Sciaferine and N-Formylanolobine, Two New Aporphine Alkaloids from the Neutral Fraction of Sciadotenia toxifera

HETEROCYCLES
1999.0

Abstract

The structures of sciaferine (1), a new oxoaporphine alkaloid, and N-formylanolobine (2), both isolated from the neutral fraction of Sciadotenia toxifera, were determined by spectral methods. Sciadotenia toxifera (Krukoff and A. C. Smith), a Peruvian Menispermaceae plant, has been used in folk medicine for the treatment of sterility and malaria as well as an ingredient of curare. Seven bishenzylisoquinolines, (+)-xiadenine, (+)-sciadoline, (+)-sciadoferine, (+) and (-)-isochondodendrines, (+)-O,O'-dimethylcurine, and epi-norcycleanine, are the only compounds isolated and identified from the total bases of this species. Even though the neutral fraction was not found to contain any antitumor activity, we decided to investigate this fraction in search of new alkaloids. Apart from the typical sterols, trans-stigmasterol, and a variety of sphingolipids, two new minor alkaloids, sciaferine (1) and N-formylanolobine (2), were isolated after repeated column chromatography and preparative TLC followed by crystallization.

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