Abstract
Roemeria hybrida (L.) DC. (Papaveraceae) of Turkish origin has yielded the new prosporphine alkaloids (-)-roemerialinone ( 3), (-)-isoorientalinone ( 4), (-)-isoroemerialinone ( 5), (-)- 11,12-dihydroorientalinone ( 6), (+)-8, 9-dihydroisoroemerialinone ( 9) and (-)-α-roemehybrine ( 11). Catalytic reduction of (-)-isoorientalinone ( 4) led to (+)-8, 9-dihydroisoorientalinone ( 8) which corresponds to the partly characterized “(+)-dihydroorientalinone” originally obtained from Papaver orientale. The previously known (-)-roehybrine ( 10) of undetermined structure was also reisolated, and its structure was elucidated. Known proaporphines present are (-)-mecambrine ( 1) and (-)-orientalinone ( 2). The isolation of such pairs of diastereomeric proaporphines as 2 and 4, and 3 and 5, points to the fact that enzyme catalyzed intramolecular oxidative coupling of a specific tetraoxygenated tetrahydrobenzylisoquinoline may occur in either of two modes, depending upon the folding of the pendant benzylic ring.
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