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PubMed2004

Identification of an uptake hydrogenase required for hydrogen-dependent reduction of Fe(III) and other electron acceptors by Geobacter sulfurreducens.

Geobacter sulfurreducens, a representative of the family Geobacteraceae that predominates in Fe(III)-reducing subsurface environments, can grow by coupling the oxidation of hydrogen to the reduction of a variety of electron acceptors, including Fe(III), fumarate, and quinones. An examination of the G. sulfurreducens genome revealed two operons, hya and hyb, which appeared to encode periplasmically oriented respiratory uptake hydrogenases. In order to assess the roles of these two enzymes in hydrogen-dependent growth, Hya- and Hyb-deficient mutants were generated by gene replacement. Hyb was found to be required for hydrogen-dependent reduction of Fe(III), anthraquinone-2,6-disulfonate, and fumarate by resting cell suspensions and to be essential for growth with hydrogen and these three electron acceptors. Hya, in contrast, was not. These findings suggest that Hyb is an essential respiratory hydrogenase in G. sulfurreducens.

Anthraquinones↗

PubMed1977

The tricarboxylic and acid pathway in Desulfovibrio.

Strains of two species of Desulfovibrio were examined for enzymes of the tricarboxylic acid cycle and related pathways. Pyruvate carboxylase (EC6.4.1.1) is present, and alpha-ketoglutarate is formed via the tricarboxylic acids. Glutamate, but not succinyl-CoA, arises from alpha-ketoglutarate. A pathway exists from pyruvate by malic enzyme (EC 1.1.1.39) activity to malate, then fumarate and succinate, again with no evidence of succinyl-CoA formation. The enzymes concerned with metabolism of these dicarboxylic acids show greater activity in the strains that can grow by fumarate dismutation. Glutamate (or glutamine), alpha-ketoglutarate, and yeast extract repress the enzymes that metabolize the tricarboxylic acids. There appears to be no glyoxylate cycle in Desulfovibrio vulgaris or D. desulfuricans.

Anaerobiosis↗

PubMed2006

Side effects of oral iron prophylaxis in pregnancy--myth or reality?

BACKGROUND: It is a common belief among women that iron compounds have unpleasant gastrointestinal side effects. OBJECTIVE: To assess the gastrointestinal side effects of iron prophylaxis in pregnancy. METHODS: A randomized, double-blind study comprising 404 healthy pregnant women allocated to four groups taking ferrous iron supplement (as fumarate) in doses of 20 (n = 99), 40 (n = 100), 60 (n = 102) and 80 mg (n = 103) daily from 18 weeks of gestation to delivery. Iron supplement was predominantly taken at bedtime. Gastrointestinal symptoms (nausea, vomiting, epigastric pain, eructation, pyrosis, meteorism, borborygmi, colic pain, flatulence, constipation, thin feces, diarrhea), black feces, and use of laxatives were recorded by interview at 18, 32 and 39 weeks of gestation. RESULTS: The frequencies of gastrointestinal symptoms were not significantly different in the four iron supplement groups either at inclusion or at 32 and 39 weeks of gestation and thus not related to the iron dose. CONCLUSION: This study shows that a supplement of 20-80 mg ferrous iron (as fumarate), taken between meals, has no clinically significant gastrointestinal side effects. The implementation of iron prophylaxis to pregnant women should not be compromised by undue concern of non-existing side effects.

Administration, Oral↗

PubMed2000

Mycelial pellet formation by Rhizopus oryzae ATCC 20344.

Factors in a cultivation medium affecting fungal growth morphology and fumaric acid production by Rhizopus oryzae ATCC 20344 were investigated. These factors included the initial pH value and trace metals such as zinc, magnesium, iron, and manganese in the cultivation medium. It was found that a significant change in the growth morphology of R. oryzae ATCC 20344 occurs when the initial pH value is varied. A lower initial pH value in the cultivation medium was inhibitory to fungal growth, and fast growth in the cultivation medium at a higher initial pH value promoted the formation of large pellets or filamentous forms. Trace metals in the cultivation media also had significant effects on pellet formation and fumaric acid fermentation.

Cations, Divalent↗

PubMed2004

Effect of inorganic and organic manganese supplementation on the performance and tissue manganese content of broiler chicks.

The effects of dietary levels of manganese (Mn) in inorganic (MnO) and organic (Mn fumarate) forms were evaluated on cockerel chicks. A basal corn-soybean diet with 23 mg/kg Mn was supplemented with levels of 0, 30, 60 and 240 ppm Mn from both Mn sources. Each treatment was replicated in five pens of 10 chicks. The chicks were fed diets ad libitum from 14 to 49 days of age, after which five birds per treatment were sacrificed for pathomorphological examinations and analysis. The treatments did not exert significant effects on the body weight (BW), the feed/gain (F/G) ratio or the mortality rate. According to the necropsy findings, no growth retardation or emaciation occurred in either of the groups and the differences in the average absolute and relative organ weights were not significant (P > 0.05). Tissue analysis indicated that the tibia showed the greatest response to Mn, followed by the liver and kidney. Accumulation in the tibia was higher (P < 0.05) with supplements of 30, 60 and 240 mg/kg from both Mn sources (3.71, 3.78, 4.44, and 3.68, 4.00, 4.36 mg/kg DM, MnO and Mn fumarate, respectively) compared to the control group (3.21 mg/kg). Accumulation in the liver increased significantly (P < 0.05) only with supplements of 60 and 240 ppm independently of the Mn source (12.7, 14.2, and 14.0, 14.9 mg/kg, respectively) compared to the control (9.8 mg/kg). Similarly, kidney tissue Mn was higher (P < 0.05) only with supplements of 60 and 240 ppm (12.8, 12.8, and 13.1, 12.5 mg/kg, respectively) compared to the control (10.2 mg/kg). At the same level of supplementation of the two Mn sources there were no significant differences (P > 0.05) between the Mn concentrations of organs and tissues. Droppings sensitively reflected the intake, whereas blood plasma and feathers showed only the extreme Mn loading.

Animal Feed↗

PubMed1988

The interaction of monofluorofumarate with adenylosuccinate lyase.

Monofluorofumarate was tested as an alternate substrate and inhibitor for adenylosuccinate lyase. Monofluorofumarate was found to be a slow reacting substrate when either AMP or AICAR (5-aminoimidazole 4-carboxamide ribonucleotide) were used as substrate acceptor molecules at pH 7.5. There was no indication that monofluorofumarate could induce the inactivation of adenylosuccinate lyase. The initial reaction product when monofluorofumarate was incubated with AMP in the presence of adenylosuccinate lyase has been determined to be 2-fluoro-adenylosuccinate. This molecule lost HF spontaneously, and the subsequent intermediate was rapidly hydrolyzed to oxalacetate and AMP. A similar reaction scheme was also observed when AICAR was utilized as a cosubstrate with monofluorofumarate. The initial reaction rate when 1.0 mM monofluorofumarate and 1.0 mM AMP were used as substrates with adenylosuccinate lyase was only 1.4% of the rate when 1.0 mM fumarate was used. AICAR (1.0 mM) was found to react with monofluorofumarate at 8.9% of the rate that it reacts with fumarate.

Adenosine Monophosphate↗

PubMed1976

Factors influencing rumen fermentation: effect of hydrogen on formation of propionate.

The effect of hydrogen on fermentation of lactate, pyruvate, fumarate, and succinate by resting rumen microorganisms has been investigated. Under an atmosphere of nitrogen, lactate was fermented to yield acetate as the major product (85 to 100 mole %) and propionate (0 to 17 mole %) and butyrate (0 to 3%) as secondary products. Under hydrogen, there was increased formation of both propionate and total volatile fatty acids. The amount of propionate increased 4 to 8 times and total volatile fatty acids 2.5 to 3.2 times. Propionate formation was proportional to the hydrogen concentration and reached a maximum at a partial pressure of hydrogen of .2 N/m2. With [2-carbon-14] lactate, propionate was formed via the dicarboxylic acid pathway under both nitrogen or hydrogen. Hydrogen did not affect significantly the fermentation of pyruvate or succinate. With fumarate under hydrogen, propionate and total volatile fatty acids increased 6.8 and 2 times while acetate was unchanged. The mechanism by which hydrogen exerts these effects is discussed in relation to the role of methanogenesis in the rumen.

Animals↗

PubMed1992

A defective purine nucleotide synthesis pathway in psoriatic patients.

Purine nucleotide concentrations in skin- and blood-cells of psoriatic patients are abnormal: The increase in the steady state level of cGMP and the decrease in the cAMP concentrations are associated with an enhanced rate of cellular proliferation. Concomitantly we found in the present study decreased ADP and ATP concentrations in blood cells (p less than 0.0001). The change in nucleotide concentrations suggests a defective purine nucleotide synthesis pathway. Stimulation of the Krebs cycle with fumaric acid raises ATP (p less than 0.0001) and most probably cAMP levels and at the same time slows down the purine nucleotide synthesis through end-product inhibition. Both effects can inhibit DNA and protein synthesis activity, which results in inhibition of cellular proliferation. Fumaric acid seems therefore a useful treatment for psoriatic lesions if liver and kidney functions (purine nucleotide and urea cycle) are controlled during treatment.

Adenosine Diphosphate↗

PubMed2003

Effect of antioxidants added to boar semen extender on the semen survival time and sperm chromatin structure.

The aim of the experiment was to determine the effect of potential antioxidants (adenosine, L-cysteine hydrochloride, ascorbic acid, magnesium fumarate and prolactin) supplementing the Biosolwens extender on semen survival time and sperm chromatin structure. The semen motility was examined every day and the susceptibility of sperm chromatin to denaturation was evaluated on collection day and day 15 of storage. The addition of magnesium fumarate to Biosolwens extender increased sperm survival but resulted in the highest increment in the proportion of sperm with damaged chromatin. Biosolwens supplemented with 200 mg of L-cysteine hydrochloride brought the best results. It is possible that lower concentrations of this component would act in a more protective manner. The examination of the chromatin structure appears to be an useful tool for investigation of semen preservation.

Adenosine↗

PubMed2005

A single well push-pull test method for in situ determination of denitrification rates in a nitrate-contaminated groundwater aquifer.

In this study a single-well, "push- pull" test method is adapted for determination of in situ denitrification rates in groundwater aquifers. The rates of stepwise reduction of nitrate to nitrite, nitrous oxide, and molecular nitrogen were determined by performing a series of push-pull tests. The method consists of the controlled injection of a prepared test solution ("push") into an aquifer followed by the extraction of the test solution/ground water mixture ("pull") from the same location. The injected test solution consists of ground water containing a nonreactive tracer and one or more biologically reactive solutes. Reaction rate coefficients are computed from the mass of reactant consumed and/or product formed. A single Transport Test, one Biostimulation Test, and four Activity Tests were conducted for this study. Transport tests are conducted to evaluate the mobility of solutes used in subsequent tests. These included bromide (a conservative tracer), fumarate (a carbon and/or source), and nitrate (an electron acceptor). Extraction phase breakthrough curves for all solutes were similar, indicating apparent conservative transport of the solutes prior to biostimulation. Biostimulation tests were conducted to stimulate the activity of indigenous heterotrophic denitrifying microorganisms and consisted of injection of site ground water containing fumarate and nitrate. Biostimulation was detected by the simultaneous production of carbon dioxide and nitrite after each injection. Activity tests were conducted to quantify rates of nitrate, nitrite, and nitrous oxide reduction. Estimated zero-order degradation rates decreased in the order nitrate > nitrite > nitrous oxide. The series of push-pull tests developed and field tested in this study should prove useful for conducting rapid, low-cost feasibility assessments for in situ denitrification in nitrate-contaminated aquifers.

Biodegradation, Environmental↗

PubMed1991

Isoelectrofocusing of rat muscle adenylosuccinase.

Adenylosuccinase catalyses the conversion of adenylosuccinic acid to AMP and fumarate. We have developed a coupled enzyme staining procedure applicable to nitrocellulose blots after agarose gel isoelectrofocusing of rat muscle adenylosuccinase. The coupling enzymes, fumarase (fumarate to L-malate) and malic enzyme (L-malate to pyruvate and NADPH), are adsorbed to nitrocellulose prior to blotting. The NADPH, mediated by phenazine methosulfate, converts a tetrazolium salt to its blue formazan. This procedure demonstrated that rat muscle adenylosuccinase consists of three isomeric forms present in similar amounts.

Adenosine Monophosphate↗

PubMed1982

Mitochondrial malate dehydrogenase, decarboxylating ("malic" enzyme) and transhydrogenase activities of adult Hymenolepis microstoma (Cestoda).

Adult H. microstoma mitochondria catalyzed a malate dehydrogenase, decarboxylating ("malic" enzyme) activity. This "malic" enzyme was found as a soluble component of the mitochondrion, was specific for NADP, and required a divalent cation with Mn++ ion yielding the greatest activity. The H. microstoma "malic" enzyme could fulfill the need for generating intramitochondrial reducing equivalents required for electron transport. The H. microstoma mitochondria also exhibited an NADPH:NAD transhydrogenation reaction. The electron transport system of this cestode was apparently specific for NADH both in terms of the rotenone-sensitive oxidase and fumarate reductase systems. Electron transport-associated NADPH oxidation was increased markedly with the addition of NAD to the system. Coupling of NADPH utilization to fumarate reduction, in the presence of NAD, was apparent under conditions of reduced oxygen tension. This was consistent with the presence of the NADPH:NAD transhydrogenase which catalyzed a transfer of reducing equivalents from NADPH to NAD, producing NADH for electron transport function. The data presented suggest that H. microstoma mitochondria can engage in an anaerobic, electron transport-associated production of succinate, and presumably concomitant phosphorylation. Malate may serve as the mitochondrial substrate supplying reducing equivalents for electron transport via the activity of the "malic" enzyme coupled to the NADPH:NAD transhydrogenase. In addition to the NADPH:NAD transhydrogenase activity, H. microstoma mitochondria catalyzed an NADH:NAD transhydrogenation.

Animals↗

PubMedDate not supplied

[Oxidation of Krebs cycle substrates by Eurytrema pancreaticum mitochondria].

From tissues of E. pancreaticum were isolated mitochondria capable to swell under the effect of some factors. The intensive oxidation of succinate, isocitrate, cisaconitate, oxalacetate and alpha-ketoglutarate by mitochondria and less intensive one of malate, fumarate, citrate and pyruvate were shown. NAD caused the rise in oxidation intensity of isocitrate, cis-aconitate, oxalacetate, alpha-ketoglutarate, malate, fumarate and pyruvate while NADP--of isocitrate and citrate.

Aconitic Acid↗

PubMed1994

Dose-response study of N,N-dimethyltryptamine in humans. II. Subjective effects and preliminary results of a new rating scale.

BACKGROUND: Validation of animal models of hallucinogenic drugs' subjective effects requires human data. Previous human studies used varied groups of subjects and assessment methods. Rating scales for hallucinogen effects emphasized psychodynamic principles or the drugs' dysphoric properties. We describe the subjective effects of graded doses of N,N-dimethyltryptamine (DMT), an endogenous hallucinogen and drug of abuse, in a group of experienced hallucinogen users. We also present preliminary data from a new rating scale for these effects. METHODS: Twelve highly motivated volunteers received two doses (0.04 and 0.4 mg/kg) of intravenous (IV) dimethyltryptamine fumarate "nonblind," before entering a double-blind, saline placebo-controlled, randomized study using four doses of IV DMT. Subjects were carefully interviewed after resolution of drug effects, providing thorough and systematic descriptions of DMT's effects. They also were administered a new instrument, the Hallucinogen Rating Scale (HRS). The HRS was drafted from interviews obtained from an independent sample of 19 experienced DMT users, and modified during early stages of the study. RESULTS: Psychological effects of IV DMT began almost immediately after administration, peaked at 90 to 120 seconds, and were almost completely resolved by 30 minutes. This time course paralleled DMT blood levels previously described. Hallucinogenic effects were seen after 0.2 and 0.4 mg/kg of dimethyltryptamine fumarate, and included a rapidly moving, brightly colored visual display of images. Auditory effects were less common. "Loss of control," associated with a brief, but overwhelming "rush," led to a dissociated state, where euphoria alternated or coexisted with anxiety. These effects completely replaced subjects' previously ongoing mental experience and were more vivid and compelling than dreams or waking awareness. Lower doses, 0.1 and 0.05 mg/kg, were primarily affective and somaesthetic, while 0.1 mg/kg elicited the least desirable effects. Clustering of HRS items, using either a clinical, mental status method or principal components factor analysis provided better resolution of dose effects than did the biological variables described previously. CONCLUSIONS: These clinical and preliminary quantitative data provide bases for further psychopharmacologic characterization of DMT's properties in humans. They also may be used to compare the effects of other agents affecting relevant brain receptors in volunteer and psychiatric populations.

Cognition↗

PubMed1996

Analysis of the oxidative catabolism of retinoic acid in rat Dunning R3327G prostate tumors.

We studied the enzymatic characteristics of the oxidative catabolism of retinoic acid (RA) and its inhibition by liarozole-fumarate in homogenates of rat Dunning R3327G prostate tumors. Homogenates of rat liver were used as reference material. Both tumor and liver homogenates were able to catabolize retinoic acid. HPLC analysis revealed only very polar metabolites in tumors, while in the liver both metabolites with intermediate polarity and more polar metabolites were found. Kinetic analysis of retinoic acid catabolism showed a K(m) of 1.7 +/- 0.7 microM and a Vmax of 4.2 +/- 4.4 pmol polar RA metabolites/mg protein/hr for Dunning G tumor homogenates. In liver homogenates a K(m) value of 4.3 +/- 0.5 microM and a Vmax value of 290 +/- 120 pmol polar RA metabolites/mg protein/hr were obtained. Liarozole-fumarate inhibited retinoic acid catabolism in Dunning tumors and liver with IC50 values of 0.26 +/- 0.16 microM and 0.14 +/- 0.05, respectively. The results suggest that rat Dunning R3327G tumors are able to metabolize retinoic acid in a manner similar to that found in rat liver but with a lower metabolizing capacity.

Animals↗

PubMed1999

Genotoxicity of iron compounds in Salmonella typhimurium and L5178Y mouse lymphoma cells.

The mutagenic activity of elemental and salt forms of iron (Fe), including compounds currently being used in dietary supplements and for food fortification, were evaluated for mutagenicity in Salmonella typhimurium and L5178Y mouse lymphoma cells. Except for the weak response obtained with ferrous fumarate, none of the compounds induced a mutagenic response in Salmonella. In the mouse lymphoma assay, responses were related to the Fe compound and/or reduction of ferric (Fe+3) to ferrous (Fe+2). Responses with the elemental forms of Fe were divergent. Electrolytic Fe with a relatively larger particle size and irregular shape was negative. The smaller-sized carbonyl Fe, which after 4 hr attached to and was taken up by the cells, induced mutagenic responses both with and without S9. With ferric chloride (FeCl3) and ferric phosphate (FePO4), there was an increase in mutant frequency only with S9. With the Fe+2 compounds, ferrous sulfate (FeSO4) and ferrous fumarate (FeC4H2O4), positive responses were observed without S9. The Fe chelate, sodium Fe(III)EDTA was positive in both the presence and absence of S9. The lowest effective doses (LED) for induction of mutagenicity were identified for these compounds and an LED ratio calculated. The LED ratio ranges from 1 for FeSO4 to 30 for carbonyl Fe, which are similar to oral LD50 values obtained in animal studies.

Animals↗

PubMed2002

Multifunctional folded polypeptides from peptide synthesis and site-selective self-functionalization--practical scaffolds in aqueous solution.

The site selectivity of His-mediated lysine and ornithine side-chain acylation in a designed four-helix bundle protein scaffold was mapped by reaction of several polypeptides with one equivalent of mono-p-nitrophenyl fumarate in aqueous solution at pH 5.9 and room temperature followed by an analysis of the degrees and sites of acylation. Integration of the HPLC chromatograms of the acylated polypeptides and trypsin cleavage followed by mass spectrometry analysis of the tryptic fragments provided the experimental evidence. Based on these and previously published results a strategy was developed for the site-selective and stepwise incorporation of three residues into a folded polypeptide in aqueous solution at room temperature. The first substituent was incorporated by reaction of a 1.7-fold excess of the corresponding active ester with the polypeptide at pH 5.9, the second substituent was introduced in a 3-fold excess after the pH value was raised to 8, and the third substituent was incorporated by reaction of a 10-fold excess with the polypeptide at pH 5.9. No intermediate steps of purification were taken and the overall yield was 30 % or more. Examples of the substituents included are carbohydrates, an enzyme inhibitor, a fumarate, and an acetate group. The introduction of different substituents into three individually addressable positions in a stepwise, efficient, and controllable reaction demonstrates that designed folded polypeptides are practically useful scaffolds that can be functionalized by using very simple chemistry in aqueous solution. Predicted applications include designed receptors, biosensors, and molecular devices.

Acylation↗

PubMed2005

Hydrogen bonding and dynamic behaviour in crystals and polymorphs of dicarboxylic-diamine adducts: a comparison between NMR parameters and X-ray diffraction studies.

Fumaric, malonic, maleic, and hydromuconic (HOOCCH2(CH)2CH2COOH) acids were used to prepare a series of hydrogen-bonded adducts or salts, depending on whether acid-base proton transfer takes place, with the dibase [N(muCH2CH2)3N] in various stoichiometric ratios. The resulting compounds have been investigated by using the 1H MAS, 15N, and 13C cross polarisation magic-angle spinning (CPMAS) methods and discussed in relation to X-ray diffraction studies to ascertain the nature of the O-HO, NH-O, and N+-HO- hydrogen bonds between the various species. In addition, two polymorphic forms of the malonic compound and a hydrate in the maleic case were examined. We also present the correlations between the chemical shifts of the hydrogen-bonded protons and those from the proton transfer reaction (acid-to-base) with the heavy atom distances. The dynamic behaviour in the solid-state of the [N(muCH2CH2)3N] adducts with fumaric 2:1, maleic 1:1 hydrate, and hydromuconic acids, and a malonate 2:1 polymorph adduct have been investigated by using variable-temperature 1H spin-lattice relaxation times. A substantial agreement between the activation energies obtained from fitting the T1 data and the results of potential energy barrier calculations demonstrates that the facile reorientation of the [N(muCH2CH2)3N] molecule occurs in several of the adducts.

Journal Article↗