Some Metabolic Products of Basidiomycetes 11 



which indicate that such activity is not a general property of con- 

 jugated acetylenic linkages but depends, at least in part, on other 

 groupings present in the molecule. Thus, among the basidiomycete 

 polyacetylenes, compounds with similar unsaturated systems may show 

 pronounced specificity in their bacterial and fungal spectra. A more 

 striking demonstration of this fact is afforded by comparison of the 

 compounds diatretyne nitrile and diatretyne amide discussed below. 

 As mentioned previously, the latter is at least 8000 times as active 

 against Staphylococcus aureus as the former. 



More specific questions are raised by the frequent occurrence of pairs 

 of closely related compounds in a culture liquid. Diatretyne amide 

 (XIII) and diatretyne nitrile (XIV) offer one of the most interesting 

 examples of this. Are these compounds synthesized independently 

 by the organism, or do they arise from a common, closely related 

 precursor, or is one the precursor of the other? The likelihood of the 

 last possibility is enhanced by the close structural similarity of the 

 compounds: the difference between them consists only in possession 

 of a nitrile grouping by one and an amide grouping by the other. If 

 this last mechanism does represent the actual sequence, it would further 

 suggest the possibility of the existence in the organism of an amide 

 dehydrase. This would be a novel sort of enzyme, since reports of 

 nitriles of biological origin are comparatively rare, 37 and nothing 

 is known of their close association with the corresponding amide. 

 Diatretyne amide and diatretyne nitrile appear to be the first such 

 pair reported, and diatretyne nitrile is the first reported polyacetylenic 

 nitrile of biological origin. 



The possibility of taxonomic implications of basidiomycete products 

 is interesting to consider. In higher plants, rather extensive investiga- 

 tions have been made by Erdtman's group on the wood of Gymno- 

 spermae (softwoods) and by Sorensen's group using plants of the 

 Composite family. Erdtman has reported 3S that pinosylvin (3,5- 

 dihydroxystilbene) or its methyl ether is present in the heartwood 

 of most species of the genus Pinus, and that other genera of coniferous 

 trees do not contain them. An instance in which "chemical taxonomy" 

 has lent support to a taxonomic classification which apparently is in 

 some question on morphological grounds is furnished by Sorensen's 

 group. On the basis of their investigations of acetylenes of the Com- 

 posite family, they state: 39 ''The power to synthesize acetylenic com- 

 pounds thus separates Tripleurospermum distinctly from Matricaria." 

 Although it appears, on examination of the basidiomycete compounds 



