THE STRUCTURES OF TWO NEW ALKALOIDS: CHASMACONITINE AND CHASMANTHININE

Abstract

A re-examination of the root of Aconitumchasmanthum Stapf has shown that it contains several alkaloids. Of these, besides indaconitine, the presence of which had been reported long ago, four new alkaloids have been isolated: base A (C26H43O6N), base B (C25H41O6N), chasmaconitine (C34H47O9N), and chasmanthinine (C36H49O9N). Chasmaconitine gives rise to bikhaconine on hydrolysis, and has been shown by conversion to delphinine to be N-ethyl-N-desmethyl-delphinine. Chasmanthinine is also hydrolyzable to bikhaconine. Whereas in chasmaconitine bikhaconine is esterified with acetic and benzoic acid, in chasmanthinine it is esterified with acetic and trans-cinnamic acid. The complete structures and absolute configurations of both bases are derived.