Streptomyces setonii: catabolism of vanillic acid via guaiacol and catechol

1981 ◽  
Vol 27 (6) ◽  
pp. 636-638 ◽  
Author(s):  
Anthony L. Pometto III ◽  
John B. Sutherland ◽  
Don L. Crawford
Keyword(s):  
Vanillic Acid ◽  
Protocatechuic Acid ◽  
Carbon Sources ◽  
Uv Spectra ◽  
Ring Cleavage ◽  
Uv Spectrophotometry ◽  
Hydroxybenzoic Acid ◽  
Catechol 1,2 Dioxygenase ◽  
Cleavage Reactions ◽  
Layer Chromatography

Streptomyces setonii (strain 75Vi2) was grown at 45 °C in liquid media containing simple aromatic compounds as principal carbon sources. Thin-layer chromatography, UV spectrophotometry, and gas chromatography were used to show that S. setonii converted benzoic acid, guaiacol, and vanillic acid to catechol; p-hydroxybenzoic acid to protocatechuic acid; and m-hydroxybenzoic acid to gentisic acid. Presence of the ring-cleavage enzymes catechol 1,2-dioxygenase, protocatechuate 3,4-dioxygenase, and gentisate 1,2-dioxygenase was shown both by O2 uptake in ring-cleavage reactions catalyzed by cell-free extracts and by changes in UV spectra that indicated the presence of specific ring-cleavage products. A unique feature of this strain was its catabolism of vanillic acid by way of guaiacol and catechol, using a pathway that had not been confirmed previously.

Metabolism of cinnamic, p-coumaric, and ferulic acids by Streptomyces setonii

1983 ◽  
Vol 29 (10) ◽  
pp. 1253-1257 ◽  
Author(s):  
John B. Sutherland ◽  
Don L. Crawford ◽  
Anthony L. Pometto III
Keyword(s):  
Ferulic Acid ◽  
Yeast Extract ◽  
Cinnamic Acid ◽  
Vanillic Acid ◽  
Protocatechuic Acid ◽  
Oxygen Electrode ◽  
Ring Cleavage ◽  
Initial Growth ◽  
Coumaric Acid ◽  
Catechol 1,2 Dioxygenase

Streptomyces setonii strain 75Vi2 was grown at 45 °C in liquid media containing yeast extract and trans-cinnamic acid, p-coumaric acid, ferulic acid, or vanillin. Gas chromatography, thin-layer chromatography, and mass spectrometry showed that cinnamic acid was catabolized via benzaldehyde, benzoic acid, and catechol; p-coumaric acid was catabolized via p-hydroxybenzaldehyde, p-hydroxybenzoic acid, and protocatechuic acid; ferulic acid was catabolized via vanillin, vanillic acid, and protocatechuic acid. When vanillin was used as the initial growth substrate, it was catabolized via vanillic acid, guaiacol, and catechol. The inducible ring-cleavage dioxygenases catechol 1,2-dioxygenase and protocatechuate 3,4-dioxygenase were detected with an oxygen electrode in cell-free extracts of cultures grown in media with aromatic growth substrates and yeast extract.

DEGRADATION OF AROMATIC AMINO ACIDS BY FUNGI: I. FATE OF L-PHENYLALANINE IN SCHIZOPHYLLUM COMMUNE

1967 ◽  
Vol 45 (11) ◽  
pp. 1659-1665 ◽  
Author(s):  
Keith Moore ◽  
G. H. N. Towers
Keyword(s):  
Amino Acids ◽  
Benzoic Acid ◽  
Protocatechuic Acid ◽  
Phenylacetic Acid ◽  
Schizophyllum Commune ◽  
Aromatic Amino Acids ◽  
Ring Cleavage ◽  
Hydroxybenzoic Acid ◽  
Phenyllactic Acid ◽  
Phenylalanine Metabolism

Growing cultures of Schizophyllum commune could produce 14CO2 from ring-labelled DL-phenylalanine-14C. Intermediates in the pathway of L-phenylalanine degradation prior to ring cleavage were shown to be cinnamic acid, benzoic acid, p-hydroxybenzoic acid, and protocatechuic acid. Phenylacetic acid and L(−)-β-phenyllactic acid were also identified as products of phenylalanine metabolism.

COUMARINS AND PHENOLIC ACIDS IN THE UREDOSPORES OF WHEAT STEM RUST

1957 ◽  
Vol 3 (6) ◽  
pp. 847-862 ◽  
Author(s):  
C. F. van Sumere ◽  
C. van Sumere-de Preter ◽  
L. C. Vining ◽  
G. A. Ledingham
Keyword(s):  
Ferulic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Stem Rust ◽  
Vanillic Acid ◽  
Protocatechuic Acid ◽  
Hydroxybenzoic Acid ◽  
Coumaric Acid ◽  
Wheat Stem Rust ◽  
Stimulation Of

A paper chromatographic method suitable for identification of the small amounts of coumarins and phenolic acids present in the uredospores of wheat stem rust was developed. By the use of the circular technique and a combination of three different solvent systems an adequate separation of all the substances was achieved. A preliminary development of the chromatogram with a solvent in which the test compounds were non-mobile facilitated identification and avoided the need for extensive preliminary fractionation of the extracts.Using this method the following compounds were identified in spore extracts: coumarin, umbelliferone, daphnetin, aesculetin, p-hydroxybenzoic acid, vanillic acid, protocatechuic acid, o-coumaric acid, p-coumaric acid, ferulic acid, and caffeic acid; coumarin, p-hydroxybenzoic acid, vanillic acid, protocatechuic acid, o-coumaric acid, and ferulic acid were also present as glycosides; in addition scopoletin, gallic acid, syringic acid, and sinapic acid were detected after hydrolysis and are assumed to be present only in a bound form.In order to obtain some information about the role of these substances in the physiology of wheat stem rust, uredospores were germinated by being floated en masse on dilute aqueous solutions. Of the compounds tested, indoleacetic acid, coumarin, o-coumaric acid, protocatechuic acid, umbelliferone, and daphnetin gave a marked stimulation of germination at concentrations of 10–200 μg./ml. Caffeic acid, vanillic acid, p-hydroxybenzoic acid, ferulic acid, and ferulic acid β-glucoside had little effect or were strongly inhibitory.The stimulation of germination is attributed to the counteraction of a self-inhibitor released from the spores, and the possible significance of the compounds on the physiology of the rust and the host–parasite relationship is discussed.

scholarly journals Kinetic modeling of anaerobic degradation of plant-derived aromatic mixtures by Rhodopseudomonas palustris

2021 ◽  
Vol 32 (2) ◽  
pp. 179-192
Author(s):  
Yanjun Ma ◽  
Timothy J. Donohue ◽  
Daniel R. Noguera
Keyword(s):  
Kinetic Modeling ◽  
Vanillic Acid ◽  
Aromatic Compounds ◽  
Rhodopseudomonas Palustris ◽  
Substrate Inhibition ◽  
Carbon Sources ◽  
Syringic Acid ◽  
Hydroxybenzoic Acid ◽  
Organic Substrates ◽  
Substrate Channeling

AbstractRhodopseudomonas palustris is a model microorganism for studying the anaerobic metabolism of aromatic compounds. While it is well documented which aromatics can serve as sole organic carbon sources, co-metabolism of other aromatics is poorly understood. This study used kinetic modeling to analyze the simultaneous degradation of aromatic compounds present in corn stover hydrolysates and model the co-metabolism of aromatics not known to support growth of R. palustris as sole organic substrates. The simulation predicted that p-coumaroyl amide and feruloyl amide were hydrolyzed to p-coumaric acid and ferulic acid, respectively, and further transformed via p-coumaroyl-CoA and feruloyl-CoA. The modeling also suggested that metabolism of p-hydroxyphenyl aromatics was slowed by substrate inhibition, whereas the transformation of guaiacyl aromatics was inhibited by their p-hydroxyphenyl counterparts. It also predicted that substrate channeling may occur during degradation of p-coumaroyl-CoA and feruloyl-CoA, resulting in no detectable accumulation of p-hydroxybenzaldehyde and vanillin, during the transformation of these CoA ligated compounds to p-hydroxybenzoic acid and vanillic acid, respectively. While the simulation correctly represented the known transformation of p-hydroxybenzoic acid via the benzoyl-CoA pathway, it also suggested co-metabolism of vanillic acid and syringic acid, which are known not to serve as photoheterotrophic growth substrate for R. palustris.

3,4-Dichlorobenzoic acid biodegradation by the Edwardsiella tarda: Effect of Some Growth Conditions

2020 ◽  
Vol 6 (1) ◽  
pp. 7-14
Author(s):  
Ali Alqudah ◽  
Waleed Jaafreh
Keyword(s):  
Cell Mass ◽  
Carbon Sources ◽  
Nitrogen Sources ◽  
Growth Conditions ◽  
Edwardsiella Tarda ◽  
Ring Cleavage ◽  
Bacterial Cells ◽  
Carbon And Nitrogen ◽  
Catechol 1,2 Dioxygenase ◽  
Degradation Ability

The biodegradation of 3,4-DiChlorobenzoic acid was investigated by using Edwardsiella tarda and it used 3,4-DCBA as sole carbon and energy source. Several concentrations of 3,4-D CBAs (1mM, 2mM ,3mM ,4mM and 5mM) were used. The highest rate of degradation of 3,4-D CBAs was obtained at a concentration (2mM). The experiments were included substrate concentration, temperature, pH, starvation, adaptation, carbon and nitrogen sources. The degradation ability was monitored through the release of chloride disappearance of the substrate and finally the growth of bacterial cells on that substrate. The optimal temperature and pH for the bacteria were 42ºC and 7.5, respectively. Adaptation of the cells on 3,4-DCBA for 48 hours and cells starvation for 24 hours and 48 hours increasing the initial degradation rate. The carbon sources affected the 3,4 –DCBA degradation differently from that on chloride and cell mass production. Nitrogen sources supplied (yeast extract, L-proline, casein, NH4, K-Nitrate, arginine, urea and glycine). Urea and casine caused a repression in 3,4-DCBA degradation. Catechol 1,2 dioxygenase activity was found to be present in cell free extracts suggesting that 3,4-DCBA is catabolized by ortho-ring cleavage pathway.

scholarly journals Angelica Stem: A Potential Low-Cost Source of Bioactive Phthalides and Phytosterols

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3065 ◽  
Author(s):  
Chengke Zhao ◽  
Yuan Jia ◽  
Fachuang Lu
Keyword(s):  
Ferulic Acid ◽  
Vanillic Acid ◽  
Aerial Part ◽  
Protocatechuic Acid ◽  
Low Cost ◽  
Multiple Reaction Monitoring ◽  
Agricultural Waste ◽  
Hydroxybenzoic Acid ◽  
Reaction Monitoring ◽  
Medical Plant

Chinese Angelica is a significant medical plant due to the various therapeutic constituents in its root; whereas the aerial part is considered worthless and often discarded as agricultural waste. In this work, phytochemicals from the stem were first systematically analyzed by means of GC–MS after derivatization and HPLC–MS/MS in multiple reaction monitoring (MRM) mode. Phthalides, ferulic acid, and coniferyl ferulate were detected in the stem; although their content is relatively low in comparison with the root. Some specific compounds, such as p-hydroxybenzoic acid, vanillic acid, protocatechuic acid, caffeic acid, 4-hydroxyphenyl-1, 2-ethanediol, thymol-β-d-glucopyranoside, etc. and a significant amount of phytosterols (1.36 mg/g stem, mainly β-sitosterol) were detected in the stem. The extracted oil from the stem contained a considerable amount of phthalides (48.5 mg/g), β-sitosterol (56.21 mg/g), and stigmasterol (14.03 mg/g); no other bioactive compounds were found that could be potentially used as pharmaceuticals or additives to healthcare food.

scholarly journals Metabolic Engineering of a Novel Muconic Acid Biosynthesis Pathway via 4-Hydroxybenzoic Acid in Escherichia coli

2015 ◽  
Vol 81 (23) ◽  
pp. 8037-8043 ◽  
Author(s):  
Sudeshna Sengupta ◽  
Sudhakar Jonnalagadda ◽  
Lakshani Goonewardena ◽  
Veeresh Juturu
Keyword(s):  
Escherichia Coli ◽  
Metabolic Engineering ◽  
Carbon Sources ◽  
Raw Material ◽  
Hydroxybenzoic Acid ◽  
Muconic Acid ◽  
Content Type ◽  
E Coli ◽  
Catechol 1,2 Dioxygenase ◽  
K 12

ABSTRACTcis,cis-Muconic acid (MA) is a commercially important raw material used in pharmaceuticals, functional resins, and agrochemicals. MA is also a potential platform chemical for the production of adipic acid (AA), terephthalic acid, caprolactam, and 1,6-hexanediol. A strain ofEscherichia coliK-12, BW25113, was genetically modified, and a novel nonnative metabolic pathway was introduced for the synthesis of MA from glucose. The proposed pathway converted chorismate from the aromatic amino acid pathway to MA via 4-hydroxybenzoic acid (PHB). Three nonnative genes,pobA,aroY, andcatA, coding for 4-hydroxybenzoate hydrolyase, protocatechuate decarboxylase, and catechol 1,2-dioxygenase, respectively, were functionally expressed inE. colito establish the MA biosynthetic pathway.E. colinative genesubiC,aroFFBR,aroE, andaroLwere overexpressed and the genesptsH,ptsI,crr, andpykFwere deleted from theE. coligenome in order to increase the precursors of the proposed MA pathway. The final engineeredE. colistrain produced nearly 170 mg/liter of MA from simple carbon sources in shake flask experiments. The proposed pathway was proved to be functionally active, and the strategy can be used for future metabolic engineering efforts for production of MA from renewable sugars.

Comparison of UV- and Derivative-Spectrophotometric and HPTLC UVDensitometric Methods for the Determination of Amrinone and Milrinone in Bulk Drugs

2020 ◽  
Vol 16 (3) ◽  
pp. 246-253
Author(s):  
Marcin Gackowski ◽  
Marcin Koba ◽  
Stefan Kruszewski
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
High Performance ◽  
Low Cost ◽  
Uv Spectra ◽  
Derivative Spectrophotometry ◽  
Therapeutic Monitoring ◽  
Bulk Drug ◽  
Layer Chromatography ◽  
Standard Solutions

Background: Spectrophotometry and thin layer chromatography have been commonly applied in pharmaceutical analysis for many years due to low cost, simplicity and short time of execution. Moreover, the latest modifications including automation of those methods have made them very effective and easy to perform, therefore, the new UV- and derivative spectrophotometry as well as high performance thin layer chromatography UV-densitometric (HPTLC) methods for the routine estimation of amrinone and milrinone in pharmaceutical formulation have been developed and compared in this work since European Pharmacopoeia 9.0 has yet incorporated in an analytical monograph a method for quantification of those compounds. Methods: For the first method the best conditions for quantification were achieved by measuring the lengths between two extrema (peak-to-peak amplitudes) 252 and 277 nm in UV spectra of standard solutions of amrinone and a signal at 288 nm of the first derivative spectra of standard solutions of milrinone. The linearity between D252-277 signal and concentration of amironone and 1D288 signal of milrinone in the same range of 5.0-25.0 μg ml/ml in DMSO:methanol (1:3 v/v) solutions presents the square correlation coefficient (r2) of 0,9997 and 0.9991, respectively. The second method was founded on HPTLC on silica plates, 1,4-dioxane:hexane (100:1.5) as a mobile phase and densitometric scanning at 252 nm for amrinone and at 271 nm for milrinone. Results: The assays were linear over the concentration range of 0,25-5.0 μg per spot (r2=0,9959) and 0,25-10.0 μg per spot (r2=0,9970) for amrinone and milrinone, respectively. The mean recoveries percentage were 99.81 and 100,34 for amrinone as well as 99,58 and 99.46 for milrinone, obtained with spectrophotometry and HPTLC, respectively. Conclusion: The comparison between two elaborated methods leads to the conclusion that UV and derivative spectrophotometry is more precise and gives better recovery, and that is why it should be applied for routine estimation of amrinone and milrinone in bulk drug, pharmaceutical forms and for therapeutic monitoring of the drug.

Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion

2005 ◽  
Vol 70 (12) ◽  
pp. 2075-2085 ◽  
Author(s):  
Jiří Kroutil ◽  
Klára Jeništová
Keyword(s):  
Fluoride Anion ◽  
Ring Cleavage ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Aziridine Ring ◽  
Cleavage Reactions ◽  
Derivatives Of ◽  
Fluoro Derivatives

Aziridine ring cleavage reactions of five N-nosylepimines (2-6) having D-talo, D-galacto, D-manno, and D-allo configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose 7-11 in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound 10.

scholarly journals Lupeol acetate as a potent antifungal compound against opportunistic human and phytopathogenic mold Macrophomina phaseolina

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Shabnam Javed ◽  
Zaid Mahmood ◽  
Khalid Mohammed Khan ◽  
Satyajit D. Sarker ◽  
Arshad Javaid ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Ethyl Acetate ◽  
Oleanolic Acid ◽  
Vanillic Acid ◽  
Fungal Biomass ◽  
Protocatechuic Acid ◽  
Methanolic Extract ◽  
Antifungal Compound ◽  
Chloroform Fraction ◽  
Lupeol Acetate

AbstractAntifungal activity of Monothecabuxifolia methanolic extract and its various fractions were assessed against Macrophominaphaseolina, a soil-borne fungal pathogen of more than 500 vegetal species as well as rare and emerging opportunistic human pathogen. Different concentrations of methanolic extract (3.125 to 200 mg mL−1) inhibited fungal biomass by 39–45%. Isolated n-hexane, chloroform and ethyl acetate fractions suppressed fungal biomass by 32–52%, 29–50% and 29–35%, respectively. Triterpenes lupeol and lupeol acetate (1, 2) were isolated from n-hexane while betulin, β-sitosterol, β-amyrin, oleanolic acid (3–6) were isolated from chloroform fraction. Vanillic acid, protocatechuic acid, kaempferol and quercetin (7–10) were isolated from the ethyl acetate fraction and identified using various spectroscopic techniques namely mass spectroscopy and NMR. Antifungal activity of different concentrations (0.0312 to 2 mg mL−1) of the isolated compounds was evaluated and compared with the activity of a broad spectrum fungicide mancozeb. Different concentrations of mencozeb reduced fungal biomass by 83–85%. Among the isolated compounds lupeol acetate (2) was found the highest antifungal against M.phaseolina followed by betulin (3), vanillic acid (7), protocatechuic acid (8), β-amyrin (5) and oleanolic acid (6) resulting in 79–81%, 77–79%, 74–79%, 67–72%, 68–71% and 68–71%, respectively. Rest of the compounds also showed considerable antifungal activity and reduced M.phaseolina biomass by 41–64%.

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