Pfizer Handbook of Microbial Metabolites 254 



533 C. CseHgoOo, yellow crystals, m.p. 58-59°. 

 O 



CHo— CH=C— — CH2— CH2— CH=C— 1— CH3 



CH3 CH3 8 



Mycobacterium tuberculosis (Brevannes) 



This substance constituted about 0.59c of the dry cell 

 weight. 



J. Francis, J. Madinaveitia, H. M. Macturk and G. A. Snow, 

 Nature 163 365 (1949). (Isolation) 



H. Noll, R. Riiegg, U. Gloor, G. Ryser and O. Isler, Helv. 

 Chim. Acta 43 433 (1960). (Structure and synthesis) 



C. ANTHRAQUINONES 



534 Anthraquinone pigment from Gibberella fujikuroi, probably 

 C14H10O7, red crystals, m.p. 325° (sealed tube). 

 Partial and tentative structure: 



CHoOH 



+ 20H 



O OH 



The structure may resemble that of cynodontin. 

 Gibberella fujikuroi (Saw.) Wollenweber 

 Yukihiko Nakamura, Tokuji Shimomura and Joji Ono, 

 J. Agr. Chem. Soc. Japan 31 669 (1957). (Isolation) 



535 Clavorubin, C14H12O9, red crystals. 



Has one C — CH3 group. U.V. absorption resembles a 

 1,5,8-trihydroxyanthraquinone. The leuco-acetate (like 

 that of chrysergonic acid) has a diphenyl-like absorption. 



Claviceps purpurea 



B. Franck and T. Reschke, Angew. Chem. 71 407 (1959). 



536 Emodic Acid, C].-,Hs07, orange needles, m.p. 363-365°. 



O 



COOH 



