DESCRIPTIONS OF ANTIBIOTICS 



319 



Slightly soluble in ether, l>enzene, ethylene di- 

 chloride, and acidic water. Insoluble in water. 

 Unstable to, and turning brown on, exposure to 

 air. Ultraviolet absorption spectnun maxima at 

 250 and 320 m^. Negative FeCl.3 , ninhydrin, biu- 

 ret, Molisch, and Fehling tests. CsoHssNaOe: 

 C = 60.34%; H = 6.41%; N = 7.88%. No S or 

 halogen (1). 



Biological activity: Active on gram-positive bac- 

 teria; less so on gram-negative bacteria. Not ac- 

 tive on B. (u/thracis. Not active on fungi or myco- 

 bacteria (1). 



Toxicity: LD50 (mice) 16 mg per kg intrave- 

 nously (1). 



Reference: 1. Umezawa, H. and Takeuchi, T. 

 J. Antil)iotics (Japan) 5: 270-273, 1952. 



Nocardaniiti 



Produced by: Xocardia sj). similar to .Y. flavesccns 

 (1). 



Method of extraction: Mycelium-containing cul- 

 ture-broth extracted with butanol. Extract con- 

 centrated to dryness in vacuo. Residue washed 

 and pulverized with ether, filtered, then taken up 

 in hot water. Crystallizes on cooling (1). Recrys- 

 tallized from water-saturated butanol or hot water 

 (2). 



Chemical and physical properties: Reddish 

 needles (1,2); ni.]). 183-184°C. Soluble in boiling 

 methanol and dilute NaOH. Slightly solulile in 

 hot water (1). Optically inactive. Positive am- 

 moniacal silver nitrate and Fehling tests (2). 

 Hygroscopic (1). Cives a red-l)rown color with 

 FeCls (aqueous or alcoholic) and a green color 

 with copper chloride (1). Monoacetate: Fine 

 needles; m.p. 118°C. CuHieOeNo : C = 54.84%; 

 H = 6.90%; N = 11.34%; COCH, = 17.57% (2). 

 Base: CgHnO-jN.. (2). Structure of nocardamin 

 given in Chapter 6. 



Biological activitij: Active on mycobacteria. Not 

 active on bacteria or fungi (2). Iiuictivated l)y 

 serum (1). 



References : 



1. Stoll, A. et al. Schweiz. Z. Pathol, u Bak- 



teriol. 14: 225-233, 1951. 



2. Stoll, A. et al. Helv. Chim. Acta 34: 862- 



873, 1951. 



Nocardiaiiiii 



Produced by: Nocardia sp. (1). 



Method of extraction: Filtered broth extracted 

 with ether. Extract dehydrated and evaporated to 

 dryness. Residue dissolved in chloroform-ether 

 (50:50) or benzene and chromatographed on alu- 



mina. A reddish material eluted with chloroform- 

 ether or chloroform; recrystallized from methanol 

 (1). 



Chemical and physical properties: Weak base (2). 

 C65-67H96-i04Oi.^N,s: C = 57.25%; H = 7.25%; 

 N = 18.3%. No S, P, or halogens. Red prisms; 

 m.p. 228-235 °C (decomposition). Soluble in chlo- 

 roform, glacial acetic acid, and pyridine; 

 moderately soluble in acetone, methanol, and 

 dilute acids; sparingly soluble in water and ether; 

 insoluble in petroleum ether, carbon disulfide, and 

 carbon tetrachloride. [a]f = —223° (c = 0.3 per 

 cent in methanol). Ultraviolet al)sorption spec- 

 trum maximum at 440 mn (log e = 4.52) (meth- 

 anol). Infrared spectrum given in reference 1. 

 Negative xanthine, Liebermann, Schiff, Ehrlich, 

 biuret, and hydroxamic acid tests. Acid hydroly- 

 sates give negative ninhydrin and Ehrlich tests, 

 but a methanolic solution of alkali fusion prod- 

 ucts to which concentrated HCI has been added 

 gives a positive Ehrlich test, indicating possible 

 presence of jjyrrole nuclei. 



Biological activity: Active on gram-positive 

 bacteria; not active against gram-negative l)ac- 

 teria or mycobacteria. 



References: 



1. Bick, I. R. et al. Antibiotics & Chemo- 



therapy 2: 255-258, 1952. 



2. Cram, 1). J. (iivcTi in Benedict, R. G. 



Botan. Rev. 19: 229 320, 1953. 



\<K'ar<liii 



Produced by: .Xocardia cocliaca (1). 



Synonym: PossiV)le relationshij) with trehalosa- 

 mine. 



Method of extraction: Broth-filtrate stirred with 

 charcoal. Eluted with ether-95 per cent ethaaol 

 (1:1). Evaporated to dryness. Mycelium extracted 

 with ether-ethanol (1:1). Production of the anti- 

 biotic (l)ut not the mycciiiun) greatly stimulated 

 t)y trehalose. 



Chemical and physical properties: Crude sul)- 

 stance. Water-soluble and thermostable. 



Biological activity: Active on certain strains of 

 mycobacteria, including M. tuberculosis var. 

 hominis H37Rv. Active in vivo on mycobacteria in 

 chick embryo, guinea pig, and mouse (1,2). 



Toxicity: 25 ing of crude nocardin is more toxic 

 to mice than 1.5 mg of streptomycin, sul)cutane- 

 ously (2). 



References: 



1. Emmart, E. W. Am. Rev. Tuberc. .i6: 316- 



333, 1947. 



2. Emmart, E. W. et al. J. Bacteriol. .57: 



505-514, 1949. 



