298 



DESCRIPTIONS OF ANTIBIOTICS 



Dihiidrostieptomycin B-HCl: m.p. 194-195°C 

 (decomposition, corrected), [a] ',', = —55° (c = 

 0.9 per cent in water) (2). 



Biological activity: Antimicrol)ial activity' in 

 vitro and in vivo is qualitatively .similar to strepto- 

 mycin, but quantitatively less active on a weight 

 basis (1, 3, t>). 



Toxicity: Intravenous toxicity similar to strep- 

 tomj^cin (4). 



References: 



1. Fried, J. and Titus, E. J. Biol. Chem. 168: 



391-392, 1947. 



2. Fried, J. and Stavely, H. E. J. Am. Chem. 



Soc. 69: 1549-1550, 1947. 



3. Rake, G. et al. Proc. Soc. Exptl. Biol. Med. 



65: 107-112, 1947. 



4. Heuser, L. J. ct al. J. Am. Chem. Soc. 70: 



2833-2834, 1948. 



5. Perlman, D. and Langlykko, A. F. J. Am. 



Chem. Soc. 70: 3968-3969, 1948. 



6. Waksman, S. A., ed. Streptomycin; nature 



and practical applications. The Williams 

 & Wilkins Co., Baltimore, 1949. 



7. Fried, J. and Stavely, H. E. J. Am. Chem. 



Soc. 74:5461-5468, 1052. 



Matanij ciii 



Produced by: Streptoniyces niatensis (1). 



Synonym: Very closely related to, and probably 

 the same as, althiomycin, differing only in the 

 reaction to Fehling test. 



Method of extraction: Broth -fill rate extracted at 

 pH 6.5 to 7.0 with ethyl acetate. Extract concen- 

 trated in vacuo and cooled to give precipitate. 

 Precipitate taken up in boiling acetone, decolor- 

 ized, concentrated in vacuo and cooled. Recrystal- 

 lized from ethyl acetate to give a mixture of mata- 

 mycin and "Compound I," a closely related but 

 antibiotically inactive substance. Purification and 

 separation of the two compounds by countercur- 

 rent distribution (acetone-water-ethyl acetate, 

 2.5:2:2). 



Cheniiccd and physical properties: Not strongly 

 acidic or basic. White crystalline substance; m.j). 

 173°C (decomposition). Very slightly soluble in 

 hot water, dioxane, methanol, ethanol, acetone, 

 and ethyl acetate. Insoluble in petroleum ether. 

 Ultraviolet absorption spectrum shows strong 

 absorption before 220 ni/x and a maximiun at 285 

 niM (ETcm 190) (methanol) or at 237 niyu (EHm 

 550) and 305 to 307 m^ (Elvira 270) (in 0.1 A' NaOH) . 

 Infrared spectrum given in reference 2. Unstable 

 at acid pH, being inactivated to the "Compound 

 I" also present in the fermentation broths. [a]o = 

 +36.6°; [a]«6 = +57.4°; [aUi = +65.4° (c = 0.11 



per cent in methanol). Positive Tollen, PV'hling, 

 bromine, KMn()4 , 2,4-dinitrophenylhydrazine, 

 and ninhydrin (after acid hydrolysis) tests. Nega- 

 tive Fed;) , Sakaguchi, and Ehrlich diazo tests. 

 Does not diazotize with nitrous acid. Rf values on 

 chromatograijhy are given in reference 2. Acid 

 hydrolysis products include cysteine, glycine, 

 serine, alanine, questionably arginine, and two 

 unidentified ninhydrin-positive substances. C = 

 43.95%; H = 4.06%; N = 14.45%; S = 13.57%. 

 No halogen (2). 



Biological activity: Active on gram-positive 

 bacteria at 0.5 to 5 ng per ml, E. coii at 50 fxg per 

 ml, and K. pneumoniae at 5 ng per ml. Inactive on 

 Ps. aeruginosa, Pr. vulgaris, and fungi (1). 



References: 



1. Margalith, P. et al. Antibiotics & Chemo- 



therapy 9: 71-75, 1959. 



2. Sensi, P. et al. Antibiotics & Chemotherapy 



9: 76-80, 1959. 



Mediocidiii 



Produced by: Streptomyces mediocidicus (1). 



Method of extraction: Mycelivun extracted with 

 acetone. Extract evaporated to drjmess in vacuo. 

 Residue extracted with methanol; ether added to 

 extract to give a precipitate (1). 



Chemical and physical properties: Hexaene. 

 Yellow powder. Very soluble in methanol; soluble 

 in ethanol; slightly soluble in water and acetone; 

 insoluble in benzene, ether, and petroleum ether 

 (1). x!^^'.^" 339 to 340, 356 to 357, and 377 to 378 (1). 



Biological activity: Active mainly on yeasts; 

 moderate activity against certain filamentous 

 fungi and gram-positive bacteria. Slight inhibition 

 of ascites development in mice inoculated with 

 Ehrlich carcinoma (1, 2). 



Toxicity: LD50 (mice) = 2 mg per kg intra- 

 peritoneally (1). Minimal concentration causing 

 HeLa cell degeneration is 200 fxg per ml (3). 



References: 



1. Utahara, R. et al. J. Antibiotics (Japan) 



7A: 98-103, 120-124, 1954. 



2. Nitta, K. e/ cd. J. Antibiotics (Japan) 8A: 



120-125, 1955. 



3. Nitta, K. Japan. J. Med. Sci. & Biol. 10: 



277-286, 1957. 



IVIegacidin 



Produced by: Streptomyces sp. resembling, but 

 not identical to, iS. fradiae. 



Method of extraction: Broth extracted with 

 ethylene chloride. Extract concentrated in vacuo. 

 Residue taken up in benzene. Benzene shaken 

 with acetic acid and concentrated to drvness. 



