DESCRIPTIONS OF ANTIBIOTICS 



335 



Chemical and physical properties: Bright yellow 

 powder. Pentaeiie. Contains two closely related 

 components. Soluble in methanol, ethanol, n- 

 butanol, tert-hiitanol-water (volume per volvmie), 

 ethylene glycol, monomethyl ether, N-N-dimethyl 

 sulfoxide, and pyridine. Partially soluble in tert- 

 liutanol, water, and chloroform. Insoluble in ace- 

 tone, benzene, and toluene. Ultraviolet absorption 

 spectrum maxima of both are at about (298), 317, 

 333, and 350 m.a (methanol) or 302 to 308, 322.5, 338 

 (£'icm 3S8), and 358 m/i (pyridine). Rf values of two 

 components are 0.55 and 0.85 by ascending paper 

 chromatography (methanol -butanol -water, 



1:10:10). 



Biological activity: Active on yeasts, fungi, and 

 certain gram-positive bacteria and mycobacteria. 

 \'ery active on Cuccidioides iiniriitis. 



Reference: 1. Steinman, I. D. Thesis, Rutgers 

 University, 1958. 



Peiitacne Antifungal Anlibiolic II 



Produced by: Streptoinyces sp. 



Chemical and physical properties: Amphoteric 

 pentaene. Yellow substance. Believed to contain a 

 carbohydrate moiety. Approximately one half the 

 nitrogen present is amino N. 



Biological activity: Active on fungi. Active 

 at high concentrations on gram-positive bacteria. 

 Hemolytic in high concentrations. Activity 

 affected l)y serum. 



Toxicity: Very toxic for mice. 



Reference: 1. Brown, R. and Hazen, E. L. 

 Abstr. Communs. Symposium on Antibiotics, 

 Prague 4-5, 1959. 



I'enlani> cin 



Produced by: Streptoinyces penticus resembling 

 S. rubrireticuli (1), S. pentaticus (2). 



Synonyms: Related to fungicliromin, Hlipin, and 

 moldcidin B. 



Method of extraction: Mycelium extracted with 

 90 per cent methanol, then 80 per cent methanol. 

 Extracts concentrated in vacuo; a gelatinous 

 precipitate forms on standing at room tempera- 

 ture. Dissolved in hot methanol; solution concen- 

 trated in vacuo until a l)rownish red precipitate 

 appears. Filtration while hot followed by con- 

 centration of filtrate to '9 volume. Crystals 

 ])recipitate on standing. Recrystallization from 

 methanol (1). 



Chemical and physical properties: Pentaene: 

 Pale yellow needles; m.p. 236-237°C (decomposi- 

 tion). Very soluble in pyridine and dimethyl- 

 formamide. Moderately to slightly soluljle in 

 methanol, ethanol, isopropanol, Ijutanol, methyl 



Cellosolve, acetone, and ethylene glycol. Nearly 

 insoluble in water, ether, ethyl acetate, amyl 

 acetate, l)enzene, chloroform, and carbon disulfide. 

 Ultraviolet absorption spectrum maxima at 322 

 (ETcm 899), 338 (ETlm 1450), and 356 m^ (£'l'^"m 

 1500), and a shoulder at 308 to 313 m^. Infrared 

 spectrum given in reference 1. Gives a deep piuple 

 color in H>S()4 . Reduces ToUen's reagent very 

 slowly, and decolorizes Br water. Negative Fehling 

 and FeCl;; tests (1). Very stable at pH 4 to G at 

 37°C; unstable at pH 1 and pH 10. C = 61.5%; 

 H = 8.4%. Chromophoric moiety is 2-methyl-2,4, 

 6,8,10-dodecaj)entaenedial, as in fiuigichromin 

 (2). 



Biological activity: Active at 0.2 to 4 ng per ml 

 on fungi and yeasts. No activity on bacteria (1). 

 Inhibits Ridgeway osteogenic sarcoma (3). 



Toxicity: hD-^n (mice) 33.3 mg per kg intra- 

 peritoneally, and 1624 mg per kg orally (1). 



References: 



1. Umezawa, S. et al. J. Antibiotics (.Japan) 



IIA: 26-29, 1958. 



2. Umezawa, S. et al. .1. Antibiotics (.Jajjan) 



UA: 273, 1958. 



3. Sugiura, K. et al. Cancer Researcli 18: 



66-77, 1958. 



4. Ogawa, H. et al. J. Antibiotics (Japan) 



13 A: 353-355, 1960. 



Perini> cin 



Produced by: Streptomyccs coclicotor var. aniin- 

 ophilus (1). 



Synoni/ms: Antil)iotic 1968 (2), antil)i()tic NC 

 1968 (1). 



Method of extraction: Extraction of the myceliiun 

 with methanol at a slightly alkaline pH (1). 

 Crude extracts can be ptu-ified by dissolving in a 

 hot methanol-ethyl acetate (5:1) mixture. Cooling 

 causes precipitation. Precipitate centrifuged and 

 washed with ethyl ether. Wet precipitate dissolved 

 in n-butanol (1:1), and pH adjusted to 10 to 11. 

 Butanol layer separated, washed with water until 

 neutral, and concentrated in vacuo. Precipitation 

 occurs during concentration and is completed by 

 adding ethyl ether to the concentrate. Further 

 purification by countercurrent distribution in 

 ethyl acetate-pyridine-water (6.5:3.5:8.3; partition 

 coefficient, 2.17). 



Chemical and physical properties: Heptaene. 

 Light-absorption maxima at 361, 383, and 406 

 mju. E\°i^ at 383 m^ = 1000 in methanol. De- 

 composes slowly upon heating. Insoluble in water, 

 petroleum ether, ethyl acetate, and benzene. 

 Soluble in aqueous lower alcohols, pyridine, tetra- 

 hvdrofvu-an, acetone, and dioxane. Soluble in hot 



