Metabolism of anthocyanins and their phenolic degradation products by the intestinal microflora

Keppler, Katrin; Humpf, Hans‐Ulrich

doi:10.1016/j.bmc.2005.05.003

Cited by 335 publications

(313 citation statements)

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“…Benzoic acid and hippuric acid are known to be colonic metabolites of anthocyanins (Kim et al, 1998). However, concentrations of the four phenolic acids decreased gradually after peaking at 30 min, indicating further chemical or microbial degradation of the phenolic compounds, as suggested by Keppler and Humpf (2005). The quantity of hippuric acid formed by biosynthesis is reported to directly correlate with the concentrations of its precursors, primarily phenolic acids (benzoic acid and salicylic acid) (Toromanovic et al, 2008).…”

Section: Discussionmentioning

confidence: 96%

“…Several studies have demonstrated possible beneficial effects of anthocyanins on chronic degenerative diseases, including CVD and cancer (Tsuda et al, 1996;Prior and Cao, 2000;Kay and Holub, 2002;Nakamura et al, 2002;Hou, 2003;Kang et al, 2003;Xu et al, 2004;Rechner and Kroner, 2005;Dalgard et al, 2009). Anthocyanins have low bioavailability (Kay, 2006;Hollands et al, 2008) and are metabolised in humans into methylated derivatives, glucuronides and sulfoconjugates (Wu et al, 2002;Felgines et al, 2003Felgines et al, , 2005Kay et al, 2004Kay et al, , 2005, but phenolic acids are the major stable metabolites of anthocyanins in vivo (Keppler and Humpf, 2005;Fleschhut et al, 2006). Endothelial cell dysfunction is a critical initiating event in the progression of atherosclerosis (Ross, 1999), but the effects of anthocyanins on endothelial function at normal intake levels have not been reported previously.…”

Section: Introductionmentioning

confidence: 99%

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A randomised trial to investigate the effects of acute consumption of a blackcurrant juice drink on markers of vascular reactivity and bioavailability of anthocyanins in human subjects

et al. 2011

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Background/Objectives: To study the bioavailability of anthocyanins and the effects of a 20% blackcurrant juice drink on vascular reactivity, plasma antioxidant status and other cardiovascular disease risk markers. Subjects/Methods: The study was a randomised, cross-over, double-blind, placebo-controlled acute meal study. Twenty healthy volunteers (11 females and 9 males) were recruited, and all subjects completed the study. Fasted volunteers consumed a 20% blackcurrant juice drink (250 ml) or a control drink following a low-flavonoid diet for the previous 72 h. Vascular reactivity was assessed at baseline and 120 min after juice consumption by laser Doppler imaging (LDI). Plasma and urine samples were collected periodically over an 8-h period for analysis, with a final urine sample collected at 24 h. The cross-over was performed after a 4-week washout. Results: There were no significant effects of the 20% blackcurrant juice drink on acute measures of vascular reactivity, biomarkers of endothelial function or lipid risk factors. Consumption of the test juice caused increases in plasma vitamin C (P ¼ 0.006), and urinary anthocyanins (Po0.001). Delphinidin-3-rutinoside and cyanidin-3-rutinoside were the main anthocyanins excreted in urine with delphinidin-3-glucoside also detected. The yield of anthocyanins in urine was 0.021±0.003% of the dietary intake of delphinidin glycosides and 0.009±0.002% of the dietary intake of cyanidin glycosides. Conclusions: The juice consumption did not have a significant effect on vascular reactivity. Anthocyanins were present at low concentrations in the urine, and microbial metabolites of flavonoids were detected in plasma after juice consumption.

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Section: Discussionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

A randomised trial to investigate the effects of acute consumption of a blackcurrant juice drink on markers of vascular reactivity and bioavailability of anthocyanins in human subjects

et al. 2011

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“…More recently, it has been established that the intestinal microflora plays a key role in the metabolism of anthocyanins. After ingestion, anthocyanins can be hydrolyzed by intestinal glucosidases and the resulting aglycones are further metabolised in the large intestine to other breakdown metabolites such as protocatechuic, gallic, syringic, and vanillic acids (Avila et al 2009;Forester and Waterhouse 2008;Keppler and Humpf 2005;Vitaglione et al 2007). Moreover, gallic acid has been determined in plasma after its ingestion at levels as high as 1.8 lmol/L in its original form and at 2.2 lmol/L as its derivative 4-Omethylgallic acid (Shahrzad and Bitsch 1998;Shahrzad et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Potential anti-inflammatory, anti-adhesive, anti/estrogenic, and angiotensin-converting enzyme inhibitory activities of anthocyanins and their gut metabolites

et al. 2012

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Epidemiological studies have indicated a positive association between the intake of foods rich in anthocyanins and the protection against cardiovascular diseases. Some authors have shown that anthocyanins are degraded by the gut microflora giving rise to the formation of other breakdown metabolites, which could also contribute to anthocyanin health effects. The objective of this study was to evaluate the effects of anthocyanins and their breakdown metabolites, protocatechuic, syringic, gallic, and vanillic acids, on different parameters involved in atherosclerosis, including inflammation, cell adhesion, chemotaxis, endothelial function, estrogenic/anti-estrogenic activity, and angiotensin-converting enzyme (ACE) inhibitory activity. From the assayed metabolites, only protocatechuic acid exhibited a slight inhibitory effect on NO production and TNF-a secretion in LPS-INF-c-induced macrophages. Gallic acid caused a decrease in the secretion of MCP-1, ICAM-1, and VCAM-1 in endothelial cells. All anthocyanins showed an ACE-inhibitory activity. Delphinidin-3-glucoside, pelargonidin-3-glucoside, and gallic acid showed affinity for ERb and pelargonidin and peonidin-3-glucosides for ERa. The current data suggest that anthocyanins and their breakdown metabolites may partly provide a protective effect against atherosclerosis that is multi-causal and involves different biochemical pathways. However, the concentrations of anthocyanins and their metabolites, as used in the present cell culture and in vitro assays mediating anti-inflammatory, anti-adhesive, antiestrogenic, and angiotensin-converting enzyme inhibitory activities, were often manifold higher than those physiologically achievable.

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“…On absorption into the body, glycosylated flavonoids, which include anthocyanins, are deglycosylated and conjugated with glucuronide and sulfate (Scalbert and Williamson, 2000;Keppler and Humpf, 2005), although Tsuda et al (1999b) reported that cyanidin-3-glucoside was absorbed…”

Section: Fig 5 Effects Of Various Anthocyanins and Anthocyanidins Onmentioning

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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Metabolism of anthocyanins and their phenolic degradation products by the intestinal microflora

Cited by 335 publications

References 52 publications

A randomised trial to investigate the effects of acute consumption of a blackcurrant juice drink on markers of vascular reactivity and bioavailability of anthocyanins in human subjects

A randomised trial to investigate the effects of acute consumption of a blackcurrant juice drink on markers of vascular reactivity and bioavailability of anthocyanins in human subjects

Potential anti-inflammatory, anti-adhesive, anti/estrogenic, and angiotensin-converting enzyme inhibitory activities of anthocyanins and their gut metabolites

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

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