Zephyramine. Isolated novel alkaloid from the bulbs of Zephyrantes citrina Baker

Abstract

Many plant species of the Amaryllidaceae family are used as popular medicine in the treatment of different diseases, specially as a citotoxic. Among them, several species of Zkphyrantes are used in various regions of the world. Author's research group has found in vitro cytotoxic activity in KB cells in the alcoholic extracts obtained from the bulbs of the Zephyrantes citrina Baker, collected in Caibarien, Cuba. This motivated its phytochemical study. In the present paper we report the separation and structural determination of five alkaloids isolated from this plant. The alkaloids licorine y haemanthamine (common in plants of theAmaryllidaceae family) were identified through their physical constants. spectroscopic analysis and the comparison with an authentic sample. The structure of cavinine (for the first time in the genus) was established by its physical contants and spectroscopic analysis (IR, MS and 'H-NMR). Jouberthiamine was identified by its physical constants and spectroscopic data (IR, MS); this compound belongs to the alkaloids of the Mesembrane and it is the fourth time that an alkaloid of this group is isolated in Amaryllidaceae. The structure of the new alkaloid zephyramine was established through its physical constants and spectroscopic analysis (IR, MS, 'H-NMR and uCNMR); it belongs to the ermine series without the hydroxy substituent in the ethilenic bridge, it has an oxiran ring in the C, and C 2 carbons and methoxy substituents in the A ring.