Dehydroipomeamarone as an Intermediate in the Biosynthesis of Ipomeamarone, a Phytoalexin from Sweet Potato Root Infected with Ceratocystis fimbriata.

Recently, we isolated dehydroipomeamarone, a new sesquiterpenoid from sweet potato (Ipomoea batatas Lam.) root tissue infected with Ceratocystis fimbriata (Ell. et Halst.). The purpose of this investigation was to determine whether dehydroipomeamarone was a precursor in the biosynthetic pathway of ipomeamarone. The incorporation of acetate-2-(14)C into ipomeamarone was markedly inhibited by the presence of dehydroipomeamarone. Radioactive dehydroipomeamarone was efficiently converted into ipomeamarone, and the compound was biosynthesized earlier than ipomeamarone according to a time course analysis of the production of the terpenoid. These results support the notion that dehydroipomeamarone is an immediate precursor of ipomeamarone. On the other hand, the production of ipomeamarone was slightly lessened in the presence of dehydroipomeamarone. Thus, the marked reduction of acetate-2-(14)C incorporation into ipomeamarone by dehydroipomeamarone may result from both isotopic dilution and an inhibitory effect by exogenous dehydroipomeamarone.