http://www.dietcan.net/docs/Polifenoles%20en%20alimentos%20y%20biodisponibilidad.pdf

Polyphenols: food sources and bioavailability

The metabolic syndrome

Flavonoids are nearly ubiquitous in plants and are recognized as the pigments responsible for the colors of leaves, especially in autumn. They are rich in seeds, citrus fruits, olive oil, tea, and red wine. They are low molecular weight compounds composed of a three-ring structure with various substitutions. This basic structure is shared by tocopherols (vitamin E). Flavonoids can be subdivided according to the presence of an oxy group at position 4, a double bond between carbon atoms 2 and 3, or a hydroxyl group in position 3 of the C (middle) ring. These characteristics appear to also be required for best activity, especially antioxidant and antiproliferative, in the systems studied. The particular hydroxylation pattern of the B ring of the flavonoles increases their activities, especially in inhibition of mast cell secretion. Certain plants and spices containing flavonoids have been used for thousands of years in traditional Eastern medicine. In spite of the voluminous literature available, however, Western medicine has not yet used flavonoids therapeutically, even though their safety record is exceptional. Suggestions are made where such possibilities may be worth pursuing.

The Effects of Plant Flavonoids on Mammalian Cells:Implications for Inflammation, Heart Disease, and Cancer

Flavonoids are a class of secondary plant phenolics with significant antioxidant and chelating properties. In the human diet, they are most concentrated in fruits, vegetables, wines, teas and cocoa. Their cardioprotective effects stem from the ability to inhibit lipid peroxidation, chelate redox-active metals, and attenuate other processes involving reactive oxygen species. Flavonoids occur in foods primarily as glycosides and polymers that are degraded to variable extents in the digestive tract. Although metabolism of these compounds remains elusive, enteric absorption occurs sufficiently to reduce plasma indices of oxidant status. The propensity of a flavonoid to inhibit free-radical mediated events is governed by its chemical structure. Since these compounds are based on the flavan nucleus, the number, positions, and types of substitutions influence radical scavenging and chelating activity. The diversity and multiple mechanisms of flavonoid action, together with the numerous methods of initiation, detection and measurement of oxidative processes in vitro and in vivo offer plausible explanations for existing discrepancies in structure-activity relationships. Despite some inconsistent lines of evidence, several structure-activity relationships are well established in vitro. Multiple hydroxyl groups confer upon the molecule substantial antioxidant, chelating and prooxidant activity. Methoxy groups introduce unfavorable steric effects and increase lipophilicity and membrane partitioning. A double bond and carbonyl function in the heterocycle or polymerization of the nuclear structure increases activity by affording a more stable flavonoid radical through conjugation and electron delocalization. Further investigation of the metabolism of these phytochemicals is justified to extend structure-activity relationships (SAR) to preventive and therapeutic nutritional strategies.

Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships.

Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies

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.

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Chlorogenic Acid Bioavailability Largely Depends on Its Metabolism by the Gut Microflora in Rats

Anthocyanins are present in human diet due to their wide occurrence in fruits and beverages. They possess antioxidant activities and could be involved in several health effects. The aim of this study was to investigate anthocyanin metabolism and distribution in the digestive area organs (stomach, jejunum and liver) and kidney, as well as a target tissue (brain) in rats fed with a blackberry (Rubus fruticosus L.) anthocyanin-enriched diet for 15 days. Identification and quantification of anthocyanin metabolites was carried out by HPLC-ESI-MS-MS and HPLC-DAD, respectively. The stomach exhibited only native blackberry anthocyanins (cyanidin 3-O-glucoside and cyanidin 3-O-pentose), while in other organs (jejunum, liver, and kidney) native and methylated anthocyanins as well as conjugated anthocyanidins (cyanidin and peonidin monoglucuronides) were identified. Proportions of anthocyanin derivatives differed according to the organ considered, with the liver presenting the highest proportion of methylated forms. Jejunum and plasma also contained aglycone forms. In the brain, total anthocyanin content (blackberry anthocyanins and peonidin 3-O-glucoside) reached 0.25 +/- 0.05 nmol/g of tissue (n = 6). The urinary excretion of total anthocyanins was low (0.19 +/- 0.02% of the ingested amount). Thus, organs of the digestive area indicated a metabolic pathway of anthocyanins with enzymatic conversions (methylation and/or glucurono-conjugation). Moreover, following consumption of an anthocyanin-rich diet, anthocyanins enter the brain.

Anthocyanin Metabolism in Rats and Their Distribution to Digestive Area, Kidney, and Brain

Quercetin is one of the most widely distributed flavonoids present in fruits and vegetables. The present experiments were performed on rats adapted for 3 wk to a semipurified diet supplemented with...

Plasma metabolites of quercetin and their antioxidant properties

In the present study the actual role of propionic acid in the control of fatty acid and cholesterol synthesis was investigated in isolated liver cells from fed rats maintained in the presence of near-physiological concentrations of glucose, glutamine and acetate. Using 3H2O for lipid labelling, propionate appears as an effective inhibitor of fatty acid synthesis and to a lesser extent of cholesterol synthesis, even at the lowest concentration used (0.6 mmol/l). Butyrate is a potent activator of both synthetic pathways, and the activating effect was not counteracted by propionate. Using 1-[14C]acetate, it was observed that propionate at a moderate concentration, or 1 mmol oleate/l, are both very effective inhibitors of 14C incorporation into fatty acid and cholesterol. This incorporation was drastically inhibited when propionate and oleate were present together in the incubation medium. The net utilization of acetate by rat hepatocytes was impaired by propionate, in contrast to oleate. 1-[14C]butyrate was utilized at a high rate for fatty acid synthesis, but to a lesser extent for cholesterol synthesis; both processes were unaffected by propionate. Intracellular citrate concentration was not markedly depressed by propionate, whereas it was strongly elevated by butyrate. In conclusion, propionate may represent an effective inhibitor of lipid synthesis when acetate is a major source of acetyl-CoA, a situation which is encountered with diets rich in readily-fermentable fibres. The present findings also suggest that propionate may be effective at concentrations close to values measured in vivo in the portal vein.

https://www.cambridge.org/core/services/aop-cambridge-core/content/view/40CD9F1A6C068EAA1041041BD3F987E0/S0007114595001255a.pdf/div-class-title-effect-of-propionate-on-fatty-acid-and-cholesterol-synthesis-and-on-acetate-metabolism-in-isolated-rat-hepatocytes-div.pdf

Effect of propionate on fatty acid and cholesterol synthesis and on acetate metabolism in isolated rat hepatocytes

After consumption, anthocyanins are rapidly absorbed as glycosides. Their rapid appearance in plasma could result from absorption through the gastric wall. The aim of this study was to evaluate the fate of anthocyanins in the stomach. Absorption of purified anthocyanins (14 micromol/L) as well as blackberry 14 and 750 micromol/L) and bilberry (88 micromol/L) anthocyanins was compared after in situ gastric administration for 30 min. A high proportion (approximately 25%) of anthocyanin monoglycosides (glucoside or galactoside) was absorbed from the stomach, whereas absorption of cyanidin 3-rutinoside was lower. Bilberry anthocyanins were also efficiently absorbed, but absorption varied greatly (19-37%) according to the anthocyanin structure; delphinidin glycosides were the most absorbed. When a high concentration of blackberry anthocyanins (750 micromol/L) was injected into the gastric lumen, the percentage of cyanidin 3-glucoside (Cy 3-glc) absorption was lower than after administration of a low concentration (14 micromol/L). After administration of this high concentration, blackberry anthocyanins were observed in plasma from gastric vein and aorta, whereas neither aglycones nor metabolites were detected. Analysis of bile samples revealed that Cy 3-glc appeared in bile after as little as 20 min. Peonidin 3-glucoside (the methylated form of Cy 3-glc) as well as unknown anthocyanin metabolites were also observed in bile. Thus, this study demonstrated that anthocyanin glycosides were quickly and efficiently absorbed from the stomach and rapidly excreted into bile as intact and metabolized forms.

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Catherine Besson

Papers

Chlorogenic Acid Bioavailability Largely Depends on Its Metabolism by the Gut Microflora in Rats

Anthocyanin Metabolism in Rats and Their Distribution to Digestive Area, Kidney, and Brain

Plasma metabolites of quercetin and their antioxidant properties

Effect of propionate on fatty acid and cholesterol synthesis and on acetate metabolism in isolated rat hepatocytes

Anthocyanins Are Efficiently Absorbed from the Stomach in Anesthetized Rats