DESCRIPTIONS OF ANTIBIOTICS 



191 



treatment with ion exchange resins, and chroma- 

 tography on ahnnina. May be preciijitated from 

 a concentrated chloroform-extract by addition of 

 cyclohexane (3). 



Chemical and physical properties: Basic sub- 

 stance. Long white needles; m.p. 140-141 °C. Can 

 be distilled in vacuo at a few degrees above its 

 melting point. Soluble in lower alcohols, esters, 

 ketones, chloroform, and dilute ac^ueous acids. 

 Moderately soluble in water. Low solubility in 

 ether, carbon tetrachloride, and hydrocarbons 

 (3, 4). X^'ST^ 224 mu (e = 10,800), 277 m^ U = 

 1800), and 283 m^ (e = IfiOO). Infrared data given 

 in reference 4. [a]'if = —30° (c = 1 per cent meth- 

 anol). Aqueous solutions lose jjotency slowly at 

 acid pH, more rapidly at alkaline pH. Powder is 

 stable C14H19NO4 • C = 63.51' t; H = 7.21^:^; N = 

 5.22%. Salts are very soluble in water (3, 4). 



Biological activity: Active on protozoa (1), some 

 fungi, Candida stellatoides, C. albicans, and Sac- 

 charomyces cerevisiae. Slightly active on gram- 

 positive and gram-negative bacteria. Active in 

 vitro and in vivo (mice) on Trichomonas foetus 

 and T. vaginalis (3, 4, 7, 8). Some activity on 

 Endamoeba histolytica in vitro (1) and in guinea 

 pigs (5). Some activitj- on Nosenia disease in bees 

 (9). Active on powdery mildew of beans {Erysiphe 

 polygoni) (11), of roses (Sphaerotheca) (12), and 

 of wheat (E. graminis f. sp. triiici) (15). Also 

 active on downy mildew of lima beans (Phyto- 

 phthora phaseoli) (10) and broccoli (Peronospora 

 parasitica) (13). 



Toxicity: LDjo (mice) 140 mg per kg intraven- 

 ously, 148 mg per kg orally, 400 mg per kg intra- 

 peritoneally. LDjo (rats) 72 mg per kg orally, 

 107 mg per kg intravenously, 345 mg per kg intra- 

 peritoneally. Causes emesis in cats and dogs. 

 Tolerated by monkeys in daily oral doses up to 

 64 mg per kg over a 32-week period (7). 



Utilization: Effective, in a limited clinical 

 study, against vaginal infections with Tricho- 

 monas vaginalis (6). 



References: 



1. Lynch, J. E. et al. Antibiotics & Chemo- 



therapy 4: 844-848, 1954. 



2. Sobin, B. A. and Tanner, F. W.. Jr. J. 



Am. Chem. Soc. 76: 4053, 1954. 



3. Tanner, F. W. et al. U. S. Patent 2,691,618, 



October 12, 1954. 



4. Tanner, F. W., Jr. et al. Antibiotics Ann. 



809-812, 1954-1955. 



5. Lynch, J. E. et al. Antil)iotics Ann. 813- 



819, 1954-1955. 



6. Frye, W. W. et al. Antil)iotics Ann. 820- 



823, 1954-1955. 



7. Gardocki, J. F. el al. Antibiotics & Chemo- 



therapy 5: 490-495, 1955. 



8. Lynch, J. E. et al. Antibiotics & Chemo- 



therapy 5: 508-514, 1955. 



9. Katznelson, H. and Jamieson, C. A. Glean- 



ings Bee Culture 83: 275-277, 1955. 



10. Zaumeyer, W. J. and Webster, R. E. Phy- 



topathology 46: 470, 1956. 



11. Zaumej'er, W. J. Antibiotics Ann. 1015- 



1018, 1955-1956. 



12. Kirby,R. S. Plant Disease Reptr. 41:534- 



535, 1957. 



13. Natti, J. J. Plant Disease Reptr. 41: 



780-788, 1957. 



14. British Patent 768,364, February 13, 1957. 



15. Powers, H. R., Jr. Phytopathology 48: 



474-477, 1958. 



Antibiotic l-81d-ls 



Produced by: Streptouiyces albus. 



Synonym: Has properties in common with cam- 

 phomycin. 



Method of extraction: From 70 to 95 per cent of 

 the antibiotic is present in the mycelium. Myce- 

 lium separated from the broth and extracted with 

 methanol, ethyl acetate, n-butanol, diethyl ether, 

 benzene, chloroform, or methyl isobutyl ketone. 

 Extract concentrated by distillation under re- 

 duced pressure. Residual acjueous slurry extracted 

 with diethyl ether. Extract concentrated, then 

 treated with n-pentane. Residue which precipi- 

 tates is then dissolved in hot ethyl acetate, from 

 which, after addition of hexane and cooling, the 

 crude antibiotic precipitates. Recrystallized from 

 ethyl acetate-aliphatic hydrocarbons, dioxane- 

 water, ethanol-water, or chloroform-benzene mix- 

 tures. 



Chemical and physical properties: Small colorless 

 needles; m.p. 140-141°C. Soluble in lower alcohols, 

 chloroform, ethyl acetate, dioxane, ether, and 

 acetone. Slightly soluble in benzene. Insoluble in 

 water, aliphatic hydrocarbons, cold 5 per cent 

 NaOH, and cold 5 per cent HCl. [0]^ = -29.8° 

 (c = 1.14 per cent in acetone). Ultraviolet absorp- 

 tion spectrum maxima at 244 and 284 m/x (aqueous, 

 acidic, or dry methanol). Addition of alkali shifts 

 the 284 niM peak to 274 m/u. Infrared absorption 

 spectrum given in reference 1. Heating with 5 per 

 cent NaOH causes a gas of basic pH to be given 

 off. Red in concentrated H0SO4 and lavender in 

 cold 85 per cent H3PO4 . Positive KMn04 test. 

 C38H63-65O12N: C = 63.10%; H = 8.87%; O = 

 26.48% ;N = 1.92%. 



Biological activity: Active on D. pneumoniae and 

 Sarcina lutea at 6.3 Mg ppi" nil, Streptococcu.<i pyo- 



