scholarly journals Biological Conversion of Shikimic Acid or Quinic Acid to Protocatechuic Acid, Gallic Acid and Aromatic Amino Acids

1959 ◽  
Vol 23 (5) ◽  
pp. 451-453
Author(s):  
Hisao ISHIKAWA ◽  
Tae OKI
Keyword(s):  
Amino Acids ◽  
Gallic Acid ◽  
Protocatechuic Acid ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Quinic Acid ◽  
Biological Conversion

BIOSYNTHESIS OF THE PHENYLPROPANOID MOIETY OF CHLORAMPHENICOL

1964 ◽  
Vol 10 (5) ◽  
pp. 705-716 ◽  
Author(s):  
L. C. Vining ◽  
D. W. S. Westlake
Keyword(s):  
Amino Acids ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Side Chain ◽  
Streptomyces Sp ◽  
Pass Through

Cultures of Streptomyces sp. 3022a were grown in the presence of C14-labelled substrates and incorporation of radioactivity into chloramphenicol measured. D-Glucose, labelled in carbons 1 or 2 or uniformly, was an efficient precursor of the p-nitrophenylserinol moiety and of the phenylpropanoid amino acids of the mycelium. The distribution of label in the ring and side-chain carbon atoms of p-nitrophenylserinol and cellular phenylalanine from experiments in which glucose-1-C14, glucose-2-C14, and glycine-2-C14 were fed provided evidence that the two phenylpropanoid systems had a common biosynthetic origin. The results were also consistent with their formation via the shikimic acid – prephenic acid route. Uniformly C14-labelled shikimic acid, though poorly utilized by this organism, was incorporated selectively into both the aromatic portion of chloramphenicol and the aromatic amino acids in the mycelium. L-Phenylalanine-U-C14, L-phenylalanine-carboxyl-C14, L-tyrosine-carboxyl-C14, DL-p-hydroxyphenylserine-2-C14, and acetate-2-C14 were poor precursors of the p-nitrophenylserinol moiety. Since phenylalanine and tyrosine were incorporated into the mycelium the biosynthetic route to the phenylpropanoid portion of chloramphenicol evidently does not pass through either of these amino acids but branches at an earlier step.

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.

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.

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.

scholarly journals Changes in Polar Metabolites Content during Natural and Methyl-Jasmonate-Promoted Senescence of Ginkgo biloba Leaves

2021 ◽  
Vol 23 (1) ◽  
pp. 266
Author(s):  
Marcin Horbowicz ◽  
Joanna Szablińska-Piernik ◽  
Justyna Góraj-Koniarska ◽  
Kensuke Miyamoto ◽  
Junichi Ueda ◽  
...  
Keyword(s):  
Amino Acids ◽  
Phosphoric Acid ◽  
Methyl Jasmonate ◽  
Ginkgo Biloba ◽  
Acid Content ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Primary Metabolism ◽  
Senescent Leaf ◽  
Polar Metabolites

The present study clarified changes in the contents of polar metabolites (amino acids, organic acids, saccharides, cyclitols, and phosphoric acid) in leaf senescence in Ginkgo biloba with or without the application of methyl jasmonate (JA-Me) in comparison with those in naturally senescent leaf blades and petioles. The contents of most amino acids and citric and malic acids were significantly higher in abaxially, and that of myo-inositol was lower in abaxially JA-Me-treated leaves than in adaxially JA-Me-treated and naturally senescent leaves. The levels of succinic and fumaric acids in leaves treated adaxially substantially high, but not in naturally senescent leaves. In contrast, sucrose, glucose, and fructose contents were much lower in leaf blades and petioles treated abaxially with JA-Me than those treated adaxially. The levels of these saccharides were also lower compared with those in naturally senescent leaves. Shikimic acid and quinic acid were present at high levels in leaf blades and petioles of G. biloba. In leaves naturally senescent, their levels were higher compared to green leaves. The shikimic acid content was also higher in the organs of naturally yellow leaves than in those treated with JA-Me. These results strongly suggest that JA-Me applied abaxially significantly enhanced processes of primary metabolism during senescence of G. biloba compared with those applied adaxially. The changes in polar metabolites in relation to natural senescence were also discussed.

scholarly journals Dissection of the Complex Transcription and Metabolism Regulation Networks Associated with Maize Resistance to Ustilago maydis

Genes ◽  
2021 ◽  
Vol 12 (11) ◽  
pp. 1789
Author(s):  
Xinsen Ruan ◽  
Liang Ma ◽  
Yingying Zhang ◽  
Qing Wang ◽  
Xiquan Gao
Keyword(s):  
Amino Acids ◽  
Defense Response ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Transcriptome Profiling ◽  
Ustilago Maydis ◽  
Reproductive Organs ◽  
Gene Effects ◽  
Metabolism Regulation ◽  
Maize Resistance

The biotrophic fungal pathogen Ustilago maydis causes common smut in maize, forming tumors on all aerial organs, especially on reproductive organs, leading to significant reduction in yield and quality defects. Resistance to U. maydis is thought to be a quantitative trait, likely controlled by many minor gene effects. However, the genes and the underlying complex mechanisms for maize resistance to U. maydis remain largely uncharacterized. Here, we conducted comparative transcriptome and metabolome study using a pair of maize lines with contrast resistance to U. maydis post-infection. WGCNA of transcriptome profiling reveals that defense response, photosynthesis, and cell cycle are critical processes in maize response to U. maydis, and metabolism regulation of glycolysis, amino acids, phenylpropanoid, and reactive oxygen species are closely correlated with defense response. Metabolomic analysis supported that phenylpropanoid and flavonoid biosynthesis was induced upon U. maydis infection, and an obviously higher content of shikimic acid, a key compound in glycolysis and aromatic amino acids biosynthesis pathways, was detected in resistant samples. Thus, we propose that complex gene co-expression and metabolism networks related to amino acids and ROS metabolism might contribute to the resistance to corn smut.

The Shikimate Pathway: Biosynthesis of Phenolic Products from Shikimic Acid

2016 ◽  
Author(s):  
Gary W. Morrow
Keyword(s):  
Amino Acids ◽  
Secondary Metabolites ◽  
Shikimic Acid ◽  
Shikimate Pathway ◽  
Aromatic Amino Acids ◽  
Essential Amino Acids ◽  
Bimolecular Reaction ◽  
Pentose Phosphate ◽  
Chemotherapy Agent ◽  
Acid Pathway

Like other amino acids, the aromatic amino acids phenylalanine, tyrosine, and tryptophan are vitally important for protein synthesis in all organisms. However, while animals can synthesize tyrosine via oxidation of phenylalanine, they can synthesize neither phenylalanine itself nor tryptophan and so these essential amino acids must be obtained in the diet, usually from plant material. Though many other investigators made significant contributions in this area over the years, it was Bernhard Davis in the early 1950s whose use of mutant stains of Escherichia coli led to a full understanding of the so-called shikimic acid pathway that is used by plants and also by some microorganisms for the biosynthesis of these essential amino acids. The pathway is almost completely devoted to their synthesis for protein production in bacteria, while in plants the pathway extends their use to the construction of a wide array of secondary metabolites, many of which are valuable medicinal agents. These secondary metabolites range from simple and familiar compounds such as vanillin (vanilla flavor and fragrance) and eugenol (oil of clove, a useful dental anesthetic) to more complex structures such as pinoresinol, a common plant biochemical, and podophyllotoxin, a powerful cancer chemotherapy agent. Earlier in Chapter 3, we encountered two important intermediates, erythrose-4-phosphate and phosphoenolpyruvate (PEP), each of which was derived from a different pathway utilized in carbohydrate metabolism. Erythrose-4-P was an intermediate in one of the steps of the pentose phosphate pathway while hydrolysis of PEP to pyruvic acid was the final step in glycolysis. These two simple intermediates provide the seven carbon atoms required for construction of shikimic acid itself. The two are linked to one another via a sequence of enzyme-mediated aldol-type reactions, the first being a bimolecular reaction and the second an intramolecular variant that ultimately leads to a cyclic precursor of shikimic acid known as 3-dehydroquinic acid as shown in Fig. 6.3. Subsequent dehydration of 3-dehydroquinic acid leads to 3-dehydroshikimic acid which then leads directly to shikimic acid via NADPH reduction.

IAA biosynthesis by the ectomycorrhizal fungus Hebeloma hiemale as affected by different precursors

1989 ◽  
Vol 67 (8) ◽  
pp. 2235-2239 ◽  
Author(s):  
G. Gay ◽  
R. Rouillon ◽  
J. Bernillon ◽  
J. Favre-Bonvin
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Shikimic Acid ◽  
Shikimate Pathway ◽  
Aromatic Amino Acids ◽  
Ectomycorrhizal Fungus ◽  
Limiting Factors ◽  
Symbiotic Association ◽  
Indole 3 Acetic Acid

The effect of different precursors, aromatic amino acids, or intermediates of the shikimate pathway (pathway for aromatic amino acids biosynthesis), on indole-3-acetic acid (IAA) synthesis by the ectomycorrhizal fungus Hebeloma hiemale was studied. This fungus did not release detectable amounts of IAA when cultivated on a medium containing no precursor or supplemented with 1 mM phenylalanine, 1 mM tyrosine or 1 mM shikimic acid. IAA accumulation in culture filtrates was low (0.5 μmol per flask) when the medium was supplemented with 1 mM anthranilic acid. The fungus released 1.6 μmol of IAA when cultivated on a medium containing 1 mM indole and 6.9 μmol in the presence of 1 mM tryptophan. These results were confirmed by studying the ability of crude enzyme extracts to convert these precursors to IAA. Specific IAA synthesizing activity was of the same order when indole or tryptophan were used as precursors. The comparison of in vivo and in vitro activity of IAA synthesizing enzymes demonstrated that a need for tryptophan concentrations higher than 0.1 mM to obtain detectable IAA synthesis is due to the low ratio of tryptophan breakdown into IAA. The inability of H. hiemale to synthesize IAA in the absence of precursors or in the presence of shikimic acid may be ascribed to a very poor endogenous tryptophan accumulation in the hyphae due to feed back inhibition of the anthranilate synthetase by tryptophan. These results indicate that precursor availability in root exudates is probably one of the main limiting factors for IAA release by ectomycorrhizal fungi under symbiotic association. Key words: ectomycorrhizal fungus, Hebeloma, indole-3-acetic acid, tryptophan, indole, shikimate pathway.

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