Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro

Anna-Marja Aura (Corresponding Author), K.A. O'Leary, G. Williamson, Marja Ojala, Michael Bailey, Riitta Puupponen-Pimiä, Anna-Maria Nuutila, Kirsi-Marja Oksman-Caldentey, Kaisa Poutanen

Research output: Contribution to journalArticleScientificpeer-review

219 Citations (Scopus)

Abstract

By using a batch in vitro anaerobic fecal fermentation model, we have shown that the fecal microflora can rapidly deconjugate rutin, isoquercitrin, and a mixture of quercetin glucuronides. High levels of ,D-glucosidase, ,L-rhamnosidase, and ,D-glucuronidase were present. Rutin underwent deglycosylation, ring fission, and dehydroxylation. The main metabolite, 3,4-dihydroxyphenylacetic acid, appeared rapidly (2 h) and was dehydroxylated to 3-hydroxyphenylacetic acid within 8 h. The pattern of in vitro fermentation of rutin was not changed by changing the pH (6.0 or 6.9), fermentation scale (10 or 1000 mL), or donors of the inoculum. Hydroxyphenylacetic acids were not methylated by colon flora in vitro. The colonic microflora has enormous potential to transform flavonoids into lower molecular weight phenolics, and these might have protective biological activities in the colon. The site of absorption of flavonoids and the form in which they are absorbed are critical for determining their metabolic pathway and consequent biological activities in vivo.
Original languageEnglish
Pages (from-to)1725 - 1730
JournalJournal of Agricultural and Food Chemistry
Volume50
Issue number6
DOIs
Publication statusPublished - 2002
MoE publication typeA1 Journal article-refereed

Fingerprint

Rutin
Quercetin
rutin
quercetin
Fermentation
chemical derivatives
flora
fermentation
Bioactivity
Derivatives
Flavonoids
Acids
colon
bioactive properties
acids
Colon
alpha-L-rhamnosidase
flavonoids
isoquercitrin
Glucosidases

Keywords

  • rutin
  • isoquercitrin
  • quercetin glucuronides
  • metabolism
  • deconjugation
  • ring fission
  • dehydroxylation

Cite this

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title = "Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro",
abstract = "By using a batch in vitro anaerobic fecal fermentation model, we have shown that the fecal microflora can rapidly deconjugate rutin, isoquercitrin, and a mixture of quercetin glucuronides. High levels of ,D-glucosidase, ,L-rhamnosidase, and ,D-glucuronidase were present. Rutin underwent deglycosylation, ring fission, and dehydroxylation. The main metabolite, 3,4-dihydroxyphenylacetic acid, appeared rapidly (2 h) and was dehydroxylated to 3-hydroxyphenylacetic acid within 8 h. The pattern of in vitro fermentation of rutin was not changed by changing the pH (6.0 or 6.9), fermentation scale (10 or 1000 mL), or donors of the inoculum. Hydroxyphenylacetic acids were not methylated by colon flora in vitro. The colonic microflora has enormous potential to transform flavonoids into lower molecular weight phenolics, and these might have protective biological activities in the colon. The site of absorption of flavonoids and the form in which they are absorbed are critical for determining their metabolic pathway and consequent biological activities in vivo.",
keywords = "rutin, isoquercitrin, quercetin glucuronides, metabolism, deconjugation, ring fission, dehydroxylation",
author = "Anna-Marja Aura and K.A. O'Leary and G. Williamson and Marja Ojala and Michael Bailey and Riitta Puupponen-Pimi{\"a} and Anna-Maria Nuutila and Kirsi-Marja Oksman-Caldentey and Kaisa Poutanen",
year = "2002",
doi = "10.1021/jf0108056",
language = "English",
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journal = "Journal of Agricultural and Food Chemistry",
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publisher = "American Chemical Society",
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TY - JOUR

T1 - Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro

AU - Aura, Anna-Marja

AU - O'Leary, K.A.

AU - Williamson, G.

AU - Ojala, Marja

AU - Bailey, Michael

AU - Puupponen-Pimiä, Riitta

AU - Nuutila, Anna-Maria

AU - Oksman-Caldentey, Kirsi-Marja

AU - Poutanen, Kaisa

PY - 2002

Y1 - 2002

N2 - By using a batch in vitro anaerobic fecal fermentation model, we have shown that the fecal microflora can rapidly deconjugate rutin, isoquercitrin, and a mixture of quercetin glucuronides. High levels of ,D-glucosidase, ,L-rhamnosidase, and ,D-glucuronidase were present. Rutin underwent deglycosylation, ring fission, and dehydroxylation. The main metabolite, 3,4-dihydroxyphenylacetic acid, appeared rapidly (2 h) and was dehydroxylated to 3-hydroxyphenylacetic acid within 8 h. The pattern of in vitro fermentation of rutin was not changed by changing the pH (6.0 or 6.9), fermentation scale (10 or 1000 mL), or donors of the inoculum. Hydroxyphenylacetic acids were not methylated by colon flora in vitro. The colonic microflora has enormous potential to transform flavonoids into lower molecular weight phenolics, and these might have protective biological activities in the colon. The site of absorption of flavonoids and the form in which they are absorbed are critical for determining their metabolic pathway and consequent biological activities in vivo.

AB - By using a batch in vitro anaerobic fecal fermentation model, we have shown that the fecal microflora can rapidly deconjugate rutin, isoquercitrin, and a mixture of quercetin glucuronides. High levels of ,D-glucosidase, ,L-rhamnosidase, and ,D-glucuronidase were present. Rutin underwent deglycosylation, ring fission, and dehydroxylation. The main metabolite, 3,4-dihydroxyphenylacetic acid, appeared rapidly (2 h) and was dehydroxylated to 3-hydroxyphenylacetic acid within 8 h. The pattern of in vitro fermentation of rutin was not changed by changing the pH (6.0 or 6.9), fermentation scale (10 or 1000 mL), or donors of the inoculum. Hydroxyphenylacetic acids were not methylated by colon flora in vitro. The colonic microflora has enormous potential to transform flavonoids into lower molecular weight phenolics, and these might have protective biological activities in the colon. The site of absorption of flavonoids and the form in which they are absorbed are critical for determining their metabolic pathway and consequent biological activities in vivo.

KW - rutin

KW - isoquercitrin

KW - quercetin glucuronides

KW - metabolism

KW - deconjugation

KW - ring fission

KW - dehydroxylation

U2 - 10.1021/jf0108056

DO - 10.1021/jf0108056

M3 - Article

VL - 50

SP - 1725

EP - 1730

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 6

ER -