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o-Quinone trapping by stilbenoids.

Rosario Zamora1, Francisco J Hidalgo1

  • 1Instituto de la Grasa, CSIC, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.

Food Chemistry
|April 25, 2025
PubMed
Summary
This summary is machine-generated.

Stilbenoids like resveratrol can trap o-quinones, forming dihydrobenzodioxins and dihydrobenzofuranols. These adducts form rapidly under mild conditions, with dihydrobenzodioxins produced more readily.

Keywords:
3-Hydroxytyrosol (PubChem ID: 82755)4-Methylcatechol (PubChem ID: 9958)Carbonyl-amine reactionsCarbonyl-phenol reactionsFood carbonylomeO-QuinonesPiceatannol (PubChem ID: 667639)Pterostilbene (PubChem ID: 5281727)Reactive carbonylsResveratrol (PubChem ID: 445154)Stilbenoids

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Area of Science:

  • Natural Products Chemistry
  • Organic Reaction Mechanisms
  • Spectroscopic Analysis

Background:

  • Stilbenoids, including resveratrol, pterostilbene, and piceatannol, are natural compounds with potential biological activities.
  • o-Quinones are reactive species implicated in various biological processes and oxidative stress.
  • Understanding the interactions between stilbenoids and o-quinones is crucial for elucidating their biochemical roles.

Purpose of the Study:

  • To investigate the reactivity of stilbenoids with o-quinones.
  • To characterize the adducts formed from these reactions.
  • To elucidate the reaction mechanism and factors influencing adduct formation.

Main Methods:

  • Reaction of selected stilbenoids (resveratrol, pterostilbene, piceatannol) with o-quinones (4-methylcatechol quinone, hydroxytyrosol quinone).
  • Isolation and purification of reaction products.
  • Structural characterization using one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS).

Main Results:

  • Two types of adducts were identified: dihydrobenzo[b][1,4]dioxins (1) and dihydrobenzofuran-7-ols (2).
  • Adducts formed rapidly at low/room temperature and neutral/slightly acidic pH via reaction at the stilbenoid's ethene linker.
  • Dihydrobenzodioxins (1) were produced in higher yields than dihydrobenzofuran-7-ols (2), despite similar activation energies.
  • A zwitterionic intermediate mechanism was proposed to explain the limited isomer formation.

Conclusions:

  • Stilbenoids effectively trap o-quinones through addition reactions.
  • The reaction pathway favors the formation of dihydrobenzodioxin adducts.
  • The study provides insights into the chemical interactions between stilbenoids and quinones, relevant to their biological functions.