176 



BIOCHEMICAL SYSTEMATICS 



genus indicate definite taxonomic significance. This study will there- 

 fore serve as an example of the type. The veratrum alkaloids are 

 known, so far, from the tribe Veratreae of the Liliaceae. Numerous 

 individual alkaloids occur representing variations in the bsisic nucleus, 

 substitutions of the basic nucleus, and ester derivatives. Kupchan 

 et al. recognized two major groups, the jerveratrum group and the 

 ce veratrum group as follows: 



HO 



Jerveratrum group. Veratramine, rubijervine, isorubijervine, 



jervme. 



OH 



Ceveratrum group. Zygadenine, veracevine, germine, proto- 

 verine. 



The two groups possess the C27 ring structure (other vera- 

 trum alkaloid types are incompletely identified). The jerveratrum 

 types, with few hydroxyl groups, occur as free bases or as simple 

 glucosides. The ceveratrum types, with seven to nine hydroxyl sub- 

 stitutions, usually occur esterified with various acids or ester alkaloids, 

 never as glycosides. Among the ceveratrum types, zygadenine and 

 veracevine occur as monoesters; germine and protoverine occur as tri 

 or tetra esters. 



The genera concerned are Veratrum, Zygadenus, Stenanthium, 

 Schoenocaulon, Amianthium, and Melanthium. Schoenocaulon is re- 

 garded as rather distinctive and homogeneus, Veratrum as relatively 

 homogeneous, Stenanthium as small and diverse, and Zygadenus as 

 quite heterogeneous possibly including several genera (as subgenera). 



The distribution of veratrum alkaloids is given in Table 9-2. 



