AROMATIC COMPOUNDS 

 1.5 



173 



1.0 2.0 5.0 10 



Ferrous sulfate, mg per liter 

 (logarithmic scale) 



20 



Figure 7. The effect of iron on the formation of patulin and gentisyl alcohol by 

 PenicilUum sp. From data of Brack (93). 



acid, but at higher concentrations of zinc this compound is replaced 

 by a mixture of gentisyl alcohol, patulin, and toluquinone (176). This 

 type of analysis, in which an environmental modification causes a 

 shift in metabolic products, is extremely promising. 



PenicilUum brevi-compactum produces several related phenols. 

 Both the temporal sequence of appearance of these compounds (409) 

 and the observation that the organism when fed one compound pro- 

 duces others (230) support the proposition that these structurally re- 

 lated molecules are related biologically as well. 



A role of the polyphenol oxidases in the conversion of phenols to 

 other compounds is probable but has not been investigated in the 

 fungi; Mason (371) reviews several theories on the function of these 

 enzymes in the origin of aromatic products of higher plants. 



Enzymatic Transformations of Aromatic Compounds. The major 

 known types of attack on aromatic compounds may be summarized 

 as: (1) the oxidation of aliphatic side chains, (2) the oxidation of 

 phenols, (3) the oxidative fission of the aromatic ring, and (4) the 

 hydrolysis of depsides. 



The side chain of phenylacetic acid is oxidized by PenicilUum 

 chrysogenum; benzaldehyde is formed during the oxidation and is 



