Inhibitory effects of cucurbitane glycosides and other triterpenoids from the fruit of Momordica grosvenori on epstein-barr virus early antigen induced by tumor promoter 12-O-tetradecanoylphorbol-13-acetate

J Agric Food Chem. 2002 Nov 6;50(23):6710-5. doi: 10.1021/jf0206320.

Abstract

Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5alpha,6alpha-epoxymogroside IE(1) (8) and 11-oxomogroside A(1) (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4-6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10-19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E(1) (12) was a new naturally occurring compound. Eighteen triterpenoids (2-19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated 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, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70-100% inhibition at 1 x 10(3) mol ratio/TPA).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, Viral / biosynthesis
  • Antigens, Viral / drug effects*
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Fruit / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Momordica / chemistry*
  • Tetradecanoylphorbol Acetate / pharmacology*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • 11-oxomogroside A
  • 5,6-epoxymogroside IE
  • Antigens, Viral
  • Epstein-Barr virus early antigen
  • Glycosides
  • Triterpenes
  • karounidiol dibenzoate
  • karounidiol
  • Tetradecanoylphorbol Acetate