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: 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.

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.

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.

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 Effect of Different Processing Methods on the Accumulation of the Phenolic Compounds and Antioxidant Profile of Broomcorn Millet (Panicum miliaceum L.) Flour

Foods ◽  
2019 ◽  
Vol 8 (7) ◽  
pp. 230 ◽  
Author(s):  
Md Obyedul Kalam Azad ◽  
Da In Jeong ◽  
Md Adnan ◽  
Timnoy Salitxay ◽  
Jeong Won Heo ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Radical Scavenging ◽  
Sinapic Acid ◽  
Secondary Compounds ◽  
Syringic Acid ◽  
Total Phenolic ◽  
Panicum Miliaceum ◽  
Processing Methods ◽  
Antioxidant Power ◽  
Broomcorn Millet

Broomcorn millet (Panicum miliaceum L.) is an important nutritious ancient minor-cereal food crop. However, this crop is little explored in the food processing arena to improve its functionality. In this context, different processing methods were applied to enhance the secondary compounds of broomcorn millet. Four different individual methods such as roasting, steaming, puffing, and extrusion were applied at 110 °C to enhance the functional attributes of millet flour. It was observed that the significantly highest content of total phenolic (TP) (670 mg/100 g of ferulic acid equivalent) and total flavonoid (TF) (391 mg/100 g of rutin equivalent ) was attained in the roasted whole millet followed by steaming (315 mg/100 g, 282 mg/100 g), puffing (645 mg/100 g, 304 mg/100 g), extrusion (455 mg/100 g, 219 mg/100 g), and control (295 mg/100 g, 183 mg/100 g). The chromatographic analysis showed a greater content of single phenolic acids such as syringic acid, gallic acid, 4-hydroxy benzoic acid, ferulic acid, sinapic acid, and catechin in roasted millet compared to control, and the content of each acid was higher in whole millet than dehulled. Results also indicated that the content of ferulic acid was relatively higher among the quantified single phenolic acid from broomcorn millet. Likewise, in comparison with dehulled millet, the roasted whole millet showed higher total antioxidant capacity, measured by the 2,2-diphenyl-1 picryl hydrazyl (DPPH), the ferric reducing antioxidant power assay (FRAP), the phosphomolybdenum method (PPMD), and the hydroxyl radical scavenging capacity (HRSC) method. Lastly, it is concluded that the roasting method should be taken into consideration in the processing of broomcorn millet to enhance the content of nutraceutical compounds and improve its functionality.

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