220 



DESCRIPTIONS OP^ ANTIBIOTICS 



the same ultraviolet and infrared absorption spec- 

 trum as amicetin. Bamicetin is more water-soluble 

 than amicetin. Can be ditTerentiated from amicetin 

 by X-ray diffraction pattern studies or counter- 

 current distribution (1-butanol-O.l M phosphate 

 buffer, pH 6.9). Anhydrous, high melting point 

 form less soluble in water than the hydrated form. 

 Rf value = 0.22 (1-butanol saturated with 0.05 .1/ 

 pH 7.0 j)hosphate buffer). Negative Bratton-Mar- 

 shall and Ehrlich tests. C,8H4oN609 : C = 55.16%; 

 H = 6.8l7o; N = 13.62% (1). Acid hydrolysis 

 yields cytimidine and the monomethylamino- 

 glycoside (bamicetamine), Ci3H25N06 (1-3). 



Biological activity: On a weight basis, has twice 

 as much activity as amicetin against E. coli (1). 



Toxicity: Less irritating than amicetin when 

 administered subcutaneously to dogs (1). 



References: 



1. British Patent 707,332, April 14, 1954. 



2. Haskell, T. H. el al. J. Am. Chem. Soc. 80: 



743-747, 1958. 



3. Haskell, T. H. J. Am. Chem. Soc. «(»: 747- 



751, 1958. 



Blasticidins 



Produced by: Streptoniyces griseochronwgenes. 



Method of extraction: Broth-filtrate extracted 

 with butanol at pH 4.0. Extract shaken with so- 

 dium bicarbonate solution, then water. Solvent 

 concentrated, then dried in vacuo. Residue ex- 

 tracted with methanol. Extract evaporated in 

 vacuo. Resulting powder extracted with ether. 

 Ether-insoluble residue named blasticidin A. 

 Petroleum ether added to the ether precipitates 

 crude blasticidin C. After concentration of the 

 petroleum ether to a syrup and distillation in 

 vacuo, a colorless liquid, blasticidin B, is obtained. 

 Purification of blasticidin C by chromatography 

 on alumina from chloroform solution, and elution 

 with ethanol. 



Chemical and physical properties: A: Light yel- 

 low powder. Soluble in water, methanol, ethanol, 

 and water-saturated butanol. Insoluble in ben- 

 zene, ether, petroleinn ether, chloroform, and ace- 

 tone. Ultraviolet light-al)sorption spectrum shows 

 one peak at 216 m/i. B: Colorless liquid; li.p. 36°C 

 ^t Kooo iimi Hg. Soluble in methanol, ethanol, 

 benzene, ether, acetone, petroleum ether, and 

 chloroform. Insoluble in water. ('.• Light reddish 

 brown powder. Soluble in ether, acetone, and 

 chloroform. Insoluble in water, benzene, and pe- 

 troleum ether. Broth activity stable to boiling for 

 55 minutes at pH 5.0 to 7.0; unstable when heated 

 above or below this range. 



Biological activity: A, B, and C are moderately 



active on a variety of fungi, including Firicularia 

 o/'i/zae. A is most active (<1 to lOO/ig per ml) (1,2). 

 References: 



1. Fukunaga, K. et al. Bull. Agr. Chem. Soc. 



Japan 19: 181-188, 1955. 



2. Koaze, Y. et al. J. Antibiotics (Japan) 9A: 



89-96, 1956. 



Bla.siicidin S 



Produced by: Streptoniyces griseochroniogenes. 

 Produced by same culture that forms l)lasticidins 

 A, B, and C. 



Method of extraction: Broth-filtrate treated with 

 activated carbon at pH 4.0. Elution with 50 per 

 cent aqueous acetone. Eluate concentrated in 

 vacuo at 40°C. Oxalic acid added to the concen- 

 trate to remove the Ca++. Filtrate passed through 

 an 1R4B column to remove excess oxalate. Effluent 

 chromatographed on IR-50 (H"""). Elution with 

 acetone-1 N HCl, 1:1. Precipitation of antibiotic 

 on addition of acetone. Purification by chroma- 

 tography on alumina from a 90 per cent aqueous 

 methanol solution. Developed with 70 to 90 per 

 cent aqueous acetone and eluted with 50 per cent 

 aqueous acetone. Recrystallized from aciueous ace- 

 tone. 



Physical and chemical properties: Free base: 

 White needles; m.p. 235-236°C. Soluble in water 

 and acetic acid. Insoluble in methanol, ethanol, 

 acetone, benzene, ether, ethyl acetate, butyl ace- 

 tate, chloroform, carbon tetrachloride, and methyl 

 ethyl ketone. Negative FeCl.'? , Fehling, Tollen, so- 

 dium nitroprusside, triphenyltetrazolium chlor- 

 ide, maltol, Millon, Ehrlich, Sakaguchi, Molisch, 

 biuret, xanthoproteic, and Graf ketone tests. Posi- 

 tive diazo, 2,4-dinitrophenylhydrazine, ammonia- 

 cal silver nitrate, ninhydrin, and Graf aldehj-de 

 tests. [aJn = +108.4° (c = 1 per cent in water). 

 C14H20O5N6 : C = 47.119o; H = 5.83%; N = 

 24.46%. Ultraviolet absorption spectrum maxi- 

 mum at 275 niM (ML 349) in 0.1 N HCl or 266 to 

 270 niM (£'lcm 266) in 0.1 A" NaOH. Infrared spec- 

 trum given in reference 1. Most stable at 100°C at 

 pH 5.0 to 7.0. Less stable at pH 4.0 than pH 2.0 or 

 pH 8.0 to 9.0. Melting points: HCl, 224-225°C 

 (decomposition); picrate, 200-202°C (decomposi- 

 tion) ; and helianthate, 224-225°C (decomposition). 



Biological activity: Active on Pseudomonas (5 to 

 50 fig per ml), slightly active on other bacteria (50 

 to 100 fxg per ml), including mycobacteria (10 to 

 50 Mg per ml). Active on phytopathogenic fungi 

 (10 to 100 Hg per ml), including Piricularia oryzae 

 (5 to 10 Mg per ml). 



Toxicity: LD50 (mice) 2.82 mg per kg intrave- 

 nously. 



