The Veratrum Alkamines 



OSKAR WINTERSTEINER 



This essay attempts to give a brief account of the advances made 

 in the structure elucidation of the veratrum alkamines, and in particu- 

 lar to bring out how the peculiar dichotomy of skeletal structure which 

 sets these alkaloids, as a group, apart from other families of steroidal 

 bases came to be recognized. Naturally only the facts most directly 

 relevant to the elaboration of the presently accepted structures can be 

 presented here. The literature cited covers most of the more recent 

 work, except that on cevine, for which the reader is referred to the 

 bibliography in the comprehensive 1954 paper on the constitution of 

 this alkamine by Barton et al. 1 More detailed if slightly outdated 

 resumes of the chemical and other aspects of the subject can be found 

 in review articles. 2 



Of the more than two dozen veratrum alkaloids now known the 

 majority is of the conjugated type (esters or glucosides) ; the much 

 smaller group of unconjugated bases (alkamines) from which these 

 are derived comprises only eight well-characterized members. They all 

 contain twenty-seven carbon atoms and one nitrogen atom, which in all 

 but two instances (jervine, C27H;{ 9 3 N; veratramine, C27H39O2N) is 

 tertiary. The tertiary bases include rubijervine and isorubi jervine 

 (C27H43O2N) , and a group of highly oxygenated compounds (zygade- 

 nine, C^H^C^N; * cevine, genuine, C27H 43 O s N; and protoverine, 

 C27H43O9N), which occur in nature predominantly in combination with 

 acids, i.e., as the alkamine moieties of the hypotensically active and 

 hence medicinally important ester alkaloids. 



Much of our present knowledge of the chemistry of the alkamines 

 we owe to the fundamental studies of W. A. Jacobs, who, together with 

 L. C. Craig, began exploring this subject in 1937. In the initial phase 



* This alkamine, together with certain ester alkaloids derived from genuine, 

 occurs in Zygadenus venenosus, which is not a member of the genus Veratrum. 



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