DESCRIPTIONS OF ANTIBIOTICS 



183 



l)enzene, ethylene dichloride, methanol, ethanol, 

 l)enzyl alcohol, and water at acid pH. Soluble at 

 liigh temperatures in acetone, ethyl acetate, 

 dioxane, butanol, and Tetralin. Scarcely soluble 

 in ether, carbon bisulfide, distilled water, and 

 petroleum ether. No characteristic ultraviolet 

 absorption in ethyl ether or ethanol. Infrared 

 data given in reference 1, and spectrum in refer- 

 ence 3. [a]" = —48.7° (c = 1 per cent in chloro- 

 form). Positive Fehling, Tollen, and silver mirror 

 tests. Cherry-red color with Elson-Morgan rea- 

 gent. Negative biuret, ninhydrin, Millon, Molisch, 

 orcinol, phloroglucinol, Pauly, FeCls , and Saka- 

 guchi tests. Stable to boiling at pH 2 to 9 for 10 

 minutes. Most stable at neutrality, less so at 

 acid pH, and relatively unstable at alkaline pH. 

 Precipitated by ammonium reineckate and picric 

 acid, but not flavianic acid or methyl orange. 

 C.25H44NO7 : C = 63.38' e; H = 9.14%; N = 2.91%; 

 molecular weight 477; or C32H.i409N: molecular 

 weight 586.4. No S, P, or halogen (1, 3). 



Biological activity: Active on gram-positive 

 bacteria at 0.1 to 12.5 y.g per ml, including M. 

 smegrnatis. Less active (25 to 250 ixg per ml) on 

 other mycobacteria. Inactive on gram-negative 

 bacteria, filamentous fungi, yeasts, phage, and 

 viruses tested. Active in vivo against pneumo- 

 coccal and Borrelia duttonii infections (1, 3). 

 Cross-resistance with erythromycin-carbomycin 

 group (2). 



Toxicitij: LD50 (mice) 1.5 gm per kg orally, 

 0.5 gm per kg subcutaneously (3). Mice tolerate 

 249 mg per kg intraperitoneally, 124.5 mg per kg 

 intravenously, and 41.5 mg per kg intracerebrally. 

 Fifty per cent are killed by 332 mg per kg intra- 

 peritoneally, 166 mg per kg intravenously, and 

 58 mg per kg intracerel^rally (1). 



References: 



1. Takahashi, B. J. Antil)iotics (Japan) 7.4: 



149-154, 1954. 



2. Nishimura, H. et al. Ann. Rept. Shionogi 



Research Lab. 6: 278-285, 1956 (Chem. 

 Abstr. 51: 5193d, 1957). 



3. Kuroya, M. and Nishimura, H. Japanese 



Patent 7750, September 17, 1957. 



.41boverticilliii 



Produced by: Streptoniyces sp. 



Chemical and physical properties: Colorless, 

 amorphous powder. Soluble in water and metha- 

 nol. Insoluble in acetone, esters, and ether. LTltra- 

 violet absorption spectrum maximum at 208 m^ 

 (0.1 N HCl) or 218 mM (0.1 N NaOH). [at" = 

 — 33.5° (c = 1.0 per cent in water). Negative 

 Tollen, Molisch, Benedict, maltol, Elson-Morgan, 



biuret. Millon, Sakaguchi, anthrone, and FeCls 

 tests. Yellow precipitate with Fehling's reagent; 

 positive ninhydrin. Stable to heating at 100°C 

 for 1 hour at acid and neutral pH. Does not yield 

 furfural on acid hydroly.sis. Reineckate: C = 

 32.03%,; H = 5.21%; N = 22.72%; Cr = 9.35%. 

 HCl: C = 40.58%; H = 6.48%; N = 18.12%,; 

 CI = 8.98';;,. No s. 



Biological activity: Active on mycobacteria 

 (0.002 to 2.0 ng per ml). Very slightly active on 

 Sarcina liitea, B. suhtilis, and B. anthracis. Not 

 active on Staph, aureus or other l)a.cteria, fungi, 

 or yeasts tested. 



Toxicity: LD,=,fi (mice) 50 to 100 mg per kg in- 

 travenously. No delayed toxicity. 



Reference: 1. Maeda, K. et al. J. Antibiotics 

 (Japan) 11 A: 30-31, 1958. 



Alioniycin 



Produced by: Streptomyces acidomyceticus . 



Remarks: This culture also produces actithiazic 

 acid. Culture belongs to the lavendulae group. 



Method of extraction: Extracted from the my- 

 celium with hot methanol. Extract concentrated 

 in vacuo, adjusted to i)H 9.0, and extracted with 

 butanol. Solvent removed in vacuo, and acetone 

 added to the residual syrup to give aliomycin. 

 Can also be extracted from mature culture- 

 broths. 



Chemical and physical properties: Pentaene. 

 Yellow powder. Soluble in distilled water, alka- 

 line water, glacial acetic acid, methyl Cellosolve, 

 ethylene glycol, methanol, ethanol and hot Inita- 

 nol, isoamyl alcohol, and dioxane. Insoluble in 

 water at pH 3.0, or in ether, benzene, ethyl ace- 

 tate, or acetone. Ultraviolet absorption spectrum 

 maxima at 321, 330, and 350 m^. (!ives a dark 

 purple color in concentrated H2SO4 . Positive 

 Fehling test. Slightly positive Molisch test. 

 Stalile at neutrality. Contains S and N, but no 

 halogen. 



Biological activity: Active on fungi and yeasts 

 at 7.5 to 20 ixg per ml. Active on Trichomonas 

 foetus. Active on Yoshida sarcoma cells at 0.5 

 mg per ml. Activity partially reversed by cyste- 

 ine. 



Toxicity: LD511 (crvide substance, mice) 45 mg 

 per kg intraperitoneally; 2.65 gm per kg orally. 



Reference: 1. Igarashi, S. et al. J. Antibiotics 

 (Japan) 9B: 101-103, 1956. 



A I 



oiii^ cm 



Produced by: Streptomyces sp. (1). 

 Method of extraction: Dried powdered mycelium 

 extracted with ethyl acetate containing about 1 



