Isolation and structural elucidation of two new alkaloids from papaver macrostomum boiss. Et huet

Tetrahedron Letters
1974.0

Abstract

The plant Papaver macrostomum Boiss. et Huet was found to contain two new alkaloids which were named sevanine and macrostomine. Sevanine, obtained from the phenolic fraction (m.p. 218°), showed M+ at mass 309.0980 corresponding to C18H15NO4. Its UV spectrum was practically identical with that of papaverine, and PMR spectrum (CDCl3) indicated methoxyl, benzylic, methylenedioxy, and aromatic protons, leading to the structure 1-(3,4-methylenedioxybenzyl)-6,7-hydroxymethoxyisoquinoline (I). Chromatography on alumina of the nonquaternary fraction gave macrostomine (m.p. 107-110°, [α]D25 -51° ± 3°), with M+ 406.1892 corresponding to C24H28N2O4. Its UV spectrum was similar to that of sevanine, and PMR spectrum (C6D6) showed N-CH3, pyrrolidine moiety, methoxyl, methylenedioxy, benzylic, and aromatic protons, leading to structure II. The negative longest wavelength Cotton effect of macrostomine, similar to (S)-(-)-nicotine or (S)-(-)-brevicolllne, suggested its configuration may be S.

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