Antitumor Agents, 157. Absolute Structures of Cumingianosides A-F, Antileukemic Triterpene Glucosides, and Structures of the Hydrolysates of Cumingianoside A

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].