Abstract：
:A new series of analogs of triglycerides has been synthesized, in which the glycerol moiety is replaced by each of the three isomeric cyclopentanetriols. For each of the isomeric cyclopentane-1,2,3-triols (1,2,3/0; DL-1,2/3; and 1,3/2), the tris-homoacyl derivatives of octanoic, decanoic, lauric, myristic, palmitic, stearic, and dihydrosterculic acids were prepared by treatment of the respective triols with the appropriate acyl chloride in pyridine. The dihydrosterculates were prepared by fusing the triols with a mixture of the acyl anhydride and the corresponding potassium salt. It is proposed that because of restricted rotation of the carbon-carbon bonds the cyclopentanoid compounds are analogs of specific rotamers of triglycerides. Infrared spectra (KBr discs) obtained at room temperature show differences in crystal structure from series to series. A band near 720 cm-minus 1 (CH2 rock) is doubled in the 1,2,3/0 and 1,2/3 series and is single in the 1,3/2 series and the triglycerides. In each spectrum with a doublet at 720 cm-minus 1, a band near 1470 cm-minus 1 (CH2 bend) is doubled also. A strong band at 890 cm-minus 1 present in the triglyceride spectra is weak or missing from the spectra of the analogs. A band at 1418 cm-minus 1 (bending of CH2 adjacent to C equal to 0) present in the triglyceride spectra is demonstrable only in the 1,2,3/0 derivatives in comparison with the other three series. In all series the dihydrosterculates show a decrease in apparent polarity, relative to the stearates, significantly greater than expected from the introduction of an additional carbon atom. The potential utility of the analogs as probes of the effects of conformation on the physical properties and enzymatic susceptibility of glycerides is discussed.
journal_name
J Lipid Resjournal_title
Journal of lipid researchauthors
Hancock AJ,Greenwald SM,Sable HZkeywords:
subject
Has Abstractpub_date
1975-07-01 00:00:00pages
300-7issue
4eissn
0022-2275issn
1539-7262journal_volume
16pub_type
杂志文章abstract：:We have determined the effect of the side chain on the uptake of sterols from micellar solutions by isolated rat jejunal villus cells, brush border membranes, and erythrocytes. From an equimolar mixture of 7-dehydrosterols, the uptake decreased with an increasing number of carbon atoms at C24 of the sterol side chain ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1983-05-01 00:00:00
abstract：:Phytanic acid (3,7,11,15-tetramethylhexadecanoic acid) is a branched-chain fatty acid derived from dietary sources and broken down in the peroxisome to pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) via alpha-oxidation. Pristanic acid then undergoes beta-oxidation in peroxisomes. Phytanic acid naturally occu...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：2002-03-01 00:00:00
abstract：:Steroids are primarily present in human fluids in their sulfated forms. Profiling of these compounds is important from both diagnostic and physiological points of view. Here, we present a novel method for the quantification of 11 intact steroid sulfates in human serum by LC-MS/MS. The compounds analyzed in our method,...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.D061499
更新日期：2015-09-01 00:00:00
abstract：:We have defined the lipid composition of copper-oxidized LDL (Cu-oxLDL) and a macrophage-foam cell model generated by the uptake of this modified lipoprotein. An HPLC method previously developed by our group for the measurement of lipid oxidation products of LDL was extended to permit the analysis of an array of 7-ket...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1996-02-01 00:00:00
abstract：:Native LDL (nLDL) increases expression of adhesion molecules on endothelial cells through induction of Ca(2+) mobilization. Ca(2+) mobilization is also involved in the induction of proinflammatory cytokines, important mediators involved in atherogenesis. The aim of the study was to evaluate the capacity of nLDL to aff...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.m100254-jlr200
更新日期：2002-07-01 00:00:00
abstract：:Ethanolamine phosphotransferase (EPT)1, also known as selenoprotein 1 (SELENOI), is an enzyme that transfers phosphoethanolamine from cytidine diphosphate-ethanolamine to lipid acceptors to produce ethanolamine glycerophospholipids, such as diacyl-linked phosphatidylethanolamine (PE) and ether-linked plasmalogen [1-al...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.P081620
更新日期：2018-06-01 00:00:00
abstract：:Gangliosides and sulfatides (STs) are acidic glycosphingolipids (GSLs) that have one or more sialic acids or sulfate substituents, in addition to neutral sugars, attached to the C-1 hydroxyl group of the ceramide long chain base. TLC is a widely employed and convenient technique for separation and characterization of ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.D046128
更新日期：2014-04-01 00:00:00
abstract：:ATP-citrate lyase (ACL) is a key lipogenic enzyme that converts citrate in the cytoplasm to acetyl-CoA, the initial precursor that yields malonyl-CoA for fatty acid biosynthesis. As cytosolic citrate is derived from the tricarboxylic acid cycle in the mitochondrion, ACL catalyzes a critical reaction linking cellular g...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M003335
更新日期：2010-09-01 00:00:00
abstract：:The isolated perfused mouse liver was utilized to evaluate the relative contribution of various molecules believed to participate in the removal of chylomicron remnants by the liver. Sixty percent of asialofetuin was removed from the perfusate per pass; bovine serum albumin was not removed. Normal mouse livers removed...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1999-10-01 00:00:00
abstract：:Using a radiometric assay with glycochenodeoxycholic acid as substrate, bile acid:3'-phosphoadenosine-5'-phosphosulfate sulfotransferase activity was found in 105,000 g supernatant fractions of liver, proximal intestine, and adrenal gland homogenates from adult hamsters. Optimum conditions for measurement of the hepat...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1979-11-01 00:00:00
abstract：:Autophagy is a catabolic process involved in maintaining energy and organelle homeostasis. The relationship between obesity and the regulation of autophagy is cell type specific. Despite adverse consequences of obesity on cardiac structure and function, the contribution of altered cardiac autophagy in response to fatt...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M055152
更新日期：2015-03-01 00:00:00
abstract：:ABCG1 and ABCG4 are highly homologous members of the ATP binding cassette (ABC) transporter family that regulate cellular cholesterol homeostasis. In adult mice, ABCG1 is known to be expressed in numerous cell types and tissues, whereas ABCG4 expression is limited to the central nervous system (CNS). Here, we show sig...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/M900250-JLR200
更新日期：2010-01-01 00:00:00
abstract：:Epoxyeicosatrienoic acids were isolated and purified from female rabbit kidneys. They were identified as a group, prior to resolution, by packed column gas-liquid chromatography-mass spectroscopic techniques as their methyl esters as well as their trimethylsilyl bromohydrin methyl esters. Initial capillary gas-liquid ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1987-07-01 00:00:00
abstract：:Adipogenic differentiation is a highly regulated process that is necessary for metabolic homeostasis and nutrient sensing. The expression of PPARγ and the subsequent activation of adipogenic genes is critical for the process. In this study, we identified lanthionine synthetase C-like protein 2 (LanCL2) as a positive r...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M085274
更新日期：2018-08-01 00:00:00
abstract：:Previous studies have shown that reduced levels of the adipocyte fatty acid binding protein (FABP)4 (AFABP/aP2), result in metabolic improvement including potentiated insulin sensitivity and attenuated atherosclerosis. Mechanistically, pharmacologic or genetic inhibition of FABP4 in macrophages upregulates UCP2, atten...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M074542
更新日期：2017-07-01 00:00:00
abstract：:Various properties of retinyl ester hydrolysis in the liver and the retinal pigment epithelium (RPE) have been studied, yet the relationship between the retinyl ester hydrolase (REH) activities in these tissues of the same species is not known. In the present study, REH activities in bovine liver and RPE microsomes we...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1996-09-01 00:00:00
abstract：:The cellular mechanisms responsible for the lipoprotein-mediated stimulation of bile acid synthesis in cultured rat hepatocytes were investigated. Adding 280 micrograms/ml of cholesterol in the form of human or rat low density lipoprotein (LDL) to the culture medium increased bile acid synthesis by 1.8- and 1.6-fold, ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1989-12-01 00:00:00
abstract：:Conjugated linoleic acid (CLA), a mixture of isomers of linoleic acid, has previously been shown to be able to decrease porcine subcutaneous (SC) adipose tissue levels while increasing the count of intramuscular (IM) adipose tissue in vivo. However, the underlying mechanisms through which it acts are poorly understood...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M600525-JLR200
更新日期：2007-08-01 00:00:00
abstract：:Electrospray ionization mass spectrometry has previously been used to probe qualitative changes in the phospholipid cardiolipin (CL), but it has rarely been used in a quantitative manner. We assessed changes in the amount of individual molecular species of cardiac CL present in a model of congestive heart failure usin...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.M500031-JLR200
更新日期：2005-06-01 00:00:00
abstract：:Severe endothelial abnormalities are a prominent feature in sepsis with cytokines such as tumor necrosis factor (TNF)alpha being implicated in the pathogenesis. As mimic to inflammation, human umbilical vascular endothelial cells (HUVEC) were incubated with TNFalpha for 22 h, in the absence or presence of the omega-6 ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：2002-06-01 00:00:00
abstract：:Membrane-protein interaction plays key roles in a wide variety of biological processes. Although various methods have been employed to measure membrane binding of soluble proteins, a robust high-throughput assay that is universally applicable to all proteins is lacking at present. Here we report a new fluorescence que...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：10.1194/jlr.D041376
更新日期：2013-12-01 00:00:00
abstract：:Binding of the medium-chain fatty acids (MCFA), octanoic (OCT) and decanoic (DEC) acid, to human serum albumin (HSA) has been studied by 13C NMR spectroscopy. NMR spectra at 35 degrees C showed an apparently homogeneous binding environment (a single, narrow resonance for the 13C-enriched carboxyl carbon) at different ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1994-03-01 00:00:00
abstract：:In Refsum disease, disorders of peroxisome biogenesis, and rhizomelic chondrodysplasia punctata, pathological accumulation of phytanic acid results from impaired alpha-oxidation of this branched-chain fatty acid. Previous studies from this laboratory indicated that activation of phytanic acid to its CoA derivative pre...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1996-11-01 00:00:00
abstract：:A simple procedure is described for preparing lyso-GM1, a GM1 derivative that lacks the fatty acid moiety, starting from GM1 ganglioside using a one-pot reaction. Ganglioside deacylation was carried out in KOH/propan-1-ol in the absence of oxygen. The yield of lyso-GM1 under optimal conditions (6 h, 90 degrees C, 0.2 ...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1992-08-01 00:00:00
abstract：:Fatty acid translocase (FAT/CD36) is a membrane protein putatively involved in the transmembrane transport of long-chain fatty acids. We tested the hypothesis that expression of this protein in H9c2, a rat heart cell line normally not expressing FAT, would increase cellular palmitate uptake. We were able to stably tra...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1998-10-01 00:00:00
abstract：:The selective and reversible adsorption of bovine low density lipoproteins (LDL) by heparin-Sepharose has been exploited as the critical step in a procedure for the preparative isolation of very low density lipoproteins (VLDL)/chylomicrons, LDL, and high density lipoproteins (HDL) from bovine plasma. Molecular size ex...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1985-06-01 00:00:00
abstract：:Serine palmitoyltransferase [EC 2.3.1.50] catalyzes the first unique reaction of sphingolipid biosynthesis. To determine whether or not different rat tissues are capable of initiating this pathway, its activity was determined for microsomes from rat liver, lung, brain, kidney, intestine, spleen, muscle, heart, pancrea...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1985-05-01 00:00:00
abstract：:A reproducible cell culture system is described that allows the study of adipose conversion in fibroblast-like cells isolated by collagenase digestion of epididymal and perirenal adipose tissue from male rats weighing 70-200 g. Adipose conversion as measured by lipid accumulation and increase in glycerophosphate dehyd...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1987-06-01 00:00:00
abstract：:The extent of oxidoreduction of the 3 alpha-, 7 alpha- and 12 alpha-hydroxyl groups in bile acids during the enterohepatic circulation in man was studied with the use of [3 beta-3H]-labeled deoxycholic acid and cholic acid, [7 beta-3H]-labeled cholic acid, and [12 beta-3H]-labeled deoxycholic acid and cholic acid. Eac...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1986-02-01 00:00:00
abstract：:Analytical isoelectric focusing (IEF) has been applied to the study of the apolipoprotein components of rat serum high density and very low density lipoproteins. The apolipoproteins were separated on 7.5% polyacrylamide gels containing 6.8% urea, with a pH gradient of 4-6. The middle molecular weight range apolipoprot...
journal_title：Journal of lipid research
pub_type： 杂志文章
doi：
更新日期：1977-01-01 00:00:00
