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.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XIII. THE PHENYLPROPANOID SYSTEM IN LIGNIFICATION

1963 ◽  
Vol 41 (1) ◽  
pp. 621-628 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Amino Acids ◽  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Coniferyl Alcohol ◽  
Phenyllactic Acid ◽  
Phenylalanine Deaminase

Techniques of isotope competition and trapping were used to study the phenylpropanoid biosynthetic pathway in lignifying wheat plants. The results in general confirm earlier findings that phenyllactic acid (PLA), p-hydroxyphenyllactic acid (HPLA), phenylpyruvic, cinnamic, caffeic, ferulic, and sinapic acids can participate in lignification. L-Phenylalanine and L-tyrosine were converted to PLA and HPLA, respectively, but there was much less conversion of cinnamic acid to PLA, or p-hydroxycinnamic acid to HPLA. A pathway from phenylalanine to cinnamic acid via PLA, and an analogous pathway involving tyrosine thus remain as possible alternatives to the established routes involving deamination of these amino acids by phenylalanine deaminase or tyrase. Feeding of non-radioactive coniferyl alcohol with ferulic acid-C14 results in the formation of both coniferyl- and sinapyl-type lignin residues having lower specific radioactivities than were obtained after the feeding of ferulic acid-C14 alone. After a 5-hour metabolic period in the presence of ferulic acid-C14, both coniferyl aldehyde and coniferyl alcohol became labelled, and the radioactivity of the aldehyde was much higher than that of the alcohol. There was no evidence of coniferin formation. These findings indicate that coniferyl alcohol is formed from ferulic acid through coniferyl aldehyde, and that coniferin is probably unnecessary for lignification, at least in species other than conifers.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XIII. THE PHENYLPROPANOID SYSTEM IN LIGNIFICATION

1963 ◽  
Vol 41 (3) ◽  
pp. 621-628 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Amino Acids ◽  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Coniferyl Alcohol ◽  
Phenyllactic Acid ◽  
Phenylalanine Deaminase

Techniques of isotope competition and trapping were used to study the phenylpropanoid biosynthetic pathway in lignifying wheat plants. The results in general confirm earlier findings that phenyllactic acid (PLA), p-hydroxyphenyllactic acid (HPLA), phenylpyruvic, cinnamic, caffeic, ferulic, and sinapic acids can participate in lignification. L-Phenylalanine and L-tyrosine were converted to PLA and HPLA, respectively, but there was much less conversion of cinnamic acid to PLA, or p-hydroxycinnamic acid to HPLA. A pathway from phenylalanine to cinnamic acid via PLA, and an analogous pathway involving tyrosine thus remain as possible alternatives to the established routes involving deamination of these amino acids by phenylalanine deaminase or tyrase. Feeding of non-radioactive coniferyl alcohol with ferulic acid-C14 results in the formation of both coniferyl- and sinapyl-type lignin residues having lower specific radioactivities than were obtained after the feeding of ferulic acid-C14 alone. After a 5-hour metabolic period in the presence of ferulic acid-C14, both coniferyl aldehyde and coniferyl alcohol became labelled, and the radioactivity of the aldehyde was much higher than that of the alcohol. There was no evidence of coniferin formation. These findings indicate that coniferyl alcohol is formed from ferulic acid through coniferyl aldehyde, and that coniferin is probably unnecessary for lignification, at least in species other than conifers.

METABOLISM OF PHENYLPROPANOID COMPOUNDS IN SALVIA: II. BIOSYNTHESIS OF PHENOLIC CINNAMIC ACIDS

1959 ◽  
Vol 37 (1) ◽  
pp. 537-547 ◽  
Author(s):  
D. R. McCalla ◽  
A. C. Neish
Keyword(s):  
Caffeic Acid ◽  
Phenolic Acids ◽  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Phenyllactic Acid ◽  
Salvia Splendens ◽  
Specific Activities

p-Coumaric, caffeic, ferulic, and sinapic acids were found to occur in Salvia splendens Sello in alkali-labile compounds of unknown constitution. A number of C14-labelled compounds were administered to leafy cuttings of salvia and these phenolic acids were isolated after a metabolic period of several hours and their specific activities measured. Cinnamic acid, dihydrocinnamic acid, L-phenylalanine, and (−)-phenyllactic acid were found to be good precursors of the phenolic acids. D-Phenylalanine, L-tyrosine, and (+)-phenyllactic acid were poor precursors. A kinetic study of the formation of the phenolic acids from L-phenylalanine-C14 gave data consistent with the view that p-coumaric acid → caffeic acid → ferulic acid → sinapic acid, and that these compounds can act as intermediates in lignification. Feeding of C14-labelled members of this series showed that salvia could convert any one to a more complex member of the series but not so readily to a simpler member. Caffeic acid-β-C14 was obtained from salvia after the feeding of L-phenylalanine-β-C14 or cinnamic acid-β-C14, and caffeic acid labelled only in the ring was obtained after feeding generally labelled shikimic acid.

scholarly journals Identification of the Tyrosine- and Phenylalanine-Derived Soluble Metabolomes of Sorghum

2021 ◽  
Vol 12 ◽  
Author(s):  
Jeffrey P. Simpson ◽  
Jacob Olson ◽  
Brian Dilkes ◽  
Clint Chapple
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Aromatic Amino Acids ◽  
Flavonoid Glycosides ◽  
Coumaric Acid ◽  
Biotic And Abiotic Stress ◽  
Proportional Contribution ◽  
Negative Ionization ◽  
Derivatives Of

The synthesis of small organic molecules, known as specialized or secondary metabolites, is one mechanism by which plants resist and tolerate biotic and abiotic stress. Many specialized metabolites are derived from the aromatic amino acids phenylalanine (Phe) and tyrosine (Tyr). In addition, the improved characterization of compounds derived from these amino acids could inform strategies for developing crops with greater resilience and improved traits for the biorefinery. Sorghum and other grasses possess phenylalanine ammonia-lyase (PAL) enzymes that generate cinnamic acid from Phe and bifunctional phenylalanine/tyrosine ammonia-lyase (PTAL) enzymes that generate cinnamic acid and p-coumaric acid from Phe and Tyr, respectively. Cinnamic acid can, in turn, be converted into p-coumaric acid by cinnamate 4-hydroxylase. Thus, Phe and Tyr are both precursors of common downstream products. Not all derivatives of Phe and Tyr are shared, however, and each can act as a precursor for unique metabolites. In this study, 13C isotopic-labeled precursors and the recently developed Precursor of Origin Determination in Untargeted Metabolomics (PODIUM) mass spectrometry (MS) analytical pipeline were used to identify over 600 MS features derived from Phe and Tyr in sorghum. These features comprised 20% of the MS signal collected by reverse-phase chromatography and detected through negative-ionization. Ninety percent of the labeled mass features were derived from both Phe and Tyr, although the proportional contribution of each precursor varied. In addition, the relative incorporation of Phe and Tyr varied between metabolites and tissues, suggesting the existence of multiple pools of p-coumaric acid that are fed by the two amino acids. Furthermore, Phe incorporation was greater for many known hydroxycinnamate esters and flavonoid glycosides. In contrast, mass features derived exclusively from Tyr were the most abundant in every tissue. The Phe- and Tyr-derived metabolite library was also utilized to retrospectively annotate soluble MS features in two brown midrib mutants (bmr6 and bmr12) identifying several MS features that change significantly in each mutant.

Amino group requirement for in vitro intestinal transport of amino acids

1962 ◽  
Vol 202 (1) ◽  
pp. 171-173 ◽  
Author(s):  
Richard P. Spencer ◽  
Ted M. Bow ◽  
Mary Anne Markulis
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Cinnamic Acid ◽  
Concentration Gradient ◽  
Anthranilic Acid ◽  
Intestinal Transport ◽  
Amino Group ◽  
Phenylpyruvic Acid ◽  
Phenyllactic Acid

The amino group requirement for transintestinal transport of amino acids against a concentration gradient was investigated using hamster everted intestinal sacs. Although glycine (5 x 10–3 m) was transported against a concentration gradient, acetic acid was not. Similarly, l-phenylalanine was transported, whereas phenylpyruvic acid, phenylpropionic acid, phenyllactic acid, and cinnamic acid were not. l-Tryptophan was transported, but indolyllactic acid was not. The amino group was thus essential for transport by this system. n-Methylglycine and l-proline were accumulated from mucosa to serosa against a concentration gradient. Hence, one hydrogen of the amino group can be replaced. However, n-phenylglycine was not accumulated across these preparations, suggesting that the moiety replacing the amino hydrogen can not be sterically bulky. α-l-Alanine was transported against a concentration gradient from mucosa to serosa, but ß-alanine was not. This is in contrast to other systems which accumulate ß-alanine against a concentration gradient. Anthranilic acid, with the amino group in a relative ß position, was also not accumulated across everted intestinal sacs.

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.

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.

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