Nanoparticles (NPs) recently emerged as new chemical elicitors acting as signaling agents affecting several processes in plant metabolism. The aim of this work was to investigate the impact of the ...addition of copper oxide (CuO), zinc oxide (ZnO) and iron oxide (Fe
O
) NPs (<100 nm) at different concentrations (1, 5 and 10 mg/L) to the culture media on several morphological, physiological and -biochemical parameters of in vitro shoot cultures of
L'Hér and
G. López and R. Morales (Lamiaceae), as well as on phenolic profile and bioactivity (antioxidant and enzyme inhibition capacities). Although some decreases in shoot number and length were observed in response to NPs, biomass production was not affected or was improved in both species. Most NPs treatments decreased total chlorophyll and carotenoid contents and increased malondialdehyde levels, an indicator of lipid peroxidation, in both species. HPLC-HR-MS analysis led to the identification of thirteen and twelve phenolic compounds, respectively, in
and
extracts, being rosmarinic acid the major compound found in all the extracts. ZnO and Fe
O
NPs induced an increase in total phenolic and rosmarinic acid contents in
extracts. Additionally, some NPs treatments also increased antioxidant activity in extracts from this species and the opposite was observed for
. The capacity of the extracts to inhibit tyrosinase, acetylcholinesterase and butyrylcholinesterase enzymes was not considerably affected. Overall, NPs had a significant impact on different parameters of
and
in vitro shoot cultures, although the results varied with the species and NPs type.
SCOPE: Hesperetin‐7‐O‐rutinoside (hesperidin) reduces blood pressure in healthy volunteers but its intestinal absorption and metabolism are not fully understood. Therefore, we aimed to determine ...sites of absorption and metabolism of dietary flavanone glycosides in humans. METHODS AND RESULTS: Using a single‐blind, randomized crossover design, we perfused equimolar amounts of hesperetin‐7‐O‐rutinoside and hesperetin‐7‐O‐glucoside directly into the proximal jejunum of healthy volunteers. We assessed the appearance of metabolites in the perfusate, blood and urine, to determine the sites of metabolism and excretion, and compared this to oral administration. The glucoside was rapidly hydrolyzed by brush border enzymes without any contribution from pancreatic, stomach, or other secreted enzymes, or from bacterial enzymes. Only ∼3% of the dose was recovered intact in the perfusate, indicating high absorption. A proportion was effluxed directly back into the perfused segment mainly in the form of hesperetin‐3′‐O‐sulfate. In contrast, very little hydrolysis or absorption of hesperetin‐7‐O‐rutinoside was observed with ∼80% recovered in the perfusate, no hesperetin metabolites were detected in blood and only traces were excreted in urine. CONCLUSION: The data elucidate the pathways of metabolism of dietary hesperidin in vivo and will facilitate better design of mechanistic studies both in vivo and in vitro.
This review considers recent investigations on the bioavailability of anthocyanins and flavanones. Both flavonoids are significant dietary components and are considered to be poorly bioavailable, as ...only low levels of phase II metabolites appear in the circulatory system and are excreted in urine. However, when lower molecular weight phenolic and aromatic ring-fission catabolites, produced primarily by the action of the colonic microbiota, are taken into account, it is evident that anthocyanins and flavanones are much more bioavailable than previously envisaged. The metabolic events to which these flavonoids are subjected as they pass along the gastrointestinal tract and are absorbed into the circulatory system prior to their rapid elimination by renal excretion are highlighted. Studies on the impact of other food components and the probiotic intake on flavonoid bioavailability are summarized, as is the bioactivity of metabolites and catabolites assayed using a variety of in vitro model systems.
Scope
β‐Cryptoxanthin is an abundant carotenoid in fruits and vegetables that can be quantified in human blood serum. Yet, contrary to other carotenoids, its effects on endothelial cells and ...angiogenesis remain unknown.
Methods and results
Human umbilical vein endothelial cells (HUVEC) are treated with 0.01, 0.1, or 1 μm of β‐cryptoxanthin. Antioxidant activity is determined by its free radical scavenging and oxygen‐radical absorbance capacity. The effect on migration and formation of tubular structures is studied. Additionally, effect on angiogenesis is also analyzed using an in vivo model. β‐Cryptoxanthin exhibits scavenging ability, having an antioxidant effect on HUVEC. Interestingly, β‐cryptoxanthin reduces their migration and angiogenesis, even in the presence of vascular endothelial growth factor (VEGF). Additionally, such carotenoid inhibits in vivo angiogenesis induced by VEGF. In addition, treatment of HUVEC with LE540 (retinoic acid receptor RAR panantagonist) inhibits β‐cryptoxanthin antiangiogenic effect on HUVEC.
Conclusion
β‐Cryptoxanthin inhibits angiogenesis through RAR. Thus, this carotenoid and food containing it may be useful for the prevention and treatment of angiogenic pathologies. That includes tumoral growth and wet macular degeneration associated with aging. To the best of our knowledge, this is the first report of the antioxidant effect and antiangiogenic activity of this carotenoid on HUVEC, both in vitro and in vivo.
Currently, little is known about the effect of β‐cryptoxanthin, an abundant carotenoid in fruits and vegetables, on angiogenesis. Interestingly, it is shown in this study that this compound acts as an antioxidant. Thus, it exhibits scavenging ability, decreasing reactive oxygen species levels in human umbilical vein endothelial cells. In these cells, it also reduces migration and angiogenesis, even in the presence of vascular endothelial growth factor (VEGF). Besides, in vivo angiogenesis induced by VEGF was inhibited by β‐cryptoxanthin. In part, this inhibitory effect is mediated by its interaction with retinoic acid receptor. Therefore, it may be useful for prevention and treatment of different pathologies, like the ones related to oxidative stress and angiogenesis, such as cancer.
Data obtained with in vitro fecal incubations and a feeding study indicate black tea theaflavin and its galloyl derivatives are not absorbed in detectable amounts in either the upper or lower ...gastrointestinal tract. The theaflavin skeleton is comparatively resistant to degradation by colonic bacteria with a 67% recovery being obtained after a 24 h incubation, which yielded 21 phenolic and aromatic catabolites. The theaflavin galloyl moiety was removed by the microbiota, and the released gallic acid further transformed to 3-O- and 4-O-methyl gallic acids, pyrogallol-1-sulfate and pyrogallol-2-sulfate, which were excreted in urine in amounts equivalent to 94% of intake. The main urinary product potentially derived from breakdown of the theaflavin skeleton was 3-(4′-hydroxyphenyl)propionic acid. A number of the colonic catabolites originating from gallic acid and theaflavins has been reported to be bioactive in ex vivo and in vitro models with a variety of potential modes of action.
•We measure antioxidant capacity and phenolics of vegetables after frying or griddling.•Heat treatments increased the concentration of phenolic compounds in vegetables.•The thermal destruction of ...cell walls and compartments release phenolic compounds.•Increment in phenolics after cooking correlates with higher antioxidant capacity.•Griddled vegetables showed the highest amounts of phenolic compounds.
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.
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 μmol 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 metabolitescomprising di-O-glucuronide, O-glucuronide, O-glucuronyl-sulfate, and sulfate derivatives of hesperetin, naringenin, and eriodictyoland 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.
Physical exercise has been reported to increase the bioavailability of citrus flavanones.
We investigated the bioavailability of orange juice (OJ) (poly)phenols in endurance-trained males before and ...after cessation of training for 7 d.
Ten fit, endurance-trained males, with a mean ± SD maximal oxygen consumption of 58.2 ± 5.3 mL · kg−1 · min−1, followed a low (poly)phenol diet for 2 d before drinking 500 mL of OJ containing 398 μmol of (poly)phenols, of which 330 μmol 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.
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, urinary excretion of 3 colonic catabolites of bacterial origin, most notably, 3-(3′-hydroxy-4′-methoxyphenyl)hydracrylic acid, did increase significantly when OJ was consumed postcessation compared with precessation of training. Data were also obtained on interindividual variations in flavanone bioavailability.
A 7-d cessation of endurance training enhanced, rather than reduced, the bioavailability of OJ flavanones. The biological significance of these differences and whether they extend to the bioavailability of other dietary (poly)phenols remain to be determined. Hesperetin-3′-O-glucuronide and the colonic microbiota-derived catabolite 3-(3′-hydroxy-4′-methoxyphenyl)hydracrylic acid are key biomarkers of the consumption of hesperetin-O-glycoside–containing OJ and other citrus products. This trial was registered at clinicaltrials.gov as NCT02627547.
SCOPE: The role of colonic microbiota in the breakdown of hesperetin, naringenin, and ferulic acid, compounds found as glycosides in orange juice, was investigated using an in vitro fermentation ...model. METHODS AND RESULTS: Test compounds were incubated with human fecal slurries cultured under anaerobic conditions, and the production of phenolic acid catabolites were monitored by GC‐MS and HPLC‐MS². Hesperetin was converted to 3‐(3′‐hydroxy‐4′‐methoxyphenyl)propionic acid, 3‐(3′,4′‐dihydroxyphenyl)propionic acid, and 3‐(3′‐hydroxyphenyl)propionic acid while 3‐(phenyl)propionic acid was the major end product derived from naringenin. The data obtained are compared to our previously published data on urinary excretion of phenolic and aromatic acids after acute orange juice consumption (Pereira‐Caro et al. Am. J. Clin. Nutr. 2014, 100, 1385–1391). Catabolism pathways are proposed for events occurring in the colon and those taking place postabsorption into the circulatory system with particular reference to the excretion of 3‐(3′‐hydroxy‐4′‐methoxyphenyl)hydracrylic acid, which is not formed in fecal incubations. Ferulic acid was also degraded by the colonic microflora being converted principally to 3‐(3′‐methoxy‐4′‐hydroxyphenyl)propionic acid, a phenolic acid that appears in urine after orange juice consumption. CONCLUSION: The study provides novel information on the potential involvement of the colonic microbiota in the overall bioavailability of orange juice (poly)phenols through the production of phenylpropionic acids and subsequent hepatic conversions that lead to hippuric acid and its hydroxylated analogues.
This study aims to investigate whether heat treatment applied to cactus cladodes influences the bioaccessibility of their (poly)phenolic compounds after simulated gastric and intestinal digestion. A ...total of 45 (poly)phenols were identified and quantified in raw and cooked cactus cladodes by ultra high performance liquid chromatography photodiode array detector high resolution mass spectrometry. Both flavonoids (60–68% total), mainly isorhamnetin derivatives, and phenolic acids (32–40%) with eucomic acids as the predominant ones significantly (p < 0.05) increased with microwaving and griddling processes. After in vitro gastrointestinal digestion, 55–64% of the total (poly)phenols of cooked cactus cladodes remained bioaccessible versus 44% in raw samples. Furthermore, digestive conditions and enzymes degraded or retained more flavonoids (37–63% bioaccessibility) than phenolic acids (56–87% bioaccessibility). Microwaved cactus cladodes contributed the highest amount of (poy)phenols (143.54 mg/g dm) after gastrointestinal process, followed by griddled samples (133.98 mg/g dm), showing the highest antioxidant capacity. Additionally, gastrointestinal digestion induced isomerizations among the three stereoisomeric forms of piscidic and eucomic acids.
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