Anthocyanins are phenolic compounds widely distributed in fruits and vegetables. Their consumption has been shown to prevent some chronic diseases. Anthocyanin metabolism, however, is still not fully understood. The aim of this work was to evaluate the bioavailability of anthocyanins in humans consuming a meal containing strawberries and to identify possible metabolites in urine. Six healthy volunteers (three women and three men) consumed a meal containing 200 g strawberries (providing 179 micro mol pelargonidin-3-glucoside). Urine samples were collected before and after the meal and rapidly treated by solid-phase extraction. Identification and quantification of anthocyanin metabolites were carried out by HPLC-ESI-MS-MS and HPLC with UV-visible detection, respectively. In addition to pelargonidin-3-glucoside, five anthocyanin metabolites were identified in urine: three monoglucuronides of pelargonidin, one sulfoconjugate of pelargonidin and pelargonidin itself. Total urinary excretion of strawberry anthocyanin metabolites corresponded to 1.80 +/- 0.29% (mean +/- SEM, n = 6) of pelargonidin-3-glucoside ingested. More than 80% of this excretion was related to a monoglucuronide. Four hours after the meal, more than two-thirds of anthocyanin metabolites had been excreted, although urinary excretion of the metabolites continued until the end of the 24-h experiment. This study demonstrated that anthocyanins were glucuro- and sulfo-conjugated in humans and that the main metabolite of strawberry anthocyanins in human urine was a monoglucuronide of pelargonidin.
Anthocyanins are present in human diet due to their wide occurrence in fruits and beverages. They possess antioxidant activities and could be involved in several health effects. The aim of this study was to investigate anthocyanin metabolism and distribution in the digestive area organs (stomach, jejunum and liver) and kidney, as well as a target tissue (brain) in rats fed with a blackberry (Rubus fruticosus L.) anthocyanin-enriched diet for 15 days. Identification and quantification of anthocyanin metabolites was carried out by HPLC-ESI-MS-MS and HPLC-DAD, respectively. The stomach exhibited only native blackberry anthocyanins (cyanidin 3-O-glucoside and cyanidin 3-O-pentose), while in other organs (jejunum, liver, and kidney) native and methylated anthocyanins as well as conjugated anthocyanidins (cyanidin and peonidin monoglucuronides) were identified. Proportions of anthocyanin derivatives differed according to the organ considered, with the liver presenting the highest proportion of methylated forms. Jejunum and plasma also contained aglycone forms. In the brain, total anthocyanin content (blackberry anthocyanins and peonidin 3-O-glucoside) reached 0.25 +/- 0.05 nmol/g of tissue (n = 6). The urinary excretion of total anthocyanins was low (0.19 +/- 0.02% of the ingested amount). Thus, organs of the digestive area indicated a metabolic pathway of anthocyanins with enzymatic conversions (methylation and/or glucurono-conjugation). Moreover, following consumption of an anthocyanin-rich diet, anthocyanins enter the brain.
After consumption, anthocyanins are rapidly absorbed as glycosides. Their rapid appearance in plasma could result from absorption through the gastric wall. The aim of this study was to evaluate the fate of anthocyanins in the stomach. Absorption of purified anthocyanins (14 micromol/L) as well as blackberry 14 and 750 micromol/L) and bilberry (88 micromol/L) anthocyanins was compared after in situ gastric administration for 30 min. A high proportion (approximately 25%) of anthocyanin monoglycosides (glucoside or galactoside) was absorbed from the stomach, whereas absorption of cyanidin 3-rutinoside was lower. Bilberry anthocyanins were also efficiently absorbed, but absorption varied greatly (19-37%) according to the anthocyanin structure; delphinidin glycosides were the most absorbed. When a high concentration of blackberry anthocyanins (750 micromol/L) was injected into the gastric lumen, the percentage of cyanidin 3-glucoside (Cy 3-glc) absorption was lower than after administration of a low concentration (14 micromol/L). After administration of this high concentration, blackberry anthocyanins were observed in plasma from gastric vein and aorta, whereas neither aglycones nor metabolites were detected. Analysis of bile samples revealed that Cy 3-glc appeared in bile after as little as 20 min. Peonidin 3-glucoside (the methylated form of Cy 3-glc) as well as unknown anthocyanin metabolites were also observed in bile. Thus, this study demonstrated that anthocyanin glycosides were quickly and efficiently absorbed from the stomach and rapidly excreted into bile as intact and metabolized forms.
Anthocyanins are natural pigments that possess antioxidant activities and are implicated in various health effects. Recent studies showed that the stomach is a site of anthocyanin absorption. However, the fate of anthocyanins in the small intestine remains unknown. We therefore investigated anthocyanin absorption after in situ perfusion of the jejunum + ileum in rats. The intestine was perfused for 45 min with a physiological buffer supplemented with various anthocyanins. Purified anthocyanin glycosides (9.2 nmol/min) or blackberry (9.0 nmol/min) or bilberry (45.2 nmol/min) anthocyanins were perfused. A high proportion of anthocyanin glycosides was absorbed through the small intestine after perfusion. The rate of absorption was influenced by the chemical structure of the anthocyanin and varied from 10.7 (malvidin 3-glucoside) to 22.4% (cyanidin 3-glucoside). Regardless of the anthocyanins perfused, only glycosides were recovered in the intestinal lumen. After perfusion of a high amount of blackberry anthocyanins (600 nmol/min), native cyanidin 3-glucoside was recovered in urine and plasma from the aorta and mesenteric vein. Methylated and/or glucuronidated derivatives were also identified. Analysis of bile samples revealed that cyanidin 3-glucoside and its methylated derivatives (peonidin 3-glucoside + peonidin glucuronide) quickly appeared in bile. This study demonstrated that anthocyanin glycosides are rapidly and efficiently absorbed from the small intestine. Furthermore, anthocyanins are quickly metabolized and excreted into bile and urine as intact glycosides as well as methylated forms and glucuronidated derivatives.
The consumption of anthocyanins has been shown to prevent certain chronic diseases. However, anthocyanin metabolism has not yet been fully elucidated. The aim of this study was to evaluate anthocyanin urinary excretion in humans receiving a meal containing blackberries and to identify possible metabolites in urine. Five healthy volunteers were fed 200 g of blackberries (960 mumol of anthocyanins). Urine samples were collected and rapidly treated by solid-phase extraction. Anthocyanin metabolites were identified and quantified by HPLC-ESI-MS-MS and HPLC with UV-vis detection, respectively. In addition to native cyanidin 3-glucoside, several other anthocyanin metabolites were identified in the urine: methylated glycosides, glucuronides of anthocyanidins and anthocyanins, a sulfoconjugate of cyanidin, and anthocyanidins. Total urinary excretion of blackberry anthocyanin metabolites was 0.160 +/- 0.020% (n = 5) of the amount of anthocyanins ingested. Monoglucuronides of anthocyanidins represented >60% of this excretion. Urinary excretion of anthocyanins was maximal between 2 and 4 h after the meal, but continued during the 24 h of the experiment. This study highlighted the influence of aglycon structure on anthocyanin urinary excretion. It demonstrated that anthocyanins are not only methylated but also glucuroconjugated and sulfoconjugated in humans and that the main metabolites of blackberry anthocyanins in human urine were anthocyanidin monoglucuronides.
Anthocyanins are natural pigments that could be involved in various health effects. Red oranges are an important dietary source of anthocyanins, including cyanidin 3-glucoside (Cy 3-glc) and an acylated derivative, cyanidin 3-(6 00 -malonyl)-glucoside (Cy 3-malglc). The aim of this study was to evaluate the absorption and metabolism of red orange anthocyanins in rats fed an anthocyanin-enriched diet for 12 d (approximately 2·8 mmol anthocyanins/d). Furthermore, the absorption of these anthocyanins was studied in both the stomach and intestine using in situ models in rats. Anthocyanin metabolites were identified and quantified by HPLC -electrospray ionization tandem MS and HPLC -diode array detection, respectively. The red orange anthocyanins, Cy 3-glc and Cy 3-malglc, as well as their respective methylated derivatives, were recovered in urine after red orange juice intake. The 24 h urinary excretion of total anthocyanins was low (0·081 (SEM 0·009) % of the ingested amount). However, a high proportion (about 20 %) of red orange anthocyanins was absorbed from the stomach. More Cy 3-malglc than Cy 3-glc was absorbed in the intestine. This study thus indicated that red orange juice anthocyanins were rapidly absorbed from both stomach and small intestine, and then excreted in the urine as intact and methylated forms. Moreover, the absorption and metabolism of acylated anthocyanins and non-acylated anthocyanins were similar.
Anthocyanins are secondary metabolites from the flavonoid family, frequently found in fruits and vegetables. They have been shown to possess beneficial health effects and various in vitro assays have highlighted their powerful antioxidant capacity. However, little is known about their metabolism after digestion and their antioxidant potency in vivo. The aim of this work was to evaluate anthocyanin bioavailability and to determine the impact of an anthocyanin-rich diet on plasma antioxidant status in rats. Animals were fed for 8 days with a vitamin E-deficient diet supplemented with a bilberry (Vaccinium myrtillus L.) anthocyanin extract providing daily 1.43 mmol anthocyanins kg −1 body weight. An anthocyanin-enriched diet significantly enhanced the plasma antioxidant capacity compared with a control diet (P < 0.0001). Moreover, anthocyanins were recovered in urine in the intact glycosidic forms in addition to unknown metabolites. Urinary excretion of bilberry anthocyanins and their metabolites was 0.71 ± 0.08 µmol per 24 h (ie 0.22% of the ingested dose). Anthocyanins and their corresponding aglycones were detected in caecal contents. After a single oral administration of the bilberry extract, native anthocyanins quickly (30 min) appeared in plasma. Hence, in spite of a low bioavailability, bilberry anthocyanin extract consumption has a positive effect on plasma antioxidant capacity.
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