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PubMed1986

Enhancement of aldehyde dehydrogenase activity in human and rat hepatocyte cultures by 3-methylcholanthrene.

Aldehyde dehydrogenase was measured in primary cultures of hepatocytes obtained with a two-step collagenase perfusion either from human hepatic tissue or from livers of Fisher rats. Basal enzyme activity declines gradually as a function of time in culture, but remains at all times higher when measured with propionaldehyde and NAD (P/NAD) than with benzaldehyde and NADP (B/NADP). Treatment of the cultures with 2 microM of 3-methylcholanthrene for four days significantly increased the B-NADP activity of human and rat hepatocytes (tenfold and eightfold respectively). In human hepatocytes 3-methylcholanthrene increases also the P/NAD activity, but to a lesser extent (twofold), compared to the B/NADP activity. Due to the significant enhancement of B/NADP activity in cultures of human and rat hepatocytes after application of 3-methylcholanthrene, the initial difference in the basal activity levels between the P/NAD and B/NADP forms diminishes or, in the case of human hepatocytes, is even inverted. These results show for the first time that aldehyde dehydrogenase activity is increased in cultured human hepatocytes. This biochemical property is preserved in human and rat hepatocyte cultures, despite the rather quick loss of the basal aldehyde dehydrogenase activity.

Adult↗
PubMed1991

Coordination geometry for cadmium in the catalytic zinc site of horse liver alcohol dehydrogenase: studies by PAC spectroscopy.

Active site substituted Cd(II) horse liver alcohol dehydrogenase has been studied by Perturbed Angular Correlation of Gamma rays Spectroscopy during turnover conditions for benzaldehyde and 4-trans-(N,N-dimethylamino)cinnamaldehyde. The ternary complex between alcohol dehydrogenase NAD+ and Cl-, and the binary complex between alcohol dehydrogenase and orthophenanthroline have also been studied. The Nuclear Quadrupole Interaction parameters have been interpreted in terms of different coordination geometries for Cd(II) in the catalytic zinc site of the enzyme. Calculation of the nuclear quadrupole interaction for cadmium in the catalytic site of the enzyme with and without coenzyme, based upon the four coordinated geometries determined from X-ray diffraction, agrees with the experimentally determined values. The ternary complexes between enzyme, NAD+ and either Cl- or trifluoroethanol and the binary complex between enzyme and orthophenanthroline have almost identical spectral parameters which are not consistent with a four coordinated geometry, but are consistent with a five coordinated geometry. The non-protein ligands for the ternary complex with trifluoroethanol are suggested to be an alkoxide group and a water molecule. The Nuclear Quadrupole Interaction parameters for the productive ternary complex between enzyme, NADH and an aldehyde is consistent with the four coordinated geometry predicted from X-ray diffraction data having the carbonyl group of the aldehyde substituting the water molecule as ligand to the metal.

Alcohol Dehydrogenase↗
PubMed1995

Flight initiations in Drosophila melanogaster are mediated by several distinct motor patterns.

We have monitored the patterns of activation of five muscles during flight initiation of Drosophila melanogaster: the tergotrochanteral muscle (a mesothoracic leg extensor), dorsal longitudinal muscles #3, #4 and #6 (wing depressors), and dorsal ventral muscle #Ic (a wing elevator). Stimulation of a pair of large descending interneurons, the giant fibers, activates these muscles in a stereotypic pattern and is thought to evoke escape flight initiation. To investigate the role of the giant fibers in coordinating flight initiation, we have compared the patterns of muscle activation evoked by giant fiber stimulation with those during flight initiations executed voluntarily and evoked by visual and olfactory stimuli. Visually elicited flight initiations exhibit patterns of muscle activation indistinguishable from those evoked by giant fiber stimulation. Olfactory-induced flight initiations exhibit patterns of muscle activation similar to those during voluntary flight initiations. Yet only some benzaldehyde-induced and voluntary flight initiations exhibit patterns of muscle activation similar to those evoked by giant fiber stimulation. These results indicate that visually elicited flight initiations are coordinated by the giant fiber circuit. By contrast, the giant fiber circuit alone cannot account for the patterns of muscle activation observed during the majority of olfactory-induced and voluntary flight initiations.

Animals↗
PubMed1991

Anaerobic degradation of toluene by pure cultures of denitrifying bacteria.

Several denitrifying Pseudomonas spp., isolated with various aromatic compounds, were tested for the ability to degrade toluene in the absence of molecular oxygen. Four out of seven strains were able to degrade toluene in the presence of N2O. More than 50% of the 14C from ring-labelled toluene was released as CO2, and up to 37% was assimilated into cell material. Furthermore it was demonstrated for two strains that they were able to grow on toluene as the sole carbon and energy source in the presence of N2O. Suspensions of cells pregrown on toluene degraded toluene, benzaldehyde or benzoate without a lag phase and without accumulation of intermediates. p-Cresol, p-hydroxybenzylalcohol, p-hydroxybenzaldehyde or p-hydroxybenzoate was degraded much slower or only after distinct lag times. In the presence of fluoroacetate [14C]toluene was transformed to [14C]benzoate, which suggests that anaerobic toluene degradation proceeds through oxidation of the methyl side chain to benzoate.

Anaerobiosis↗
PubMed1979

Microbial oxidation of methane and methanol: purification and properties of a heme-containing aldehyde dehydrogenase from Methylomonas methylovora.

Procedures for the purification of an aldehyde dehydrogenase from extracts of the obligate methylotroph, Methylomonas methylovora are described. The purified enzyme is homogeneous as judged from polyacrylamide gel electrophoresis. In the presence of an artificial electron acceptor (phenazine methosulfate), the purified enzyme catalyzes the oxidation of straight chain aldehydes (C1--C10 tested), aromatic aldehydes (benzaldehyde, salicylaldehyde), glyoxylate, and glyceraldehyde. Biological electron acceptors such as NAD+, NADP+, FAD, FMN, pyridoxal phosphate, and cytochrome c cannot act as electron carriers. The activity of the enzyme is inhibited by sulfhydryl agents [p-chloromercuribenzoate, N-ethylmaleimide and 5,5-dithiobis (2-nitrobenzoic acid)], cuprous chloride, and ferrour nitrate. The molecular weight of the enzyme as estimated by gel filtration is approximately 45000 and the subunit size determined by sodium dodecyl sulfate-gel electrophoresis is approximately 23000. The purified enzyme is light brown and has an absorption peak at 410 nm. Reduction of enzyme with sodium dithionite or aldehyde substrate resulted in the appearance of peaks at 523 nm and 552nm. These results suggest that the enzyme is a hemoprotein. There was no evidence that flavins were present as prosthetic group. The amino acid composition of the enzyme is also presented.

Aldehyde Oxidoreductases↗
PubMed1978

Alcohol-oxidizing enzymes in 13 Drosophila species.

Starch and polyacrylamide gel electrophoresis were used to ascertain the substrate specificities of alcohol-oxidizing enzymes in 13 Drosophila species. The substrates used were a variety of long- and short-chain aliphatic alcohols, one aromatic alcohol, and benzaldehyde. Only one enzyme (product of a single-gene locus) showed significant NAD+-dependent alcohol dehydrogenase activity with short-chain aliphatic alcohols. The 13 species, belonging to four different Drosophila groups, all showed a similar complement of alcohol-oxidizing enzymes, although differences in electrophoretic mobility and in levels of activity existed from species to species. These findings are relevant to the adaptation of Drosophila to alcohol environments.

Alcohol Oxidoreductases↗
PubMed1995

The bioavailability and dose dependency of the deuterated anti-tumour agent 4,6-benzylidene-d1-D-glucose in mice and rats.

The benzaldehyde derivative 4,6-benzylidene-D-glucose (BG) induces an inhibition of protein synthesis at otherwise non-toxic doses in cells grown in vitro. To increase the biological effect of BG, the hydrogen in the formyl group was exchanged with deuterium, resulting in 4,6-benzylidene-d1-D-glucose (P-1013). In this study we compared the bioavailability of BG and P-1013, since both intraperitoneal and, especially, oral administration of the drugs would be a great advantage. We also examined whether or not P-1013 displays dose-dependent pharmacokinetics. Pharmacokinetics were studied by analysing plasma samples using reversed-phase high-performance liquid chromatography (HPLC). P-1013 was given at four different doses i.v. (60, 120, 145 and 230 mg/kg) and p.o. (60, 120, 170 and 230 mg/kg) to female Bom:NMRI-nu mice. The bioavailability was more than 50% for all doses. The results also indicate that P-1013 shows linear pharmacokinetics, with no change being observed in the half-life (t1/2) with increasing dose and only a slightly more than proportional increase in the area under the concentration-time curve (AUC) occurring with increasing dose. A doubling in dose resulted in a 2.2-fold increase in the AUC. P-1013 and BG were also given i.v., p.o. and i.p. to female nu/nu-BALB/cABom mice and male Wistar rats. A high degree of bioavailability was found in both species, with 55-100% of the delivered dose being absorbed. Deuteration of BG does not seem to alter its bioavailability, as we found the same bioavailability for P-1013 as for BG. We conclude that the pharmacokinetics of P-1013 does not prevent its use as a cancer treatment drug given orally.

Administration, Oral↗
PubMed1994

Binding of carbohydrates to solid supports, Part 2: Reaction of sugar hydrazones with isothiocyanate-substituted polystyrene.

The binding of sugars to a polymer support as thiosemicarbazones has been investigated as a means of immobilizing glycans. Hydrazones of glucose and N-acetylglucosamine were prepared by reaction with hydrazine hydrate, and successfully reacted with isothiocyanate-substituted polystyrene by incubation at room temperature and neutral pH. The binding was efficient and stable in aqueous buffers over a range of pH conditions. The bound sugars were recovered in moderate yield by treatment of the beads with hydrazine hydrate, benzaldehyde or acetone. Direct binding of reducing sugars to thiosemicarbazide-substituted polystyrene was not successful because of the unfavourable thermodynamics.

Binding Sites↗
PubMed1976

[Studies on mushroom flavours. 1. Organoleptic significance of constituents of the cultivated mushroom, agaricus bisporus].

The flavour of Agaricus bisporus was studied by comparing the results obtained in chemical and organoleptic analysis of the same extract. The natural (-)-form of 1-octen-3-ol had a stronger flavour than the (+)-form and was the most important aroma component. Nucleotides, amino-acids and carbohydrates also contributed significantly. Benzaldehyde, benzyl alcohol, 1-octen-3-one, n-butyric and isovaleric acids as well as low-boiling volatiles contributed less to the flavour. A synergistic effect of nucleotides, carbohydrates and (-1-octen-3-ol on the flavour was not observed.

Agaricales↗
PubMed1992

Olfactory responses of adult Amblyomma hebraeum and A. variegatum (Acari: Ixodidae) to attractant chemicals in laboratory tests.

Unfed adults of the African ticks, Amblyomma hebraeum Koch and A. variegatum (Fabricius), important vectors of human and animal diseases, were exposed to volatile compounds in an olfactometer in efforts to identify both tick-produced or synthetic chemicals capable of eliciting an attraction response. A formula, relative efficacy of attraction, was devised for comparison of responses between species and sexes to a particular test stimulus, or within a homogeneous population to different stimuli. Adults of both species responded strongly to known tick-pheromone constituents, nonanoic acid, methyl salicylate, 2.6-dichlorophenol and benzyl alcohol, as well as to a commercially produced antiseptic, TCP (Pfizer), and its major components, chlorinated and iodinated phenols. Benzaldehyde, a proposed tick-pheromone component, and heptadecane, not known from ticks, were markedly attractive to adults of A. hebraeum but not to those of A. variegatum. Males of the former species, but neither conspecific females not either sex of the latter species, responded significantly to salicylaldehyde (known from males of four species of ticks, including A. variegatum). o-nitrophenol, a major component of the aggregation-attachment pheromone of males of both A. variegatum and A hebraeum and a proven long-range attractant for them in the field, was only partially attractive to either species in the olfactometer. Neither species was attracted to 2-methylpropanoic acid, previously identified in volatile effluents form feeding male A. hebraeum. It is concluded that these important disease vectors respond positively to a variety of volatile chemicals, which may conceivably be used to attract them to traps, animals or acaricides in efforts to control ticks or the diseases they transmit.

Animals↗
PubMed1989

Pharmacodynamics of benzyl chloride in rats.

In today's world of high industrialization, toxicity and pollution have become common terms of references. Both laymen and experts are becoming increasingly concerned about various health hazards created by occupational and industrial wastes dumped in and around public places. Benzyl chloride (BCl) was one of the chemicals dumped by Hooker Chemicals in Love Canal, N.Y. Benzyl chloride (BCl) is extensively used in industry in the manufacture of dyes, perfumes, resins, and synthetic tannins. It has been found at various dump sites and industrial wastes, which has led to potential hazards to health. This study was conducted to investigate the pharmacodynamics of BCl in rats. Rats were given 14C-BCl in corn oil by gavage. The peak plasma level was reached at 30 min and began to decline. BCl elimination pattern follows a two compartment model. The distribution half-life (alpha-phase) was 1.3 hr while the half-life of elimination (beta-phase) was 58.53 hr. Distribution studies after 48 hr of BCl administration revealed that the concentration of radioisotopes was highest in the stomach, gastric content, ileum, and duodenum followed by liver, adrenal, bone marrow, whole blood, pancreas, lung, esophagus, skin, kidney, heart, thymus, fat, testes, spleen, brain, and carcass. Approximately 76% of the initial dose was excreted by kidney during the 72 hr studies. About 7% was detected in expired air as 14CO2, while less than 1.3% was present as 14C-BCl or 14C-BCl metabolites in expired air during 72 hr. Metabolism studies revealed that S-benzyl-N-acetyl cysteine, benzyl alcohol, and benzaldehyde were the metabolites present in the urine.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMedDate not supplied

Mitochondrial uncoupling agents. Effects on membrane permeability of molluscan neurons.

Agents which uncouple oxidative phosphorylation in mitochondria were applied to identified neurons in an isolated ganglion of the marine mollusc Navanax inermis. Aromatic monocarboxylic acids, acetanilides, benzamides, benzaldehydes and phenols all caused a rapid, reversible, dose-dependent increase in the membrane potential and conductance of the neurons tested. These events were due primarily to an increase in the membrane's conductance to potassium, relative to chloride. All active compounds also produced a reversible, dose-dependent decrease in the permeability of alkali-cations relative to potassium. The relative activity of congeners in each group of substances was directly correlated with the octanol-water partition coefficients of the various compounds, indicating that hydrophobicity was important in determining drug effect and suggesting that steric requirements were minimal. The results suggest that the observed changes in membrane electrical properties and cation selectivity are due to an increase in the membrane's anionic field strength caused by the hydrophobic interaction of anionic and nonionic agents with the neuronal membrane.

Animals↗
PubMed1981

Evaluation of models for the mechanism of action of 4-hydroxyphenylpyruvate dioxygenase.

3-Hydroxyphenylpyruvic acid was oxygenated with various complexes of oxygen with Fe2+, superoxide ion, hydroperoxide anion, triplet and singlet oxygen. Oxidation occurred giving varying amounts of the 4-hydroxy derivatives of benzaldehyde, benzoic acid, phenol, phenylacetic acid and 4-carboxymethylquinone, but no homogentisic acid. 4-Hydroxyphenylperacetic acid was prepared and shown not to undergo self-oxidation. Its ferrous salt decomposed to 4-hydroxybenzyl alcohol. It is concluded that the alpha-keto carboxylic function is the site of oxygenation in the enzyme process and that a trioxalanone rather than a peracid intermediate may be implicated.

4-Hydroxyphenylpyruvate Dioxygenase↗
PubMed1977

Benzoyl cyanide in the defensive secretion of polydesmoid millipeds.

A novel cyanogenetic compound benzoyl cyanide, was isolated from the defensive secretion of 3 polydesmoid millipeds (Pseudopolydesmus seratus, Apheloria corrugata and A. trimaculata). The secretion of the 3 species also contains mandelonitrile and benzaldehyde, and that of P. serratus contains mandelonitrile benzoate, benzoic acid, isovaleric acid, myristic acid and stearic acid.

Animals↗
PubMed1995

Evaluation of olfactory function by topographic EEG analysis in patients with Parkinson's disease.

Olfactory function impairment has been observed in patients with idiopathic Parkinson's disease (PD) using psychophysical procedures. In this study, an electrophysiological technique based on spectral analysis and topographic EEG mapping was used to evaluate EEG arousal response to olfactory stimulation in ten normal subjects and ten PD patients in stage II according to Hoehn and Yahr's scale, all of whom had akinetic-rigid syndrome and were receiving chronic L-Dopa therapy. Olfactory function was stimulated using diluted benzaldehyde by means of an apparatus set up in our laboratory. Spontaneous and post-olfactory stimulus EEGs were recorded from 20 electrodes placed upon the scalp according to the Int. 10-20 System. Total EEG power (from 0.5 to 19.5 Hz) was evaluated over 10 sec. artefact-free epochs. An olfactory arousal reaction was detected in nine of the ten PD patients and was characterised by a significant decrease in total power similar to that observed in all of the 10 normal subjects; these variations in EEG were found in all but the anterior regions of the scalp. The use of this technique does not seem to reveal any clear alteration in the olfactory function of PD patients.

Aged↗
PubMed1990

New prostaglandin synthetase inhibitors--di-and triphenylacrylonitriles.

16 triphenylacrylonitriles (TPE) or diphenylacrylonitriles (DPE) were synthesized by condensation of various benzophenones or benzaldehydes with various phenylacetonitriles. The pharmacological potency of these compounds was studied by incubation of bovine seminal vesicle microsomes and PG-RIA. The results showed that the potency of inhibition of PG biosynthetase of DPE was stronger than that of TPE. Compounds with electron-releasing functional groups were proved to be more effective than those with electron-attracting groups. Compound DPE-9 was the most active one, the potency of which was 40 times stronger than that of naproxen. The structure of some compounds has been analysed by X-ray diffraction. The relationship between structure and activity was investigated by means of X-ray diffraction, UV and NMR.

Acrylonitrile↗
PubMed2002

Development of quantitative extraction method of amygdalin without enzymatic hydrolysis from tonin(Persicae Semen) by high performance liquid chromatography.

Tonin(Persicae Semen) is the herb medicine that contains amygdalin as a major ingredient. Amygdalin in water is decomposed into benzaldehyde, HCN, and glucose by emulsin, a hydrolysis enzyme in tonin. A useful and practical method for the optimum extraction condition of amygdalin without enzymatic hydrolysis is required. The extraction yield of amygdalin of natural formula tonin was 0.1% from crude powders, 1.4% from small pieces, 3.5% from half pieces and 2.4% from whole pieces. The extraction yield of amygdalin of outer shell-eliminated tonin was 0.3% from crude powders, 1.4% from small pieces, and 3.5% from half pieces and whole pieces respectively. The extraction yield of amygdalin was most high when using the size larger than half.

Amygdalin↗