The formation of homogentisic acid from phenylacetic acid by an Aspergillus sp.

1973 ◽  
Vol 19 (3) ◽  
pp. 393-395 ◽  
Author(s):  
Teruo Ueno ◽  
Fumiki Yoshizako ◽  
Atsuo Nishimura
Keyword(s):  
Phenylacetic Acid ◽  
Acid Metabolism ◽  
Culture Fluid ◽  
Culture Technique ◽  
Homogentisic Acid ◽  
Aspergillus Species ◽  
Hydroxyphenylacetic Acid ◽  
Aspergillus Sp

Homogentisic acid was verified as one of the intermediates of phenylacetic acid metabolism by an Aspergillus species identified as a strain of A. fumigatus, using a replacement culture technique. o-Hydroxyphenylacetic acid was also detected in the culture fluid.

scholarly journals Biosynthesis of phytoquinones. Homogentisic acid: a precursor of plastoquinones, tocopherols and α-tocopherolquinone in higher plants, green algae and blue–green algae

1970 ◽  
Vol 117 (3) ◽  
pp. 593-600 ◽  
Author(s):  
G. R. Whistance ◽  
D. R. Threlfall
Keyword(s):  
Green Algae ◽  
Phenylacetic Acid ◽  
Higher Plants ◽  
Chlorella Pyrenoidosa ◽  
Homogentisic Acid ◽  
Side Chain ◽  
Methyl Groups ◽  
Blue Green Algae ◽  
Hydroxyphenylacetic Acid ◽  
Tracer Experiments

1. By means of 14C tracer experiments and isotope competition experiments the roles of d-tyrosine, p-hydroxyphenylpyruvic acid, p-hydroxyphenylacetic acid, phenylacetic acid, homogentisic acid and homoarbutin (2-methylquinol 4-β-d-glucoside) in the biosynthesis of plastoquinones, tocopherols and α-tocopherolquinone by maize shoots was investigated. It was established that d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid can all be utilized for this purpose, whereas p-hydroxyphenylacetic acid, phenylacetic acid and homoarbutin cannot. Studies on the mode of incorporation of d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid showed that their nuclear carbon atoms and the side-chain carbon atom adjacent to the nucleus give rise (as a C6-C1 unit) to the p-benzoquinone rings and nuclear methyl groups (one in each case) of plastoquinone-9 and α-tocopherolquinone and the aromatic nuclei and nuclear methyl groups (one in each case) of γ-tocopherol and α-tocopherol. 2. By using [14C]-homogentisic acid it has been shown that homogentisic acid is also a precursor of plastoquinone, tocopherols and α-tocopherolquinone in the higher plants Lactuca sativa and Rumex sanguineus, the green algae Chlorella pyrenoidosa and Euglena gracilis and the blue–green alga Anacystis nidulans.

scholarly journals A Soil-Borne Mn(II)-Oxidizing Bacterium of Providencia sp. Exploits a Strategy of Superoxide Production Coupled To Hydrogen Peroxide Consumption To Generate Mn Oxides

2021 ◽  
Author(s):  
Sha Chen ◽  
Zhexu Ding ◽  
Jinyuan Chen ◽  
Jun Luo ◽  
Xiaofang Ruan ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Transcriptome Sequencing ◽  
Phenylacetic Acid ◽  
Acid Metabolism ◽  
Biogeochemical Cycles ◽  
Oxygen Species ◽  
Metabolism Pathway ◽  
Dichlorofluorescin Diacetate ◽  
Mn Oxides ◽  
Distinct Increase

Abstract Bacterial non-enzymatic Mn(II) oxidation involving reactive oxygen species (ROS) (i.e. indirect oxidation), initially discovered from a marine alpha-proteobacterium, is believed to be of importance in controlling biogeochemical cycles. For soil-borne bacteria, however, evidence of indirect Mn(II) oxidation remains unclear. In this study, the indirect Mn(II) oxidation was evidenced in a soil-borne bacterium, Providencia sp. LLDRA6. First, with and without 50 mM of Mn(II) exposure for LLDRA6, 300 differentially expressed genes were found to be linked to Mn(II) exposure via transcriptome sequencing. Among them, an operon, responsible for phenylacetic acid catabolism, was sharply upregulated in transcription, drawing us a special attention since its transcriptional upregulation has recently shown to be important for withstanding ROS. Next, a fluorometric probe, 2′,7′-Dichlorofluorescin diacetate (DCFDA), was used to qualitatively detect ROS from cells, showing a distinct increase in fluorescence intensities of ROS during Mn(II) exposure. Further, concentrations of superoxide and hydrogen peroxide from cells were detected respectively with and without Mn(II) exposure, exhibiting that when Mn(II) oxidation occurred, superoxide concentration significantly increased but hydrogen peroxide concentration significantly decreased. Particularly, superoxide produced by LLDRA6 was proven to be the oxidant for Mn(II) in the formation of Mn oxides. Finally, we predicted links between phenylacetic acid metabolism pathway and ROS during Mn(II) exposure, proposing that the excessive ROS, generated in response to Mn(II) exposure, transcriptionally activate phenylacetic acid catabolism presumably by increasing concentrations of highly reactive oxepins.

Degradation of the Isoflavone Biochanin A-7-O-glucoside-6"O-inalonate and Phenylacetic Acids by Fusarium javanicum

1984 ◽  
Vol 39 (9-10) ◽  
pp. 882-887 ◽  
Author(s):  
Dittmar Schlieper ◽  
Dieter Komoßa ◽  
Wolfgang Barz
Keyword(s):  
Phenylacetic Acid ◽  
Biochanin A ◽  
Acid Degradation ◽  
Hydroxyphenylacetic Acid

Keywords The isoflavone conjugate biochanin A-7-O-glucoside-6″-O-malonate is degraded by Fusarium javanicum with an esterase to yield biochanin A-7-O-glucoside which is further cleaved by a glucosidase to the aglycone. Biochanin A is funnelled into a known catabolic sequence (Z. Naturforsch. 37c, 861 (1982)). Induction of the catabolism of p-methoxyphenylacetic acid is linked to biochanin A degradation, whereas p-hydroxyphenylacetic acid and 3,4-dihydroxy- phenylacetic acid degradation is substrate-induced.

The metabolism of p-fluorophenylacetic acid by a Pseudomonas sp. I. Isolation and identification of intermediates in degradation

1971 ◽  
Vol 17 (5) ◽  
pp. 635-644 ◽  
Author(s):  
D. B. Harper ◽  
E. R. Blakley
Keyword(s):  
Sole Carbon Source ◽  
Culture Medium ◽  
Enrichment Culture ◽  
Culture Technique ◽  
Spectroscopic Techniques ◽  
Resting Cells ◽  
Pseudomonas Sp ◽  
Isolation And Identification ◽  
Hydroxyphenylacetic Acid ◽  
Organic Fluorine

A Pseudomonas sp. capable of growing on p-fluorophenylacetic acid as sole carbon source has been isolated using the enrichment culture technique. All the organic fluorine is released into the culture medium as fluoride ion during growth. A number of fluorinated intermediates have been isolated from the culture medium when resting cells were incubated with the substrate. Using infrared, nuclear magnetic resonance, and mass spectroscopic techniques together with chemical degradative procedures, these have been identified as D(+)-monofluorosuccinic acid, trans-3-fluoro-3-hexenedioic acid, (−)-4-carboxymethyl-4-fluorobutanolide, 4-fluoro-2-hydroxyphenylacetic acid, and 4-fluoro-3-hydroxyphenylacetic acid.

Degradation of (–)-Ephedrine by Pseudomonas putida Detection of (–)-Ephedrine: NAD+-oxidoreductase from Arthrobacter globiformis

1980 ◽  
Vol 35 (1-2) ◽  
pp. 80-87 ◽  
Author(s):  
E. Klamann ◽  
F. Lingens
Keyword(s):  
Pseudomonas Putida ◽  
Enrichment Culture ◽  
Culture Fluid ◽  
Sole Source ◽  
Culture Technique ◽  
Arthrobacter Globiformis ◽  
Muconic Acid ◽  
Ammonium Sulphate Precipitation ◽  
Wide Range ◽  
Nad Oxidoreductase

Abstract A bacterium utilizing the alkaloid (-)-ephedrine as its sole source of carbon was isolated by an enrichment-culture technique from soil supplemented with 4-benzoyl-1,3-oxazolidinon-(2). The bacterium was identified as Pseudomonasputida by morphological and physiological studies. The following metabolites were isolated from the culture fluid: methylamine, formaldehyde, methyl- benzoylcarbinol (2-hydroxy-1-oxo-1-phenylpropane), benzoid acid, pyrocatechol and cis, cis- muconic acid. A pathway for the degradation of (-)-ephedrine by Pseudomonas putida is proposed and compared with the degradative pathway in Arthrobacter globiformis.The enzyme, which is responsible for the first step in the catabolism of (-)-ephedrine could be demonstrated in extracts from Arthrobacter globiformis. This enzyme catalyses the dehydrogena- tion of (-)-ephedrine yielding phenylacetylcarbinol/methylbenzoylcarbinol and methylamine. It requires NAD+ as cofactor and exhibits optimal activity at pH 11 in 0.1 m glycine/NaOH buffer. The Km value for (-)-ephedrine is 0.02 mM and for NAD+ 0.11 mм, respectively. No remarkable loss of activity is observed following treatment with EDTA. The enzyme has been shown to react with a wide range of ethanolamines. A slight enrichment was obtained by ammonium sulphate precipitation. The name (-)-ephedrine: NAD+-oxidoreductase (deaminating) is proposed.

scholarly journals Catabolism of aromatics in Pseudomonas putida U. Formal evidence that phenylacetic acid and 4-hydroxyphenylacetic acid are catabolized by two unrelated pathways

1994 ◽  
Vol 221 (1) ◽  
pp. 375-381 ◽  
Author(s):  
Elias R. OLIVERA ◽  
Angel REGLERO ◽  
Honorina MARTINEZ-BLANCO ◽  
Alberto FERNANDEZ-MEDARDE ◽  
Miguel A. MORENO ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Phenylacetic Acid ◽  
Hydroxyphenylacetic Acid

scholarly journals p-Hydroxyphenylacetic Acid Metabolism inPseudomonas putida F6

2001 ◽  
Vol 183 (3) ◽  
pp. 928-933 ◽  
Author(s):  
Kevin E. O'Connor ◽  
Bernard Witholt ◽  
Wouter Duetz
Keyword(s):  
Pseudomonas Putida ◽  
Enzyme Activities ◽  
Acid Metabolism ◽  
Ring Cleavage ◽  
Acid Oxidation ◽  
Dihydroxyphenylacetic Acid ◽  
Cell Extracts ◽  
Hydroxyphenylacetic Acid ◽  
Brown Color

ABSTRACT Pseudomonas putida F6 was found to metabolizep-hydroxyphenylacetic acid through 3,4-dihydroxyphenylacetic acid, 3,4-dihydroxymandelic acid, and 3,4-dihydroxybenzaldehyde. Cell extracts of P. putida F6 catalyze the NAD(P)H-independent hydroxylation ofp-hydroxyphenylacetic acid to 3,4-dihydroxyphenylacetic acid which is further oxidized to 3,4-dihydroxymandelic acid. Oxidation and decarboxylation of the latter yields 3,4-dihydroxybenzaldehyde. A red-brown color accompanies all of the above enzyme activities and is probably due to the polymerization of quinone-like compounds. 3,4-Dihydroxybenzaldehyde is further metabolized through extradiol ring cleavage.

scholarly journals Ruminal bioshynthesis of aromatic amino acids from arylacetic acids, glucose, shikimic acid and phenol

1974 ◽  
Vol 31 (3) ◽  
pp. 357-365 ◽  
Author(s):  
S. Kristensen
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Phenylacetic Acid ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Hydroxyphenylacetic Acid ◽  
Arylacetic Acids ◽  
First Time ◽  
Indole 3 Acetic Acid

1. Ruminal metabolism of labelled phenylacetic acid, 4-hydroxyphenylacetic acid, indole-3-acetic acid, glucose, shikimic acid, phenol, and serine was studied in vitro by short-term incubation with special reference to incorporation rates into aromatic amino acids.2. Earlier reports on reductive carboxylation of phenylacetic acid and indole-3-acetic acid in the rumen were confirmed and the formation of tyrosine from 4-hydroxyphenylacetic acid was demonstrated for the first time.3. The amount of phenylalanine synthesized from phenylacetic acid was estimated to be 2 mg/1 rumen contents per 24 h, whereas the amount synthesized from glucose might be eight times as great, depending on diet.4. Shikimic acid was a poor precursor of the aromatic amino acids, presumably owing to its slow entry into rumen bacteria.5. A slow conversion of phenol into tyrosine was observed.

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