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alkyl glycerol

Jung Eun Jang, Han-Sol Park, Hyun Ju Yoo, In-Jeoung Baek, Ji Eun Yoon, Myoung Seok Ko, Ah-Ram Kim, Hyoun Sik Kim, Hye-Sun Park, Seung Eun Lee, Seung-Whan Kim, Su Jung Kim, Jaechan Leem, Yu Mi Kang, Min Kyo Jung, Chan-Gi Pack, Chong Jai Kim, Chang Ohk Sung, In-Kyu Lee, Joong-Yeol Park, José C Fernández-Checa, Eun Hee Koh, Ki-Up Lee
: Free cholesterol (FC) accumulation in the liver is an important pathogenic mechanism of nonalcoholic steatohepatitis (NASH). Plasmalogens, key structural components of the cell membrane, act as endogenous antioxidants and are primarily synthesized in the liver. However, the role of hepatic plasmalogens in metabolic liver disease is unclear. In this study, we found that hepatic levels of docosahexaenoic acid (DHA)-containing plasmalogens, expression of glyceronephosphate O-acyltransferase (Gnpat, the rate-limiting enzyme in plasmalogen biosynthesis), and expression of Pparα were lower in mice with NASH caused by accumulation of free cholesterol (FC) in the liver...
January 10, 2017: Hepatology: Official Journal of the American Association for the Study of Liver Diseases
Rong-Juan Feng, Xia Li, Zhen Zhang, Zhou Lu, Yuan Guo
The interfacial behavior of the benchmark zwitterionic phospholipid molecule dipalmitoylphosphatidylcholine (DPPC) has been extensively investigated by surface-selective vibrational sum frequency generation spectroscopy (VSFG). However, there is still a lack of agreement between various orientational measurements of phospholipid monolayers at the air/water interface, mainly because of the difficulty in assigning congested VSFG features. In this study, polarization-dependent VSFG measurements reveal a frequency shift between the in-plane and out-of-plane antisymmetric stretching modes of the terminal methyl groups in the DPPC alkyl tails, favoring the model of Cs local symmetry rather than the previously assumed C3v symmetry...
December 28, 2016: Journal of Chemical Physics
Birte Martin-Bertelsen, Anan Yaghmur, Henrik Franzyk, Sarah Justesen, Jacob J K Kirkensgaard, Camilla Foged
Synthetic analogues of the cell-wall lipid monomycoloyl glycerol (MMG) are promising as next-generation vaccine adjuvants. In the present study, the thermotropic phase behavior of an array of synthetic MMG analogues was examined by using simultaneous small- and wide-angle X-ray scattering under excess water conditions. The MMG analogues differed in the alkyl chain lengths and in the stereochemistry of the polar glycerol headgroup or of the lipid tails (native-like versus alternative compounds). All MMG analogues formed poorly hydrated lamellar phases at low temperatures and inverse hexagonal (H2) phases at higher temperatures prior to melting...
December 6, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
Cristian Vidal, Joaquín García-Álvarez, Alberto Hernán-Gómez, Alan R Kennedy, Eva Hevia
Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds...
December 23, 2016: Angewandte Chemie
Marta Rodríguez-Rodríguez, Patricia Llanes, Christian Pradel, Miquel A Pericàs, Montserrat Gómez
The effect of long-alkyl-chain amines in CuI-assisted azide-alkyne cycloadditions of terminal alkynes with organic azides in glycerol and other environmentally benign solvents (water, ethanol) has been examined. The presence of these additives favors the in situ formation of Cu(I) -based nanoparticles and results in an increase of the catalytic reactivity. In glycerol, liquid-phase transmission electron microscopy (TEM) analyses, enabled by the negligible vapor pressure of this solvent, proved that Cu(I) nanoparticles are responsible for the observed catalytic activity...
December 12, 2016: Chemistry: a European Journal
Ekaterina Ermolenko, Nikolay Latyshev, Ruslan Sultanov, Sergey Kasyanov
Biological active compounds, 1-O-alkyl-sn-glycerols (AG), were isolated from liver oil of the squid Berryteuthis magister. The main components of the initial lipids were 1-O-alkyl-2,3-diacyl-sn-glycerols (38.50 %) and triacylglycerols (24.26 %). The first step of separation was the alkaline hydrolysis of oil to form a lipid mixture consisting of AG, free fatty acids and cholesterol. AG were separated by double recrystallization from acetone at -20 °C and 1 °C. A simple procedure is proposed for obtaining AG with a purity of 99...
March 2016: Journal of Food Science and Technology
T A Foglia, K Maeda
The resolution of a series of racemic 1-alkyl-3-trityl-rac-glycerols and 1-alkyl-2-benzyl-rac-glycerols into their enantiomers by high-performance liquid chromatography (HPLC) was investigated. Of the racemic glycerol derivatives studied, only three (1,2-0-isopropylidene-rac-glycerol, 1,2-0-isopropylidene-3-benzyl-rac-glycerol and 1-hexadecyl-2-benzyl-rac-glycerol) could be resolved into their enantiomers. The compounds were resolved on a silica (10 μm) column coated with cellulose tribenzoate and eluted isocratically with hexane/isopropanol as mobile phase...
September 1991: Lipids
W J Hansen, R Murari, Y Wedmid, W J Baumann
Choline phospholipids can be conveniently synthesized by reaction of a lipophilic alcohol, such as diacylglycerol, with 2-bromoethyl dichlorophosphate followed by nucleophilic displacement of the bromine with trimethylamine. We found that the low yields often encountered in the initial phosphorylation step are particularly due to exchange of both chlorines for alkoxy functions (triester formation) and to chlorination of the alcohol by 2-bromoethyl dichlorophosphate. However, these drawbacks can be overcome by proper choice of the reaction medium and by optimizing other reaction conditions...
June 1982: Lipids
A Poulos, G A Thompson
The in vivo incorporation of 1-(14)C-palmitic acid and 1-0-[8,9-(3)H] hexadecyl glycerol (chimyl alcohol) by plasmodia of the slime mold,Physarum polycephalum has been studied.(14)C-palmitate rapidly enters ester and alkyl ether side chains of phospholipids, but alk-1-enyl side chains are labeled more slowly.(3)H-chimyl alcohol is incorporated into the alkyl ether phospholipids, which appear to undergo enzymatic desaturation, producing plasmalogens. The feasibility ofPhysarum as the source of a cell-free enzyme system for plasmalogen synthesis is discussed...
July 1971: Lipids
Birte Martin-Bertelsen, Karen S Korsholm, Carla B Roces, Maja H Nielsen, Dennis Christensen, Henrik Franzyk, Anan Yaghmur, Camilla Foged
The mycobacterial cell-wall lipid monomycoloyl glycerol (MMG) is a potent immunostimulator, and cationic liposomes composed of a shorter synthetic analogue (MMG-1) and dimethyldioctadecylammonium (DDA) bromide represent a promising adjuvant that induces strong antigen-specific Th1 and Th17 responses. In the present study, we investigated the supramolecular structure and in vivo adjuvant activity of dispersions based on binary mixtures of DDA and an array of synthetic MMG-1 analogues (MMG-2/3/5/6) displaying longer (MMG-2) or shorter (MMG-3) alkyl chain lengths, or variations in stereochemistry of the polar headgroup (MMG-5) or of the hydrophobic moiety (MMG-6)...
August 1, 2016: Molecular Pharmaceutics
D Vollhardt, G Brezesinski
1-Monopalmitoyl-rac-glycerol is omnipresent in numerous biological and applied systems. Systematic GIXD measurements of 1-monopalmitoyl-rac-glycerol monolayers are carried out over a large pressure interval at 5, 10, and 15 °C to construct the phase diagram on the basis of reliable 2D lattice structures. These studies are complemented by other monolayer characteristics, such as π-A isotherms and mesoscopic domain topographies. A phase transition is found between the two orthorhombic structures with NN and NNN tilted alkyl chains at low temperatures (5 and 10 °C)...
July 26, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
Camille Delude, Laetitia Fouillen, Palash Bhar, Marie-Josée Cardinal, Stephanie Pascal, Patricia Santos, Dylan K Kosma, Jérôme Joubès, Owen Rowland, Frédéric Domergue
Suberin is a complex hydrophobic polymer that acts as a barrier controlling water and solute fluxes and restricting pathogen infections. Suberin is deposited immediately outside of the plasmalemma in the cell wall of certain tissues such as endodermis of roots, aerial and underground periderms, and seed coats. Suberin consists of a variety of fatty acid derivatives polymerized with glycerol and phenolics. In this study, we show using liquid chromatography-tandem mass spectrometry and gas chromatography-mass spectrometry techniques that most of the fatty alcohols not covalently linked to the suberin polymer are in the form of alkyl hydroxycinnamates (AHCs), with alkyl caffeates predominating...
July 2016: Plant Physiology
Xiuniang Tan, Jianling Zhang, Tian Luo, Xinxin Sang, Chengcheng Liu, Bingxing Zhang, Li Peng, Wei Li, Buxing Han
The aggregation behavior of the ionic liquid (IL) 1-alkyl-3-methylimidazolium chloride with different alkyl chain lengths in a deep eutectic solvent (DES, composed of choline chloride and glycerol in a 1 : 2 mole ratio) was studied for the first time. The critical micellar concentration, micellar size and intermolecular interactions in IL/DES solutions were investigated by different techniques including the fluorescence probe technique, small angle X-ray scattering and Fourier transform infrared spectroscopy...
June 28, 2016: Soft Matter
Kevin W Becker, Felix J Elling, Marcos Y Yoshinaga, Andrea Söllinger, Tim Urich, Kai-Uwe Hinrichs
UNLABELLED: A new clade of archaea has recently been proposed to constitute the seventh methanogenic order, the Methanomassiliicoccales, which is related to the Thermoplasmatales and the uncultivated archaeal clades deep-sea hydrothermal vent Euryarchaeota group 2 and marine group II Euryarchaeota but only distantly related to other methanogens. In this study, we investigated the membrane lipid composition of Methanomassiliicoccus luminyensis, the sole cultured representative of this seventh order...
August 1, 2016: Applied and Environmental Microbiology
Irene M Wohlman, Gabriella M Composto, Diane E Heck, Ned D Heindel, C Jeffrey Lacey, Christophe D Guillon, Robert P Casillas, Claire R Croutch, Donald R Gerecke, Debra L Laskin, Laurie B Joseph, Jeffrey D Laskin
Vesicants including sulfur mustard (SM) and nitrogen mustard (NM) are bifunctional alkylating agents that cause skin inflammation, edema and blistering. This is associated with alterations in keratinocyte growth and differentiation. Endogenous cannabinoids, including N-arachidonoylethanolamine (anandamide, AEA) and 2-arachidonoyl glycerol (2-AG), are important in regulating inflammation, keratinocyte proliferation and wound healing. Their activity is mediated by binding to cannabinoid receptors 1 and 2 (CB1 and CB2), as well as peroxisome proliferator-activated receptor alpha (PPARα)...
July 15, 2016: Toxicology and Applied Pharmacology
Laura Villanueva, Stefan Schouten, Jaap S Sinninghe Damsté
The lipid membrane is one of the most characteristic traits distinguishing the three domains of life. Membrane lipids of Bacteria and Eukarya are composed of fatty acids linked to glycerol-3-phosphate (G3P) via ester bonds, while those of Archaea possess isoprene-based alkyl chains linked by ether linkages to glycerol-1-phosphate (G1P), resulting in the opposite stereochemistry of the glycerol phosphate backbone. This 'lipid divide' has raised questions on the evolution of microbial life since eukaryotes are thought to have evolved from the Archaea, requiring a radical change in membrane composition...
April 26, 2016: Environmental Microbiology
Mira A M Behnam, Tom R Sundermann, Christian D Klein
Peptides and peptidomimetics with a C-terminal boronic acid group have prolific applications in numerous fields of research, but their synthetic accessibility remains problematic. A convenient, high yield synthesis of peptide-boronic acids on a solid support is described here, using commercially available 1-glycerol polystyrene resin. The method is compatible with Fmoc chemistry and offers a versatile approach to aryl and alkyl aminoboronic acids without additional purification steps.
May 6, 2016: Organic Letters
Philipp Aschauer, Srinivasan Rengachari, Joerg Lichtenegger, Matthias Schittmayer, Krishna Mohan Padmanabha Das, Nicole Mayer, Rolf Breinbauer, Ruth Birner-Gruenberger, Christian C Gruber, Robert Zimmermann, Karl Gruber, Monika Oberer
Monoglyceride lipases (MGLs) are a group of α/β-hydrolases that catalyze the hydrolysis of monoglycerides (MGs) into free fatty acids and glycerol. This reaction serves different physiological functions, namely in the last step of phospholipid and triglyceride degradation, in mammalian endocannabinoid and arachidonic acid metabolism, and in detoxification processes in microbes. Previous crystal structures of MGLs from humans and bacteria revealed conformational plasticity in the cap region of this protein and gave insight into substrate binding...
May 2016: Biochimica et Biophysica Acta
Pedro L Valero-Guillén, Isabel Fernández-Natal, Teresa Marrodán-Ciordia, Andreas Tauch, Francisco Soriano
Dermabacter hominis is a medically important actinobacterial inhabitant of human skin, although it is rarely implicated in infections. The lipid composition of D. hominis is revisited in this study in the context of its natural resistance to daptomycin, an antibiotic whose activity is influenced by membrane lipids. Thin layer chromatography and mass spectrometry revealed that this species contains phospholipids and glycolipids. Using electrospray ionization time of flight mass spectrometry (exact mass) and gas chromatography-mass spectrometry, the major phospholipid of D...
March 2016: Chemistry and Physics of Lipids
Mafumi Hishida, Ryuta Yanagisawa, Hatsuho Usuda, Yasuhisa Yamamura, Kazuya Saito
Towards a greater understanding of the effects of organic molecules in biomembranes, the effects of a flexible alkyl chain on the morphologies of phospholipid vesicles are investigated. Vesicles composed of 1,2-dipalmitoyl-sn-glycerol-3-phosphocholine and tetradecane (TD) rupture during cooling from the liquid-crystalline phase to the gel phase. A model calculation based on the size-dependent rupture probability indicates that the bending rigidity of the bilayer in the gel phase is more than 10 times higher than that without TD, resulting in the rupture arising from elastic stress...
January 28, 2016: Journal of Chemical Physics
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