The Aerial Parts of Agrimonia procera Wallr. and Agrimonia eupatoria L. as a Source of Polyphenols, and Especially Agrimoniin and Flavonoids.

Plants of the genus Agrimonia L. perfectly fit the current trends in nutrition and food technology, namely, the need for raw materials with a high content of bioactive natural compounds, including polyphenols, which could be added to food. The composition of polyphenolics, including agrimoniin and flavonoids, in the aerial parts of Agrimonia procera Wallr. (A. procera) and Agrimonia eupatoria L. (A. eupatoria) (Rosaceae) was determined using HPLC-DAD-MS. The polyphenolic content of A. procera was found to be 3.9%, 3.2%, 2.9%, 1.8% and 1.1%, and that of A. eupatoria was determined to be 1.3%, 0.3%, 0.9%, 0.6% and 0.5% in the dry matter of leaves, stems, fruits, seeds and hypanthia, respectively. Except for A. procera hypanthia, agrimoniin was the main polyphenolic compound in the aerial parts of the studied Agrimonia species. Both plants are also a valuable source of flavonoid glycosides, especially apigenin, luteolin and quercetin. The obtained data indicate that both A. procera and A. eupatoria are potentially good sources of polyphenols (albeit significantly different in terms of their qualitative and quantitative composition), and may not only be a medicinal raw material, but also a valuable material for food use such as nutraceuticals or functional food ingredients.

Strawberry phenolic extracts effectively mitigated metabolic disturbances associated with high-fat ingestion in rats depending on the ellagitannin polymerization degree.

In the present experiment it was hypothesised that dietary strawberry ellagitannin-rich extracts would mitigate negative consequences associated with consumption. Therefore, two extracts rich in dimeric (D-ET) or monomeric (M-ET) ellagitannins (ETs) were added to a standard or high-fat diet fed to rats for four weeks. The D-ET-rich extract contained 82.3% polyphenols, and the M-ET/D-ET ratio was 40 : 60, while the M-ET-rich extract contained 88.0% and 96 : 4, respectively. The experimental feeding with high-fat diets containing extracts resulted in beneficial mitigating effects in the lipid profile, redox status of the rat's liver and blood plasma. According to the accepted hypothesis, the obtained results pointed at increased desired hepatic and plasma modifications when the extract was rich in M-ET, as indicated by favourable changes in the hepatic fat content, GSH and GSSG concentrations and GSH/GSSG ratio as well as blood plasma FRAP, ACL, HDL-cholesterol, and atherogenic coefficient values. These changes were partly connected to the fact that M-ET was more prone vs. D-ET to intestinal microbial conversion into respective metabolites. The urinary daily excretion of ET metabolites and their blood plasma concentrations were higher in rats fed with M-ET vs. D-ET-rich diets. To conclude, the metabolic action of the M-ET-rich extract in the normalization of high-fat-induced disturbances was more pronounced.

Protective Effects of a Strawberry Ellagitannin-Rich Extract against Pro-Oxidative and Pro-Inflammatory Dysfunctions Induced by a High-Fat Diet in a Rat Model.

Due to the demonstrated intestinal microbial transformation of strawberry ellagitannins (ET) into bioactive metabolites, in the current study on rats, we hypothesised that the dietary addition of a strawberry ET-rich extract (S-ET) to a high-fat diet (HFD) would attenuate disturbances in the redox and lipid status as well as in the inflammatory response. We randomly distributed 48 Wistar rats into six groups and used two-way analysis of variance (ANOVA) to assess the effects of two main factors-diet type (standard and high-fat) and ET dosage (without, low, and 3× higher)-applied to rats for 4 weeks. In relation to the hypothesis, irrespective of the dosage, the dietary application of ET resulted in the desired attenuating effects in rats fed a HFD as manifested by decreased body weight gain, relative mass of the epididymal pad, hepatic fat, oxidized glutathione (GSSG), triglycerides (TG), total cholesterol (TC), and thiobarbituric acid-reactive substances (TBARS) concentrations as well as desired modifications in the blood plasma parameters. These beneficial changes were enhanced by the high dietary addition of ET, which was associated with considerably higher concentrations of ET metabolites in the urine and plasma of rats. The results indicated that S-ET could be effectively used for the prevention and treatment of metabolic disturbances associated with obesity, dyslipidaemia, redox status imbalance, and inflammation.

Transformation of Oligomeric Ellagitannins, Typical for Rubus and Fragaria Genus, during Strong Acid Hydrolysis.

The strong acid hydrolysis analysis of galloyl-O-digalloyl-type ellagitannins (ETs), lambertianin C (LC) and sanguiin H-6, and dehydrodigalloyl-type ET, agrimoniin (AM), was performed. A quantitative and qualitative analysis of the degradation products of individual ETs was conducted using high-performance liquid chromatography-diode array detecto-electrospray ionization interface-mass spectrometry (HPLC-DAD-ESI-MS). The data indicate that ETs undergo multidirectional changes in a strongly acidic environment, where the process of successive hydrolysis of ester bonds to form ellagic acid (EA) is the dominant phenomenon in the initial phase of the reaction, followed by the depolymerization process and the formation of low-molecular ETs. Characteristic products of ET hydrolysis were distinguished: for LC: dimeric ET plus one galloyl moiety without one EA moiety (M = 1736 Da), for all analyzed ETs: sanguisorbic acid dilactone (M = 470 Da), and for AM: dehydrodigallic acid (M = 338 Da). The research carried out has allowed to create a database of possible products and routes of transformation of individual ETs, which should facilitate future research on the transformation of ETs, including potential prohealth properties of its breakdown products, under conditions occurring during food processing or digestion.

Protocatechuic acid and quercetin glucosides in onions attenuate changes induced by high fat diet in rats.

Yellow onion waste from industrial peeling was used to obtain three pure preparations: protocatechuic acid (PA), quercetin diglycosides (QD) and quercetin monoglycosides (QM). PA contained 61% protocatechuic acid, QD contained 35% quercetin diglucosides, mainly quercetin-3,4'-diglucoside, and QM contained 41% monoglucosides, mainly quercetin-4'-glucoside. The highest antioxidant activity was shown by PA. The effects of preparations on the digestive functions of the gastrointestinal tract of rats as well as the biochemical parameters and antioxidant capacity of the blood in model research on Wistar rats sustained by a high-fat diet were assessed (5 groups per 8 animals). The results of the present experiment showed that different onion phenolic preparations differently modulated the enzymatic activity of faecal (P < 0.001) and caecal (P < 0.001) microbiota. For instance, the QD preparation but not QM efficiently reduced the faecal and caecal bacterial ß-glucuronidase activity. Both protocatechuic acid and quercetin monoglycosides showed a beneficial effect by regulating blood lipids (reduction of TC (P < 0.001) and TG (P < 0.001), non-HDL increase in HDL (P < 0.001)), thereby lowering the risk factors for atherosclerotic lesions AI (P = 0.038) and AII (P = 0.013). In addition, onion phenols showed a strong antioxidant effect, however, with a different mechanism: protocatechuic acid via serum ACL (P = 0.033) increase and hepatic GSSG (P = 0.070) decrease, QM via ACW (P < 0.001) increase and hepatic TBARS (P = 0.002) decrease, and QD via serum ACW increase and hepatic GSSG decrease. It can be concluded that onion polyphenols with a lower molar weight, i.e. QM more preferably affect the blood lipid profile than QD. However QD more efficiently reduced the faecal and caecal bacterial ß-glucuronidase activity.

Structural elucidation of the ellagitannin with a molecular weight of 2038 isolated from strawberry fruit (Fragaria ananassa Duch.) and named fragariin A.

The structure of the ellagitannin (ET) with a molecular weight (MW) of 2038 isolated from strawberry fruit was elucidated on the basis of mass spectrometry data and nuclear magnetic resonance studies, with the newly determined compound being named fragariin A. Similarly to the main strawberry ET, agrimoniin (MW 1870), fragariin A was shown to contain a bis-HHDP-glucose moiety (MW 784). It exhibited the same three fragmentation ions with m/z 1567, 1265 and 633, arising from the detachment of consecutive hexahydroxydiphenoyl (HHDP) units from the structure with MW 1870. Based on spectroscopic studies, it was found that, in the tested ET (MW 2038), a free gallic acid is connected by a DOG-type bond to the 4,6-HHDP unit of the second glucose moiety of agrimoniin.

Apple pomace improves gut health in Fisher rats independent of seed content.

The mechanism behind the cholesterol lowering effects of apple pomace, a polyphenol- and fibre rich by-product in apple juice production, was investigated. Groups of male F344 rats were fed a control feed or the same feed with 2.1% or 6.5% dry apple pomace with or without seeds for 4 weeks. Effects on plasma cholesterol concentrations, excretion of bile acids, expression of genes involved in cholesterol- and bile acid synthesis, and other markers related to gut health were investigated. We found that pomace feeding decreased total-, LDL- and IDL-cholesterol concentrations compared to control. Higher production of SCFA, indicating elevated caecal fermentation, and increased excretion of total- and primary bile acids could explain the observed hypocholesterolemic effects of apple pomace, however, expression of selected genes involved in cholesterol and bile acid biosynthesis (Hmgcr and Cyp7a1) were not affected. We found no hepatotoxic or other effects of apple seeds. Altogether, our results indicate that apple pomace has beneficial effects on gut health, and that the cholesterol-lowering effect is linked to increased production of SCFA and excretion of bile acids. These effects are most likely linked to the fibre and other fruit constituents present in the pomace. Presence of apple seeds seems to impart no toxicity even at 6.5% pomace in the feed and seeds also had no influence on the biological effect of the pomace. In the future, apple pomace could potentially be used as a bioactive and possibly health promoting food ingredient.

Protective Effects of Ellagitannin-Rich Strawberry Extracts on Biochemical and Metabolic Disturbances in Rats Fed a Diet High in Fructose.

The present study compares the effects of two dietary strawberry extracts rich in monomeric (ME) or dimeric (DE) ellagitannins (ETs) on gastrointestinal, blood and tissue biomarkers in Wistar rats fed high-fructose diets. Both strawberry extracts beneficially affect the antioxidant status and lipid profile of the liver and serum. The ME extract shows a greater ability to inhibit lipid peroxidation in kidneys, more effectively decreases serum and liver triglycerides, and exerts greater anti-inflammatory effects in blood serum than the DE extract. The DE extract significantly reduces the activity of microbial enzymes in the cecum. These effects might be associated with higher cecum and urine levels of ET metabolites in rats fed with ME than in rats fed with DE. In conclusion, the diet-induced fructose-related disturbances observed in biochemical parameters are regulated by both extracts; nevertheless, the beneficial effects of the ME extract are mostly associated with systemic parameters, while those of the DE extracts are associated with local microbial activity.

Onion quercetin monoglycosides alter microbial activity and increase antioxidant capacity.

The effects on fermentation processes in the digestive tract, the biochemical parameters and antioxidant capacity of blood in rats fed high-fat diets with quercetin (Q) and quercetin with quercetin monoglycosides (Q+MQ) preparations obtained from onion waste were evaluated. Four groups of eight animals were fed for 4 weeks with a control diet (C), a high-fat diet (HF) and high-fat diets with 0.15% addition of Q and Q+MQ preparations. HF caused an increase in alanine transaminase (ALT), non-high-density lipoprotein (non-HDL) and the atherogenic index AII vs. C and a decrease in the proportion of HDL in total cholesterol (TC). Q and Q+MQ showed a tendency to moderate the values aspartate transaminase (P=.087), ALT (P<.05), TC (P=.068), non-HDL cholesterol (P<.05), triglycerides (P=.064) and the atherogenic index AII (P<.05). Q+MQ significantly increased the activity of α-glucosidase (P<.05 vs. HF), ß-glucosidase (P<.05) and ß-galactosidase (P<.05 vs. C and Q). Q increased activity of ß-glucosidase (P<.001 vs. C and HF). Both increased the activity of ß-glucuronidase (P<.05 vs. C and HF). Both increased the antioxidant capacity of the hydrophilic fraction in serum (P<.05 vs. C and HF), and Q enhanced that of the lipid fraction (P<.001). Q preparation contained 70% quercetin, and Q+MQ preparation contained 29% quercetin and 13% quercetin monoglycosides, mainly quercetin-4'-glucoside. Both exhibited high antioxidant capacity. Supplementation with Q and Q+MQ increased the enzymatic activity of the intestinal microbiota and the antioxidant capacity of blood and revealed a tendency to improve the blood lipid profile. MQ were particularly effective in stimulating the bacterial enzymatic activity.

Ellagitannins from Strawberries with Different Degrees of Polymerization Showed Different Metabolism through Gastrointestinal Tract of Rats.

The present paper describes a comparative study of the metabolism of (1) ellagic acid, (2) monomeric ellagitannins (a mixture of α- and ß-bis-hexahydroxydiphenoyl-d-glucose), and (3) dimeric ellagitannins (mainly agrimoniin with both glucose residues being esterified with hexahydroxydiphenoyl) in rats fed polyphenol-rich diets. Their metabolites were identified and quantified in selected parts of the gastrointestinal tract, i.e., the stomach, small intestine, and cecum, on the second, fourth, and seventh days of the experiment, as well as in the rats' feces, blood serum, and urine. Significant differences between the metabolites of strawberry ellagitannins and ellagic acid were observed in all parts of the gastrointestinal tract. Urolithin A was the predominant polyphenolic metabolite of rats fed a diet supplemented with ellagic acid. On the other hand, in rats fed low degree of polymerization (DP) ellagitannins, the main metabolite was nasutin followed by urolithin A, while ellagitannins with a higher DP led to nasutin only.

Chemical Composition of Blackberry Press Cake, Polyphenolic Extract, and Defatted Seeds, and Their Effects on Cecal Fermentation, Bacterial Metabolites, and Blood Lipid Profile in Rats.

Blackberry fiber (BF), extracted blackberry fiber (EBF), defatted blackberry seeds (DBS), and blackberry polyphenols (BP) were added to the diets of rats. A control diet, fiber diets (BF, EBF, DBS) with 6% addition instead of cellulose, and a polyphenol diet (BP) with 1% addition were administered for 4 weeks. BF and DBS contained polyphenols (3.6%); EBF did not. DBS was free of fat. Ellagitannins were the main phenolics, mostly dimers (sanguiin H-6 with isomers) and monomers (pedunculagin, casuarictin isomer, and sanguiin H-2 isomer). Trimers (lambertianin C with isomers) and tetramers (lambertianin D) were in the minority. EBF increased the production of propionate and butyrate in the cecum and improved the blood lipid profile. Polyphenols beneficially decreased the activity of cecal ß-glucuronidase, but they may have also increased cholesterol levels in blood. Bacterial metabolism of ellagitannins in the colon gave rise to nasutin A and urolithin A.

The Fatty Acid Profile and Oxidative Stability of Meat from Turkeys Fed Diets Enriched with n-3 Polyunsaturated Fatty Acids and Dried Fruit Pomaces as a Source of Polyphenols.

The aim of this study was to determine the efficacy of different dietary fruit pomaces in reducing lipid oxidation in the meat of turkeys fed diets with a high content of n-3 polyunsaturated fatty acids (PUFAs). Over a period of 4 weeks before slaughter, turkeys were fed diets with the addition of 5% dried apple, blackcurrant, strawberry and seedless strawberry pomaces (groups AP, BP, SP and SSP, respectively) and 2.5% linseed oil. Pomaces differed in the content (from 5.5 in AP to 43.1 mg/g in SSP) and composition of polyphenols Proanthocyanidins were the main polyphenolic fraction in all pomaces, AP contained flavone glycosides and dihydrochalcones, BP contained anthocyanins, and SP and SSP-ellagitannins. The n-6/n-3 PUFA ratio in all diets was comparable and lower than 2:1. In comparison with groups C and AP, the percentage of n-3 PUFAs in the total fatty acid pool of white meat from the breast muscles of turkeys in groups BP, SP and SSP was significantly higher, proportionally to the higher content of α-linolenic acid in berry pomaces. The fatty acid profile of dark meat from thigh muscles, including the n-6/n-3 PUFA ratio, was similar and lower than 3:1 in all groups. Vitamin A levels in raw breast muscles were higher in group AP than in groups C and BP (P<0.05). The addition of fruit pomaces to turkey diets lowered vitamin E concentrations (P = 0.001) in raw breast muscles relative to group C. Diets supplemented with fruit pomaces significantly lowered the concentration of thiobarbituric acid reactive substances (TBARS) in raw, frozen and cooked meat. Our results indicate that the dietary application of dried fruit pomaces increases the oxidative stability of meat from turkeys fed linseed oil, and strawberry pomace exerted the most desirable effects due to its highest polyphenol content and antioxidant potential.

Metabolism of strawberry mono- and dimeric ellagitannins in rats fed a diet containing fructo-oligosaccharides.

PURPOSE: We investigated the effects of dietary supplementation with strawberry extracts rich in ETs and fructo-oligosaccharides (FOS) on the intestinal microbiota and the formation of bacterial metabolites in the distal intestine, as well as the absorption of ET metabolites and antioxidant status in rats. METHODS: Rats were allocated into six groups of eight animals each and fed for 4 weeks with a control diet (group C), a control diet supplemented with FOS (group C + FOS) or modifications of these diets, in which a monomeric or dimeric ET-rich extract was added (groups ME and ME + FOS or DE and DE + FOS, respectively). RESULTS: The extract addition, the FOS addition and their interaction significantly affected the total and selected bacterial counts in the caecal digesta (all P < 0.005). The total bacterial count was the highest in group C + FOS, lower in group DE and the lowest in group ME + FOS (10.6, 10.3 and 8.52 log cells/g, respectively; P ≤ 0.05). The total caecal content of ET metabolites was higher in the ME and ME + FOS group than in the DE and DE + FOS group, respectively (67.8 and 89.5 vs. 13.0 and 18.0 µg/g, respectively; P < 0.001). The total plasma concentration of ET metabolites was higher in the ME + FOS and DE + FOS group than in the ME group (248 and 281 vs. 8.13 ng/mL, respectively; P < 0.001). CONCLUSIONS: ETs of the monomeric ET-rich extract are more prone to intestinal breakdown than those of the dimeric ET-rich extract, and absorption of their metabolites can be increased by dietary FOS; however, together, they evoke strong antibacterial activity.

Anthocyanins in Strawberry Polyphenolic Extract Enhance the Beneficial Effects of Diets with Fructooligosaccharides in the Rat Cecal Environment.

The administration of fructooligosaccharides (FOS) beneficially modulates gastrointestinal functions and may enhance the metabolism of polyphenols. However, different polyphenolic components in the diet may have different influences on the activities of the digestive enzymes and microbiota in the gastrointestinal tract. Therefore, a 4-week study of forty-eight male Wistar rats was conducted to investigate the physiological response of the rat cecal environment to diets without and with FOS that contained two different strawberry polyphenolic extracts, specifically EP (polyphenolic profile 60, 35, 5, and 0% ellagitannins, proanthocyanidins, flavonols, anthocyanins, respectively) and EPA (polyphenolic profile: 50, 35, 6, and 9%, respectively). When combined with FOS, both extracts beneficially enhanced the acidification of the cecal digesta (P≤0.05 vs the groups without extracts), but the dietary combination of EPA and FOS elicited the greatest reduction in putrefactive short-chain fatty acid production and the lowest fecal ß-glucuronidase activity in the cecum (P≤0.05 vs group EP). Moreover, the addition of dietary FOS elevated the metabolism of the examined strawberry extracts in the cecum and thereby increased the concentrations of the metabolites in the cecal digesta and urine (P≤0.05 vs the group with cellulose). Overall, both strawberry extracts modulated the effects of FOS in the gastrointestinal tract; however, the combination with EPA extract that contained anthocyanins exhibited greater beneficial effects in the lower gut environment than the EP extract.

Chemical composition of polyphenols extracted from strawberry pomace and their effect on physiological properties of diets supplemented with different types of dietary fibre in rats.

PURPOSE: The objective of this study was to establish the composition of polyphenolic preparations obtained from industrial strawberry pomace with two methods of extraction: the water and the water-alcoholic one and then to analyse their effects in the gastrointestinal tract depending on the composition of dietary fibre-cellulose or fructooligosaccharides (FOS). METHODS: Freeze-dried water extract (PTW), containing 5.1% of ellagic acid, 0.2% of proanthocyanidins, and soluble carbohydrates as a major part, and water-alcohol extract (PTE), containing 17.1% of ellagic acid and 10.9% of proanthocyanidins, were administered, in the equivalent quantity of 0.06% of ellagic acid, to 4- to 8-week-old rats (8 animals per group), as a component of modified AIN-93 diets containing 5% of cellulose or FOS. RESULTS: The addition of strawberry pomace extracts had no effect on either the diet intake or the body weight of experimental rats. Both extracts, similarly to FOS, beneficially reduced the activity of ß-glucuronidase in caecal digesta, with the PTW effect being significantly higher than that of PTE (7.59 vs. 9.20 µmol/h/g, P = 0.001). In comparison with PTE, the PTW extract significantly increased the caecal digesta mass (1.45 vs. 1.27 k/kg BW) and the total production of SCFA (86.1 vs. 71.4 µmol/100 g BW). The extract enhanced the physiological effect of FOS by inhibiting the activity of ß-glucuronidase, increasing the caecal digesta mass and SCFA production. Such an effect was not recorded in the case of the PTE preparation. CONCLUSIONS: The addition of strawberry pomace extracts affected the activity of certain enzymes of intestinal microflora and its most important products.

Chemical composition of natural and polyphenol-free apple pomace and the effect of this dietary ingredient on intestinal fermentation and serum lipid parameters in rats.

Unprocessed pomace containing 61% of dietary fiber (DF) and 0.23% of polyphenols (PP) and ethanol- or ethanol/acetone-extracted pomaces containing 66% DF and 0.10% PP and 67% DF and 0.01% PP, respectively, were subjected to a 4 week study in rats. The aim of the study was assessing the advantages of dietary supplementation with the above pomaces. To measure the animal response to dietary treatments, parameters describing cecal fermentation and lipoprotein profile were assessed. The dietary use of 5% unprocessed pomace caused an increase in cecal short-chain fatty acid (SCFA) production and a decrease in blood triacylglycerols, leading to a drop in serum atherogenic index. Ethanol-extracted pomace increased the glycolytic activity of cecal microbiota and decreased cecal branched-chain fatty acid production, whereas acetone extraction led to lower cecal ammonia concentration, decreased colonic pH value, and higher HDL/total cholesterol ratio. The variations in the atherogenic index indicate flavonoids as the key pomace component in relation to blood lipid profile benefits.

Characterization of cell wall polysaccharides of cherry (Prunus cerasus var. Schattenmorelle) fruit and pomace.

The polysaccharide composition of cell wall of sour cherry (Prunus cerasus var. Schattenmorelle) fruit and pomace was investigated. Furthermore, the alcohol insoluble solids composition of 'Kelleriis' and 'Dobreczyn Botermo' varieties were studied too. Yield of alcohol insoluble solids for fruits was lower than 10%, and for pomaces circa 50%. Uronic acid was the main pectin component of alcohol insoluble solids. Enzymes used as juice processing aids decreased the content of uronic acid. Araban and galactan side chains bonded tightly to cellulose presence was suggested by high content of arabinose and galactose in hemicellulose fraction. The process of drying at below 70 degrees C did not influence polysaccharide composition of sour cherry pomaces. Alcohol insoluble solids of fruits expressed higher hydration properties than of pomaces.