Lupanines formulae

The first complete formula (I) suggested for lupanine was that of Thoms and Bergerhoff, based mainly on the formation of 2-ethylpyridine when lupanine was distilled with zinc dust, which seemed to indicate a similarity between tropane and lupanine. 

In 1931 Winterfeld and Kneuer, as a result of their observation that jS-lupinane can be obtained from lupanine, and the formation of 2-methyl-pyrrolidine by the oxidation of sparteine, combined these two features in a partial formula (II) for lupanine, which could be developed in various ways depending on the mode of attachment of the methylpyrrolidine residue. In view, however, of Ing s demonstration of the relationship of anagyrine, CJ5H20ON2, to Z-lupanine, CJ5H24ON2, and d-sparteine, C15H28N2, it was elearly neeessary to consider formul for lupanine derivable from the two alternati-ves, which Ing had proposed for anagyrine and which are shown below as (III) and (IV) with the formul for lupanine derived from them (V) by Ing and (VI) by Clemo and Raper. Sparteine would be represented by (V) or (VI) with the change CO CH2. 

Figure 2.12. Genetic formulas of crosses of Lupinus arboreus with L, hartwegi or L, elegans with L. hartwegi. ss—sparteine-synthesizing form LL—lupanine-synthesizing form L L — lupanine-synthesizing form with lower efficiency. Schematic chromatograms correspond to the respective genotypes (Nowacki et al., 1966).

Figure 3.4a. The effect of exposure of plants to light on the composition of lupine alkaloids. Top Artificial light plants were grown in July, the plants exposed 18 hr were additionally illuminated with 4000 lux during the twilight hours, and the plants exposed 12 and 9 hr were covered to shorten the time of exposure. Bottom Natural light plants were planted at month intervals hence, their growth rate was according to their location, Poznan, Poland. The curves represent the concentration of free and esterified alkaloids in the total plant in mg/100 g of plant material (dry weight). The numbers represent the milligram contribution of free alkaloids (ALK) and hydroxylupanine ester fraction (HEF). Formulas lupanine (I) a free alkaloid, and cinnamoyloxylupanine (II) a HEF (Nowacki et ai, 1973). Courtesy of the journal.

Sparteine. As already stated Z-lupanine and Z-anagyrine both yield d-sparteine on reduction. This base was found in Sophora pachycarpa by Orekhov, who continues to use the name pachycarpine for it, and with Kabatschnik and Kefeli ( l has described experiments with oxypachycarpine, on the results of which he adopts for this substance formula (VIII with CH at 10 —> CO) which makes it identical with oxysparteine. from other plants (Nos. 1, 2, 4, 31, list, pp. 116-8). 

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