Reaction Between Malvidin 3‐Glucoside and (+)‐Catechin in Model Solutions Containing Different Aldehydes

Pissarra, José; Mateus, Nuno; Rivas-Gonzalo, Julián C.; Buelga, Celestino Santos; Freitas, Victor de

doi:10.1111/j.1365-2621.2003.tb05697.x

Cited by 133 publications

(119 citation statements)

References 17 publications

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“…The extract was filtrated in a 50 mm nylon membrane and then purified by Toyopearl gel HW-40(S) column chromatography according to the procedure previously described [12]. The fraction corresponding to the anthocyanidin monoglucosides was collected, the solvent was partially evaporated in a rotary evaporator at 301C and the sample was freeze dried and stored at À201C until use.…”

Section: Anthocyanins Extract Preparationmentioning

confidence: 99%

Absorption of anthocyanins through intestinal epithelial cells – Putative involvement of GLUT2

Faria

Pestana

Azevedo

et al. 2009

Molecular Nutrition Food Res

150

105

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Anthocyanins bioavailability is a major issue regarding their biological effects and remains unclear due to few data available on this matter. This work aimed to evaluate the absorption of anthocyanins at the intestine using Caco-2 cells. Anthocyanin extract, rich in malvidin-3-glucoside, was obtained from red grape skins and tested on Caco-2 cells. The absorption of anthocyanins, in absence or presence of 1% ethanol, was detected by HPLC/DAD/LC-MS. Our results showed that this transport was significantly increased in the presence of ethanol especially after 60 min of incubation. In addition, cells that were pretreated for 96 h with anthocyanins (200 microg/mL) showed an increase of their own transport (about 50% increase). Expression of glucose transporters sodium-dependent glucose transporter 1, facilitative glucose transporters 5, and facilitative glucose transporters 2 was assessed by RT-PCR. It was found that facilitative glucose transporters 2 expression was increased (60%) in Caco-2 cells pretreated with anthocyanins, by comparison with controls. When the effect of anthocyanin extract on (3)H-2-deoxy-D-glucose uptake was tested, an inhibitory effect was observed (about 60% decrease). However, the malvidin aglycone was tested and had no effect. In conclusion, anthocyanins could be absorbed through Caco-2 cells, and can interfere with their own transport and also with glucose intestinal uptake.

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Section: Anthocyanins Extract Preparationmentioning

confidence: 99%

Absorption of anthocyanins through intestinal epithelial cells – Putative involvement of GLUT2

Faria

Pestana

Azevedo

et al. 2009

Molecular Nutrition Food Res

150

105

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“…Pigments from the anthocyanin-flavanol condensation involving aldehydes other than acetaldehyde have also been described (Es-Safi, Cheynier, & Moutounet, 2002;Pissarra, Mateus, Rivas-Gonzalo, Santos-Buelga, & De Freitas, 2003;Pissarra, Lourenço, et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Flavanol–anthocyanin condensed pigments in plant extracts

et al. 2006

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Pigments resulting from the direct condensation of anthocyanins and flavanols are usually associated with reactions taking place during processing and storage of plant-derived foods and beverages and have been particularly studied in aged red wines. In this paper, small amounts of flavanol-anthocyanin condensed pigments are found in different plant extracts. Structures are suggested for 10 such condensed pigments detected in extracts of strawberry, runner beans, purple corn and grape skins, based on their MS n fragmentation patterns, following analyses by electrospray tandem mass spectrometry. All of them correspond to dimers containing a flavan-3-ol [either (epi)afzelechin, (epi)catechin or (epi)gallocatechin] as the upper unit carbon-carbon linked to a lower anthocyanin unit consisting of different delphinidin, cyanidin, pelargonidin, peonidin or malvidin derivatives. The detection of these pigments in plant extracts may suggest that they are natural pigments and not products exclusively formed during storage and ageing of processed foods and beverages, as was previously assumed.

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“…Anthocyanins may react with flavanols to produce more stable pigments, either directly or by means of different aldehydes (e.g. acetaldehyde, propionaldehyde) (Pisarra et al, 2003). Flavan-3-ols (monomeric catechins and proanthocyanidins) are another large family of phenolic compounds that are mainly responsible for the astringency, bitterness and structure of wines.…”

Section: Introductionmentioning

confidence: 99%

Study of the Phenolic Composition of Shiraz Red Grape Cultivar (Vitis vinifera L.) Cultivated in North-eastern Thailand and its Antioxidant and Antimicrobial Activity

Butkhup

Chowtivannakul

Gaensakoo

et al. 2016

SAJEV

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The seed, skin and whole grape extract of the red grape cultivar Shiraz, which is widely cultivated in Northeastern Thailand, were investigated. Total phenolic, total flavonoid and total monomeric anthocyanin content ranged from 48.04 to 116.73 g GAE/100g db (dry weight base), 74.82 to 258.69 mg CE/g db, and 5.06 to 55.45 mg/100g db, respectively. Dimeric procyanidin (119.56-484.08 mg/100g db), (+)-catechin (52.30-231.92 mg/100g db), (-)-epicatechin (27.92-174.10 mg/100g db), and gallic acid (4.42-27.80 mg/100g db) were found to be the main flavanols that were present in the seed. Rutin and trans-resveratrol were present in amounts of between 21.13 and 40.05 and 2.85 and 3.60 mg/100g db respectively. All extracts showed remarkable DPPH radical-scavenging activity (EC 50 ), ranging from 0.47 to 2.10 µg/mL. Methanolic extract from the seed and skin were also active against all Gram-positive bacteria, but these exerted less of an inhibiting effect on the growth of the tested Gram-negative bacteria. The activity of the methanolic extract of the seed was effective against B. cereus ATCC 11778, B. subtilis ATCC 6633 and S. faecalis TISTR 459.

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Reaction Between Malvidin 3‐Glucoside and (+)‐Catechin in Model Solutions Containing Different Aldehydes

Cited by 133 publications

References 17 publications

Absorption of anthocyanins through intestinal epithelial cells – Putative involvement of GLUT2

Absorption of anthocyanins through intestinal epithelial cells – Putative involvement of GLUT2

Flavanol–anthocyanin condensed pigments in plant extracts

Study of the Phenolic Composition of Shiraz Red Grape Cultivar (Vitis vinifera L.) Cultivated in North-eastern Thailand and its Antioxidant and Antimicrobial Activity

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