Metabolism of quercetin and rutin by the pig caecal microflora prepared by freeze-preservation

Keppler, Katrin; Hein, Eva-Maria; Humpf, Hans‐Ulrich

doi:10.1002/mnfr.200600016

Cited by 35 publications

(28 citation statements)

References 47 publications

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“…Compounds were identified by comparison of the UV spectra and the retention times. The following wavelengths were monitored for quantitative analysis: 360 nm for quercetin, 280 nm for metabolites (12, 13). …”

Section: Methodsmentioning

confidence: 99%

In vitro catabolism of quercetin by human fecal bacteria and the antioxidant capacity of its catabolites

Peng¹,

Zhang²,

Zhang³

et al. 2014

Food & Nutrition Research

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BackgroundPart of quercetin flows into the colon after escaping the absorption of the small intestine and will be degraded by colonic microbiota. The catabolites in the colon partially determine the physiological activity of quercetin.MethodsSeven gut bacteria isolated from human feces were utilized to in vitro ferment quercetin. Their catabolites were analyzed with high-performance liquid chromatography and mass spectrometry, and the antioxidant activities of their fermented broths were compared with that of quercetin.ResultsOne metabolite, 3,4-dihydroxyphenylacetic acid, was produced by both C. perfringens and B. fragilis transforming quercetin. No other metabolites were detected in the other fermented broths. The antioxidant activities of all strains fermenting quercetin reached the highest values at the concentration of 1 mg/mL quercetin in broth; the fermented products of C. perfringens and B. fragilis presented stronger activities than those of other strains at most concentrations of quercetin in broth. Additionally, all of the fermented broths presented a decline of the antioxidant activities compared to quercetin. Therefore, the antioxidant activity of quercetin will be lost when it reaches the human colon because of the gut bacterial fermentation.ConclusionsThis is the first study to report that quercetin can be degraded by C. perfringens and B. fragilis and transformed to the same metabolite, 3,4-dihydroxyphenylacetic acid, and that antioxidant activities decline when quercetin is fermented by seven gut bacteria.

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Section: Methodsmentioning

confidence: 99%

In vitro catabolism of quercetin by human fecal bacteria and the antioxidant capacity of its catabolites

Peng¹,

Zhang²,

Zhang³

et al. 2014

Food & Nutrition Research

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“…An aliquot of the filtrates was inactivated by sterilization at 121 °C for 15 min at 1.1 bar. The inactivated fecal suspensions were used as control for chemical degradation and matrix effects …”

Section: Methodsmentioning

confidence: 99%

Metabolism of cyadox by the intestinal mucosa microsomes and gut flora of swine, and identification of metabolites by high‐performance liquid chromatography combined with ion trap/time‐of‐flight mass spectrometry

Huang

Liu

et al. 2011

Rapid Comm Mass Spectrometry

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Cyadox (CYX), 2-formylquinoxaline-1,4-dioxide cyanoacetylhydrazone, is an antimicrobial and growth-promoting feed additive for food-producing animals. To reveal biotransformation of CYX in swine intestine, CYX was incubated with swine intestinal microsomes and mucosa in the presence of an NADPH-generating system and swine ileal flora and colonic flora, respectively. The metabolites of CYX were identified using high-performance liquid chromatography combined with ion trap/time-of-flight mass spectrometry (LC/MS-ITTOF). Structural elucidation of the metabolites was precisely performed by comparing their changes in molecular mass, full scan MS/MS spectra and accurate mass measurements with those of the parent drug. Finally, seven metabolites were identified as follows: three reduced metabolites (cyadox 1-monoxide (Cy1), cyadox 4-monoxide (Cy2) and bisdesoxycyadox (Cy4)); hydroxylation metabolite (3-hydroxylcyadox 1-monoxide (Cy3)); hydrolysis metabolite of the amide bond (N-decyanoacetyl cyadox (Cy5)); a hydrogenation metabolite (11,12-dihydro-bisdesoxycyadox (Cy6)) and a side-chain cleavage metabolite (2-hydromethylquinoxaline (Cy7)). Only one metabolite (Cy1) was found in intestinal microsomes. Cy1, Cy2 and Cy4 were detected in intestinal mucosa, ileal and colonic flora. In addition, Cy3 and Cy5 were only obtained from ileal flora, and Cy6 and Cy7 alone were observed in colonic bacteria. The results indicated that N→O group reduction was the main metabolic pathway of CYX metabolism in swine ileal flora, intestinal microsomes and mucosa. New metabolic profiles of hydrogenation and cleavage on the side chain were found in colonic bacteria. Among the identified metabolites, two new metabolites (Cy6, Cy7) were detected for the first time. These studies will contribute to clarify comprehensively the metabolism of CYX in animals, and provide evidence to explain the pharmacology and toxicology effects of CYX in animals.

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“…In an in vitro study utilizing the flora from pig cecum, rutin was shown to by deglycosylated to quercetin and it could be further metabolized to phloroglucinol and 3,4-dihydroxyphenylacetic acid (97). The result was different when human gut microflora was used, where quercetin was metabolized to 4hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,4dihydroxyphenylacetic acid (14).…”

Section: Flavonolsmentioning

confidence: 97%

Metabolites Are Key to Understanding Health Effects of Wine Polyphenolics

Forester

Waterhouse

2009

The Journal of Nutrition

108

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Phenolic compounds in grapes and wine are grouped within the following major classes: stilbenes, phenolic acids, ellagitannins, flavan-3-ols, anthocyanins, flavonols, and proanthocyanidins. Consumption of foods containing phenolic substances has been linked to beneficial effects toward chronic diseases such as coronary heart disease and colorectal cancer. However, such correlations need to be supported by in vivo testing and bioavailability studies are the first step in establishing cause and effect. Class members from all phenolic groups can be glucuronidated, sulfated, and/or methylated and detected at low concentrations in the bloodstream and in urine. But the majority of phenolic compounds from grapes and wine are metabolized in the gastrointestinal tract, where they are broken down by gut microflora. This typically involves deglycosylation, followed by breakdown of ring structures to produce phenolic acids and aldehydes. These metabolites can be detected in bloodstream, urine, and fecal samples by using sophisticated instrumentation methods for quantitation and identification at low concentrations. The health effects related to grape and wine consumption may well be due to these poorly understood phenolic acid metabolites. This review discusses the known metabolism of each major class of wine and grape phenolics, the means to measure them, and ideas for future investigations.

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Metabolism of quercetin and rutin by the pig caecal microflora prepared by freeze-preservation

Cited by 35 publications

References 47 publications

In vitro catabolism of quercetin by human fecal bacteria and the antioxidant capacity of its catabolites

In vitro catabolism of quercetin by human fecal bacteria and the antioxidant capacity of its catabolites

Metabolism of cyadox by the intestinal mucosa microsomes and gut flora of swine, and identification of metabolites by high‐performance liquid chromatography combined with ion trap/time‐of‐flight mass spectrometry

Metabolites Are Key to Understanding Health Effects of Wine Polyphenolics

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