184 



DESCRIPTIONS OF ANTIBIOTICS 



per cent tri ethyl amine, methanol-1 per cent tri- 

 ethylamine, acetone, or an ethyl acetate-acetone - 

 water mixture (5:1:0.5). Ethyl acetate-extracts 

 are concentrated in vacuo. To the resulting oily 

 brown residue is added a saturated solution of 

 tannin to precipitate impurities, and the whole 

 filtered. Water is added to the filtrate and mixed, 

 and the aqueous and organic phases separated. 

 To the aqueous phase NaCl is added to satura- 

 tion, to salt out an additional amount of the or- 

 ganic phase. Both organic phases are extracted 

 with methanol, extract concentrated in vacuo, 

 and lyophilized to give a brown oil (3). 



Chemical and physical properties: Liglit brown 

 clear oil. Ultraviolet absorption spectnun maxi- 

 mum at 270 m/i, with a small peak at 350 niju 

 (methanol). Does not form active precipitates 

 with picric acid, p-toluenesulfonic acid, methyl 

 orange, ammonium reineckate, resorcinol, or pro- 

 caine HCl. Rf values in various systems of paper 

 chromatography are given, and are said to differ- 

 entiate the antibiotic from those given in the key 

 system of Ammann and (iottlieb (4). Unstable 

 at acid pH; most stable at pH (5.0; 50 per cent 

 inactivated after 3 hours at 100°C (3). 



Biological activity: Active on Candida. Not 

 active on bacteria (2). 



References: 



1. Woznicka, W. et al. Med. Doswiadczalna i 



Mikrobiol. 9: 57-62, 1957. 



2. Woznicka, W. el al. Med. Do.swiadczalna i 



Mikrobiol. 9:293-308,1957. 



3. Woznicka, W. et al. Med. Doswiadczalna i 



Mikrobiol. 9:441-450,1957. 



4. Ammann, A. and Gottlieb, D. Apjil. Micro- 



biol. 3: 181-18(j, 1955. 



Allhioiii}! ciii 



Produced by: Streptoniyces althioticus (I). 



Method of extraction: Broth adjusted to pH (i.O 

 and filtered. Filtrate extracted with butyl acetate 

 or butanol. Extracts concentrated in vacuo. Cool- 

 ing of residue precipitates althiomycin. Recrys- 

 tallized from ethyl Cellosolve. Can be adsorbed 

 from broth on clay and eluted with aqueous ace- 

 tone. Can also be extracted with ethanol, acetone, 

 or ethyl acetate from mycelium. 



Chemical and physical properties: White needles; 

 brown at r20-l(iO°C and decompose at 172-174°C. 

 Soluble in ethyl Cellosolve, dioxane, and pyri- 

 dine. Slightly soluble in acetone, methanol, buta- 

 nol, ethyl acetate, and butyl acetate. Insoluble 

 in water, ether, petroleum ether, and benzene. 

 [a];° = +20.3° (c = 1.33 per cent in methyl Cello- 

 solve). Ultraviolet absorption spectrum maxi- 



mum at 220 to 223 m^ {E]'cm 810) and a shoulder 

 at 285 to 290 m^ (£^IL 210) in 0.03 .V HCl contain- 

 ing 1 per cent methyl Cellosolve, or at 235 ni/x 

 {E\fm 611) and 300 to 305 m^ {E\'L 317) in 0.03 N 

 NaOH containing 1 per cent methyl Cellosolve. 

 Infrared spectrum given in reference 1. Positive 

 ninhydrin and Tollen tests. Negative FeCU , 

 Fehling, and Sakaguchi reactions. C15H14N4S2O6 : 

 C = 44.49%; H = 3.51%; N = 13.92%; 

 S = 14.77%. Stable at pH 5 to 7. 



Biological activity: Active on gram-positive and 

 some gram-negative bacteria, ])ut not on myco- 

 bacteria, Pr. vulgaris, Ps. aeruginosa, fungi, or 

 yeasts. Active in mice on D. pneumoniae and Sal. 

 typhosa. 



Toxicity: Mice tolerate 720 mg per kg int ra- 

 pe ritoneally. 



Reference: 1. Yamaguchi, H. et al. J. Anti- 

 l)iotics (Japan) lOA: 195-200, 1957. 



Aniaroniycin 



Produced by: Streptoniyces flavochromogenes. 



Synonym: Related to picromycin and griseo- 

 mycin. 



Method of extraction: Broth, adjusted to pH 

 7.5, is extracted with 1^ volume of benzene. Ben- 

 zene is extracted three times with pH 2.0 HCl 

 solution. HCl solution adjusted to pH 5.7 and 

 back-extracted twice with benzene. Benzene is 

 dried in vacuo and the crude residue taken up in 

 hot CS2 . When cooled, white prisms precipitate 

 out. Recrystallization from ethanol. 



Chemical and physical properties: Basic, bitter- 

 tasting prisms; m.p. 164.5-165°C. [a]" = +6.19° 

 (1 per cent in ethanol). Free base: C = 63.66%; 

 H = 8.73%; N = 3.0%; O = 24.61%. C25H39O7N. 

 Ultraviolet spectrum shows broad peak at ap- 

 proximately 220 m;Li. Infrared spectrum (CCU as 

 solvent) shows bands at 2.9, 3.4, 5.7, 6.1, 6.85, 

 7.2, 7.45, 7.85, 8.38, 8.60, 9.0, 9.25, 9.5, 10.15, 10.60, 

 and 11.3 m- Readily soluble in ether, chloroform, 

 and methanol. Soluble in benzene, toluene, ethyl 

 acetate, butanol, carbon tetrachloride, ethanol, 

 and warm carbon disulfide. Slightly soluble in 

 cold CS2 . Scarcely soluble in petroleum ether 

 and water. A yellow color develops when concen- 

 trated H2SO4 is added to an aqueous solution of 

 the antibiotic. Positive Fehling and Tollen tests. 

 Negative FeCla , Schiff, Sakaguchi, xanthopro- 

 teic, biuret, ninhydrin, and Molisch tests. Precipi- 

 tated from aciueous solution l)y picric acid and 

 reineckate salt; stable to heating at 100°C for 20 

 minutes at pH 2 and pH 7, and for 10 minutes at 

 pH 8. 



Biological activity: Activity limited to gram- 



