Antioxidant constituents and a new triterpenoid glycoside from Flos Lonicerae

Arch Pharm Res. 2007 Jan;30(1):1-7. doi: 10.1007/BF02977770.

Abstract

As a component of our continuing investigations into herb-derived antioxidant agents, we have evaluated the antioxidant effects of Flos Lonicerae (Lonicera japonica flowers), via 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, total reactive oxygen species (ROS), hydroxyl radical (*OH), and peroxynitrite (ONOO-) assays. Among the methanolic extract and the dichloromethane, ethyl acetate, n-butanol, and water fractions, the EtOAc fraction of Flos Lonicerae exhibited marked scavenging/inhibitory activities, as follows: IC50 values of 4.37, 27.58 +/- 0.71, 0.47 +/- 0.05, and 12.13 +/- 0.79 microg/mL in the DPPH, total ROS, ONOO-, and *OH assays, respectively. Via a bioactivity-guided fractionation approach, a new triterpenoid glycoside, oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-xylopyranosyl(1-->6)]-beta-D-glucopyranosyl ester (12), along with eleven known compounds, including chrysoeriol (1), luteolin (2), 5-hydroxymethyl-2-furfural (3), caffeic acid (4), protocatechuic acid (5), chrysoeriol 7-O-beta-D-glucopyranoside (6), isorhamnetin 3-O-beta-D-glucopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), quercetin 3-O-beta-D-glucopyranoside (9), hederagenin 3-O-alpha-L-arabinopyranoside (10), and luteolin 7-O-beta-D-glucopyranoside (11), were isolated from the EtOAc fraction. The structures of isolated compounds 1-12 were elucidated via spectroscopic analyses. Compound 12 was isolated from a natural source for the first time. Compounds 2, 4, 5, 7, 9, and 11 evidenced marked scavenging activities, with IC50 values of 2.08-11.76 microM for DPPH radicals, and 1.47-6.98 microM for ONOO-.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemistry
  • Biphenyl Compounds
  • Chromatography, Thin Layer
  • Flowers
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / pharmacology
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Hydroxyl Radical / chemistry
  • In Vitro Techniques
  • Kidney / drug effects
  • Kidney / metabolism
  • Lonicera*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mass Spectrometry
  • Molecular Structure
  • Peroxynitrous Acid / chemistry
  • Picrates / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Rats
  • Rats, Wistar
  • Reactive Oxygen Species / metabolism
  • Solvents / chemistry
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Glycosides
  • Picrates
  • Plant Extracts
  • Reactive Oxygen Species
  • Solvents
  • Triterpenes
  • Peroxynitrous Acid
  • Hydroxyl Radical
  • 1,1-diphenyl-2-picrylhydrazyl