Abstract:
:Fatty acid alpha-hydroxylase from Sphingomonas paucimobilis is an unusual cytochrome P450 enzyme that hydroxylates the alpha-carbon of fatty acids in the presence of H2O2. Herein, we describe our investigation concerning the utilization of various substrates and the optical configuration of the alpha-hydroxyl product using a recombinant form of this enzyme. This enzyme can metabolize saturated fatty acids with carbon chain lengths of more than 10. The Km value for pentadecanoic acid (C15) was the smallest among the saturated fatty acids tested (C10-C18) and that for myristic acid (C14) showed similar enzyme kinetics to those seen for C15. As shorter or longer carbon chain lengths were used, Km values increased. The turnover numbers for fatty acids with carbon chain lengths of more than 11 were of the same order of magnitude (10(3) min(-1)), but the turnover number for undecanoic acid (C11) was less. Dicarboxylic fatty acids and methyl myristate were not metabolized, but monomethyl hexadecanedioate and omega-hydroxypalmitic acid were metabolized, though with lower turnover values. Arachidonic acid was a good substrate, comparable to C14 or C15. The metabolite of arachidonic acid was only alpha-hydroxyarachidonic acid. Alkanes, fatty alcohols, and fatty aldehydes were not utilized as substrates. Analysis of the optical configurations of the alpha-hydroxylated products demonstrated that the products were S-enantiomers (more than 98% enantiomerically pure). These results suggested that this P450 enzyme is strictly responsible for fatty acids and catalyzes highly stereo- and regioselective hydroxylation, where structure of omega-carbon and carboxyl carbon as well as carbon chain length of fatty acids are important for substrate-enzyme interaction.
journal_name
Lipidsjournal_title
Lipidsauthors
Matsunaga I,Sumimoto T,Ueda A,Kusunose E,Ichihara Kdoi
10.1007/s11745-000-533-ysubject
Has Abstractpub_date
2000-04-01 00:00:00pages
365-71issue
4eissn
0024-4201issn
1558-9307journal_volume
35pub_type
杂志文章相关文献
LIPIDS文献大全abstract::The physiological role of long-chain fatty acyl-CoA is thought to be primarily in intermediary metabolism of fatty acids. However, recent data show that nM to microM levels of these lipophilic molecules are potent regulators of cell functions in vitro. Although long-chain fatty acyl-CoA are present at several hundred ...
journal_title:Lipids
pub_type: 杂志文章,评审
doi:10.1007/BF02522684
更新日期:1996-09-01 00:00:00
abstract::Naturally occurring tetraalkylsubstituted furan fatty acids (F-acids) were tested as potential substrates for soybean lipoxygenase-1. For this purpose, F-acid methyl ester and phosphatidylcholines containing F-acids at the sn-2 position of the glycerol residue were incubated with the enzyme. Oxidation of F-acids only ...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02537308
更新日期:1994-06-01 00:00:00
abstract::Lysophosphatidic acid (lysoPtdOH), a lysophospholipid mediator, exerts diverse physiological effects, including angiogenesis, through its specific G-protein-coupled receptors. Previously, we showed that unfertilized hen egg white contains polyunsaturated fatty acid-rich lysoPtdOH and lysophospholipase D (lysoPLD). Her...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-013-3765-7
更新日期:2013-03-01 00:00:00
abstract::Bile acids solubilize proteins from liver plasma membrane both in vivo and in vitro. The ability to solubilize the proteins is dependent on the species of bile acid. In this paper, the effect of phospholipid on the solubilization of a membrane-bound enzyme by bile acids was investigated in vitro. Taurocholate (TC) and...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02534873
更新日期:1987-01-01 00:00:00
abstract::We have investigated the regulation of cholesterol synthesis in isolated human small intestine epithelial cells (enterocytes). It was established that the amount of cholesterol synthesized increased linearly with the incubation time and the number of cells in the incubation mixture; the synthesis was suppressed by 7-k...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02535408
更新日期:1986-12-01 00:00:00
abstract::Acetate supplementation increases plasma acetate, brain acetyl-CoA, histone acetylation, phosphocreatine levels, and is anti-inflammatory in models of neuroinflammation and neuroborreliosis. Although radiolabeled acetate is incorporated into the cellular lipid pools, the effect that acetate supplementation has on lipi...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-014-3911-x
更新日期:2014-07-01 00:00:00
abstract::The purpose of these experiments was to study the uptake and metabolism of exogenous triglyceride in the isolated perfused rabbit heart. When infused into the rabbit heart, [9,10-3H(N)]triolein was retained and incorporated into a lipid fraction that had the chromatographic mobility of authentic triolein. Incorporatio...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02538094
更新日期:1990-08-01 00:00:00
abstract::In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34-78%...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1002/lipd.12213
更新日期:2020-03-01 00:00:00
abstract::Isolated perfused rat lungs liberated fatty acids at a rate of 15 mumol/hr during perfusion of triglyceride-rich medium through the pulmonary vascular bed. About 80% of this activity seemed to result from lipoprotein lipase and 20% to hormone-sensitive lipase. Ventilation of the lungs with cigarette smoke instead of a...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02534227
更新日期:1980-07-01 00:00:00
abstract::The objective of the present studies was to examine the effect of dietary fat on the lipid composition of rat colonocytes and their utilization of short-chain fatty acids (SCFA). Rats were fed 14% beef fat, fish oil or safflower oil plus 2% corn oil in a semi-synthetic base diet for 4 wk. Colonocytes were isolated and...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02544340
更新日期:1990-06-01 00:00:00
abstract::Insulin and dietary fructose independently induce stearoyl-CoA desaturase 1 (SCD1) gene expression in diabetic mouse liver. In the present study, we again used diabetic mice and supplemented a high fructose diet with polyunsaturated fatty acids (PUFA) to determine the selective repression of SCD1 gene expression by di...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02637047
更新日期:1996-03-01 00:00:00
abstract::Acid cholesteryl ester hydrolase (CEH) activity was assayed in mononuclear cells of patients with symptomatic atherosclerosis (transient ischemic attacks, TIA) and in age-matched controls showing no evidence of atherosclerosis. The acid CEH level of TIA patients was significantly lower than that of controls (1074 +/- ...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02534317
更新日期:1980-12-01 00:00:00
abstract::Hydrolysis of cell envelope phospholipids was demonstrated in cells of both autolytic and nonautolytic strains of Neisseria gonorrhoeae that were labeled during growth in the presence of [3H] acetate. The label incorporated into the cellular phospholipids was located exclusively in the fatty acid acyl side chains. Lab...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02533897
更新日期:1979-08-01 00:00:00
abstract::Plasma and liver lipids were studied in male weanling rats fed diets containing moderate levels of fat (6% by weight) as sunflower oil (SF diet, rich in linoleic acid), salmon oil (SM diet, rich in long-chain n-3 fatty acids), or a blend of peanut and rapeseed oil (PR diet, rich in oleic acid). After nine weeks of fee...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02522983
更新日期:1996-08-01 00:00:00
abstract::The presence of leptin receptors in white adipose tissue (WAT) suggests a type of peripheral control during the development of obesity and other metabolic disorders. Both diet composition and exercise influence serum leptin; however, the effect of their combination on long-term WAT leptin metabolism is unknown. In thi...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-013-3854-7
更新日期:2014-01-01 00:00:00
abstract::A comparison of human adult and fetal adrenals with respect to their levels of glyceryl ether lipids and other lipid components is reported. Fetal glands contained significantly lower levels of alk-1-enyl phosphoglycerides and of cholesterol. Neutral glyceryl ether diesters, and ethanolamine and choline phosphoglyceri...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02533392
更新日期:1977-07-01 00:00:00
abstract::Mice exposed to cold rely upon brown adipose tissue (BAT)-mediated nonshivering thermogenesis to generate body heat using dietary glucose and lipids from the liver and white adipose tissue. In this report, we investigate how cold exposure affects the PI3 K/Akt signaling cascade and the expression of genes involved in ...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-010-3422-3
更新日期:2010-06-01 00:00:00
abstract::Administration of 2,2'''-([1-methyl-4, 4-diphenylbutylidene] bis(p-phenyl-eneoxy]) bistriethylamine oxalate (SQ 10,591) at 20 mg/Kg daily for 5 days to cholesterol-fed rabbits resulted in no change in aortic microsomal cholesterol esterification with a palmitoyl coenzyme A substrate or of aortic mitochondrial choleste...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02532164
更新日期:1975-02-01 00:00:00
abstract::Jasmonic acid (JA) is synthesized from linolenic acid (18:3n-3) by sequential action of 13-lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase. The fungus Lasiodiplodia theobromae can produce large amounts of JA and was recently reported to form the JA precursor 12-oxophytodienoic acid. The objective o...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-011-3622-5
更新日期:2012-01-01 00:00:00
abstract::The weight loss supplement conjugated linoleic acid (CLA) consists of an equal mixture of trans-10,cis-12 (10,12) and cis-9,trans-11 (9,11) isomers. However, high levels of mixed CLA isomers, or the 10,12 isomer, causes chronic inflammation, lipodystrophy, or insulin resistance. We previously demonstrated that 10,12 C...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-012-3711-0
更新日期:2012-11-01 00:00:00
abstract::Some 1,2- and 1,3-diacyl glycerols (with acyl groups as stearyl, oleyl, linoleyl, or stearolyl) were synthesized by conventional methods. The diacyl glycerols were esterified with 6-bromo-hexanoic acid to give the corresponding bromo-triacylglycerols (of the type AAB and ABA containing a bromo group at the distal part...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-001-0769-6
更新日期:2001-06-01 00:00:00
abstract::The effects of aging on the hepatic metabolism of cholesterol were studied in 1-, 6- and 24-month-old male Sprague-Dawley rats. Microsomal 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase activity, which regulates cholesterol biosynthesis, decreased from 835 +/- 144 (SEM) pmol/min/mg protein in the youngest g...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02537197
更新日期:1991-05-01 00:00:00
abstract::The prevalence of colorectal cancer (CRC) continues to increase. Treatment of CRC remains a significant clinical challenge, and effective therapies for advanced CRC are desperately needed. Increasing attention and ongoing research efforts have focused on krill oil that may provide health benefits to the human body. He...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1002/lipd.12281
更新日期:2020-09-15 00:00:00
abstract::Two per thousand pregnant women have hyperthyroidism (HT), and although the symptoms are attenuated during pregnancy, they rebound after delivery, affecting infant development. To examine the effects of hyperthyroidism on lactation, we studied lipid metabolism in maternal mammary glands and livers of hyperthyroid rats...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-001-0787-4
更新日期:2001-08-01 00:00:00
abstract::Lifibrol, a new hypocholesterolemic agent with activity in humans, was examined in normal rats for its short-term and long-term effects on lipid homeostasis. Cholesterol (Chol) synthesis inhibition by lifibrol was demonstrated in vitro in liver minces from normal rats by following [1-14C]acetate ([14C]Ac) and DL-[2-14...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02537074
更新日期:1993-12-01 00:00:00
abstract::The tail gland of the red fox (Vulpes vulpes) secretes lipids containing volatile terpenes used in social communication. We have analysed lipids extracted from fur of the tail gland, body (flanks) and muzzle of foxes. GC-MS showed a novel group of iso-valerate and tiglate monoesters of alkane-1,2-diols (C18:0-22:0). T...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-017-4270-1
更新日期:2017-07-01 00:00:00
abstract::Vegetable oils are an extremely important agricultural commodity. Their use has risen inexorably for the last 50 years and will undoubtedly be even more prevalent in the future. They have a role not only in foodstuffs but also as renewable chemicals. However, our understanding of their metabolism, and particularly its...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/s11745-015-4069-x
更新日期:2015-11-01 00:00:00
abstract::Hydrolysis of synthetic triglycerides by rattlesnake and leopard shark pancreatic enzymes revealed striking differences in specificity, depending on the presence or absence of sodium taurocholate. Without added sodium taurocholate the classical specificity of pancreatic lipase was expressed. Rattlesnake enzymes, in th...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02532361
更新日期:1975-09-01 00:00:00
abstract::The effect of simvastatin, a hypocholesterolemic drug, on the biosynthesis of arachidonic acid was studied in obese and lean Zucker rats. After administration of 2 mg/kg body weight/d for 13 d, delta 6 and delta 5 desaturase activities were measured in liver microsomes at two substrate concentrations. In untreated rat...
journal_title:Lipids
pub_type: 杂志文章
doi:10.1007/BF02536363
更新日期:1993-01-01 00:00:00
abstract::Policosanol is a poorly absorbed nutritional supplement used primarily for cholesterol management. Findings from previous trials evaluating the effects of policosanol are mixed with early data reporting positive lipid effects while more recent studies indicate negligible efficacy. We hypothesized that re-formulating p...
journal_title:Lipids
pub_type: 杂志文章,随机对照试验
doi:10.1007/s11745-011-3591-8
更新日期:2011-10-01 00:00:00