388 



DESCRIPTIONS OF ANTIBIOTICS 



Method of extraction: Broth-filtrate extracted 

 with butanol at pH 8.4. Extract azeotropically 

 distilled in vacuo to remove excess water and con- 

 centrate the antibiotic. Addition of Skellysolve 

 B to concentrate gives precipitate. Filtered aque- 

 ous solution of solid at pH 7.5 to 8.0 reprecipitated 

 by adjusting to pH 3.3. Solid extracted into water- 

 saturated butanol. Extract concentrated in vacuo. 

 Precipitate forms on addition of acetone to con- 

 centrate. Solid dissolved in 85 per cent aqueous 

 methanol and reprecipitated with acetone (1). 



Chemical and physical properties: Polypeptide. 

 Pale cream or gray amorphous solid. Molecular 

 weight, about 1000. Ultraviolet absorption spec- 

 trum maxima at 340 niju {E'l'U 127) and 260 to 280 

 niM (broad low peak). C = 57.4%; H = 6.74%; 

 N = 13.1%. No S. Most soluble in water above 

 pH 8.5; least soluble at pH 3.3. Inorganic salts 

 depress solubility in water. Moderately soluble in 

 alcohols; very slightly soluble in acetone and 

 ethyl acetate. Insoluble in ether, chloroform, and 

 hydrocarbons. Heat- and pH-stable. Ninhydrin, 

 biuret, and Fehling tests negative. Contains 

 glycine, alanine, threonine, and aspartic acid (1). 



Biological activity: Active on gram-positive bac- 

 teria (1.6 to 31.2 yug per ml). Not active on gram- 

 negative bacteria or C. albicans. No cross-resist- 

 ance with commonly used antibiotics. Active 

 against Staph, aureus and D. pneumoniae infec- 

 tions in mice (2). 



Toxicity: LDso (mice) >1000 mg per kg orally, 

 intravenously, intrajjeritoneally, or intramuscu- 

 larly. Not absorbed orally (3). 



References: 



1. Misiek, M. et cd. Antibiotics Ann. 1957- 



1958, pp. 852-855. 



2. Gourevitch, A. e< a?. Antibiotics Ann. 1957- 



1958, pp. 856-862. 



3. Tisch, D. E. et cd. Antil)iotics Ann. 1957- 



1958, pp. 863-868. 



Tennecetin 



Produced by: Slreptomyces chattanoogensis. 



Method of extraction: Extraction of broth-filtrate 

 with n-butanol, concentration of solvent in vacuo, 

 precipitation with anhydrous ether. 



Chemical and physical properties: Tetraene. 

 Soluble in water, methanol, 95 per cent ethanol, 

 propylene glycol, pyridine, formamide, and n-bu- 

 tanol. Insolulile in chloroform, ethyl acetate, 

 amyl acetate, ether, and petroleum ether. Aque- 

 ous solutions are alkaline. Solutions in water 

 stable for at least 1 month in the refrigerator. 

 UnafTected by light. Stable for 20 minutes at pH 

 7.0 at 100°C. Light-absorption maxima at 288, 300 



to 302, and 315 to 318 m^u. Infrared absorption 

 spectrum given in reference 1. If chromatographed 

 on paper using wet butanol, tennecetin has differ- 

 ent Rf values from rimocidin and nystatin. Wine- 

 i-ed color with concentrated sulfuric acid. Potas- 

 sium permanganate is readily decolorized. No 

 reaction with FeClj . Negative ninhydrin test (1). 



Biological activity: Active against yeasts, fila- 

 mentous fungi, and some bacteria, such as certain 

 species of Corynebacteriiim and Pseudomonas (1). 



Toxicity: LDso (mice) 125 mg per kg intraperi- 

 toneally, 180 mg per kg subcutaneously. LD50 

 (rabbits) 20 mg per kg intravenously, 120 mg per 

 kg intramuscularly, 68.5 mg per kg intraperitone- 

 all}', 180 mg per kg subcutaneouslj', and >200 mg 

 per kg orally (2). 



References: 



1. Burns, J. and Holtman, D. F. Antibiotics 



& Chemotherapy 9: 398-405, 1959. 



2. Barr, F. S. Antibiotics & Chemotherapy 



9: 406^08, 1959. 



Tertioiiiycin A 



Produced by: Slreptomyces eurocidicus (the same 

 strain also produces eurocidin and azomycin) ; S. 

 albireticuli (this culture also produces carbomy- 

 cin, eurocidin, and enteromycin). 



Method of extraction: I. Culture-filtrate ad- 

 justed to pH 2.0 and extracted with ethyl acetate; 

 this extract contains azomycin. The pH of the 

 culture is then adjusted to 7.0, and the culture 

 extracted again with ethyl or butyl acetate; this 

 second extract contains tertiomycin. E.xtract con- 

 centrated under reduced pressure to a syrup. 

 Syrup extracted with pH 2.0 water. The aqueous 

 solution extracted with ethyl acetate at pH 7.0. 

 Ethyl acetate solution concentrated in vacuo. 

 Residue extracted with ether; the ether solution 

 concentrated in vacuo, leaving tertiomycin. Re- 

 crystallized from ethanol (1). II. Broth-filtrate 

 extracted at pH 8.0 to 8.2 with butyl acetate. 

 Extract washed with water and extracted with 

 dilute HCl (pH 2.0). Extract adjusted to pH 6.5 

 and evaporated to dryness. Residue taken up in 

 benzene; hexane added to incipient precipitation. 

 Crystals of carbomycin are deposited on standing. 

 Mother liquor evaporated in vacuo. Benzene solu- 

 tion of this residue extracted with acidic water 

 (pH 1.0 to 2.0). Back-extracted into chloroform. 

 Re-extracted into water. Aqueous extract adjusted 

 to pH 9.0, and extracted with ether. Ether evap- 

 orated to dryness. Recrystallized from benzene- 

 he.xane (2). 



Chemical and physical properties: White needle- 

 shaped crystals. Browns at 208°C; melts at 215- 



