DESCRIPTIONS OF ANTIBIOTICS 



279 



Hclianthatc: Red platelets (from dilute methanol) ; 

 in. p. 2[)5-215°C (decomposition). Hydrochloride: 

 Hygroscopic, colorless powder. Soluble in water 

 and methanol. Less soluble in ethanol. Insoluble 

 in acetone, ethyl acetate, ether, and petroleum 

 ether, [a]^ = +16.0° ± 0.4° (c = 3.25 per cent in 

 water). Molecular weight, 1650 ± 165. 



Biological activity: Active against gram-positive 

 and gram-negative bacteria. No effect on entero- 

 cocci, pneumococci, or Streptococcus viridans. 

 Active on Endamoeha histolytica in rats (2). 



Toxicity: Nephrotoxic (2). 



References: 



1. Lindenbein, W. Arch. Mikrobiol. 17: 301- 



383, 1952. 



2. Brockmann, H. and Musso, H. Naturwiss- 



enschaften 41:451-452,1954. 



3. Brockmann, H. and Musso, H. Chem. Ber. 



87: 1779-1799, 1954. 



4. Brockmann, H. and Musso, H. Chem. Ber. 



88: 648-661, 1955. 



5. Brockmann, H. and Colin, R. Chem. Ber. 



92: 114-130, 1959. 



Graiialiciii 



Produced by: A variety of Streptoun/ces olivaceus 

 which produces a soluble pigment. 



Method of extraction: Broth-filtrate adjvisted to 

 1)H 3 with dilute HCl. Extracted with ethyl ace- 

 tate. Extract concentrated in vacuo. Addition of 

 petroleum ether precipitates crude granaticin. 

 Purified bj' chromatography on a cellulose column. 

 Cellulose suspended in benzol-saturated formam- 

 ide; column pretreated with a benzol solution of 

 8-hydroxyquinoline, followed by washing with 

 formamide-saturated benzol. A benzol solution of 

 crude granaticin applied to column. Elution with 

 formamide-saturated benzol. Four pigmented 

 substances, brown-red, violet-blue (granaticin), 

 blue, and orange are distinguished, in that order. 

 Eluate concentrated to dryness, dissolved in ethyl 

 acetate, and precipitated with petroleum ether. 

 Recrystallization from acetone. 



Chemical and physical properties: Tricyclic 

 tetrahydroxyquinone dicarboxylic acid. Small 

 granular red crystals; m.p. 204-206°C (decomposi- 

 tion). Indicator properties: red at acid pH, blue at 

 alkaline pH. C22H.20O10 : C = 59.40%; H = 4.72%; 

 O = 35.95%; C—CH., = 7.31%. Crystallographic 

 data given in reference 1. Kuhn-Roth oxidation 

 yields more than 1 mole of acetic acid. Ultraviolet 

 absorption spectrum maxima (rectified alcohol): 

 223, 286 (496), 532, and 576 uim- Infrared spectrum 

 given in reference 1. On acetylation gives a tetra- 

 acetyl derivative, m.p. 242-243°C (gas generated 



over 250°C). [a if," = +100° (c = 0.818 per cent in 

 chloroform). Absorption spectra given in refer- 

 ence 1. 



Biological activity: Active on gram-positive bac- 

 teria and Trichomonas foetus. Slightly active on 

 Pasteurella pestis, Vibrio ro)n»ta, M. tuberculosis, 

 and Endamoeba histolytica. 



Toxicity: 250 mg per kg subcutaneously is 

 lethal for mice. 



Reference: 1. Corbaz, R. et al. Helv. Chim. 

 Acta 40: 12()2-12l)9, 1957. 



(iras.serioniycin 



Produced by: Streplomyces lavendulae (1) and 

 S. griseolavendus (2). 



Method of extraction: Adsorbed from broth- 

 filtrates on charcoal at alkaline pH. Eluted with 

 80 per cent methanol at pH 2.0. Eluate concen- 

 trated in vacuo, taken up in anhydrous methanol, 

 and precipitated with acetone. Purified by adsorj)- 

 tion on an ion exchange resin, and by salt conver- 

 sion. 



Chemical and physical properties: Basic sub- 

 stance belonging to the streptothricin group. Base: 

 Soluble in water, slightly solul)le in methanol and 

 ethylene glycol. Insoluble in other organic sol- 

 vents. No specific absorption in ultraviolet light. 

 Infrared spectrum given in reference 2. Positive 

 Molisch, Fehling, Tollen, and ninhydrin tests. 

 Negative biuret, Sakaguchi, xanthoproteic, Mil- 

 lon, Adamkiewicz, Liebermann, Neubauer, and 

 Fed,, tests. Hydrochloride: Faintly yellow powder. 

 Soluble in water and methanol; insoluble in or- 

 ganic solvents. Molecular weight, 610. Heiianthate: 

 m.p. 215-225°C (decomposition). Reineckate: m.)). 

 187-190°C (decomposition). C = 22.04%; H = 

 4.51%; N = 19.35%; Cr = 11.22%. No figures 

 given for S. 



Biological activity: Active on gram-negative and 

 gram-positive bacteria, but not on cultures of 

 E. coli resistant to streptothricin, neomycin, or 

 grisein. Active on fungi and Sacch. cerevisiae, but 

 not on other yeasts. Delays death of silkworms 

 infected with silkworm jaundice virus (1, 2). 



Toxicity: Silkworms tolerate injections of 5 jug 

 (2). 



References: 



1. Ueda, K. et al. J. Antibiotics (Japan) 8A: 



91-95, 1955. 



2. Sumiki, Y. et al. Japanese Patent 6296, 



August 15, 1957. 



Grisaniine 



Produced by: Streplomyces griseoflavus. 



Method of extraction: Broth-filtrate adjusted to 



