DESCRIPTIONS OF ANTIBIOTICS 



339 



liutyl and ethyl acetate, chloroform, benzene, and 

 petroleum ether. Ultraviolet absorption si)ectrum 

 shows only end-absorj^tion. Positive ninhydriu 

 (in pyridine) and glucosamine tests. Negative 

 nmhydrin (in water), Sakagiichi, Tollen, Fehling, 

 i)iuret, maltol, and FeChs tests. No S or halogen. 

 Reinerkate: Red plates; m.p. 195-197°C (decom- 

 position). Infrared absorption spectra of the 

 hydrochloride and reineckate given in reference 1. 

 Unstable in weakly acid solution. Most stable at 

 pH 7 to 9. Possi1)ly composed of a peptide and a 

 carbohydrate moiety (1, 3). Hydrolysis products 

 (concentrated HCl) include two ninhydrin-posi- 

 tive substances (Rf values given in reference 3); 

 product with 40 per cent H2SO4 may be furfural (3). 

 Base: Cobalt-blue amorphous powder. Soluble in 

 water; slightly soluble in methanol; insoluble in 

 other organic solvents. Ultraviolet absorption spec- 

 trum maxima at 244 {Epcm 135) and 295 to 300 mix 

 {Eitm -17). Positive ninhydrin and diazo reactions. 

 Negative Fehling, Tollen, Sakaguchi, and Molisch 

 tests. CssHgiNnOsiCu (4). Copper-free phleonujcin: 

 White to pale green amorphous powder. Copper 

 easily reintroduced to give phleomycin (4). 



Biologicnl activity: Weakly active on bacteria. 

 Active against M. phlei at <0.3 ng per ml. Not 

 active on fungi. Partial cross-resistance with 

 kanamycin when E. roli is used, Init not with 

 Mycobacterium 007 (2). Copper-free phleomycin is 

 as active as phleomycin, except against myco- 

 bacteria. 



Toxicitii: Hydrochloride: Ll).=,o (mice) 250 to 500 

 mg per kg intravenously. No delayed toxicity 

 noted (1). Phleomycin: LDsn 40 to 50 mg per kg (no 

 route (jr animal given) (4). Copper-free phlenniycin: 

 LD50 150 mg per k8 (no route or animal given) (4). 



References: 



1. Maeda, K. et al. J. Antibiotics (Japan) yA: 



82-85, 1956. 



2. Umezawa, H. Ann. N. Y. Acad. Sci. 76: 



20-26, 1958. 



3. Japanese Patent 2598, April 17, 1959. 



4. Takita, T. et al. J. Antibiotics (Japan) 



12A: 111, 1959. 



Phtliioniyciii 



Produced by: Streptouiyces luteochromogenes (1). 



Synonym: Closely related to viomycin (1). 



Method of extraction: Adsorption on cation 

 exchange resins, elution with 0.5 to 1.0 A^ HCl. 

 Precipitation of the crude hydrochloride by 

 methanol (1). 



Chemical and physical properties: Basic sub- 

 stance, white. Positive biuret, Sakaguchi, and 

 ninhydrin test. Negative Molisch, maltol, and 



FeCl.-i tests. Ultraviolet light -absorption maxima 

 at 268 (0.1 A' HCl) and 282 m^ (0.1 N NaOH) (1, 3). 

 [a\\, = —11°. Forms a water-soluble hydro- 

 chloride and sulfate (3). 



Biological activity: Active in concentrations of 

 6 to 25 ixg per ml against gram-positive bacteria 

 and mycobacteria. No activity against fungi. 

 Some activity against the tubercle bacillus in mice. 



Toxicity: LD.mj (mice) 600 mg per kg intrave- 

 nously. 



References: 



1. Maeda, K. et al. J. Antil)iotics (Japan) 



6A: 183-185, 1953. 



2. Miyamoto, Y. and Maeda, K. J. Antil)iotics 



(Japan) 7A: 17-20, 1954. 



3. Umezawa, H. et al. Japanese Patent 3096, 



May 9, 1955. 



Phytoactin 



Produced by: Streptomyces sp. 



Chemical and physical properties: Polypeptide. 

 Soluble in methanol, ethanol, 1-butauol, chloro- 

 form, acetone, methyl isobutyl ketone, and other 

 organic solvents. Slightly soluble in ether and 

 water. Insoluble in petroleum ether. Heat -stable. 

 Not digestetl by pepsin, trypsin, or proteases, 

 nialyzes through cellophane into aqueous meth- 

 anol. Acid hydrolysates contain valine, a-alanine, 

 proline, leucine (or isoleucine), arginine, glycine, 

 and serine (1 ). 



Biological activity: Active on gram-positive 

 bacteria and fungi. Control of tomato early blight 

 (greenhouse studies), tomato late blight, and bean 

 rust (1). Active in field trials on powdery mildew 

 (Podosphaera leucolricha) of pear (2). 



Toxicity: Not toxic to tomato or bean plants at 

 therapeutic levels (1). 



References: 



1. Ziffer, J. S. et al. Phytoi)athology 47:539, 



1957. 



2. Si)rague R. Plant Disease Reptr. 42: 1208- 



1209, 1958. 



Pliytostreptin 



Produced by: Mutant of phytoact in-producing 

 Streptomyces sp. 



Chemical and physical properties: Polypeptide. 

 Soluble in water, methanol, ethanol, l-l)vitanol, 

 chloroform, acetone, methyl isobutyl ketone, and 

 other organic solvents. Slightly solulile in ether. 

 Insolul)le in petroleum ether. Heat -stable. Not 

 digested by pepsin, trypsin, or proteases. Dialyzes 

 through cellophane into water. Acid hydrolysates 

 contain same amino acids as phytoactin (1). 



Biological activity: Active on gram-positive 



