Of course, there still remains -fete possibility that the protective princi- 

 ple is not an alkaloid at all, but some other alcohol -soluble material. 

 This material might possibly turn out to be simple enough to be manufactured 

 readily. If the protective principle is more corarjlicated, it would be 

 vrorth while 'to synthesize and test similar compounds, some of which might 

 become economically feasible materials for virood irapregnation. 



Alkaloids are sometimes defined as nitrogen-containing basic compounds 

 which occur in plants and more rarely in animals. They usually have 

 physiological activity. Figure 1 shows two alkaloids. One of them is 

 bebeerine ±\\ v;hich we are particularly interested. The other is a very 

 abundant alkaloid with a confusingly similar name, berberine. Both 

 ha-pen to be members of the isoquinoline group, I'^ebeerine is also a 

 member of the bis-benzyl isoquinoline sub-group. It is a 36 carbon 

 molecule viith trio basic nitrogen atoms and two free phenolic groups. It 

 can therefore be considered as a phenolic amine, a type of compotind which 

 will be further discussed by Lir, ffoe in the paper which follo^Ts, 



A surgeon in the British Royal Na-^/y, a Dr. Rodie, in l83li. found that 

 greenheart bark contained an alkaloid vihich was useful against undulant 

 fever. In 18I|0, Maclagan^ began an investigation of the bark of the 

 greenheart or bebeeru tree and obtained from it an ether-soluble alkaloid 

 and an insoluble alkaloidal residue. The former he named bebeerine and 

 the latter sipeerine after the native and the Dutch names for the green- 

 heart tree. In 1869, aaclagan and Gamgee? published preliminary results 

 of an investigation of the bases in greenheart v»'ood. They isolated a 

 chloroform-soluble alkaloid, nectandria, and a chloroform- insoluble base, 

 and shov/ed the presence of still another base. E>:cept for possible dupli- 

 cation, greenheart thus contained at least five alkaloids. The authors 

 apparently published no further results. 



Jn 1838, =/iggers" isolated the alkaloid pelosine from Cissajnpelos pareira 

 and also from the raw medicine obtained fron Radi:x pareirae bravae. The 

 name pareira brava is derived from the Portuguese for wild grapevine and 

 the root of this plant was first imported into Germany from South America 

 in 1688. In 1869, Fllickiger^ showed that pelosine and bebeerine v^ere 

 identicals The latter name took precedence, but subsequent work on 

 bebeerine v/as carried out with material derived from pareira brava and 

 not vjxth that obtained from greenheart. In fact, no further chemical 

 studies of the vjood or bark of the greenheart tree appear to have been 

 published, except for the above mentioned brief work of Bai'ger and Harrington. 



Recently there has been much interest in curare alkaloids v;hich are obtained 

 from the same species of plants as pareira orava. Curare active compounds 

 induce flaccidity of striated muscle and have become increasingly usefiol 

 in abdominal surgery and other applications vrhere muscle relaxation is 

 important. The chemical frequently used for tliis purpose is the quart ernary 

 alkaloid, tubocurarine chloride. It was originally obtained from tubo 

 curare, one of three types of curare used as arrow poisons by the South 

 American Indians, It occurs together with a closely related tertiary 



N - 2 



