Revistas
Revista:
FOOD CHEMISTRY
ISSN:
0308-8146
Año:
2022
Vol.:
367
Págs.:
130620
Artichokes are a rich source of (poly)phenols, mainly caffeoylquinic acids, but little is known about their bioavailability from this source. This study investigated the absorption, metabolism and excretion of (poly)phenols after sous-vide artichoke consumption (5776 µmol of (poly)phenols) by healthy volunteers. Seventy-six (poly)phenol metabolites were identified by UHPLC-MS/MS using authentic standards, including acyl-quinic acids plus C6¿C3, C6¿C1, C6¿C2, C6¿C1¿N, C6¿C0 metabolites, and their phase-II conjugates. The major metabolites were 3¿-methoxy-4¿-hydroxycinnamic acid, 3¿-methoxycinnamic acid-4¿-sulfate, and 4¿-hydroxycinnamic acid-3¿-sulfate, which appeared early in plasma (Tmax < 4 h); plus 3-(3¿-methoxy-4¿-hydroxyphenyl)propanoic acid, 3-(4¿-methoxyphenyl)propanoic acid-3¿-glucuronide, 3-(3¿-hydroxyphenyl) propanoic acid and hippuric acids, which appeared later (Tmax > 6 h). The 24 h urinary recovery averaged 8.9% (molar basis) of the (poly)phenols consumed. Hepatic beta-oxidation of 3¿,4¿-dihydroxycinnamic acid and methylated conjugates occurred, but was limited (<0.04%). 3¿-Methylation exceeded 4¿-methylation and interindividual variability was high, especially for gut microbial metabolites (up to 168-fold).
Autores:
Macià, A.; Romero, M. P.; Yuste, S.; et al.
Revista:
FOOD CHEMISTRY
ISSN:
0308-8146
Año:
2022
Vol.:
384
Págs.:
132612
The present study aimed to evaluate the metabolism and bioavailability of anthocyanins (ACN) and other phenolics from red-fleshed apple (RFA) and to define the intake biomarkers compared to common white-fleshed apple (WFA). Acute and sustained (6-week) interventions were combined in a randomized, controlled and parallel study with 121 hypercholesterolemic subjects. Another arm consuming ACN-rich infusion from aronia fruit (ARO) provided matched content and profile of ACN. Plasma, urine and faeces samples were analyzed using UPLC-MS/MS. Results showed higher bioavailability of ACN after ARO compared to RFA, showing a clear apple matrix effect. The dihydrochalcone phloretin-2'-O-glucuronide was the most discriminant intake biomarker of both apples. The urinary peonidin-3-O-galactoside was a good biomarker after both ARO and RFA intakes, whereas peonidin-O-arabinoside was reported to be specific from ARO. The elucidation of the phenolic metabolism and the selection of intake biomarkers is a promising approach to relate phenolic compounds and human health.
Revista:
MECHANISMS OF AGEING AND DEVELOPMENT
ISSN:
0047-6374
Año:
2022
Vol.:
204
Págs.:
111668
It has been established that ageing is the major risk factor for cognitive deficiency and it is becoming increasingly evident that insulin resistance is another factor. Biological plausibility for a link between insulin resistance and dementia is relevant for understanding disease etiology, and to form bases for prevention efforts to decrease disease burden. In the present study, peripheral and central insulin resistance was found in SAMP8 mice (aging mouse model) accompanied by cognitive deficiencies. Furthermore, a marked peripheral inflammatory state was observed in SAMP8 mice, followed by neuroinflammation that could be due to a higher cytokine leaking into the brain across an aging-disrupted blood brain barrier. Moreover, aging-induced gut dysbiosis produces higher TMAO that could also contribute to the peripheral and central inflammatory tone as well as to the cognitive deficiencies observed in SAMP8 mice. All those alterations were reversed by DMB, a treatment that decreases TMAO levels. Data obtained from this project suggest that microbial dysbiosis and increased TMAO secretion could be a key link between aging, insulin resistance and dementia. Thus, pharmacological intervention that leads to decreased TMAO levels, such as DMB, could open a new avenue for the future treatment of neurodegenerative diseases.
Revista:
FOOD & FUNCTION
ISSN:
2042-6496
Año:
2021
Vol.:
12
N°:
5
Págs.:
1996 - 2011
The aim of this study was to evaluate the bioaccessibility of (poly)phenolic compounds in Tudela artichokes (Cynara scolymus cv. Blanca de Tudela) after an in vitro gastrointestinal digestion and the effect of the human colonic microbiota. A total of 28 (poly)phenolic compounds were identified and quantified by LC-MS/MS in raw, boiled, sous vide and microwaved Tudela artichokes. Out of these, sixteen were phenolic acids, specifically caffeoylquinic acids (CQAs) and other minor hydroxycinnamic acid derivatives, ten flavonoids belonging to the family of flavones (apigenin and luteolin derivatives) and two lignans (pinoresinol derivatives). Sous vide and microwaving caused mainly transesterification reactions of CQAs but maintained or even augmented the total (poly)phenolic contents of artichokes, while boiling decreased (poly)phenolic compounds by 25% due to leaching into the boiling water. Heat treatment exerted a positive effect on the bioaccessibility of (poly)phenols after gastrointestinal digestion. In raw artichokes, only 1.6% of the total (poly)phenolic compounds remained bioaccessible after gastrointestinal digestion, while in artichoke samples cooked by sous vide, boiled and microwaved, the percentage of bioaccessibility was 60.38%, 59.93% and 39,03% respectively. After fecal fermentation, 20 native (poly)phenolic compounds and 11 newly formed catabolites were quantified. 48 h of fecal fermentation showed that native (poly)phenols are readily degraded by colonic microbiota during the first 2 h of incubation. The colonic degradation of artichoke (poly)phenols follows a major pathway that involves the formation of caffeic acid, dihydrocaffeic acid, 3-(3 '-hydroxyphenyl)propionic acid, 3-phenylpropionic acid and phenylacetic acid, with 3-phenylpropionic acid being the most abundant end product. The catabolic pathways for colonic microbial degradation of artichoke CQAs are proposed.
Revista:
INTERNATIONAL JOURNAL OF GASTRONOMY AND FOOD SCIENCE
ISSN:
1878-450X
Año:
2021
Vol.:
25
Págs.:
100389
Artichokes are an important source of (poly)phenolic compounds, mainly caffeoylquinic acids, which consumption has been associated with health benefits. However, heat treatments have shown to affect the amounts of these bioactive food compounds.
In the present study the influence of culinary techniques (boiling, griddling, and frying) on the total (poly)phenolic content of artichokes (Cynara Scolymus cv. Blanca de Tudela) was evaluated by LC-MS/MS. Additionally, the antioxidant capacity of cooked artichokes was evaluated by spectrophotometric methods.
A total of 31 (poly)phenols were identified and quantified, being caffeoylquinic acids the most abundant compounds in raw artichokes accounting for more than 95% of total (poly)phenolic compounds. With the different culinary techniques, these compounds suffered degradation but also redistribution, probably due to isomerization and hydrolysis reactions. Frying and griddling showed the lowest content of (poly)phenolic compounds and antioxidant capacity suggesting thermal degradation. Boiling also provoked losses, which were mainly due to leaching of phenolic compounds into the water. However, it was the heat treatment that best preserved (poly)phenolic compounds in artichokes.
Revista:
MOLECULAR NUTRITION AND FOOD RESEARCH
ISSN:
1613-4125
Año:
2021
Vol.:
65
N°:
10
Págs.:
e2001225
The present study aims to investigate the metabolic fate and the cardiometabolic effects of phenolic compounds provided by a red-fleshed apple variety biofortified in anthocyanins (ACN). Wistar rats are fed with high-fat diet (HFD) to induce hypercholesterolemia and supplemented with red-fleshed apple (HFD+R), white-fleshed apple (HFD+W), or an ACN-rich infusion from aronia fruit (HFD+A) providing matched content and profile of ACN. Plasma biochemical parameters, histological analysis, and phenol biological metabolites are determined. Plasma, urine, and feces show a significant increase of ACN metabolites after HFD+R and HFD+A, while flavan-3-ols are significantly increased after HFD+W and dihydrochalcones derivatives increased after both apples supplementation. A cardioprotective effect is observed after both apples and aronia infusion supplementation in the reduction of aortic thickness. The kidney function is improved after all supplementations and a decrease in insulin plasma concentration after both apples supplementation (HFD+R and HFD+W) is also observed. The findings support that ACN without apple matrix can induce cardioprotective effects. ACN or flavan-3-ols, together with dihydrochalcones, compose a phenolic phytocomplex in red- and white-fleshed apples, respectively, which can act synergistically in the attenuation of cardiovascular outcomes in hypercholesterolemic rats.
Revista:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN:
0021-8561
Año:
2021
Vol.:
69
N°:
1
Págs.:
537 - 554
Many studies have associated the consumption of (poly)phenol-rich diets with health benefits. However, accurate high-throughput quantitative methods for estimating exposure covering a broad spectrum of (poly)phenols are lacking. We have developed and validated a high-throughput method for the simultaneous quantification of 119 (poly)phenol metabolites in plasma and urine using ultra high-performance liquid chromatography coupled with triple quadrupole mass spectrometry, with a very fast sample treatment and a single run time of 16 min. This method is highly sensitive, precise, accurate, and shows good linearity for all compounds (R2 > 0.992). This novel method will allow a quantitative assessment of habitual (poly)phenol intake in large epidemiological studies as well as clinical studies investigating the health benefits of dietary (poly)phenols.
Revista:
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
ISSN:
1570-0232
Año:
2020
Vol.:
1152
Págs.:
122247
The analysis of the fat-soluble vitamins A and E and lipid micronutrients in blood, such as carotenoids, is an important parameter to monitor the micronutrient status in humans. Although the potential of dried blood spot (DBS) cards, the use of this technique for blood sampling and subsequent analysis of these fat-soluble micronutrients has been poorly or not studied. An analytical method based on DBS cards (FTA® DMPK-A) combined with liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) has been developed and validated for the determination of carotenoids (lutein, zeaxanthin, ß-cryptoxanthin and ß-carotene), tocopherols (¿-tocopherol, ¿-tocopherol and ¿-tocopherol) and all-trans-retinol in human blood. Under optimum DBS card extraction conditions, the extraction recoveries of the studied compounds were higher than 72%, the sample matrix effect lower than 17%, and the detection limits at hundred nM concentration levels. The developed method was applied to the analysis of human blood, and the concentration ranges obtained fell within the expected ranges previously reported in healthy adults. Moreover, the influence of hematocrit effect was investigated in a range of 25-55% in order to compare the obtained results to those reported in the literature for the analysis of plasma samples. This method represents an improvement over current techniques reported in the literature due to the use of a non-invasive blood collection method, and moreover, this methodology was for the first time 1) validated for the analysis of all-trans-retinol, tocopherols and carotenoids, and 2) applied for the determination of tocopherols in human blood samples.
Autores:
Calderón-Pérez, L. ; Gosalbes, M. J.; Yuste, S. ; et al.
Revista:
SCIENTIFIC REPORTS
ISSN:
2045-2322
Año:
2020
Vol.:
10
N°:
1
Págs.:
6436
Hypertension is an independent and preventable risk factor for the development of cardiovascular diseases, however, little is known about the impact of gut microbiota composition in its development. We carried out comprehensive gut microbiota analysis and targeted metabolomics in a cross-sectional study of 29 non-treated hypertensive (HT) and 32 normotensive (NT) subjects. We determined fecal microbiota composition by 16S rRNA gene sequencing and bacterial functions by metagenomic analysis. The microbial metabolites analysed were short chain fatty acids (SCFA) both in plasma and feces, and trimethylamine N-oxide (TMAO) in plasma. The overall bacterial composition and diversity of bacterial community in the two groups were not significantly different. However, Ruminococcaceae NK4A214, Ruminococcaceae_UCG-010, Christensenellaceae_R-7, Faecalibacterium prausnitzii and Roseburia hominis were found to be significantly enriched in NT group, whereas, Bacteroides coprocola, Bacteroides plebeius and genera of Lachnospiraceae were increased in HT patients. We found a positive correlation between the HT-associated species and systolic and diastolic blood pressure after adjusted for measured confounders. SCFA showed antagonistic results in plasma and feces, detecting in HT subjects significant higher levels in feces and lower levels in plasma, which could indicate a less efficient SCFA absorption. Overall, our results present a disease classifier based on microbiota and bacterial metabolites to discriminate HT individuals from NT controls in a first disease grade prior to drug treatment.
Autores:
Pereira-Caro, G. (Autor de correspondencia); Clifford, M. N.; Polyviou, T.; et al.
Revista:
FREE RADICAL BIOLOGY AND MEDICINE
ISSN:
0891-5849
Año:
2020
Vol.:
160
Págs.:
784 - 795
The health benefits of orange juice (OJ) consumption are attributed in part to the circulating flavanone phase II metabolites and their microbial-derived ring fission phenolic catabolites. The present study investigated these compounds in the bloodstream after acute intake of 500 mL of OJ. Plasma samples obtained at 0, 1, 2, 3, 4, 5, 6, 7, 8 and 24 h after OJ intake were analysed by HPLC-HR-MS. Eleven flavanone metabolites and 36 phenolic catabolites were identified and quantified in plasma. The main metabolites were hesperetin-3'-sulfate with a peak plasma concentration (C-max) of 80 nmol/L, followed by hesperetin-7-glucuronide (C-max 24 nmol/L), hesperetin-3'-glucuronide (C-max 18 nmol/L) and naringenin-7-glucuronide (C-max 21 nmol/L). Among the main phenolic catabolites to increase in plasma after OJ consumption were 3'-methoxycinnamic acid-4'-sulfate (C-max 19 nmol/L), 3-hydroxy-3-(3'-hydroxy-4'-methoxyphenyl)propanoic acid (C-max 20 nmol/L), 3-(3'-hydroxy-4'-methoxyphenyl)propanoic acid (C-max 19 nmol/L), 3-(4'- hydroxyphenyl)propanoic acid (C-max 25 nmol/L), and 3(phenyl)propanoic acid (C-max 19 nmol/L), as well as substantial amounts of phenylacetic and hippuric acids. The comprehensive plasma pharmacokinetic profiles that were obtained are of value to the design of future ex vivo cell studies, aimed at elucidating the mechanisms underlying the potential health benefits of OJ consumption.
Autores:
Yuste, S. ; Macia, A. ; Motilva, M. J.; et al.
Revista:
FOOD & FUNCTION
ISSN:
2042-6496
Año:
2020
Vol.:
11
N°:
12
Págs.:
10436 - 10447
The present study evaluated the impact of different thermal (infrared-drying, hot air-drying and puree pasteurization) and non-thermal (freeze-drying) processing technologies on red-fleshed apple (poly)phenolic compounds. We further investigated the processing effect on the (poly)phenol bioavailability in a crossover postprandial study where three subjects consumed three apple products (freeze-dried snack, hot air-dried snack and pasteurized puree). (Poly)phenolic compounds present in the apple products and their biological metabolites in urine were analyzed using liquid chromatography coupled to mass spectrometry (UPLC-MS/MS). When comparing different processes, infrared-drying caused important losses in most of the apple (poly)phenolics, while hot air-drying and puree pasteurization maintained approximately 83% and 65% of total (poly)phenols compared with the freeze-dried snack, respectively. Anthocyanins in particular were degraded to a higher extent, and hot air-dried apple and pasteurized puree maintained respectively 26% and 9% compared with freeze-dried apple snack. The acute intake showed that pasteurized puree exhibited the highest (poly)phenol bioavailability, followed by hot air-drying and freeze-dried snack, highlighting the impact of processing on (poly)phenols absorption. In conclusion, for obtaining affordable new red-fleshed apple products with enhanced (poly)phenol bioavailability, puree pasteurization and hot air-drying represent viable techniques. However, to obtain a red-fleshed apple snack with high anthocyanin content, freeze-drying is the technique that best preserves them.
Autores:
Granado-Serrano, A. B.; Martín-Garí, M.; Sánchez, V.; et al.
Revista:
SCIENTIFIC REPORTS
ISSN:
2045-2322
Año:
2019
Vol.:
9
N°:
1
Págs.:
1772
Gut microbiota has been suggested to affect lipid metabolism. The objective of this study was to characterize the faecal microbiota signature and both short chain fatty acids (SCFAs) and bile acids (BA) profile of hypercholesterolemic subjects. Microbiota composition, SCFAs, BA and blood lipid profile from male volunteers with hypercholesterolemia (HC) and normocholesterolemia (NC) were determined by 16S rDNA sequencing, HPLC, GC and NMR, respectively. HC subjects were characterized by having lower relative abundance of Anaeroplasma (0.002% vs 0.219%, p-value = 0.026) and Haemophilus (0.041% vs 0.078%, p-value = 0.049), and higher of Odoribacter (0.51% vs 0.16%; p-value = 0.044). Correlation analysis revealed that Anaeroplasma and Haemophilus were associated to an unfavourable lipid profile: they correlated negatively to cholesterol and triglycerides related biomarkers and the ratio total to high density lipoprotein (HDL) cholesterol, and positively to HDL size. Odoribacter displayed an opposite behaviour. Faecal SCFAs profile revealed higher abundance of isobutyric (2.76% vs 0.82%, p-value = 0.049) and isovaleric acid (1.32% vs 0.06%, p-value = 0.016) in HC. Isobutyric acid correlated positively with Odoribacter and lipid parameters indicative of an unfavourable profile. BA profile did not show differences between groups. It was concluded that HC subjects showed a particular faecal bacterial signature and SCFAs profile associated with their lipid profile.
Revista:
JOURNAL OF FUNCTIONAL FOODS
ISSN:
1756-4646
Año:
2019
Vol.:
55
Págs.:
146 - 155
The aim of this study was to investigate comprehensively the metabolic pathways and human bioavailability of anthocyanins and other (poly)phenols in an apple matrix, and to elucidate potential intake biomarkers. After the acute intake of a red-fleshed apple freeze-dried snack, plasma and urine were collected and analyzed by UPLC-MS/MS. A total of 37 phase-II and microbial phenolic metabolites were detected in plasma and urine. Among these, phloretin glucuronide, cyanidin-3-O-galactoside (plasma and urine) and peonidin-3-O-galactoside (urine) were the only metabolites detected in all the volunteers and not detected at basal conditions. The maximum urine excretion was detected at 2-4 h, and the main increase in plasma of phloretin glucuronide and cyanidin-3-O-galactoside was observed at 2 h post-intake (61.0 +/- 6.82 and 10.3 +/- 1.50 nM, respectively). These metabolites could be selected as the best intake biomarkers of red-fleshed apple and might be useful in human intervention studies when studying its health effects.
Autores:
Mena, P. (Autor de correspondencia); Ludwig, Iziar A.; Tomatis, V. B.; et al.
Revista:
EUROPEAN JOURNAL OF NUTRITION
ISSN:
1436-6207
Año:
2019
Vol.:
58
N°:
4
Págs.:
1529 - 1543
PurposeThere is much information on the bioavailability of (poly)phenolic compounds following acute intake of various foods. However, there are only limited data on the effects of repeated and combined exposure to specific (poly)phenol food sources and the inter-individual variability in their bioavailability. This study evaluated the combined urinary excretion of (poly)phenols from green tea and coffee following daily consumption by healthy subjects in free-living conditions. The inter-individual variability in the production of phenolic metabolites was also investigated.MethodsEleven participants consumed both tablets of green tea and green coffee bean extracts daily for 8 weeks and 24-h urine was collected on five different occasions. The urinary profile of phenolic metabolites and a set of multivariate statistical tests were used to investigate the putative existence of characteristic metabotypes in the production of flavan-3-ol microbial metabolites.Results(Poly)phenolic compounds in the green tea and green coffee bean extracts were absorbed and excreted after simultaneous consumption, with green tea resulting in more inter-individual variability in urinary excretion of phenolic metabolites. Three metabotypes in the production of flavan-3-ol microbial metabolites were tentatively defined, characterized by the excretion of different amounts of trihydroxyphenyl--valerolactones, dihydroxyphenyl--valerolactones, and hydroxyphenylpropionic acids.ConclusionsThe selective ...
Autores:
Ordóñez, J. L.; Pereira-Caro, G. (Autor de correspondencia); Ludwig, Iziar A.; et al.
Revista:
JOURNAL OF CHROMATOGRAPHY A
ISSN:
0021-9673
Año:
2018
Vol.:
1575
Págs.:
100 - 112
The present study compared and validated two analytical methods, HPLC-HRMS, and GC-MS using MSTFA as derivatization agent, for the analysis of microbiota-derived phenolic acids and aromatic compounds accumulating in urine, collected over a 24 h period after the consumption of 500 mL of orange juice. In addition, purification procedures using SDB-L and HLB solid phase cartridges were compared when HPLC- HRMS technique was used. Both HPLC-HRMS and GC-MS methodologies were successfully validated in terms of specificity, sensitivity, limit of detection and quantification, recovery and matrix effects. HPLC- HRMS, unlike GC-MS, does not require sample derivatization prior to analysis. GC-MS was not suitable for the analysis of phenolic sulfate and glucuronide metabolites because of their lack of volatility. These phase II metabolites could, however, be analysed by HPLC-HRMS which, as a consequence, provided more detailed and complete information on the phenolic compounds derived from microbiota-mediated degradation of orange juice (poly)phenols. Furthermore, the use of SDB-L and HLB cartridges for sample purification prior to HPLC-HRMS analysis is suitable for free phenolics and glucuronide metabolites but not sulfate derivatives. These findings highlight that the use of an inappropriate analytical protocol can adversely affect studies on the bioavailability of dietary (poly)phenols in which microbiota-derived phenolic catabolites play an important role.
Revista:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN:
0021-8561
Año:
2018
Vol.:
66
N°:
34
Págs.:
8966 - 8975
Among cereals, barley (Hordeum vulgare L.) is notable for its high content of bioactives such as beta-glucan and phenolic compounds, but it is not used as widely in human nutrition as wheat. To compare the impact of food formulation and processing on barley bioactives, crackers, cookies, and fresh pasta were prepared combining wheat and barley flour. After quantification of beta-glucan and PCs in the barley flour and barley-based products, their behavior during in vitro gastrointestinal digestion and colonic fermentation was studied. The beta-glucan and PCs were not drastically affected by processing. The amount of bioaccessible compounds after gastrointestinal digestion was lower than the amount retained in the undigested fraction. After in vitro colonic fermentation, beta-glucan was mainly metabolized to acetic and propionic acids and PCs to phenylpropionic and phenylacetic acids. Based on the results of the study, the daily ingestion of barley-based foods may contribute to the intake of beneficial bioactive compounds.
Autores:
Pereira-Caro, G. (Autor de correspondencia); Fernandez-Quirós, B.; Ludwig, Iziar A.; et al.
Revista:
EUROPEAN JOURNAL OF NUTRITION
ISSN:
1436-6207
Año:
2018
Vol.:
57
N°:
1
Págs.:
231 - 242
Purpose Orange juice (OJ) flavanones undergo limited absorption in the upper gastrointestinal tract and reach the colon where they are transformed by the microbiota prior to absorption. This study investigated the ability of two probiotic bacteria, Bifidobacterium longum R0175 and Lactobacillus rhamnosus subsp. Rhamnosus NCTC 10302 to catabolise OJ flavanones.
Methods The bacteria were incubated with hesperetin-7-Orutinoside, naringenin-7-O-rutinoside, hesperetin and naringenin, and the culture medium and intracellular cell extracts were collected at intervals over a 48 h of incubation period. The flavanones and their phenolic acid catabolites were identified and quantified by HPLC-HR-MS.
Results Both probiotics were able to subject hesperetin to ring fission yielding 3-(3'-hydroxy-4'-methoxyphenyl)propionic acid which was subsequently demethylated producing 3-(3', 4'-dihydroxyphenyl)propionic acid and then via successive dehydroxylations converted to 3-(3'-hydroxyphenyl)propionic acid and 3-(phenyl)propionic acid. Incubation of both bacteria with naringenin resulted in its conversion to 3-(4'-hydroxyphenyl)propionic acid which underwent dehydroxylation yielding 3-(phenyl)propionic acid. In addition, only L. rhamnosus exhibited rhamnosidase and glucosidase activity and unlike B. longum, which was able to convert hesperetin-7-O-rutinoside and naringenin-7-O-rutinoside to their respective aglycones. The aglycones were then subjected to ring fission and further catabolised...
Autores:
Pereira-Caro, G. (Autor de correspondencia); Ordóñez, J. L.; Ludwig, Iziar A.; et al.
Revista:
FOOD CHEMISTRY
ISSN:
0308-8146
Año:
2018
Vol.:
252
Págs.:
49 - 60
This study developed, optimized and validated an ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HRMS) method to identify and quantify metabolites and microbial-derived catabolites in urine, plasma and feces of rats following ingestion of 50 mg of a red wine proanthocyanidin-rich extract. The method was validated for specificity, linearity, limit of detection (LD) and quantification (LQ), intra-day and inter-day precision, recovery and matrix effects, which were determined for 34 compounds in the three biological matrices. After method validation, three parent flavan-3-ols, four 5-carbon side chain ring fission metabolites, and 27 phenolic acid and aromatic catabolites were quantified in plasma, urine and feces after red wine proanthocyanidin intake. These results establish the value of the UHPLC-HRMS protocol in obtaining a detailed picture of proanthocyanidin metabolites and their microbial-derived catabolites, along with their phase II metabolites, in biological fluids of rat, and potentially in human clinical studies designed to evaluate the bioavailability of dietary flavan-3-ols.
Autores:
Martínez, M.; Motilva, M. J.; Lopez de las Hazas, M. C.; et al.
Revista:
FOOD CHEMISTRY
ISSN:
0308-8146
Año:
2018
Vol.:
245
Págs.:
61 - 70
In the present study, 27 barley genotypes (Hordeum vulgare L.) grown in two geographic origins (Czech Republic and Spain) were analysed for their contents of beta-glucan, tocols and phenolic compounds (free and bound). The samples included hulled, hull-less and coloured genotypes. The results showed that concentrations of beta-glucan range from 2.40 to 7.42 g/100 g. Total tocol content of the barley samples ranged between 39.9 and 81.6 mu g/g. A total of 64 compounds were identified in the barley samples. These included 19 phenolic acids and aldehydes, 9 flavan 3-ols, 9 flavone glycosides, and 27 anthocyanins. The results showed a wide range of phenolic concentrations in the barley samples, highlighting the presence of considerable amounts of anthocyanins in purple barley genotypes. In synthesis, barley should be considered a good source of bioactive components, especially because of the broad spectrum of phytochemicals with potential health benefits besides the soluble fibre (beta-glucan).
Revista:
MOLECULAR NUTRITION AND FOOD RESEARCH
ISSN:
1613-4125
Año:
2018
Vol.:
62
N°:
23
Págs.:
1800623
Scope: The application of dried blood spot (DBS) cards for the study in human blood of dietary polyphenol bioavailability has been poorly studied.
Methods and results: An analytical method based on blood sampling with DBS cards combined with LC-MS/MS has been developed and validated. To test the method validation, the phenolic metabolites are determined in human blood and plasma obtained after an acute intake of a red-fleshed apple snack in ten volunteers. Capillary blood by finger prick is compared to venous blood by venipuncture and whole blood is also compared to their corresponding venous plasma samples. Moreover, the venous plasma results using DBS cards are compared to those obtained by microElution solid phase extraction (mu SPE). The main phenolic metabolites detected in blood and plasma samples are phloretin glucuronide, dihydroxyphenylpropionic acid sulphate, (methyl) catechol sulphate, catechol glucuronide, and hydroxyphenyl-gamma-valerolactone glucuronide. No significant differences are observed between capillary blood, venous blood, and plasma samples using DBS, and neither between plasma samples analyzed by DBS or mu SPE.
Conclusions: Finger-prick blood sampling based on DBS appears to be a suitable alternative to the classic invasive venipuncture for the determination of circulating phenolic metabolites in nutritional postprandial studies.
Revista:
JOURNAL OF FUNCTIONAL FOODS
ISSN:
1756-4646
Año:
2017
Vol.:
32
Págs.:
195 - 207
A total of 17 (poly)phenolic compounds have been quantified in the free and bound fraction of raw, olive oil fried, sunflower oil fried and griddled cardoon (Cynara cardunculus L.). Caffeoylquinic acid derivatives (CQAs), particularly 5-CQA, were the major compounds. The bioaccessibility of (poly)phenols after gastrointestinal digestion and fecal fermentation (24 h) was studied. Heat treatment exerted a positive effect on the bioaccessibility of (poly)phenols. In raw cardoon, only 2% of the total amount of (poly)phenolic compounds was still bioaccessible after gastrointestinal digestion, while in cooked cardoon samples, between 60 and 67% of the total amount of (poly)phenolic compounds remained unmodified. An important microbial metabolic activity was observed during the fecal fermentation, which resulted in a complete degradation of CQAs after 5 h and in the formation of different catabolites. 3-(3¿-hydroxyphenyl)propionic acid was by far the most abundant catabolite produced. Catabolic pathways for colonic microbial degradation of CQAs of cardoon have been proposed.
Revista:
AMERICAN JOURNAL OF CLINICAL NUTRITION
ISSN:
0002-9165
Año:
2017
Vol.:
106
N°:
3
Págs.:
791 - 800
Background: Physical exercise has been reported to increase the bioavailability of citrus flavanones.
Objective: We investigated the bioavailability of orange juice (OJ) (poly) phenols in endurance-trained males before and after cessation of training for 7 d.
Design: Ten fit, endurance-trained males, with a mean +/- SD maximal oxygen consumption of 58.2 +/- 5.3 mL.kg(-1) min 21, followed a low (poly) phenol diet for 2 d before drinking 500 mL of OJ containing 398 mu mol of (poly) phenols, of which 330 mu mol was flavanones. After the volunteers stopped training for 7 d the feeding study was repeated. Urine samples were collected 12 h pre-and 24 h post-OJ consumption. Bioavailability was assessed by the quantitative analysis of urinary flavanone metabolites and (poly) phenol catabolites with the use of high-pressure liquid chromatography-high resolution mass spectrometry.
Results: During training, 0-24-h urinary excretion of flavanone metabolites, mainly hesperetin-3'-O-glucuronide, hesperetin-3'-sulfate, naringenin-4'-O-glucuronide, naringenin-7-O-glucuronide, was equivalent to 4.2% of OJ flavanone intake. This increased significantly to 5.2% when OJ was consumed after the volunteers stopped training for 7 d. Overall, this trend, although not significant, was also observed with OJ-derived colonic catabolites, which, after supplementation in the trained state, were excreted in amounts equivalent to 51% of intake compared with 59% after cessation of training. However, ...
Autores:
López de las Hazas, M. C.; Mosele, J. I.; Macià, A.; et al.
Revista:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN:
0021-8561
Año:
2017
Vol.:
65
N°:
31
Págs.:
6477 - 6487
Beneficial properties attributed to the intake of fruit and red wine have been associated with the presence of significant amounts of anthocyanins. However, their low absorption and consequent accumulation in the gut have generated the suspicion that colonic metabolites of anthocyanins are probably involved in these protective effects. Grape pomace and strawberry extracts, rich in malvidin-and pelargonidin-glucoside, respectively, were fermented in vitro using human feces as microbial inoculum. After 8 h of anaerobic incubation, the anthocyanins were almost completely degraded, whereas their microbial metabolite concentrations were highest at 24 h. Syringic acid and tyrosol were the main metabolites,of grape and strawberry extracts, respectively. On the basis of the metabolites. detected, metabolic pathways of malvidin-and pelargonidin-glucosides Were proposed. Anthocyanin-rich grape and strawberry extracts and their, generated metabolites such as hydroxyphenylacetic acid showed apoptotic effects in HT-29 colon cancer cells and may suggest their possible contribution as anticarcinogenic agents.
Revista:
MOLECULAR NUTRITION AND FOOD RESEARCH
ISSN:
1613-4125
Año:
2017
Vol.:
61
N°:
9
Págs.:
1700055
Scope: Previous studies have proposed that phytosterols activate liver X receptors (LXR) in the intestine, thereby reducing intestinal cholesterol absorption and promoting fecal cholesterol excretion.
Methods and results: In the present study, we examined the effects of dietary phytosterol supplementation on intestinal cholesterol absorption and fecal neutral sterol excretion in LXR alpha beta-deficient mice, and wild-type mice treated with synthetic high-affinity LXR alpha beta agonists. LXR alpha beta deficiency led to an induction of intestinal cholesterol absorption and liver cholesterol accumulation. Phytosterol feeding resulted in an approximately 40% reduction of intestinal cholesterol absorption both in wild-type and LXR alpha beta-deficient mice, reduced dietary cholesterol accumulation in liver and promoted the excretion of fecal cholesterol-derived compounds. Furthermore, phytosterols produced additive inhibitory effects on cholesterol absorption in mice treated with LXR alpha beta agonists.
Conclusions: Our data confirm the effect of LXR in regulating intestinal cholesterol absorption and demonstrate that the cholesterol-lowering effects of phytosterols occur in an LXR-independent manner.
Revista:
JOURNAL OF FUNCTIONAL FOODS
ISSN:
1756-4646
Año:
2016
Vol.:
27
Págs.:
201 - 213
A total of 21 (poly)phenolic compounds (free and bound) were quantified in raw, olive oil fried, sunflower oil fried and griddled green pepper before and after a simulated gastrointestinal digestion. Flavonoids, particularly quercetin rhamnoside, were the main compounds. The bioaccessibility of (poly)phenolic compounds after gastrointestinal digestion was higher in cooked (>82%) than in raw (48%) samples, showing a positive effect of heat treatment on the release of (poly)phenols from the vegetal matrix. Additionally, a faecal fermentation was carried out for 24h. A time-dependent microbial metabolic activity was observed, which resulted firstly (<5h) in the hydrolysis of flavonoid glycosides and then in the formation of 3 catabolites, namely 3,4-dihydroxybenzoic acid, dihydrocaffeic acid and 3-(3¿-hydroxyphenyl)propionic acid, this being by far the most abundant. Catabolic pathways for colonic microbial degradation of flavonoids and hydroxycinnamic acids have been proposed. Griddled pepper showed the highest amount of (poly)phenols both after gastrointestinal digestion and colonic fermentation.
Revista:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN:
0021-8561
Año:
2016
Vol.:
64
N°:
28
Págs.:
5724 - 5735
Orange juice is a rich source of (poly)phenols, in particular, the flavanones hesperetin-7-O-rutinoside and naringenin-7-O-rutinoside. Following the acute consumption of 500 mL of orange juice containing 398 mu mol of (poly)phenols by 12 volunteers, 0-24 h plasma and urine samples were analyzed by targeted high-performance liquid chromatography-high resolution mass spectrometry in order to identify flavanone metabolites and phenolic acid and aromatic catabolites. A total of 19 flavanone metabolites-comprising di-O-glucuronide, O-glucuronide, O-glucuronyl-sulfate, and sulfate derivatives of hesperetin, naringenin, and eriodictyol-and 65 microbial-derived phenolic catabolites, such as phenylpropanoid, phenylpropionic, phenylacetic, benzoic, and hydroxycarboxylic acids and benzenetriol and benzoylglycine derivatives, including free phenolics and phase II sulfate, glucuronide, and methyl metabolites, were identified or partially identified in plasma and/or urine samples. The data obtained provide a detailed evaluation of the fate of orange juice (poly)phenols as they pass through the gastrointestinal tract and are absorbed into the circulatory system prior to renal excretion. Potential pathways for these conversions are proposed.
Revista:
FOOD CHEMISTRY
ISSN:
0308-8146
Año:
2016
Vol.:
197
Págs.:
466 - 473
The impact of cooking heat treatments (frying in olive oil, frying in sunflower oil and griddled) on the antioxidant capacity and (poly) phenolic compounds of onion, green pepper and cardoon, was evaluated. The main compounds were quercetin and isorhamnetin derivates in onion, quercetin and luteolin derivates in green pepper samples, and chlorogenic acids in cardoon. All heat treatments tended to increase the concentration of phenolic compounds in vegetables suggesting a thermal destruction of cell walls and sub cellular compartments during the cooking process that favor the release of these compounds. This increase, specially that observed for chlorogenic acids, was significantly correlated with an increase in the antioxidant capacity measured by DPPH (r = 0.70). Griddled vegetables, because of the higher temperature applied during treatment in comparison with frying processes, showed the highest amounts of phenolic compounds with increments of 57.35%, 25.55% and 203.06% compared to raw onion, pepper and cardoon, respectively.
Revista:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN:
0021-8561
Año:
2015
Vol.:
63
N°:
17
Págs.:
4327 - 4334
Spent coffee is the main byproduct of the brewing process and a potential source of bioactive compounds, mainly phenolic acids easily extracted with water. Free and bound caffeoylquinic (3-CQA, 4-CQA, 5-CQA), dicaffeoylquinic (3,4-diCQA, 3,5-diCQA, 4,5-diCQA), caffeic, ferulic, p-coumaric, sinapic, and 4-hydroxybenzoic acids were measured by HPLC, after the application of three treatments (alkaline, acid, saline) to spent coffee extracts. Around 2-fold higher content of total phenolics has been estimated in comparison to free compounds. Phenolic compounds with one or more caffeic acid molecules were approximately 54% linked to macromolecules such as melanoidins, mainly by noncovalent interactions (up to 81% of bound phenolic compounds). The rest of the quantitated phenolic acids were mainly attached to other structures by covalent bonds (62-97% of total bound compounds). Alkaline hydrolysis and saline treatment were suitable to estimate total bound and ionically bound phenolic acids, respectively, whereas acid hydrolysis is an inadequate method to quantitate coffee phenolic acids.
Revista:
INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION
ISSN:
0963-7486
Año:
2015
Vol.:
66
N°:
6
Págs.:
657 - 664
Spent coffee grounds are a potential commercial source of substantial amounts of chlorogenic acids (CGAs). The aim of this study was to evaluate the stability of spent coffee CGAs using in vitro simulated gastroduodenal digestion and to investigate their potential absorption using an in vitro Caco-2 model of human small intestinal epithelium. During in vitro digestion, lactones were partially degraded while caffeoylquinic and feruloylquinic acids were much more stable. Transport and metabolism studies showed that 1% of the total CGAs were absorbed and transported from the apical to the basolateral side of a Caco-2 cell monolayer after 1 h. Lactones and coumaroylquinic acids showed the rate of highest absorption. Caco-2 cells possessed low metabolic activity. In conclusion, spent coffee extracts contain large amounts of CGAs, which remained bioaccessible across the intestinal barrier, albeit to a relatively low degree.
Revista:
FREE RADICAL BIOLOGY AND MEDICINE
ISSN:
0891-5849
Año:
2015
Vol.:
89
Págs.:
758 - 769
Red raspberries, containing ellagitannins and cyanidin-based anthocyanins, were fed to volunteers and metabolites appearing in plasma and urine were analysed by UHPLC-MS. Anthocyanins were not absorbed to any extent with sub nmol/L concentrations of cyanidin 3 0 glucoside and a cyanidin-O-glu-curonide appearing transiently in plasma. Anthocyanins excreted in urine corresponded to 0.007% of intake. More substantial amounts of phase II metabolites of ferulic acid and isoferulic acid, along with 4'-hydroxyhippuric acid, potentially originating from pH-mediated degradation of cyanidin in the proximal gastrointestinal tract, appeared in urine and also plasma where peak concentrations were attained 1-1.5 h after raspberry intake. Excretion of 18 anthocyanin-derived metabolites corresponded to 15.0% of intake, a figure substantially higher than obtained in other anthocyanin feeding studies. Ellagitannins pass from the small to the large intestine where the colonic microbiota mediate their conversion to urolithins A and B which appeared in plasma and were excreted almost exclusively as sulfate and glucuronide metabolites. The urolithin metabolites persisted in the circulatory system and were excreted in urine for much longer periods of time than the anthocyanin metabolites although their overall urinary recovery was lower at 7.0% of intake. It is events originating in the proximal and distal gastrointestinal tract, and subsequent phase II metabolism, that play an important role ...
Revista:
FOOD RESEARCH INTERNATIONAL
ISSN:
0963-9969
Año:
2014
Vol.:
61
Págs.:
67 - 74
Heterocyclic volatile compounds present in coffee have been proposed as potent antioxidants, but their contribution to the antioxidant capacity of coffee is still unclear and controversial. The aim of this study was to assess the actual contribution of the main volatile compounds to the overall antioxidant capacity of coffee. A total of sixty-two and sixty-four volatile compounds were identified and quantified in Arabica and Robusta coffee, respectively, by static headspace-gas chromatography-mass spectrometry (SH-GC-MS). ABTS (2,2'-Azino-bi(3-ethylbenzothiazonile-6-sulfonic acid) diammonium salt) and DPPH (2,2-Diphenyl-1-picrylhydrazyl) antioxidant activity of the most abundant volatile heterocyclic compounds (7 furans (Fu), 3 pyrroles (Py) and 2 thiophenes (Th)), aldehydes (5) and diketones (2) was evaluated in model systems at different concentrations including those found in coffee. The model system with all the heterocyclic volatiles (Fu-Py-Th) was the most active followed by pyrroles and furans. Thiophenes were ineffective as radical scavengers at all concentrations including 100-fold, and aldehydes and ketones showed negligible activities in comparison to heterocyclic volatiles. In addition, only furans exhibited linear concentration dependent ABTS antioxidant activity and individual volatile model systems showed that only 2-methyl-tetrahydrofuran-3-one and pyrrole for ABTS, and also 1-methylpyrrole for DPPH, were the main volatile compounds responsible for the coffee antioxidant activity. However, the contribution of the heterocyclic volatile compounds to the overall antioxidant capacity of a filter coffee brew was almost insignificant, even at 100-fold concentrated Fu-Py-Th model system, accounting only for up to 3.3%.
Revista:
FOOD & FUNCTION
ISSN:
2042-6496
Año:
2014
Vol.:
5
Págs.:
1718 - 1726
The effect of roasting of coffee beans and the extraction of ground coffee with different volumes of hot pressurised water on the caffeine and the total caffeoylquinic acids (CQAs) content of the resultant beverages was investigated. While caffeine was stable higher roasting temperatures resulted in a loss of CQAs so that the caffeine/CQA ratio was a good marker of the degree of roasting. The caffeine and CQA content and volume was determined for 104 espresso coffees obtained from coffee shops in Scotland, Italy and Spain, limited numbers of cappuccino coffees from commercial outlets and several instant coffees. The caffeine content ranged from 48¿317 mg per serving and CQAs from 6¿188 mg. It is evident that the ingestion of 200 mg of caffeine per day can be readily and unwittingly exceeded by regular coffee drinkers. This is the upper limit of caffeine intake from all sources recommended by US and UK health agencies for pregnant women. In view of the variable volume of serving sizes, it is also clear that the term ¿one cup of coffee¿ is not a reproducible measurement for consumption, yet it is the prevailing unit used in epidemiology to assess coffee consumption and to link the potential effects of the beverage and its components on the outcome of diseases. More accurate measurement of the intake of coffee and its potentially bioactive components are required if epidemiological studies are to produce more reliable information.
Revista:
BIOFACTORS
ISSN:
0951-6433
Año:
2013
Vol.:
39
N°:
6
Págs.:
623 - 632
Several studies have indicated potential health benefits associated with coffee consumption. These benefits might be ascribed in part to the chlorogenic acids (CGAs), the main (poly)phenols in coffee. The impact of these dietary (poly)phenols on health depends on their bioavailability. As they pass along the gastrointestinal tract, CGAs are metabolized extensively and it is their metabolites rather than the parent compounds that predominate in the circulatory system. This article reports on a study in which after incubation of espresso coffee with human fecal samples, high-performance liquid chromatography-mass spectrometry (HPLC-MS) and gas chromatography-mass spectrometry (GC-MS) were used to monitor CGA breakdown and identify and quantify the catabolites produced by the colonic microflora. The CGAs were rapidly degraded by the colonic microflora and over the 6-h incubation period, 11 catabolites were identified and quantified. The appearance of the initial degradation products, caffeic and ferulic acids, was transient, with maximum quantities at 1 h. Dihydrocaffeic acid, dihydroferulic acid, and 3-(3'-hydroxyphenyl)propionic acid were the major end products, comprising 75-83% of the total catabolites, whereas the remaining 17-25% consisted of six minor catabolites. The rate and extent of the degradation showed a clear influence of the composition of the gut microbiota of individual volunteers. Pathways involved in colonic catabolism of CGAs are proposed and comparison with studies on the bioavailability of coffee CGAs ingested by humans helped distinguish between colonic catabolites and phase II metabolites of CGAs.
Revista:
LWT-FOOD SCIENCE AND TECHNOLOGY
ISSN:
0023-6438
Año:
2013
Vol.:
51
N°:
2
Págs.:
553 - 559
The addition of sugar during roasting (torrefacto) has been proposed as a technique to increase the antioxidant capacity. However, other factors such as roasting degree and coffee origin also play a key role. Two batches of Colombian green coffee were roasted adding increased amounts of sucrose (0-15 g per 100 g of coffee) to reach the same roasting degree than a commercial Colombian coffee. Moreover, seven conventional roasted coffees from different origins (Colombia, Brazil, Kenya, Guatemala and Vietnam) and roasting degrees (Dark, Medium and Light), and one 100% Torrefacto roasted coffee were analyzed. Although the addition of sugar during roasting increased the DPPH quenching activity, phenolic compounds (5-caffeoylquinic, caffeic and ferulic acids, and 4-vinylguaiacol) were hardly affected by torrefacto roasting process, showing that Maillard and other roasting reactions products, such as browned-colored compounds including melanoidins (Abs 420 nm), have an important role as antioxidants. Principal Component Analysis (PCA) showed that roasting degree also plays a key role on overall antioxidant activity. Moreover, the Absorbance at 420 nm has been proposed as a good marker of torrefacto roasting process, whereas the roasting degree might be better characterized by L* values. (C) 2012 Elsevier Ltd. All rights reserved.
Revista:
FOOD RESEARCH INTERNATIONAL
ISSN:
0963-9969
Año:
2012
Vol.:
48
N°:
1
Págs.:
57 - 64
The aim of this work was to study the extraction behavior of the main coffee antioxidants (caffeoylquinic acids, melanoidins and caffeine) and the antioxidant capacity, during brewing time in the most widely consumed coffee brew methods (filter and espresso) in coffee. Antioxidant capacity by colorimetric assays (Folin-Ciocalteau, ABTS and DPPH) and electron spin resonance spectroscopy techniques (Fremy's salt and TEMPO) were analyzed. In espresso coffee, more than 70% of the antioxidants (except dicaffeoylquinic acids, diCQA) of a coffee brew were extracted during the first 8s. In filter coffee, a U-shape antioxidants extraction profile was observed, starting later (after 75 s) in Vietnam coffee than in Guatemala one, probably due to different wettability. Other technological parameters, such as turbulences and a longer contact time between water and ground coffee in filter coffeemaker, increased extraction efficiency, mainly in less polar antioxidant compounds as diCQA. In conclusion, these technological factors should be considered to optimize coffee antioxidants extraction that can be used as ingredients for functional foods. (C) 2012 Elsevier Ltd. All rights reserved.
