Analogs of natural lipids. II. Polymorphic behavior of the tris-homoacyl derivatives of cyclopentane-1,2,3-triols.

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 derived from the 1,2,3/0 and 1,2/3 cyclopentanetriols exhibit different polymorphic behavior than that of the natural triglycerides. The analogs derived from 1,3/2 cyclopentanetriol, however, were found to parallel the polymorphic behavior of the natural triglycerides quite closely. This polymorphic behavior is discussed in terms of the different configurations which the chains assume in each of the triglyceride analogs.

journal_name

Chem Phys Lipids

authors

Greenwald SM,Hancock AJ,Sable HZ,D'Esposito L,Koenig JL

doi

10.1016/0009-3084(77)90003-2

subject

Has Abstract

pub_date

1977-03-01 00:00:00

pages

154-69

issue

2

eissn

0009-3084

issn

1873-2941

pii

0009-3084(77)90003-2

journal_volume

18

pub_type

杂志文章
  • A fluorescence quenching study on protoporphyrin IX in a model membrane system.

    abstract::The interaction of protoporphyrin IX (3,7,12,15-tetramethyl-8, 13-divinyl-2,18-porphyrine-dipropionic acid) (PPIX) with unilamellar dimyristoyl-L-alpha-phosphatidylcholine (DMPC) phospholipid vesicles has been studied by means of steady-state fluorescence quenching spectroscopy. The method of fluorescence-quenching-re...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(96)02605-9

    authors: Kuszaj S,Kaszycki P,Wasylewski Z

    更新日期:1996-09-30 00:00:00

  • Determinants of F2-isoprostane biosynthesis and inhibition in man.

    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

    authors: Davì G,Falco A,Patrono C

    更新日期:2004-03-01 00:00:00

  • Cannabinoid pharmacology: implications for additional cannabinoid receptor subtypes.

    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

    authors: Wiley JL,Martin BR

    更新日期:2002-12-31 00:00:00

  • Local anesthetics induce interdigitation and thermotropic changes in dipalmitoylphosphatidylcholine bilayers.

    abstract::The molecular mechanism underlying the action of local anesthetics is still elusive. Phenylethanol (PEtOH) is an ingredient of essential oils with a rose-like odor and has been used as a local anesthetic. In this work, we have explored the effect of PEtOH on thermotropic behavior and organization of dipalmitoylphospha...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2017.12.003

    authors: Reddy ST,Shrivastava S,Chattopadhyay A

    更新日期:2018-01-01 00:00:00

  • Properties of lecithin-dodecaprenol macrovesicular bilayer membranes.

    abstract::The ionic transport properties, capacitance and breakdown voltage of bilayer macrovesicles made from lecithin, dodecaprenol and their mixtures have been studied. The electrical measurements showed that polyprenol in lipid bilayers increases membrane permeability and elasticity, and decreases membrane thickness. Some p...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(86)90116-7

    authors: Janas T,Kuczera J,Chojnacki T,Krajewska-Rychlik I

    更新日期:1986-03-01 00:00:00

  • Liquid chromatography-tandem mass spectrometry of phosphatidylserine advanced glycated end products.

    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

    authors: Maciel E,da Silva RN,Simões C,Melo T,Ferreira R,Domingues P,Domingues MR

    更新日期:2013-09-01 00:00:00

  • Effect of additives on isothermal crystallization kinetics and physical characteristics of coconut oil.

    abstract::The effect of lauric acid and low-HLB sucrose esters (L-195, S170) on the isothermal crystallization of coconut oil was investigated by differential scanning calorimetry. The fundamental crystallization parameters, such as induction time of nucleation and crystallization rate, were obtained by using the Gompertz equat...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2010.03.005

    authors: Chaleepa K,Szepes A,Ulrich J

    更新日期:2010-05-01 00:00:00

  • Effect of the different supramolecular organization on the uptake and metabolization of exogenous GM1 ganglioside by human fibroblasts.

    abstract::In this report we have investigated the differences in the uptake and metabolization of exogenous GM1 by human fibroblasts, as a function of its supramolecular organization in solution. For this we used a tritium labelled GM1, given alone or inserted in dispersions of phosphatidylcholine (PC) or sulphatide. The additi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(90)90080-b

    authors: Giglioni A,Chigorno V,Pitto M,Valsecchi M,Palestini P,Ghidoni R

    更新日期:1990-08-01 00:00:00

  • The phase transition behavior of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) model membrane influenced by 2,4-dichlorophenol--an FT-Raman spectroscopy study.

    abstract::The effect of 2,4-dichlorophenol (DCP) on the structures and phase transitions of fully hydrated 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) liposomes was studied using FT-Raman spectroscopy. Whereas the Raman frequency shifts of the most frequently investigated bands of C-C and C-H stretching regions only indi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2005.11.005

    authors: Csiszár A,Koglin E,Meier RJ,Klumpp E

    更新日期:2006-02-01 00:00:00

  • Synthesis and some properties of constrained short-chain phosphatidylcholine analogues: (+)- and (-)-(1,3/2)-1-O-(phosphocholine)2,3-O- dihexanoylcyclopentane-1,2,3-triol.

    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

    authors: Barlow PN,Vidal JC,Lister MD,Hancock AJ,Sigler PB

    更新日期:1988-03-01 00:00:00

  • The effect of non-deuterated and deuterated isopropyl myristate on the thermodynamical and structural behavior of a 2D Stratum Corneum model with Ceramide [AP].

    abstract::Isopropyl myristate (IPM) is a widely used penetration enhancer in pharmaceutical formulations, however, its mechanism of action on a molecular scale is still not completely understood. Previous work using a quaternary Stratum Corneum (SC) lipid model in bulk suggested the incorporation of isopropyl myristate into the...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2017.02.002

    authors: Oliveira JS,Lange S,Dobner B,Brezesinski G

    更新日期:2017-04-01 00:00:00

  • 1-O-benzyl-2-O-methyl-rac-glycerol: a key intermediate for synthesis of ether glycerolipids.

    abstract::A new scheme for synthesis of saturated 1-O-alkyl-2-O-methyl-rac-glycerolipids is described. The reductive cleavage of 2-O-methyl-1,3-O,O-benzylideneglycerol with BH3.THF complex leads to 1-O-benzyl-2-O-methyl-rac-glycerol, which is a key in intermediate for the facile preparation of 1-O-alkyl-2-O-methyl-rac-glycerol ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(91)90026-8

    authors: Pinchuk AN,Mitsner BI,Shvets VI

    更新日期:1991-10-01 00:00:00

  • Does cholesterol discriminate between sphingomyelin and phosphatidylcholine in mixed monolayers containing both phospholipids?

    abstract::The objective of this work was to examine the interaction of cholesterol with both phosphatidylcholines, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and sphingomyelins, N-oleoyl-D-sphingomyelin (O-SPM) or N-palmitoyl-D-sphingomyelin (P-SPM), in monolay...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(96)02535-2

    authors: Mattjus P,Slotte JP

    更新日期:1996-06-17 00:00:00

  • The role of the ganglioside lipid moiety in the process of ganglioside-cell interactions.

    abstract::The role of the ceramide moiety of gangliosides, together with the deriving aggregative properties of ganglioside in solution, in the process of ganglioside-cell interactions was studied. The natural GM1(stearoyl) and the synthetic GM1(acetyl), containing the stearoyl and acetyl groups as the acyl moiety, respectively...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(92)90048-t

    authors: Bassi R,Sonnino S

    更新日期:1992-07-01 00:00:00

  • Arrangement of lipid and protein in human serum high density lipoproteins: a proposed model.

    abstract::Based on size and compositional data, models for the two major density subclasses of human serum high density lipoproteins have been developed. Descriptions of both the surface structure of the high density lipoproteins and the structure of their apolar core regions are integral parts of these models. The surface is d...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(75)90054-7

    authors: Verdery RB,Nichols AV

    更新日期:1975-04-01 00:00:00

  • The effect of dolichol on the permeability properties of phosphatidylcholine bilayers.

    abstract::The permeability of liposomes to water, glucose, Ca2+ and alkaline cations was monitored by recording the change in absorbance at 450 nm using a rapid reaction stopped-flow spectrophotometer. Liposomes were prepared with egg phosphatidylcholine and concentrations of dolichol ranging from 0.1% to 9% (w/w). Net permeabi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(85)90028-3

    authors: Boscoboinik DO,Feliz M,Disalvo EA,Belocopitow E

    更新日期:1985-11-01 00:00:00

  • Involvement of sphingomyelinases in TNF signaling pathways.

    abstract::Sphingomyelin (N-acylsphingosin-1-phosphorylcholine) is a phospholipid preferentially found in the plasma membrane of mammalian cells. Signaling through the sphingomyelin pathway is associated with generation of ceramide, which acts as a second messenger in activating a variety of cellular functions. Ceramide belongs ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/s0009-3084(99)00084-5

    authors: Krönke M

    更新日期:1999-11-01 00:00:00

  • Polymerizable phospholipids with lipoic acid as head group: synthesis and phase properties.

    abstract::Lipoic acid-substituted phospholipids were synthesized from phosphatidyl cholines by exchanging the choline residue with a glycol group using phospholipase D, forming phosphatidylglycols, and coupling of lipoic acid (1,2-dithiolane-3-pentanoic acid) to the residual glycol hydroxyl group by esterification. The thermotr...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(93)90032-x

    authors: Pax H,Blume A

    更新日期:1993-11-01 00:00:00

  • Effect of lipoprotein(a) on lipid metabolism of cultured human intimal aortic cells.

    abstract::The effect of Lp(a) on lipid metabolism in cells cultured from unaffected human aortic intima has been investigated. Lp(a) isolated from the blood of healthy subjects failed to alter intracellular neutral lipid content. On the other hand, Lp(a) obtained from coronary atherosclerosis patients induced a 1.5- to 2-5-fold...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90135-x

    authors: Tertov VV,Orekhov AN

    更新日期:1994-01-01 00:00:00

  • Synthesis and characterization of long-chain 1,2-dioxo compounds.

    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

    authors: Knothe G

    更新日期:2002-05-01 00:00:00

  • Anchoring mechanisms of membrane-associated M13 major coat protein.

    abstract::Bacteriophage M13 major coat protein is extensively used as a biophysical, biochemical, and molecular biology reference system for studying membrane proteins. The protein has several elements that control its position and orientation in a lipid bilayer. The N-terminus is dominated by the presence of negatively charged...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2006.02.023

    authors: Stopar D,Spruijt RB,Hemminga MA

    更新日期:2006-06-01 00:00:00

  • New 20-hydroxycholesterol-like compounds with fluorescent NBD or alkyne labels: Synthesis, in silico interactions with proteins and uptake by yeast cells.

    abstract::20-hydroxycholesterol is a signaling oxysterol with immunomodulating functions and, thus, structural analogues with reporter capabilities could be useful for studying and modulating the cellular processes concerned. We have synthesized three new 20-hydroxycholesterol-like pregn-5-en-3β-ol derivatives with fluorescent ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2019.104850

    authors: Faletrov YV,Efimova VS,Horetski MS,Tugaeva KV,Frolova NS,Lin Q,Isaeva LV,Rubtsov MA,Sluchanko NN,Novikova LA,Shkumatov VM

    更新日期:2020-03-01 00:00:00

  • Interaction between phospholipids and monovalent cations studied by a new thin-layer chromatographic method.

    abstract::The interaction of monovalent cations and membrane phospholipids has a great theoretical and practical importance. Because of the very low differences between the binding forces of monovalent cations to phospholipids, the methods applied up till now did not succeed in completely elucidating this interaction. We develo...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(83)90062-2

    authors: Cserháti T,Szögyi M

    更新日期:1983-12-01 00:00:00

  • Swelling of intercellular lipid lamellar structure with short repeat distance in hairless mouse stratum corneum as studied by X-ray diffraction.

    abstract::Lamellar structures of intercellular lipids in stratum corneum of hairless mouse were studied at various water contents by small-angle X-ray diffraction. At room temperature there are at least two lamellar structures, long and short lamellar structures, with repeat distances of 13.6 and around 6 nm, respectively. The ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(02)00126-3

    authors: Ohta N,Ban S,Tanaka H,Nakata S,Hatta I

    更新日期:2003-03-01 00:00:00

  • Voltage-dependent behaviour of dolichyl phosphate-phosphatidylcholine bilayer lipid membranes.

    abstract::The current-voltage steady-state characteristics, cyclic voltammograms and capacitance-voltage steady-state relationships of bilayer lipid membranes made from dioleoylphosphatidylcholine or its mixtures with dolichyl-12 phosphate have been studied. Sustained fluctuations of the capacitance of dolichyl phosphate modifi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(90)90158-n

    authors: Janas T,Kuczera J,Chojnacki T

    更新日期:1990-01-01 00:00:00

  • Cholesterol-induced suppression of membrane elastic fluctuations at the atomistic level.

    abstract::Applications of solid-state NMR spectroscopy for investigating the influences of lipid-cholesterol interactions on membrane fluctuations are reviewed in this paper. Emphasis is placed on understanding the energy landscapes and fluctuations at an emergent atomistic level. Solid-state (2)H NMR spectroscopy directly meas...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2016.05.001

    authors: Molugu TR,Brown MF

    更新日期:2016-09-01 00:00:00

  • Ether lipids in biomembranes.

    abstract::Plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) and to a lesser extent the 1-O-alkyl analogs are ubiquitous and in some cases major constituents of mammalian cellular membranes and of anaerobic bacteria. In archaebacteria polar lipids of the cell envelope are either diphytanylglycerolipids or bipolar macrocyc...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/0009-3084(94)90054-x

    authors: Paltauf F

    更新日期:1994-12-01 00:00:00

  • Further studies on the inhibition of sterol biosynthesis in animal cells by 15-oxygenated sterols.

    abstract::The chemical syntheses of a number of C27 15-oxygenated sterols and their derivatives have been pursued to permit evaluation of their activity in the inhibition of sterol biosynthesis in animal cells in culture. Described herein are chemical syntheses of 3 alpha-benzoyloxy-5 alpha-cholest-8(14)-en-15-one, 5 alpha-chol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(79)90111-7

    authors: Schroepfer GJ Jr,Parish EJ,Kandutsch AA

    更新日期:1979-11-01 00:00:00

  • delta 5,7,9(11)-Cholestatrien-3 beta-ol: a fluorescent cholesterol analogue.

    abstract::Structural analysis, a purification scheme and stability information on a fluorescent cholesterol analogue, which has been used as a probe in several model and biological systems, are presented. The proposed structure for the fluorophore, cholestatrien-3 beta-ol, closely resembles that of cholesterol. However, problem...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(84)90086-0

    authors: Fischer RT,Stephenson FA,Shafiee A,Schroeder F

    更新日期:1984-11-01 00:00:00

  • Inverted micellar intermediates and the transitions between lamellar, cubic, and inverted hexagonal amphiphile phases. III. Isotropic and inverted cubic state formation via intermediates in transitions between L alpha and HII phases.

    abstract::Inverted cubic and isotropic phases have been observed in phospholipid and glycolipid systems. These phases exhibit characteristic morphologies in freeze-fracture electron micrographs, isotropic 31P-NMR resonances and (in some cases) cubic X-ray diffraction patterns. It is proposed here that these phases may form from...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(86)90087-3

    authors: Siegel DP

    更新日期:1986-12-31 00:00:00