DESCRIPTIONS OF ANTIBIOTICS 



387 



Celite, and eluant (chloroform) concentrated to 

 dryness. Residue dissolved in methanol and passed 

 through activated alumina. Most active eluates 

 concentrated to diyness. Residue dissolved in 

 chloroform and treated with petroleuni ether to 

 incipient turhidity. Crystals form after 72 hours 

 at 10°C. 



Chemical and physical properties: Neutral, yel- 

 low-brown crystals; m.p. 166-178°C. C = 64.88%; 

 H = 8.38%; N = 4.25%; S = 1.80%. Ultraviolet 

 absorption peak at 275 to 280 myu (ethanol). In- 

 frared spectrum given in reference 1. Nitroprus- 

 side (for SH groups), azide-iodine (for amino S), 

 ninhydrin, Sakaguchi, maltol, FeCls , Fehling, 

 biuret, nitrochromic acid, 2,4-dinitrophenylhy- 

 drazine, and anhydrous aluminum chloritle tests 

 negative. Decolorizes a KMn04-acetone solution 

 in the cold. Soluble in chloroform, acetone, lower 

 alcohols, 1,4-dioxane, pyridine, glacial acetic 

 acid, and ethyl acetate. Insoluble in water, 10 

 per cent HCl, 10 per cent NaHCOs , CCU , diethyl 

 ether, and petroleum ether. Slightly soluble in 

 10 per cent NaOH. [a]f = -58.5° (c = 0.51 per 

 cent in chloroform) . Solutions lose 25 to 50 per cent 

 of their potency in 24 hours in water or buffered 

 solutions (pH 5 to 8) at 25 and 37°C. At 7°C, solu- 

 tions lose potency slightly during 10 days. Dry 

 powder stable at 7 and 25°C for more than 1 year. 

 Purified but not crystalline product was found to 

 have four fractions, with Rf values of 0.0, 0.06, 

 0.13, and 0.30 on descending paper chromotog- 

 raphy with aqueous 3 per cent NH4CI solution (1). 



Biological activity: Active on gram-positive and 

 gram-negative bacteria, mycobacteria, and fungi. 

 Strongly bactericidal. Activity unaffected by 

 saliva or serum (1) . Has antitumor activity against 

 the ascitic form of Gardner lymphosarcoma and 

 sarcoma 180, but is not active on the solid form of 

 sarcoma 180 or C3HBA adenocarcinoma in mice 

 (2). 



Toxicity: LD.=,u (mice) 5 mg per kg intraperi- 

 toneally, 10 to 25 mg per kg orally (1), 0.5 to 0.9 

 mg per kg intravenously (2). 



References : 



1. Zief, M. et al . Antibiotics Ann. 1957- 



1958, pp. 886-892. 



2. Pugh, L. H. et al. Antibiotics Ann. 1957- 



1958, pp. 972-976. 



Taitoniyciii 



Produced by: Streptoniyces afghaniensis , said to 

 resemble S. collinus and <S. erythrochromogenes (1). 



Method of extraction: Present in both mycelium 

 and broth. Minor amount in l)roth precipitated 

 by adjusting to i)H 4.0. All solids from filtration 



extracted with methanol at 30-35°C with stirring. 

 Extract flash-evaporated, then concentrated in 

 vacuo. Aqueous residue extracted with ethyl ace- 

 tate. Extract evaporated under reduced pressure, 

 residue washed with isetroleum ether, and dried. 

 Purified by chromatographj^ from acetone, with 

 80 per cent methanol as developer. Acidification 

 to pH 4.0 precipitates taitomycin from active 

 fractions. Further purified by covmtercurrent dis- 

 tribution (pH 8.3 pho.sphate buffer-methanol- 

 ethyl acetate-chloroform, 1:1:1:1) (1). 



Chemical and physical properties: Pale yellowish 

 brown or reddish powder (1). Soluble in pyridine, 

 glacial acetic acid, methanol, ethanol, acetone, 

 ethyl acetate, and alkaline water. Slightly soluble 

 in ether and benzene. Insoluble in petroleum ether, 

 ligroin, and acidic water. Ultraviolet absorption 

 spectrum maxima at 330 and 420 ni/u (c = 2 per 

 cent in methanol). Infrared absorption spectrum 

 given in reference 2. Positive Fehling test. Elson- 

 Morgan test becomes positive on mild acid hy- 

 drolysis. Questionable biuret and Millon tests. 

 Acid hydrolysates give a positive ninhydrin test. 

 Data on paper chromatography given in reference 

 2. C = 53.57%; H = 4.87%; N = 9.50%; ash = 

 2.8%. No data on S, halogen, or Fe content. 



Biological activity: Active on gram-positive 

 bacteria and Neisseria, but not on Hemophilus, 

 Klebsiella, or other gram-negative organisms. Not 

 active on fungi, yeasts, or trichomonads. No anti- 

 tumor activity (2). Not affected by serum, but 

 has hemolytic properties (2). Active in mice on 

 D. pneumoniae (2), but not on Toxoplasma gondii 

 (3). Active on Rickettsia mooseri (chick embryos) 

 and R. orientalis (mice) (3). No cross-resistance 

 with erythromycin or oleandomycin (3). Active in 

 chick embryos and mice against psittacosis organ- 

 ism. Ineffective in mice infected with Rift Valley 

 fever virus (4). 



Toxicity: LD50 (mice) 200 to 250 mg per kg 

 intravenously, > 1000 mg per kg intraperitoneallj' 

 (3). 



References: 



1. Shimo.M. et al. J. Antil)iotics (Japan) 12A: 



1-6, 1959. 



2. Tomosugi, T. et al. J. Antibiotics (Japan) 



12A: 7-11, 1959. 



3. Komatsu, N. J. Antibiotics (Japan) 12A: 



12-16, 1959. 



4. Komatsu, N. et al. J. Antibiotics (Japan) 



12 A: 173-176, 1959. 



Teloinycin 



Produced by: Streptoniyces sp. (1). 

 Synonym: Antiliiotic C 159. 



