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Dipak K Das - One of the best experts on this subject based on the ideXlab platform.
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expression of the longevity proteins by both red and white wines and their cardioprotective components resveratrol Tyrosol and hydroxyTyrosol
Free Radical Biology and Medicine, 2009Co-Authors: Subhendu Mukherjee, Istva Lekli, Narasimma Gurusamy, Alberto A A Ertelli, Dipak K DasAbstract:Resveratrol increases longevity through SirT1, which is activated with NAD(+) supplied by an anti-aging enzyme PBEF. SirT1 interacts with an anti-aging transcription factor, FoxO1, which is negatively regulated by Akt. Since white wine could have similar health benefits as red wine, we determined if white wine and its cardioprotective components possess anti-aging properties by feeding rats with these compounds. The hearts expressed SirT, FoxO, and PBEF in the order of white wine>resveratrol>Tyrosol>hydroxyTyrosol>red wine, while cardioprotection shown by reduction of infarct size and cardiomyocyte apoptosis followed a different pattern: resveratrol>red wine>hydroxyTyrosol>white wine>Tyrosol, suggesting the existence of different signaling mechanisms for the induction of longevity and survival.
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does white wine qualify for french paradox comparison of the cardioprotective effects of red and white wines and their constituents resveratrol Tyrosol and hydroxyTyrosol
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Jocely I Dudley, Subhendu Mukherjee, Istva Lekli, Alberto A A Ertelli, Manika Das, Dipak K DasAbstract:It is generally believed that the French paradox is related to the consumption of red wine and not other varieties of wine, including white wine or champagne. Some recent studies have indicated that white wine could also be as cardioprotective as red wine. The present investigation compares the cardioprotective abilities of red wine, white wine, and their principal cardioprotective constituents. Different groups of rats were gavaged with red wine, white wine, resveratrol, Tyrosol, and hydroxyTyrosol. Red wine and its constituent resveratrol and white wine and its constituents Tyrosol and hydroxyTyrosol all showed different degrees of cardioprotection as evidenced by their abilities to improve postischemic ventricular performance, reduce myocardial infarct size and cardiomyocyte apoptosis, and reduce peroxide formation. It was discovered in this study that although each of the wines and their components increased the enzymatic activities of the mitochondrial complex (I-IV) and citrate synthase, which play very important roles in oxidative phosphorylation and ATP synthesis, some of the groups were more complex-specific in inducing the activity compared to the other groups. Cardioprotective ability was further confirmed by increased expression of phospho-Akt, Bcl-2, eNOS, iNOS, COX-1, COX-2, Trx-1, Trx-2, and HO-1. The results of this study suggest that white wine can provide cardioprotection similar to red wine if it is rich in Tyrosol and hydroxyTyrosol.
Na Guo - One of the best experts on this subject based on the ideXlab platform.
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the metabolism of salidroside to its aglycone p Tyrosol in rats following the administration of salidroside
PLOS ONE, 2014Co-Authors: Na Guo, Meixua Zhu, Da Sui, Yang Wang, Qia YangAbstract:Salidroside is one of the major phenolic glycosides in Rhodiola, which has been reported to possess various biological activities. In the present study the in vivo deglycosylation metabolism of salidroside was investigated and its aglycone p-Tyrosol but not the original salidroside was identified as the main form in rat tissues following the administration of salidroside. After the i.v. administration of salidroside at a dose of 50 mg/kg in rats, salidroside was quantified only in the liver, kidney and heart tissues. The highest level of p-Tyrosol was detected in the heart, followed by the spleen, kidney, liver and lungs, in order. Salidroside was detected only in the liver, in contrast, p-Tyrosol was detectable in most tissues except the brain, and the kidney tissues contained a significant amount of p-Tyrosol compared to the other tissues after the i.g. administration of 100 mg/kg salidroside. The excretion behaviour revealed that the administrated salidroside mainly eliminated in the form of salidroside but not its aglycone metabolite p-Tyrosol through urine. After i.v. and i.g. administration in rats, 64.00% and 23.80% of the total dose was excreted through urine in the form of salidroside, respectively. In addition, 0.19% and 2.25% of the dose was excreted in the form of p-Tyrosol through urine after i.v. and i.g. administration, respectively. The faecal salidroside and p-Tyrosol concentrations were 0.3% and 1.48% of the total dose after i.v. administration, respectively. After the i.g. administration of salidroside, trace salidroside and p-Tyrosol were quantified in faeces within 72 h. In addition, the biliary excretion levels of salidroside after i.v. and i.g. administration were 2.86% and 0.02% of the dose, respectively. The obtained results show that salidroside was extensively metabolised to its aglycone p-Tyrosol and distributed to various organs and the orginal salidroside was cleared rapidly through urine following the administration of salidroside.
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simultaneous determination of salidroside and its aglycone metabolite p Tyrosol in rat plasma by liquid chromatography tandem mass spectrometry
Molecules, 2012Co-Authors: Na Guo, Jia Zheng, Dehui Zhang, Yang WangAbstract:Salidroside and its aglycone p-Tyrosol are two major phenols in the genus Rhodiola and have been confirmed to possess various pharmacological properties. In our present study, p-Tyrosol was identified as the deglycosylation metabolite of salidroside after intravenous (i.v.) administration to rats at a dose of 50 mg/kg, but was not detectable after intragastric gavage (i.g.) administration through HPLC-photodiode array detection (PDA) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis. Next, an accurate and precise LC-MS/MS method was developed to quantitatively determine salidroside and p-Tyrosol in rat plasma samples. Samples were analyzed by LC-MS/MS on a reverse-phase xTerra MS C18 column which was equilibrated and eluted with an isocratic mixture of acetonitrile-water (1:9, v/v) at a flow rate of 0.3 mL/min. The analytes were monitored by multiple reaction monitoring (MRM) under the negative electrospray ionization mode. The precursor/product transitions (m/z) were 299.0→118.8 for salidroside, 137.0→118.9 for p-Tyrosol and 150.1→106.9 for the internal standard (IS), paracetamol, respectively. The calibration curve was linear over the concentration ranges of 50–2,000 ng/mL for salidroside and 20–200 ng/mL for p-Tyrosol. The inter- and intra-day accuracy and precision were within ±15%. The method has been successfully applied to the pharmacokinetic study and the oral bioavailability was calculated.
Yang Wang - One of the best experts on this subject based on the ideXlab platform.
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the metabolism of salidroside to its aglycone p Tyrosol in rats following the administration of salidroside
PLOS ONE, 2014Co-Authors: Na Guo, Meixua Zhu, Da Sui, Yang Wang, Qia YangAbstract:Salidroside is one of the major phenolic glycosides in Rhodiola, which has been reported to possess various biological activities. In the present study the in vivo deglycosylation metabolism of salidroside was investigated and its aglycone p-Tyrosol but not the original salidroside was identified as the main form in rat tissues following the administration of salidroside. After the i.v. administration of salidroside at a dose of 50 mg/kg in rats, salidroside was quantified only in the liver, kidney and heart tissues. The highest level of p-Tyrosol was detected in the heart, followed by the spleen, kidney, liver and lungs, in order. Salidroside was detected only in the liver, in contrast, p-Tyrosol was detectable in most tissues except the brain, and the kidney tissues contained a significant amount of p-Tyrosol compared to the other tissues after the i.g. administration of 100 mg/kg salidroside. The excretion behaviour revealed that the administrated salidroside mainly eliminated in the form of salidroside but not its aglycone metabolite p-Tyrosol through urine. After i.v. and i.g. administration in rats, 64.00% and 23.80% of the total dose was excreted through urine in the form of salidroside, respectively. In addition, 0.19% and 2.25% of the dose was excreted in the form of p-Tyrosol through urine after i.v. and i.g. administration, respectively. The faecal salidroside and p-Tyrosol concentrations were 0.3% and 1.48% of the total dose after i.v. administration, respectively. After the i.g. administration of salidroside, trace salidroside and p-Tyrosol were quantified in faeces within 72 h. In addition, the biliary excretion levels of salidroside after i.v. and i.g. administration were 2.86% and 0.02% of the dose, respectively. The obtained results show that salidroside was extensively metabolised to its aglycone p-Tyrosol and distributed to various organs and the orginal salidroside was cleared rapidly through urine following the administration of salidroside.
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simultaneous determination of salidroside and its aglycone metabolite p Tyrosol in rat plasma by liquid chromatography tandem mass spectrometry
Molecules, 2012Co-Authors: Na Guo, Jia Zheng, Dehui Zhang, Yang WangAbstract:Salidroside and its aglycone p-Tyrosol are two major phenols in the genus Rhodiola and have been confirmed to possess various pharmacological properties. In our present study, p-Tyrosol was identified as the deglycosylation metabolite of salidroside after intravenous (i.v.) administration to rats at a dose of 50 mg/kg, but was not detectable after intragastric gavage (i.g.) administration through HPLC-photodiode array detection (PDA) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis. Next, an accurate and precise LC-MS/MS method was developed to quantitatively determine salidroside and p-Tyrosol in rat plasma samples. Samples were analyzed by LC-MS/MS on a reverse-phase xTerra MS C18 column which was equilibrated and eluted with an isocratic mixture of acetonitrile-water (1:9, v/v) at a flow rate of 0.3 mL/min. The analytes were monitored by multiple reaction monitoring (MRM) under the negative electrospray ionization mode. The precursor/product transitions (m/z) were 299.0→118.8 for salidroside, 137.0→118.9 for p-Tyrosol and 150.1→106.9 for the internal standard (IS), paracetamol, respectively. The calibration curve was linear over the concentration ranges of 50–2,000 ng/mL for salidroside and 20–200 ng/mL for p-Tyrosol. The inter- and intra-day accuracy and precision were within ±15%. The method has been successfully applied to the pharmacokinetic study and the oral bioavailability was calculated.
Rafael De La Torre - One of the best experts on this subject based on the ideXlab platform.
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cyp2d6 and cyp2a6 biotransform dietary Tyrosol into hydroxyTyrosol
Food Chemistry, 2017Co-Authors: Jose Rodriguezmorato, Patricia Robledo, Julieanne Tanne, Anna Orona, Clara Perezmana, C Olive Y Che, Rachel F Tyndale, Rafael De La TorreAbstract:The dietary phenol Tyrosol has been reported to be endogenously transformed into hydroxyTyrosol, a potent antioxidant with multiple health benefits. In this work, we evaluated whether tyrosine hydroxylase (TH) and cytochrome P450s (CYPs) catalyzed this process. To assess TH involvement, Wistar rats were treated with α-methyl-L-tyrosine and Tyrosol. Tyrosol was converted into hydroxyTyrosol whilst α-methyl-L-tyrosine did not inhibit the biotransformation. The role of CYP was assessed in human liver microsomes (HLM) and Tyrosol-to-hydroxyTyrosol conversion was observed. Screening with selective enzymatic CYP inhibitors identified CYP2A6 as the major isoform involved in this process. Studies with baculosomes further demonstrated that CYP2D6 and CYP3A4 could transform Tyrosol into hydroxyTyrosol. Experiments using human genotyped livers showed an interindividual variability in hydroxyTyrosol formation and supported findings that CYP2D6 and CYP2A6 mediated this reaction. The dietary health benefits of Tyrosol-containing foods remain to be evaluated in light of CYP pharmacogenetics.
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biocatalyzed synthesis and structural characterization of monoglucuronides of hydroxyTyrosol Tyrosol homovanillic alcohol and 3 4 hydroxyphenyl propanol
Advanced Synthesis & Catalysis, 2006Co-Authors: Olha Khymenets, Mariaisabel Covas, Jesus Jogla, Pere Clapes, Teodo Parella, Rafael De La TorreAbstract:The biocatalytic synthesis and purification of O-β-D-monoglucuronide conjugates of hydroxyTyrosol, Tyrosol, homovanillic alcohol, and 3-(4′-hydroxyphenyl)propanol, using porcine liver microsomes, are described here. The glucuronides were synthesized, analyzed and separated by HPLC-UV, identified by HPLC-MS, and their structures unequivocally established by NMR techniques. The outcome of the glucuronidation reaction depends on the structure of the phenolic compounds. Thus, the glucuronidation of hydroxyTyrosol, biocatalyzed with porcine liver microsomes, proceeded exclusively on the phenolic hydroxy groups. The regioselectivity was similar to that observed for human and rat liver microsomes, the 4′-hydroxy position being more favorable than the 3′-hydroxy one. In the case of Tyrosol, homovanillic alcohol, and hydroxyphenylpropanol, two products were formed during microsomal glucuronidation: a major one, the phenolic O-β-D-glucuronidated derivative and, a minor one, the O-β-D-glucuronidated aliphatic alcohol.
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capillary gas chromatography mass spectrometry quantitative determination of hydroxyTyrosol and Tyrosol in human urine after olive oil intake
Analytical Biochemistry, 2001Co-Authors: Elisabe Mirocasas, Magi Farre Albaladejo, Mariaisabel Covas, Jordi Ortuno Rodriguez, Ester Menoyo Colome, Rosa Lamuela M Raventos, Rafael De La TorreAbstract:Abstract Recent in vitro studies have demonstrated antioxidant properties of some virgin olive oil phenolic compounds. One of the prerequisites to extrapolate these data to an in vivo situation is the knowledge of their bioavailability in humans. In the present work we describe an analytical method which enables us to perform hydroxyTyrosol and Tyrosol quantitative determinations in human urine. This method was successfully used in bioavailability studies of both phenolic compounds after acute olive oil administration. Virgin olive oil was administered to healthy volunteers after a low phenolic diet. The dose administered of both phenolic compounds was estimated in reference to free forms of hydroxyTyrosol and Tyrosol present in virgin olive oil extracts before and after being submitted to hydrolytic conditions. These conditions mimic those occurring during digestion. Urine samples were collected before and after acute olive oil intake and analyzed by capillary gas chromatography–mass spectrometry. HydroxyTyrosol and Tyrosol urinary recovery increased in response to olive oil administration, obtaining maximal values in the first 4 h. Our results further indicate that hydroxyTyrosol and Tyrosol are mainly excreted in conjugated form, since only 5.9 ± 1.4% (hydroxyTyrosol) and 13.8 ± 5.4% (Tyrosol) of the total amounts excreted in urine were in free form.
Elisabe Mirocasas - One of the best experts on this subject based on the ideXlab platform.
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bioavailability of Tyrosol an antioxidant phenolic compound present in wine and olive oil in humans
Drugs Under Experimental and Clinical Research, 2003Co-Authors: M I Covas, Elisabe Mirocasas, Montse Fito, M Farrealbadalejo, Eva Gimeno, J Marruga, R De La TorreAbstract:Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of Tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intima in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. Thus, phenolics, which are able to bind LDL, could be effective in preventing lipid peroxidation and atherosclerotic processes. The ability of Tyrosol to bind human LDL has been reported. We have demonstrated the bioavailability of Tyrosol in humans from virgin olive oil in its natural form. Urinary Tyrosol increased, reaching a peak at 0-4 h after virgin olive oil administration. Men and women showed a different pattern of urinary excretion of Tyrosol. Moreover, Tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. In summary, our results suggest that Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed in in vivo studies.
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Tyrosol and hydroxyTyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans
European Journal of Clinical Nutrition, 2003Co-Authors: Elisabe Mirocasas, M I Covas, Montse Fito, M Farrealbadalejo, J Marruga, R De La TorreAbstract:Objective: To investigate the absorption of Tyrosol and hydroxyTyrosol from moderate and sustained doses of virgin olive oil consumption. The study also aimed to investigate whether these phenolic compounds could be used as biomarkers of virgin olive oil intake. Design and interventions: Ingestion of a single dose of virgin olive oil (50 ml). Thereafter, for a week, participants followed their usual diet which included 25 ml/day of the same virgin olive oil as the source of raw fat. Setting: Unitat de Recerca en Farmacologia. Institut Municipal d'Investigacio Medica (IMIM). Subjects: Seven healthy volunteers. Results: An increase in 24 h urine of Tyrosol and hydroxyTyrosol, after both a single-dose ingestion (50 ml) and short-term consumption (one week, 25 ml/day) of virgin olive oil (P<0.05) was observed. Urinary recoveries for Tyrosol were similar after a single dose and after sustained doses of virgin olive oil. Mean recovery values for hydroxyTyrosol after sustained doses were 1.5-fold those obtained after a single 50 ml dose. Conclusion: Tyrosol and hydroxyTyrosol are absorbed from realistic doses of virgin olive oil. With regard to the dose–effect relationship, 24 h urinary Tyrosol seems to be a better biomarker of sustained and moderate doses of virgin olive oil consumption than hydroxyTyrosol. Sponsorship: This work was supported by grants ALI97-1607-CO2-01 from CICYT, 98/9562 FPI from FIS and by Federacio de Cooperatives Agraries de Catalunya.
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capillary gas chromatography mass spectrometry quantitative determination of hydroxyTyrosol and Tyrosol in human urine after olive oil intake
Analytical Biochemistry, 2001Co-Authors: Elisabe Mirocasas, Magi Farre Albaladejo, Mariaisabel Covas, Jordi Ortuno Rodriguez, Ester Menoyo Colome, Rosa Lamuela M Raventos, Rafael De La TorreAbstract:Abstract Recent in vitro studies have demonstrated antioxidant properties of some virgin olive oil phenolic compounds. One of the prerequisites to extrapolate these data to an in vivo situation is the knowledge of their bioavailability in humans. In the present work we describe an analytical method which enables us to perform hydroxyTyrosol and Tyrosol quantitative determinations in human urine. This method was successfully used in bioavailability studies of both phenolic compounds after acute olive oil administration. Virgin olive oil was administered to healthy volunteers after a low phenolic diet. The dose administered of both phenolic compounds was estimated in reference to free forms of hydroxyTyrosol and Tyrosol present in virgin olive oil extracts before and after being submitted to hydrolytic conditions. These conditions mimic those occurring during digestion. Urine samples were collected before and after acute olive oil intake and analyzed by capillary gas chromatography–mass spectrometry. HydroxyTyrosol and Tyrosol urinary recovery increased in response to olive oil administration, obtaining maximal values in the first 4 h. Our results further indicate that hydroxyTyrosol and Tyrosol are mainly excreted in conjugated form, since only 5.9 ± 1.4% (hydroxyTyrosol) and 13.8 ± 5.4% (Tyrosol) of the total amounts excreted in urine were in free form.
