Anthocyanins and their metabolism in the in vitro gastrointestinal tract

Anna-Marja Aura, Marja Vainionpää, Marina Heinonen, Pilar Martinez Lopez, Celestino Santos-Buelga, Kirsi-Marja Oksman-Caldentey, Riitta Puupponen-Pimiä, Kaisa Poutanen

Research output: Chapter in Book/Report/Conference proceedingConference article in proceedingsScientific

Abstract

Anthocyanins are flavonoids which produce blue, purple red and intermediate colours in plants. They are present as glycosides with an anthocyanidin C6-C3-C6 skeleton, whose structure is dependent on pH. Anthocyanins are poorly detected from the biological fluids: plasma and urine. They may be poorly absorbed or they undergo changes in their structure. Nevertheless, large amounts of the ingested compounds are likely to enter the colon either within the matrix of the dietary source or through enterohepatic circulation. In vitro and in vivo studies have shown that colonic bacteria transform various flavonoids to smaller phenolic acids. However, there is very little information on bacterial transformations of anthocyanins. Aims of the study were to find out the release and changes of anthocyanins in the in vitro upper intestinal model and their bacterial metabolism in the colon model. Frozen berries, bilberry (Vaccinium myrtillus) and red raspberry (Rebus idaeus, v. Ottawa), were subjected to physiological conditions in the presence and absence of active or heat-inactivated alimentary enzymes (salivary amylase, pepsin, pancreatin and mucin) in successive stages of mouth, stomach and duodenum. Changes in stomach and duodenum were compared for their anthocyanin response by HPLC detected at 520 nm. Bacterial transformations of pure anthocyanins (cyanidin-3-glucoside and -rutinoside) isolated from red blum (Prunus domestica L.) and red grapes (Vitis vinifera L.) were studied in an in vitro colon model using human faecal microbiota as an inoculum. Metabolites were analysed and characterized by HPLC-DAS and LC-MS. They were identified by comparing their characteristics with those of available standards, and semi-quantified using the amount of substrate analysed from samples at initial timepoint. Anthocyanins gave a good response as flavylium cations in 520 nm in acidic conditions mimicking stomach and the detection was decreased dramatically in neutral to mildly basic conditions of duodenum indicating opening of the flavylium cation to quinoidal base. In the colon model in vitro cyanidin-3-rutinoside and cyanidin-3-glucoside were deglycosylated and formation of three low molecular weight metabolites were shown. The major metabolite at earlier time points was identified as protocatechuic acid. Furthermore, reconjugation of the aglycone with other groups, non-typical for dietary anthocyanins, was evident at the later timepoints. In conclusion, anthocyanins are poorly detected due to their pH dependent structural characteristics and their bioavailability is difficult to define on the basis of detection of flavylium cations only. Also, smaller molecular weight metabolites are formed due to bacterial actions in the colon, which involve the cleavage of glycosidic linkages, breakdown of the anthocyanidin heterocycle and reconjugation of the aglycone. Information about the health effects of the bacterial metabolites in general is scarce and therefore research directed to this area is necessary.
Original languageEnglish
Title of host publicationPolyphenols communications 2004
EditorsAntti Hoikkala, Otto Soidinsalo
Place of PublicationJyväskylä
PublisherGummerus
ISBN (Print)952-10-1977-8
Publication statusPublished - 2004
MoE publication typeB3 Non-refereed article in conference proceedings
EventPolyphenols Communications 2004: XXII International Conference on Polyphenols - Helsinki, Finland
Duration: 25 Aug 200428 Aug 2004

Conference

ConferencePolyphenols Communications 2004
CountryFinland
CityHelsinki
Period25/08/0428/08/04

Fingerprint

gastrointestinal system
anthocyanins
metabolism
colon
metabolites
duodenum
cations
anthocyanidins
stomach
cyanidin
glucosides
flavonoids
keracyanin
glycosidic linkages
molecular weight
health information
bilberries
Rubus idaeus
Vaccinium myrtillus
protocatechuic acid

Cite this

Aura, A-M., Vainionpää, M., Heinonen, M., Martinez Lopez, P., Santos-Buelga, C., Oksman-Caldentey, K-M., ... Poutanen, K. (2004). Anthocyanins and their metabolism in the in vitro gastrointestinal tract. In A. Hoikkala, & O. Soidinsalo (Eds.), Polyphenols communications 2004 [121] Jyväskylä: Gummerus.
Aura, Anna-Marja ; Vainionpää, Marja ; Heinonen, Marina ; Martinez Lopez, Pilar ; Santos-Buelga, Celestino ; Oksman-Caldentey, Kirsi-Marja ; Puupponen-Pimiä, Riitta ; Poutanen, Kaisa. / Anthocyanins and their metabolism in the in vitro gastrointestinal tract. Polyphenols communications 2004 . editor / Antti Hoikkala ; Otto Soidinsalo. Jyväskylä : Gummerus, 2004.
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title = "Anthocyanins and their metabolism in the in vitro gastrointestinal tract",
abstract = "Anthocyanins are flavonoids which produce blue, purple red and intermediate colours in plants. They are present as glycosides with an anthocyanidin C6-C3-C6 skeleton, whose structure is dependent on pH. Anthocyanins are poorly detected from the biological fluids: plasma and urine. They may be poorly absorbed or they undergo changes in their structure. Nevertheless, large amounts of the ingested compounds are likely to enter the colon either within the matrix of the dietary source or through enterohepatic circulation. In vitro and in vivo studies have shown that colonic bacteria transform various flavonoids to smaller phenolic acids. However, there is very little information on bacterial transformations of anthocyanins. Aims of the study were to find out the release and changes of anthocyanins in the in vitro upper intestinal model and their bacterial metabolism in the colon model. Frozen berries, bilberry (Vaccinium myrtillus) and red raspberry (Rebus idaeus, v. Ottawa), were subjected to physiological conditions in the presence and absence of active or heat-inactivated alimentary enzymes (salivary amylase, pepsin, pancreatin and mucin) in successive stages of mouth, stomach and duodenum. Changes in stomach and duodenum were compared for their anthocyanin response by HPLC detected at 520 nm. Bacterial transformations of pure anthocyanins (cyanidin-3-glucoside and -rutinoside) isolated from red blum (Prunus domestica L.) and red grapes (Vitis vinifera L.) were studied in an in vitro colon model using human faecal microbiota as an inoculum. Metabolites were analysed and characterized by HPLC-DAS and LC-MS. They were identified by comparing their characteristics with those of available standards, and semi-quantified using the amount of substrate analysed from samples at initial timepoint. Anthocyanins gave a good response as flavylium cations in 520 nm in acidic conditions mimicking stomach and the detection was decreased dramatically in neutral to mildly basic conditions of duodenum indicating opening of the flavylium cation to quinoidal base. In the colon model in vitro cyanidin-3-rutinoside and cyanidin-3-glucoside were deglycosylated and formation of three low molecular weight metabolites were shown. The major metabolite at earlier time points was identified as protocatechuic acid. Furthermore, reconjugation of the aglycone with other groups, non-typical for dietary anthocyanins, was evident at the later timepoints. In conclusion, anthocyanins are poorly detected due to their pH dependent structural characteristics and their bioavailability is difficult to define on the basis of detection of flavylium cations only. Also, smaller molecular weight metabolites are formed due to bacterial actions in the colon, which involve the cleavage of glycosidic linkages, breakdown of the anthocyanidin heterocycle and reconjugation of the aglycone. Information about the health effects of the bacterial metabolites in general is scarce and therefore research directed to this area is necessary.",
author = "Anna-Marja Aura and Marja Vainionp{\"a}{\"a} and Marina Heinonen and {Martinez Lopez}, Pilar and Celestino Santos-Buelga and Kirsi-Marja Oksman-Caldentey and Riitta Puupponen-Pimi{\"a} and Kaisa Poutanen",
year = "2004",
language = "English",
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editor = "Antti Hoikkala and Otto Soidinsalo",
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}

Aura, A-M, Vainionpää, M, Heinonen, M, Martinez Lopez, P, Santos-Buelga, C, Oksman-Caldentey, K-M, Puupponen-Pimiä, R & Poutanen, K 2004, Anthocyanins and their metabolism in the in vitro gastrointestinal tract. in A Hoikkala & O Soidinsalo (eds), Polyphenols communications 2004 ., 121, Gummerus, Jyväskylä, Polyphenols Communications 2004, Helsinki, Finland, 25/08/04.

Anthocyanins and their metabolism in the in vitro gastrointestinal tract. / Aura, Anna-Marja; Vainionpää, Marja; Heinonen, Marina; Martinez Lopez, Pilar; Santos-Buelga, Celestino; Oksman-Caldentey, Kirsi-Marja; Puupponen-Pimiä, Riitta; Poutanen, Kaisa.

Polyphenols communications 2004 . ed. / Antti Hoikkala; Otto Soidinsalo. Jyväskylä : Gummerus, 2004. 121.

Research output: Chapter in Book/Report/Conference proceedingConference article in proceedingsScientific

TY - GEN

T1 - Anthocyanins and their metabolism in the in vitro gastrointestinal tract

AU - Aura, Anna-Marja

AU - Vainionpää, Marja

AU - Heinonen, Marina

AU - Martinez Lopez, Pilar

AU - Santos-Buelga, Celestino

AU - Oksman-Caldentey, Kirsi-Marja

AU - Puupponen-Pimiä, Riitta

AU - Poutanen, Kaisa

PY - 2004

Y1 - 2004

N2 - Anthocyanins are flavonoids which produce blue, purple red and intermediate colours in plants. They are present as glycosides with an anthocyanidin C6-C3-C6 skeleton, whose structure is dependent on pH. Anthocyanins are poorly detected from the biological fluids: plasma and urine. They may be poorly absorbed or they undergo changes in their structure. Nevertheless, large amounts of the ingested compounds are likely to enter the colon either within the matrix of the dietary source or through enterohepatic circulation. In vitro and in vivo studies have shown that colonic bacteria transform various flavonoids to smaller phenolic acids. However, there is very little information on bacterial transformations of anthocyanins. Aims of the study were to find out the release and changes of anthocyanins in the in vitro upper intestinal model and their bacterial metabolism in the colon model. Frozen berries, bilberry (Vaccinium myrtillus) and red raspberry (Rebus idaeus, v. Ottawa), were subjected to physiological conditions in the presence and absence of active or heat-inactivated alimentary enzymes (salivary amylase, pepsin, pancreatin and mucin) in successive stages of mouth, stomach and duodenum. Changes in stomach and duodenum were compared for their anthocyanin response by HPLC detected at 520 nm. Bacterial transformations of pure anthocyanins (cyanidin-3-glucoside and -rutinoside) isolated from red blum (Prunus domestica L.) and red grapes (Vitis vinifera L.) were studied in an in vitro colon model using human faecal microbiota as an inoculum. Metabolites were analysed and characterized by HPLC-DAS and LC-MS. They were identified by comparing their characteristics with those of available standards, and semi-quantified using the amount of substrate analysed from samples at initial timepoint. Anthocyanins gave a good response as flavylium cations in 520 nm in acidic conditions mimicking stomach and the detection was decreased dramatically in neutral to mildly basic conditions of duodenum indicating opening of the flavylium cation to quinoidal base. In the colon model in vitro cyanidin-3-rutinoside and cyanidin-3-glucoside were deglycosylated and formation of three low molecular weight metabolites were shown. The major metabolite at earlier time points was identified as protocatechuic acid. Furthermore, reconjugation of the aglycone with other groups, non-typical for dietary anthocyanins, was evident at the later timepoints. In conclusion, anthocyanins are poorly detected due to their pH dependent structural characteristics and their bioavailability is difficult to define on the basis of detection of flavylium cations only. Also, smaller molecular weight metabolites are formed due to bacterial actions in the colon, which involve the cleavage of glycosidic linkages, breakdown of the anthocyanidin heterocycle and reconjugation of the aglycone. Information about the health effects of the bacterial metabolites in general is scarce and therefore research directed to this area is necessary.

AB - Anthocyanins are flavonoids which produce blue, purple red and intermediate colours in plants. They are present as glycosides with an anthocyanidin C6-C3-C6 skeleton, whose structure is dependent on pH. Anthocyanins are poorly detected from the biological fluids: plasma and urine. They may be poorly absorbed or they undergo changes in their structure. Nevertheless, large amounts of the ingested compounds are likely to enter the colon either within the matrix of the dietary source or through enterohepatic circulation. In vitro and in vivo studies have shown that colonic bacteria transform various flavonoids to smaller phenolic acids. However, there is very little information on bacterial transformations of anthocyanins. Aims of the study were to find out the release and changes of anthocyanins in the in vitro upper intestinal model and their bacterial metabolism in the colon model. Frozen berries, bilberry (Vaccinium myrtillus) and red raspberry (Rebus idaeus, v. Ottawa), were subjected to physiological conditions in the presence and absence of active or heat-inactivated alimentary enzymes (salivary amylase, pepsin, pancreatin and mucin) in successive stages of mouth, stomach and duodenum. Changes in stomach and duodenum were compared for their anthocyanin response by HPLC detected at 520 nm. Bacterial transformations of pure anthocyanins (cyanidin-3-glucoside and -rutinoside) isolated from red blum (Prunus domestica L.) and red grapes (Vitis vinifera L.) were studied in an in vitro colon model using human faecal microbiota as an inoculum. Metabolites were analysed and characterized by HPLC-DAS and LC-MS. They were identified by comparing their characteristics with those of available standards, and semi-quantified using the amount of substrate analysed from samples at initial timepoint. Anthocyanins gave a good response as flavylium cations in 520 nm in acidic conditions mimicking stomach and the detection was decreased dramatically in neutral to mildly basic conditions of duodenum indicating opening of the flavylium cation to quinoidal base. In the colon model in vitro cyanidin-3-rutinoside and cyanidin-3-glucoside were deglycosylated and formation of three low molecular weight metabolites were shown. The major metabolite at earlier time points was identified as protocatechuic acid. Furthermore, reconjugation of the aglycone with other groups, non-typical for dietary anthocyanins, was evident at the later timepoints. In conclusion, anthocyanins are poorly detected due to their pH dependent structural characteristics and their bioavailability is difficult to define on the basis of detection of flavylium cations only. Also, smaller molecular weight metabolites are formed due to bacterial actions in the colon, which involve the cleavage of glycosidic linkages, breakdown of the anthocyanidin heterocycle and reconjugation of the aglycone. Information about the health effects of the bacterial metabolites in general is scarce and therefore research directed to this area is necessary.

M3 - Conference article in proceedings

SN - 952-10-1977-8

BT - Polyphenols communications 2004

A2 - Hoikkala, Antti

A2 - Soidinsalo, Otto

PB - Gummerus

CY - Jyväskylä

ER -

Aura A-M, Vainionpää M, Heinonen M, Martinez Lopez P, Santos-Buelga C, Oksman-Caldentey K-M et al. Anthocyanins and their metabolism in the in vitro gastrointestinal tract. In Hoikkala A, Soidinsalo O, editors, Polyphenols communications 2004 . Jyväskylä: Gummerus. 2004. 121