400 



DESCRIPTIONS OF ANTIBIOTICS 



Toxicity: Na salts: LDjo (mice) 1(30 mg per kg 

 (A) and 400 mg per kg (B) intra venovisly. 



Reference: 1. Isono, K. et at. J. Antibiotics 

 (Japan) IIA: 264-267, 1958. 



Unaniycin 



Produced by: Streptomyces fungicidicus. 



Method of extraction: Adsorption on charcoal. 

 Charcoal washed with water and eluted with 70 

 per cent acetone at pH 9.0. Eluate concentrated 

 in vacuo. Concentrated solution extracted with 

 ethyl acetate. Extract adjusted to pH 3.0 and 

 stored overnight in ice-box; precipitate forms. 

 Precipitate dissolved in water at pH 8.4. On addi- 

 tion of acetone to 85 per cent, a precipitate occurs 

 and is removed. The acetone is concentrated in 

 vacuo. Concentrate adjusted to pH 3.0 and stored 

 in the cold; crude crystals form. These are washed 

 with ethanol, dissolved in 80 per cent aqueous 

 methanol, concentrated in vacuo, and cooled; 

 unamycin crystals form. Cation exchange resins 

 can also be used to purify this antibiotic (1). 



Chemical and physical properties: Acidic tet- 

 raene. White needle-shaped crj-stals. Becomes 

 reddish above 140°C and decomposes at 148- 

 150°C. Soluble in formamide, dimethylformamide, 

 methanol, aqueous ethanol, aqueous propanol, 

 aqueous butanol, aciueous acetone, aqueous di- 

 oxane, pyridine, glacial acetic acid, and alkaline 

 water. Slightly soluble in isopropanol and butanol. 

 Insoluble in acetone, dioxane, propylene glycol, 

 ether, benzene, petroleum ether, and acidic water. 

 Light-absorption maxima at 290 {E^Zm 643), 30^ 

 {EXL 1010), and 319 m^ (EXL 875), with a shoulder 

 at 279 niyii (£'icm 328). Infrared spectrum, which is 

 given in reference 1, contains a band at 6.4 m^u. 

 C = 52.24%; H = 7.77%; N = 1.74%. No halogen 

 or S. [af^ = —92° (c = 1 per cent in 80 per cent 

 aqueous methanol), [a]^ = -1-79.2° (c = 1 per cent 

 in dimethylformamide). Negative FeCl? , Millon, 

 Fehling, and Tollen tests. Positive Molisch test. 

 Permanganate and bromine solutions are decol- 

 orized. Schiff test gives a light pink color, and 

 sulfuric acid gives a reddish brown color turning 

 black. Rf = 0.94 with 50 per cent aqueous acetone, 

 and Rf = 0.68 with water-saturated butanol (1). 

 Biological activity: Active against many fungi 

 but not bacteria. Examples of minimal inhibitory 

 concentrations, in /xg per ml: C. albicans, 1.56; 

 Aspergillus niger, 1.56; Microsporum audouini, 

 3.13; Sacch. cerevisiae, 6.25. Fungicidal effect ob- 

 served against C. albicans and Cryptococcus neo- 

 formans. Weak inhibition of Trichomonas vagi- 

 nalis. Some effect in vivo against C. albicans 

 infection in mice (2) . 



Toxicity: LDjo (mice) 89.6 mg per kg intrave- 

 nously (2). 

 References: 



1. Matsuoka, M. and Umezawa, H. J. Anti- 



biotics (Japan) ISA: 114-120, 1960. 



2. Matsuoka, M. J. Antil)iotics (Japan) 13A: 



121-124, 1960. 



Unamycin B 



Produced by: Streptomyces fungicidicus. 



Synonyms: Related to toyocamycin, antibiotic 

 E 212, and vengicide. 



Method of extraction: Culture-filtrate adjusted 

 to pH 8.0 and passed through a column of Duolite- 

 S30 (H+ form). Elution with 80 per cent aqueous 

 acetone containing 2 per cent HCl. Eluate concen- 

 trated in vacuo. Concentrate adjusted to pH 9.0 

 and extracted with butanol. Back-extraction in 

 water at pH 2.0. Methanol added to the aqueous 

 extract and the mixture cooled, resulting in the 

 formation of crude crystals. Recrystallization 

 from water. 



Chemical and physical properties: Basic sub- 

 stance. White needle-shaped crystals; m.p. 236- 

 238°C (decomposition). Soluble in acidic water, 

 acidic alcohol, and formamide. Slightly soluble in 

 methanol, ethanol, butanol, and ethjd acetate. 

 Insoluble in dioxane, toluene, acetone, ligroin, 

 hexane, benzene, carbon tetrachloride, and glacial 

 acetic acid. Light -absorption maxima in 0.05 A^ 

 HCl at 236 (Ell, 626.5) and at 273 m^ (E\'L 458.8). 

 Infrared absorption spectrum given in reference 1. 

 C = 46.6%,; H = 4.35%; N = 22.52%. [a]'^ = 

 — 43° (c = 1 per cent in acidic methanol). Rf, using 

 90 per cent aciueous acetone = 0.89. Negative 

 FeCls , Millon, Fehling, Tollen, Schiff, and Saka- 

 guchi tests. Decolorization of permanganate and 

 bromine solutions. Green Molisch reaction (1). 



Biological activity: Narrow antifungal spectrum. 

 Examples of minimal inhibitory concentrations, in 

 Mg per ml. C. albicans, 3.13; Cryptococcus neo- 

 formans, >100; Aspergillus niger, >100; P. chryso- 

 genum, 3.13. Very little activity against most bac- 

 teria. Active against M. phlei (3.13 fxg per ml) (2). 



Toxicity: LD50 (mice) 10 mg per kg intrave- 

 nously. Delayed toxicity observed. 



References: 



1. Matsuoka, M. and Umezawa, H. J. Antibi- 



otics (Japan) 13A: 114-120, 1960. 



2. Matsuoka, M. J. Antibiotics (Japan) 13A: 



121-124, 1960. 



Valinoniycin 



Produced by: Streptomyces fulvissimus (1). 

 Synonyms: Aminomycin (3, 5). Similar to amido- 

 mj-cin . 



