Flavonoids and linderone from Lindera oxyphylla and their bioactivities

Comb Chem High Throughput Screen. 2013 Feb;16(2):160-6.

Abstract

A new linderone A, namely 2-cinnamoyl-3-hydroxy-4, 5-dimethoxycyclopenta-2, 4-dienone (5), together with three known flavonoids (1-3) and one linderone (4), were isolated from the bark of Lindera oxyphylla. Extensive spectroscopic analysis including 1D and 2D-NMR spectra determined their sturctures. In addition, the antioxidant activity of all the compounds has been determined using 2, 2-diphenyl-1-picrylhydrazyl radical scavenging (DPPH), ferric reducing antioxidant power (FRAP) and ferrous ion chelating (FIC) methods. Compound 3 showed excellent DPPH scavenging activity with IC50% value of 8.5 ± 0.004% (μg/mL) which is comparable with vitamin C. This compound, also showed an absorbance value of 1.00 ± 0.06% through FRAP test when compared with Butyl Hydroxy Aniline (BHA). However, FIC showed low activity for all the isolated compounds (chelating activity less than 50%) in comparison with ethylene diamine tetra acetic acid (EDTA). Anticancer activity for all compounds has also been measured on A375 human melanoma, HT-29 colon adenocarcinoma, MCF-7 human breast adenocarcinoma cells, WRL-68 normal hepatic cells, A549 non-small cell lung cancer cells and PC-3 prostate adenocarcinoma cell line. Compound 1 showed A549=65.03%, PC-3=30.12%, MCF-7=47.67, compound 2 showed PC-3=90.13%, compound 3 showed MCF-7=79.57 and for compound 5 MCF-7 is 96.33.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Biphenyl Compounds / chemistry
  • Cell Line
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chelating Agents / chemistry
  • Chelating Agents / pharmacology
  • Flavonoids / chemistry*
  • Flavonoids / pharmacology
  • Free Radicals / chemistry
  • Humans
  • Lindera / chemistry*
  • Neoplasms / drug therapy
  • Picrates / chemistry

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Biphenyl Compounds
  • Chelating Agents
  • Flavonoids
  • Free Radicals
  • Picrates
  • linderone A
  • 1,1-diphenyl-2-picrylhydrazyl