Solandelactones A-I, lactonized cyclopropyl oxylipins isolated from the hydroid Solanderia secunda

Abstract

Solandelactones A-I(1-9), cyclopropyl and lactone containing novel docosanoids have been isolated from the hydroid Solanderia secunda. The structure of these compounds have been elucidated by combined spectral and chemical studies. Configuration of the cyclopropyl ring has been essigned as the opposite of related oxylipins by NOESY experiments. Absolute stereochemistry has been determined on the basis of chemical transformations and CD measurements of synthetic derivatives. In addition, the biogenetic origin of solandelactones has been discussed. Solandelactones C, D and G exhibited moderate inhibitory activity against Farnesyl Protein Transferase.