Abstract：
:Isoprostanes (IsoPs) are a complex family of compounds produced, in vivo, from peroxidation of polyunsaturated fatty acids (AA, DHA, EPA, alpha-linolenic) via a free-radical-catalyzed mechanism. Carbocyclic annulations are extremely important reactions and the stereocontrolled intramolecular free-radical cyclization has emerged as a powerful tool for carbon-carbon bond formation in synthetic chemistry. The hex-5-enyl radical cyclization is the most well-known for the synthesis of cyclopentane rings. After a short review of the literature, concerning the total synthesis of isoprostanes and intermediates, we will present our own contributions on the preparation of chiral cyclopentane rings from glucose leading to new isoprostanes. This study allowed us to control the cyclization outcome to yield the all-syn and/or syn-anti-syn precursors which permit us to the total synthesis of a large set of iso-, neuro-, and phytoprostanes.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Durand T,Guy A,Henry O,Roland A,Bernad S,El Fangour S,Vidal JP,Rossi JCdoi
10.1016/j.chemphyslip.2003.10.008subject
Has Abstractpub_date
2004-03-01 00:00:00pages
15-33issue
1-2eissn
0009-3084issn
1873-2941pii
S0009308403001579journal_volume
128pub_type
杂志文章,评审abstract：:The interaction of the amphoteric surfactant N-dodecyl-N,N-dimethylbetaine (C12-Bet) with phosphatidylcholine (PC) liposomes was investigated. Permeability alterations were detected as a change in 5(6)-carboxyfluorescein (CF) released from the interior of vesicles and bilayer solubilization as a decrease in the static...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(98)00045-0
更新日期：1998-07-01 00:00:00
abstract：:A new polymerizable surfactant, 12-methacryloyl dodecylphosphocholine (MDPC), has been synthesized using a three-step procedure in moderate yield. Phase transitions were characterized by DSC and phase behavior in water was determined by surface tension and polarizing microscopy. MDPC showed typical surfactant behavior...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2010.03.001
更新日期：2010-05-01 00:00:00
abstract：:The gel-like liquid phase transition of dimyristoylphosphatidylcholine (DMPC) large unilamellar vesicles prepared by reverse phase evaporation has been investigated in buffers containing ethanol by quasi-elastic light scattering (QLS) and vibrational (infrared and Raman) spectroscopy. With the QLS technique, the relat...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90001-1
更新日期：1988-12-01 00:00:00
abstract：:The polymorphic behavior of three series of tris-homoacyl (C14:0, C16:0 and C18:0) cyclopentane-1,2,3-triol analogs of the natural saturated triglycerides has been studied using differential thermal analysis, Fourier transform infrared spectroscopy, and X-ray diffraction. It was found that the triglyceride analogs der...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(77)90003-2
更新日期：1977-03-01 00:00:00
abstract：:The stratum corneum (SC), the outermost layer of the mammalian skin, is the main skin barrier. Ceramides (CERs) as the major constituent of the SC lipid matrix are of particular interest. At the moment, 11 classes of CERs are identified, but the effect of each single ceramide species is still not known. Therefore in t...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2009.10.007
更新日期：2010-01-01 00:00:00
abstract：:A study of the vibrational behavior of five saturated monoacid triacylglycerides is performed by Raman spectroscopy at room temperature in the 3100-500 cm(-1) spectral range. The splitting of the CO stretching mode leads to conclude on the existence of two or three geometries of CO in the "knot" group OCO. The CO stre...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.12.009
更新日期：2005-04-01 00:00:00
abstract：:The 13C- and 31P-NMR spectra and DSC thermograms of unsonicated dispersions consisting of phospholipids of varying methylation stages of the propanolamine head group were investigated. Methylation of the head group was accompanied by a corresponding reduction in the phase transition temperatures. In the liquid crystal...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(77)90069-x
更新日期：1977-12-01 00:00:00
abstract：:In the last 30 years, ceramides have been found to mediate a myriad of biological processes. Ceramides have been recognized as bioactive molecules and their metabolizing enzymes are attractive targets in cancer therapy and other diseases. The molecular mechanism of action of cellular ceramides are still not fully esta...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2018.09.013
更新日期：2018-11-01 00:00:00
abstract：:An investigation into the effect of alpha-tocopherol on phospholipid model membranes has been carried out by electron spin resonance (ESR) and saturation transfer ESR. The use of stearic acid and of perdeutero -di-t-butyl nitroxide spin probes has allowed us to monitor, in particular, the effect of alpha-tocopherol on...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90129-f
更新日期：1990-03-01 00:00:00
abstract：:Cardiolipins (CLs) are ancient and unusual dimeric phospholipids localized in the plasma membrane of bacteria and in the inner mitochondrial membrane of eukaryotes. In mitochondria, two types of asymmetries--trans-membrane and molecular--are essential determinants of CL functions. In this review, we describe CL-based ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2013.11.010
更新日期：2014-04-01 00:00:00
abstract：:Bile acids directly related to liver and intestinal function are used as indicators of hepatobiliary and intestinal diseases. Here, we have designed and realized a capillary sensory platform for the detection of bile acids using liquid crystals (LCs). LC droplets confined in micro-capillaries are homeotropically align...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2017.02.003
更新日期：2017-04-01 00:00:00
abstract：:From 81 of human plasma of blood-group A Lea nonsecretors three different Lea blood-group active ceramide pentasaccharides (a total of 4.65 mg) have been isolated, all revealing glucose, galactose, N-acetylglucosamine and fucose in molar ratios of 1 : 2 : 1 : 1 as determined by gas liquid chromatography. A fourth bloo...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(78)90040-3
更新日期：1978-09-01 00:00:00
abstract：:In X-ray diffraction studies of hydrated (greater than 60%) cholesterol/dioleoylphosphatidylcholine mixtures the lipid packing band showed an abrupt transition from liquid crystal-type to gel-type position and definition at a temperature which decreased progressively to almost -50 degrees C as the proportion of choles...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90115-6
更新日期：1988-01-01 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：:Determining the particle size and number of lipoprotein components found in blood plasma (HDL, LDL and VLDL) has become an important clinical tool in diagnosing risk of cardiovascular disease. Proton (1H) NMR spectroscopy methods to quantify lipoprotein particle subclasses have been advancing since NMR lineshape analy...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2020.104874
更新日期：2020-05-01 00:00:00
abstract：:The influence of the temperature on the adsorption of monomeric and micellar solutions of the anionic surfactant sodium dodecyl sulfate (SDS) on phosphatidylcholine (PC) liposomes was investigated using the fluorescent probe 2-(p-toluidinyl)-naphthalene-6-sodium sulfonate (TNS). The number of adsorbed molecules was qu...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(03)00022-7
更新日期：2003-06-01 00:00:00
abstract：:The importance of phospholipases in cellular signaling and 1-alkylglycerophosphocholine acetyltransferase in the formation of platelet-activating factor (PAF) has stimulated demand for methods to measure these enzyme activities in inflammatory cells. Most of the assays currently used rely on radiolabeled substrates. W...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(95)02504-9
更新日期：1996-01-25 00:00:00
abstract：:Low density lipoprotein (LDL) cholesterol is known to be oxidized both in vitro and in vivo giving rise to oxygenated sterols. Conflicting results, however, have been reported concerning both the nature and the relative concentrations of these compounds in oxidized human LDL. We examined the extracts obtained from Cu(...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(92)90057-v
更新日期：1992-10-01 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：:We performed differential scanning calorimetric (DSC) and Fourier transform infrared (FTIR) spectroscopic studies of the effects of cholesterol (CHOL), 7-dehydrocholeterol (7DHC) and desmosterol (DES) on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine (DPPC) bilayer membranes. 7DHC a...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2015.09.002
更新日期：2015-10-01 00:00:00
abstract：:Racemic 1-O-(2-methyloctadecyl)-2-O-acetyl-glycero-3-phosphocholine, a branched chain PAF species, was prepared by chemical synthesis and investigated for biological activity on human blood platelets in vitro. The synthesis started from 2-O-benzylglycerol and 2-methyloctadecyl-1-methyl sulfonate and was accomplished i...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(91)90017-6
更新日期：1991-11-01 00:00:00
abstract：:(1) An analysis has been conducted of the lipids present in three obligately anaerobic bacteria isolated from the ovine rumen belonging to the genus Butyrivibrio. Two of these organisms are rich in phospholipase (A1 + A2) activity, and appear to be different strains of the species fibrisolvens. (2) The only N-containi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(76)90067-0
更新日期：1976-10-01 00:00:00
abstract：:The application of infrared spectroscopy to the physicochemical characterization of glycolipids as biologically important membrane constituents is described. In this contribution, the analysis of diacyl- and sphingosine-based (cerebroside, ganglioside) oligosaccharides and the class of lipid A-anchored lipooligo- and ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/s0009-3084(98)00078-4
更新日期：1998-11-01 00:00:00
abstract：:In the first part of this article, chemical and physical stability of aqueous liposome dispersions have been addressed. Chemical stability of phospholipids has been considered in two parts: oxidation and hydrolysis. Major attention has been paid to hydrolysis kinetics of phospholipids as a function of pH, temperature,...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(93)90053-6
更新日期：1993-09-01 00:00:00
abstract：:Oxysterols are oxidized products of cholesterol that play several roles in various pathophysiological processes, including the control of lipid metabolism, immunological processes, and cytotoxicity. Mesenchymal stem cells are multipotent cells with properties of self-renewal and the ability to differentiate into other...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2017.06.009
更新日期：2017-10-01 00:00:00
abstract：:Age-related fluorescent and cross-linked proteins increase with lipid oxidation of tissues. The fluorophores and cross-links have been considered to be conjugated Schiff bases between amino groups of proteins and malonaldehyde. Our recent studies showed that the fluorophores produced in the in vitro reaction of protei...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(87)90054-5
更新日期：1987-07-01 00:00:00
abstract：:Apolipoprotein B-100 (apoB-100) is the major protein in low-density lipoprotein (LDL) and contains the ligand for binding LDL to its cell surface receptor. Lipoprotein [a] (Lp[a]) is a lipoprotein that consists of LDL and apolipoprotein [a] (apo[a]). The primary structure of apoB-100 has been determined by a combinati...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(94)90128-7
更新日期：1994-01-01 00:00:00
abstract：:The fertilising ability of human spermatozoa may be impaired by inflammations of the genital tract, although details of these processes are still unknown. Hypochlorous acid (HOCl), an important product of myeloperoxidase released from stimulated neutrophils, induces a concentration-dependent increase in externalisatio...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2005.02.015
更新日期：2005-06-01 00:00:00
abstract：:Some thermodynamic and structural aspects of propranolol-DPPC liposomes interaction were investigated by DSC and X-ray diffraction: the lamellar arrangement of the lipid matrix remains intact even at high concentrations of the drug (until 1:1 drug/lipid molar ratio). However, the bilayer thickness increases significan...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90171-m
更新日期：1990-09-01 00:00:00
abstract：:Infarcted porcine heart tissue and surrounding tissue were investigated for the content of plasmalogens and oxidatively derived corresponding alpha-hydroxyaldehydes as well as for products of lipid peroxidation, e.g. malondialdehyde, glyoxal, 2-hydroxyheptanal and oxygenated fatty acids. Oxidation products of unsatura...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(96)02557-1
更新日期：1996-07-30 00:00:00
