Abstract:
:Two new 6-hydroxylated bile acids, 3 beta, 6 alpha, 12 alpha- and 3 beta, 6 beta, 12 alpha-trihydroxy-5 beta-cholanoic acids, were synthesized from deoxycholic acid. In addition, their C-3 epimers, 3 alpha, 6 alpha, 12 alpha- and 3 alpha, 6 beta, 12 alpha-trihydroxy acids, were prepared by a new route. The principal reactions used were 1) 6 beta-hydroxylation of 3-methoxy-3,5-dienes with m-chloroperbenzoic acid in aqueous dioxane; 2) catalytic hydrogenation of the resulting 6 beta-hydroxy-3-oxo-4-enes to the 6 beta-hydroxy-3-oxo-5 beta compounds with palladium on calcium carbonate catalyst in ethanol; and 3) stereoselective reduction of appropriate 3-oxo derivatives with potassium tri-sec-butylborohydride and tert-butylamine-borane complex. The thin-layer chromatographic, gas-liquid chromatographic, and high performance liquid chromatographic mobilities, and 1H- and 13C-nuclear magnetic resonance spectroscopic data of the four stereoisomers are presented. With this work all the 6-hydroxylated derivatives of lithocholic, deoxycholic, chenodeoxycholic, ursodeoxycholic, and cholic acids in the 5 beta series are now known and have been synthesized.
journal_name
J Lipid Resjournal_title
Journal of lipid researchauthors
Iida T,Tamaru T,Chang FC,Goto J,Nambara Tsubject
Has Abstractpub_date
1991-04-01 00:00:00pages
649-58issue
4eissn
0022-2275issn
1539-7262journal_volume
32pub_type
杂志文章abstract::We have developed the technique of rapid (< 2 h) centrifugal ultrafiltration to measure the inter-mixed micellar/vesicular (non-lecithin-associated) bile salt (BS) concentrations (IMC) of individual BS in model biles. This methodology uses a centrifugal concentrator with a reinforced membrane, through which a small fr...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1993-07-01 00:00:00
abstract::To determine the extent and microanatomical distribution of extramyocellular adipocytes associated with skeletal muscle, histological, biochemical, nuclear magnetic resonance proton spectroscopic and microcomputed tomography techniques were employed to analyze skeletal muscle samples from lean and obese Sprague-Dawley...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:2001-07-01 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::To examine the validity of the deuterium (D) incorporation technique for measurement of human cholesterol synthesis rates, D uptake from D2O into cholesterol was compared to sterol balance in 13 subjects each under three controlled diet settings. Subjects (age 62 +/- 3.6 yr, body weight 74 +/- 4.0 kg, BMI 27 +/- 1.4) ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1998-05-01 00:00:00
abstract::Changes in chromatin structure regulate gene expression and genome maintenance. Molecules that bind to the nucleosome, the complex of DNA and histone proteins, are key modulators of chromatin structure. Previous work indicated that cholesterol, a ubiquitous cellular lipid, may bind to chromatin in vivo, suggesting a p...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M074997
更新日期:2017-05-01 00:00:00
abstract::The human retina is well-known to have unique lipid profiles enriched in long-chain polyunsaturated fatty acids (LC-PUFAs) and very long-chain polyunsaturated fatty acids (VLC-PUFAs) that appear to promote normal retinal structure and function, but the influence of diet on retinal lipid profiles in health and disease ...
journal_title:Journal of lipid research
pub_type: 临床试验,杂志文章
doi:10.1194/jlr.P065540
更新日期:2016-03-01 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::Normal human plasma HDL was applied to a column of heparin-Sepharose in the presence of MnCl(2) and three fractions were obtained by stepwise elution with increasing NaCl concentrations: a non-retained fraction (NR, 78% of protein) and two retained fractions (R(1) and R(2), 18 and 2.5% of protein, respectively). Both ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1981-11-01 00:00:00
abstract::Apolipoprotein E2 (apoE2)-associated hyperlipidemia is characterized by a disturbed clearance of apoE2-enriched VLDL remnants. Because excess apoE2 inhibits LPL-mediated triglyceride (TG) hydrolysis in vitro, we investigated whether direct or indirect stimulation of LPL activity in vivo reduces the apoE2-associated hy...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M800009-JLR200
更新日期:2008-05-01 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::Serum triglyceride (TG) levels are increased in extremely obese individuals, indicating abnormalities in lipid metabolism and insulin resistance. We carried out a genome scan for serum TG in 320 nuclear families segregating extreme obesity and normal weight. Three hundred eighty-two Marshfield microsatellite markers (...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M400391-JLR200
更新日期:2005-03-01 00:00:00
abstract::Incubation of low density lipoprotein (LDL) with endothelial cells converts it to a form that is avidly degraded by macrophages via the acetyl LDL receptor. This modification has previously been shown to be accompanied by extensive breakdown of the major LDL protein (apoB-100) to smaller peptides. ApoB-100 is known to...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1987-12-01 00:00:00
abstract::The storage of lipids in the form of triglycerides (TGs) and the de novo synthesis (lipogenesis) of fatty acids from nonlipid precursors [de novo lipogenesis (DNL)] are important functions of adipose tissue (AT) that influence whole-body metabolism. Yet, few studies have reported in vivo estimates of adipose lipid kin...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.P082628
更新日期:2018-09-01 00:00:00
abstract::EPA and DHA are not biologically equivalent; however, their individual activity on B cells is unknown. We previously reported fish oil enhanced murine B-cell activity in obesity. To distinguish between the effects of EPA and DHA, we studied the ethyl esters of EPA and DHA on murine B-cell function as a function of tim...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M049809
更新日期:2014-07-01 00:00:00
abstract::Distinct isoforms of long-chain acyl-CoA synthetases (ACSLs) may partition fatty acids toward specific metabolic cellular pathways. For each of the five members of the rat ACSL family, we analyzed tissue mRNA distributions, and we correlated the mRNA, protein, and activity of ACSL1 and ACSL4 after fasting and refeedin...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M600150-JLR200
更新日期:2006-09-01 00:00:00
abstract::Alcohol consumption markedly increases the hepatic output of very low density lipoprotein (VLDL), whereas it decreases the resulting low density lipoprotein (LDL) levels and apolipoprotein B. As ethylation of apoB-lysine renders LDL immunogenic and accelerates their clearance, and as alcoholics develop antibodies agai...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1993-07-01 00:00:00
abstract::Acute respiratory distress syndrome (ARDS) is associated with a severe pro-inflammatory response; although decreased plasma cholesterol concentration has been linked to systemic inflammation, any association of phospholipid metabolic pathways with ARDS has not been characterized. Plasma phosphatidylcholine (PC), the m...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.P085050
更新日期:2018-06-01 00:00:00
abstract::Adipose tissue contains one of the largest reservoirs of cholesterol in the body. Adipocyte dysfunction in obesity is associated with intracellular cholesterol accumulation, and alterations in cholesterol homeostasis have been shown to alter glucose metabolism in cultured adipocytes. ABCA1 plays a major role in choles...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M045294
更新日期:2014-03-01 00:00:00
abstract::Thus far, liver, intestine, heart, and placenta have been shown to secrete apolipoprotein (apo)B-containing lipoproteins. In the present study, we first investigated lipoproteins in human follicular fluid (FF), surrounding developing oocytes within the ovary, as well as in corresponding plasma samples (n = 12). HDL ch...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M005181
更新日期:2010-08-01 00:00:00
abstract::The esterification of lysophospholipids contributes to phospholipid synthesis, remodeling, and scavenging. Acyl-CoA-dependent lysophospholipid acyltransferase activity with broad substrate use is mediated by Saccharomyces cerevisiae Lpt1p. We sought to identify Lpt1p active site amino acids besides the histidine conse...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M062141
更新日期:2015-11-01 00:00:00
abstract::Sphingolipids comprise a highly diverse and complex class of molecules that serve not only as structural components of membranes but also as signaling molecules. To understand the differential role of sphingolipids in a regulatory network, it is important to use specific and quantitative methods. We developed a novel ...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.D005322
更新日期:2010-07-01 00:00:00
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::Acyl-CoA:monoglyceride acyltransferase in microsomal preparations from the small intestine of the rat has been measured by means of continuous recording spectrophotometry. The reaction of 5,5'-dithiobis(2-nitrobenzoic acid) with CoA has been employed for this assay and optimal conditions for the reaction have been def...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1969-07-01 00:00:00
abstract::Effects of serum cholesterol on cholesterol content in the retina are currently unknown. It is also unclear how cholesterol levels are controlled in the retina. High-cholesterol diet and oral administrations of simvastatin were used to modulate serum cholesterol in mice. These treatments only modestly affected cholest...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M053439
更新日期:2015-01-01 00:00:00
abstract::Triacylglycerols (TG) are the major storage form of energy in eukaryotic organisms and are synthesized primarily by acyl CoA:1,2-diacylglycerol acyltransferase (DGAT) enzymes. In vitro DGAT activity has previously been quantified by measuring the incorporation of either radiolabeled fatty acyl CoA or diacylglycerol (D...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.D016626
更新日期:2011-09-01 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::Sebaceous glands are intriguing glands that are found throughout the human body except on the palms of the hands and soles of the feet. The true function of these glands has yet to be determined, but there are several theories, including antioxidant effects, antibacterial effects, and transport of pheromones. Sebaceou...
journal_title:Journal of lipid research
pub_type: 杂志文章,评审
doi:10.1194/jlr.R700015-JLR200
更新日期:2008-02-01 00:00:00
abstract::Multiple changes in HDL metabolism occur during infection and inflammation that could potentially impair the antiatherogenic functions of HDL. Scavenger receptor class B type I (SR-BI) promotes cholesterol efflux from peripheral cells and mediates selective uptake of cholesteryl ester into hepatocytes, thereby playing...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:2001-10-01 00:00:00
abstract::Triglyceride (TG) concentration is used as a marker of cardiometabolic risk. However, diurnal and possibly weekday variation exists in TG concentrations. The objective of this work was to investigate weekday variation in TG concentrations among 1.8 million blood samples drawn between 2008 and 2015 from patients in the...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:10.1194/jlr.M074062
更新日期:2017-06-01 00:00:00
abstract::In mammals, the apolipoprotein (apo) A-I gene is expressed predominantly in liver and intestine, while in avian species it is expressed in all tissues. Although liver and intestine are the major sites of chicken apoA-I mRNA synthesis, there are appreciable amounts of apoA-I mRNA in kidney, ovary/testes, brain, lung, s...
journal_title:Journal of lipid research
pub_type: 杂志文章
doi:
更新日期:1992-06-01 00:00:00