scholarly journals Phenylalanine, Tyrosine, and DOPA Are Bona Fide Substrates for Bambusa oldhamii BoPAL4

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1263
Author(s):  
Chun-Yen Hsieh ◽  
Yi-Hao Huang ◽  
Hui-Hsuan Yeh ◽  
Pei-Yu Hong ◽  
Che-Jen Hsiao ◽  
...  
Keyword(s):  
Substrate Specificity ◽  
Cinnamic Acid ◽  
Phenylalanine Ammonia Lyase ◽  
Coumaric Acid ◽  
Wild Type ◽  
Km Value ◽  
Optimum Reaction ◽  
Bona Fide ◽  
Specific Activities ◽  
Bambusa Oldhamii

Phenylalanine ammonia-lyase (PAL) links the plant primary and secondary metabolisms, and its product, trans-cinnamic acid, is derived into thousands of diverse phenylpropanoids. Bambusa oldhamii BoPAL4 has broad substrate specificity using L-phenylalanine, L-tyrosine, and L-3,4-dihydroxy phenylalanine (L-DOPA) as substrates to yield trans-cinnamic acid, p-coumaric acid, and caffeic acid, respectively. The optimum reaction pH of BoPAL4 for three substrates was measured at 9.0, 8.5, and 9.0, respectively. The optimum reaction temperatures of BoPAL4 for three substrates were obtained at 50, 60, and 40 °C, respectively. The Km values of BoPAL4 for three substrates were 2084, 98, and 956 μM, respectively. The kcat values of BoPAL4 for three substrates were 1.44, 0.18, and 0.06 σ-1, respectively. The major substrate specificity site mutant, BoPAL4-H123F, showed better affinity toward L-phenylalanine by decreasing its Km value to 640 μM and increasing its kcat value to 1.87 s-1. In comparison to wild-type BoPAL4, the specific activities of BoPAL4-H123F using L-tyrosine and L-DOPA as substrates retained 5.4% and 17.8% residual activities. Therefore, L-phenylalanine, L-tyrosine, and L-DOPA are bona fide substrates for BoPAL4.

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.

BIOSYNTHESIS OF THE COUMARINS. TRACER STUDIES ON COUMARIN FORMATION IN HIEROCHLOË ODORATA AND MELILOTUS OFFICINALIS

1960 ◽  
Vol 38 (2) ◽  
pp. 143-156 ◽  
Author(s):  
Stewart A. Brown ◽  
G. H. N. Towers ◽  
D. Wright
Keyword(s):  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Perennial Grass ◽  
Coumaric Acid ◽  
Sweet Clover ◽  
Tracer Studies ◽  
Melilotus Officinalis ◽  
Specific Activities ◽  
Acid Pathway ◽  
Hierochloe Odorata

Coumarin formation has been studied with C14in the perennial grass, Hierochloë odorata, and in yellow sweet clover, Melilotus officinalis. In general the latter species yielded inconsistent data. In Hierochloë, o-coumaric, cinnamic, and shikimic acids and L-phenylalanine were the best of 10 compounds tested as coumarin precursors, the first two at least being incorporated with little randomization of C14. Acetate was more poorly utilized. It was concluded that the aromatic ring of coumarin arises via the shikimic acid pathway in preference to acetate condensation. When the time of metabolism was varied, o-coumaryl glucoside and free o-coumaric acid rapidly acquired high specific activities from cinnamic acid-C14, but coumarin and melilotic acid became active much more slowly. A lag in the acquisition of C14by coumarin for the first 6 to 8 hours was followed by a rectilinear increase until at least 24 hours. Much the greatest accumulation of C14was found in o-coumaryl glucoside during this entire period. Furthermore, this compound when fed to Hierochloë is comparable to cinnamic acid as a coumarin precursor. These findings suggest a possible function for o-coumaryl glucoside or a derivative in coumarin biosynthesis.

BIOSYNTHESIS OF THE COUMARINS. TRACER STUDIES ON COUMARIN FORMATION IN HIEROCHLOË ODORATA AND MELILOTUS OFFICINALIS

1960 ◽  
Vol 38 (1) ◽  
pp. 143-156 ◽  
Author(s):  
Stewart A. Brown ◽  
G. H. N. Towers ◽  
D. Wright
Keyword(s):  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Perennial Grass ◽  
Coumaric Acid ◽  
Sweet Clover ◽  
Tracer Studies ◽  
Melilotus Officinalis ◽  
Specific Activities ◽  
Acid Pathway ◽  
Hierochloe Odorata

Coumarin formation has been studied with C14in the perennial grass, Hierochloë odorata, and in yellow sweet clover, Melilotus officinalis. In general the latter species yielded inconsistent data. In Hierochloë, o-coumaric, cinnamic, and shikimic acids and L-phenylalanine were the best of 10 compounds tested as coumarin precursors, the first two at least being incorporated with little randomization of C14. Acetate was more poorly utilized. It was concluded that the aromatic ring of coumarin arises via the shikimic acid pathway in preference to acetate condensation. When the time of metabolism was varied, o-coumaryl glucoside and free o-coumaric acid rapidly acquired high specific activities from cinnamic acid-C14, but coumarin and melilotic acid became active much more slowly. A lag in the acquisition of C14by coumarin for the first 6 to 8 hours was followed by a rectilinear increase until at least 24 hours. Much the greatest accumulation of C14was found in o-coumaryl glucoside during this entire period. Furthermore, this compound when fed to Hierochloë is comparable to cinnamic acid as a coumarin precursor. These findings suggest a possible function for o-coumaryl glucoside or a derivative in coumarin biosynthesis.

Studies on the Regulatory Role of trans-Cinnamic Acid on the Activity of the Phenylalanine Ammonia-Lyase (PAL) in Suspension Cultures of Daucus carota L.

1983 ◽  
Vol 38 (5-6) ◽  
pp. 408-412 ◽  
Author(s):  
W. Noé ◽  
H. U. Seitz
Keyword(s):  
Protein Synthesis ◽  
Cinnamic Acid ◽  
Phenylalanine Ammonia Lyase ◽  
Competitive Inhibitor ◽  
Regulatory Role ◽  
Coumaric Acid ◽  
Daucus Carota L

In vivo and in vitro experiments were performed in order to study the regulatory role of trans- cinnamic acid and its hydroxylated derivatives (p-coumaric acid, caffeic acid) on the deamina­tion of phenylalanine catalyzed by PAL (EC 4.3.1.5). Trans-cinnamic acid inhibits growth and reduces the content of soluble proteins of anthocyanin-containing carrot cells grown in suspen­sion. There is strong evidence from the polysomal patterns and from the effect of trans-cinnamic acid on protein synthesis in vitro that protein synthesis is inhibited. The kinetic data of PAL clearly demonstrate that trans-cinnamic acid inhibits the enzyme by a noncompetitive mecha­nism. On the contrary, ʟ-α-aminooxy-β-phenylpropionic acid (ʟ-AOPP), a competitive inhibitor of PAL, does not affect protein metabolism.

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

1959 ◽  
Vol 37 (4) ◽  
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.

Amylase hyper-producing haploid recombinant strains of Thermomyces lanuginosus obtained by intraspecific protoplast fusion

2000 ◽  
Vol 46 (7) ◽  
pp. 669-673 ◽  
Author(s):  
K Rubinder ◽  
B S Chadha ◽  
S Singh ◽  
H S Saini
Keyword(s):  
Protoplast Fusion ◽  
Culture Filtrate ◽  
Catabolite Repression ◽  
Type Strain ◽  
Wild Type Strain ◽  
Thermomyces Lanuginosus ◽  
Wild Type ◽  
Haploid Strain ◽  
Recombinant Strains ◽  
Specific Activities

Amylase hyper-producing, catabolite-repression-resistant, recombinant strains were produced by intraspecific protoplast fusion of thermophilic fungus Thermomyces lanuginosus strains, using well-characterized, morphological, and 2-deoxy-D-glucose resistant markers. The fusant heterokaryons exhibited enhanced amylase activities as compared to the amylase hyper-producing parental strain (T2). Diploids derived from heterokaryons segregated to stable haploid recombinant strains. In the haploid strain (Tlh 4q), approximately 5-fold higher specific activities of α-amylase and glucoamylase in the culture filtrate were observed as compared to the wild-type strain (W0).Key words: Thermomyces lanuginosus, protoplast fusion, amylase hyper-producing strain, catabolite repression.

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.

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