty acids which are essential to homeostasis and for pheromone and defensive chemical production. All desaturases of the flour beetle Tribolium castaneum were investigated via query of the sequenced genome which yielded 15 putative acyl-Coenzyme A genes. Eleven desaturase mRNA were obtained in full length and functionally expressed in yeast. Phylogenetic analysis separated the desaturases into 4 distinct clades; one clade contained conserved beetle ?9 desaturases, second clade was Tribolium-specific having diverse activities including ?5, ?9 and ?12 desaturation and the other 2 clades had mixed insect representatives. Three members of this clade contained unusual inserted sequences of ?20 residues in the C-terminal region and were related to desaturases that all contained similar inserts. Deletion of the entirety of the insert in the flour beetle ?12 desaturase abolished its activity but this was partially restored by the reintroduction of two histidine residues, suggesting the histidine(s) are required for activity but the full length insert is not. Five new desaturase activities were discovered: ?9 desaturation of C12:0-C16:0 substrates; two unprecedented ?5 enzymes acting on C18:0 and C16:0; ?9 activity exclusively on C16:0 and a further stearate ?9 desaturase. qPCR analysis ruled out a role in sex pheromone synthesis for the ?5 and ?9/C16:0 desaturases. The flour beetle genome has underpinned an examination of all transcribed desaturases in the organism and revealed a diversity of novel and unusual activities, an improved understanding of the evolutionary relationships among insect desaturases and sequence determinants of activity. PMID:24880119

Haritos, Victoria S; Horne, Irene; Damcevski, Katherine; Glover, Karen; Gibb, Nerida

2014-08-01

361

Turkish freshwater and marine macrophyte extracts show in vitro antiprotozoal activity and inhibit FabI, a key enzyme of Plasmodium falciparum fatty acid biosynthesis.  

PubMed

The ethanolic extracts of a number of Turkish freshwater macrophytes (Potamogeton perfoliatus, Ranunculus tricophyllus and Cladophora glomerata) and marine macroalgae (Dictyota dichotoma, Halopteris scoparia, Posidonia oceanica, Scinaia furcellata, Sargassum natans and Ulva lactuca) were assayed for their in vitro antiprotozoal activity. Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani and Plasmodium falciparum were used as test organisms. The cytotoxicity of the extracts was also assessed against primary rat skeletal myoblasts (L6 cells). Whereas none of the extracts were active against T. cruzi, all crude extracts displayed appreciable trypanocidal activity against T. brucei rhodesiense, with S. natans being the most active one (IC(50) 7.4microg/ml). Except for the marine alga H. scoparia, all extracts also possessed leishmanicidal potential. The best antileishmanial activity was exerted by U. lactuca and P. oceanica (IC(50)'s 5.9 and 8.0microg/ml, respectively). Five extracts that demonstrated inhibitory activity towards P. falciparum (IC(50)'s 18.1-48.8microg/ml) were simultaneously assayed against FabI, a crucial enzyme of the fatty acid system of P. falciparum, to find out whether FabI was their target. The extracts of C. glomerata and U. lactuca efficiently inhibited the FabI enzyme with IC(50) values of 1.0 and 4.0microg/ml, respectively. None of the extracts were cytotoxic towards mammalian L6 cells. This work reports for the first time antiprotozoal activity of some Turkish marine and freshwater algae, as well as a target-based antiplasmodial screening for the identification of P. falciparum FabI inhibitors from aquatic and marine macrophytes. PMID:16697632

Orhan, I; Sener, B; Atici, T; Brun, R; Perozzo, R; Tasdemir, D

2006-06-01

362

Regulatory role of E-NTPase\\/NTPDase in fat\\/CD36-mediated fatty acid uptake  

Microsoft Academic Search

Fatty acid translocase (FAT)\\/CD36-mediated long-chain fatty acid uptake in human umbilical vessel endothelial cells is associated with as yet uncharacterized translocase activity. The molecular mechanism of its function is not yet understood. Numerous attempts to purify rat cardiac sarcolemmal E-NTPase (an integral membrane protein also referred to as ecto-Ca2+\\/Mg2+ATPase) have revealed a complete amino acid sequence identity for FAT\\/CD36 protein.

Subburaj Kannan

2003-01-01

363

Two fatty acid elongases possessing C18-?6/C18-?9/C20-?5 or C16-?9 elongase activity in Thraustochytrium sp. ATCC 26185.  

PubMed

Thraustochytrids, unicellular eukaryotic marine protists, accumulate polyunsaturated fatty acids. Here, we report the molecular cloning and functional characterization of two fatty acid elongase genes (designated tselo1 and tselo2), which could be involved in the desaturase/elongase (standard) pathway in Thraustochytrium sp. ATCC 26185. TsELO1, the product of tselo1 and classified into a ?6 elongase group by phylogenetic analysis, showed strong C18-?6 elongase activity and relatively weak C18-?9 and C20-?5 activities when expressed in the budding yeast Saccharomyces cerevisiae. TsELO2, classified into a ?9 elongase subgroup, showed only C16-?9 activity. When expressed in Aurantiochytrium limacinum mh0186 using a thraustochytrid-derived promoter and a terminator, TsELO1 exhibited almost the same specificity as expressed in the yeast but TsELO2 showed weak C18-?9 activity, in addition to its main C16-?9 activity. These results suggest that TsELO1 functions not only as a C18-?6 and a C20-?5 elongase in the main route but also as a C18-?9 elongase in the alternative route of standard pathway, while TsELO2 functions mainly as a C16-?9 elongase generating vaccenic acid (C18:1n-7) in thraustochytrids. This is the first report describing a fatty acid elongase harboring C16-?9 activity in thraustochytrids. PMID:23547001

Ohara, Junichiro; Sakaguchi, Keishi; Okita, Yuji; Okino, Nozomu; Ito, Makoto

2013-08-01

364

Overexpression of Fatty-Acid-?-Oxidation-Related Genes Extends the Lifespan of Drosophila melanogaster  

PubMed Central

A better understanding of the aging process is necessary to ensure that the healthcare needs of an aging population are met. With the trend toward increased human life expectancies, identification of candidate genes affecting the regulation of lifespan and its relationship to environmental factors is essential. Through misexpression screening of EP mutant lines, we previously isolated several genes extending lifespan when ubiquitously overexpressed, including the two genes encoding the fatty-acid-binding protein and dodecenoyl-CoA delta-isomerase involved in fatty-acid ?-oxidation, which is the main energy resource pathway in eukaryotic cells. In this study, we analyzed flies overexpressing the two main components of fatty-acid ?-oxidation, and found that overexpression of fatty-acid-?-oxidation-related genes extended the Drosophila lifespan. Furthermore, we found that the ability of dietary restriction to extend lifespan was reduced by the overexpression of fatty-acid-?-oxidation-related genes. Moreover, the overexpression of fatty-acid-?-oxidation-related genes enhanced stress tolerance to oxidative and starvation stresses and activated the dFOXO signal, indicating translocation to the nucleus and transcriptional activation of the dFOXO target genes. Overall, the results of this study suggest that overexpression of fatty-acid-?-oxidation-related genes extends lifespan in a dietary-restriction-related manner, and that the mechanism of this process may be related to FOXO activation. PMID:22997544

Lee, Shin-Hae; Lee, Su-Kyung; Paik, Donggi; Min, Kyung-Jin

2012-01-01

365

?-Sulfonated fatty acids and esters: Manufacturing process, properties, and applications  

Microsoft Academic Search

?-Sulfonated fatty acid esters, because of their wide-range of application and biological properties, represent an interesting\\u000a class of surfactants. A technical method for the preparation of ?-sulfonated fatty acid esters is described. By using special\\u000a reaction conditions it is possible to ?-sulfonate saturated fatty esters directly without the use of solvents. The use of\\u000a gaseous SO3 gives the product in

W. Stein; H. Baumann

1975-01-01

366

Fatty Acids as Therapeutic Auxiliaries for Oral and Parenteral Formulations  

PubMed Central

Many drugs have decreased therapeutic activity due to issues with absorption, distribution, metabolism and excretion. The co-formulation or covalent attachment of drugs with fatty acids has demonstrated some capacity to overcome these issues by improving intestinal permeability, slowing clearance and binding serum proteins for selective tissue uptake and metabolism. For orally administered drugs, albeit at low level of availability, the presence of fatty acids and triglycerides in the intestinal lumen may promote intestinal uptake of small hydrophilic molecules. Small lipophilic drugs or acylated hydrophilic drugs also show increased lymphatic uptake and enhanced passive diffusional uptake. Fatty acid conjugation of small and large proteins or peptides have exhibited protracted plasma half-lives, site-specific delivery and sustained release upon parenteral administration. These improvements are most likely due to associations with lipid-binding serum proteins, namely albumin, LDL and HDL. These molecular interactions, although not fully characterized, could provide the ability of using the endogenous carrier systems for improving therapeutic outcomes. PMID:22921839

Hackett, Michael J.; Zaro, Jennica L.; Shen, Wei-Chiang; Guley, Patrick C.; Cho, Moo J.

2012-01-01

367

Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects.  

PubMed

Our objective was to determine whether bezafibrate, a hypotriglyceridemic drug and peroxisome proliferator-activated receptor (PPAR)-alpha agonist, is ketogenic and increases fatty acid oxidation in humans. We measured fatty acid metabolism and ketone levels in 13 mildly hypertriglycemic adults (67 +/- 11 years old) during 2 metabolic study days lasting 6 h, 1 day before and 1 day after bezafibrate (400 mg of bezafibrate per day for 12 weeks). beta-Hydroxybutyrate, triglycerides, free fatty acids, fatty acid profiles, insulin, and glucose were measured in plasma, and fatty acid beta-oxidation was measured in breath after an oral 50-mg dose of the fatty acid tracer [U-(13)C]linoleic acid. As expected, 12 weeks on bezafibrate decreased plasma triglycerides by 35%. Bezafibrate tended to raise postprandial beta-hydroxybutyrate, an effect that was significant after normalization to the fasting baseline values (p = 0.03). beta-Oxidation of [U-(13)C]linoleic acid increased by 30% (p = 0.03) after treatment. On the metabolic study day after bezafibrate treatment, postprandial insulin decreased by 26% (p = 0.01), and glucose concentrations were lower 2 to 5 h postprandially. Thus, in hypertriglyceridemic individuals, bezafibrate is mildly ketogenic and significantly changes fatty acid metabolism, effects that may be linked to PPARalpha stimulation and to moderately improved glucose metabolism. PMID:20404010

Tremblay-Mercier, Jennifer; Tessier, Daniel; Plourde, Mélanie; Fortier, Mélanie; Lorrain, Dominique; Cunnane, Stephen C

2010-07-01

368

Effect of Calcium Soap of Fatty Acids Supplementation on Serum Biochemical Parameters and Ovarian Activity during Out-of-the-Breeding Season in Crossbred Ewes  

PubMed Central

This experiment aimed to evaluate the effect of calcium soap of fatty acid (CSFA) supplementation on serum biochemical and hormones and ovarian activity during out-of-the-breeding season in ewes. Twelve crossbred ewes, 2-3 years of age and weighting 45–55?kg, were allocated into two equal groups. The first group was control and the other was treated with 50?g/head of CSFA. All ewes were fed basal diet and treated with 60?mg of medroxy progesterone acetate intravaginal sponge for 12 day. At the third day of sponge removal, the CSFA-treated group was given 50?g/head of CSFA daily for two estrous cycles. During the estrus phase, ovarian activity was detected using ultrasonography in both groups. All ewes were then subjected to natural breeding and conception rate. Blood samples were collected from all ewes during treatment period. Results revealed significant (P < 0.05) increases in serum cholesterol, triglycerides, low-density lipoprotein cholesterol, glucose, and progesterone levels with decrease in calcium and phosphorous levels in treated group. In treated group, normal-size ovaries and more than one follicle on the ovaries were detected and pregnancy rate increased. In conclusion, CSFA supplementation was effective to maintain the reproductive performance when ewes were out of the breeding season. PMID:22629155

El-Nour, Hayat H. M.; Nasr, Soad M.; Hassan, Walid R.

2012-01-01

369

Hepatic metabolism of free fatty acids in normal and diabetic dogs  

PubMed Central

Fasted dogs prepared with catheters in the femoral artery, portal vein, and hepatic vein and infused intravenously with palmitate-1-14C were used to estimate uptake of free fatty acids in liver and their conversion to major metabolic products secreted into hepatic venous blood. Animals were studied under ordinary conditions and when fat mobilization was increased abruptly by infusing norepinephrine or for a prolonged period by withdrawing insulin from depancreatized dogs. 80% of hepatic blood flow was assumed to be derived from the portal vein. Hepatic uptake was proportional to net outflow transport of plasma free fatty acids in the three groups and, in each, hepatic extraction fraction was about 25%. Since specific activity of free fatty acids entering and leaving the liver was equal and their composition was closely similar in the three sites sampled, it was concluded that palmitate is a representative tracer for free fatty acids entering the liver and that the liver does not release free fatty acids into the blood. In norepinephrine-infused dogs, the fraction of free fatty acids secreted in triglycerides (13%) was similar to that of control animals, so that transport of triglycerides was increased. In diabetic dogs no increased transport could be demonstrated since an average of only 2% of free fatty acids was converted to plasma triglyceride fatty acids; the hyperlipemia uniformly observed therefore appeared to result from defective removal of triglycerides from the blood. A similar fraction of free fatty acids was converted to ketones in normal and norepinephrine-infused dogs. This fraction was somewhat higher in diabetic animals and, in addition, a substantial quantity of ketones was derived from unlabeled precursors. Fractional conversion of free fatty acids to CO2 was similar in normal and norepinephrine-infused dogs, but reduced in the diabetics. PMID:5415680

Basso, Laurence V.; Havel, Richard J.

1970-01-01

370

Fatty acid trophic markers in the pelagic marine environment  

Microsoft Academic Search

Fatty acids have been used as qualitative markers to trace or confirm predator prey relationships in the marine environment for more than thirty years. More recently, they have also been used to identify key processes impacting the dynamics of some of the world's major ecosystems. The fatty acid trophic marker (FA TM) concept is based on the observation that marine

Johanne Dalsgaard; Michael St. John; Gerhard Kattner; Dörthe Müller-Navarra; Wilhelm Hagen

2003-01-01

371

Free Fatty Acids and Sterols in Swine Manure  

Microsoft Academic Search

Free fatty acids and sterols were assessed in fresh manure and anaerobic lagoon sludge from swine production facilities in North Carolina. Eight free fatty acids and five sterols were identified and quantified in both manure and sludge samples. Compound identification was performed by gas chromatography\\/mass spectroscopy (GC-MS), and compound quantities were determined by gas chromatography after solid phase extraction with

JOHN H. LOUGHRIN; ARIEL A. SZOGI

2006-01-01

372

Fatty acids in cell signalling: Modulation by lipid binding proteins  

Microsoft Academic Search

Long-chain fatty acids and several of their metabolites have now been shown to be involved as primary or secondary messengers in specific cell signalling pathways. In view of their extremely low aqueous solubility, the extracellular as well as intracellular transport of these compounds is assumed to be facilitated by specific lipid binding proteins, such as cytoplasmic fatty acid-binding protein (FABP).

J. F. C. Glatz; T. Börchers; F. Spener; Ger J. van der Vusse

1995-01-01

373

Solvent-free wood esterification with fatty acid chlorides  

Microsoft Academic Search

A method for wood esterification using fatty acid chlorides in the absence of organic solvents is proposed. A nitrogen stream was used to carry-off the hydrogen chloride formed during synthesis and to displace the equilibrium of the reaction. The experimental conditions being optimal (nitrogen flow rate, temperature and reaction time, quantity of fatty acid chloride), there was an increase in

S. Thiebaud; M. E. Borredon

1995-01-01

374

Original article Influence of milk fatty acid composition  

E-print Network

Original article Influence of milk fatty acid composition and process parameters on the quality the fatty acid composition of milk fat in dairy products to improve the long-term health of consumers two process parameters (homogenization pressure and ageing temperature) on the quality of ice cream

Paris-Sud XI, Université de

375

Fatty acid composition of the edible sea cucumber Athyonidium chilensis  

Microsoft Academic Search

The edible sea cucumber Athyonidium chilensis is a fishery resource of high commercial value in Chile, but no information on its lipid and fatty acid composition has been previously reported. Phospholipids were the major lipid contents of the ethanolic extracts of tubules, internal organs and body wall of A. chilensis. Saturated fatty acids predominated in tubule phospholipids (40.69%), while in

Valeria P. Careaga; Claudia Muniain; Martas S. Maier

2012-01-01

376

Essential fatty acids and sleep: mini-review and hypothesis  

Microsoft Academic Search

The neurochemical basis of sleep mechanisms (onset and maintenance) is still controversial although the phenomenon itself is known to be mediated by more than a single molecule. The list of suggested endogenous sleep substances is rather long, and there is no single ‘sleep center’ identified in the brain.The role of fatty acids, and essential fatty acids in particular, has been

S. Yehuda; S. Rabinovitz; D. I. Mostofsk

1998-01-01

377

Electron Impact Mass Spectroscopic Studies on Mouse Retinal Fatty Acids  

Microsoft Academic Search

Aim: The primary objective of these investigations was to determine the fatty acid composition of the mouse retina as affected by diabetes. Additionally, in order to ascertain if there is any accumulation of lipids in the diabetic retina as occurs in many diabetic tissues, its total fatty acid content was also determined. Methods: Lipids in the retina of normal and

K. R. Hegde; S. D. Varma

2009-01-01

378

21 CFR 172.863 - Salts of fatty acids.  

21 Food and Drugs 3 2014-04-01 2014-04-01 false Salts of fatty acids. 172.863 Section 172.863 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT...172.863 Salts of fatty acids. The food additive...

2014-04-01

379

Fatty acid synthase and the lipogenic phenotype in cancer pathogenesis  

Microsoft Academic Search

There is a renewed interest in the ultimate role of fatty acid synthase (FASN) — a key lipogenic enzyme catalysing the terminal steps in the de novo biogenesis of fatty acids — in cancer pathogenesis. Tumour-associated FASN, by conferring growth and survival advantages rather than functioning as an anabolic energy-storage pathway, appears to necessarily accompany the natural history of most

Javier A. Menendez; Ruth Lupu

2007-01-01

380

Habitat related variations in fatty acids of catadromous Galaxias maculatus  

Microsoft Academic Search

The fatty acid profile of the galaxiid fish Galaxias maculatus (Salmoniformes) collected from an estuarine habitat (a river mouth), a freshwater creek and two land-locked freshwater lakes in Victoria, Australia, were investigated with a view to evaluating habitat influences on the fatty acid profile. Fish from the freshwater creek were unpigmented, fresh-run juveniles (referred to as whitebait), the others adult

Sena S. De Silva; Rasanthi M. Gunasekera; Chris M. Austin; Graeme Allinson

1998-01-01