Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin

Differences between human and rat

Midori Natsume, Naomi Osakabe, Makoto Oyama, Motoko Sasaki, Seigo Baba, Yoshimasa Nakamura, Toshihiko Osawa, Junji Terao

Research output: Contribution to journalArticle

181 Citations (Scopus)

Abstract

(-)-Epicatechin is one of the most potent antioxidants present in the human diet. Particularly high levels are found in black tea, apples, and chocolate. High intake of catechins has been associated with reduced risk of cardiovascular diseases. There have been several reports concerning the bioavailability of catechins, however, the chemical structure of (-)-epicatechin metabolites in blood, tissues, and urine remains unclear. In the present study, we purified and elucidated the chemical structure of (-)-epicatechin metabolites in human and rat urine after oral administration. Three metabolites were purified from human urine including (-)-epicatechin-3′-O-glucuronide, 4′-O-methyl-(-)-epicatechin-3′-O-glucuronide, and 4′-O-methyl-(-)-epicatechin-5 or 7-O-glucuronide, according to 1H- and 13C-NMR, HMBC, and LC-MS analyses. The metabolites purified from rat urine were 3′-O-methyl-(-)-epicatechin, (-)-epicatechin-7-O-glucuronide, and 3′-O-methyl-(-)-epicatechin-7-O-glucuronide. These compounds were also detected in the blood of humans and rats by LC-MS. The presence of these metabolites in blood and urine suggests that catechins are metabolized and circulated in the body after administration of catechin-containing foods.

Original languageEnglish
Pages (from-to)840-849
Number of pages10
JournalFree Radical Biology and Medicine
Volume34
Issue number7
DOIs
Publication statusPublished - 2003 Apr 1
Externally publishedYes

Fingerprint

Catechin
Rats
Plasmas
Metabolites
Glucuronides
Blood
epicatechin-glucuronide
Nutrition
Antioxidants
Nuclear magnetic resonance
Tissue

Keywords

  • (-)-Epicatechin
  • Free radicals
  • Glucuronidation
  • Human
  • Metabolites
  • Rat

ASJC Scopus subject areas

  • Medicine(all)
  • Toxicology
  • Clinical Biochemistry

Cite this

Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin : Differences between human and rat. / Natsume, Midori; Osakabe, Naomi; Oyama, Makoto; Sasaki, Motoko; Baba, Seigo; Nakamura, Yoshimasa; Osawa, Toshihiko; Terao, Junji.

In: Free Radical Biology and Medicine, Vol. 34, No. 7, 01.04.2003, p. 840-849.

Research output: Contribution to journalArticle

Natsume, Midori ; Osakabe, Naomi ; Oyama, Makoto ; Sasaki, Motoko ; Baba, Seigo ; Nakamura, Yoshimasa ; Osawa, Toshihiko ; Terao, Junji. / Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin : Differences between human and rat. In: Free Radical Biology and Medicine. 2003 ; Vol. 34, No. 7. pp. 840-849.
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