METABOLISM OF PHENYLPROPANOID COMPOUNDS IN SALVIA: I. BIOSYNTHESIS OF PHENYLALANINE AND TYROSINE

1959 ◽  
Vol 37 (4) ◽  
pp. 531-536 ◽  
Author(s):  
D. R. McCalla ◽  
A. C. Neish
Keyword(s):  
Glutamic Acid ◽  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Oxidative Breakdown ◽  
Specific Activities ◽  
Good Precursor

C14-Labelled shikimic acid, L-phenylalanine, D-phenylalanine, L-tyrosine, and cinnamic acid were fed separately to leafy cuttings of salvia. After a metabolic period of 24 hours the free and bound phenylalanine, tyrosine, and glutamic acid were isolated from the stems, and their specific activities measured. Shikimic acid was found to be a good precursor of both phenylalanine and tyrosine. There was little interconversion of phenylalanine and tyrosine, and hardly any oxidative breakdown of these compounds to glutamic acid precursors. D-Phenylalanine was metabolized more slowly than L-phenylalanine but it was superior to cinnamic acid as a precursor of bound phenylalanine and tyrosine.

METABOLISM OF PHENYLPROPANOID COMPOUNDS IN SALVIA: I. BIOSYNTHESIS OF PHENYLALANINE AND TYROSINE

1959 ◽  
Vol 37 (1) ◽  
pp. 531-536 ◽  
Author(s):  
D. R. McCalla ◽  
A. C. Neish
Keyword(s):  
Glutamic Acid ◽  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Oxidative Breakdown ◽  
Specific Activities ◽  
Good Precursor

C14-Labelled shikimic acid, L-phenylalanine, D-phenylalanine, L-tyrosine, and cinnamic acid were fed separately to leafy cuttings of salvia. After a metabolic period of 24 hours the free and bound phenylalanine, tyrosine, and glutamic acid were isolated from the stems, and their specific activities measured. Shikimic acid was found to be a good precursor of both phenylalanine and tyrosine. There was little interconversion of phenylalanine and tyrosine, and hardly any oxidative breakdown of these compounds to glutamic acid precursors. D-Phenylalanine was metabolized more slowly than L-phenylalanine but it was superior to cinnamic acid as a precursor of bound phenylalanine and tyrosine.

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.

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.

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 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.

Zur Biogenese von 5-Hydroxy-1.4-naphthochinon (Juglon) in Juglans regia L.

1968 ◽  
Vol 23 (2) ◽  
pp. 259-268 ◽  
Author(s):  
E. Leistner ◽  
M. H. Zenk
Keyword(s):  
Benzene Ring ◽  
Higher Plants ◽  
Shikimic Acid ◽  
Juglans Regia ◽  
Chemical Degradation ◽  
Carboxyl Group ◽  
Symmetrical Molecule ◽  
Important Intermediate ◽  
Chorismic Acid ◽  
Good Precursor

The biosynthesis of 5-hydroxy-1,4-naphthoquinone (juglone) was studied by supplying radioactive precursors to leaves of Juglans regia plants. A chemical degradation of the juglone molecule was devised (Fig. 1). With these methods it was shown that the ring atoms of shikimic acid are incorporated into the benzene ring of the quinone, while the carboxyl group of this acid is transformed to 50% into each of the keto groups of the quinone ring (C-atoms 1 and 4 of juglone. Tab. 3). This suggested a symmetrical molecule to be an intermediate in the formation of juglone — most probable 1,4-naphthoquinone. This compound was synthetized with 14C in the positions 2, 3, 9, and 10 and was found to be a good precursor of juglone in Juglans as well as for 2-hydroxy-1,4-naphthoquinone in Impatiens plants (Tab. 4) . 3,4-Dihydroxybenzaldehyde (Tab. 2) and chorismic acid (Tab. 7) which have been suggested previously as intermediates in the biosynthesis of naphthoquinones are no precursors of juglone. The source of three carbon atoms of the quinone nucleus remains to be determined; one or two of these carbon atoms (C2 and/or C3 of juglone) are formed from the methylen carbon of malonate (Tab. 5 and 6); surprisingly, however, the carboxyl carbons of malonic acid are not incorporated. The substitution of shikimic acid occures in the position 6 of this acid as could be judged from the degradation of juglone labelled with shikimic acid [ 1,2-14C] (Fig. 2; Tab. 3). 1,4-Naphthoquinone (or naphthohydroquinone) is postulated as an important intermediate in the biosynthesis of naphthoquinone derivatives in higher plants.

scholarly journals Incorporation of dl-[2−14C]ornithine and dl-[5−14C]arginine in milk constituents by the isolated lactating sheep udder

1968 ◽  
Vol 106 (3) ◽  
pp. 719-724 ◽  
Author(s):  
R. Verbeke ◽  
G. Peeters ◽  
Anne Marie Massart-Leën ◽  
G. Cocquyt
Keyword(s):  
Carbon Dioxide ◽  
Amino Acids ◽  
Glutamic Acid ◽  
Mammary Glands ◽  
Total Radioactivity ◽  
Chemical Degradation ◽  
Mammary Tissue ◽  
Specific Activities ◽  
Plasma Arginine

1. Lactating mammary glands of sheep were perfused for several hours in the presence of dl-[2−14C]ornithine or dl-[5−14C]arginine and received adequate quantities of acetate, glucose and amino acids. 2. In the [14C]ornithine experiment 1·4% of the casein and 1% of the expired carbon dioxide came from added ornithine; 96% of the total radioactivity in casein was recovered in proline; 13% of the proline of casein originated from plasma ornithine. 3. In this experiment the results of chemical degradation of proline of casein as well as relative specific activities in the isolated products are consistent with the view that ornithine is metabolized, by way of glutamic γ-semialdehyde, to proline or glutamic acid. 4. In the [14C]arginine experiments 3% of the casein and 1% of the expired carbon dioxide came from arginine; 84% of the arginine and 9% of the proline of casein originated from plasma arginine. 5. In these experiments the relative specific activities of arginine, ornithine and proline in plasma are in agreement with the view that arginine is metabolized by way of ornithine to proline. The conversion of arginine into ornithine is probably catalysed by arginase, so that arginase in mammary tissue may be involved in the process of milk synthesis.

Metabolism of [U-14C]-l-threonine and [U-14C]-l-phenylalanine by the isolated perfused udder

1972 ◽  
Vol 39 (2) ◽  
pp. 239-250 ◽  
Author(s):  
R. Verbeke ◽  
E. Roets ◽  
Anne-Marie Massart-Leën ◽  
G. Peeters
Keyword(s):  
Amino Acids ◽  
Mammary Gland ◽  
Citric Acid ◽  
Glutamic Acid ◽  
Plasma Levels ◽  
Mammary Tissue ◽  
Phenylalanine Concentration ◽  
Plasma Phenylalanine ◽  
Lactating Mammary Gland ◽  
Specific Activities

SummaryA lactating mammary gland of a goat was perfused for 9 h in the presence of [U-14C]-l-threonine and received adequate quantities of glucose, acetate and amino acids. Two lactating sheep udders were likewise perfused in the presence of [U-14C]-l-phenylalanine: the plasma levels of phenylalanine in the first of these experiments were 4 times higher than in the second.In the [14C]threonine experiment, 4 % of the casein and 0·4 % of the expired CO2 were derived from threonine; 85 % of the threonine and 1·6 % of the glycine residues in casein originated from plasma threonine. Small 14C levels were found in glutamic acid, aspartic acid and serine of casein. The relative specific activities amongst the casein amino acids and the appearance of appreciable labelling in plasma glycine are consistent with the view that threonine is split by threonine aldolase.In the [14C]phenylalanine experiments virtually no radioactivity was detected in CO2, lactose or citric acid, indicating that this substrate is not broken down by mammary tissue. In the second experiment, 96 % of the phenylalanine and 0·3 % of the tyrosine of casein originated from plasma phenylalanine. In the first experiment, a 30-fold higher 14C incorporation into casein tyrosine relative to phenylalanine was observed. The possible significance of the phenylalanine concentration in the plasma on the degree of conversion of phenylalanine into tyrosine within the mammary gland is discussed.

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