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Peter C H Hollman - One of the best experts on this subject based on the ideXlab platform.
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the type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary Quercetin Glycosides
British Journal of Nutrition, 2004Co-Authors: Ilja C W Arts, Aloys L A Sesink, Maria Faassenpeters, Peter C H HollmanAbstract:Quercetin is an important dietary flavonoid with putative beneficial effects in the prevention of cancer and CVD. The in vivo bioactivity of Quercetin depends on its bioavailability, which varies widely between foods. We used an in situ rat intestinal perfusion model to study whether differential small intestinal hydrolysis of the sugar moiety of five naturally occurring Quercetin Glycosides determines the small intestinal uptake and subsequent biliary excretion of Quercetin. After 30 min perfusion, a decrease of intact Quercetin glycoside in perfusate was observed for Quercetin-3-O-s-glucoside (20·9 (SEM 1·4) mmol/l) and Quercetin-4 0 -O-s-glucoside (23·5 (SEM 1·6) mmol/ l), but not of Quercetin-3-O-s-galactoside, Quercetin-3-O-s-rhamnoside and Quercetin-3-O-a-arabinopyranoside. Appearance of free Quercetin in perfusate and conjugated Quercetin metabolites (Quercetin, isorhamnetin, and tamarixetin) in portal and peripheral plasma and bile were also significantly greater after treatment with Quercetin-3-O-s-glucoside or Quercetin-4 0 -O-s-glucoside compared with any of the other Glycosides. Thus, the type of sugar moiety is a major determinant of the small intestinal absorption of Quercetin Glycosides, but the position (3 or 4 0 ) of the glucose moiety does not further influence absorption. The poor bioavailability of important dietary Quercetin Glycosides has implications for their in vivo bioactivities. Flavonoid: Quercetin glycoside: Intestinal absorption: Lactase phlorizin hydrolase: Bile
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the type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary Quercetin Glycosides
British Journal of Nutrition, 2004Co-Authors: Ilja C W Arts, Aloys L A Sesink, Maria Faassenpeters, Peter C H HollmanAbstract:Quercetin is an important dietary flavonoid with putative beneficial effects in the prevention of cancer and CVD. The in vivo bioactivity of Quercetin depends on its bioavailability, which varies widely between foods. We used an in situ rat intestinal perfusion model to study whether differential small intestinal hydrolysis of the sugar moiety of five naturally occurring Quercetin Glycosides determines the small intestinal uptake and subsequent biliary excretion of Quercetin. After 30 min perfusion, a decrease of intact Quercetin glycoside in perfusate was observed for Quercetin-3-O-ss-glucoside (20.9 (sem 1.4) micromol/l) and Quercetin-4'-O-ss-glucoside (23.5 (sem 1.6) micromol/l), but not of Quercetin-3-O-ss-galactoside, Quercetin-3-O-ss-rhamnoside and Quercetin-3-O-alpha-arabinopyranoside. Appearance of free Quercetin in perfusate and conjugated Quercetin metabolites (Quercetin, isorhamnetin, and tamarixetin) in portal and peripheral plasma and bile were also significantly greater after treatment with Quercetin-3-O-ss-glucoside or Quercetin-4'-O-ss-glucoside compared with any of the other Glycosides. Thus, the type of sugar moiety is a major determinant of the small intestinal absorption of Quercetin Glycosides, but the position (3 or 4') of the glucose moiety does not further influence absorption. The poor bioavailability of important dietary Quercetin Glycosides has implications for their in vivo bioactivities.
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flavonols flavones and flavanols nature occurrence and dietary burden
Journal of the Science of Food and Agriculture, 2000Co-Authors: Peter C H Hollman, Ilja C W ArtsAbstract:Total flavonol and flavone contents of foods have been determined with validated state-of-the-art methods. Quercetin dominates, and flavonol levels found in vegetables and fruits are below 10 mg kg−1. However, high concentrations are found in onions (300 mg kg−1), kale (450 mg kg−1), broccoli (100 mg kg−1), beans (50 mg kg−1), apples (50 mg kg−1), blackcurrants (40 mg kg−1), and tea (30 mg l−1). The dietary intake of flavonols varies 10-fold between countries (6–60 mg day−1). Flavones are of minor importance in the diet. Tea, wine and fruits are the most important sources of flavanols, but there are gaps in our knowledge on flavanol levels of many foods. The absorption of dietary Quercetin Glycosides in humans ranges from 20 to 50%. The sugar moiety is an important determinant of the bioavailability of flavonols. The presence of a glucose moiety significantly enhances absorption. The extent of absorption of flavanols in humans seems similar to that of flavonols but has been little studied. Flavonols and flavanols are extensively metabolised, as only 1–2% of them are excreted with an intact flavonoid backbone. Hepatic biotransformations include glucuronidation and sulphatation of the phenolic hydroxyls and O-methylation of catechol groups. Bacteria of the colon cleave the C-ring of the flavonoid nucleus to phenolic acids which are subsequently absorbed. Apart from conjugates, virtually no metabolites have been characterised in humans. Absorption of flavanols is rather fast, with times to reach peak values between 0.5 and 4 h. Flavanols are rapidly excreted, with elimination half-lives of 1–6 h. Quercetin Glycosides show rapid to slow absorption; peak values are reached between < 0.5 and 9 h. The type of glycoside determines the rate of absorption. Excretion of Quercetin Glycosides is slow: elimination half-lives are 24 h, independent of the type of glycoside. Analytical data for flavanols in foods are needed. Tea, as an important dietary source, has to be studied. Research on the bioavailability of flavonols and flavanols has to be expanded. Attention is needed for the identification and quantification of their metabolites in body fluids. © 2000 Society of Chemical Industry
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Absorption of dietary Quercetin Glycosides and Quercetin in healthy ileostomy volunteers
American Journal of Clinical Nutrition, 1995Co-Authors: Peter C H Hollman, Sonja D. Van Leeuwen, Marcel J.b. Mengelers, Jeanne H M De Vries, Martijn B. KatanAbstract:Quercetin is a dietary antioxidant that prevents oxidation of low-density lipoproteins in vitro. Intake of Quercetin was inversely associated with coronary heart disease mortality in elderly Dutch men. However, the extent of absorption of Quercetin in humans is unclear. The aim of this study was to quantify absorption of various forms of Quercetin. Nine healthy ileostomy subjects were studied, to avoid losses caused by colonic bacteria. They followed a Quercetin-free diet for 12 d; on days 4, 8, and 12 they received a supplement of fried onions at breakfast (rich in Quercetin glucosides) equivalent to 89 mg aglycone, pure Quercetin rutinoside (the major Quercetin compound in tea) equivalent to 100 mg aglycone, or 100 mg pure Quercetin aglycone, in random order. Subsequently, participants collected ileostomy effluent and urine for 13 h. In vitro incubations of Quercetin or its Glycosides with gastrointestinal fluids showed minimal degradation. Absorption of Quercetin, defined as oral intake minus ileostomy excretion and corrected for 14% degradation within the ileostomy bag, was 52 +/- 15% for Quercetin glucosides from onions, 17 +/- 15% for Quercetin rutinoside, and 24 +/- 9% for Quercetin aglycone. Mean excretion of Quercetin or its conjugates in urine was 0.5% of the amount absorbed; Quercetin excretion in urine was negatively correlated with excretion in ileostomy effluent (r = -0.78, n = 27). We conclude that humans absorb appreciable amounts of Quercetin and that absorption is enhanced by conjugation with glucose.
Hiroshi Hara - One of the best experts on this subject based on the ideXlab platform.
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Melibiose, a Nondigestible Disaccharide, Promotes Absorption of Quercetin Glycosides in Rat Small Intestine
Journal of agricultural and food chemistry, 2016Co-Authors: Seiya Tanaka, Aki Shinoki, Hiroshi HaraAbstract:We demonstrated that melibiose, a nondigestible disaccharide composed of galactose and glucose with α-1,6 glycoside linkage, promotes the absorption of water-soluble Quercetin Glycosides in ligated small intestinal loop of anesthetized rats. Water-soluble Quercetin glycoside, a Quercetin-3-O-glucoside mixture (Q3GM), includes Quercetin-3-O-glucoside (Q3G, 31.9%), mono (21.2%) and di (17.1%), glucose adducts with α-1,4 linkages. After instillation of Q3GM into the intestinal loop with or without melibiose, the plasma concentration of Quercetin derivatives in the portal blood was considerably higher in the melibiose group at 60 min. Furthermore, we evaluated the hydrolytic rate of Q3G by the mucosal homogenate of the small intestine with six different disaccharides. Melibiose and isomaltose, which have α-1,6 glycoside linkage, were found to promote Q3G hydrolysis to aglycone. These results suggest that melibiose promotes Quercetin glycoside absorption in rats by increasing glycoside hydrolysis in the intest...
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melibiose a non digestible saccharide promotes absorption of Quercetin Glycosides in rat small intestine with a novel mechanism 1044 9
The FASEB Journal, 2014Co-Authors: Seiya Tanaka, Aki Shinoki, Hiroshi HaraAbstract:We examined effects of melibiose a non-digestible saccharide, on intestinal absorption of Quercetin Glycosides, which are low bioavailability but have antioxidant, anti-inflammatory and anti-carcin...
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high biliary excretion levels of Quercetin metabolites after administration of a Quercetin glycoside in conscious bile duct cannulated rats
Bioscience Biotechnology and Biochemistry, 2009Co-Authors: Noriko Matsukawa, Megumi Matsumoto, Hiroshi HaraAbstract:Biliary excretion of Quercetin metabolites in conscious rats was biphasic, a high peak within 3 h and a lower peak for next 6 h, after duodenal administration of soluble Quercetin Glycosides. We also found much higher biliary excretion of Quercetin metabolites than urinary excretion on feeding a Quercetin glycoside diet. These results suggest high levels of enterohepatic circulation of Quercetin metabolites.
Andreas Schieber - One of the best experts on this subject based on the ideXlab platform.
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characterization of phenolic acids and flavonoids in dandelion taraxacum officinale web ex wigg root and herb by high performance liquid chromatography electrospray ionization mass spectrometry
Rapid Communications in Mass Spectrometry, 2005Co-Authors: Katrin Schutz, Reinhold Carle, Dietmar R Kammerer, Andreas SchieberAbstract:Phenolic acids and flavonoids were extracted from a dandelion (Taraxacum officinale WEB. ex WIGG.) root and herb juice and characterized by high-performance liquid chromatography/electrospray ionization mass spectrometry. Among the 43 compounds detected, 5 mono- and dicaffeoylquinic acids, 5 tartaric acid derivatives, 8 flavone and 8 flavonol Glycosides were characterized based on their UV spectra and their fragmentation patterns in collision-induced dissociation experiments. The predominant compound was chicoric acid (dicaffeoyltartaric acid). Furthermore, several caffeoylquinic acid isomers were distinguished in dandelion extracts for the first time by their specific mass spectral data. The present study reveals that even more Quercetin Glycosides were found in dandelion than hitherto assumed. The occurrence of di- and triglycosylated flavonoids in particular has not yet been described. This paper marks the first report on HPLC-DAD/ESI-MSn investigations of phenolic compounds in dandelion.
Baoru Yang - One of the best experts on this subject based on the ideXlab platform.
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sephadex lh 20 fractionation and bioactivities of phenolic compounds from extracts of finnish berry plants
Food Research International, 2018Co-Authors: Ye Tian, Jaana Liimatainen, Anna Puganen, Hanna Leena Alakomi, Jari Sinkkonen, Baoru YangAbstract:Abstract In order to assist developing a natural, safe food-preservative, aqueous ethanolic extracts of leaves and berries of eight Finnish berry plants were fractionated with Sephadex LH-20 column chromatography. For each fraction, phenolic compounds were analyzed with NMR, UPLC-DAD-ESI-MS and HPLC-DAD. The antioxidant activities of the fractions were investigated using oxygen radical absorbance capacity (ORAC) assay, and the antibacterial activities were evaluated against foodborne pathogens Staphylococcus aureus and Escherichia coli. Antioxidant activities of the fractions correlated highly with both the total concentration and structural feature of phenolic compounds, including both flavonoids and non-flavonoid phenolics. ORAC value correlated strongly with the concentration of (+)-catechin, (−)-epicatecin, Quercetin Glycosides, and anthocyanins. Increase in size and number of sugar moieties may reduce the antioxidative activities of Quercetin Glycosides. Type of sugar moieties may have a significant role in influencing peroxyl-radicals scavenging ability of Quercetin Glycosides with monosaccharides as a single sugar moieties. Most of the fractions inhibited the target microbes. S. aureus strains expressed a higher sensitivity to phenolic compounds than E. coli strains.
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analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower phyllanthus emblica l fruits by high performance liquid chromatography electrospray ionization mass spectrometry
Journal of Agricultural and Food Chemistry, 2012Co-Authors: Baoru Yang, Maaria Kortesniemi, Maarit Karonen, Juhapekka SalminenAbstract:Phenolic compounds were extracted from dried emblic leafflower (Phyllanthus emblica L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid Glycosides, Quercetin Glycosides, and eriodictyol coumaroyl Glycosides in the fruits. The study provi...
Juhapekka Salminen - One of the best experts on this subject based on the ideXlab platform.
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analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower phyllanthus emblica l fruits by high performance liquid chromatography electrospray ionization mass spectrometry
Journal of Agricultural and Food Chemistry, 2012Co-Authors: Baoru Yang, Maaria Kortesniemi, Maarit Karonen, Juhapekka SalminenAbstract:Phenolic compounds were extracted from dried emblic leafflower (Phyllanthus emblica L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid Glycosides, Quercetin Glycosides, and eriodictyol coumaroyl Glycosides in the fruits. The study provi...
