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Chemistry and Physics of Lipids

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https://www.readbyqxmd.com/read/28445710/stereoselective-preparation-of-quaternary-2-vinyl-sphingosines-and-ceramides-and-their-effect-on-basal-sphingolipid-metabolism
#1
Raquel Calderón, Nerea Mercadal, José Luis Abad, Xavier Ariza, Antonio Delgado, Jordi Garcia, Aleix Rodríguez, Gemma Fabriàs
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 effect of these compounds on the basal sphingolipid metabolism in human A549 lung adenocarcinoma cells has been studied, together with the ceramide analog of the most relevant vinylsphingosine derivative...
April 23, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28435101/interaction-of-glucocorticoids-and-progesterone-derivatives-with-human-serum-albumin
#2
Rola Abboud, Mohammad Akil, Catherine Charcosset, Hélène Greige-Gerges
Glucocorticoids (GCs) and progesterone derivatives (PGDs) are steroid hormones with well-known biological activities. Their interaction with human serum albumin (HSA) may control their distribution. Their binding to albumin is poorly studied in literature. This paper deals with the interaction of a series of GCs (cortisol, cortisone, prednisolone, prednisone, 6-methylprednisolone and 9-fluorocortisol acetate) and PGDs (progesterone, hydroxylated PGDs, methylated PGDs and dydrogesterone) with HSA solution (pH 7...
April 20, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28412174/experimentally-determined-tilt-and-bending-moduli-of-single-component-lipid-bilayers
#3
REVIEW
John F Nagle
Values of the bending modulus KC and the tilt modulus Kθ are reported for single component lipid bilayers. The lipids studied have the common names DOPC, DMPC, diC22:1PC, SOPC, POPC, diPhyPC, DLPC, DPPC, DHPC and DEPC, listed in the order of number of samples examined. The experimental method, thus far the only one that measures the tilt modulus of lipid bilayers, first obtains diffuse X-ray scattering data from oriented stacks of bilayers. The values of the moduli emerge from fitting the data to the accepted tilt-dependent continuum model for the free energy of a single bilayer, further enhanced by interactions between bilayers in the stack...
April 12, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28412173/spontaneous-formation-of-single-component-liposomes-from-a-solution
#4
Sopan M Phapal, Chandra Has, P Sunthar
The diameter of lipid vesicles is generally known to be determined by parameters external to the system, such as fluid shear, electric fields, co-surfactants, etc. We present a mechanism by which a system consisting of a single component lipid can spontaneously assemble from a solution phase to form monodisperse unilamellar vesicles of well-defined diameters dictated only by thermodynamic parameters intrinsic to the system. Here, the lipids self-assemble as vesicles when an aqueous phase diffusively replaces the original solvent in a macroscopically stationary (or quiescent) manner...
April 12, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28411018/charge-tagging-liquid-chromatography-mass-spectrometry-methodology-targeting-oxysterol-diastereoisomers
#5
William J Griffiths, Thomas Hearn, Peter J Crick, Jonas Abdel-Khalik, Alison Dickson, Eylan Yutuc, Yuqin Wang
The introduction of a hydroxy group to the cholesterol skeleton introduces not only the possibility for positional isomers but also diastereoisomers, where two or more isomers have different configurations at one or more of the stereocentres but are not mirror images. The differentiation of diastereoisomers is important as differing isomers can have differing biochemical properties and are formed via different biochemical pathways. Separation of diasterioisomers is not always easy by chromatographic methods Here we demonstrate, by application of charge-tagging and derivatisation with the Girard P reagent, the separation and detection of biologically relevant diastereoisomers using liquid chromatography - mass spectrometry with multistage fragmentation...
April 12, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28411017/biological-properties-of-propolis-extracts-something-new-from-an-ancient-product
#6
REVIEW
Nada Zabaiou, Allan Fouache, Amalia Trousson, Silvère Baron, Amar Zellagui, Mesbah Lahouel, Jean-Marc A Lobaccaro
Natural products are an interesting source of new therapeutics, especially for cancer therapy as 70% of them have botany origin. Propolis, a resinous mixture that honey bees collect and transform from tree buds, sap flows, or other botanical sources, has been used by ethnobotany and traditional practitioners as early in Egypt as 3000 BC. Enriched in flavonoids, phenol acids and terpene derivatives, propolis has been widely used for its antibacterial, antifungal and anti-inflammatory properties. Even though it is a challenge to standardize propolis composition, chemical analyses have pointed out interesting molecules that also present anti-oxidant and anti-proliferative properties that are of interest in the field of anti-cancer therapy...
April 11, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28408132/comparison-of-the-effects-of-major-fatty-acids-present-in-the-mediterranean-diet-oleic-acid-docosahexaenoic-acid-and-in-hydrogenated-oils-elaidic-acid-on-7-ketocholesterol-induced-oxiapoptophagy-in-microglial-bv-2-cells
#7
Meryam Debbabi, Amira Zarrouk, Maryem Bezine, Wiem Meddeb, Thomas Nury, Asmaa Badreddine, El Mostafa Karym, Randa Sghaier, Lionel Bretillon, Stéphane Guyot, Mohammad Samadi, Mustapha Cherkaoui-Malki, Boubker Nasser, Mondher Mejri, Sofien Ben-Hammou, Mohamed Hammami, Gérard Lizard
Increased levels of 7-ketocholesterol (7KC), which results mainly from cholesterol auto-oxidation, are often found in the plasma and/or cerebrospinal fluid of patients with neurodegenerative diseases and might contribute to activation of microglial cells involved in neurodegeneration. As major cellular dysfunctions are induced by 7KC, it is important to identify molecules able to impair its side effects. Since consumption of olive and argan oils, and fish is important in the Mediterranean diet, the aim of the study was to determine the ability of oleic acid (OA), a major compound of olive and argan oil, and docosahexaenoic acid (DHA) present in fatty fishes, such as sardines, to attenuate 7KC-induced cytotoxic effects...
April 10, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28389107/ceramide-binding-to-anandamide-increases-its-half-life-and-potentiates-its-cytotoxicity-in-human-neuroblastoma-cells
#8
Coralie Di Scala, Morgane Mazzarino, Nouara Yahi, Karine Varini, Nicolas Garmy, Jacques Fantini, Henri Chahinian
Anandamide (AEA) is a ubiquitous lipid that exerts neurotransmitter functions but also controls important biological functions such as proliferation, survival, or programmed cell death. The latter effects are also regulated by ceramide, a lipid enzymatically generated from sphingomyelin hydrolysis by sphingomyelinase. Ceramide has been shown to increase the cellular toxicity of AEA, but the mechanisms controlling this potentiating effect remained unclear. Here we have used a panel of in silico, physicochemical, biochemical and cellular approaches to study the crosstalk between AEA and ceramide apoptotic pathways...
April 4, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28365392/effects-of-seaweed-sterols-fucosterol-and-desmosterol-on-lipid-membranes
#9
Ole G Mouritsen, Luis A Bagatolli, Lars Duelund, Olav Garvik, John H Ipsen, Adam Cohen Simonsen
Higher sterols are universally present in large amounts (20-30%) in the plasma membranes of all eukaryotes whereas they are universally absent in prokaryotes. It is remarkable that each kingdom of the eukaryotes has chosen, during the course of evolution, its preferred sterol: cholesterol in animals, ergosterol in fungi and yeast, phytosterols in higher plants, and e.g., fucosterol and desmosterol in algae. The question arises as to which specific properties do sterols impart to membranes and to which extent do these properties differ among the different sterols...
March 30, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28363784/the-effect-of-cannabinoid-receptor-1-blockade-on-hepatic-free-fatty-acid-profile-in-mice-with-nonalcoholic-fatty-liver-disease
#10
Bojan Jorgačević, Danijela Vučević, Ivana Đuričić, Slađana Šobajić, Dušan Mladenović, Milena Vesković, Rada Ješić Vukićević, Tatjana Radosavljević
We used rimonabant to investigate the role of CB1 receptor on hepatic FFAs profile during NAFLD. Male mice C57BL/6 were divided into: control group fed with control diet 20 weeks (C; n=6); group fed with HFD 20 weeks (HF; n=6); group fed with control diet and treated with rimonabant after 18 weeks (R; n=9); group fed with HFD and treated with rimonabant after 18 weeks (HFR; n=10). Rimonabant (10mg/kg) was administered daily to HFR and R group by oral gavage. Rimonabant decreased liver palmitic acid proportion in HFR group compared to HF group (p<0...
March 29, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28347782/aggregation-of-t10-c12-conjugated-linoleic-acid-in-presence-of-natural-and-modified-cyclodextrins-a-physicochemical-thermal-and-computational-analysis
#11
Adrián Matencio, Francisco García-Carmona, José Manuel López-Nicolás
In this work the aggregation behavior of t10,c12 Conjugated linoleic acid (t10,c12-CLA) is presented for first time. The results show a c.m.c. of 25μM at pH 8 and 25°C. The encapsulation process with cyclodextrins (CDs) presented a 1:1 stoichiometry in all cases studied but the complexation constants were strongly dependent on the type of CDs used, the pH and temperature. Hydroxypropyl-beta-Cyclodextrin (HPβCD) was the best CD studied for encapsulating t10,c12-CLA. The resulting t10,c12-CLA-HPβCD complex showed a very high dependency on pH, which explains why a pKa of 4...
March 25, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28342541/continuous-gradient-temperature-raman-spectroscopy-and-differential-scanning-calorimetry-of-n-3dpa-and-dha-from-100-to-10%C3%A2-c
#12
C Leigh Broadhurst, Walter F Schmidt, Julie K Nguyen, Jianwei Qin, Kuanglin Chao, Steven R Aubuchon, Moon S Kim
Docosahexaenoic acid (DHA, 22:6n-3) is exclusively utilized in fast signal processing tissues such as retinal, neural and cardiac. N-3 docosapentaenoic acid (n-3DPA, 22:5n-3), with just one less double bond, is also found in the marine food chain yet cannot substitute for DHA. Gradient temperature Raman spectroscopy (GTRS) applies the temperature gradients utilized in differential scanning calorimetry (DSC) to Raman spectroscopy, providing a straightforward technique to identify molecular rearrangements that occur near and at phase transitions...
March 22, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28336451/effect-of-soybean-phosphatidylcholine-on-lipid-profile-of-bovine-oocytes-matured-in-vitro
#13
Caroline P Pitangui-Molina, Alessandra A Vireque, Alessandra Tata, Katia Roberta A Belaz, Vanessa G Santos, Christina R Ferreira, Marcos N Eberlin, Marcos Felipe Silva-de-Sá, Rui A Ferriani, Ana Carolina J S Rosa-E-Silva
The phospholipid (PL) composition of embryo and oocyte membranes affects thermal phase behavior and several physicochemical properties such as fluidity and permeability. The characterization of PL profiles and the development of suitable in vitro maturation (IVM) protocols, that are able to modify membrane's composition, may result in significant improvements in oocyte developmental potential and cryotolerance. Using soybean phosphatidylcholine (PC) as a model supplement, we evaluated the effect of PL supplementation during IVM on bovine cumulus-oocyte-complex (COC)...
March 21, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28322741/evidence-of-k-homeostasis-disruption-in-cellular-dysfunction-triggered-by-7-ketocholesterol-24s-hydroxycholesterol-and-tetracosanoic-acid-c24-0-in-158n-murine-oligodendrocytes
#14
Maryem Bezine, Meryam Debbabi, Thomas Nury, Rym Ben-Khalifa, Mohammad Samadi, Mustapha Cherkaoui-Malki, Anne Vejux, Jérôme de Sèze, Thibault Moreau, Mohamed El-Ayeb, Gérard Lizard
Imbalance in the homeostasis of K(+) ions has been reported to contribute to the pathogenesis of neurodegenerative diseases. 7-ketocholesterol (7KC), 24S-hydroxycholesterol (24S-OHC), and tetracosanoic acid (C24:0), often found at increased levels in patients with Alzheimer's disease, Multiple Sclerosis and X-ALD, are able to trigger numerous nerve cell dysfunctions. We therefore studied the impact of 7KC, 24S-OHC, and C24:0 on 158N murine oligodendrocytes, and determined their impact on K(+) homeostasis. The effects of 7KC, 24S-OHC and C24:0 on lipid membrane organization and membrane potential were examined with merocyanine 540 (MC540) and bis-(1,3-diethylthiobarbituric acid) trimethine oxonol (DiSBAC2(3)), respectively...
March 17, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28300539/interaction-of-dextran-derivatives-with-lipid-monolayers-and-the-consequential-modulation-of-the-film-properties
#15
Candelaria I Cámara, Natalia Wilke
Polysaccharides have been associated with various biological functions through their binding to membranes, but their specific role is still under debate. The aim of this work was to study the interaction of cationic and anionic polysaccharides with anionic and zwitterionic monolayers, at different subphase compositions, thus analyzing the influence of electrostatics on the interaction. The consequent effect of the polymer-lipid binding on the film properties was studied, with special interest in monolayer dynamics...
March 12, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28300538/improved-synthesis-of-glycine-taurine-and-sulfate-conjugated-bile-acids-as-reference-compounds-and-internal-standards-for-esi-ms-ms-urinary-profiling-of-inborn-errors-of-bile-acid-synthesis
#16
Elena Donazzolo, Antonina Gucciardi, Daniela Mazzier, Cristina Peggion, Paola Pirillo, Mauro Naturale, Alessandro Moretto, Giuseppe Giordano
Bile acid synthesis defects are rare genetic disorders characterized by a failure to produce normal bile acids (BAs), and by an accumulation of unusual and intermediary cholanoids. Measurements of cholanoids in urine samples by mass spectrometry are a gold standard for the diagnosis of these diseases. In this work improved methods for the chemical synthesis of 30 BAs conjugated with glycine, taurine and sulfate were developed. Diethyl phosphorocyanidate (DEPC) and diphenyl phosphoryl azide (DPPA) were used as coupling reagents for glycine and taurine conjugation...
March 12, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28267434/dietary-phytochemicals-in-the-protection-against-oxysterol-induced-damage
#17
REVIEW
Antonio Cilla, Amparo Alegría, Alessandro Attanzio, Guadalupe Garcia-Llatas, Luisa Tesoriere, Maria A Livrea
The intake of fruits and vegetables is associated with reduced incidence of many chronic diseases. These foods contain phytochemicals that often possess antioxidant and free radical scavenging capacity and show anti-inflammatory action, which are also the basis of other bioactivities and health benefits, such as anticancer, anti-aging, and protective action for cardiovascular diseases, diabetes mellitus, obesity and neurodegenerative disorders. Many factors can be included in the etiopathogenesis of all of these multifactorial diseases that involve oxidative stress, inflammation and/or cell death processes, oxysterols, i...
March 3, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28259649/role-of-the-liver-x-receptors-in-skin-physiology-putative-pharmacological-targets-in-human-diseases
#18
REVIEW
Zangbéwendé Guy Ouedraogo, Allan Fouache, Amalia Trousson, Silvère Baron, Jean-Marc A Lobaccaro
Liver X receptors (LXRs) are members of the nuclear receptor superfamily that have been shown to regulate various physiological functions such as lipid metabolism and cholesterol homeostasis. Concordant reports have elicited the possibility to target them to cure many human diseases including arteriosclerosis, cancer, arthritis, and diabetes. The high relevance of modulating LXR activities to treat numerous skin diseases, mainly those with exacerbated inflammation processes, contrasts with the lack of approved therapeutic use...
March 1, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28235449/regio-selective-lipase-catalyzed-hydrolysis-of-oxanorbornane-based-sugar-like-amphiphiles-at-air-water-interface-a-polarized-ft-irras-study
#19
Nirod Kumar Sarangi, M Ganesan, K M Muraleedharan, Archita Patnaik
Interfacial hydrolysis of oxanorbornane-based amphiphile (Triol C16) by Candida rugosa lipase was investigated using real-time polarized Fourier transform-infrared reflection absorption spectroscopy (FT-IRRAS). The kinetics of hydrolysis was studied by analyzing the ester carbonyl ν(CO) stretching vibration band across the two dimensional (2D) array of molecules at the confined interface. In particular, we demonstrate Triol C16 to form Michaelis-Menten type complex, like that of lipid-substrate analogues, where the Triol C16 head group remained accessible to the catalytic triad of the lipase...
February 22, 2017: Chemistry and Physics of Lipids
https://www.readbyqxmd.com/read/28235448/ir-spectroscopy-analysis-of-pancreatic-lipase-related-protein-2-interaction-with-phospholipids-1-discriminative-recognition-of-mixed-micelles-versus-liposomes
#20
Eduardo Mateos-Diaz, Jean-Claude Bakala N'Goma, Deborah Byrne, Sylvie Robert, Frédéric Carrière, Hélène Gaussier
Guinea pig pancreatic lipase-related protein 2 (GPLRP2) is an interesting model enzyme that can hydrolyze a large set of acylglycerols in vitro but displays however some selectivity depending on the supramolecular structure of substrate and the presence of surfactants like bile salts. We showed that GPLRP2 hydrolyzes 1,2-Dipalmitoyl phosphatidylcholine (DPPC) present in mixed micelles with sodium taurodeoxycholate (NaTDC) but not in multilamellar (MLV) and large unilamellar (LUV) vesicles of DPPC. After characterization of these lipid aggregates by dynamic light scattering (DLS), the discriminative recognition of DPPC in DPPC/NaTDC micelles versus MLV and LUV by an inactive variant (S152G) of GPLRP2 to avoid the effect of substrate hydrolysis was investigated using Fourier transform infrared spectroscopy (FTIR)...
February 21, 2017: Chemistry and Physics of Lipids
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