270 



DESCRIPTIOXh! OF ANTIBIOTICS 



Referenre: 1. Cionq'alve.s de Lima, O. ct al. 

 Anais soc. biol. Pernainl)ueo 12: 9-17, 1954. 



Eurocidiii 



Produced by: Streptomyces albireticitli (4), S. 

 eurocidicus (2, 3), and Streptomyces sp. (6). S. 

 albiretiodi produces carbomycin, tertiomycin A, 

 and enteromycin (10). S. eurocidicus also produces 

 a eurocidin-like antibiotic (EI-I), as well as azo- 

 mycin and the tertiomycins. E-I may be more like 

 "pentaene antifungal antibiotic I." A Strepto- 

 myces sp. (6) also produces a eurocidin-like sub- 

 stance (E-II) and an actinomycin. 



Remarks: See also eurocidin-like antil)iotic. 



Method of extraction: Eurocidin: Extracted from 

 myceliiun with methanol. Crystallized from aque- 

 ous methanol (5). E-I: Broth-filtrate extracted 

 with butanol. Extract evaporated to dryness in 

 vacuo. Residue taken up in methanol and precipi- 

 tated by adding ether. Small amount present in 

 mycelium extracted with methanol (3). E-II: 

 Methanol extracts of mycelium evaporated to 

 dryness in vacuo. Residue taken up in ethyl ace- 

 tate. Extract evaporated to dryness in vacuo. 

 Chromatographed on alumina from an acetone 

 solution and developed with benzene, acetone 

 (15 per cent )-benzene, followed l)y acetone (30 

 per cent) -benzene, then acetone. Antibiotic eluted 

 with 50 per cent methanol (6). 



Chemical and physical properties: Pentaenes. 

 Eurocidin: Gray-white or cream-colored sub- 

 stance. Does not melt up to 300°C. Insoluljle or 

 sparingly soluble in water, butanol, methanol, 

 ethanol, ether, ethyl and butyl acetate, propylene 

 and ethylene glycol, and acetone. Soluble in acids, 

 alkalies, ])yridine, dimethyl sulfoxide, and hy- 

 drous organic solvents (1, 5, 7-9). Ultraviolet ab- 

 sorption spectrum maxima at 318, 332, and 350 m/j, 

 (ethanol) (1). [a]'^ = -200° (c = 0.25 per cent in 

 0.1 N HCI) and +22° (c = 0.25 per cent in 0.1 N 

 NaOH). Positive Fehling test. Negative biuret, 

 Molisch, and Sherivanov tests (5). Rf = 0.40 by 

 ascending paper chromatography (methanol- 

 butanol-water, 9:10:10) (8). C = 57.99%; H = 

 8.13%; N = 1.65%. No halogens or sulfur (5). 

 E-I: Soluble in water, methanol, and ethanol. 

 Very slightly soluble in acetone. Insoluble in ben- 

 zene, ether, and petroleum ether. Ultraviolet ab- 

 sorption spectrum maxima at 318, 333, and 351 

 m;u (3). E-II: White substance. Ultraviolet ab- 

 sorption spectrum maxima at 310 m^t (shoulder), 

 322.5 niM (E'lL 125), 338.5 mfx iE\°L 179), and 356.5 

 m/i (E\7,n 164) (6). 



Biological aiiirity: Eurocidin: Active on yeasts, 

 filamentous fungi, and certain protozoa, including 



Trichomonas rayinalis (1, 5). Active in mice on T. 

 vaginalis (9). E-I: Active on yeasts and fungi but 

 not on bacteria or A', asteroides (3). E-II: Active 

 on ('. albicans and ,4. niger at 25 to 50 ng per ml 

 (6). 



Toxicity: Eurocidin: LDso (mice) 22 mg per kg 

 intraperitoneally (1). E-I: LDs,, (mice) 36 mg per 

 kg (no route given) (3). 



References: 



1. Nakazawa, K. 72nd Meeting Japan. Anti- 



biotics Research Assoc. September, 1953. 



2. Okami, Y. et al. J. Antibiotics (Japan) 



7A: 98-103, 1954. 



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



7A: 120-124, 1954. 



4. Nakazawa, K. J. Agr. Chem. Soc. Japan 



29: 647-649, 1955. 



5. Nakazawa, K. J. Agr. Chem. Soc. Japan 



29: 650-652, 1955. 



6. Maeda, K. et al. J. Antiljiotics (Japan) 



9A: 125-127, 1956. 



7. Shibata, M. Japanese Patent 4995, 1956. 



8. Steinman, I. D. Thesis, Rutgers Univer- 



•sity, 1958. 



9. Hamada, Y. Osaka Daigaku Igaku Zassi 



7: 237-245, 1955. 

 10. Miyake, A. et al. J. Antil)iotics (Japan) 

 12A: 59-64, 1959. 



Eurocidin -I ike An lihiolic 



Produced by: Streptomyces sp. belonging to the 

 S. reticuli group. This organism also produces 

 netropsin and antibiotic 2814K. 



Method of extraction: Mycelium extracted with 

 butanol. 



Chemical and physical properties: Amorphous 

 yellow pentaene. Soluble in concentrated H2SO4 , 

 giving a blue-violet color. Ultraviolet absorption 

 spectrum maxima at 317, 332 to 333, and 350 m^u. 

 Has nitrogen content and solubility properties 

 similar to eurocidin, but does not show the [a]'^ = 

 — 200° (0.1 A' HCI) given for eurocidin. 



Biological activity: Active on Sacch . cerevisiae 

 at 1:400,000. 



Reference: 1. Thrum, H. Nat urwissenschaften 

 46: 87, 1959. 



Everici 11 



Produced by: Probably a Streptomyces. 



Method of extraction: Broth acidified with oxalic 

 acid to pH 2.0 and filtered. Broth neutralized with 

 NaOH and adsorbed on cation exchange resin. 

 Elution with 1.5 A' HCI. Neutralized eluate evapo- 

 rated to dryness under reduced pressure. Extrac- 

 tion of residue with methanol. Precipitation of 



