New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum

Planta Med. 2007 May;73(5):484-90. doi: 10.1055/s-2007-967189. Epub 2007 Apr 26.

Abstract

Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3 beta-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7 R,8 S)-9-O-beta-D-xylopyranosyl-9'-O-alpha- L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7 R,8 S)-9-O-shikimoyl-4-O-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8- O-4' neolignan glycoside, (7 S,8 R)-1-[4-O-(beta-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30% and 9.30% at 1.0 x 10(-5) M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0% and 51.0% at 1.0 x 10(-5) M, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Cells, Cultured
  • Chemical Fractionation
  • Chromatography
  • Fruit / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Illicium / chemistry*
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Mice
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Glycosides
  • Lactones
  • Lignans
  • Plant Extracts
  • Sesquiterpenes