3-epicabraleahydroxylactone and other triterpenoids from camellia oil and their inhibitory effects on Epstein-Barr virus activation

Chem Pharm Bull (Tokyo). 2004 Jan;52(1):153-6. doi: 10.1248/cpb.52.153.

Abstract

The structure of a triterpenoid isolated from the nonsaponifiable lipid (NSL) of the seed oil of the camellia (Camellia japonica L.; Theaceae) was established to be (20S)-3beta-hydroxy-25,26,27-trisnordammaran-24,20-olide (1; 3-epicabraleahydroxylactone) on the basis of spectroscopic and chemical methods. Six other triterpenoids isolated from the NSL were identified as 3-epicabraleadiol (2), ocotillol II (3), ocotillol I (4), dammarenediol II (5), (20R)-taraxastane-3beta,20-diol (6), and lupane-3beta,20-diol (7). Upon evaluation of the seven triterpenoids (1-7) with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, three compounds (5-7) showed potent inhibitory effects against EBV-EA induction (IC(50) values of 277-420 mol ratio/32 pmol TPA).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antigens, Viral / metabolism
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Camellia / chemistry*
  • Cell Line
  • Chromatography, High Pressure Liquid
  • Herpesvirus 4, Human / drug effects*
  • Humans
  • Lactones / chemistry*
  • Lactones / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Plant Oils / chemistry*
  • Plant Oils / pharmacology*
  • Tetradecanoylphorbol Acetate / pharmacology
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • 3-epicabraleahydroxylactone
  • Antigens, Viral
  • Antiviral Agents
  • Lactones
  • Plant Oils
  • Triterpenes
  • Tetradecanoylphorbol Acetate