DESCRIPTIONS OF ANTIBIOTICS 



403 



Vengicide 



Produced by: StreptoDtyces vendargejisis which 

 also produces five or six other antibiotics, inchid- 

 iiig oxytetracycline. 



Synonyms: Simihir to toyocamycin, moniliii, 

 and unamycin B. 



Method of extraction: I. Whole culture acidified 

 to pH 2.2 and filtered. Adsorbed from filtrate by 

 activated carbon at pH (5.5 to 7.5. Eluted with 

 water-saturated butanol containing 1 per cent 

 j)henol at pH 1.5. Eluate concentrated in vacuo 

 at pH 2.5. Residue extracted with butyl or amy! 

 alcohol at pH 8 to 11. Back-extracted into water 

 at pH 1.5 to 2.5. Oxytetracycline present precipi- 

 tated with a ciuaternary ammonium base. Filtrate 

 extracted with butanol at pH 9 to 10, then re-ex- 

 tracted into water at pH 2. Adjustment of aqueous 

 extract to pH 4.0 to 5.0 gives vengicide. Decolor- 

 ized with carbon and reprecipitated from water. 

 II. Broth-filtrate obtained as above concen- 

 trated by evaporation, and extracted with butanol 

 or amyl alcohol at pH 8 to 11. III. Culture-fil- 

 trate obtained as in I, and treated with the ion 

 exchange resin Duolite S8() at i)H 2.0 to 2.5 to re- 

 move the oxytetracycline. Vengicide then purified 

 as in I or II. 



Chemical and physical properties: Amphoteric 

 substance. White monoclinic crystals; m.p. 241.5- 

 243°C. Slightly soluble in water (0.4 mg per ml at 

 room temperature), acetone, methanol, butanol, 

 and amyl alcohol. Insoluble in diethyl ether. Ul- 

 traviolet absorption .spectrum maxima at 2:38.5 

 and 273.5 m// (in 0.05 N HCl). Infrared sj^ectrum 

 given in reference 1. [a]', = — 51.()° (in 0.1 .V 

 HCl); pH of the saturated solution is about (i.3. 

 C = 47.05%; H = 4.85%; N = 23.25%,. C24H29- 

 OgNio . Crystallographic data given in reference 1. 



Biological activity: Active at 5 mg per ml on 

 Blastomyces sulfnreum, B. dermititidis^Histoplasiiia 

 capsulation . and ('. alhicans. Not active at 5 mg 

 per ml on Triclmphytun violaceum, Hormodendnnn 

 compact uiri, Sacch. cerevisiae, Cladosporium cii- 

 ciimerinuin, Fusari)im sp., and Verticillium dah- 

 liac. 



Reference: 1. British Patent 7(14,198, December 

 19, 195G. 



\ inacelin 



Produced by: Streptomyces sp. closely related to 

 S. albosporens. 



Method of extraction: Broth adjusted to pH 5.0; 

 filtered on paper to remove inert precipitate. Ad- 

 sorption on cation exchange resin, elution with 

 acetone. F^vajjoratiou of acetone, extraction of 



residual acpieous solution with ethyl acetate. 

 Evaporation in vacuo of the ethyl acetate leaves 

 a brown powder. The pure antibiotic can be crys- 

 tallizetl from a chloroform-ether mixture. 



Chemical and physical properties: Yellow plate- 

 let-shaped crystals; m.p. 157-158°C. Soluble in 

 ethjd acetate, butyl acetate, methanol, and ace- 

 tone. Slightly soluble in water. Insoluble in ether 

 and petroleum ether. Soluble in alkaline water, 

 with development of a violet color. More active 

 and more stable at pH 5.0 than at {)H 7.0 and 9.0. 

 Negative ninhydrin, Sakaguchi, and Millon re- 

 actions. Positive Molisch, FeCls , and Fehling 

 reactions. 



Biological activity: Active against certain gram- 

 positive bacteria [Staph, citreus, ('orynebacteriuni 

 diphtheriae) and mycobacteria. Inactive against 

 gram-negative bacteria and fungi. 



Toxicity: 5 mg per 15-gm mouse injected intra- 

 venously or intraperitoneally has no to.xic effect; 

 10 mg kills the mice. 



Reference: 1. Omachi, K. J. Antibiotics (Ja])an) 

 6A: 73-79, 1953. 



\ iolacetiii 



Prod-need by: Strcptoni yces s]). closely related to 

 S. purpeochroniogcncs. 



Method of extraction: Adsorption of antil)iotic 

 on diatomaceous earth at alkaline ])H (8.0 to 9.0). 

 Elution with 0.2 per cent HCl in acetone. Eluate 

 adjusted to pH (j.8 to 7.0 and evaporated in vacuo. 

 Brownish residue extracted with methanol. Meth- 

 anol evaporated to leave crude violacetin. Crude 

 violacetin purified further by chromatography on 

 tdumina. The column is loatled with an ethanolic 

 solution of crude violacetin ami eluted with 95 

 per cent ethanol. Violacetin can also be adsorl)ed 

 on Amberlite IRC-50 and eluted with 2.0 ])er cent 

 HCl in acetone (1). 



Chemical and physical properties: Basic anti- 

 l)iotic. Can be precijntated out of ethanolic solu- 

 tions as fine, light yellow, needle-shaped crystals. 

 Violacetin hydrochloride does not melt at 210°C. 

 Solul)l(' in water, methanol, and ethanol, but in- 

 solul)le or sparingly soluble in most other organic 

 solvents. Violacetin is precipitated out of acjueous 

 solutions l)y picric acid, Reinecke salt, and phos- 

 ])li()tungstic acid. Negative biuret, Sakaguchi, glu- 

 cosamine, xanthoproteic, Millon, Fehling, maltol, 

 and FeCls tests. Positive diazo and ninhydrin 

 tests. H = 0.74%,; C = 38.26%; N = 24.71^; ; CI = 

 9.33%, for the hydrochloride. No S present. Maxi- 

 mal light al)sorption in water at 293 irifx. Stable in 

 acidic solutions; unstable at alkaline reaction (1). 



Biological activity: Active against gram-positive 



