Sulfur-substituted and alpha-methylated fatty acids as peroxisome proliferator-activated receptor activators.

Abstract:

:FA with varying chain lengths and an alpha-methyl group and/or a sulfur in the beta-position were tested as peroxisome proliferator-activated receptor (PPAR)alpha, -delta(beta), and -gamma ligands by transient transfection in COS-1 cells using chimeric receptor expression plasmids, containing cDNAs encoding the ligand-binding domain of PPARalpha, -delta, and -gamma. For PPARalpha, an increasing activation was found with increasing chain length of the sulfur-substituted FA up to C14-S acetic acid (tetradecylthioacetic acid = TTA). The derivatives were poor, and nonsignificant, activators of PPARdelta. For PPARgamma, activation increased with increasing chain length up to C16-S acetic acid. A methyl group was introduced in the alpha-position of palmitic acid, TTA, EPA, DHA, cis9,trans11 CLA, and trans10,cis12 CLA. An increased activation of PPARalpha was obtained for the alpha-methyl derivatives compared with the unmethylated FA. This increase also resulted in increased expression of the two PPARalpha target genes acyl-CoA oxidase and liver FA-binding protein for alpha-methyl TTA, alpha-methyl EPA, and alpha-methyl DHA. Decreased or altered metabolism of these derivatives in the cells cannot be excluded. In conclusion, saturated FA with sulfur in the beta-position and increasing carbon chain length from C9-S acetic acid to C14-S acetic acid have increasing effects as activators of PPARalpha and -gamma in transfection assays. Furthermore, alpha-methyl FA derivatives of a saturated natural FA (palmitic acid), a sulfur-substituted FA (TTA), and PUFA (EPA, DHA, c9,t11 CLA, and t10,c12 CLA) are stronger PPARalpha activators than the unmethylated compounds.

journal_name

Lipids

journal_title

Lipids

authors

Larsen LN,Granlund L,Holmeide AK,Skattebøl L,Nebb HI,Bremer J

doi

10.1007/s11745-005-1359-3

subject

Has Abstract

pub_date

2005-01-01 00:00:00

pages

49-57

issue

1

eissn

0024-4201

issn

1558-9307

journal_volume

40

pub_type

杂志文章

相关文献

LIPIDS文献大全
  • Maldi-tof fingerprinting of seminal plasma lipids in the study of human male infertility.

    abstract::This study proposed lipid fingerprinting of human seminal plasma by mass spectrometry as an analytical method to differentiate biological conditions. For this purpose, we chose infertile men as a model to study specific conditions, namely: high and low seminal plasma lipid peroxidation levels (sub-study 1.1), high and...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-014-3922-7

    authors: Camargo M,Intasqui P,de Lima CB,Montani DA,Nichi M,Pilau EJ,Gozzo FC,Lo Turco EG,Bertolla RP

    更新日期:2014-09-01 00:00:00

  • Dietary cod liver oil decreases arachidonic acid in rat gastric mucosa and increases stress-induced gastric erosions.

    abstract::The purpose of this study was to examine the influence of long-term feeding of dietary fat rich in either n-3 or n-6 fatty acids on the availability of arachidonic acid (20:4n-6) in major phospholipids of gastric mucosa in rats. Three groups of male Wistar rats were fed either a standard diet, a cod liver oil-enriched...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-000-0562-6

    authors: Olafsson SO,Hallgrimsson J,Gudbjarnason S

    更新日期:2000-06-01 00:00:00

  • Absorption of synthetic, stereochemically defined acylglycerols in the rat.

    abstract::The stereochemistry of fat digestion and absorption was investigated in rats with thoracic duct fistulas, after feeding synthetic triacylglycerol or alkyldiacylglycerol. After feeding 1,2-dilauroyl-3-oleoyl-sn-glycerol, dilauroyloleoylglycerol and lauroyldioleoylglycerol were the most abundant chyle triacylglycerols. ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02533725

    authors: Akesson B,Gronowitz S,Herslof B,Ohlson R

    更新日期:1978-05-01 00:00:00

  • Determination of individual long-chain fatty acyl-CoA esters in heart and skeletal muscle.

    abstract::A method has been developed for determination of individual long-chain fatty acyl-CoA esters from heart and skeletal muscle using high performance liquid chromatography (HPLC). The esters were extracted from freeze-clamped tissue of pig and rat hearts and rat skeletal muscle for analysis on a radially compressed C18 5...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535525

    authors: Molaparast-Saless F,Shrago E,Spennetta TL,Donatello S,Kneeland LM,Nellis SH,Liedtke AJ

    更新日期:1988-05-01 00:00:00

  • Application of Silver Ion High-Performance Liquid Chromatography for Quantitative Analysis of Selected n-3 and n-6 PUFA in Oil Supplements.

    abstract::The aim of this study was to develop a simple method for simultaneous determination of selected cis/cis PUFA-LNA (18:2), ALA (18:3), GLA (18:3), EPA (20:5), and DHA (22:6) by silver ion high-performance liquid chromatography coupled to a diode array detector (Ag-HPLC-DAD). The separation was performed on three Luna SC...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-016-4133-1

    authors: Czajkowska-Mysłek A,Siekierko U,Gajewska M

    更新日期:2016-04-01 00:00:00

  • A review of tobacco BY-2 cells as an excellent system to study the synthesis and function of sterols and other isoprenoids.

    abstract::In plants, two pathways are utilized for the synthesis of isopentenyl diphosphate (IPP), the universal precursor for isoprenoid biosynthesis. In this paper we review findings and observations made primarily with tobacco BY-2 cells (TBY-2), which have proven to be an excellent system in which to study the two biosynthe...

    journal_title:Lipids

    pub_type: 杂志文章,评审

    doi:10.1007/s11745-004-1289-0

    authors: Hemmerlin A,Gerber E,Feldtrauer JF,Wentzinger L,Hartmann MA,Tritsch D,Hoeffler JF,Rohmer M,Bach TJ

    更新日期:2004-08-01 00:00:00

  • Antagonism of platelet-activating factor in isolated rat colon: possible mechanism.

    abstract::The contractions of three different regions of rat colon in response to platelet-activating factor (PAF) were compared. The ascending colon was found to be the most responsive. The slow contraction of the ascending colon induced by PAF was dependent on external Ca2+. CV-3988, a structural analog of PAF, slowly induced...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02536563

    authors: Tokumura A,Yube N,Terao M,Tsukatani H

    更新日期:1991-12-01 00:00:00

  • An improved method for analysis of glucosylceramide species having cis-8 and trans-8 isomers of sphingoid bases by LC-MS/MS.

    abstract::High-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) approaches have enabled high selectivity and sensitivity for the identification and quantification of glucosylceramide molecular species. Here we demonstrate that HPLC-ESI-MS/MS is an efficient method for character...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-012-3725-7

    authors: Imai H,Hattori H,Watanabe M

    更新日期:2012-12-01 00:00:00

  • Taurine supplementation of plant derived protein and n-3 fatty acids are critical for optimal growth and development of cobia, Rachycentron canadum.

    abstract::We examined growth performance and the lipid content in juvenile cobia, Rachycentron canadum, fed a taurine supplemented (1.5 %), plant protein based diet with two fish oil replacements. The first fish oil replacement was a thraustochytrid meal (TM + SOY) plus soybean oil (~9 % CL) and the second was a canola oil supp...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-013-3814-2

    authors: Watson AM,Barrows FT,Place AR

    更新日期:2013-09-01 00:00:00

  • Lipid composition and de novo lipid biosynthesis of human palmar fat in Dupuytren's disease.

    abstract::Seventy-two surgically obtained Dupuytren's disease palmar-fat (DDPF) specimens and 18 location-matched specimens from patients not suffering from this disease (controls) were studied for their total lipid composition and de novo lipogenic activity. Incubation of "DDPF" with 1-[14C]acetate in oxygen produced [14C]palm...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02537234

    authors: Rabinowitz JL,Ostermann L Jr,Bora FW,Staeffen J

    更新日期:1983-05-01 00:00:00

  • The effect of n-3 fatty acids on coronary atherosclerosis: results from SCIMO, an angiographic study, background and implications.

    abstract::According to the model of "response to injury," the arterial endothelium is occasionally injured in hyperlipidemia, hypertension, diabetes mellitus and in other states known as risk factors. The ensuing inflammatory response is modulated by cytokines and growth factors, among them platelet-derived growth factor (PDGF)...

    journal_title:Lipids

    pub_type: 临床试验,杂志文章,随机对照试验

    doi:10.1007/s11745-001-0689-5

    authors: von Schacky C,Baumann K,Angerer P

    更新日期:2001-01-01 00:00:00

  • Fatty acids bound to Fasciola hepatica 12 kDa fatty acid-binding protein, a candidate vaccine, differ from fatty acids in extracts of adult flukes.

    abstract::The FA composition of Fasciola hepatica 12 kDA purified native FA-binding protein (nFh12), a candidate vaccine against fascioliasis, is described. The FA chain lengths ranged between 12 and 24 carbons. The principal FA were 16:0, 18:1n-9, 18:0, 20:4n-6, and 20:1n-9. The acids 16:0, 18:1n-9, and 18:0 comprised over hal...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-003-1125-6

    authors: Carballeira NM,Cruz H,Hillyer GV

    更新日期:2003-07-01 00:00:00

  • The Expression of Lipoprotein Receptors Is Increased in the Infarcted Area After Myocardial Infarction Induced in Rats With Cardiac Dysfunction.

    abstract::Left ventricular (LV) remodeling after myocardial infarction constitutes the structural basis for ventricular dysfunction and heart failure. The characterization underlying the expression of lipoprotein receptors in cardiac dysfunction is scarcely explored. The aim of this study was to analyze the status of lipoprotei...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1002/lipd.12014

    authors: de Lima AD,Guido MC,Tavares ER,Carvalho PO,Marques AF,de Melo MDT,Salemi VMC,Kalil-Filho R,Maranhão RC

    更新日期:2018-02-01 00:00:00

  • The effects of dietary protein on the fatty acid composition and delta 6 desaturase activity of rat hepatic microsomes.

    abstract::Recently, significant differences between rats fed a casein diet and rats fed a soybean protein diet have been observed in hepatic phospholipid fatty acid patterns (Sjöblom, L., and Eklund, A., Biochim. Biophys. Acta 1004, 187-192, 1990). The influence of these two diets on the delta 6 desaturase activity was investig...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02544003

    authors: Lindholm M,Eklund A

    更新日期:1991-02-01 00:00:00

  • Effects of dietary corn oil and salmon oil on lipids and prostaglandin E2 in rat gastric mucosa.

    abstract::Three groups of male rats were fed either a corn oil-enriched diet (17%, w/w), a salmon oil-enriched diet (12.5%) supplemented with corn oil (4.5%) or a low-fat diet (4.4%) for eight wk to investigate the possible relationships between dietary fatty acids and lipid composition, and prostaglandin E2 level and phospholi...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535665

    authors: Grataroli R,Léonardi J,Charbonnier M,Lafont R,Lafont H,Nalbone G

    更新日期:1988-07-01 00:00:00

  • Palmitic acid and oleic acid differentially regulate choline transporter-like 1 levels and glycerolipid metabolism in skeletal muscle cells.

    abstract::Choline is an essential nutrient required for the biosynthesis of membrane lipid phosphatidylcholine (PtdCho). Here we elucidate the mechanism of how palmitic acid (PAM) and oleic acid (OLA) regulate choline transporter-like protein 1 (CTL1/SLC44A1) function. We evaluated the mechanism of extracellular and intracellul...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-014-3925-4

    authors: Schenkel LC,Bakovic M

    更新日期:2014-08-01 00:00:00

  • Triglyceride sub-classes of various dog adipose tissue sites.

    abstract::Lipids were extracted from four dog adipose tissue sites, perirenal, pericardial, inguinal subcutaneous, and mesenteric. The triglycerides were purified by thin-layer chromatography and the sub-classes separated by silver nitrate-silica gel plates. Gas chromatography was used to delineate the fatty acid composition of...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02530899

    authors: Gold M

    更新日期:1968-11-01 00:00:00

  • Proteolytic susceptibility of platelet low density lipoprotein receptor.

    abstract::In order to further characterize low density lipoprotein (LDL)-platelet interaction, we investigated the effect of protease pretreatment of human platelets on the subsequent binding of iodinated LDL (125I-LDL). Our results showed that the platelet LDL receptor had a proteolytic susceptibility different from that of bo...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02537484

    authors: Pedreño J,Fernández R

    更新日期:1995-10-01 00:00:00

  • Regulation of very low density lipoprotein apo B metabolism by dietary fat saturation and chain length in the guinea pig.

    abstract::Studies investigated the effects of dietary fatty acid composition and saturation on the regulation of very low density lipoprotein (VLDL) apo B flux, clearance, and conversion to low density lipoprotein (LDL) in guinea pigs fed semipurified diets containing 15% (w/w) corn oil (CO), lard (LA), or palm kernel oil (PK)....

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-998-0176-z

    authors: Abdel-Fattah G,Fernandez ML,McNamara DJ

    更新日期:1998-01-01 00:00:00

  • Isoprenoid fatty acids from marine sponges. Are sponges selective?

    abstract::The burrowing sponges Anthosigmella varians and Spheciospongia vesparium were found to be rich in the isoprenoid phospholipid fatty acid 4,8,12-trimethyltridecanoic (5.2% and 23%, respectively, of the total fatty acid composition), while the burrowing sponge Chondrilla nucula and the demosponge Agelas dispar contained...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02533980

    authors: Carballeira NM,Maldonado L,Porras B

    更新日期:1987-10-01 00:00:00

  • Metabolism of meadowfoam oil fatty acids in mice.

    abstract::Meadowfoam oil is unusual because over 95% of the fatty acids are 20- and 22-carbon aliphatic acids with cis double bonds located principally at the 5- and/or 13-position. Since little information is available on the metabolism of the 5c-20:1 and 5c,13c-22:2 fatty acids, an exploratory study in mice was conducted to i...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535623

    authors: Emken EA,Adlof RO,Abraham S

    更新日期:1991-09-01 00:00:00

  • Dual action of neutral sphingomyelinase on rat hepatocytes: activation of cholesteryl ester metabolism and biliary cholesterol secretion and inhibition of VLDL secretion.

    abstract::To address the role of cell membrane neutral sphingomyelinase (EC 3.1.4.12; SMase) in the regulation of cholesterol metabolism in the liver parenchymal cell, we examined the effect of exogenous neutral SMase on the metabolism of cholesteryl esters and the secretion of VLDL and biliary lipids in isolated rat hepatocyte...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-003-1031-y

    authors: Liza M,Chico Y,Fresnedo O,Ochoa B

    更新日期:2003-01-01 00:00:00

  • Effect of lecithin on jejunal absorption of micellar lipids in man and on their monomer activity in vitro.

    abstract::The effect of lecithin on jejunal absorption of fatty acids and octadecenoylglycerol was studied in healthy volunteers with a jejunal perfusion system which excluded pancreatic and biliary secretions from the test segment. Lecithin significantly reduced the absorption of oleic acid (P less than 0.05) and octadecenoylg...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02533424

    authors: Ammon HV,Thomas PJ,Phillipis SF

    更新日期:1979-04-01 00:00:00

  • Quantification, characterization and fatty acid composition of lysophosphatidic acid in different rat tissues.

    abstract::The amount and composition of lysophosphatidate present in different rat tissues have been estimated by an internal standard method in which a synthetic unnatural isomer (1-heptadecanoyl-rac-glycerol-3-phosphate) was added to the total lipid extracts, and the fatty acid composition of purified lysophosphatidate was de...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535172

    authors: Das AK,Hajra AK

    更新日期:1989-04-01 00:00:00

  • Effect of dietary vitamin E upon fluorescent compounds of the rat uterus.

    abstract::Several water soluble and organic solvent soluble fluorescent peaks were observed in extracts of uteri from vitamin E deficient or supplemented rats following Sephadex column chromatography and spectrophotofluorometric analysis. Levels of one of the organic and two of the water soluble fluorescent peaks were found to ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02534725

    authors: Csallany AS,Ayaz KL,Menken BZ

    更新日期:1984-12-01 00:00:00

  • Nonalcoholic components in wine reduce low density lipoprotein cholesterol in normocholesterolemic rats.

    abstract::Using an experimental model that enables the effects of alcohol to be distinguished from the effects of the nonalcoholic components present in wine, we determined whether wine has effects other than those of alcohol on the metabolism of cholesterol. Male rats were fed a standard diet and had free access to water and e...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-001-0732-6

    authors: Cascón E,Roig R,Ardèvol A,Salvadó MJ,Arola L,Bladé C

    更新日期:2001-04-01 00:00:00

  • Regulation of cholesterol synthesis in isolated epithelial cells of human small intestine.

    abstract::We have investigated the regulation of cholesterol synthesis in isolated human small intestine epithelial cells (enterocytes). It was established that the amount of cholesterol synthesized increased linearly with the incubation time and the number of cells in the incubation mixture; the synthesis was suppressed by 7-k...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535408

    authors: Sviridov DD,Safonova IG,Talalaev AG,Repin VS,Smirnov VN

    更新日期:1986-12-01 00:00:00

  • Separation and quantitation of mono-, di-, and triglycerides and free oleic acid using thin-layer chromatography with flame-ionization detection.

    abstract::alpha-Monoolein was prepared from glycidol and oleic acid by the regioselective opening of glycidol in the presence of an anionic resin. During the reaction, the lipochemical synthesis medium becomes enriched in monoolein, the effective emulsifying agent. This mixture can be analyzed by thin-layer chromatography coupl...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02522406

    authors: Peyrou G,Rakotondrazafy V,Mouloungui Z,Gaset A

    更新日期:1996-01-01 00:00:00

  • Novel long-chain diol phospholipids from some bacteria belonging to the class Thermomicrobia.

    abstract::Polar lipids of bacteria from the class Thermomicrobia are known to contain long-chain 1,2-diols instead of glycerol, although the nature of polar head groups has not been investigated. We have studied phospholipid classes of two species from the class Thermomicrobia-Sphaerobacter thermophilus and Thermomicrobia sp. W...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-014-3979-3

    authors: Lagutin K,MacKenzie A,Houghton KM,Stott MB,Vyssotski M

    更新日期:2015-03-01 00:00:00

  • Response of plasma lipids to dietary cholesterol and wine polyphenols in rats fed polyunsaturated fat diets.

    abstract::This experiment was designed to evaluate the effects of dietary red wine phenolic compounds (WP) and cholesterol on lipid oxidation and transport in rats. For 5 wk, weanling rats were fed polyunsaturated fat diets (n-6/n-3 = 6.4) supplemented or not supplemented with either 3 g/kg diet of cholesterol, 5 g/kg diet of W...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-000-0610-2

    authors: Frémont L,Gozzelino MT,Linard A

    更新日期:2000-09-01 00:00:00