Synthesis, analytical features, and biological relevance of 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactone, a microbial metabolite derived from the catabolism of dietary flavan-3-ols

Fernando Sánchez-Patán, Mourad Chioua, Ignacio Garrido, Carolina Cueva, Abdelouahid Samadi, José Marco-Contelles, M. Victoria Moreno-Arribas, Begoña Bartolomé, Maria Monagas

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

The physiological significance of 5-(3′,4′-dihydroxyphenyl)- γ-valerolactone, an important metabolite derived from the catabolism of flavan-3-ols by gut microbiota, has been often overlooked due to the lack of the commercial standard. In the present work, this metabolite has been chemically synthesized, and its analytical parameters and antioxidant capacity have been determined in comparison to other chemical analogues [isomer 3-(3′,4′-dihydroxyphenyl)-δ-valerolactone and γ-valerolactone] and other structurally related compounds [(+)-catechin, (-)-epicatechin, and 3-(3,4-dihydroxyphenyl)-propionic acid]. The synthesized compound was also used to perform a targeted analysis in samples collected during the in vitro fermentation of a grape seed flavan-3-ol extract with human fecal microbiota from three healthy volunteers. The time-course formation of 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone revealed large interindividual differences among volunteers, with concentrations ranging from 3.31 to 77.54 μM at 10 h of fermentation. These results are further discussed in view of the scarce reports quantifying 5-(3′,4′-dihydroxyphenyl) -γ-valerolactone in in vitro fermentation studies, and pharmacokinetic and intervention studies.

Original languageEnglish
Pages (from-to)7083-7091
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume59
Issue number13
DOIs
Publication statusPublished - Jul 13 2011
Externally publishedYes

Keywords

  • 3-(3′,4′-dihydroxyphenyl)-δ-valerolactone
  • 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone
  • Flavan-3-ols
  • gut microbiota
  • γ- valerolactone

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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