In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol

Satu Heinonen, Tarja Nurmi, Kirsi Liukkonen, Kaisa Poutanen (Corresponding Author), Kristiina Wähälä, Takeshi Deyama, Sansei Nishibe, Herman Adlercreutz (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

376 Citations (Scopus)

Abstract

The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented.
Original languageEnglish
Pages (from-to)3178-3186
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume49
Issue number7
DOIs
Publication statusPublished - 2001
MoE publication typeA1 Journal article-refereed

Fingerprint

Lignans
lignans
Metabolism
metabolism
matairesinol
Metabolites
metabolites
2,3-bis(3'-hydroxybenzyl)butyrolactone
2,3-bis(3'-hydroxybenzyl)butane-1,4-diol
In Vitro Techniques
electrodes
Spectrometry
detectors
spectroscopy
Spectrum Analysis
Electrodes
chemical derivatives
Gases
High Pressure Liquid Chromatography
gases

Keywords

  • Phytoestrogens
  • lignans
  • matairesinol
  • secoisolariciresinol
  • lariciresinol
  • pinoresinol
  • syringaresinol
  • isolariciresinol
  • arctigenin
  • 7-hydroxymatairesinol
  • mammalian lignans
  • enterolactone
  • enterodiol

Cite this

Heinonen, Satu ; Nurmi, Tarja ; Liukkonen, Kirsi ; Poutanen, Kaisa ; Wähälä, Kristiina ; Deyama, Takeshi ; Nishibe, Sansei ; Adlercreutz, Herman. / In vitro metabolism of plant lignans : New precursors of mammalian lignans enterolactone and enterodiol. In: Journal of Agricultural and Food Chemistry. 2001 ; Vol. 49, No. 7. pp. 3178-3186.
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abstract = "The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented.",
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year = "2001",
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Heinonen, S, Nurmi, T, Liukkonen, K, Poutanen, K, Wähälä, K, Deyama, T, Nishibe, S & Adlercreutz, H 2001, 'In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol', Journal of Agricultural and Food Chemistry, vol. 49, no. 7, pp. 3178-3186. https://doi.org/10.1021/jf010038a

In vitro metabolism of plant lignans : New precursors of mammalian lignans enterolactone and enterodiol. / Heinonen, Satu; Nurmi, Tarja; Liukkonen, Kirsi; Poutanen, Kaisa (Corresponding Author); Wähälä, Kristiina; Deyama, Takeshi; Nishibe, Sansei; Adlercreutz, Herman (Corresponding Author).

In: Journal of Agricultural and Food Chemistry, Vol. 49, No. 7, 2001, p. 3178-3186.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - In vitro metabolism of plant lignans

T2 - New precursors of mammalian lignans enterolactone and enterodiol

AU - Heinonen, Satu

AU - Nurmi, Tarja

AU - Liukkonen, Kirsi

AU - Poutanen, Kaisa

AU - Wähälä, Kristiina

AU - Deyama, Takeshi

AU - Nishibe, Sansei

AU - Adlercreutz, Herman

PY - 2001

Y1 - 2001

N2 - The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented.

AB - The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented.

KW - Phytoestrogens

KW - lignans

KW - matairesinol

KW - secoisolariciresinol

KW - lariciresinol

KW - pinoresinol

KW - syringaresinol

KW - isolariciresinol

KW - arctigenin

KW - 7-hydroxymatairesinol

KW - mammalian lignans

KW - enterolactone

KW - enterodiol

U2 - 10.1021/jf010038a

DO - 10.1021/jf010038a

M3 - Article

VL - 49

SP - 3178

EP - 3186

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 7

ER -