252 A MANUAL OF THE PENICILLIA 



and water but did not alter the nitrogen content. Moldy soybean cake 

 was reported to have a favorable effect upon rats when added to their 

 ration. 



The biochemistry of PenicilUum charlesii has been studied quite exten- 

 sively, particularly by Professor Raistrick and co-workers in England. 

 The type strain of this species was isolated by J. H. V. Charles from moldy 

 Italian maize, and was recognized to possess unique biochemical reactions 

 when described by George Smith in 1933. Clutterbuck, et al. (1934), 

 found six new optically active acids to be produced by this mold when 

 grown upon Czapek-Dox or Raulin-Thom solutions containing glucose as a 

 carbon source. These were shown to have the following empirical 

 formulae, and for them the accompanying names were proposed: C9H10O4, 

 carolic acid; C9H12O7 (CgHioOe-HaO) carolinic acid; CioHioOe, carlic acid; 

 C10H12O6, carlosic acid; C16H20O6, ramigenic acid; and C26H32O12, verti- 

 cillic acid. Carolic acid, produced in the greatest yields, is monobasic 

 and dextrorotatory, M.P. 123°C. Carlic acid, produced in small amounts, 

 is dibasic and laevorotatory, M.P. 176°C. Carlosic acid, produced in 

 moderate yields on Czapek-Dox medium only, is dibasic and laevorota- 

 tory, M.P. 181°C. Ramigenic acid, produced in small amounts on both 

 media, is dextrorotatory, M.P. 171°C. but softens at 125°C. Verticillic 

 acid, produced in large yields on Raulin-Thom mediiun, is tetrabasic and 

 laevorotatory, M.P. 17rC. In addition to these acids, P. charlesii pro- 

 duced two new polysaccharides, a polygalactose and a polymannose which, 

 upon hydrolysis, yielded (/-galactose and rf-mannose. Both polysacchar- 

 ides were produced on both media in considerable amounts, and afford 

 examples of the ready conversion of glucose into galactose and mannose 

 by a mold. The molecular constitutions of carolic and carolinic acid was 

 carefully investigated by Clutterbuck, Raistrick, and Renter (1935a) 

 and were showTi to be closely related derivatives of Z-7-methyltetronic acid, 

 and closely related structurally to ascorbic acid (Vitamin C). In another 

 paper (1935b) these authors reported molecular constitution of carlic 

 and carlosic acid. These acids were shown to be closely related deriva- 

 tives of ?-7-carboxymethyltetronic acid and to be structurally closely 

 related to carolic and carolinic acid and to ascorbic acid. In a third paper 

 (1935c) the formation of /-7-methyltetronic acid (CsHeOiO was described, 

 and ramigenic and verticillic acids, previously reported, were shown to 

 be artefacts arising from the condensation of /-7-methyltetronic acid and 

 acetone. 



Herbert and Hirst (1935) found the absorption spectra of carolic, caro- 

 linic, carlic, and carlosic acids to be strikingly similar to that of ascorbic 

 acid, to which they are closely related in structure. The presence of these 



