The isochondrodendrine content of the cornmercial "Bebeerine Hydrochloride" 

 was aDproxiraately twenty per cent of the total, but no bebeerine could be 

 isolated. 



Isochondrodendrine is a structural isomer of bebeerine. It has the same 

 number of atoms and the same functional groups and differs only in the 

 position of one of the ether linkages. Due to this similarity, it is being 

 further investigated for activity against marine borers, 



We next turned our attention to greenheart itself. Generous samples of 

 bark and sarrdust were received from the ./illems Timber and Trading Company 

 and the Greenheart and t/allaba Timber Company. To both of these comfanies 

 we are greatlj/- indebted. The nitrogen contents of dried greenheart samples 

 show small differences which are not significant for -Oumas determinations. 



Samples of greenheart bark from both companies were percolated in an appara- 

 tus which had a capacity of nine pounds of ground bark. The extractions 

 were carried out as in the case of the pareira brava. The ether-soluble 

 alkaloids from the t^w samples were cream colored powders having specific 

 rotations {^'K'2-q, c=l,00,in methyl alcohol) of +125° and +129*^ respectively, 

 Bebeerine is reported to have a specific rotation of +300° « 



Work on the separation of the crude alkaloids into pure components so far 

 has been of a prelirainai^y nature. The alkaloids ar3 quite unstable and 

 discolor slovfly on exposure to light. A sample in methyl alcohol solution 

 which was kept in a refrigerator changed its specixic rotation from +125° 

 to +78° in six months. 



A sample having a specific rotation of +121° was subjected to chromato- 

 graphic analysis. The results are sho.vn in Figure 9. The solvents used 

 xirere progressively moi'^e concentrated solutions of methyl alcohol in 

 methylene chloride. There m.ay be at least as many substances as solvent 

 pairs employed, J>en in this chromatography some change apparently took 

 place since the specific rotations of the fractions are considerably less 

 than expected. 



The chemical and physical properties of the fractions isolated in our 

 pre! iminary study do not correspond vfith those reported for the alkaloid 

 bebeerine. Until further evidence is obtained any mechanism which attempts 

 to explain the resistance of greenheart to marine borers on the basis of 

 the toxic action of bebeerine must be regarded as soDiewhat doubtful. The 

 possibility remains that sone other alkaloid or some other substance is 

 responsible. 



An alcoholic extract of greenheart sawdust was prepared essentially 

 according to the method of Barger and Harrington. ^ This extract contains 

 a large percentage of non-basic material and only a very smaD.l amount of 

 alkaloids. Pine blocks, impregnated with the total extract have been 

 submitted to the Marine Laboratory, University of iaami, for investigation 

 of marine borer resistance. Similar test pieces impregnated virith the crude 



N - 6 



