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Results for “LEVULINIC ACID”

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At least 19 recordsLinked to original sources
PubMed1979

Modulation of cytochrome biosynthesis in yeast by antimetabolite action of levulinic acid.

Levulinic acid, a competitive inhibitor of delta-aminolevulinic acid dehydratase, was used to inhibit cytochrome biosynthesis in growing yeast cells. In Saccharomyces cerevisiae the antimetabolite acts by inhibiting delta-aminolevulinic acid dehydratase in vivo, causing an accumulation of intracellular delta-aminolevulinic acid and simultaneous decreases in all classes of mitochondrial cytochromes. Changes in cellular cytochrome content with increasing levulinic acid concentration suggested the existence of different regulatory patterns in S. cerevisiae and Candida utilis. In C. utilis, cytochrome a.a3 formation is very resistant to the antimetabolite action of levulinic acid. In this aerobic yeast, cytochrome c+c1 is the most sensitive to levulinic acid, and cytochrome b exhibits intermediate sensitivity.

Candida↗
PubMed2001

Simultaneous determination of delta-aminolevulinic acid, porphobilinogen, levulinic acid and glycine in culture broth by capillary electrophoresis.

Capillary electrophoretic simultaneous determination of a mixture containing delta-aminolevulinic acid, porphobilinogen, levulinic acid and glycine was investigated. With increases in the sodium tetraborate buffer concentration (5-70 mM), resolution of the four components was improved, but the migration time was increased. Alternatively, with increases in the applied voltage (5-22.5 kV), a shortened migration time was seen but this adversely affected resolution. The components were separated with high resolution by using a fused-silica capillary column (75 cm x 75 microm I.D.) filled with 30 mM sodium tetraborate buffer (pH 9.3-9.4) under the applied voltage of 20 kV (constant voltage mode). When the established method was applied to the culture broth of Rhodopseudomonas sphaeroides, a photosynthetic bacterium, the four components mentioned above were separated with good resolution. Furthermore, the use of this method would provide a fast, sensitive and specific method for monitoring the administration of delta-aminolevulinic acid in photodynamic cancer therapy, for the measurement of delta-aminolevulinic acid dehydratase activity in erythrocytes, and for testing the delta-aminolevulinic acid assay and for impurities in drug formulation.

Aminolevulinic Acid↗
PubMed2002

Experimental studies for levulinic acid production from whole kernel grain sorghum.

Levulinic acid has potential as an important basic chemical material. This study proposed a method of making levulinic acid using abundant and low cost whole kernel sorghum grain as the raw material. Flour made from grinding whole kernel sorghum grains was blended with 2%, 5% and 8% aqueous solutions of sulfuric acid. Mixtures were heated to 160 or 200 degrees C in a pressurized reactor. A stepwise heating scheme helped improve the yield of levulinic acid. Levulinic acid yield was determined based on sorghum flour content, as opposed to total sorghum mass. Levulinic acid yield increased as reaction temperature increased. Higher sulfuric acid concentration also significantly increased the levulinic acid yield. However, flour loading had an adverse effect on levulinic acid yield. A maximum yield of 32.6% levulinic acid was achieved at 200 degrees C, 8% sulfuric acid concentration and 10% flour loading. A linear regression model was capable of predicting the levulinic acid yield with respect to effects of reaction temperature, mineral acid concentration and flour loading (R2 = 0.88).

Edible Grain↗
PubMed1999

X-ray structure of 5-aminolevulinic acid dehydratase from Escherichia coli complexed with the inhibitor levulinic acid at 2.0 A resolution.

5-Aminolevulinic acid dehydratase (ALAD), an early enzyme of the tetrapyrrole biosynthesis pathway, catalyzes the dimerization of 5-aminolevulinic acid to form the pyrrole, porphobilinogen. ALAD from Escherichia coli is shown to form a homo-octameric structure with 422 symmetry in which each subunit adopts the TIM barrel fold with a 30-residue N-terminal arm. Pairs of monomers associate with their arms wrapped around each other. Four of these dimers interact, principally via their arm regions, to form octamers in which each active site is located on the surface. The active site contains two lysine residues (195 and 247), one of which (Lys 247) forms a Schiff base link with the bound substrate analogue, levulinic acid. Of the two substrate binding sites (referred to as A and P), our analysis defines the residues forming the P-site, which is where the first ALA molecule to associate with the enzyme binds. The carboxyl group of the levulinic acid moiety forms hydrogen bonds with the side chains of Ser 273 and Tyr 312. In proximity to the levulinic acid is a zinc binding site formed by three cysteines (Cys 120, 122, and 130) and a solvent molecule. We infer that the second substrate binding site (or A-site) is located between the triple-cysteine zinc site and the bound levulinic acid moiety. Two invariant arginine residues in a loop covering the active site (Arg 205 and Arg 216) appear to be appropriately placed to bind the carboxylate of the A-site substrate. Another metal binding site, close to the active site flap, in which a putative zinc ion is coordinated by a carboxyl and five solvent molecules may account for the activating properties of magnesium ions.

Binding Sites↗
PubMed1979

Effect of levulinic acid on pigment biosynthesis in Agmenellum quadruplicatum.

When levulinic acid was added to a growing culture of the cyanobacterium (blue-green alga) Agmenellum quadruplicatum PR-6, delta-aminoelevulinic acid accumulated in the medium and chlorophyll a synthesis and cell growth were inhibited, but there was a small amount of c-phycocyanin synthesis. The amount of delta-aminolevulinic acid produced in the treated culture did not fully account for the amount of pigment synthesized in the untreated control. Levulinic acid and either sodium nitrate or ammonium chloride were added to nitrogen-starved cultures of PR-6, and delta-aminolevulinic acid production and chlorophyll a and c-phycocyanin content were monitored. When ammonium chloride was added as a nitrogen source after nitrogen starvation, the cells recovered more rapidly than when sodium nitrate was added as a nitrogen source. In cultures recovering from nitrogen starvation, synthesis of c-phycocyanin occurred before synthesis of chlorophyll a.

Aminolevulinic Acid↗
PubMed2005

Industry research on the use and effects of levulinic acid: a case study in cigarette additives.

Public health officials and tobacco researchers have raised concerns about the possible contributions of additives to the toxicity of cigarettes. However, little attention has been given to the process whereby additives promote initiation and addiction. Levulinic acid is a known cigarette additive. Review of internal tobacco industry documents indicates that levulinic acid was used to increase nicotine yields while enhancing perceptions of smoothness and mildness. Levulinic acid reduces the pH of cigarette smoke and desensitizes the upper respiratory tract, increasing the potential for cigarette smoke to be inhaled deeper into the lungs. Levulinic acid also may enhance the binding of nicotine to neurons that ordinarily would be unresponsive to nicotine. These findings held particular interest in the internal development of ultralight and so-called reduced-exposure cigarette prototypes. Industry studies found significantly increased peak plasma nicotine levels in smokers of ultralight cigarettes following addition of levulinic acid. Further, internal studies observed changes in mainstream and sidestream smoke composition that may present increased health risks. The use of levulinic acid illustrates the need for regulatory authority over tobacco products as well as better understanding of the role of additives in cigarettes and other tobacco products.

Enzyme Inhibitors↗
PubMed2005

Synthesis and evaluation of 4-substituted semicarbazones of levulinic acid for anticonvulsant activity.

OBJECTIVE: A series of 4-aryl substituted semicarbazones of levulinic acid (4-oxo pentanoic acid) was designed and synthesized to meet the structural requirements essential for anticonvulsant activity. METHODS: All the compounds were evaluated for anticonvulsant activity. Anticonvulsant activity was determined after intraperitoneal (i.p.) administration to mice by maximal electroshock (MES) and subcutaneous metrazol (ScMet) induced seizure methods and minimal motor impairment was determined by rotorod test. RESULTS: A majority of the compounds exhibited significant anticonvulsant activity after intraperitoneal administration. In the present study 4-(4'-fluoro phenyl) levulinic acid semicarbazone emerged as the most active molecule, showing broad spectrum of activity with low neurotoxicity. Unsubstituted levulinic acid semicarbazone was found to be inactive in all the screens. CONCLUSION: The results obtained validate the hypothesis that presence of an aryl group near the semicarbazone moiety is essential for anticonvulsant activity. The results also indicate that the hydrophilic-hydrophobic site can accommodate hydrophilic groups.

Animals↗
PubMed2006

Levulinic acid production from wheat straw.

Studies were carried out on the effects of temperature, acid concentration, liquid:solid ratio and reaction time on levulinic acid production from wheat straw using response surface methodology. The P-value of the coefficient for acid concentration was 0.0002, suggesting that this was highly significant. The quadratic effects of temperature and liquid:solid ratio were also significant and their P-values were <0.0001 and 0.0027, respectively. The coefficient determination (R(2)) was good for the second-order model. The optimal conditions for levulinic acid production from wheat straw were 209.3 degrees C, 3.5% acid concentration, 15.6 liquid:solid ratio and 37.6 min of reaction time resulted 19.86% yield.

China↗
PubMed1983

Determinations of tiodazosin and levulinic acid from tablets by high-performance liquid chromatography.

Specific assays of tiodazosin and levulinic acid from tablet preparations were developed using high-performance liquid chromatography. Tiodazosin was determined with acetonitrile 50% (v/v) in pH 5.7 acetate buffer on a 300 X 3.9-mm i.d. microparticulate C-18 column using 254 nm detection with butylparaben as the internal standard. Levulinic acid was determined at 280 nm with 1 N acetic acid on a 300 X 3.9-mm i.d. microparticulate phenyl column using an external standard. The assays were run sequentially. The relative standard deviations of sample variability (2 sigma, n = 6) and recoveries from synthetic preparation were +/- 1.6 and approximately 95%, respectively, for both assays.

Chemistry, Pharmaceutical↗
PubMedDate not supplied

Production and characterization of poly-beta-hydroxyalkanoate copolymers from Burkholderia cepacia utilizing xylose and levulinic acid.

Poly(beta-hydroxybutyrate-co-beta-hydroxyvalerate) (P(3HB-co-3HV)) copolymers were prepared via shake-flask fermentations of Burkholderia cepacia (formerly Pseudomonas cepacia) containing 2.2% (w/v) xylose and concentrations of levulinic acid ranging from 0.07% to 0.67% (w/v). Periodic harvest of shake-flask cultures from 48 to 92 h post-inoculation yielded 4.4-5.3 g/L of dry cell biomass, containing 42-56% (w/w) P(3HB-co-3HV), with optimal product yield occurring between 66 and 74 h. Growth and PHA accumulation enhancement were observed with concentrations of levulinic acid from 0.07 to 0.52% (w/v), producing dry cell biomass and P(3HB-co-3HV) yields of 9.5 and 4.2 g/L, respectively, at the 0.52% (w/v) concentration of levulinic acid. Representative samples were subjected to compositional analysis by 300 MHz 1H and 150 MHz 13C NMR, indicating that these random copolymers contained between 0.8 and 61 mol % 3-hydroxyvalerate (3HV). Solvent-cast film samples were characterized by differential scanning calorimetry, which demonstrated melting temperatures (Tm) to decrease in a pseudoeutectic fashion from 174.3 degrees C (0.8 mol % 3HV) to a minimum of 154.2 degrees C (25 mol % 3HV) and the glass transition temperatures (Tg) to decrease linearly from 2.1 to -11.9 degrees C as a function of increasing mol % 3HV. Thermogravimetric analysis of the copolymer series showed the temperature for onset of thermal decomposition (T(decomp)) to vary as a function of mol % 3HV from 273.4 to 225.5 degrees C. Intrinsic viscosities (eta) varied from 3.2 to 5.4 dL/g, as determined by dilute solution viscometry. Viscosity average molecular weights (Mv) of the copolymers were determined to range from 469 to 919 kDa, indicating that these P(3HB-co-3HV) copolymers are of sufficient molecular mass for commercial application.

Alkanes↗
PubMed1987

A chronobiological study of delta-amino levulinic acid urinary excretion.

Determination of urinary delta-amino levulinic acid (ALA) is now systematically used in occupational health to detect an excessive exposure to lead in professionally exposed workers. However, to determine whether circadian changes of the urinary excretion of ALA alter the significance of the test, we quantified the ALA levels in the urine of 19 healthy young adults. Urine samples were taken every 3 hr between 0700 and 2300 hr and ALA levels were determined by a spectrocolorimetric method. The data indicated that the 24-hr mean ALA level was: 1.81 mg/g creatinine. The peak values (2.24 +/- 0.24) were obtained between 1400 and 1700 hr whereas the lowest ALA levels were found between 2200 and 0300 hr. Cosinor analysis revealed a significant circadian rhythm while no significant difference could be found according to sex. Possible explanations of our findings are discussed.

Adult↗
PubMed1981

Catabolism of [1-C]levulinic Acid by etiolated and greening barley leaves.

Levulinic acid (LA), a competitive inhibitor of delta-aminolevulinic acid (ALA) dehydratase (EC 4.2.1.24), has been used extensively in the study of ALA formation during greening. When [1-(14)C]LA is administered to etiolated barley (Hordeum vulgare L. var. Larker) shoots in darkness, (14)CO(2) is evolved. This process is accelerated when such tissues are incubated with 2 millimolar ALA or placed under continuous illumination. Label from the C-1 of LA becomes incorporated into organic acids, amino acids, sugars, lipids, and proteins during a 4-hour incubation in darkness or in the light. This metabolism is discussed in relation to the use of LA as a tool in the study of chlorophyll synthesis in higher plants.

Journal Article↗
PubMed2006

Parallel pore and surface diffusion of levulinic acid in basic polymeric adsorbents.

The equilibrium and kinetics of levulinic acid (LA) adsorption on two basic polymeric adsorbents, 335 (highly porous gel) and D315 (macroreticular), were investigated. Experimental adsorption rates in batch stirred vessels under a variety of operating conditions were described successfully by the parallel pore and surface diffusion model taking into account external mass transfer and nonlinear Toth isotherm. The film-pore diffusion model was matched with the rate data and the resulting apparent pore diffusivities were strongly concentration-dependent and approached to a constant value for 335 adsorbent. Thus, the constant value was taken as the accurate pore diffusivity, while the pore diffusivity in D315 was estimated from the particle porosity. The surface diffusivities decreased with increasing initial bulk concentration for both adsorbents. The inverse concentration dependence was correlated reasonably well to the change of isosteric heat of adsorption as amount adsorbed.

Adsorption↗