Hystrine

The new alkaloid hystrine, C10H16N2 (liquid dihydrochloride, mp 209° [a]jj + 0°) and ammodendrine, but none of quinolizidine type (96). The former (LXV) was prepared from the latter by first reacting with hypochlorite to generate the W-chloro compound LXVI, treatment of which with alkali eliminated the elements of hydrogen chloride and hydrolyzed the acetyl group. The crude product was conveniently purified by conversion to the iV -nitroso derivative followed by reduction of the latter with cuprous chloride (97). 

Ten alkaloids have now been isolated from the branches of Genista cinerea DC. These include six esters of 13-hydroxylupanine, four of which have been previously reported. The two esters recently isolated (from Provengal plants) are cinevanine (10), which is the vanillic acid ester of 13-hydroxylupanine, and 13 benzoyloxylupanine. The former had not previously been isolated from natural sources, but the latter had been found previously in Lupinus angustifolius and L albus. The four remaining alkaloids of Genista cinerea are 13-hydroxylupanine, lupanine, anagyrine, and hystrine (11), a base which was first obtained from G. hystrix Lange. 

G. cinerea thus proves to be a plant of some chemotaxonomic interest, because its major alkaloidal constituents are esters of 13-hydroxylupanine, compounds which are characteristic of the genus Cytisus rather than of Genista. In Cytisus species, for instance, the biosynthetic sequence lupanine, 13-hydroxylupanine, 13-hydroxylupanine esters, is often observed. However, G. cinerea also contains alkaloids characteristic of the Genista genus, e.g. anagyrine and hystrine, although these are only present in very small amounts, and in fact anagyrine was not encountered in the extracts from some samples. ... 

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