THE PHENOLIC ACIDS IN WHEAT: I. CHANGES DURING GROWTH AND DEVELOPMENT

1964 ◽  
Vol 42 (2) ◽  
pp. 203-210 ◽  
Author(s):  
Said El-Basyouni ◽  
G. H. N. Towers
Keyword(s):  
Cell Wall ◽  
Phenolic Acids ◽  
Growth And Development ◽  
Soluble Fraction ◽  
Sinapic Acid ◽  
Wheat Plant ◽  
Ethanolic Extracts ◽  
Ferulic Acids ◽  
Natural Precursor ◽  
Wheat Tissues

Quantitative determinations were made of p-coumaric, ferulic, caffeic, sinapic, p-hydroxybenzoic, vanillic, and syringic acids which occur as alkali- and acid-hydrolyzable derivatives in ethanolic extracts of wheat tissues. The ethanol-insoluble (cell wall) residues also yielded phenolic acids on cold alkaline hydrolysis. Comparatively large quantities of p-coumaric and ferulic acids (1.8 mg/g dry wt, and 4 mg/g dry wt., respectively, in 25-day-old shoots) were obtained from this fraction, the amounts depending on the age of the tissue. Phenolic acids in the ethanol-soluble fraction reached a maximum concentration about 9 days after germination. The amounts fell off with increasing age, reaching a minimum 4 to 5 weeks later. There was no obvious relationship between the amounts of these acids as reported here and rates of lignification as reported for the wheat plant by others. The behavior of sinapic acid was markedly different from that of p-coumaric and ferulic acids and it is suggested that it may not be a natural precursor of the syringyl units of lignin.

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: 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 Concentrations of Phenolic Acids Are Differently Genetically Determined in Leaves, Flowers, and Grain of Common Buckwheat (Fagopyrum esculentum Moench)

Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1142
Author(s):  
Alena Vollmannová ◽  
Janette Musilová ◽  
Judita Lidiková ◽  
Július Árvay ◽  
Marek Šnirc ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Phenolic Acids ◽  
Sinapic Acid ◽  
Fagopyrum Esculentum ◽  
Blood Cholesterol ◽  
Common Buckwheat ◽  
High Concentration ◽  
Phenolic Substances ◽  
Fagopyrum Esculentum Moench

Common buckwheat (Fagopyrum esculentum Moench) is a valuable source of proteins, B vitamins, manganese, tryptophan, phytochemicals with an antioxidant effect, and the natural flavonoid rutin. Due to its composition, buckwheat supports the human immune system, regulates blood cholesterol, and is suitable for patients with diabetes or celiac disease. The study aimed to compare the allocation of selected phenolic acids (neochlorogenic acid, chlorogenic acid, trans-caffeic acid, trans-p-coumaric acid, trans-sinapic acid, trans-ferulic acid) and flavonoids (rutin, vitexin, quercetin, kaempferol) in the leaves, flowers, and grain of buckwheat cultivars of different origin. The content of individual phenolics was determined by the HPLC-DAD method. The results confirmed the determining role of cultivar on the relative content of chlorogenic acid, trans-caffeic acid, trans-sinapic acid, vitexin, and kaempferol in buckwheat plants. A significantly negative correlation among concentrations of phenolic acids in different common buckwheat plant parts shows that there are different mechanisms of genetic influences on the concentration of phenolic substances in common buckwheat flowers, leaves, and grain. These differences should be taken into account when breeding buckwheat for a high concentration of selected phenolic substances.

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.

Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid and UDP-Glucose by a Cell-Free System from Raphanus sativus Seedlings

1980 ◽  
Vol 35 (3-4) ◽  
pp. 204-208 ◽  
Author(s):  
Dieter Strack
Keyword(s):  
Phenolic Acids ◽  
Enzymatic Synthesis ◽  
Raphanus Sativus ◽  
High Performance ◽  
Sinapic Acid ◽  
Carboxyl Group ◽  
Ph Optimum ◽  
Free System ◽  
Sh Group ◽  
A Cell

Abstract Protein extracts from seedlings of Raphanus sativus catalyze the transfer of the glucosyl moiety of UDP-glucose to the carboxyl group of phenolic acids. Enzymatic activity was determined spectrophotometrically by measuring the increase in absorbance at 360 nm and/or by the aid of high performance liquid chromatography (HPLC). From 12 phenolic acids tested as acceptors, sinapic acid was by far the best substrate. The glucosyltransfer to sinapic acid has a pH optimum near 7 and requires as SH group for activity, p-Chloromercuribenzoate (PCMB) inhibits activity, which can be restored by the addition of dithiothreitol (DTT). The formation of 1-sinapoylglucose was found to be a reversible reaction, since the addition of UDP results in a breakdown of the ester.

Impact of plant cell wall network on biodegradation in soil: Role of lignin composition and phenolic acids in roots from 16 maize genotypes

2011 ◽  
Vol 43 (7) ◽  
pp. 1544-1552 ◽  
Author(s):  
Gaylord Erwan Machinet ◽  
Isabelle Bertrand ◽  
Yves Barrière ◽  
Brigitte Chabbert ◽  
Sylvie Recous
Keyword(s):  
Cell Wall ◽  
Plant Cell ◽  
Phenolic Acids ◽  
Plant Cell Wall ◽  
Maize Genotypes ◽  
Lignin Composition ◽  
Biodegradation In Soil

The role of Golgi bodies in polysaccharide sulphation in Fucuszygotes

1978 ◽  
Vol 32 (1) ◽  
pp. 337-356
Author(s):  
M.E. Callow ◽  
S.J. Coughlan ◽  
L.V. Evans
Keyword(s):  
Cell Wall ◽  
Alginic Acid ◽  
Soluble Fraction ◽  
Amorphous Layer ◽  
Acceptor Molecule ◽  
Golgi Bodies ◽  
Isolation And Characterization ◽  
Fucus Serratus

The cell wall of 24-h zygotes of Fucus serratus is composed of 3 layers—an inner fibrillar layer (sulphated fucan), an outer fibrillar layer (alginic aicd/cellulose) and an exterior amorphous layer (sulphated fucan, alginic acid). The 2 layers containing sulphated fucan are preferentially thickened at the rhizoid pole. Light- and electron-microscope autoradiographic pulse-chase experiments on 22-h zygotes using 35SO2-(4) show the Golgi bodies to be the sites of fucan sulphation. The isolation and characterization of isolated Golgi-rich fractions from 22-h zygotes shows that the first detectable labelled macromolecule is associated with these fractions 2 min after addition of 35SO2-(4). The sulphate acceptor molecule has been partially characterized. 35S-APS and 35S-paps are detectable in the soluble fraction 0.5 min after addition of 35SO2-(4). The results are discussed in relation to other published work on the differentiation of Fucus embryos and on polysaccharide sulphation.

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.

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