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Journal ArticleDOI

The origin of urinary aromatic compounds excreted by ruminants. 2. The metabolism of phenolic cinnamic acids to benzoic acid.

01 Jan 1982-British Journal of Nutrition (Br J Nutr)-Vol. 47, Iss: 1, pp 155-164
TL;DR: It is concluded that rumen microbial metabolism of dietary phenolic cinnamic acids to 3-phenylpropionic acid followed by its absorption and oxidation in the body tissues is responsible for the greater part of the benzoic and cinnic acids found in ruminant urine.
Abstract: 1. The extent to which phenolic derivatives of benzoic acid (seven); of phenylacetic acid (one); of 3-phenylpropionic acid (one) and of cinnamic acid (six) served as precursors of the urinary benzoic acid excreted by sheep was determined after administration as continuous drips via rumen or abomasal cannulas. 2. Phenolic derivatives of benzoic or of phenylacetic acid were not dehydroxylated to yield aromatic acids following administration via either route. 3. Rumen infusion of phenolic derivatives of both 3-phenylpropionic and cinnamic acids gave enhanced rumen concentrations of 3-phenylpropionic acid with negligible amounts of benzoic acid. Between 63 and 106% of the 2-, 3- or 4-hydroxy acids, of the 3,4-dihydroxy acids or of the 3-methoxy, 4-hydroxy acids infused were excreted in the urine as benzoic acid and a variable proportion, characteristic of the individual animal, of up to 20% of the dose as cinnamic acid. 4. Abomasal infusion of monohydroxy 3-phenylpropionic and cinnamic acids did not yield urinary benzoic acid increments. However, between 11 and 34% of abomasally-infused disubstituted phenolic cinnamic acids infused were excreted in the urine as benzoic acid due, it is postulated, to entero-hepatic circulation and microbial metabolism of the infused acids in the large intestine. 5. It is concluded that rumen microbial metabolism of dietary phenolic cinnamic acids to 3-phenylpropionic acid followed by its absorption and oxidation in the body tissues is responsible for the greater part of the benzoic and cinnamic acids found in ruminant urine.

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Citations
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Journal ArticleDOI
TL;DR: An overview of the nutritional effects of the main groups of polyphenolic compounds, including their metabolism, effects on nutrient bioavailability, and antioxidant activity, is offered, as well as a brief description of the chemistry ofpolyphenols and their occurrence in plant foods.
Abstract: Polyphenols constitute one of the most numerous and ubiquitous groups of plant metabolites and are an integral part of both human and animal diets. Ranging from simple phenolic molecules to highly polymerized compounds with molecular weights of greater than 30,000 Da, the occurrence of this complex group of substances in plant foods is extremely variable. Polyphenols traditionally have been considered antinutrients by animal nutritionists, because of the adverse effect of tannins, one type of polyphenol, on protein digestibility. However, recent interest in food phenolics has increased greatly, owing to their antioxidant capacity (free radical scavenging and metal chelating activities) and their possible beneficial implications in human health, such as in the treatment and prevention of cancer, cardiovascular disease, and other pathologies. Much of the literature refers to a single group of plant phenolics, the flavonoids. This review offers an overview of the nutritional effects of the main groups of polyphenolic compounds, including their metabolism, effects on nutrient bioavailability, and antioxidant activity, as well as a brief description of the chemistry of polyphenols and their occurrence in plant foods.

3,821 citations

Journal ArticleDOI
TL;DR: This paper reviews recent literature on the topic as well as present research from laboratories on the effect of condensed tannins on rumen microbial ecology and rumen metabolism and their impact on the nutrition of the animal.

723 citations

Journal ArticleDOI
TL;DR: A high abundance of microbial metabolites shows that the bioavailability of chlorogenic acid depends largely on its metabolism by the gut microflora, and their potential importance in explaining the biological effects of dietary polyphenols is emphasized.
Abstract: Chlorogenic acid, the ester of caffeic acid with quinic acid, is one of the most abundant polyphenols in the human diet with coffee, fruits and vegetables as its major sources. Its antioxidant and anticarcinogenic properties have been well established in animal studies. However, little is known about its gut absorption and metabolism. In the present work, four groups of rats (n = 8) were fed a diet supplemented with chlorogenic, caffeic or quinic acids (250 micromol/d) or an unsupplemented diet for 8 d. Parent compounds and their metabolites were estimated in urine (24-h collection) and plasma by HPLC-electrospray ionization-tandem mass spectrometry. Significant differences in their levels were observed among the groups. The recovery of chlorogenic acid in urine was low (0.8%, mol/mol), and the total urinary excretion of caffeic acid liberated by hydrolysis of chlorogenic acid and its tissular methylated metabolites (ferulic and isoferulic acids) did not account for >0.5% (mol/mol) of the dose ingested. On the other hand, the metabolites of microbial origin, namely, m-coumaric acid and derivatives of phenylpropionic, benzoic and hippuric acids, represented the major compounds in both urine and plasma. Hippuric acid largely originated from the transformation of the quinic acid moiety, and all other metabolites from the caffeic acid moiety. These microbial metabolites accounted for 57.4% (mol/mol) of the chlorogenic acid intake. Such a high abundance of microbial metabolites shows that the bioavailability of chlorogenic acid depends largely on its metabolism by the gut microflora. Their potential importance in explaining the biological effects of dietary polyphenols is emphasized.

462 citations

Journal ArticleDOI
TL;DR: Several approaches have been suggested and evaluated for reducing ammonia emissions from excreted animal manure: reducing nitrogen excretion through dietary manipulation, reducing volatile ammonia in the manure to stop ammonia loss, and segregating urine from faeces to reduce contact between urease and urine.

267 citations

Journal ArticleDOI
TL;DR: In this paper, the direct action of a human faecal microbiota on the metabolism of caffeic, chlorogenic and caftaric acids in an in vitro fermentation model was investigated.

197 citations

References
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Book
01 Jan 1974
TL;DR: As one of the part of book categories, human intestinal flora always becomes the most wanted book.
Abstract: If you really want to be smarter, reading can be one of the lots ways to evoke and realize. Many people who like reading will have more knowledge and experiences. Reading can be a way to gain information from economics, politics, science, fiction, literature, religion, and many others. As one of the part of book categories, human intestinal flora always becomes the most wanted book. Many people are absolutely searching for this book. It means that many love to read this kind of book.

447 citations

Book
01 Jan 1964

369 citations


"The origin of urinary aromatic comp..." refers background in this paper

  • ...When experimental periods were of more than 24 h duration (i.e. in Expts 1, 5 and 6 in which QA, CHCA, BA, 2OH-BA, 3,40H-BA, CA, 20H-CA, 30H-CA, 40H-CA, 3,40H-CA, 3Me0,40H-CA or CHL were infused; Tables 1 and 2, Martin, 1982) the U.V. absorbance of samples of the infusion solution was determined daily....

    [...]

  • ...All acids were recrystallized twice from water and the following A,, and e values (in parentheses) found: 20H-BA Na+ salt, 230 nm (6500); 3,40H-BA, 254 nm (7620); 30H-CA Na+ salt, 271 nm (16760); 20H-CA Na+ salt, 269 nm (14580); 40H-CA Na+ salt, 284nm (19200); 3,40H-CA Na+ salt, 286nm (14920); 3Me0,40H-CA Na+ salt, 286 nm (14070); CHL, 324 nm (18 340)....

    [...]

  • ...Aromatic acids in rumen jluid Rumen infusion of 2OH-CA, 30H-CA, 40H-CA, 3,40H-CA, 3Me0,40H-CA and CHL d l resulted in increased concentrations of 3-PPA in rumen fluid (Fig....

    [...]

  • ...The molecular weights of 3,40H-CA; 3Me0,40H-CA and of CHL are 356, 370 and 530 respectively; the percentages of these acids excreted in the urine as BA, 3-PPA and CA after abomasal infusion were 23, 11 and 34% respectively (see Table 2)....

    [...]

  • ...Three samples of coffee beans were used which contained between 42 and 71 g CHL/kg fresh weight....

    [...]

Journal ArticleDOI
TL;DR: In this article, five phenolic acids, ferulic, p-coumaric, syringic, vanillic, and p-hydroxybenzoic, were quantitatively estimated in corn, wheat, sorghum, and oats residues.
Abstract: Five phenolic acids, ferulic, p-coumaric, syringic, vanillic, and p-hydroxybenzoic, were quantitatively estimated in corn, wheat, sorghum, and oats residues, p-Coumaric acid was present in greater concentration than the other acids. Acid and base hydrolysis were used to free the acids from the bound form. Higher concentrations of phenolic acids were found in the alkaline hydrolysate, indicating that the acids are probably bound by an ester-type linkage. Concentrations of the cinnamic acid derivatives in the acid hydrolysate are probably low due to the breakdown of the free phenolic acids after acid hydrolysis. It appears that under ideal decomposition conditions, p-coumaric acid might be released in sufficient quantity in localized areas of the soil to affect plant growth.

275 citations

Journal ArticleDOI
TL;DR: In this article, cell walls, isolated from vegetative Italian ryegrass, pre-and post-flowering perennial ry egregrass and the faeces of sheep fed the herb, were treated with alkali and the liberated p-coumaric acid (PCA), ferulic acid (FA) and vanillin estimated.
Abstract: Cell walls, isolated from vegetative Italian ryegrass, pre- and post-flowering perennial ryegrass and the faeces of sheep fed the perennial ryegrass, were treated with alkali and the liberated p-coumaric acid (PCA), ferulic acid (FA) and vanillin estimated. A higher yield of the two acids was obtained from the Italian than from the perennial ryegrass. Oxidation of the cell-wall residues indicated the presence of the 1-phenylpropene structural unit in the lignin cores. There was a highly significant correlation between the digestibility of the cell walls from perennial ryegrass and the FA/PCA ratio. The recovery of PCA (24 to 59 %) from the faecal cell walls was much higher than that of FA (5 to 21 %). For each acid this recovery was lower in the pre-flowering herbage.

219 citations