scholarly journals Excretion of benzoic acid derivatives in urine of sheep given intraruminal infusions of 3-phenylpropionic and cyclohexanecarboxylic acids

1997 ◽  
Vol 77 (4) ◽  
pp. 577-592 ◽  
Author(s):  
J. H. Pagella ◽  
X. B. Chen ◽  
N. A. Macleod ◽  
E. R. Ørskov ◽  
P. J. S. Dewey
Keyword(s):  
Benzoic Acid ◽  
Urinary Excretion ◽  
Hippuric Acid ◽  
Quantitative Relationship ◽  
The Other ◽  
Urinary Recovery ◽  
Faecal Excretion ◽  
Benzoic Acid Derivatives ◽  
Significant Linear Correlation ◽  
Glycine Conjugate

The quantitative relationship between the urinary excretion of benzoic acid (BA)and the uptake of 3-phenylpropionic (PPA) and cyclohexanecarboxylic (CHCA) acids was assessed.PPA and CHCA are produced in the rumen by microbial fermentation of lignocellulosic feeds and metabolized, after absorption, to BA which is excreted in the urine mainly as its glycine conjugate hippuric acid (HA). Four sheep nourished by intragastric infusions of all nutrients weregiven continuous ruminal infusions of PPA (8,16 or 24 mmol/d) either alone or with CHCA (8 or 16 mmol/d) in a factorial experiment. The treatments were allocated to ten consecutive 6 d periods, with a control being repeated at periods 1, 5 and 10. PPA and CHCA ruminal absorption rates, estimated using the liquid-phase marker Cr-EDTA, were 0·78 (SD 0·29)/h and 0·88 (SD 0·28)/h respectively. For the control, HA excretion was only 0·22 (SD 0·33) mmol/d and free BA was absent. For the other treatments, both HA and free BA were present and HA accounted for 0·85 (SD 0·05) of total BA. The urinary excretion of total BA showed a significant linear correlation (r = 0·997, P<0·001) with the amounts of PPA and CHCA infused. The urinary recovery of infused PPA and CHCA as total BA was 0·79 (SE 0·01). Faecal excretion of BA and its precursors was negligible. Results of this study show that urinary total BA is a potential estimator of the absorption of PPA + CHCA produced in the rumen

Urinary excretion of benzoic acid and hippuric acid in sheep given ruminal infusion of 3-phenylpropionic and cyclohexanecarboxylic acids

1996 ◽  
Vol 1996 ◽  
pp. 179-179
Author(s):  
J.H. Pagella ◽  
X.B. Chen ◽  
N.A. MacLeod ◽  
E.R. Ãrskov
Keyword(s):  
Benzoic Acid ◽  
Urinary Excretion ◽  
Hippuric Acid ◽  
Quantitative Relationship ◽  
Microbial Metabolism ◽  
Microbial Fermentation ◽  
Cinnamic Acids ◽  
Glycine Conjugate ◽  
Microbial Action

Microbial fermentation of lignoceluUosic feeds in the rumen produces 3-phenylpropionic (PPA) and cyclohexanecarboxylic (CHCA) acids. Feed phenolic cinnamic acids are regarded as the main precursors of PPA upon microbial action (Martin 1982b). CHCA can be produced by microbial metabolism of dietary alicyclic compounds such as quinic and shikimic acids (Balba and Evans, 1977; Martin, 1982a). Following absorption CHCA and PPA are subjected to metabolism mainly in the liver yielding benzoic acid (BA) which is extensively excreted in urine mainly as its glycine conjugate hippuric acid (HA). The aim of this work was to assess the quantitative relationship between the urinary excretion of total BA (free BA + HA) and the uptake of PPA and CHCA.

Urinary excretion of benzoic acid and hippuric acid in sheep given ruminal infusion of 3-phenylpropionic and cyclohexanecarboxylic acids

1996 ◽  
Vol 1996 ◽  
pp. 179-179
Author(s):  
J.H. Pagella ◽  
X.B. Chen ◽  
N.A. MacLeod ◽  
E.R. Ãrskov
Keyword(s):  
Benzoic Acid ◽  
Urinary Excretion ◽  
Hippuric Acid ◽  
Quantitative Relationship ◽  
Microbial Metabolism ◽  
Microbial Fermentation ◽  
Cinnamic Acids ◽  
Glycine Conjugate ◽  
Microbial Action

Microbial fermentation of lignoceluUosic feeds in the rumen produces 3-phenylpropionic (PPA) and cyclohexanecarboxylic (CHCA) acids. Feed phenolic cinnamic acids are regarded as the main precursors of PPA upon microbial action (Martin 1982b). CHCA can be produced by microbial metabolism of dietary alicyclic compounds such as quinic and shikimic acids (Balba and Evans, 1977; Martin, 1982a). Following absorption CHCA and PPA are subjected to metabolism mainly in the liver yielding benzoic acid (BA) which is extensively excreted in urine mainly as its glycine conjugate hippuric acid (HA). The aim of this work was to assess the quantitative relationship between the urinary excretion of total BA (free BA + HA) and the uptake of PPA and CHCA.

scholarly journals The fate of benzoic acid in various species

1970 ◽  
Vol 118 (1) ◽  
pp. 47-51 ◽  
Author(s):  
J. W. Bridges ◽  
M. R. French ◽  
R. L. Smith ◽  
R. T. Williams
Keyword(s):  
Guinea Pig ◽  
Rhesus Monkey ◽  
Benzoic Acid ◽  
Urinary Excretion ◽  
Squirrel Monkey ◽  
Golden Hamster ◽  
Hippuric Acid ◽  
The Other ◽  
Main Metabolite ◽  
Fruit Bat

1. The urinary excretion of orally administered [14C]benzoic acid in man and 20 other species of animal was examined. 2. At a dose of 50mg/kg, benzoic acid was excreted by the rodents (rat, mouse, guinea pig, golden hamster, steppe lemming and gerbil), the rabbit, the cat and the capuchin monkey almost entirely as hippuric acid (95–100% of 24h excretion). 3. In man at a dose of 1mg/kg and the rhesus monkey at 20mg/kg benzoic acid was excreted entirely as hippuric acid. 4. At 50mg/kg benzoic acid was excreted as hippuric acid to the extent of about 80% of the 24h excretion in the squirrel monkey, pig, dog, ferret, hedgehog and pigeon, the other 20% being found as benzoyl glucuronide and benzoic acid, the latter possibly arising by decomposition of the former. 5. On increasing the dose of benzoic acid to 200mg/kg in the ferret, the proportion of benzoyl glucuronide excreted increased and that of hippuric acid decreased. This did not occur in the rabbit, which excreted 200mg/kg almost entirely as hippuric acid. It appears that the hedgehog and ferret are like the dog in respect to their metabolism of benzoic acid. 6. The Indian fruit bat produced only traces of hippuric acid and possibly has a defect in the glycine conjugation of benzoic acid. The main metabolite in this animal (dose 50mg/kg) was benzoyl glucuronide. 7. The chicken, side-necked turtle and gecko converted benzoic acid mainly into ornithuric acid, but all three species also excreted smaller amounts of hippuric acid.

scholarly journals New Gallotannin and other Phytochemicals from Sycamore Maple (Acer pseudoplatanus) Leaves

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Lu Zhang ◽  
Zong-Cai Tu ◽  
Tao Yuan ◽  
Hang Ma ◽  
Daniel B. Niesen ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Antioxidant Activities ◽  
The Other ◽  
Acer Pseudoplatanus ◽  
Mass Spectral ◽  
Benzoic Acid Derivatives ◽  
Glucosidase Inhibitors ◽  
Maple Leaves ◽  
Sycamore Maple ◽  
Clinical Drug

The maple (Acer) genus is a reported source of bioactive (poly)phenols, including gallotannins, but several of its members, such as the sycamore maple (A. pseudoplatanus). remain uninvestigated. Herein, thirty-nine compounds, including a new gallotannin, 1,2,3-tri- O-galloyl-6- O-( p-hydroxybenzoyl)-β-D-glucopyranoside (1), and thirty-eight (2-39) known compounds, consisting of four gallotannins, one ellagitannin, thirteen flavonoids, eight hydroxycinnamic acids, ten benzoic acid derivatives, and two sesquiterpenoids, were isolated from sycamore maple leaves. Their structures were determined based on NMR and mass spectral analyses. The isolates were evaluated for α-glucosidase inhibitory and antioxidant activities. Among the isolates, the gallotannins were the most potent α-glucosidase inhibitors with thirteen-fold more potent activity compared with the clinical drug, acarbose (IC50 = 16–31 vs. 218 μM). Similarly, the gallotannins showed the highest antioxidant activities, followed by the other phenolic sub-classes, while the sesquiterpenoids were inactive.

scholarly journals Reduced Formation of Hippuric Acid After Oral Benzoic Acid in Friedreich’s Ataxia

1982 ◽  
Vol 9 (2) ◽  
pp. 217-220
Author(s):  
A. Barbeau ◽  
R. Bouchard ◽  
T. Cloutier ◽  
J.P. Bouchard
Keyword(s):  
Benzoic Acid ◽  
Bile Acids ◽  
Normal Control ◽  
Hippuric Acid ◽  
Friedreich’S Ataxia ◽  
Friedreich's Ataxia ◽  
The Other ◽  
Acid Load ◽  
Relationship Of ◽  
The Relationship

SUMMARY:We have observed a markedly decreased formation of hippuric acid after benzoic acid load in patients with typical Friedreich’s Ataxia compared to normal control subjects. Since there is evidence for normal or even enhanced tauro-conjugation in the bile of patients with this disease, with a decreased G/T ratio, it is unlikely that co-factor or enzyme concentrations are the cause of this defect. We postulate decreased availability of the enzyme for glycine conjugation either to bile acids in the usual situation or to benzoic acid in the artefactual test condition. This could be due to the enzyme’s preference for an increased amount of taurine substrate in the liver. The relationship of this observation to the other biochemical changes observed in Friedreich’s Ataxia must still be established.

scholarly journals Conjugation of benzoic acid in marsupials

1985 ◽  
Vol 33 (5) ◽  
pp. 693 ◽  
Author(s):  
Almah Bt. Awaluddin ◽  
Stuart McLean
Keyword(s):  
Benzoic Acid ◽  
Metabolic Pathway ◽  
Hippuric Acid ◽  
Urinary Metabolites ◽  
Carbon Fragment ◽  
Marsupial Species ◽  
Glycine Conjugate

The urinary metabolites of benzoic acid have been studied in seven marsupial species and the rat. Benzoic acid was excreted mainly as the glycine conjugate, hippuric acid, with smaller, though variable, amounts as benzoyl glucuronide. Thus the overall pattern of metabolism was similar to that found in most other mammals. All species formed significant amounts of a recently discovered metabolite of benzoic acid, 0-hydroxyphenylpropionic acid, suggesting that the metabolic pathway for its formation, involving the addition of a two-carbon fragment, may occur generally in other species.

scholarly journals The urinary excretion of aromatic acids by starved sheep

1969 ◽  
Vol 23 (3) ◽  
pp. 715-725 ◽  
Author(s):  
A. A. Martin
Keyword(s):  
Benzoic Acid ◽  
Urinary Excretion ◽  
Diethyl Ether ◽  
Hippuric Acid ◽  
Phenylacetic Acid ◽  
Acid Output ◽  
Light Petroleum ◽  
Aromatic Acids ◽  
Exogenous Origin ◽  
Almost All

1. Four wether sheep were maintained on a diet of hay for 2 weeks and then starved for a period of 4 days.2. Immediately before and during starvation the urinary excretion in the following fractions was determined: hippuric acid, creatinine, total diethyl ether-soluble acids of hydrolysed and unhydrolysed urine, total aromatic acids in hydrolysed and unhydrolysed urine and the proportion of the former present as benzoic and phenylacetic acids.3. A method for determining the benzoic acid content of light petroleum extracts of urine has been developed and is described.4. Starvation had little effect on the urinary excretion of phenylacetic acid or creatinine, but during the first 2 days of starvation there were large decreases in the excretion of all the other urinary fractions studied.5. Of the fractions examined, 43% of the diethyl ether-soluble acids of hydrolysed urine and 42% of those of unhydrolysed urine were of exogenous origin; 76% of the total urinary aromatic acids were of exogenous origin. Partition of the aromatic acids in the urine of two of the four sheep indicated that the reduction in aromatic acid excretion on starvation was completely accounted for by the decline in benzoic acid output. Almost all the hippuric acid (97%) was of exogenous origin.6. These results have been compared with the urinary output of aromatic acids by nonruminants when fasted, and possible reasons for the relatively large amounts of phenylacetic acid found in the urine of starved sheep have been discussed.

Bjerkandera adusta as a source of benzoic acid derivatives targeting 26S proteasome and cathepsins B&L

2019 ◽  
Author(s):  
K Georgousaki ◽  
N Tsafantakis ◽  
S Gumeni ◽  
V González-Menéndez ◽  
G Lambrinidis ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
26S Proteasome ◽  
Bjerkandera Adusta ◽  
Benzoic Acid Derivatives

2,4-Dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic Acid Derivatives: In Vitro Antidiabetic Activity, Molecular Modeling and In silico ADMET Screening

2019 ◽  
Vol 15 (2) ◽  
pp. 186-195 ◽  
Author(s):  
Samridhi Thakral ◽  
Vikramjeet Singh
Keyword(s):  
Molecular Docking ◽  
Benzoic Acid ◽  
Inhibitory Activity ◽  
In Silico ◽  
Computational Study ◽  
Antidiabetic Activity ◽  
Standard Drug ◽  
Benzoic Acid Derivatives ◽  
In Silico Admet ◽  
Inhibitory Potential

Background: Postprandial hyperglycemia can be reduced by inhibiting major carbohydrate hydrolyzing enzymes, such as α-glucosidase and α-amylase which is an effective approach in both preventing and treating diabetes. Objective: The aim of this study was to synthesize a series of 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl] benzoic acid derivatives and evaluate α-glucosidase and α-amylase inhibitory activity along with molecular docking and in silico ADMET property analysis. Method: Chlorosulfonation of 2,4-dichloro benzoic acid followed by reaction with corresponding anilines/amines yielded 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives. For evaluating their antidiabetic potential α-glucosidase and α-amylase inhibitory assays were carried out. In silico molecular docking studies of these compounds were performed with respect to these enzymes and a computational study was also carried out to predict the drug-likeness and ADMET properties of the title compounds. Results: Compound 3c (2,4-dichloro-5-[(2-nitrophenyl)sulfamoyl]benzoic acid) was found to be highly active having 3 fold inhibitory potential against α-amylase and 5 times inhibitory activity against α-glucosidase in comparison to standard drug acarbose. Conclusion: Most of the synthesized compounds were highly potent or equipotent to standard drug acarbose for inhibitory potential against α-glucosidase and α-amylase enzyme and hence this may indicate their antidiabetic activity. The docking study revealed that these compounds interact with active site of enzyme through hydrogen bonding and different pi interactions.

Application of an LC-MS/MS Method to a Urinary Excretion Study of Triflusal and its Main Metabolite 2-hydroxy-4-trifluoromethyl Benzoic Acid in Human Urine

2020 ◽  
Vol 16 (3) ◽  
pp. 328-334
Author(s):  
Jie Ge ◽  
Jin-Wen Wang ◽  
Qi-Yan Guo ◽  
Ai-Dong Wen
Keyword(s):  
Benzoic Acid ◽  
Urinary Excretion ◽  
Human Urine ◽  
Multiple Reaction Monitoring ◽  
Main Metabolite ◽  
Linear Relationships ◽  
Pharmacokinetic Properties ◽  
Liquid Chromatography Tandem Mass ◽  
Excretion Study ◽  
Acetate Aqueous Solution

Objective: A validated liquid chromatography-tandem mass spectrometry method (LCMS/ MS) was established to simultaneously determine the concentration of triflusal and its main metabolite 2-hydroxy-4-trifluoromethyl benzoic acid(HTB) in human urine. Methods: The separation was performed on a Dikma C18 column using isocratic elution with acetonitrile-4 mmol/L ammonium acetate aqueous solution containing 0.3 % formic acid water (78: 28, V/V). The method involved extraction with methanol using protein precipitation. The precursor-toproduct ion transitions with multiple reaction monitoring was m/z 247.1→161.1, 204.8→106.7and 136.9→93.0 for triflusal, HTB and salicylic acid(IS), respectively. The method showed good linear relationships over the ranges of 0.08 to 48 μg/mL and0.5 to 50 μg/mL. Results: It was the first time that a urinary excretion study of triflusal capsule as oral. The cumulative urinary recovery showed 8.5% and 2.7% for triflusal and HTB, respectively. Conclusion: This method was successfully used for evaluating the pharmacokinetic properties of triflusal and HTB in urine in Chinese healthy subjects.

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