Seven New Aporphine-Benzylisoquinoline Alkaloids from Thalictrum cultratum

Journal of Natural Products
1986.0

Abstract

Thalictrum cultratum (Ranunculaceae), of Pakistani origin, has yielded the new aporphine-benzylisoquinolines (+)-thalibulamine (1), (+)-thalifaronine (3), (+)-thalifaramine (4), (+)-thalifaretine (5), (+)-thalifaricine (6), (+)-thalifarazine (7), and (+)-thalifaroline (9). Some trends concerning the structural features and stereochemistry of Thalictrum aporphine-benzylisoquinoline dimers have been noted. The aporphine-benzylisoquinolines of Thalictrum species (Ranunculaceae) fall within five distinct subgroups denoted by the prototype alkaloids (+)-thalicarpine, (+)-fetidine, (+)-istanbulamine, (+)-thalifaberine, and (+)-uskudaramine (1). The classification is based upon the nature of the tetrahydrobenzylisoquinoline moiety involved, which may belong either to the S-reticuline or the S-coclaurine series, as well as upon the type and position of the bonding connecting the two halves of the dimer. An added idiosyncrasy of Thalictrum isoquinoline alkaloids is their marked tendency to incorporate extra oxygenation at the two top aromatic rings, specifically at C-3 of the aporphine and at C-5' of the tetrahydrobenzylisoquinoline (2). As a result of the study of the alkaloidal content of Thalictrum cultratum Wall. (3,4), we now report the isolation of twelve aporphine-benzylisoquinoline dimers, of which seven are new. One of the new dimers belongs to the (+)-istanbulamine series, while the six others are related to (+)-thalifaberine.

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