ABSTRACT
Grayanotoxin (GTX) III, a tetracyclic diterpenoid, is the main toxic component obtained from the leaves of Leucothoe grayana MAX. In this paper, we report the correlation between toxicity and C10 stereostructure of GTX-III. 10-epi-GTX-III was derived from GTX-III in four steps. Oxidation of the GTX-II-3,6,14,16-tetraacetate with formic acid/hydrogen peroxide in chloroform gave 10,20-epoxy derivation in high yield. Reduction of the 10,20-epoxyacetate with LiAlH4 in tetrahydrofuran gave the two products, 10-epi-GTX-III and 10,20-epoxy-GTX-II. The absolute structure of the 10-epi-GTX-III was deduced from the results of X-ray crystallographic analysis. Dosage level of acute toxicity of 10-epi-GTX-III in mice was estimated at about half of natural GTX-III.
