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 ferulic acid via 4-vinylguaiacol by Fusarium solani (Mart.) Sacc.

1986 ◽  
Vol 32 (6) ◽  
pp. 494-497 ◽  
Author(s):  
S. Nazareth ◽  
S. Mavinkurve
Keyword(s):  
Ferulic Acid ◽  
Aromatic Ring ◽  
Cinnamic Acid ◽  
Metabolic Pathway ◽  
Vanillic Acid ◽  
Fusarium Solani ◽  
Protocatechuic Acid ◽  
Pure Form ◽  
Coumaric Acid ◽  
Transient Intermediate

Fusarium solani (Mart.) Sacc. metabolizes ferulic acid to a transient intermediate, 4-vinylguaiacol, a compound hitherto not reported in the metabolic pathway of ferulic acid in fungi. The compound was isolated in pure form and identified spectrometrically. 4-Vinylguaiacol was further metabolized to vanillin, vanillic acid, and protocatechuic acid, followed by ortho cleavage of the aromatic ring. The organism was also found to catabolize eugenol and p-coumaric acid, but not cinnamic acid.

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.

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.

BIOSYNTHESIS OF PUNGENIN FROM C14-LABELLED COMPOUNDS BY COLORADO SPRUCE

1959 ◽  
Vol 37 (5) ◽  
pp. 1085-1100 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Cinnamic Acid ◽  
Mandelic Acid ◽  
Protocatechuic Acid ◽  
Phenylacetic Acid ◽  
Shikimic Acid ◽  
Coumaric Acid ◽  
Carbonyl Carbon ◽  
Phenyllactic Acid ◽  
Methyl Group ◽  
Picea Pungens

A number of C14-labelled compounds were fed to detached leafy twigs of Colorado spruce (Picea pungens Engelm.), and after a metabolic period of 24 hours the pungenin was isolated and the specified activities of the glucose moiety and the aglycone (3,4-dihydroxyacetophenone) were determined. In some instances the aglycone was degraded further to determine the C14 in the methyl and carbonyl carbons separately.Caffeic acid and L-phenylalanine were the best precursors of the aglycone; cinnamic acid, p-coumaric acid, phenyllactic acid, and shikimic acid were quite good. Sodium acetate was a poor precursor, and was converted to glucose more readily than to the aglycone. Compounds found to be very poor precursors include tyrosine, 3,4-dihydroxyphenylalanine, 3-hydroxytyramine, phenylacetic acid, mandelic acid, p-hydroxyphenylpyruvic acid, p-hydroxyphenyllactic acid, p-hydroxybenzoic acid, and protocatechuic acid. Cinnamic acid-α-C14 gave 3,4-dihydroxyacetophenone labelled chiefly in the methyl group, while cinnamic acid-β-C14, L-phenylalanine-β-C14, p-coumaric acid-β-C14, and caffeic acid-β-C14 formed 3,4-dihydroxyacetophenone labelled mainly in the carbonyl carbon. It appears that a phenylethanoid compound is formed by a process involving the loss of the terminal carbon of a phenylpropanoid compound.3,4-Dihydroxyacetophenone-carbonyl-C14 was fed to spruce twigs bearing new terminal growth; up to 20% was converted to pungenin but most of it formed unidentified compounds. It was a poor precursor of lignin, compared with cinnamic acid, and a poor precursor of glutamic acid, relative to acetate.

scholarly journals Anti-malarial Activity Of Phenolic Acids Is Structurally Related

2020 ◽  
Author(s):  
Prince A Fordjour ◽  
Jonathan P Adjimani ◽  
Bright Asare ◽  
Nancy O Duah-Quashie ◽  
Neils B Quashie
Keyword(s):  
Plasmodium Falciparum ◽  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Rosmarinic Acid ◽  
Protocatechuic Acid ◽  
Antimalarial Activity ◽  
Coumaric Acid

Abstract Background In the absence of an effective vaccine against malaria, chemotherapy remains a major option in the control of the disease. Then, the recent report of the emergence and spread of clones of Plasmodium falciparum resistant to available antimalarial drugs should be of concern as it poses a threat to disease control. Compounds whose pharmacological properties have been determined and touted for other disease can be investigated for antimalarial activity. Phenolic acids (polyphenols) have been reported to exhibit antioxidant, anticancer, anti-inflammatory, antiviral and antibiotic effects. However, information on their antimalarial activity is scanty. Phenolic acids are present in a variety of plant-based foods: mostly high in the skins and seeds of fruits as well as the leaves of vegetables. Systematic assessment of these compounds for antimalarial activity is therefore needed. Method Using the classical in vitro drug test, the antimalarial activities of five hydroxycinnamic acids, (caffeic acid, rosmarinic acid, chlorogenic acid, o-Coumaric acid and ferulic acid) and two hydroxybenzoic acids (gallic acid and protocatechuic acid) against 3D7 clones of Plasmodium falciparum was determined. Results Among the phenolic acids tested, caffeic acid and gallic acid were found to be the most effective, with mean IC 50 value of 17.73µg/ml and 26.59µg/ml respectively for three independent determinations. Protocatechuic acid had an IC 50 value of 30.08 µg/ml. Rosmarinic acid and chlorogenic acid, showed moderate antimalarial activities with IC 50 values of 103.59µg/ml and 105µg/ml respectively. The IC 50 values determined for ferulic acid and o-Coumaric acid were 93.36µg/ml and 82.23µg/ml respectively. Conclusion The outcome of this study suggest that natural occurring phenolic compounds have appreciable level of antimalarial activity which can be exploited for use through combination of actions/efforts including structural manipulation to attain an increase in their antimalarial effect. Eating of natural food products rich in these compounds could provide antimalarial prophylactic effect.

scholarly journals Biodegradation of lignin monomers and bioconversion of ferulic acid to vanillic acid by Paraburkholderia aromaticivorans AR20-38 isolated from Alpine forest soil

2021 ◽  
Vol 105 (7) ◽  
pp. 2967-2977
Author(s):  
Rosa Margesin ◽  
Georg Volgger ◽  
Andreas O. Wagner ◽  
Dechao Zhang ◽  
Caroline Poyntner
Keyword(s):  
Ferulic Acid ◽  
Vanillic Acid ◽  
Sole Carbon Source ◽  
Value Added ◽  
Syringic Acid ◽  
High Yield ◽  
Coumaric Acid ◽  
Degradation Study ◽  
Alpine Forest ◽  
Key Points

Abstract Lignin bio-valorization is an emerging field of applied biotechnology and has not yet been studied at low temperatures. Paraburkholderia aromaticivorans AR20-38 was examined for its potential to degrade six selected lignin monomers (syringic acid, p-coumaric acid, 4-hydroxybenzoic acid, ferulic acid, vanillic acid, benzoic acid) from different upper funneling aromatic pathways. The strain degraded four of these compounds at 10°C, 20°C, and 30°C; syringic acid and vanillic acid were not utilized as sole carbon source. The degradation of 5 mM and 10 mM ferulic acid was accompanied by the stable accumulation of high amounts of the value-added product vanillic acid (85–89% molar yield; 760 and 1540 mg l−1, respectively) over the whole temperature range tested. The presence of essential genes required for reactions in the upper funneling pathways was confirmed in the genome. This is the first report on biodegradation of lignin monomers and the stable vanillic acid production at low and moderate temperatures by P. aromaticivorans. Key points • Paraburkholderia aromaticivorans AR20-38 successfully degrades four lignin monomers. • Successful degradation study at low (10°C) and moderate temperatures (20–30°C). • Biotechnological value: high yield of vanillic acid produced from ferulic acid.

Zur Biosynthese der Benzoesäuren in Gaultheria procumbens III

1966 ◽  
Vol 21 (5) ◽  
pp. 435-439 ◽  
Author(s):  
Karl-Otto Vollmer ◽  
Hans Grisebach
Keyword(s):  
Gas Chromatography ◽  
Thin Layer ◽  
Silicic Acid ◽  
Cinnamic Acid ◽  
Vanillic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Gentisic Acid ◽  
Gaultheria Procumbens

The cinnamic and benzoic acids present in Gaultheria procumbens could be separated by a combination of thin layer, paper, silicic acid, and gas chromatography. After administration of cinnamic-, o-coumaric-, and p-coumaric acid-[3-14C] to this plant, the amount of radioactivity in salicylic, p-hydroxybenzoic, gentisic, protocatechuic, and vanillic acid was quantitatively compared. Whereas all five of the latter acids were radioactive with cinnamic acid as the precursor, onky salicylic and gentisic acid contained radioactivity after administration of o-coumaric acid and only p-hydroxybenzoic, protocatechuic, and vanillic acid were radioactive with p-coumaric acid as the precursor. The results show that the hydroxylation pattern of the benzoic acids can be determined at the cinnamic acid stage.

Effects of Salinity Stress on Growth and Phenolics of Rice (Oryza sativa L.)

2016 ◽  
Vol 57 ◽  
pp. 1-10 ◽  
Author(s):  
Luong The Minh ◽  
Do Tan Khang ◽  
Pham Thi Thu Ha ◽  
Phung Thi Tuyen ◽  
Truong Ngoc Minh ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Ferulic Acid ◽  
Salinity Stress ◽  
Protocatechuic Acid ◽  
Total Phenolics ◽  
Susceptible Cultivar ◽  
Coumaric Acid ◽  
Rice Varieties ◽  
Stress Changes ◽  
Chemical Contents

This study was conducted to determine the correlation between of salinity stress on growth and phenolic compounds in rice. It was observed that salinity stress caused a significant decrease in shoot lengths, fresh and dry weights of all rice varieties. Under salinity stress, changes of chemical contents also differed among phenolic compounds and rice cultivars. Total phenolics and flavonoids, and contents of vanillin and protocatechuic acid in tolerant varieties were strongly increased, whereas in contrast, they were markedly reduced in the susceptible cultivar. Ferulic acid and p-coumaric acid were detected only in tolerance rice. Vanillin and protocatechuic acid may play a role, but ferulic acid and p-coumaric acid may be much involved in the tolerant mechanism against salinity stress. Ferulic acid and p-coumaric acid and their derivatives are able to be exploited as promising agents to reduce detrimental effects of salinity stress on rice production.

scholarly journals Solid-liquid phase equilibrium of trans-cinnamic acid, p-coumaric acid and ferulic acid in water and organic solvents: Experimental and modelling studies

2020 ◽  
Vol 521 ◽  
pp. 112747 ◽  
Author(s):  
Sérgio M. Vilas-Boas ◽  
Rebeca S. Alves ◽  
Paula Brandão ◽  
Leila M.A. Campos ◽  
João A.P. Coutinho ◽  
...  
Keyword(s):  
Phase Equilibrium ◽  
Liquid Phase ◽  
Ferulic Acid ◽  
Organic Solvents ◽  
Cinnamic Acid ◽  
Coumaric Acid ◽  
Modelling Studies ◽  
Solid Liquid
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