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At least 19 recordsLinked to original sources
PubMed2001

Isolation and characterization of a veratrol:corrinoid protein methyl transferase from Acetobacterium dehalogenans.

From 3-methoxyphenol-grown cells of Acetobacterium dehalogenans, an inducible enzyme was purified that mediated the transfer of the methyl groups of veratrol (1,2-dimethoxybenzene) to a corrinoid protein enriched from the same cells. In this reaction, veratrol was converted via 2-methoxyphenol to 1,2-dihydroxybenzene. The veratrol:corrinoid protein methyl transferase, designated MTIver, had an apparent molecular mass of about 32 kDa. With respect to the N-terminal amino acid sequence and other characteristics, MTIver is different from the vanillate:corrinoid protein methyl transferase (MTIvan) isolated earlier from the same bacterium. For the methyl transfer from veratrol to tetrahydrofolate, two additional protein fractions were required, one of which contained a corrinoid protein. This protein was not identical with the corrinoid protein of the vanillate O-demethylase system. However, the latter corrinoid protein could also serve as methyl acceptor for the veratrol:corrinoid protein methyl transferase. MTIver catalyzed the demethylation of veratrol, 3,4-dimethoxybenzoate, 2-methoxyphenol, and 3-methoxyphenol. Vanillate (3-methoxy-4-hydroxybenzoate), 2-methoxybenzoate, or 4-methoxybenzoate could not serve as substrates.

Acetobacter↗
PubMed1986

Demethylation of Veratrole by Cytochrome P-450 in Streptomyces setonii.

The actinomycete Streptomyces setonii 75Vi2 demethylates vanillic acid and guaiacol to protocatechuic acid and catechol, respectively, and then metabolizes the products by the beta-ketoadipate pathway. UV spectroscopy showed that this strain could also metabolize veratrole (1,2-dimethoxybenzene). When grown in veratrole-containing media supplemented with 2,2'-dipyridyl to inhibit cleavage of the aromatic ring, S. setonii accumulated catechol, which was detected by both liquid chromatography and gas chromatography. Reduced cell extracts from veratrole-grown cultures, but not sodium succinate-grown cultures, produced a carbon monoxide difference spectrum with a peak at 450 nm that indicated the presence of soluble cytochrome P-450. Addition of veratrole or guaiacol to oxidized cell extracts from veratrole-grown cultures produced difference spectra that indicated that these compounds were substrates for cytochrome P-450. My results suggest that S. setonii produces a cytochrome P-450 that is involved in the demethylation of veratrole and guaiacol to catechol, which is then catabolized by the beta-ketoadipate pathway.

Journal Article↗
PubMed2005

Veratrol-O-demethylase of Acetobacterium dehalogenans: ATP-dependent reduction of the corrinoid protein.

The anaerobic veratrol O-demethylase mediates the transfer of the methyl group of the phenyl methyl ether veratrol to tetrahydrofolate. The primary methyl group acceptor is the cobalt of a corrinoid protein, which has to be in the +1 oxidation state to bind the methyl group. Due to the negative redox potential of the cob(II)/cob(I)alamin couple, autoxidation of the cobalt may accidentally occur. In this study, the reduction of the corrinoid to the superreduced [Co(I)] state was investigated. The ATP-dependent reduction of the corrinoid protein of the veratrol O-demethylase was shown to be dependent on titanium(III) citrate as electron donor and on an activating enzyme. In the presence of ATP, activating enzyme, and Ti(III), the redox potential versus the standard hydrogen electrode (E (SHE)) of the cob(II)alamin/cob(I)alamin couple in the corrinoid protein was determined to be -290 mV (pH 7.5), whereas E (SHE) at pH 7.5 was lower than -450 mV in the absence of either activating enzyme or ATP. ADP, AMP, or GTP could not replace ATP in the activation reaction. The ATP analogue adenosine-5'-(beta,gamma-imido)triphosphate (AMP-PNP, 2-4 mM) completely inhibited the corrinoid reduction in the presence of ATP (2 mM).

Acetobacterium↗
PubMed1983

Bacterial methylation of chlorinated phenols and guaiacols: formation of veratroles from guaiacols and high-molecular-weight chlorinated lignin.

Two strains of bacteria, provisionally assigned to the genus Arthrobacter, were shown to metabolize mono-, di-, tri-, and tetrachloroguaiacols and pentachlorophenol to the corresponding O-methyl compounds. Hydroxylated intermediates were formed only transiently, except for the synthesis by one strain of 3,4,5-trichlorosyringol from 3,4,5-trichloroguaiacol. Two isomeric trichloroveratroles and tetrachloroveratrole were formed by three of the strains from a high-molecular-weight chlorinated lignin isolated from kraft pulp mill bleach plant. The concentrations of methylated metabolites varied widely and did not appear to be correlated with degradation. The possible environmental consequences resulting from synthesis of these highly lipophilic substances are discussed briefly.

Journal Article↗
PubMed1989

The A-type potassium current: methoxybenzenes increase the rate of inactivation in snail neurons.

The effects of anisole (methoxybenzene) and veratrole (1,2-dimethoxybenzene) on the resting membrane potential (RMP), action potential (AP) and membrane potassium currents were investigated in snail neurons under current- and voltage-clamp conditions. Anisole (0.9-3 mM) scarcely influenced the AP, but it moderately depolarized the membrane and increased the neuronal excitability. Anisole accelerated the time-dependent inactivation of the A-current and decreased the time constant of the decay in a dose-dependent way (K1/2 = 1.2 mM). The potential-dependence of the steady-state activation or inactivation of the A-current was not influenced by anisole. An analysis of the Hill plot of anisole action on the time constant of decay of the A-current showed a one-to-two binding stoichiometry (nH = 2.1). Veratrole (2-8 mM) was effective similarly to anisole on the A-current, but proved less potent.

Action Potentials↗
PubMed1997

Identification of Components of the Oviposition Aggregation Pheromone of the Gregarious Desert Locust, Schistocerca gregaria (Forskal).

Acetophenone and veratrole have been identified as two major behaviourally active components of the oviposition aggregation pheromone of the desert locust, Schistocerca gregaria. These compounds were identified from the volatiles of egg pod froth using gas chromatography-electroantennographic (GC-EAD) and gas chromatography-mass spectrometric (GC-MS) analysis. Both compounds were shown to elicit aggregation of gravid females in oviposition bioassays; however, they do not act synergistically. Both acetophenone and veratrole individually at optimum doses induced about 70% egg laying, a value similar to that evoked with froth volatiles.

Journal Article↗
PubMed2006

Naive and conditioned responses of Culex pipiens pipiens biotype molestus (Diptera: Culicidae) to flower odors.

Flower odors are important signals for chemical communication between plants and flower visitors. Here, we studied the naive responses of Culex pipiens pipiens biotype molestus Forskal 1775 (Diptera: Culicidae) to typical flower odors and assessed the learning capacity of mosquitoes to floral volatiles. The odor compounds used in the bioassay, phenyl acetaldehyde, veratrole, and 2-methoxyphenol, are typically found in the floral odor of Silene otites (L.) Wibel, a plant that is pollinated by nectar-drinking mosquitoes and moths, and/or in other closely related Silene species. Wind tunnel bioassays with a mixture of these compounds revealed that attraction of mosquitoes to odors was positively correlated with time passed since the last feeding. In single component bioassays, mosquitoes showed strong innate responses to phenyl acetaldehyde and only moderate or weak responses to veratrole and 2-methoxyphenol. Furthermore, in comparison with naive mosquitoes, conditioned mosquitoes were significantly more attracted to the mixture and single volatiles. These results indicate that naive mosquitoes are effectively attracted by appropriate floral scent compounds and that learning can increase the attractiveness of these compounds.

Acetaldehyde↗
PubMed2006

Biotransformation enzymes in Cunninghamella blakesleeana (NCIM-687).

Presence of higher enzyme levels of aminopyrine N-demethylase, aniline hydroxylase and 11-beta hydroxylase activities were observed in Cunninghamella blakesleeana grown in potato-dextrose medium for 96 h. The enzyme activity preferred NADPH as a cofactor and showed inhibition with CO, indicating cytochrome P450 mediated reactions. A significant increase in aniline hydroxylase enzyme activity was observed when mycelia incubated in incubation medium containing different inducers (viz. camphor, cholesterol, naphthalene, veratrole, phenobarbital, n -hexadecane and ethyl alcohol) when compared with mycelia incubated in same way but in absence of inducers. Cunninghamella blakesleeana (NCIM 687) have shown the ability to degrade cholesterol, camphor and naphthalene when 96 h grown mycelia incubated in incubation medium containing these organic compounds.

Aminopyrine N-Demethylase↗
PubMed2006

Antifeedants in the feces of the pine weevil Hylobius abietis: identification and biological activity.

Egg-laying females of the pine weevil, Hylobius abietis (L.), regularly deposit feces adjacent to each egg. Egg cavities are gnawed in the bark of roots of recently dead conifer trees. After egg deposition, the cavity is sealed by feces and a plug of bark fragments. Root bark containing egg cavities with feces is avoided as food by pine weevils, which indicates the presence of natural antifeedants. Here we present the first results of the isolation and chemical analyses of antifeedant compounds in the feces of H. abietis. In feeding bioassays, methanol extracts of the feces revealed strong antifeedant properties. Methanol extracts were fractionated by medium-pressure liquid chromatography and the antifeedant effects were mainly found in the fractions of highest polarity. Volatile compounds in the active fractions were identified by gas chromatography-mass spectrometry (GC-MS) and the nonvolatile compounds were characterized by pyrolysis-GC-MS. Based on mass spectra, a number of compounds with various chemical structures were selected to be tested for their antifeedant properties. Antifeedant effects were found among compounds apparently originating from lignin: e.g., a methylanisol, guaiacol, veratrol, dihydroxybenzenes, and dihydroconiferyl alcohol. A weak effect by fatty acid derivatives was found. The types of naturally occurring antifeedant compounds identified in this study may become useful for the protection of planted conifer seedlings against damage by H. abietis.

Animals↗
PubMed2006

Postpollination changes in floral odor in Silene latifolia: adaptive mechanisms for seed-predator avoidance?

Floral odor is a key trait for pollinator attraction in many plants, but may also direct antagonists like herbivores to flowers. In this study, we examined how floral scent changes after pollination in Silene latifolia, which has a specialized relationship with the seed predator Hadena bicruris. We found an overall decrease in total scent emission and considerable changes in relative amounts of scent compounds after pollination. Lilac aldehydes A and B as well as veratrole contributed most to the decrease in scent emission. These three compounds are known to be key signals for the attraction of H. bicruris to the flowers. A specific downregulation of these compounds may increase the reproductive success of the plant by reducing seed predation after pollination.

Animals↗
PubMed2003

Wings and legs are production sites for the desert locust courtship-inhibition pheromone, phenylacetonitrile.

Mature gregarious male desert locusts, Schistocerca gregaria, emit the courtship inhibition pheromone phenylacetonitrile. Wings and legs, in particular the fore wings, have been identified as the main releasing sites. Abdomen and head emit only trace amounts of this pheromone. In contrast veratrole, another typical component of male volatiles, is emitted by all body parts. Epidermal gland cells in the identified phenylacetonitrile releasing appendages are the putative sites of its biosynthesis. Incubation of these body parts in the presence of (14)C-phenylalanine results in the production of (14)C-phenylacetonitrile. Some of the phenylacetonitrile appears to be degraded to HCN and benzaldehyde presumably enhancing the repellent character of phenylacetonitrile. HCN is only detectable in volatiles of mature gregarious male desert locusts. Possible advantages of the observed distribution of the phenylacetonitrile release sites and of the cyanogenesis in relation to mating behaviour are discussed.

Acetonitriles↗