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.

Biosynthese von p-Hydroxybenzoesäure und anderer Benzoesäuren in höheren Pflanzen

1964 ◽  
Vol 19 (5) ◽  
pp. 398-405 ◽  
Author(s):  
M. H. Zenk ◽  
G. Müller
Keyword(s):  
Benzoic Acid ◽  
Protocatechuic Acid ◽  
Higher Plants ◽  
Side Chain ◽  
Hydroxybenzoic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Feeding Experiments ◽  
Catalpa Ovata

Feeding experiments with glucose- (2-14C), phenylalanine- (3-14C), tyrosine- (3-14C) and p-coumaric acid- (3-14C) showed that the latter three substances are incorporated in good yields into p-hydroxybenzoic acid in leaves of Catalpa ovata. Kinetic experiments showed that p-hydroxybenzoic acid is formed from phenylalanine via p-coumaric acid and the subsequent β-oxidation of the side chain. p-Hydroxybenzoic acid can also be synthetised by hydroxylation of benzoic acid, but this does not seem to be the biosynthetic route in Catalpa.Phenylalanine- (3-14C) is also incorporated into benzoic acid, protocatechuic acid, and vanillic acid by different plants; the radioactivity of the β-C atom of the amino acid was found in each case to be located in the carboxyl group of the C6 — C1 acid. This suggests that in higher plants the benzoic acids are formed from the corresponding cinnamic acids via β-oxidation.

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 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.

STUDIES ON THE BIOSYNTHESIS OF VOLUCRISPORIN: II. METABOLISM OF SOME PHENYLPROPANOID COMPOUNDS BY VOLUCRISPORA AURANTIACA HASKINS

1966 ◽  
Vol 44 (4) ◽  
pp. 403-413 ◽  
Author(s):  
P. Chandra ◽  
G. Read ◽  
L. C. Vining
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Hydroxycinnamic Acid ◽  
Phenyllactic Acid ◽  
Radioactive Substrate

DL-Phenyllactic acid-α-14C, DL-phenylserine-α-14C, L-phenylalanine-carboxyl-14C, and shikimic acid-U-14C were incorporated into phenylalanine and tyrosine isolated from mycelial hydrolysates of Volucrispora aurantiaca as well as into volucrisporin. DL-m-Tyrosine-carboxyl-14C was incorporated into volucrisporin but not into the aromatic amino acids. L-Tyrosine-β-14C, cinnamic acid-α-14C, and m-hydroxycinnamic acid-α-14C were metabolized by the fungus but did not serve as precursors of volucrisporin or of mycelial phenylalanine. The results are consistent with the concept of a biosynthetic pathway to volucrisporin via phenylpyruvic and m-hydroxyphenylpyruvic acids. Substantial amounts of each radioactive substrate fed to V. aurantiaca PRL 1952 were incorporated into a brown melanoid pigment.

Metabolism of mandelic acid by Neurospora crassa

1977 ◽  
Vol 23 (10) ◽  
pp. 1496-1499 ◽  
Author(s):  
D. N. Ramakrishna Rao ◽  
C. S. Vaidyanathan
Keyword(s):  
Aspergillus Niger ◽  
Benzoic Acid ◽  
Formic Acid ◽  
Neurospora Crassa ◽  
Mandelic Acid ◽  
Protocatechuic Acid ◽  
Hydroxybenzoic Acid ◽  
Bacterial Systems

Preliminary studies on the metabolism of mandelic acid by Neurospora crassa reveal the operation of a pathway for its degradation which involves benzoyl formic acid, benzaldehyde, benzoic acid, 4-hydroxybenzoic acid, and protocatechuic acid as the intermediates. This pathway is different from that followed by bacterial systems and is the same as that observed in Aspergillus niger.

scholarly journals Degradation of phenylalanine and tyrosine by Sporobolomyces roseus

1968 ◽  
Vol 106 (2) ◽  
pp. 507-514 ◽  
Author(s):  
Keith Moore ◽  
P. V. Subba Rao ◽  
G. H. N. Towers
Keyword(s):  
Benzoic Acid ◽  
Caffeic Acid ◽  
Cinnamic Acid ◽  
Protocatechuic Acid ◽  
Acid Metabolism ◽  
Hydroxybenzoic Acid ◽  
Coumaric Acid ◽  
Tracer Studies ◽  
Lyase Activity ◽  
Sporobolomyces Roseus

Ammonia-lyase activity for l-phenylalanine, m-hydroxyphenylalanine and l-tyrosine was demonstrated in cell-free extracts of Sporobolomyces roseus. Cultures of this organism converted dl-[ring−14C]phenylalanine and l-[U−14C]tyrosine into the corresponding cinnamic acid. Tracer studies showed that these compounds were further metabolized to [14C]protocatechuic acid. Benzoic acid and p-hydroxybenzoic acid were intermediates in this pathway. Washed cells of the organism readily utilized cinnamic acid, p-coumaric acid, caffeic acid, benzoic acid and p-hydroxybenzoic acid. Protocatechuic acid was the terminal aromatic compound formed during the metabolism of these compounds. The cells of S. roseus were able to convert m-coumaric acid into m-hydroxybenzoic acid, but the latter compound, which accumulated in the medium, was not further metabolized. 4-Hydroxycoumarin was identified as the product of o-coumaric acid metabolism by this organism.

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.

scholarly journals Bifidobacterium species associated with breastfeeding produce aromatic lactic acids in the infant gut

2021 ◽  
Author(s):  
Martin F. Laursen ◽  
Mikiyasu Sakanaka ◽  
Nicole von Burg ◽  
Urs Mörbe ◽  
Daniel Andersen ◽  
...  
Keyword(s):  
Amino Acids ◽  
Gut Microbiota ◽  
Immune Responses ◽  
Early Life ◽  
Bifidobacterium Longum ◽  
Aromatic Amino Acids ◽  
Dependent Manner ◽  
Microbial Metabolites ◽  
Phenyllactic Acid ◽  
Lactic Acids

AbstractBreastfeeding profoundly shapes the infant gut microbiota, which is critical for early life immune development, and the gut microbiota can impact host physiology in various ways, such as through the production of metabolites. However, few breastmilk-dependent microbial metabolites mediating host–microbiota interactions are currently known. Here, we demonstrate that breastmilk-promoted Bifidobacterium species convert aromatic amino acids (tryptophan, phenylalanine and tyrosine) into their respective aromatic lactic acids (indolelactic acid, phenyllactic acid and 4-hydroxyphenyllactic acid) via a previously unrecognized aromatic lactate dehydrogenase (ALDH). The ability of Bifidobacterium species to convert aromatic amino acids to their lactic acid derivatives was confirmed using monocolonized mice. Longitudinal profiling of the faecal microbiota composition and metabolome of Danish infants (n = 25), from birth until 6 months of age, showed that faecal concentrations of aromatic lactic acids are correlated positively with the abundance of human milk oligosaccharide-degrading Bifidobacterium species containing the ALDH, including Bifidobacterium longum, B. breve and B. bifidum. We further demonstrate that faecal concentrations of Bifidobacterium-derived indolelactic acid are associated with the capacity of these samples to activate in vitro the aryl hydrocarbon receptor (AhR), a receptor important for controlling intestinal homoeostasis and immune responses. Finally, we show that indolelactic acid modulates ex vivo immune responses of human CD4+ T cells and monocytes in a dose-dependent manner by acting as an agonist of both the AhR and hydroxycarboxylic acid receptor 3 (HCA3). Our findings reveal that breastmilk-promoted Bifidobacterium species produce aromatic lactic acids in the gut of infants and suggest that these microbial metabolites may impact immune function in early life.

Phenylacetic acid production by Bacteroides gingivalis from phenylalanine and phenylalanine-containing peptides

1983 ◽  
Vol 29 (9) ◽  
pp. 1184-1189 ◽  
Author(s):  
G. Bourgeau ◽  
D. Mayrand
Keyword(s):  
Amino Acids ◽  
Acid Production ◽  
Phenylacetic Acid ◽  
Cell Suspensions ◽  
Phenylpyruvic Acid ◽  
Phenyllactic Acid ◽  
Maximum Production ◽  
Resting Cell ◽  
Hydrocinnamic Acid ◽  
Bacteroides Gingivalis

Phenylacetic acid production and growth of Bacteroides gingivalis were directly proportional to the trypticase content of the medium. L-Phenylalanine enhanced phenylacetic acid production; 5 mg L-phenylalanine per millilitre stimulated maximum production of phenylacetic acid. Peptides (2–4 amino acids) containing L-phenylalanine also stimulated phenylacetic acid production as did phenylpyruvic acid. Resting cell suspensions of B. gingivalis also produced phenylacetic acid when incubated aerobically in the presence of L-phenylalanine and phenylpyruvic acid. Hydrocinnamic acid (3-phenylpropionic acid) and phenyllactic acid were also produced by resting cell suspensions. Our results suggest that L-phenylalanine and phenylpyruvic acid are both precursors to phenylacetic acid.

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