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: 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.

Involvement of Phenolics, Flavonoids, and Phenolic Acids in High Yield Characteristics of Rice (Oryza Sativa L.)

2018 ◽  
Vol 68 ◽  
pp. 19-26 ◽  
Author(s):  
Tran Dang Xuan ◽  
Do Tuan Bach ◽  
Tran Dang Dat
Keyword(s):  
Ferulic Acid ◽  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Sinapic Acid ◽  
Development Stage ◽  
Vegetative Stage ◽  
High Yield ◽  
Phenolic Contents ◽  
The Difference

The present study examined the correlation between phenolic acids and flavonoids with high rice yield traits of rice. It was observed that the difference of phenolic contents among the tested rice lines occurred only in the vegetative stage. The concentrations of phenolic acids were higher in the rice high yield cultivars than low yield variety in the vegetative stage, but they either decreased dramatically or disappeared during the development stage. Caffeic acid was found only in high yield rice, whereas chlorogenic acid was detected only in low yield rice. Sinapic acid was the dominant phenolic acid in high yield cultivars at vegetative stage (3.7 mg/g), followed by ferulic acid (1.2 mg/g). These findings suggest that caffeic acid, ferulic acid, sinapic acid and chlorogenic acid may play a particular role in forming yield components in rice. The cultivar B3 contained high amount of sinapic acid may be used as a natural source for pharmaceutical use.

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.

scholarly journals Integrated Omics Analyses Identify Key Pathways Involved in Petiole Rigidity Formation in Sacred Lotus

2020 ◽  
Vol 21 (14) ◽  
pp. 5087
Author(s):  
Ming Li ◽  
Ishfaq Hameed ◽  
Dingding Cao ◽  
Dongli He ◽  
Pingfang Yang
Keyword(s):  
Cell Wall ◽  
Lignin Biosynthesis ◽  
Enrichment Analysis ◽  
Differentially Expressed ◽  
Pathway Enrichment Analysis ◽  
Anatomic Structure ◽  
Sacred Lotus ◽  
Expression Of Genes ◽  
The Difference ◽  
Key Pathways

Sacred lotus (Nelumbo nucifera Gaertn.) is a relic aquatic plant with two types of leaves, which have distinct rigidity of petioles. Here we assess the difference from anatomic structure to the expression of genes and proteins in two petioles types, and identify key pathways involved in petiole rigidity formation in sacred lotus. Anatomically, great variation between the petioles of floating and vertical leaves were observed. The number of collenchyma cells and thickness of xylem vessel cell wall was higher in the initial vertical leaves’ petiole (IVP) compared to the initial floating leaves’ petiole (IFP). Among quantified transcripts and proteins, 1021 and 401 transcripts presented 2-fold expression increment (named DEGs, genes differentially expressed between IFP and IVP) in IFP and IVP, 421 and 483 proteins exhibited 1.5-fold expression increment (named DEPs, proteins differentially expressed between IFP and IVP) in IFP and IVP, respectively. Gene function and pathway enrichment analysis displayed that DEGs and DEPs were significantly enriched in cell wall biosynthesis and lignin biosynthesis. In consistent with genes and proteins expressions in lignin biosynthesis, the contents of lignin monomers precursors were significantly different in IFP and IVP. These results enable us to understand lotus petioles rigidity formation better and provide valuable candidate genes information on further investigation.

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.

Phenolic acids in the fibre of some tropical grasses, effect on feed quality, and their metabolism by sheep

1993 ◽  
Vol 44 (5) ◽  
pp. 1123 ◽  
Author(s):  
JB Lowry ◽  
EA Sumpter ◽  
CS McSweeney ◽  
AC Schlink ◽  
B Bowden
Keyword(s):  
Cell Wall ◽  
Phenolic Acids ◽  
Hippuric Acid ◽  
Nitrogen Loss ◽  
Sinapic Acid ◽  
Coumaric Acid ◽  
Tropical Grasses ◽  
Dry Matter Loss ◽  
Ferulic Acids

A feature of the composition of dry-season tropical grasses, which may in part account for their lower digestibility, is the relatively high content of hydroxycinnamic acids covalently bound in the cell wall. The main phenolic acids liberated on mild alkaline hydrolysis in 19 species of native and introduced grasses in North Queensland were p-coumaric and ferulic acids, with the former predominating in 16 species. Caffeic acid was found in three species and sinapic acid in trace amounts. Total acids occurred at approximately 10 g/kg in most species, but were found at 50 g/kg in one species. When five of the species were fed as the sole diet to sheep, intake and digestibility were not clearly related to phenolic acid level in the diet. However, output of hippuric acid in the urine increased with the daily dietary intake of phenolic acids, and nitrogen excreted as hippurate was equivalent to as much as 17% of the total nitrogen in the diet. The effect of free acids on rumen function was tested by adding p-coumaric and ferulic acid directly to the diet. In contrast to the implications of numerous in vitro studies, intake and digestibility were not affected. Dry matter loss from intraruminal nylon bags was also not affected by administration of these compounds. In addition to hippuric acid, cinnamoylglycine was identified as a urinary metabolite. This appeared in animals on most of the grass diets, and was enhanced following administration of ferulic or p-coumaric acid, but not benzoic acid. It seems that phenolic acids liberated from the cell wall are unlikely to have an adverse effect on rumen microbial metabolism, but impose a serious nitrogen loss for animals on diets already deficient in nitrogen.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: VII. THE ROLE OF p-HYDROXYPHENYLPYRUVIC ACID

1959 ◽  
Vol 37 (1) ◽  
pp. 25-34 ◽  
Author(s):  
Stewart A. Brown ◽  
D. Wright ◽  
A. C. Neish
Keyword(s):  
Specific Activity ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Nitrobenzene Oxidation ◽  
Salvia Splendens ◽  
Ferulic Acids ◽  
Related Compounds ◽  
Unique Ability ◽  
Good Precursor

L-Phenylalanine-C14 and p-hydroxyphenylpyruvic acid-3-C14 were administered to wheat, buckwheat, and salvia (Salvia splendens Sello), and after 24 hours the "lignin aldehydes" (p-hydroxybenzaldehyde, vanillin, and syringaldehyde) were isolated following alkaline nitrobenzene oxidation of the plant fraction insoluble in ethanol–benzene and water. Although all species converted phenylalanine readily to lignin, only wheat could form the syringyl and guaiacyl parts of lignin efficiently from p-hydroxyphenylpyruvic acid. p-Hydroxybenzaldehyde recovered from all species was heavily labelled after feeding both compounds. The L-tyrosine from acid hydrolysis and the p-hydroxybenzaldehyde from nitrobenzene oxidation, isolated from buckwheat activated by feeding p-hydroxyphenylpyruvic acid-3-C14, had the same molar specific activity, and it is considered probable that most if not all of the p-hydroxybenzaldehyde in all these species was derived from protein tyrosine in the extracted residue. When p-hydroxyphenyllactic acid-3-C14 was metabolized by wheat all the aldehydes were labelled, but none possessed measurable radioactivity when this compound was administered to buckwheat. Consequently, neither p-hydroxyphenylpyruvic nor p-hydroxyphenyllactic acid is a general intermediate in lignification, and differences noted here and in previous papers between grasses and non-grasses probably result from the unique ability of grasses to convert p-hydroxyphenyllactic acid to p-hydroxycinnamic acid. This idea is supported by the ability of wheat to form p-hydroxycinnamic and ferulic acids readily from both phenylalanine and tyrosine, whereas only phenylalanine is a good precursor of these acids in salvia. A scheme is presented showing the metabolic interconversions of phenylpropanoid acids and related compounds leading to lignin.

scholarly journals Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation

2000 ◽  
Vol 66 (12) ◽  
pp. 5322-5328 ◽  
Author(s):  
Sylvie van Beek ◽  
Fergus G. Priest
Keyword(s):  
Ferulic Acid ◽  
Lactobacillus Brevis ◽  
Hydroxycinnamic Acid ◽  
Final Concentration ◽  
Acid Decarboxylase ◽  
Yeast Fermentation ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Pure Cultures ◽  
Malt Whisky

ABSTRACT Seven strains of Lactobacillus isolated from malt whisky fermentations and representing Lactobacillus brevis,L. crispatus, L. fermentum, L. hilgardii, L. paracasei, L. pentosus, andL. plantarum contained genes for hydroxycinnamic acid (p-coumaric acid) decarboxylase. With the exception ofL. hilgardii, these bacteria decarboxylatedp-coumaric acid and/or ferulic acid, with the production of 4-vinylphenol and/or 4-vinylguaiacol, respectively, although the relative activities on the two substrates varied between strains. The addition of p-coumaric acid or ferulic acid to cultures ofL. pentosus in MRS broth induced hydroxycinnamic acid decarboxylase mRNA within 5 min, and the gene was also induced by the indigenous components of malt wort. In a simulated distillery fermentation, a mixed culture of L. crispatus and L. pentosus in the presence of Saccharomyces cerevisiae decarboxylated added p-coumaric acid more rapidly than the yeast alone but had little activity on added ferulic acid. Moreover, we were able to demonstrate the induction of hydroxycinnamic acid decarboxylase mRNA under these conditions. However, in fermentations with no additional hydroxycinnamic acid, the bacteria lowered the final concentration of 4-vinylphenol in the fermented wort compared to the level seen in a pure-yeast fermentation. It seems likely that the combined activities of bacteria and yeast decarboxylate p-coumaric acid and then reduce 4-vinylphenol to 4-ethylphenol more effectively than either microorganism alone in pure cultures. Although we have shown that lactobacilli participate in the metabolism of phenolic compounds during malt whisky fermentations, the net result is a reduction in the concentrations of 4-vinylphenol and 4-vinylguaiacol prior to distillation.

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.

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