STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: X. FORMATION OF LIGNIN FROM PHENYLPROPANOIDS IN TISSUE CULTURE OF WHITE PINE

1962 ◽  
Vol 40 (1) ◽  
pp. 31-34 ◽  
Author(s):  
Takayoshi Higuchi
Keyword(s):  
Tissue Culture ◽  
Ferulic Acid ◽  
Methyl Ketone ◽  
Sinapic Acid ◽  
Lignin Biosynthesis ◽  
Coumaric Acid ◽  
White Pine

The incorporation of phenylalanine-R-C14, p-coumaric acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 into conifer lignin was studied by using tissue culture of white pine. The first three compounds were quite good precursors of conifer lignin. The lignin was degraded by ethanolysis to yield vanilloyl methyl ketone in approximately 0.2% yield of the lignin. When sinapic acid was fed no corresponding syringoyl methyl ketone could be isolated but the vanilloyl methyl ketone was radioactive. This suggests that demethoxylation of sinapyl compounds can occur in lignification. The results show that the enzymes responsible for the biosynthesis of lignin from these precursors are present in the cambium, and that the lignification route via phenylpropanoid acids is operative in this tissue as well as in other species.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: X. FORMATION OF LIGNIN FROM PHENYLPROPANOIDS IN TISSUE CULTURE OF WHITE PINE

1962 ◽  
Vol 40 (1) ◽  
pp. 31-34 ◽  
Author(s):  
Takayoshi Higuchi
Keyword(s):  
Tissue Culture ◽  
Ferulic Acid ◽  
Methyl Ketone ◽  
Sinapic Acid ◽  
Lignin Biosynthesis ◽  
Coumaric Acid ◽  
White Pine

The incorporation of phenylalanine-R-C14, p-coumaric acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 into conifer lignin was studied by using tissue culture of white pine. The first three compounds were quite good precursors of conifer lignin. The lignin was degraded by ethanolysis to yield vanilloyl methyl ketone in approximately 0.2% yield of the lignin. When sinapic acid was fed no corresponding syringoyl methyl ketone could be isolated but the vanilloyl methyl ketone was radioactive. This suggests that demethoxylation of sinapyl compounds can occur in lignification. The results show that the enzymes responsible for the biosynthesis of lignin from these precursors are present in the cambium, and that the lignification route via phenylpropanoid acids is operative in this tissue as well as in other species.

scholarly journals The effects of plant density and irrigation on phenolic content in cauliflower 

2017 ◽  
Vol 44 (No. 4) ◽  
pp. 178-185 ◽  
Author(s):  
Alina Kałużewicz ◽  
Jolanta Lisiecka ◽  
Monika Gąsecka ◽  
Włodzimierz Krzesiński ◽  
Tomasz Spiżewski ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Ferulic Acid ◽  
Gallic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Plant Density ◽  
Phenolic Content ◽  
Sinapic Acid ◽  
Dry Weight ◽  
Coumaric Acid

This study was conducted to study the influence of plant density and irrigation on the content of phenolic compounds, i.e., phenolic acids and flavonols in cv. ‘Sevilla’ cauliflower curds. Levels of phenolic acids and flavonols were in the range of 3.0–6.2 mg and 25.4–87.8 mg/100 g of dry weight, respectively, depending on plant density and irrigation. Of the phenolic acids, caffeic acid was detected in the highest amount, followed by p-coumaric acid, sinapic acid, gallic acid, and ferulic acid. Of the two flavonols detected, the levels of quercetin were higher than those of kaempferol. The content of the detected phenolic acids (with the exception of ferulic acid) and both flavonols increased with increasing plant density. Furthermore, the concentration of phenolic compounds (with the exception of ferulic acid) was significantly higher under irrigation.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XII. THE BIOSYNTHESIS AND METABOLISM OF SINAPIC ACID

1963 ◽  
Vol 41 (3) ◽  
pp. 613-620 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Acrylic Acid ◽  
Ferulic Acid ◽  
Early Stage ◽  
Sinapic Acid ◽  
Lignin Biosynthesis ◽  
Pinus Strobus ◽  
Coniferyl Alcohol ◽  
Tissue Cultures ◽  
Feeding Experiments

Sinapic acid-2-C14 is converted by 25-day-old wheat plants to sinapyl lignin 6 times as efficiently as to coniferyl lignin. This factor rises to 16 in heading wheat, indicating lessened ability to demethoxylate the sinapyl nucleus with increasing age. Feeding experiments with 3-(3,4-dihydroxy-5-methoxyphenyl)-acrylic acid (5-hydroxyferulic acid) provided evidence for the participation of this compound in the conversion of ferulic to sinapic acid. In plants at an early stage of lignification 5-hydroxyferulic acid was dehydroxylated to ferulic acid and was converted to coniferyl lignin, but evidence about the conversion of 5-hydroxyferulic acid to coniferyl lignin in more mature plants was conflicting. Demethylation of sinapic to 5-hydroxyferulic acid was demonstrated by means of a trapping experiment. Ferulic acid-2-C14 is reduced to coniferyl aldehyde and coniferyl alcohol in heading wheat plants and cambial tissue cultures of Pinus strobus.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XI. REACTIONS RELATING TO LIGNIFICATION IN YOUNG WHEAT PLANTS

1963 ◽  
Vol 41 (1) ◽  
pp. 65-76 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Cell Wall ◽  
Ferulic Acid ◽  
Sinapic Acid ◽  
Cumulative Effect ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Cinnamic Acids ◽  
Labelled Compound ◽  
The Difference ◽  
Ferulic Acids

L-Phenylalanine-G-C14, p-hydroxycinnamic acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 were administered to wheat plants aged both 30 and 73 days. Radioactive vanilloyl- and syringoyl-methyl ketones were then recovered after ethanolysis of the cell wall residues. When corrected for differences in endogenous lignin, the C14 dilution values calculated for the younger plants were generally greater, indicating, as expected, a slower rate of lignification. The difference between the younger and older plants was less for sinapic and ferulic acids than for p-hydroxycinnamic acid or phenylalanine. This suggested that slower lignification in young plants may be due not to relative inactivity of an enzyme system at any one stage of the biosynthetic pathway but to the cumulative effect of slower reactions at several stages. Sinapic acid is converted in the younger plants to lignin yielding vanilloyl-, as well as syringoyl-, methyl ketone, suggesting a demethoxylation. Glucose esters of the radioactive phenolic cinnamic acids corresponding to the labelled compound administered were recovered from the plant extracts. A small percentage of the activity in the cell wall residue was in the form of ferulic acid joined by ester linkages.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XI. REACTIONS RELATING TO LIGNIFICATION IN YOUNG WHEAT PLANTS

1963 ◽  
Vol 41 (1) ◽  
pp. 65-76 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Cell Wall ◽  
Ferulic Acid ◽  
Sinapic Acid ◽  
Cumulative Effect ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Cinnamic Acids ◽  
Labelled Compound ◽  
The Difference ◽  
Ferulic Acids

L-Phenylalanine-G-C14, p-hydroxycinnamic acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 were administered to wheat plants aged both 30 and 73 days. Radioactive vanilloyl- and syringoyl-methyl ketones were then recovered after ethanolysis of the cell wall residues. When corrected for differences in endogenous lignin, the C14 dilution values calculated for the younger plants were generally greater, indicating, as expected, a slower rate of lignification. The difference between the younger and older plants was less for sinapic and ferulic acids than for p-hydroxycinnamic acid or phenylalanine. This suggested that slower lignification in young plants may be due not to relative inactivity of an enzyme system at any one stage of the biosynthetic pathway but to the cumulative effect of slower reactions at several stages. Sinapic acid is converted in the younger plants to lignin yielding vanilloyl-, as well as syringoyl-, methyl ketone, suggesting a demethoxylation. Glucose esters of the radioactive phenolic cinnamic acids corresponding to the labelled compound administered were recovered from the plant extracts. A small percentage of the activity in the cell wall residue was in the form of ferulic acid joined by ester linkages.

scholarly journals Improving the catalytic characteristics of phenolic acid decarboxylase from Bacillus amyloliquefaciens by the engineering of N-terminus and C-terminus

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Qin Li ◽  
Ying Xia ◽  
Ting Zhao ◽  
Yuanyuan Gong ◽  
Shangling Fang ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Phenolic Acid ◽  
Bacillus Amyloliquefaciens ◽  
Sinapic Acid ◽  
Alkali Resistance ◽  
Acid Decarboxylase ◽  
Coumaric Acid ◽  
C Terminus ◽  
N Terminus ◽  
Phenolic Acid Decarboxylase

Abstract Background 4-vinylphenols produced by phenolic acid degradation catalyzed by phenolic acid decarboxylase can be used in food additives as well as flavor and fragrance industry. Improving the catalytic characters of phenolic acid decarboxylase is of great significance to enhance its practical application. Results A phenolic acid decarboxylase (P-WT) was created from Bacillus amyloliquefaciens ZJH-01. Mutants such as P-C, P-N, P-m1, P-m2, P-Nm1, and P-Nm2 were constructed by site-directed mutagenesis of P-WT. P-C showed better substrate affinities and higher turnover rates than P-WT for p-coumaric acid, ferulic acid, and sinapic acid; however, P-N had reduced affinity toward p-coumaric acid. The extension of the C-terminus increased its acid resistance, whereas the extension of the N-terminus contributed to the alkali resistance and heat resistance. The affinity of P-m1 to four substrates and that of P-m2 to p-coumaric acid and ferulic acid were greatly improved. However, the affinity of P-Nm2 to four phenolic acids was greatly reduced. The residual enzyme activities of P-Nm1 and P-Nm2 considerably improved compared with those of P-m1 and P-m2 after incubation at 50 °C for 60 min. Conclusions The extension of the N-terminus may be more conducive to the combination of the binding cavity with the substrate in an alkaline environment and may make its structure more stable.

scholarly journals Role of Salicylic Acid and Components of the Phenylpropanoid Pathway in Basal and Cultivar-Related Resistance of Oilseed Rape (Brassica napus) to Verticillium longisporum

Plants ◽  
2019 ◽  
Vol 8 (11) ◽  
pp. 491 ◽  
Author(s):  
Xiaorong Zheng ◽  
Birger Koopmann ◽  
Andreas von Tiedemann
Keyword(s):  
Salicylic Acid ◽  
Brassica Napus ◽  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Sinapic Acid ◽  
Coumaric Acid ◽  
Basal Resistance ◽  
Remarkable Increase ◽  
Verticillium Longisporum

Enhanced resistance is a key strategy of controlling ‘Verticillium stem striping’ in Brassica napus caused by the soil-borne vascular pathogen Verticillium longisporum. The present study analyses the role of a broad range of components in the phenylpropanoid and salicylic acid (SA) pathways in basal and cultivar-related resistance of B. napus towards V. longisporum. A remarkable increase of susceptibility to V. longisporum in SA-deficient transgenic NahG plants indicated an essential role of SA in basal resistance of B. napus to V. longisporum. Accordingly, elevated SA levels were also found in a resistant and not in a susceptible cultivar during early asymptomatic stages of infection (7 dpi), which was associated with increased expression of PR1 and PR2. In later symptomatic stages (14 or 21 dpi), SA responses did not differ anymore between cultivars varying in resistance. In parallel, starting at 7 dpi, an overall increase in phenylpropanoid syntheses developed in the resistant cultivar, including the activity of some key enzymes, phenylalanine ammonium lyase (PAL), cinnamyl alcohol dehydrogenase (CAD) and peroxidase (POX) and the expression of key genes, PAL4, CCoAMT, CCR, POX. As a consequence, a remarkable increase in the levels of phenolic acids (t-cinnamic acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid) occurred associated with cultivar resistance. A principal component analysis including all 27 traits studied indicated that component 1 related to SA synthesis (PR1, PR2, POX, level of free SA) and component 2 related to lignin synthesis (level of free ferulic acid, free p-coumaric acid, conjugated t-cinnamic acid) were the strongest factors to determine cultivar-related resistance. This study provides evidence that both SA and phenolic acid synthesis are important in cultivar-related resistance, however, with differential roles during asymptomatic and symptomatic stages of infection.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XII. THE BIOSYNTHESIS AND METABOLISM OF SINAPIC ACID

1963 ◽  
Vol 41 (1) ◽  
pp. 613-620 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Acrylic Acid ◽  
Ferulic Acid ◽  
Early Stage ◽  
Sinapic Acid ◽  
Lignin Biosynthesis ◽  
Pinus Strobus ◽  
Coniferyl Alcohol ◽  
Tissue Cultures ◽  
Feeding Experiments

Sinapic acid-2-C14 is converted by 25-day-old wheat plants to sinapyl lignin 6 times as efficiently as to coniferyl lignin. This factor rises to 16 in heading wheat, indicating lessened ability to demethoxylate the sinapyl nucleus with increasing age. Feeding experiments with 3-(3,4-dihydroxy-5-methoxyphenyl)-acrylic acid (5-hydroxyferulic acid) provided evidence for the participation of this compound in the conversion of ferulic to sinapic acid. In plants at an early stage of lignification 5-hydroxyferulic acid was dehydroxylated to ferulic acid and was converted to coniferyl lignin, but evidence about the conversion of 5-hydroxyferulic acid to coniferyl lignin in more mature plants was conflicting. Demethylation of sinapic to 5-hydroxyferulic acid was demonstrated by means of a trapping experiment. Ferulic acid-2-C14 is reduced to coniferyl aldehyde and coniferyl alcohol in heading wheat plants and cambial tissue cultures of Pinus strobus.

scholarly journals Improving the catalytic characteristics of phenolic acid decarboxylase from Bacillus amyloliquefaciens by the engineering of N-terminus and C-terminus

2020 ◽  
Author(s):  
Qin Li ◽  
Ying Xia ◽  
Ting Zhao ◽  
Yuanyuan Gong ◽  
Shangling Fang ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Phenolic Acid ◽  
Food Additives ◽  
Sinapic Acid ◽  
Alkali Resistance ◽  
Acid Decarboxylase ◽  
Coumaric Acid ◽  
C Terminus ◽  
N Terminus ◽  
Phenolic Acid Decarboxylase

Abstract Background: 4-vinylphenols produced by phenolic acid degradation catalyzed by phenolic acid decarboxylase can be used in food additives as well as flavor and fragrance industry. Improving the catalytic characters of phenolic acid decarboxylase is of great significance to enhance its practical application. Results: Mutants such as P-C, P-N, P-m1, P-m2, P-Nm1, and P-Nm2 were constructed by site-directed mutagenesis of P-WT. P-C showed better substrate affinities and higher turnover rates than P-WT for p-coumaric acid, ferulic acid, and sinapic acid; however, P-N had reduced affinity toward p-coumaric acid. The extension of the C-terminus increased its acid resistance, whereas the extension of the N-terminus contributed to the alkali resistance and heat resistance. The affinity of P-m1 to four substrates and that of P-m2 to p-coumaric acid and ferulic acid were greatly improved. However, the affinity of P-Nm2 to four phenolic acids was greatly reduced. The residual enzyme activities of P-Nm1 and P-Nm2 considerably improved compared with those of P-m1 and P-m2 after incubation at 50°C for 60 min.Conclusions: The extension of the N-terminus may be more conducive to the combination of the binding cavity with the substrate in an alkaline environment and may make its structure more stable.

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