A chemical investigation of Veratrum fimbriatum Gray has yielded two new hypotensively active germine esters, germanitrine (C39H59O11N), and germinitrine (C39H87O11N), as well as neogermitrine, jervine and pseudojervine. In addition, the alkaloidal ester, veratroylzygadenine, previously isolated from Zygadenus venenosus Wats was found to be present in this species of veratrum.On hydrolysis, the triester germanitrine affords germine, acetic acid, tiglic acid and (l)-a-methylbutyric acid. On methanolysis, germanitrine readily loses a labile acetyl group yielding germanidine (C37HS7O10N). The hydrolysis of the triester germinitrine, yielded germine, acetic acid, tiglic acid and angelic acid.Germanitrine and germinitrine,1 two new hypotensively active germine ester alkaloids, have been isolated from the hitherto uninvestigated species, Veratrum fimbriatum Gray. In addition, the isolation procedure yielded the known veratrum alkaloids, neogermitrine, jervine and pseudojervine, as well as veratroylzygadenine, an ester alkaloid previously isolated from Zygadenus venenosus Wats.3The extraction procedure employed in this investigation was essentially the same as that reported previously in our work on Veratrum viride Ait.4 The total "amorphous bases'' thus obtained were subjected to a preliminary fractionation by an 8plate countercurrent distribution using benzene-2 M acetate buffer pH 5.5 as the solvent system. The results of the distribution showed the largest portion of the material to be in tubes 0-1 with the remainder distributed fairly evenly in the other tubes. Pharmacological screening5 for hypotensive activity revealed high activity in tubes 0-1 and tubes 2-5.The material recovered from tubes 0-1 was redistributed on a 24-plate countercurrent machine with 0.5 N sodium acetate buffer pH 5.0-benzenecyclohexane 40:60 as the solvent system. On careful fractional crystallization of the material recovered from tubes 4-14 from acetone-water, two new alkaloids were obtained which after characterization were named germanitrine and germinitrine. Alkaline hydrolysis of germanitrine yielded germine, acetic acid, (Z) -a-methylbutyric acid and tiglic acid. On the basis of the analytical data and the hydrolysis products the empirical formula C39H59O11N was established. On methanolysis, germanitrine was converted to a diester, germanidine (C37H57O10N), by the loss of the labile acetyl group.Alkaline hydrolysis of germinitrine afforded germine, acetic acid, tiglic acid and angelic acid. On the basis of the analytical data and the hydrolysis products, the empirical formula C39H57O11N was established.Germanitrine and germinitrine represent the (1) A preliminary report on this investigation appeared in a previous communication.2(2) M.
