The alkaloids of Nectandra megapotamica

Phytochemistry
1975.0

Abstract

The genera Nectandra and Ocotea (Lauraceae) are well represented in the Brazilian flora. They are generally characterized by the occurrence of alkaloids of the benzylisoquinoline-aporphine group [1, 2]. We now report the occurrence in a Nectandra species of indoles which have previously been associated with hallucinogenic preparations from, for example, Piptadenia (Leguminosae) [3,4] Banisteriopsis (Malpighiaceae) [5, 6] and Virola (Myristicaceae) [7] species. The bark of Nectandra megapotamica (Sprg.) Chodat et Hassler, a tree of medium height growing in the north-east of S. Paulo state, is popularly attributed with the property of relieving pain [8]. A chemical and pharmacological investigation was therefore undertaken. Two strong bases were isolated and shown to be indoles by UV spectrometry. One was identified as N-methyltryptamine (1). The other was identified by IR, UV and NMR spectroscopy and mass spectrometry as 6-methoxy-N-methyl-1,2,3,4-tetrahydro-β-carboline (2). Comparison with authentic samples [9] confirmed the identity. Both alkaloids 1 and 2 inhibit the growth of Crithidia fasciculata (Trypanosomatidae) in brain heart infusion hemin medium at 6 μg/ml. It is not yet known whether this activity is related to the previously reported pharmacological properties of the bases [5, 10].

Knowledge Graph

Similar Paper