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

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].

• Authors: Y Kashiwada, T Fujioka, K Mihashi, N Marubayashi, K Mizuki, I S Chen, K H Lee
• Journal: Journal of natural products (J Nat Prod) Vol. 58 Issue 4 Pg. 495-503 (Apr 1995) ISSN: 0163-3864 [Print] United States
• PMID: 7623027 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents, Phytogenic
• Glucosides
• Triterpenes

Topics

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