Chromatographic hivestigations of Indole Compounds 85 



Cotv* ^y., PM. BM. VM. W^ COK. Am. -- :■■ /M, 



n 



# 



• 



1P» 





Fig. 5. Chromatograms of extracts of (A) wheat-treated and (B) pea-treated solu- 

 tions of the methyl esters of w-(indole-3-)alkanecarboxylic acids sprayed with Ehr- 

 lich's reagent. See page 73 for chemical names corresponding to the abbreviations. 



whereas when the side-chain is comparatively long, hydrolysis to yield 

 the corresponding acid readily occurs. This situation, like that al- 

 ready observed in the corresponding homologous series of carbona- 

 mides, clearly suggests that enzymatic hydrolysis of the terminal ester 

 grouping is influenced by the proximity of the indole ring. 



ca-(Indole-3-)alkanenitriIes 



All of the nitrile series, except indole-3-nitrile, showed activity in 

 the wheat cylinder test (Table 2, p. 77) . This result suggests that 



hydrolysis of -CN > -COOH, followed in the case of higher 



members of the series by (3-oxidation to yield either the highly active 

 acetic or propionic acids, is the most probable degradation pathway 

 for members of this series in wheat tissue. The chromatographic and 

 bioassay results (Figures 7 and 8) obtained in wheat metabolism ex- 

 periments support this view. Thus, in extracts of the metabolized 

 nitrile, acetonitrile, and propionitrile, the corresponding carboxylic, 

 acetic, and propionic acids were clearly apparent on the chromato- 

 gram (Figure 7). Similarly, the butyro- and valero-nitriles were shown 

 to produce not only the corresponding butyric and valeric acids, but 

 also, respectively, the acetic and propionic acids by p-oxidation. With 

 the capro- and heptano-nitriles, however, no indication of the pres- 

 ence of the corresponding caproic and heptanoic acids was observed 

 on the chromatogram, but the presence of their lower alternate homo- 

 logues, which could have arisen from the (3-oxidation of these two 



