Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from .

Two unusual phenanthrene derivatives related to aporphine alkaloids, artapilosines A () and B (), as well as two biogenetically related known aporphine alkaloids, (-)-anonaine () and (-)--acetylanonaine (), were separated and purified from . Artapilosine A () is the first compound representative of a new class of phenanthrene derivatives having an unprecedented carbon skeleton, in which the six-membered nitrogen-containing heterocyclic structure in a typical aporphine alkaloid was substituted with a unique five-membered carbocyclic ring. This is the first report of the formation of a carbon-carbon bond between C-5 and C-6a in with the loss of the nitrogen atom N-6 in the classic aporphine alkaloid.