DESCRIPTIONS OF ANTIBIOTICS 



251 



cent in methanol). Ci5Hv,04N: C = t)4.3',o; H = 

 7.80' r; N = 4.90%. More heat-stable than cyclo- 

 heximide. Acetate: m.p. 150.5-152°C. [a|n ' = 

 +02.5° (c = 2 per cent in methanol). Benzuate: 

 m.p. 159-160.5°C. [a]!; ' = +54.6° (c = 1 per cent 

 in methanol) (71 ). 



Biological activity: Has 32 per cent of the activ- 

 ity of cycloheximide on Saccharontyces sake (71). 



Inactone 



(See remarks under cycloheximide.) 

 Chemical and physical properties: Colorless Hat 

 needles; m.p. 116°C. Ultraviolet absorption spec- 

 trum maximum at 330 m/j. {E{^„^ 50) (ethanol). 

 Infrared spectrum similar to that of cycloheximide 

 (51). [a]'^ = —55° (c = 2 per cent in water). Inac- 

 tone is one of eight possible dehydrocyclohexim- 

 ides having the following structure (50, 51): 

 CHs 



Biological activity: None. 



Nonactin (52) 



Chemical and physical properties: Neutral sul)- 

 stance. Colorless needles; m.p. 147-148°C. Opti- 

 cally inactive. Ultraviolet absorption spectrum 

 maximum at 264 m/i (weak). Infrared spectrum 

 given in reference 52. Chemically unreactive sub- 

 stance. C30H48O9 . 



Biological activity: Very little or none. 



Isocyclohe.riinide 



Method of extraction: Mother liquors of cyclo- 

 heximide crystallization batches evaporated uniler 

 reduced pressure. Extraction with chloroform of 

 aqueous concentrate. Chloroform-extract decolor- 

 ized with carbon and concentrated to syru]). Iso- 

 propanol added, and after storage for 3 months 

 at 5 to 10°C, crude isocyclohe.ximide collected. 

 Further purification by chromatography on car- 

 bon, followed by recrystallization. 



Chemical and physical properties: Same infrared 

 light absorption spectnmi as cycloheximide l)ut 

 slight differences in the low cm~' regions; m.p. 

 95-102°C. [a]:' = +32° (c = 1.0 per cent in CH.- 

 OH). 



Biological activity: Thirty per cent of the cyclo- 

 lieximide activity against Saccharomyces pastoria- 

 niis. 



Toxicity: Thirty per cent of the intravenous 

 toxicity of cycloheximide in mice. 

 References: 



1. Leach, B. E. et al. J. Am. Chem. Soc. 69: 



474, 1947. 



2. P^ord, J. H. and Leach, B. E. J. Am. Chem. 



Soc. 70: 1223-1225, 1948. 



3. Felbcr, I. M. and Hamner, C. L. Botan. 



(iaz. 110: 324-325, 1948. 



4. Kornfeld, E. C. et al. J. Am. Chem. Soc. 



71: 150-159, 1949. 



5. Vaughn, J. R. and Hamner, C. L. Proc. 



Am. Soc. Hort. Sci. 51: 435-437, 1949. 



6. Vaughn, J. R. et al. Mich. Agr. E.xpt. Sta. 



Quart. Bull. 31: 456 464, 1949. 



7. Goth, A. and Robinson, F. J. J. Clin. In- 



vest. 28: 1044, 1949. 



8. Whiffen, A. J. Mycologia 12: 253-258, 



1950. 



9. Peterson, D. and Cation, D. Plant Disease 



Reptr. 34.- 5-6, l!t50. 



10. deZeeuw. D. J. and Vaiighn, J. R. Plant 



Disease Reiitr. 34: 7-8, 1950. 



11. Wilson, (1. B. J. Heredity 11: 226-231, 



1950. 



12. Traul), R. et al. J. Am. Pharm. Assoc, 



Sci. Ed. 39: 552-555, 1950. 



13. Anderson, H. H. and Anderson, J. V. D. 



Am. J. Trop. Met!. 30: 193-201, 1950. 



14. Gottlieb, D. et al. Phytopathology 40: 



218-219, 1950. 



15. Phillips, (;. B. and Hanel, E., Jr. J. Bac- 



teriol. 60: 104-105, 1950. 



16. Ivlom])arens, W. Phytopathology 41: 22, 



1951. 



17. Nelson, R. Phytopathology 41: 28, 1951. 



18. Vaughn, .1. R. Phytopathology 41: 36, 



1951. 



19. Ellis, D. E. Plant Di.sea.se Reptr. 35: 91- 



93, 1951. 



20. Young, W. J. and Fulton, R. H. Plant 



Disease Reptr. 35.- 540 541, 1951. 



21. Henry, A. W. et al. Science 113.- 390, 1951. 



22. Whiffen, A. J. Mycologia 43: 635-644, 



1951. 



23. Wilson, H. M. and Duryea, A. W. Arch. 



Neurol. Psychiat. 66.- 470-480, 1951. 



24. Jenkins, \'. E. and Postlewaite, J. C. Ann. 



Internal Med. 35: 1068-1084, 1951. 



25. Loefer. J. B. and Matney, T. S. Physiol. 



Zool. 25: 272-276, 1952. 



26. Kodanui, T. ct al. J. Antibiotics (Japan) 



5: 504-514, 1952. 



27. Beneke, E. S. and \'oung, W. J. Phyto- 



l)athology 12: 2, 1952. 



