Diarylheptanoid glycosides from Zingiber officinale peel and their anti-apoptotic activity

Fitoterapia. 2022 Mar:157:105109. doi: 10.1016/j.fitote.2021.105109. Epub 2021 Dec 23.

Abstract

Four new diarylheptanoid glycosides (1-4), (1S,3R,5S)-2-(4-hydroxy-3- methoxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]-tetrahydropyran-4-ol-4'-O-β-D-glucopyranoside (1), (1S,3R,5S)-2-(4,5-dihydroxy-3-methoxyphenyl)-6-[2-(4-hydroxyphenyl) ethyl]-tetrahydropyran-4-ol-4'-O-β-D-glucopyranoside (2), (1S,3R,5S)-2-(4-hydroxy- 3,5-dimethoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-4'-O-β-D-glucopyranoside (3), and (1R,3R,5R)-2-(4-hydroxy-3,5-dimethoxyphenyl)- 6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-3-O-β-D-glucopyranoside (4) were isolated from the 50% ethanol extract of Zingiber officinale peel. The structures of the isolated compounds were determined by HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-NMR, and 2D-NMR). Compounds 1-4 significantly increased the survival rate of human normal lung bronchial epithelial cells (BEAS-2B) induced by lipopolysaccharide (LPS) at the concentration of 10 μM.

Keywords: Anti-apoptotic activity; Diarylheptanoid glycosides; Zingiber officinale peel; Zingiberaceae.

MeSH terms

  • Apoptosis / drug effects*
  • Cell Survival
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification
  • Diarylheptanoids / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Humans
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Zingiber officinale / chemistry*

Substances

  • Diarylheptanoids
  • Glycosides
  • Plant Extracts