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PubMed1998

4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound prenyltransferase.

Geranyldiphosphate:4-hydroxybenzoate 3-geranyltransferase is a regulatory enzyme in the biosynthesis of shikonin, a phytoalexin and pharmaceutical produced by cell cultures of Lithospermum erythrorhizon Sieb. et Zucc. In Linsmaier-Skoog medium, the activity of this enzyme could be enhanced more than 200-fold by addition of methyl jasmonate, and this culture material was used for the solubilization and purification of the enzyme. Of various detergents examined, digitonin was the most suitable for the solubilization of the enzyme. The solubilized enzyme was purified 800-fold by chromatography over diethylaminoethyl (DEAE)-Sephacel, Heparin-Sepharose, Reactive Green 19-Agarose, and Cholic Acid-Agarose. The purified enzyme required magnesium ions as cofactor and was highly specific for geranyldiphosphate (GPP) and 4-hydroxybenzoate (4HB) as substrates. The K(m) values for 4HB and GPP were calculated by the method of Lineweaver and Burk as 18.4 microM and 13.8 microM, respectively.

Acetates↗
PubMed1986

3-Hydroxybenzo[a]pyrene glucuronidation by cells: a direct fluorometric assay in culture medium.

A direct fluorometric assay for measuring the glucuronidation by cultured cells using 3-hydroxybenzo[a]pyrene (less than 1 microM) as substrate is described. The method is based on the different characteristics in the fluorescence spectra of 3-hydroxybenzo[a]pyrene and benzo[a]pyrene-3-glucuronide. The analytical procedure operates directly on the culture medium without extraction steps. The sensitivity of detection is 1 nmol glucuronide/1 mumol substrate.

Animals↗
PubMed1984

Stimulation of rat liver 4-hydroxybenzoate: polyprenyl transferase activity by a cytosolic protein factor; evidence for a polyprenyl pyrophosphate transport protein.

Rat liver postmicrosomal supernatant contains a factor which stimulates the 4-hydroxybenzoate:polyprenyl transferase activity of whole mitochondria and inner mitochondrial membrane fragments. The factor involved appears to be a heat stable, nondializable protein sensitive to tryptic hydrolysis and has been partially purified. Since this protein binds nonaprenyl pyrophosphate and stimulates its transport into mitochondria but shows no similar effect with 4-hydroxybenzoate, it is suggested that this protein also acts as an all trans polyprenyl pyrophosphate carrier protein.

Alkyl and Aryl Transferases↗
PubMed1976

The conversion of benzo(alpha)pyrene 4,5-oxide into 4-hydroxybenzo(alpha)pyrene in the presence of polyriboguanylic acid.

Incubation of benzo[alpha] pyrene 4,5-oxide with poly(G) in neutral aqueous ethanol resulted in the formation of covalent adducts and in the production of free 4-hydroxybenzo[alpha]pyrene. This phenol, which was identified by its UV spectral properties and by its chromatographic characteristics, was also formed but at a much slower rate when the epoxide was incubated with DNA or with GMP. Phenol formation was not detected when benzo[alpha]-pyrene 4,5-oxide was incubated for prolonged periods in the presence of poly(A), poly(C) or poly(U) or in the absence of nucleic acid. Formation of 4-hydroxybenzo[alpha] pyrene from the epoxide in the presence of poly(G) was not accompanied by detectable base modifications or by breakage of phosphodiester linkages.

Benzopyrenes↗
PubMed1992

Ubiquinone biosynthesis. Cloning of the genes coding for chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyl transferase from Escherichia coli.

Chorismate pyruvate-lyase activity was detected in extracts of Escherichia coli. 4-Hydroxybenzoate was identified as the product of the enzymatic reaction by chemical derivatization and GC-MS analysis. The ubiC gene, coding for the chorismate pyruvate-lyase, was cloned and sequenced. The molecular weight of the gene product was calculated as 18,776 Da and confirmed by expression of the protein in E. coli minicells. The ubiA gene, coding for the 4-hydroxybenzoate octaprenyl transferase, was identified by sequence homology and complementation of a ubiA- strain. It is located directly downstream of ubiC in a typical operon structure.

Alkyl and Aryl Transferases↗
PubMed1985

Tumorigenicity study of butyl and isobutyl p-hydroxybenzoates administered orally to mice.

Butyl p-hydroxybenzoate (n-BHB) and isobutyl p-hydroxybenzoate (i-BHB) were administered orally to ICR/Jcl mice at concentrations of 0.6 (maximum tolerated dose), 0.3 or 0.15% in the diet for up to 102 wk. Tumours were observed at various sites including the haematopoietic system, the lung and the soft tissue. However, at none of the sites did the tumour incidence or the time to death with tumours differ significantly from that in the untreated control group.

Administration, Oral↗
PubMed1996

Simultaneous determination of bromhexine hydrochloride and methyl and propyl p-hydroxybenzoate and determination of dextromethorphan hydrobromide in cough-cold syrup by high-performance liquid chromatography.

Liquid chromatographic methods were developed for the determination of bromhexine hydrochloride, methyl p-hydroxybenzoate and propyl p-hydroxybenzoate (method A) and dextromethorphan hydrobromide (method B) in cough-cold syrup formulations. Reversed-phase analytical columns (150 mm x 3.9 mm i.d.) were used with (A) C18 and (B) phenyl as stationary phases and mixtures of (A) acetonitrile and aqueous 15 mM triethylamine solution (43:57) and (B) methanol and aqueous 3% ammonium formate buffer solution (53:47) as mobile phases at a flow rate of 1.0 ml min-1. Both aqueous components were adjusted to pH 3.9. UV detection of analytes was at (A) 245 nm and (B) 278 nm. In both methods, the time required for an HPLC run giving good separations and recoveries was less than 8 min.

Antitussive Agents↗
PubMed2004

Cloning of a gene encoding 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. 10d.

Bordetella sp. 10d produces a novel dioxygenase catalyzing the meta-cleavage of 4-amino-3-hydroxybenzoic acid, 4-amino-3-hydroxybenzoate 2,3-dioxygenase (4A3HBA23D). A gene encoding 4A3HBA23D was cloned and named ahdA. The deduced amino acid sequence of ahdA showed 29.2-24.2% identities to those of prokaryotic and eukaryotic 3-hydoxybenzoate 3,4-dioxygenases in reported meta-cleavage dioxygenases. However, no identities were observed in the amino-terminal sequences of the first 29 amino acid residues. An ORF was found downstream of ahdA. The deduced amino acid sequence of the ORF showed identities to those of LysR family regulators involved in protocatechuate metabolism and contained motifs conserved in the regulators. On the basis of these results, the ORF was named ahdR encoding a putative LysR family regulator. The transcription start point of ahdA was localized 414-bp upstream of the start codon of ahdA. Two DNA-binding motifs of LysR family regulators were found upstream of the transcription start point. These observations suggest that a LysR family regulator encoded by ahdR regulates the expression of ahdA.

Amino Acid Motifs↗
PubMed1999

Role of mitochondrial membrane permeability transition in p-hydroxybenzoate ester-induced cytotoxicity in rat hepatocytes.

The relationship between mitochondrial membrane permeability transition (MPT) and the toxic effects of the alkyl esters of p-hydroxybenzoic acid (parabens) has been studied in mitochondria and hepatocytes isolated from rat liver. MPT has been proposed as a common final pathway in acute cell death through mitochondrial dysfunction. In isolated mitochondria, propyl-paraben (0.1 to 0.5 mM) in the presence of Ca2+ (50 microM) elicited a concentration-dependent induction of mitochondrial swelling dependent on MPT. This was prevented by pretreatment with a specific inhibitor of MPT, cyclosporin A (0.2 microM). For the other parabens tested, the induction of MPT depended on the relative elongation of alkyl side-chains in their molecular structure and was associated with the partition coefficients. In contrast, the induction caused by p-hydroxybenzoic acid was more potent than that of methyl- or ethyl-paraben. The pretreatment of freshly isolated hepatocytes with cyclosporin A (5 microM) and trifluoperazine (10 microM), which inhibit MPT in a synergistic manner, partially but not completely prevented propyl-paraben (1 mM; plus diazinon, 100 microM)-induced cell death, ATP loss, and decreased mitochondrial membrane potential. These results suggest that the onset of paraben-induced cytotoxicity is linked to mitochondrial failure dependent upon induction of MPT accompanied by the mitochondrial depolarization and depletion of cellular ATP through uncoupling of oxidative phosphorylation.

Animals↗
PubMed2001

Oxidation of p-hydroxybenzoic acid by Fenton's reagent.

Fenton's reagent has been shown to be a feasible technique to treat phenolic-type compounds present in a variety of food processing industry wastewaters. A model compound, p-hydroxybenzoic acid was oxidised by continuously pumping two solutions of ferrous iron and hydrogen peroxide. Typical operating variables like reagent feeding concentrations and flowrate, temperature and pH were studied. A mechanism of reactions based on the classical Fenton's chemistry was assumed, and computed concentration profiles of the parent compound, ferrous ion and dihydroxybenzene were compared to experimental results. The model qualitatively predicted the influence of several operating variables, however, calculated results suggested the presence of parallel routes of substrate elimination and/or a initiating rate constant with a higher value. The low efficiency of a well-known hydroxyl radical scavenger (tert-butyl alcohol) also supports the contribution of oxidising species different from the hydroxyl radical to substrate removal. Further evidence of the presence of reactions different from the hydroxyl radical oxidation was observed from comparison of the simultaneous Fenton's or UV/H2O2 oxidations of p-hydroxybenzoic acid, tyrosol and p-coumaric acid.

Chromatography, High Pressure Liquid↗
PubMed1998

Characterization of Bradyrhizobium japonicum pcaBDC genes involved in 4-hydroxybenzoate degradation.

The pca structural genes encode enzymes that participate in the conversion of protocatechuate to succinate and acetylcoenzyme A. A 3. 05-kb region of the Bradyrhizobium japonicum strain USDA110 genome has been characterized, which contains the pcaB, pcaD and pcaC genes. The predicted protein sequences of the three genes have extensive homologies with beta-carboxy-cis,cis-muconate cycloisomerase (PcaB), beta-ketodiapate enol-lactone hydrolase (PcaD), and gamma-carboxymuconolactone decarboxylase (PcaC), respectively, from Acinetobacter calcoaceticus and Pseudomonas putida. The DNA sequence revealed that the pca genes are probably arranged in a single transcriptional unit, pcaBDC, similar to that described in P. putida. A pcaB deletion mutant constructed by marker exchange mutagenesis lost the ability to use 4-hydroxybenzoate or protocatechuate as the only carbon source, demonstrating functionality of the characterized genes in catabolism of hydroxyaromatics by B. japonicum. Furthermore, 4-hydroxybenzoate and protocatechuate became toxic for the pcaB mutant, indicating that hydroxyaromatics catabolism serves both nutritional and detoxifying purposes.

Amino Acid Sequence↗
PubMed2000

Kinetics of p-hydroxybenzoic acid photodecomposition and ozonation in a batch reactor.

The decomposition of p-hydroxybenzoic acid, an important pollutant present in the wastewaters of the olive oil industry, has been carried out by a direct photolysis provided by a polychromatic UV radiation source, and by ozone. In both processes, the conversions obtained as a function of the operating variables (temperature, pH and ozone partial pressure in the ozonation process) are reported. In order to evaluate the radiation flow rate absorbed by the solutions in the photochemical process, the Line Source Spherical Emission Model is used. The application of this model to the experimental results provides the determination of the reaction quantum yields which values ranged between 8.62 and 81.43 l/einstein. In the ozonation process, the film theory allows to establish that the absorption process takes place in the fast and pseudo-first-order regime and the reaction is overall second-order, first-order with respect to both reactants, ozone and p-hydroxybenzoic acid. The rate constants are evaluated and vary between 0.18x10(5) and 29.9x10(5) l/mol s depending on the temperature and pH.

Absorption↗
PubMed2003

Determination of bifonazole in creams containing methyl- and propyl p-hydroxybenzoate by derivative spectrophotometric method.

A second order derivative spectrophotometric method for the determination of bifonazole in the presence of methyl- and propyl p-hydroxybenzoate as preservatives has been developed. The determination was performed in a 0.1 M HCl solution at 241.5 nm, a wavelength corresponding to the intersection of the second order derivative spectra (2D) of methyl- and propyl p-hydroxybenzoate with the axis (zero-crossing point). On the basis of the knowledge of acidity constants and solubility, as well as of the investigations of zero-order and 2D spectra of bifonazole and preservatives, these conditions were chosen as optimal ones. A calibration curve constructed for bifonazole concentrations ranging from 1.5 to 15 microg/ml had a correlation coefficient of 0.9998. Reliability and reproducibility of the method was checked by analyzing laboratory mixtures of bifonazole and preservatives (recovery 99.97-102.7%; RDS 0.48-1.46%). The proposed method was applied for the determination of bifonazole in a commercial cream formulation. The mean value of bifonazole obtained per 100 g cream was 1.029 g (102.9% of the labeled claim) with a RSD of 0.60%.

Antifungal Agents↗
PubMed2002

Optimization of alkylidene hydrazide based human glucagon receptor antagonists. Discovery of the highly potent and orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide.

Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-cyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure-metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC(50) = 2.3 nM, K(B) = 760 pM) and of the isolated rat receptor (IC(50) = 430 pM, K(B) = 380 pM). Glucagon-stimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (K(i) = 14 nM). This compound was orally available in dogs (F(po) = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.

Administration, Oral↗
PubMed2004

Improved tableting properties of p-hydroxybenzoic acid by water of crystallization: a molecular insight.

PURPOSE: To understand the influence of water in the crystal structure on the compaction properties of otherwise structurally similar crystals, p-hydroxybenzoic acid anhydrate (HA) and the monohydrate (HM) were used as model compounds. METHODS: Bulk powder of HM was prepared by exposing HA powder to 97% relative humidity at 23 degrees C. Each powder, HA or HM, was uniaxially compressed and triaxially decompressed under various pressures to form square-faced tablets. The tensile strength and porosity of the tablets were measured. RESULTS: Incorporation of water into the crystal lattice results in greater tablet strength and larger reduction in volume for HM crystals than for HA crystals. Both HA and HM crystals contain hydrogen-bonded, zigzag-shaped layers that lie parallel to the (401) plane. When HA crystals are compressed, the zigzag-shaped layers mechanically interlock, inhibiting slip and reducing plasticity. However, water molecules in the HM crystals assume a space-filling role, which increases the separation of the layers. This effect allows easier slip between layers and provides greater plasticity of HM crystals, which increases the interparticulate bonding area under the same compaction pressure. However, the water molecules in the HM crystals increase their lattice energy by forming a three-dimensional hydrogen-bonding network. The greater bonding strength that results is reflected in greater tensile strength of HM compacts at zero porosity. CONCLUSIONS: The presence of water molecules in the crystal structure of p-hydroxybenzoic acid facilitates plastic deformation of HM crystals, thereby enhancing their bonding strength and giving much stronger tablets than of HA crystals.

Chemical Phenomena↗
PubMed2001

Influence of nutritional and environmental factors on polysaccharide production by Azotobacter vinelandii cultured on 4-hydroxybenzoic acid.

The capacity of 4-hydroxybenzoic acid to support exopolysaccharide (EPS) biosynthesis was investigated. Carbon source concentration, nitrogen supplementation, and other nutritional and environmental factors were optimized to obtain maximal EPS recovery. Higher EPS yields were obtained in nitrogen-free media amended with 20-30 mM 4-hydroxybenzoic acid. In general, modifications in inorganic salt concentration did not alter EPS production, except in the case of magnesium ions. Increased levels of this cation were correlated to greater EPS yields. Production was strongly influenced by certain environmental factors. Optimal values of 34 degrees C, 80 rpm and neutral or slightly basic conditions were selected. Under these conditions, more than 25% of the carbon source supplied was converted to EPS and the production was improved about 42% in comparison to that observed in the initial media.

Azotobacter vinelandii↗
PubMed2002

Physiology of exopolysaccharide production by Azotobacter vinelandii from 4-hydroxybenzoic acid.

The relationship between exopolysaccharide (EPS) production by Azotobacter vinelandii ATCC 12837 from 4-hydroxybenzoic acid as sole carbon source and other physiological parameters was investigated. In relation to growth, Azotobacter needed more time in 4-hydroxybenzoic acid to reach levels of biomass similar to those obtained when sugars were used, although the phenolic compound led to a more extensive exponential phase. The encystment process was initiated after cells had grown for 24 h, in which small amounts of EPS were synthesized and poly-beta-hydroxybutyrate (PHB) accumulation began. Both polymers, EPS and PHB, showed a similar evolution with time, as well as the formation of cysts, which points out the existence of a relation between these parameters. This was corroborated by a statistical study, in which significant correlations (P<0.05) were observed when each parameter was compared to the two others.

Azotobacter vinelandii↗