Acutumine is a minor alkaloids' from Sinomenium acutum REND. et WILE. (Japanese name; Oh-tsuzurafuji), a Menispermaceous plant, and its structure has long been unknown. Recently, we isolated acutumine from the same plant along with the N-nor base, for which we proposed the name acutumidine. Both alkaloids were also isolated from Menispermum dauricum DC. (Japanese name: Kohmori-kazura).In early stage of the investigation, acutumine was reported to have the molecular formula C20H27N08 or C21H27NO8.1' After careful reexamination, however, we found that acutumine has a chlorine atom in the molecule and proposed the revised formula C19H24NO6C1 for acutumine.2' Acutumidine, m.p. 239-241° (decomp.), pKa 6.6 (50% EtOH), [a]D-212° (pyridine), has a molecular formula C18H22NO6C1 and shows closely similarity to acutumine in spectral properties. The interrelationship between them was established by the conversion of the former to the latter by N-methylation.Presence of three partial structures (I, II, and III) in these alkaloids are deduced on the basis of experimental evidences previously reported2' and additional findings which will be discussed in the following sections.
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