Pfizer Handbook of Microbial Metabolites 236 



acid, and by further hydroxylations to leucomelone or other 

 terphenylquinones . 



O 



\ 



c o 



c c 



\/\ 



c c- 



o c 



\ 



o 



Pulvinic Acid Leucomelone 



If this suggestion can be confirmed experimentally, it will re- 

 late this type of benzoquinone metabolite to the shikimic acid 

 route of biogenesis. 



The biosynthesis of a benzoquinone, aurantiogliocladin, has 

 been studied, by using C"-labeled formate and acetate. ^^ The 

 results demonstrated formation from 4 moles of acetate with de- 

 carboxylation, C-methylation, post-oxidation in the aromatic 



CH3^ 

 ' Q 



% O 



C— CH3 CH3O II CHa 



O -^ 



CH3— ic=o] 



Acetate Aurantiogliocladin 



ring and 0-methylation of the phenolic hydroxyl groups. 

 6-Methylsalicylic acid appears to be an intermediate.^^ 

 Aurantiogliocladin, isolated from a gliocladium specimen, re- 

 sembles the coenzymes Q. These substances occur in the cell 

 mitochondria of a wide variety of organisms. They are benzo- 

 quinones substituted similarly to aurantiogliocladin, but with 



^^ A. J. Birch, R. I. Fryer and Herchel Smith, Proc. Chem. Soc, 

 343 (1958). 



19 Private communication from Herchel Smith. 



