DESCRIPTIONS OF ANTIBIOTICS 



407 



Vulgarin 



Produced by: Slreptouiyrcs sp. resembling S. 

 flavochromogenes . 



Method of extraction: Mycelium extracted with 

 organic solvents. 



Chemical and physical properties: White crystal- 

 line substance; m.p. 1()4-1G5°C. Soluble in various 

 organic solvents. Insoluble in acidified water and 

 petroleum ether. Positive FeCls test. Ultraviolet 

 absorption spectrum maxima at 227 and 338 m^u 

 (solvent not stated). Infrared data given in ref- 

 erence 1. 



Biological activity: Active on yeasts. 



Reference: 1. Hosoya, S. et al. Japan. J. Bac- 

 teriol. 9, 1954. 



Xa 11 1 hit' ill 



Produced by: Streptomyces xanthochroviogenes. 



Method of extraction: Broth-filtrate extracted 

 with ethyl acetate at acidic pH. 



Chemical and physical properties: Fine yellow 

 needles. Decomposes at 211-213°C. Ultraviolet ab- 

 sorption spectrum maximum at 270 niyu (e = 

 35 ,235) (methanol) or at 2fi0 (e = 33,935) and 325 

 niM (e = 23,306) (in 0.1 M KOH). Infrared spec- 

 trum given in reference 2. [a]^ = -f319° (c = 0.25 

 per cent in acetone). Positive Ehrlich aldehyde 

 and FeClj tests and tests for indole ring. Negative 

 Fehling (hot) test. Methanolic solution forms a 

 reddish orange precipitate with Brady's reagent. 

 No reaction with phosphomolybdic acid or sodium 

 molybdate. C = 57.80%; H = 5.70%; N = 5.19%. 

 CisHisNOs . Biological activity is reduced in al- 

 kali. Steam distillation with 40 per cent H2SO4 

 gives a monobasic, volatile acid, possibly acetic. 

 Oxidation gives succinic acid. No amino, nitro, 

 or carbonyl amide groups. May contain a 6-lactone 

 ring. 



Biological activity: Slightly active at 10 to5();ug 

 per ml on Penicilliiiiii, Rhizopus, Aspergillus, 

 Tor Ilia, Staph, aureus, and B. subtilis. Inactive on 

 Sacch. sake, gram-negative bacteria, and myco- 

 bacteria. 



Toxicity: LDbo (mice) 105 mg per kg intraperi- 

 toneally. 



References: 



1. Arishima, M. et al. J. Agr. Chem. Soc. 



Japan 30: 469-471, 1956. 



2. Sekizawa, Y. and Miwa, K. J. Agr. Chem. 



Soc. Japan 3(»: 471-474, 1956. 



Xanlhoniycins 



Produced by: Streptomyces sp. (1, 2, 8), S. rutger- 

 sensis (4), and S. pseudogriseolus (9). 



Synony)us: Antil)iotic H 1159 (4), protomycin, 

 antibiotic 534 (9). 



Method of extraction: I. Adsorbed from broth- 

 filtrate at pH 7.5 to 8.0 on Norite containing 1 per 

 cent Celite 545, and filtered. Filter cake washed 

 with butanol -saturated water and eluted with 0.1 

 N HCl saturated with butanol. Eluate concen- 

 trated in vacuo, pH adjusted to 7.0 to 7.5, filtered, 

 and extracted with chloroform. Back-extracted 

 into water at pH 2.0. Acjueous extract concen- 

 trated in vacuo and antibiotics precipitated as 

 picrates or helianthates. Purification by counter- 

 current distribution (chloroform-1 M phosphate 

 liuffer at pH 4.4) to give two major components, 

 A and B, and a minor one, C. Component A pre- 

 cipitated as the reineckate and recrystallized 

 from 95 per cent ethanol, then prepared as the 

 hydrochloride (1). II. Extracted from broth- 

 filtrate with ethylene dichloride at pH 7.0. Back- 

 extracted into 0.01 M HCl, then into ethylene di- 

 chloride at pH 7.8, and then back into 0.01 N HCl. 

 Process repeated. Freeze dried. Purified by coun- 

 tercurrent distribution (ethjl acetate-aciueous 

 phosphate buffer, pH 6.2 to ().3). Precipitated as 

 the leineckate (2). Countercurrent distribution 

 can also be carried out in a chloroform-0.5 M cit- 

 rate buffer (pH 4.2) system. Active fractions ex- 

 tracted with chloroform and evaporated to dry- 

 ness. Free base prepared by precipitation from 

 chloroform with ether (6). III. Culture-broth ad- 

 justed to pH 4.0, filtered, then extracted with tri- 

 chloroethylene at pH 8.5 to 9.5. Extract concen- 

 trated at 2()°C, then back-extracted into water at 

 pH 3.0 to 3.5. Afjueous extract extracted with 

 chloroform at jjH 6.0, then back-extracted into 

 water at pH 2.0 to 2.5. Crystallized from 10 jier 

 cent water-propanol on addition of acetone. Puri- 

 fied by countercurrent distribution (trichloroeth- 

 ylene and 0.5 M sodium, citrate at pH 6.0) . Aqueous 

 phases adjusted to pH 9.0 to 9.5. The organic phase 

 washed with water at pH 9.0 to 9.5, then extracted 

 with 0.25 N acetic acid (8, 10). 



Chemical and physical properties: Basic sub- 

 stances, possibly containing a benzociuinone-like 

 system (6). Complex contains three or four com- 

 ponents (1, 2). Component A believed to be trans- 

 formed into other active components under acidic 

 conditions during purification (6). Rao and Peter- 

 son (6) reported that they had isolated the free 

 base of A, but Dougall (10) showed that it was an 

 irreversibly degraded mixture of products having 

 little or no biological activity, containing a large 

 amount of a biologically inactive neutral material, 

 a small amount of ethanolamine, and a biologically 

 active basic fragment which l)ehaved like the 



