Antioxidant lignans and chromone glycosides from Eurya japonica

J Nat Prod. 2013 Apr 26;76(4):580-7. doi: 10.1021/np3007638. Epub 2013 Mar 29.

Abstract

Four new 8,8',7,2'-lignans, (+)-ovafolinin B-9'-O-β-d-glucopyranoside (1), (-)-ovafolinin B-9'-O-β-d-glucopyranoside (2), (+)-ovafolinin E-9'-O-β-d-glucopyranoside (3), and (-)-ovafolinin E-9'-O-β-d-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5'-trimethoxy-4',7-epoxy-8,3'-neolignan-9,9'-diol-4-O-β-d-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-glucopyranoside (7) and 5,7-dihydroxy-4H-chromen-4-one-3-O-β-d-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 μM for 1) demonstrated potent antioxidant activity compared to the positive control α-tocopherol (ED50 27.21 μM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / pharmacology
  • Chromones / chemistry
  • Chromones / isolation & purification*
  • Chromones / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology*
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Picrates / pharmacology
  • Plant Stems / chemistry
  • Quercetin / pharmacology
  • Stereoisomerism
  • Taiwan
  • Theaceae / chemistry*
  • alpha-Tocopherol / pharmacology

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Chromones
  • Glycosides
  • Lignans
  • Picrates
  • Nitric Oxide
  • Quercetin
  • 1,1-diphenyl-2-picrylhydrazyl
  • alpha-Tocopherol