Abstract:
:Optically active 1- or 3-acyl-sn-glycerols were synthesized from 2,3- or 1,2-isopropylidene-sn-glycerols, respectively. The 2,3- or 1,2-isopropylidene-sn-glycerols were condensed with appropriate long saturated or unsaturated fatty acids and the resulting acyl isopropylidene compounds were treated with dimethylboronbromide at - 50 degrees C to give the title compounds. The ketal cleavage of acyl isopropylidene-sn-glycerols by dimethylboronbromide to produce the long 1- or 3-acyl-sn-glycerols was effective and gave good yields (70-90%). The reaction conditions were mild and there was no acyl migration, as shown by optical rotation of the monoacyl-sn-glycerols. The synthesis of 2,3-isopropylidene-sn-glycerol was improved to give an overall yield of 40% from L-arabinose. L-Arabinose was first converted to its 1,1'-diethylmercapto derivative and then condensed with 2-methoxypropene to yield 1,1'-diethyl-mercapto-4,5-isopropylidene-L-arabinose. Oxidation of this compound with sodium periodate followed by reduction with sodium borohydride under alkaline conditions yielded 2,3-isopropylidene-sn-glycerol [alpha]22D = -14.90 degrees, neat (Lit. 8 [alpha]22D = -14.5 degrees, neat; 14 [alpha]25D = -10.8 degrees; methanol C, 16.9). The optical purity of isopropylidene-sn-glycerols was determined as benzoyl derivatives on a high performance liquid chromatographic column packed with a chiral stationary phase.
journal_name
J Lipid Resjournal_title
Journal of lipid researchauthors
Kodali DRsubject
Has Abstractpub_date
1987-04-01 00:00:00pages
464-9issue
4eissn
0022-2275issn
1539-7262journal_volume
28pub_type
杂志文章abstract::A novel metabolite of d-delta-tocopherol was isolated from the urine of rats given d-3,4-[3H2]-delta-tocopherol intravenously. The metabolite was collected from the urine of rats given d-delta-tocopherol in the same manner as that of the labeled compound. It was found that the metabolites consisted of sulfate conjugat...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1984-01-01 00:00:00
abstract::The activities of hepatic fatty acid oxidation enzymes in rats fed perilla oil rich in alpha-linolenic acid (alpha-18:3) were compared with those fed saturated fats or safflower oil (the mixture of safflower oil and olive oil, 94:8, w/w) containing the same amount of polyunsaturated fatty acids with perilla oil exclus...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1996-03-01 00:00:00
abstract::The relationship between the cholesterol 7 alpha-hydroxylase activity and the pool of free cholesterol in rat liver microsomes was studied under experimental conditions aimed to stimulate (biliary drainage, cholestyramine treatment, and lymphatic drainage) as well as inhibit (chenodeoxycholic acid treatment) bile acid...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1987-03-01 00:00:00
abstract::In mammals, the esterification of sterols by ACAT plays a critical role in eukaryotic lipid homeostasis. Using the predominant isoform of the yeast ACAT-related enzyme family, Are2p, as a model, we targeted phylogenetically conserved sequences for mutagenesis in order to identify functionally important motifs. Deletio...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:2001-08-01 00:00:00
abstract::The dynamics of human apoE metabolism were explored by examining the effects of alimentary lipemia and postheparin lipolysis on the plasma level and lipoprotein distribution of apoE. In the studies of alimentary lipemia, fasting and postprandial plasma samples were obtained from five normal adult males, each of whom d...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1982-12-01 00:00:00
abstract::The chemical composition and metabolism of lipoproteins in a population of Benedictine nuns were studied after 5-month periods during which the predominant dietary fats were sunflower oil, peanut oil, palm oil, or milk fats (butter and cream). The population was divided into three groups. The control group (C) include...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1984-05-01 00:00:00
abstract::Selenocysteine (Sec) insertion sequence-binding protein 2 (SBP2) is essential for the biosynthesis of Sec-containing proteins, termed selenoproteins. Subjects with mutations in the SBP2 gene have decreased levels of several selenoproteins, resulting in a complex phenotype. Selenoproteins play a significant role in ant...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M059105
更新日期:2015-11-01 00:00:00
abstract::Lipids were extracted from alfalfa samples collected at intervals over the growing season and were fractionated to yield pure sulfolipid. In the sulfolipid and in a phospholipid fraction the major fatty acids were palmitic, linolenic, and linoleic, of which the palmitic acid increased in proportion during the season w...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1967-07-01 00:00:00
abstract::ZR-78 and ZR-82 cells are two peroxisomal-deficient Chinese hamster ovary (CHO) cell mutants. These cells lack normal peroxisomes and show reduced levels of plasmalogen synthesis and other peroxisomal functions attributed to the deficiency of peroxisomal matrix enzymes. As we have recently identified two HMG-CoA reduc...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1998-09-01 00:00:00
abstract::A method is described for determining the long-chain base content of glycosphingolipids after acid hydrolysis, using the new reagent fluorescamine. The reaction is sensitive and can be used to characterize or measure glycosphingolipids in quantities routinely separated by thin-layer chromatography. ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1974-03-01 00:00:00
abstract::A new method for the purification of apolipoprotein H by affinity chromatography followed by continuous-elution electrophoresis is described. It is both simpler and less complicated than the chromatographic and electrophoretic methods usually used. In addition, apolipoprotein H is isolated in a pure, structurally uncl...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1996-04-01 00:00:00
abstract::Previously, our laboratory demonstrated that ceramide-1-phosphate (C1P) specifically activated group IVA cytosolic phospholipase A(2) (cPLA(2)alpha) in vitro. In this study, we investigated the chain length specificity of this interaction. C1P with an acyl-chain of >or=6 carbons efficiently activated cPLA(2)alpha in v...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M800367-JLR200
更新日期:2009-10-01 00:00:00
abstract::Sequence homology indicates the existence of three human cytosolic acyl protein thioesterases, including APT1 that is known to depalmitoylate H- and N-Ras. One of them is the lysophospholipase-like 1 (LYPLAL1) protein that on the one hand is predicted to be closely related to APT1 but on the other hand might also func...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M019851
更新日期:2012-01-01 00:00:00
abstract::The vitamin D signal transduction system involves a series of cytochrome P450-containing sterol hydroxylases to generate and degrade the active hormone, 1α,25-dihydroxyvitamin D3, which serves as a ligand for the vitamin D receptor-mediated transcriptional gene expression described in companion articles in this review...
journal_title:Journal of lipid research
pub_type: 杂志文章,评审
doi:10.1194/jlr.R031534
更新日期:2014-01-01 00:00:00
abstract::We describe a method for estimating the total activity of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase (EC 1.1.1.34) in the small intestine of rats. An homogenate of the whole small intestine is prepared rapidly and assayed directly to maximize the yield of enzyme and to minimize opportunity for uncontrolled cha...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1982-02-01 00:00:00
abstract::The effect of a single glucose feeding upon the net inflow and outflow transport of plasma free fatty acids (FFA) has been studied in 75 unanesthetized rats. The animals were fasted for 22 +/- 2 hr; then 50 rats were refed 2 ml of 50% glucose by gastric intubation. At 0, 10-15, and 30-35 min after glucose refeeding, t...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1969-01-01 00:00:00
abstract::Unesterified cholesterol is an essential structural component of the plasma membrane of every cell. During evolution, this membrane came to play an additional, highly specialized role in the central nervous system (CNS) as the major architectural component of compact myelin. As a consequence, in the human the mean con...
journal_title:Journal of lipid research
pub_type: 杂志文章,评审
doi:10.1194/jlr.R400004-JLR200
更新日期:2004-08-01 00:00:00
abstract::Cardiac triacylglycerol (TG) catabolism critically depends on the TG hydrolytic activity of adipose triglyceride lipase (ATGL). Perilipin 5 (Plin5) is expressed in cardiac muscle (CM) and has been shown to interact with ATGL and its coactivator comparative gene identification-58 (CGI-58). Furthermore, ectopic Plin5 ex...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M034710
更新日期:2013-04-01 00:00:00
abstract::ABCB4, which is specifically expressed on the canalicular membrane of hepatocytes, exports phosphatidylcholine (PC) into bile. Because SM depletion increases cellular PC content and stimulates PC and cholesterol efflux by ABCA1, a key transporter involved in generation of HDL, we predicted that SM depletion also stimu...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M056622
更新日期:2015-03-01 00:00:00
abstract::Our previous studies have demonstrated the activity of oncostatin M (OM) in stimulating the transcription of the human LDL receptor (LDLR) gene in HepG2 cells through a sterol-independent regulatory mechanism. The current studies were designed to determine whether this in vitro property of OM could be recapitulated in...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M400425-JLR200
更新日期:2005-06-01 00:00:00
abstract::Lipids secreted form the bovine meibomian glands were assigned to following classes: cholesteryl esters (A) (fatty acyl chain lengths from 15 to 27 carbon atoms), 41%; wax esters, 29%; triacylglycerols, 10%; and cholesteryl ester (B) (fatty acyl chain lengths from 14 to 18 carbons), 15%. The remaining 5% consisted of ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1976-07-01 00:00:00
abstract::We report on the effect of human apolipoprotein (apo) A-II transgene expression on atherosclerosis susceptibility in two transgenic lines (25.3 and 11.1) whose plasma human apoA-II concentrations (approximately 23 and 96 mg/dl, respectively) span the normal range in humans. After 9 months of an atherogenic diet, 25.3 ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1998-02-01 00:00:00
abstract::The origin of the cholesterol needed by the cornea for growth and cell turnover was addressed by comparing absolute rates of sterol synthesis with rates of sterol accumulation during early development of the rabbit. Linearity of incorporation of 3H2O and [14C]mevalonate into digitonin-precipitable sterols with time of...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1989-07-01 00:00:00
abstract::We have studied the synthesis, modification, and secretion of rat apoE in primary cultures of neonatal aortic smooth muscle cells and adult rat hepatocytes. The cultures were pulsed with [35S]methionine and the intracellular and secreted apoE were immunoprecipitated and analyzed by two-dimensional isoelectric focusing...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1988-07-01 00:00:00
abstract::The extent and site(s) of inhibition of cholesterol absorption by plant sterols, sitosterol and fucosterol, were studied in rats. The intragastric administration of a single emulsified lipid meal containing 25 mg [3H]cholesterol and 25 mg of either sitosterol or fucosterol inhibited the lymphatic absorption of cholest...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1988-12-01 00:00:00
abstract::The infrared (IR) and nuclear magnetic resonance (NMR) spectra of eight Delta(24)-steroids and nine C-24 saturated steroids were examined. NMR spectra allow unambiguous assignment of the biologically important Delta(24)-bond; introduction of a Delta(24)-bond causes the appearance of peaks at Delta 1.60 and 1.68 associ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1968-01-01 00:00:00
abstract::Pulmonary surfactant is a lipid:protein complex containing dipalmitoyl-phosphatidylcholine (DPPC) as the major component. Recent studies indicate adsorbed surfactant films consist of a surface monolayer and a monolayer-associated reservoir. It has been hypothesized that the monolayer and its functionally contiguous re...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M200380-JLR200
更新日期:2003-03-01 00:00:00
abstract::Glycolipids were isolated from the brain of a patient with a myoclonic variant of late infantile amaurotic idiocy. There was an abnormal glycolipid pattern in gray and white matter. The observed high concentration of gangliosides was due to a uniform accumulation of all four major gangliosides and was not limited to o...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1970-05-01 00:00:00
abstract::Hepatocytes and hepatic stellate cells play important roles in retinoid storage and metabolism. Hepatocytes process postprandial retinyl esters and are responsible for secretion of retinol bound to retinol-binding protein (RBP) to maintain plasma retinol levels. Stellate cells are the body's major cellular storage sit...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:2000-06-01 00:00:00
abstract::This study examined the in vivo relationship between expression of the HDL receptor scavenger receptor class B (SR-BI) and corresponding structural changes in the rat adrenocortical cell microvillar compartment. Using hormonal stimulation and withdrawal protocols, we were able to manipulate adrenal SR-BI levels and ca...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:2002-06-01 00:00:00