THE PAPILIONACEOUS ALKALOIDS: XXI. THE ALKALOIDS OF LUPINUS PILOSUS WALT. AND THE STRUCTURE OF TETRALUPINE

The alkaloidal extract from Lupinus pilosus Walt. was found to contain two alkaloids, one widely occurring one, d-lupanine, and one which had already been reported to occur in this plant, i.e., d-epilupinine, but no lupinine. The alkaloid tetralupine has been found by direct comparison of the bases and their corresponding salts and by their infrared absorption spectra to be identical with dl-epilupinine. A study of the infrared absorption spectra of lupinine and epi-lupinine leads to the same conclusion as the chemical evidence, i.e., that in the former the hydroxymethylene group occupies the axial position whereas in epilupinine this group is in the equatorial position.