GB948485A - New alkaloids and other new compounds from holarrhena species and processes for obtaining the same - Google Patents

Abstract

The invention comprises three steroidal alkaloids isolated from the crushed leaves and/or inflorescences of plants of the genus Holarrhena, species Africana and Floribunda, viz. "Alkaloid C" or Holaphylline, (D5-3b-methylamino-20-oxopregnene), "Alkaloid D" or Holaphyllamine, (D5-3b-amino -20- oxopregnane), and "Alkaloid E" or Holamine, (D5-3a-amino -20- oxopregnene) together with a process for their isolation and also that of "Alkaloid B" or Togholamine (6-amino -7- [g, g-dimethylallyl]-purine) by subjecting the crushed leaves and/or inflorescences of plants of the species H. africana or H. floribunda to an extraction treatment to remove chlorophyll, rubbers, triterpenic and tannic acids, Principle A, and especially ursolic acid, and then separating the alkaloids B, C, D and E successively from the residue, preferably by taking it up in a dry benzene, crystallising out "Alkaloid B", and subjecting the mother liquor to chromatography on alumina. The preliminary extraction treatment preferably comprises the steps of (i) percolating the crushed leaves with an acidified alcohol, chloroform, or ethanol, (ii) evaporating the solvent and adding water to the residue, (iii) separating the chlorophyll, the resins and rubber which the insoluble constituents, (iv) rendering the filtrate alkaline, (v) extracting with a water-immiscible solvent, (vi) evaporating the solvent from the extract and washing the alkaloid bases thus obtained with petroleum ether. "Principle A" has a m.pt. 245 DEG C., is inert to mercuric iodide reagent, and is capable of reacting well in the Liebermann nitroso reaction. The invention also relates to a process for the production of progesterone by deamination of alkaloid "C", "D", or "E" with either hypochlorous acid or N-chlorosuccinimide. Detailed examples are given. The steroidal alkaloids exhibit psychotonic, psycholeptic and/or anti-inflammatory activity.