Efficiency of Absorption and Metabolic Conversion of Quercetin and Its Glucosides in Human Intestinal Cell Line Caco-2

Murota, Kazuo; Shimizu, Sumie; Chujo, Hitomi; Moon, Jae‐Hak; Terao, Junji

doi:10.1006/abbi.2000.2123

Cited by 130 publications

(111 citation statements)

References 29 publications

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“…The viability of HL-60 cells was reduced by about 50% with cyanidin-3-glucoside at 300 μg/mL and present in rat plasma (0.31 μmol/L), while Miyazawa et al (1999) reported the direct intestinal absorption of anthocyanins in the intact glycoside form, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into human bodies after oral supplementation, and that no aglycons or conjugates of anthocyanins occurred in human plasma (24 nmol of cyanidin-3-glucoside /L). On cellular uptake, Murota et al (2000) reported that quercetin, which is not a member of the anthocyanidin family, but is one of the flavonoids, passed through Caco-2 monolayers much more efficiently than quercetin glucosides. Kawai et al (2008) reported that quercetin-3-glucuronide, which is a major antioxidative quercetin metabolite in human plasma, was significantly taken up and deconjugated into the much more active aglycones in activated macrophages.…”

Section: Discussionmentioning

confidence: 99%

Differential Effects of Cyanidin and Cyanidin-3-glucoside on Human Cell Lines

Takeuchi

Ohtani

et al. 2011

FSTR

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Anthocyanins are pigments in plants. Anthocyanins and their aglycons, anthocyanidins, have various biological effects. In the present study, we examined the effects of cyanidin and cyanidin-3-glucoside on intracellular reactive oxygen species (ROS) levels and on proliferative effects, using four cancer cell lines and one normal cell line, and we found that cyanidin (100 μmol/L) has significant effects when compared with cyanidin-3-glucoside. Cyanidin reduced intracellular ROS levels in MCF-7, HuH-7, HepG2, Caco-2 and HUVEC cell lines, but cyanidin-3-glucoside did not. Cyanidin inhibited the proliferation of MCF-7, HuH-7, HepG2 and Caco-2 cells, but cyanidin-3-glucoside did not. Cyanidin and cyanidin-3-glucoside had no effect on the proliferation of HUVEC. We also tested cyanidin-3-rutinoside, peonidin and peonidin-3-glucoside, but the presence of a sugar in their structure hampered the biological effects of aglycons. These results suggest that a sugar in the anthocyanin structure affects biological activity.

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Section: Discussionmentioning

confidence: 99%

Differential Effects of Cyanidin and Cyanidin-3-glucoside on Human Cell Lines

Takeuchi

Ohtani

et al. 2011

FSTR

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“…Quercetin and other flavonoids are substrates for uridine diphosphateglucuronosyltransferases (UDP GT) in the human intestine [14] . UDPGT glucuronidates the quercetin aglycone into quercetin glucuronides (conjugated quercetin metabolites) and then it finally reaches the bloodstream [4,9] (Figure 3). …”

Section: Absorption Of Iqmentioning

confidence: 99%

“…A fatenriched diet enhances quercetin3Oglucoside bioavailability, which might be owing to improved solubility and enhanced absorption of the lipophilic quercetin aglycone via lipid micelles, as well as delayed elimination of quercetin from the plasma owing to a prolonged enter ohepatic circulation [12] . It is important to note that follow ing the enzymatic hydrolysis by hesperidinase, rutin is mainly bioconverted into Q3G [4,7,8,1012] , thereby increasing the absorption [15] and bioavailability [16] .…”

Section: Absorption Of Iqmentioning

confidence: 99%

“…Published literature often considers them to be the same compound and uses the names interchangeably, as is the case in this present review. In addition, quercetin and IQ differ in their structure, bioavailability, absorption, and biological actions [2,4] . The absorption of flavonoids in the small intestine is limited owing to their molecular weight and hydrop hilicity of their glycosides.…”

Section: Introductionmentioning

confidence: 99%

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Review of anticancer mechanisms of isoquercitin

Orfali¹,

Duarte²,

Bonadio³

et al. 2016

WJCO

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This review was based on a literature search of PubMed and Scielo databases using the keywords "quercetin, rutin, isoquercitrin, isoquercitin (IQ), quercetin-3-glucoside, bioavailability, flavonols and favonoids, and cancer" and combinations of all the words. We collected relevant scientific publications from 1990 to 2015 about the absorption, bioavailability, chemoprevention activity, and treatment effects as well as the underlying anticancer mechanisms of isoquercitin. Flavonoids are a group of polyphenolic compounds widely distributed throughout the plant kingdom. The subclass of flavonols receives special attention owing to their health benefits. The main components of this class are quercetin, rutin, and IQ, which is a flavonoid and although mostly found as a glycoside, is an aglycone (lacks a glycoside side chain). This compound presents similar therapeutic profiles to quercetin but with superior bioavailability, resulting in increased efficacy compared to the aglycone form. IQ has therapeutic applications owing to its wide range of pharmacological effects including antioxidant, antiproliferative, anti-inflammatory, anti-hypertensive, and anti-diabetic. The protective effects of IQ in cancer may be due to actions on lipid peroxidation. In addition, the antitumor effect of IQ and its underlying mechanism are related to interactions with Wnt signaling pathway, mixed-lineage protein kinase 3, mitogen-activated protein kinase, apoptotic pathways, as well proinflammatory protein signaling. This review contributed to clarifying the mechanisms of absorption, metabolism, and actions of IQ and isoquercitrin in cancer.

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“…According to that quercetin is poorly absorbed in human body because no enzyme is known to split the glycosidic bond. Aglycones, sugar-free flavonoids can easily pass through the gut wall, but flavonoids are rarely found as aglycones in plants 6 .…”

Section: Figure 1 Molecular Structure Of Flovonols (Left) and Quercementioning

confidence: 99%

Enhancement of flavonols water solubility by cyclodextrin inclusion complex formation - case study

Łukasiewicz

Kowalski

2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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Abstract:The phenomenon of solubility increasing of nonpolar flavonol antioxidant -quercetin (QC) in water solutions containing β-cyclodextrin (CD) was studied. Complexation of QC by CD was investigated using phase solubility study. It allows to estimate the apparent formation constant for 1:1 host-guest complex. Additionally thermodynamic properties were evaluated as well showing spontaneous exothermic process of complex formation. Two solubility models were also employing to verify their applicability to predict QC concentration in solution. Those models included modified Apelbalt and Buchowski-Ksiazczak equations. In order to investigate the antioxidant properties of ternary systems QC/CD/water a radical scavenging activity using stable radical of DPPH was performed. Experiments indicated that antioxidant activity is temperature and CD concentration-dependent. It was shown that complexation may inhibit the radical scavenging by QC or changing the scavenging stoichiometry. Keywords:cyclodextrin, inclusion complexes, thermodynamics, solubility modeling Introduction:

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Efficiency of Absorption and Metabolic Conversion of Quercetin and Its Glucosides in Human Intestinal Cell Line Caco-2

Cited by 130 publications

References 29 publications

Differential Effects of Cyanidin and Cyanidin-3-glucoside on Human Cell Lines

Differential Effects of Cyanidin and Cyanidin-3-glucoside on Human Cell Lines

Review of anticancer mechanisms of isoquercitin

Enhancement of flavonols water solubility by cyclodextrin inclusion complex formation - case study

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