Abstract:
:Nitration of unsaturated fatty acids is a (patho)physiologically important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (1), a linoleic acid metabolite, when exposed to nitrating agents of biological relevance. At pH 7.4 and at room temperature, reaction of 1 with peroxynitrite (ONOO-) as well as Fe2+-EDTA/H2O2/NO2- and horseradish peroxidase/H2O2/NO2- led to the formation of two nitration products, which could be isolated as the methyl esters and were identified as diastereoisomeric methyl (12S)-10,11-epoxy-12-hydroxy-9-nitromethylheptadecanoates by extensive 1H, 13C, 15N NMR and MS analysis.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Manini P,Camera E,Picardo M,Napolitano A,d'Ischia Mdoi
10.1016/j.chemphyslip.2007.09.007subject
Has Abstractpub_date
2008-01-01 00:00:00pages
51-61issue
1eissn
0009-3084issn
1873-2941pii
S0009-3084(07)00428-8journal_volume
151pub_type
杂志文章abstract::Cholesteryl-phosphoryl-choline (CPC), a hybrid between cholesterol and lecithin, is incorporated into sonicated liposomes and erythrocyte membranes similarly to cholesterol. The effect of CPC on lipid microviscosity and degree of order is smaller, but not significantly than that of cholesterol. It is proposed that CPC...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(79)90094-x
更新日期:1979-04-01 00:00:00
abstract::The properties of cholesterol in bilayers of egg phosphatidylcholine (PC) were investigated directly by means of 2H-NMR of specifically-deuterated species (C3, C7, C26, C27). Quadrupole splittings were a measure of molecular ordering, and relaxation times T1 and T2e were indicators of rates of motion. The importance o...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(82)90072-x
更新日期:1982-12-01 00:00:00
abstract::The indolic plant hormone, indole-3-acetic acid (IAA), mediated the transport of Mn2+ and other ions into small unilamellar vesicles prepared from soybean phosphatidylinositol (PI) and this process has been studied using 31P nuclear magnetic resonance spectroscopy (NMR). The rate of Mn2+ movement into PI vesicles is d...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(92)90010-m
更新日期:1992-04-01 00:00:00
abstract::Phosphatidylserine (PS) is an aminophospholipid that is prone to glycation. In oxidative conditions, glycated PS may lead to the formation of Amadori compounds and advanced glycated end products (AGEs), which are known to accumulate in diabetic patients. Nevertheless, there have been no studies that identified product...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2013.05.005
更新日期:2013-09-01 00:00:00
abstract::Cold atmospheric plasma (CAP) is an emerging source for the locally defined delivery of reactive species, and its clinical potential has been identified in the control of inflammatory processes, such as acute and chronic wounds, or cancerous lesions. Lipids, due to their localization and chemical structure as ideal ta...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2019.104786
更新日期:2020-01-01 00:00:00
abstract::The dicyclohexylborane-mediated addition of allene 1 to (E)-2-tridecenal affords a quaternary protected 2-amino-2-vinyl-1,3-diol in good yield as a single diastereomer. This compound is readily transformed into the four stereoisomers of the quaternary (E)-2-vinyl analogs of sphingosine. The metabolic fate and the effe...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2017.04.008
更新日期:2017-06-01 00:00:00
abstract::2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydrid...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2009.08.001
更新日期:2010-01-01 00:00:00
abstract::The properties of dipalmitoylphosphatidylcholine (DPPC):6-ketocholestanol bilayer at 50 mol% sterol were studied using the molecular dynamics simulation technique. Our simulations were performed at constant pressure and temperature on a nanosecond time scale. Data from this simulation were compared to the results of o...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(01)00160-8
更新日期:2001-07-01 00:00:00
abstract::The antioxidant activity during storage at 30 degrees C of quercetin, myricetin and alpha-tocopherol in small unilamellar liposomes has been investigated. Myricetin was more effective than alpha-tocopherol as an antioxidant in liposomes under all conditions studied. At pH 5.4 with a concentration of 10(-2) mol/mol pho...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(98)00098-x
更新日期:1998-12-01 00:00:00
abstract::Small unilamellar liposomes were made of dipalmitoyl-phosphatidylcholine and dioleoyl-phosphatidylcholine, and photosensitized by a symmetrically or an asymmetrically substituted glycosilated tetraphenyl-porphyrin derivative. As differential scanning calorimetry and electron paramagnetic resonance spectroscopy (EPR) r...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2006.10.005
更新日期:2007-02-01 00:00:00
abstract::Perturbations induced by ethylazinphos on the physical organization of dipalmitoylphosphatidylcholine (DPPC) and DPPC/cholesterol membranes were studied by differential scanning calorimetry (DSC) and fluorescence polarization of 2-, 6-, 12-(9-anthroyloxy) stearic acids and 16-(9-anthroyloxy) palmitic acid. Ethylazinph...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(98)00105-4
更新日期:1999-02-01 00:00:00
abstract::Lipids have a variety of physiological roles, ranging from structural and biophysical contributions to membrane functions to signaling contributions in normal and abnormal physiology. This review highlights some of the contributions made by Robert Bittman to our understanding of lipid assemblies through the production...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2015.10.005
更新日期:2016-01-01 00:00:00
abstract::Several cardiovascular risk factors are characterized by the coexistence of low-grade inflammation, enhanced oxidative stress and lipid peroxidation. It has been hypothesized that F2-isoprostanes, a product of in vivo lipid peroxidation, may transduce the effects of metabolic and hemodynamic abnormalities into increas...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/j.chemphyslip.2003.10.001
更新日期:2004-03-01 00:00:00
abstract::We investigated the effect of pegylation on the physical stability, morphology and membrane integrity of arsonoliposomes. Arsonoliposomes composed of distearoylglycerophosphocholine (DSPC), cholesterol (Chol) and the palmitoyl side chain arsonolipid (with concentrations ranging from 0 mol% [DSPC/Chol vesicles] to 53 m...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2005.11.003
更新日期:2006-02-01 00:00:00
abstract::Phospholipid vesicles like erythrocyte ghosts [1] have been shown to display trends in freeze-thaw injury with Group I ions which are non-monotonic in nature. That is to say, the relative extent of injury with such ions, measured as calcein release, does not follow a lyotropic series related solely to the hydrated ion...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(91)90006-w
更新日期:1991-09-01 00:00:00
abstract::2-N-(Hexadecanoyl)-amino-4-nitrophenyl phosphorylcholine-hydroxide a compound resembling sphingomyelin is synthesized. It is cleaved by sphingomyelinase to the chromogenic N-acylaminonitrophenyl moiety. Phospholipase C preparations do not hydrolyze this compound. The starting material is 2-amino-4-nitrophenol which wh...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(76)90015-3
更新日期:1976-02-01 00:00:00
abstract::Understanding how stereochemistry affects interactions with cell membranes is important for effective drug development. Chirality has been shown to greatly effect pharmaceutical distribution and metabolism within the cell. However it has been thought that interactions with, and passive diffusion through, the membrane ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2018.05.002
更新日期:2018-08-01 00:00:00
abstract::The study on aggregation capacity of novel imidazolium-containing amphiphiles of 1-(2-hydroxyethyl)alkylimidazolium bromide series and their interaction with bio-objects (DNA decamer, bovine serum albumin, phospholipid) was performed. It was revealed that introduction of hydroxyethyl moiety into the surfactant molecul...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2019.104791
更新日期:2019-09-01 00:00:00
abstract::The diffusion of a lipid fluorescent analogue across tight junctions in MDCK-I cells was studied by FRAP measurements. Cells were labelled with C6-NBD-PC at the apical cell membrane. Transepithelial resistance of MDCK-I cells was found to be higher than 3000 omega x cm2, which indicates the presence of a very tight ep...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(94)90066-3
更新日期:1994-05-23 00:00:00
abstract::Monolactone (NeuAc1-9NeuAc linkage) formation of a ganglioside, GD1b, was observed at 20 degrees C on solutions ranging in concentration from 0.008 to 1.7 mM and in pH from 2 to 8.1, by following the change of ellipicity at 235 nm, where lactonized gangliosides showed a strong Cotton effect. The lactonization was foun...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(94)90051-5
更新日期:1994-03-31 00:00:00
abstract::Reported herein is the synthesis of (+)- and (-)-(1,3/2)-1-O-(phosphocholine)-2,3-O-dihexanoylcyclopentane-1,2, 3-triol. These are the enantiomers of a contrained analogue of dihexanoylphosphatidylcholine in which the glycerol backbone is replaced by all-trans cyclopentane-1,2,3-triol. Evidence is presented to demonst...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(88)90017-5
更新日期:1988-03-01 00:00:00
abstract::Phosphoinositide 3-kinase (PI 3-kinase) is a key signaling enzyme implicated in a variety of receptor-stimulated cell responses. Stimulation of receptors possessing (or coupling to) protein-tyrosine kinase activates heterodimeric PI 3-kinases, which consist of an 85-kDa regulatory subunit (p85) containing Src-homology...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/s0009-3084(99)00020-1
更新日期:1999-04-01 00:00:00
abstract::We found that extracellular addition of 2% bovine serum albumin (BSA) to a suspension of rabbit platelets after stimulation with platelet-activating factor resulted in a biphasic extraction of [3H]1-O-alkyl-2-O-methyl (or 2-O-methylcarbamyl)-sn-glycero-3-phosphocholine. A fast phase of extraction of the phospholipid p...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(97)02664-9
更新日期:1997-03-28 00:00:00
abstract::Delta(9)-Tetrahydrocannabinol (delta(9)-THC), the primary psychoactive constituent of marijuana (Cannabis sativa), is known to bind to two cannabinoid receptors: CB(1) receptors, located primarily in the brain, and CB(2) receptors, located primarily in the periphery. Recent research has suggested that other cannabinoi...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/s0009-3084(02)00146-9
更新日期:2002-12-31 00:00:00
abstract::A series of long-chain methyl esters with vicinal oxo groups (1,2-diones; 1,2-diketones) were synthesized by potassium permanganate-based oxidation of methyl esters of mono-unsaturated fatty acids. The presence of two additional carbonyl groups may facilitate the synthesis of other derivatives. The starting materials ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(02)00014-2
更新日期:2002-05-01 00:00:00
abstract:BACKGROUND:In this study, we aimed to compare the serum lipid profile and fatty acid (FA) compositions of erythrocyte membrane (EM) and plasma in three different patient groups (group 1: type 2 diabetes mellitus (T2DM)+end-stage renal disease (ESRD), group 2: ESRD, group 4: T2DM) and healthy controls (group 3) simultan...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2013.12.011
更新日期:2014-02-01 00:00:00
abstract::Thio analogs of platelet activating factor (PAF) are of great interest because they exhibit antineoplastic properties both in vitro and in vivo. In contrast to most known anticancer agents, these lipids appear not to act through the synthesis and function of DNA and, therefore, offer a new avenue of approaching cancer...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(96)02615-1
更新日期:1996-11-01 00:00:00
abstract::Under condition of ROS formation in lipid membranes, free radical reactions can proceed in both hydrophobic (peroxidation of lipids, POL) and polar (free radical fragmentation) parts of the bilayer. Free-radical fragmentation is typical for the lipids containing a hydroxyl group in β-position with respect to an ester ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2013.10.010
更新日期:2014-01-01 00:00:00
abstract::The proteolytic activity of an aspartyl protease of Mucor miehei was correlated with the adsorption of the protease to lipid vesicles. It was observed that the presence of phosphatidylethanolamines (PE's) in the membrane increased the enzyme activity in a 20% in the gel phase and 10% in the fluid phase. The effects of...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(02)00188-3
更新日期:2003-01-01 00:00:00
abstract::Neutron scattering is a powerful tool to study relaxation processes in biological membrane mimics in space and time. Combining different inelastic and quasielastic neutron scattering techniques, a large dynamic range can be covered: from atomic to mesoscopic lengths and from femto- to some hundreds of nanoseconds in t...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/j.chemphyslip.2017.05.009
更新日期:2017-08-01 00:00:00