Spirocaracolitones, CD-Spiro Triterpenoids from Ruptiliocarpon caracolito

Six CD-spiro-triterpenoids have been isolated and identified from the methylene chloride soluble extracts of the bark of Ruptiliocarpon caracolito . The structures of these compounds, named spirocaracolitones A−F, were determined by a combination of X-ray and high field NMR studies. The spirocaracolitones represent the first examples of a class of triterpenes which have a spiro system connecting rings C and D; they also carry an unusual 12-α-methyl group. It is postulated that these compounds are derived biogenetically from a friedelin derivative. Initial biological screening revealed up to 80% decreases in the rate of growth of the larvae of the European corn borer when these compounds were administered at the rate of 50 ppm in the diet.