Antitumor agents, 157. Absolute structures of cumingianosides A-F, antileukemic triterpene glucosides, and structures of the hydrolysates of cumingianoside A

J Nat Prod. 1995 Apr;58(4):495-503. doi: 10.1021/np50118a003.

Abstract

The stereostructures of cumingianosides A-F, a series of triterpene glucosides with a 14,18-cycloapoeuphane skeleton, have been established by X-ray crystallographic analysis on an aglycone [1c] the acid hydrolysate of cumingianoside A [1], which is a potent cytotoxic triterpene against MOLT-4 human leukemia cells with an EC50 value of < 0.00625 microM. The 14,18-cyclopropane ring in cumingianoside A [1] was opened under acidic conditions in two different directions to give compounds with an apoeuphane skeleton and a dammarane skeleton. Furthermore, it was found that subsequent hydrolysis yielded not only an aglycone with an apoeuphane skeleton [1c] but also an apo-rearrangement product [1d].

Publication types

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

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / pharmacology
  • Humans
  • Hydrolysis
  • Leukemia, Experimental / drug therapy*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Plant Leaves / chemistry
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Glucosides
  • Triterpenes