In vitro antioxidative activity of ( - )-epicatechin glucuronide metabolites present in human and rat plasma

Midori Natsume, Naomi Osakabe, Akiko Yasuda, Seigo Baba, Takashi Tokunaga, Kazuo Kondo, Toshihiko Osawa, Junji Terao

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Recently we identified four conjugated glucuronide metabolites of epicatechin, (-)-epicatechin-3′-O-glucuronide (E3′G), 4′-O-methyl-(-)-epicatechin-3′-O-glucuronide (4′ ME3′G), (-)-epicatechin-7-O-glucuronide (E7G) and 3′-O-methyl-(-)-epicatechin-7-O-glucuronide (3′ME7G) from plasma and urine. E3′G and 4′ME3′G were isolated from human urine, while E7G and 3′ME7G were isolated from rats that had received oral administration of (-)-epicatechin (Natsume et al. (2003), Free Radic. Biol. Med. 34, 840-849). It has been suggested that these metabolites possess considerable in vivo activity, and therefore we carried out a study to compare the antioxidant activities of the metabolites with that of the parent compound. This was achieved by measuring superoxide scavenging activity, reduction of plasma TBARS production and reduced susceptibility of low-density-lipoprotein (LDL) to oxidation. (-)-Epicatechin was found to have more potent antioxidant activity than the conjugated glucuronide metabolites. Both (- -epicatechin and E7G had marked antioxidative properties with respect to superoxide radical scavenging activity, plasma oxidation induced by 2,2′-azobis-(2-aminopropane) dihydrochloride (AAPH) and LDL oxidation induced by copper ions or 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (MeO-AMVN). In contrast, the other metabolites had light antioxidative activities over the range of physiological concentrations found in plasma.

Original languageEnglish
Pages (from-to)1341-1348
Number of pages8
JournalFree Radical Research
Volume38
Issue number12
DOIs
Publication statusPublished - 2004 Dec
Externally publishedYes

Fingerprint

Catechin
Metabolites
Rats
Glucuronides
Plasmas
Scavenging
LDL Lipoproteins
Superoxides
Oxidation
Antioxidants
epicatechin-glucuronide
Plasma sources
Copper
Thermodynamic properties
Ions

Keywords

  • ( - )-epicatechin metabolites
  • Antioxidative activity
  • Low-density-lipoprotein(LDL)
  • Plasma oxidation
  • Superoxide radical

ASJC Scopus subject areas

  • Biochemistry

Cite this

In vitro antioxidative activity of ( - )-epicatechin glucuronide metabolites present in human and rat plasma. / Natsume, Midori; Osakabe, Naomi; Yasuda, Akiko; Baba, Seigo; Tokunaga, Takashi; Kondo, Kazuo; Osawa, Toshihiko; Terao, Junji.

In: Free Radical Research, Vol. 38, No. 12, 12.2004, p. 1341-1348.

Research output: Contribution to journalArticle

Natsume, Midori ; Osakabe, Naomi ; Yasuda, Akiko ; Baba, Seigo ; Tokunaga, Takashi ; Kondo, Kazuo ; Osawa, Toshihiko ; Terao, Junji. / In vitro antioxidative activity of ( - )-epicatechin glucuronide metabolites present in human and rat plasma. In: Free Radical Research. 2004 ; Vol. 38, No. 12. pp. 1341-1348.
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AU - Natsume, Midori

AU - Osakabe, Naomi

AU - Yasuda, Akiko

AU - Baba, Seigo

AU - Tokunaga, Takashi

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AU - Osawa, Toshihiko

AU - Terao, Junji

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