Optically active N-acetyldopamine dimer of the crude drug 'Zentai,' the cast-off shell of the cicada, Cryptotympana sp.

Abstract

Two optically active N-acetyldopamine dimers together with four phenolic monomers were isolated from the crude drug 'Zentai,' a cast-off shell of the cicada of Cryptotympana sp. (Cicadidae). The former two were 2-(3',4'-dihydroxyphenyl)-1,4-benzodioxane derivatives carrying substituents at the 3 and 6 (or 7) positions, which are known to be components of sclerotized insect cuticles. Their structures including absolute configurations were determined on the basis of NMR and circular dichroism (CD) spectroscopic data.