N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols with Anti-inflammatory Activity in Lipopolysaccharide-Stimulated Macrophages Are Storage-Related Marker Compounds for Green Tea

J Agric Food Chem. 2020 Oct 28;68(43):12164-12172. doi: 10.1021/acs.jafc.0c03952. Epub 2020 Oct 19.

Abstract

Fresh green tea (GT) is commonly considered to have better sensory flavor and higher commercial value than long-term-stored GT; however, the chemical variations during storage are unclear. In this study, the chemical profiles of stored GT were surveyed among time-series samples from 0 to 19 months using a nontargeted metabolomics method. Seven N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) increased from 0.022 ± 0.019 to 3.212 ± 0.057 mg/g within 19 months (correlation coefficients with storage duration ranging from 0.936 to 0.965), and they were the most significantly increased compounds among the 127 identified compounds. Two representative EPSFs (R-EGCG-cThea and S-EGCG-cThea) possess potential anti-inflammatory properties by suppressing the expression, phosphorylation, and nuclear translocation of nuclear factor kappa-B (NF-κB) p65 in lipopolysaccharide-stimulated macrophages based on western blotting and immunofluorescence results. In conclusion, EPSFs were found to be marker compounds for stored GT and showed potential anti-inflammatory activity by regulating the NF-κB signaling pathway.

Keywords: EPSF; NF-κB signaling pathway; anti-inflammation; green tea; metabolomics; storage.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Camellia sinensis / chemistry*
  • Flavonoids / chemistry
  • Flavonoids / pharmacology*
  • Food Storage
  • Lipopolysaccharides / immunology
  • Macrophages / drug effects*
  • Macrophages / immunology
  • Mice
  • NF-kappa B / genetics
  • NF-kappa B / immunology
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Leaves
  • Pyrrolidinones / chemistry
  • Pyrrolidinones / pharmacology*
  • RAW 264.7 Cells
  • Time Factors

Substances

  • Anti-Inflammatory Agents
  • Flavonoids
  • Lipopolysaccharides
  • NF-kappa B
  • Plant Extracts
  • Pyrrolidinones
  • flavan-3-ol
  • 2-pyrrolidone