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Butyrobetaine

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https://www.readbyqxmd.com/read/29699662/ruminant-meat-and-milk-contain-%C3%AE-valerobetaine-another-precursor-of-trimethylamine-n-oxide-tmao-like-%C3%AE-butyrobetaine
#1
Luigi Servillo, Nunzia D'Onofrio, Alfonso Giovane, Rosario Casale, Domenico Cautela, Domenico Castaldo, Francesco Iannaccone, Gianluca Neglia, Giuseppe Campanile, Maria Luisa Balestrieri
Quaternary ammonium compounds containing N-trimethylamino moiety, such as choline derivatives and carnitine, abundant in meat and dairy products, are metabolic precursors of trimethylamine (TMA). A similar fate is reported for Nε -trimethyllysine and γ-butyrobetaine. With the aim at investigating the metabolic profile of such metabolites in most employed animal dietary sources, HPLC-ESI-MS/MS analyses on ruminant and non-ruminant milk and meat were performed. Results demonstrate, for the first time, the presence of δ-valerobetaine, occurring at levels higher than γ-butyrobetaine in all ruminant samples compared to non-ruminants...
September 15, 2018: Food Chemistry
https://www.readbyqxmd.com/read/29325058/serum-carnitine-metabolites-and-incident-type-2-diabetes-mellitus-in-patients-with-suspected-stable-angina-pectoris
#2
Elin Strand, Eirik W Rebnord, Malin R Flygel, Vegard Lysne, Gard F T Svingen, Grethe S Tell, Kjetil H Løland, Rolf K Berge, Asbjørn Svardal, Ottar Nygård, Eva R Pedersen
Context: Carnitine and its metabolites are centrally involved in fatty acid metabolism. Although elevated circulating concentrations have been observed in obesity and insulin resistance, prospective studies examining whether these metabolites are associated with incident type 2 diabetes mellitus (T2D) are sparse. Objective: We performed a comprehensive evaluation of metabolites along the carnitine pathway relative to incident T2D. Design: A total of 2519 patients (73...
March 1, 2018: Journal of Clinical Endocrinology and Metabolism
https://www.readbyqxmd.com/read/29178259/the-effect-of-different-l-carnitine-administration-routes-on-the-development-of-atherosclerosis-in-apoe-knockout-mice
#3
Ying Zhao, Ning Yang, Jinmao Gao, Hanying Li, Wei Cai, Xin Zhang, Yongqiang Ma, Xiulong Niu, Guohong Yang, Xin Zhou, Yuming Li
SCOPE: l-Carnitine (LC) is abundant in red meat and is widely added to health supplements and food. This study focuses on the adverse effects of oral supplementation of 1.3% LC in ApoE-/- mice and whether the parenteral administration of LC (subcutaneously, sub) has any impact on the development of atherosclerosis. METHODS AND RESULTS: Mice are randomly divided into three groups (n = 15). All mice are fed a high-fat diet (HFD). The number of Ly6Chi monocytes; degree of atherosclerosis; plasma LC, γ-butyrobetaine (γBB), and trimethylamine-N-oxide (TMAO) levels; and microbial community composition are analyzed...
March 2018: Molecular Nutrition & Food Research
https://www.readbyqxmd.com/read/29110324/cnta-oxygenase-substrate-profile-comparison-and-oxygen-dependency-of-tma-production-in-providencia-rettgeri
#4
Gints Kalnins, Eduards Sevostjanovs, Dace Hartmane, Solveiga Grinberga, Kaspars Tars
CntA oxygenase is a Rieske 2S-2Fe cluster-containing protein that has been previously described as able to produce trimethylamine (TMA) from carnitine, gamma-butyrobetaine, glycine betaine, and in one case, choline. TMA found in humans is exclusively of bacterial origin, and its metabolite, trimethylamine oxide (TMAO), has been associated with atherosclerosis and heart and renal failure. We isolated four different Rieske oxygenases and determined that there are no significant differences in their substrate panels...
January 2018: Journal of Basic Microbiology
https://www.readbyqxmd.com/read/29065368/bbox1-is-down-regulated-in-maternal-immune-activated-mice-and-implicated-in-genetic-susceptibility-to-human-schizophrenia
#5
Hwayoung Lee, Hyung-Ki Kim, Jun-Tack Kwon, Shohyun Park, Hae Jeong Park, Su Kang Kim, Jin Kyung Park, Won Sub Kang, Young Jong Kim, Joo-Ho Chung, Jong Woo Kim, Hak-Jae Kim
Prenatal exposure to infectious or inflammatory insults can increase the risk of developing neuropsychiatric disorders such as bipolar disorder, autism, and schizophrenia in later life. Gamma-butyrobetaine hydroxylase (BBOX 1) is an enzyme responsible for the biosynthesis of l-carnitine, a key molecule in fatty acid metabolism. This cytosolic dimeric protein belongs to the dioxygenase family. In this study, we investigated whether BBOX 1 expression was related to psychiatric disorder in an animal model. We also conducted a case-control study using 284 schizophrenia patients and 409 controls with single-nucleotide polymorphisms (SNPs) in the 5'-near region of BBOX 1...
January 2018: Psychiatry Research
https://www.readbyqxmd.com/read/28668962/acute-exercise-stimulates-carnitine-biosynthesis-and-octn2-expression-in-mouse-kidney
#6
Tom L Broderick, Frank A Cusimano, Chelsea Carlson, Leslie K Tamura
BACKGROUND/AIMS: Carnitine is essential for the transport of long-chain FAs (FA) into the mitochondria for energy production. During acute exercise, the increased demand for FAs results in a state of free carnitine deficiency in plasma. The role of kidney in carnitine homeostasis after exercise is not known. METHODS: Swiss Webster mice were sacrificed immediately after a 1-hour moderate intensity treadmill run, and at 4-hours and 8-hours into recovery. Non-exercising mice served as controls...
2017: Kidney & Blood Pressure Research
https://www.readbyqxmd.com/read/28393236/metabolomic-analysis-of-the-saliva-of-japanese-patients-with-oral-squamous-cell-carcinoma
#7
Mitsuyoshi Ohshima, Keisuke Sugahara, Kiyohiro Kasahara, Akira Katakura
The aim of the present study was to characterize the metabolic systems in Japanese patients with oral squamous cell carcinoma (OSCC) using capillary electrophoresis-mass spectrometry (CE-MS) metabolome analysis of saliva samples. A previous study showed variations among ethnicities and tumor sites in the saliva metabolome of patients with OSCC using CE-MS. In the present study, saliva was obtained from 22 Japanese patients with OSCC and from 21 healthy controls who visited the Department of Dentistry, Oral and Maxillofacial Surgery, Tokyo Dental Collage Ichikawa General Hospital, Tokyo, Japan, and all samples were subject to comprehensive quantitative metabolome analysis using CE-MS...
May 2017: Oncology Reports
https://www.readbyqxmd.com/read/27993177/diets-high-in-resistant-starch-increase-plasma-levels-of-trimethylamine-n-oxide-a-gut-microbiome-metabolite-associated-with-cvd-risk
#8
RANDOMIZED CONTROLLED TRIAL
Nathalie Bergeron, Paul T Williams, Regina Lamendella, Nastaran Faghihnia, Alyssa Grube, Xinmin Li, Zeneng Wang, Rob Knight, Janet K Jansson, Stanley L Hazen, Ronald M Krauss
Production of trimethylamine-N-oxide (TMAO), a biomarker of CVD risk, is dependent on intestinal microbiota, but little is known of dietary conditions promoting changes in gut microbial communities. Resistant starches (RS) alter the human microbiota. We sought to determine whether diets varying in RS and carbohydrate (CHO) content affect plasma TMAO levels. We also assessed postprandial glucose and insulin responses and plasma lipid changes to diets high and low in RS. In a cross-over trial, fifty-two men and women consumed a 2-week baseline diet (41 percentage of energy (%E) CHO, 40 % fat, 19 % protein), followed by 2-week high- and low-RS diets separated by 2-week washouts...
December 2016: British Journal of Nutrition
https://www.readbyqxmd.com/read/27983775/carnitine-and-%C3%AE-butyrobetaine-stimulate-elimination-of-meldonium-due-to-competition-for-octn2-mediated-transport
#9
Edgars Liepinsh, Elina Makarova, Eduards Sevostjanovs, Dace Hartmane, Helena Cirule, Olga Zharkova-Malkova, Solveiga Grinberga, Maija Dambrova
Meldonium (3-(2,2,2-trimethylhydrazinium)propionate) is the most potent clinically used inhibitor of organic cation transporter 2 (OCTN2). Inhibition of OCTN2 leads to a decrease in carnitine and acylcarnitine contents in tissues and energy metabolism optimization-related cardioprotective effects. The recent inclusion of meldonium in the World Anti-Doping Agency List of Prohibited Substances and Methods has raised questions about the pharmacokinetics of meldonium and its unusually long elimination time. Therefore, in this study, the rate of meldonium washout after the end of the treatment was tested with and without administration of carnitine, γ-butyrobetaine (GBB) and furosemide to evaluate the importance of competition for OCTN2 transport in mice...
May 2017: Basic & Clinical Pharmacology & Toxicology
https://www.readbyqxmd.com/read/27730694/acylcarnitines-as-markers-of-exercise-associated-fuel-partitioning-xenometabolism-and-potential-signals-to-muscle-afferent-neurons
#10
Jie Zhang, Alan R Light, Charles L Hoppel, Caitlin Campbell, Carol J Chandler, Dustin J Burnett, Elaine C Souza, Gretchen A Casazza, Ronald W Hughen, Nancy L Keim, John W Newman, Gary R Hunter, Jose R Fernandez, W Timothy Garvey, Mary-Ellen Harper, Oliver Fiehn, Sean H Adams
What is the central question of this study? Does improved metabolic health and insulin sensitivity following a weight-loss and fitness intervention in sedentary, obese women alter exercise-associated fuel metabolism and incomplete mitochondrial fatty acid oxidation (FAO), as tracked by blood acylcarnitine patterns? What is the main finding and its importance? Despite improved fitness and blood sugar control, indices of incomplete mitochondrial FAO increased in a similar manner in response to a fixed load acute exercise bout; this indicates that intramitochondrial muscle FAO is inherently inefficient and is tethered directly to ATP turnover...
January 1, 2017: Experimental Physiology
https://www.readbyqxmd.com/read/27562416/fluorescent-derivatization-combined-with-aqueous-solvent-based-dispersive-liquid-liquid-microextraction-for-determination-of-butyrobetaine-l-carnitine-and-acetyl-l-carnitine-in-human-plasma
#11
Yi-Ching Chen, Chia-Ju Tsai, Chia-Hsien Feng
A novel aqueous solvent-based dispersive liquid-liquid microextraction (AS-DLLME) method was combined with narrow-bore liquid chromatography and fluorescence detection for the determination of hydrophilic compounds. A remover (non-polar solvent) and extractant (aqueous solution) were introduced into the derivatization system (acetonitrile) to obtain a water-in-oil emulsion state that increased the mass transfer of analytes. As a proof of concept, three quaternary ammonium substances, including butyrobetaine, l-carnitine and acetyl-l-carnitine, were also used as analytes and determined in pharmaceuticals, personal care products, food and human plasma...
September 16, 2016: Journal of Chromatography. A
https://www.readbyqxmd.com/read/27125317/purification-gene-cloning-and-characterization-of-%C3%AE-butyrobetainyl-coa-synthetase-from-agrobacterium-sp-525a
#12
Hiroshi Fujimitsu, Akira Matsumoto, Sayaka Takubo, Akiko Fukui, Kazuma Okada, Isam A Mohamed Ahmed, Jiro Arima, Nobuhiro Mori
The report is the first of purification, overproduction, and characterization of a unique γ-butyrobetainyl CoA synthetase from soil-isolated Agrobacterium sp. 525a. The primary structure of the enzyme shares 70-95% identity with those of ATP-dependent microbial acyl-CoA synthetases of the Rhizobiaceae family. As distinctive characteristics of the enzyme of this study, ADP was released in the catalytic reaction process, whereas many acyl CoA synthetases are annotated as an AMP-forming enzyme. The apparent Km values for γ-butyrobetaine, CoA, and ATP were, respectively, 0...
August 2016: Bioscience, Biotechnology, and Biochemistry
https://www.readbyqxmd.com/read/27112275/the-impact-of-altered-carnitine-availability-on-acylcarnitine-metabolism-energy-expenditure-and-glucose-tolerance-in-diet-induced-obese-mice
#13
Marieke G Schooneman, Riekelt H Houtkooper, Carla E M Hollak, Ronald J A Wanders, Frédéric M Vaz, Maarten R Soeters, Sander M Houten
AIM: Acylcarnitines are fatty acid oxidation (FAO) intermediates, which have been implicated in diet-induced insulin resistance. Elevated acylcarnitine levels are found in obese, insulin resistant humans and rodents, and coincide with lower free carnitine. We hypothesized that increasing free carnitine levels by administration of the carnitine precursor γ-butyrobetaine (γBB) could facilitate FAO, thereby improving insulin sensitivity. METHODS: C57BL/6N mice were fed with a high fat or chow diet with or without γBB supplementation (n=10 per group)...
August 2016: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/27081744/major-increase-in-microbiota-dependent-proatherogenic-metabolite-tmao-one-year-after-bariatric-surgery
#14
Marius Trøseid, Johannes R Hov, Torunn Kristin Nestvold, Hanne Thoresen, Rolf K Berge, Asbjørn Svardal, Knut Tore Lappegård
BACKGROUND: Trimethylamine-N-oxide (TMAO) is formed in the liver from trimethylamine (TMA), a product exclusively generated by the gut microbiota from dietary phosphatidylcholine and carnitine. An alternative pathway of TMAO formation from carnitine is via the microbiota-dependent intermediate γ-butyrobetaine (γBB). Elevated TMAO levels are associated with cardiovascular disease (CVD), but little is known about TMAO in obesity. Given the proposed contribution of microbiota alterations in obesity and type 2 diabetes (T2D), we investigated the potential impact of obesity, lifestyle-induced weight loss, and bariatric surgery on plasma levels of TMAO, its microbiota-dependent intermediate γBB, and its diet-dependent precursors carnitine and choline...
May 2016: Metabolic Syndrome and related Disorders
https://www.readbyqxmd.com/read/27057307/metabolomics-studies-identify-novel-diagnostic-and-prognostic-indicators-in-patients-with-alcoholic-hepatitis
#15
Mona Ascha, Zeneng Wang, Mustafa S Ascha, Raed Dweik, Nizar N Zein, David Grove, J Mark Brown, Stephanie Marshall, Rocio Lopez, Ibrahim A Hanouneh
AIM: To identify plasma analytes using metabolomics that correlate with the diagnosis and severity of liver disease in patients with alcoholic hepatitis (AH). METHODS: We prospectively recruited patients with cirrhosis from AH (n = 23) and those with cirrhosis with acute decompensation (AD) from etiologies other than alcohol (n = 25). We used mass spectrometry to identify 29 metabolic compounds in plasma samples from fasted subjects. A receiver operating characteristics analysis was performed to assess the utility of biomarkers in distinguishing acute AH from alcoholic cirrhosis...
April 8, 2016: World Journal of Hepatology
https://www.readbyqxmd.com/read/26868510/the-carnitine-butyrobetaine-trimethylamine-n-oxide-pathway-and-its-association-with-cardiovascular-mortality-in-patients-with-carotid-atherosclerosis
#16
Karolina Skagen, Marius Trøseid, Thor Ueland, Sverre Holm, Azhar Abbas, Ida Gregersen, Martin Kummen, Vigdis Bjerkeli, Frode Reier-Nilsen, David Russell, Asbjørn Svardal, Tom Hemming Karlsen, Pål Aukrust, Rolf K Berge, Johannes E R Hov, Bente Halvorsen, Mona Skjelland
BACKGROUND AND PURPOSE: γ-butyrobetaine (γBB) is a metabolite from dietary Carnitine, involved in the gut microbiota-dependent conversion from Carnitine to the pro-atherogenic metabolite trimethylamine-N-oxide (TMAO). Orally ingested γBB has a pro-atherogenic effect in experimental studies, but γBB has not been studied in relation to atherosclerosis in humans. The aim of this study was to evaluate associations between serum levels of γBB, TMAO and their common precursors Carnitine and trimethyllysine (TML) and carotid atherosclerosis and adverse outcome...
April 2016: Atherosclerosis
https://www.readbyqxmd.com/read/26850121/pharmacological-effects-of-meldonium-biochemical-mechanisms-and-biomarkers-of-cardiometabolic-activity
#17
REVIEW
Maija Dambrova, Marina Makrecka-Kuka, Reinis Vilskersts, Elina Makarova, Janis Kuka, Edgars Liepinsh
Meldonium (mildronate; 3-(2,2,2-trimethylhydrazinium)propionate; THP; MET-88) is a clinically used cardioprotective drug, which mechanism of action is based on the regulation of energy metabolism pathways through l-carnitine lowering effect. l-Carnitine biosynthesis enzyme γ-butyrobetaine hydroxylase and carnitine/organic cation transporter type 2 (OCTN2) are the main known drug targets of meldonium, and through inhibition of these activities meldonium induces adaptive changes in the cellular energy homeostasis...
November 2016: Pharmacological Research: the Official Journal of the Italian Pharmacological Society
https://www.readbyqxmd.com/read/26660433/cation-%C3%AF-interactions-contribute-to-substrate-recognition-in-%C3%AE-butyrobetaine-hydroxylase-catalysis
#18
Jos J A G Kamps, Amjad Khan, Hwanho Choi, Robert K Lesniak, Jürgen Brem, Anna M Rydzik, Michael A McDonough, Christopher J Schofield, Timothy D W Claridge, Jasmin Mecinović
γ-Butyrobetaine hydroxylase (BBOX) is a non-heme Fe(II) - and 2-oxoglutarate-dependent oxygenase that catalyzes the stereoselective hydroxylation of an unactivated C-H bond of γ-butyrobetaine (γBB) in the final step of carnitine biosynthesis. BBOX contains an aromatic cage for the recognition of the positively charged trimethylammonium group of the γBB substrate. Enzyme binding and kinetic analyses on substrate analogues with P and As substituting for N in the trimethylammonium group show that the analogues are good BBOX substrates, which follow the efficiency trend N(+) >P(+) >As(+)...
January 22, 2016: Chemistry: a European Journal
https://www.readbyqxmd.com/read/26458767/quantitative-acylcarnitine-determination-by-uhplc-ms-ms-going-beyond-tandem-ms-acylcarnitine-profiles
#19
Paul E Minkler, Maria S K Stoll, Stephen T Ingalls, Janos Kerner, Charles L Hoppel
Tandem MS "profiling" of acylcarnitines and amino acids was conceived as a first-tier screening method, and its application to expanded newborn screening has been enormously successful. However, unlike amino acid screening (which uses amino acid analysis as its second-tier validation of screening results), acylcarnitine "profiling" also assumed the role of second-tier validation, due to the lack of a generally accepted second-tier acylcarnitine determination method. In this report, we present results from the application of our validated UHPLC-MS/MS second-tier method for the quantification of total carnitine, free carnitine, butyrobetaine, and acylcarnitines to patient samples with known diagnoses: malonic acidemia, short-chain acyl-CoA dehydrogenase deficiency (SCADD) or isobutyryl-CoA dehydrogenase deficiency (IBD), 3-methyl-crotonyl carboxylase deficiency (3-MCC) or ß-ketothiolase deficiency (BKT), and methylmalonic acidemia (MMA)...
December 2015: Molecular Genetics and Metabolism
https://www.readbyqxmd.com/read/26371012/a-phospholipid-protein-complex-from-antarctic-krill-reduced-plasma-homocysteine-levels-and-increased-plasma-trimethylamine-n-oxide-tmao-and-carnitine-levels-in-male-wistar-rats
#20
Bodil Bjørndal, Marie S Ramsvik, Carine Lindquist, Jan E Nordrehaug, Inge Bruheim, Asbjørn Svardal, Ottar Nygård, Rolf K Berge
Seafood is assumed to be beneficial for cardiovascular health, mainly based on plasma lipid lowering and anti-inflammatory effects of n-3 polyunsaturated fatty acids. However, other plasma risk factors linked to cardiovascular disease are less studied. This study aimed to penetrate the effect of a phospholipid-protein complex (PPC) from Antarctic krill on one-carbon metabolism and production of trimethylamine-N-oxide (TMAO) in rats. Male Wistar rats were fed isoenergetic control, 6%, or 11% PPC diets for four weeks...
September 2015: Marine Drugs
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