Zur Biosynthese der Benzoesäure in Gaultheria procumbens L. II

1964 ◽  
Vol 19 (9) ◽  
pp. 781-783 ◽  
Author(s):  
Hans Grisebach ◽  
Karl-Otto Vollmer
Keyword(s):  
Salicylic Acid ◽  
Cinnamic Acid ◽  
Protocatechuic Acid ◽  
Total Activity ◽  
Syringic Acid ◽  
The Other ◽  
Carboxyl Group ◽  
Hydroxybenzoic Acid ◽  
Benzoic Acids ◽  
Gaultheria Procumbens

Further investigations on the biosynthesis of benzoic acids in Gaultheria procumbens L. have shown that besides salicylic acid all the other benzoic acids (gentisinic acid, p-hydroxybenzoic acid, protocatechuic acid, o-pyrocatechuic acid(?), syringic acid and vanillinic acid) can be formed from cinnamic acid. In the case of vanillinic acid it was proved that the total activity is located in the carboxyl group when cinnamic acid-[3-14C] is the precursor.Formiat-14C is incorporated into the methylester group of methylsalicylate.

scholarly journals Untersuchungen zur Biosynthese des Salicylsäuremethylesters in Gaultheria procumbeus L

1963 ◽  
Vol 18 (9) ◽  
pp. 753-756 ◽  
Author(s):  
Hans Grisebach ◽  
Karl-Otto Vollmer
Keyword(s):  
Salicylic Acid ◽  
Essential Oil ◽  
Cinnamic Acid ◽  
Total Radioactivity ◽  
Carboxyl Group ◽  
Young Leaves ◽  
Gaultheria Procumbens

Acetate-[1-14C] and cinnamic acid-[3-14C] were administered to young leaves of Gaultheria procumbens L. The methylsalicylate isolated from the essential oil was radioactive only with cinnamic acid-[3-14C] as the precursor. Decarboxylation of the salicylic acid showed that the total radioactivity was located in the carboxyl group. Salicylic acid must therefore be regarded as a metabolite of cinnamic acid.

PHENOLIC COMPOUNDS IN FERNS: I. A SURVEY OF SOME FERNS FOR CINNAMIC ACID AND BENZOIC ACID DERIVATIVES

1967 ◽  
Vol 45 (5) ◽  
pp. 585-593 ◽  
Author(s):  
Bruce A. Bohm ◽  
Rolla M. Tryon
Keyword(s):  
Phenolic Compounds ◽  
Protocatechuic Acid ◽  
Sinapic Acid ◽  
Syringic Acid ◽  
Hydroxybenzoic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Benzoic Acid Derivatives ◽  
Dennstaedtia Punctilobula

Forty-six ferns, representing 28 genera and 8 families, were examined for hydroxylated cinnamic acids and benzoic acids. In most plants examined the "basic complement" of cinnamic acids, p-coumaric, caffeic, and ferulic, was present. In these plants p-hydroxybenzoic acid, protocatechuic acid, and vanillic acid were generally also present. Of much more limited distribution were sinapic acid, syringic acid, and o-coumaric acid. Coumarin was shown to be present in Dennstaedtia punctilobula, the only fern tested which possessed this type of compound. The data available from three ferns reported in the literature are also included in this survey; one represents an additional family and one represents an additional genus.An experiment with DL-phenylalanine-1-14C and DL-phenylalanine-3-14C and Cyathea arborea showed the incorporation of label into p-coumaric acid, caffeic acid, and ferulic acid.

Biosynthese von p-Hydroxybenzoesäure und anderer Benzoesäuren in höheren Pflanzen

1964 ◽  
Vol 19 (5) ◽  
pp. 398-405 ◽  
Author(s):  
M. H. Zenk ◽  
G. Müller
Keyword(s):  
Benzoic Acid ◽  
Protocatechuic Acid ◽  
Higher Plants ◽  
Side Chain ◽  
Hydroxybenzoic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Feeding Experiments ◽  
Catalpa Ovata

Feeding experiments with glucose- (2-14C), phenylalanine- (3-14C), tyrosine- (3-14C) and p-coumaric acid- (3-14C) showed that the latter three substances are incorporated in good yields into p-hydroxybenzoic acid in leaves of Catalpa ovata. Kinetic experiments showed that p-hydroxybenzoic acid is formed from phenylalanine via p-coumaric acid and the subsequent β-oxidation of the side chain. p-Hydroxybenzoic acid can also be synthetised by hydroxylation of benzoic acid, but this does not seem to be the biosynthetic route in Catalpa.Phenylalanine- (3-14C) is also incorporated into benzoic acid, protocatechuic acid, and vanillic acid by different plants; the radioactivity of the β-C atom of the amino acid was found in each case to be located in the carboxyl group of the C6 — C1 acid. This suggests that in higher plants the benzoic acids are formed from the corresponding cinnamic acids via β-oxidation.

Zur Biosynthese der Benzoesäuren in Gaultheria procumbens III

1966 ◽  
Vol 21 (5) ◽  
pp. 435-439 ◽  
Author(s):  
Karl-Otto Vollmer ◽  
Hans Grisebach
Keyword(s):  
Gas Chromatography ◽  
Thin Layer ◽  
Silicic Acid ◽  
Cinnamic Acid ◽  
Vanillic Acid ◽  
Benzoic Acids ◽  
Coumaric Acid ◽  
Gentisic Acid ◽  
Gaultheria Procumbens

The cinnamic and benzoic acids present in Gaultheria procumbens could be separated by a combination of thin layer, paper, silicic acid, and gas chromatography. After administration of cinnamic-, o-coumaric-, and p-coumaric acid-[3-14C] to this plant, the amount of radioactivity in salicylic, p-hydroxybenzoic, gentisic, protocatechuic, and vanillic acid was quantitatively compared. Whereas all five of the latter acids were radioactive with cinnamic acid as the precursor, onky salicylic and gentisic acid contained radioactivity after administration of o-coumaric acid and only p-hydroxybenzoic, protocatechuic, and vanillic acid were radioactive with p-coumaric acid as the precursor. The results show that the hydroxylation pattern of the benzoic acids can be determined at the cinnamic acid stage.

scholarly journals Aerobic Metabolism of 4-Hydroxybenzoic Acid in Archaea via an Unusual Pathway Involving an Intramolecular Migration (NIH Shift)

2002 ◽  
Vol 68 (12) ◽  
pp. 6246-6255 ◽  
Author(s):  
D. J. Fairley ◽  
D. R. Boyd ◽  
N. D. Sharma ◽  
C. C. R. Allen ◽  
P. Morgan ◽  
...  
Keyword(s):  
Protocatechuic Acid ◽  
Cell Suspensions ◽  
Proton Nuclear Magnetic Resonance ◽  
Gas Chromatography Mass Spectrometry ◽  
Structural Isomer ◽  
Resonance Spectroscopy ◽  
Carboxyl Group ◽  
Hydroxybenzoic Acid ◽  
Group Migration ◽  
Do So

ABSTRACT A novel haloarchaeal strain, Haloarcula sp. strain D1, grew aerobically on 4-hydroxybenzoic acid (4HBA) as a sole carbon and energy source and is the first member of the domain Archaea reported to do so. Unusually, D1 metabolized 4HBA via gentisic acid rather than via protocatechuic acid, hydroquinone, or catechol. Gentisate was detected in 4HBA-grown cultures, and gentisate 1,2-dioxygenase activity was induced in 4HBA-grown cells. Stoichiometric accumulation of gentisate from 4HBA was demonstrated in 4HBA-grown cell suspensions containing 2,2′-dipyridyl (which strongly inhibits gentisate 1,2-dioxygenase). To establish whether initial 1-hydroxylation of 4HBA with concomitant 1,2-carboxyl group migration to yield gentisate occurred, 2,6-dideutero-4HBA was synthesized and used as a substrate. Deuterated gentisate was recovered from cell suspensions and identified as 3-deutero-gentisate, using gas chromatography-mass spectrometry and proton nuclear magnetic resonance spectroscopy. This structural isomer would be expected only if a 1,2-carboxyl group migration had taken place, and it provides compelling evidence that the 4HBA pathway in Haloarcula sp. strain D1 involves a hydroxylation-induced intramolecular migration. To our knowledge, this is the first report of a pathway which involves such a transformation (called an NIH shift) in the domain Archaea.

scholarly journals Degradation of phenylalanine and tyrosine by Sporobolomyces roseus

1968 ◽  
Vol 106 (2) ◽  
pp. 507-514 ◽  
Author(s):  
Keith Moore ◽  
P. V. Subba Rao ◽  
G. H. N. Towers
Keyword(s):  
Benzoic Acid ◽  
Caffeic Acid ◽  
Cinnamic Acid ◽  
Protocatechuic Acid ◽  
Acid Metabolism ◽  
Hydroxybenzoic Acid ◽  
Coumaric Acid ◽  
Tracer Studies ◽  
Lyase Activity ◽  
Sporobolomyces Roseus

Ammonia-lyase activity for l-phenylalanine, m-hydroxyphenylalanine and l-tyrosine was demonstrated in cell-free extracts of Sporobolomyces roseus. Cultures of this organism converted dl-[ring−14C]phenylalanine and l-[U−14C]tyrosine into the corresponding cinnamic acid. Tracer studies showed that these compounds were further metabolized to [14C]protocatechuic acid. Benzoic acid and p-hydroxybenzoic acid were intermediates in this pathway. Washed cells of the organism readily utilized cinnamic acid, p-coumaric acid, caffeic acid, benzoic acid and p-hydroxybenzoic acid. Protocatechuic acid was the terminal aromatic compound formed during the metabolism of these compounds. The cells of S. roseus were able to convert m-coumaric acid into m-hydroxybenzoic acid, but the latter compound, which accumulated in the medium, was not further metabolized. 4-Hydroxycoumarin was identified as the product of o-coumaric acid metabolism by this organism.

Polyphenolic composition of grape stems

2020 ◽  
Vol 48 (3) ◽  
pp. 1543-1559
Author(s):  
Bozena PRUSOVA ◽  
Josef LICEK ◽  
Michal KUMSTA ◽  
Mojmir BARON ◽  
Jiri SOCHOR
Keyword(s):  
Antioxidant Activity ◽  
Protocatechuic Acid ◽  
Activity Concentration ◽  
Ammonia Nitrogen ◽  
Syringic Acid ◽  
Polyphenolic Compounds ◽  
Hydroxybenzoic Acid ◽  
Coumaric Acid ◽  
Total Polyphenols ◽  
Polyphenolic Composition

This study is focused on the study of polyphenolic compounds in grape stems as by-product of winemaking industry. Two white varieties of Grüner Veltliner and Sauvignon and two red varieties of Blauer Portugieser and Cabernet Moravia were selected for the study. Antioxidant activity, concentration of total polyphenols and concentration of individual phenolic compounds were determined. The results show a higher concentration of polyphenols and higher values of antioxidant activity in red varieties. The Blauer Portugieser variety contained the highest concentrations of syringic acid 1.346 mg.L-1, caffeic acid 20 mg.L-1, ferulic acid 1.192 mg.L-1, coumaric acid 3.231 mg.L-1, trans-resveratrol 14.195 mg.L-1, catechin 79.314 mg.L-1 and epicatechin 33.205 mg.L-1. Cabernet Moravia contained the highest concentration of protocatechuic acid 1.201 mg.L-1, the Sauvignon variety reached the highest concentration of gallic acid 4.015 mg.L-1 and hydroxybenzoic acid 0.076 mg.L-1. The highest values of alpha-amino acids were determined in the Blauer Portugieser variety 165.3 mg L-1 and the lowest in the Grüner Veltliner variety 33.3 mg L-1. The highest concentration of ammonia nitrogen was 214 mg L-1 for the Blauer Portugieser variety and the lowest concentration of ammonia nitrogen was measured in Cabernet Moravia 35.7 mg L-1.

scholarly journals Hydrogenation of benzoic acid derivatives over Pt/TiO2 under mild conditions

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Miao Guo ◽  
Xiangtao Kong ◽  
Chunzhi Li ◽  
Qihua Yang
Keyword(s):  
Electron Transfer ◽  
Benzoic Acid ◽  
High Efficiency ◽  
Carboxyl Groups ◽  
Carboxyl Group ◽  
Benzoic Acids ◽  
Catalyst Poisoning ◽  
Benzoic Acid Derivatives ◽  
Mild Conditions ◽  
Transfer Direction

AbstractHydrogenation of benzoic acid (BA) to cyclohexanecarboxylic acid (CCA) has important industrial and academic significance, however, the electron deficient aromatic ring and catalyst poisoning by carboxyl groups make BA hydrogenation a challenging transformation. Herein, we report that Pt/TiO2 is very effective for BA hydrogenation with, to our knowledge, a record TOF of 4490 h−1 at 80 °C and 50 bar H2, one order higher than previously reported results. Pt/TiO2 catalysts with electron-deficient and electron-enriched Pt sites are obtained by modifying the electron transfer direction between Pt and TiO2. Electron-deficient Pt sites interact with BA more strongly than electron-rich Pt sites, helping the dissociated H of the carboxyl group to participate in BA hydrogenation, thus enhancing its activity. The wide substrate scope, including bi- and tri-benzoic acids, further demonstrates the high efficiency of Pt/TiO2 for hydrogenation of BA derivatives.

scholarly journals Spontaneous deformation of protocatechuic acid crystals

1949 ◽  
Vol 197 (1050) ◽  
pp. 283-294 ◽  
Keyword(s):  
Protocatechuic Acid ◽  
Motion Pictures ◽  
Extensive Study ◽  
The Other ◽  
Three Dimensions ◽  
Stable Configuration ◽  
Unique Case ◽  
The Past ◽  
Spontaneous Deformation ◽  
Lattice Planes

In this paper an extensive study is reported of the very remarkable, and thus far apparently unique, case of the deformation in three dimensions of protocatechuic acid, to which attention was drawn many years ago by Otto Lehmann. The deformations are spontaneous, and are probably due to progressive gliding of the lattice planes, which exist in two configurations, one stable and the other unstable, the latter being the condition of the long prismatic rods when they first form. Such a prism presently deforms into a zigzag crystal, with stable and unstable sections in alternation which, with continuation of the deformation, becomes again straight, but now in the stable configuration. The bending is progressive, like that of an umbrella case, pendant from the end of an oblique cane pointed down, when the latter is pushed into it. The movements are so rapid that motion pictures, made with a microscope, were necessary for the observation of certain stages of the deformation. The deformations have been shown to many chemists and physicists during the past decade or more, none of whom had ever seen or heard of this remarkable type of crystal movement. The deformations are usually observed as the warm saturated solution cools, but they also occur after the crystal has been dried for many hours.

scholarly journals Metabolism of the nucleic acids of rumen bacteria by preruminant and ruminant lambs

1981 ◽  
Vol 45 (3) ◽  
pp. 517-527 ◽  
Author(s):  
M. A. Razzaque ◽  
J. H. Topps ◽  
R. N. B. Kay ◽  
J. M. Brockway
Keyword(s):  
Nucleic Acids ◽  
Bacterial Culture ◽  
Total Activity ◽  
Total Radioactivity ◽  
The Other ◽  
Nucleic Acid Content ◽  
Rumen Bacteria ◽  
Total Nucleic Acid ◽  
Purine Base ◽  
Close Relationship

1. A rumen bacterial culture containing specifically labelled nucleic acids was prepared using [8-14C]adenine.2. The labelled preparation was given in a liquid diet to two preruminant lambs and via a rumen tube to two ruminant lambs. The radioactivity excreted in exhaled gases, faeces and urine and that incorporated into tissues was determined.3 The preruminant lambs absorbed 58.3% of the total radioactivity measured after 24 h and the ruminant lambs 66.6% of the total activity measured after 48 h.4. Of the total radioactivity absorbed the preruminant lambs exhaled 38%, excreted 34% in urine and retained 29% in tissues. The corresponding values for the ruminant lambs were 12,41 and 47% respectively.5. There was a close relationship between total nucleic acid content and radioactivity per g of tissues of both preruminant and ruminant lambs.6. Of the radioactivity in the urine, the ruminant and one preruminant lamb excreted most in the fraction containing allantoin, while the other lamb excreted most activity in the uric acid fraction.7. The salvaging of the breakdown products of bacterial nucleic acids to make tissue nucleic acids appears to be an important synthesis in preruminant and ruminant lambs and of the likely precursors the purine base may be more important than the nucleoside.

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