DEyCRIPTlONS OF ANTIBIOTICS 



313 



4. Sato, K. and Katagiri, K. Cheinothera})y 



5: 182-183. 1957. 



5. Miyakawa, T. et al. Japan. J. Microbiol. 



2: 53-62, 1958. 



6. Hinuma, Y. et al. Jajjan. J. MicTot)iol. 2: 



63-68, 1958. 



7. Hinuma, Y. et al. Japan. J. Microhiol. 2: 



117-125, 1958. 



8. An>^ai, O. Vims (Osaka) »: 174-181, 1958. 



jNarboniyciii 



Produced by: Streptomyces narbonensis. 



Method of extraction: Extraction of culture fluid 

 at pH 8.5 with ethyl acetate. Transferred into 

 dilute acetic acid. Re-extraction with ethyl acetate 

 after neutralization with sodium carbonate. Crude 

 l)ases are chromatographed over alumina. Crystal- 

 lization of active fractions from ether-petroleum 

 ether. 



Chetuical and pht/sical properties: Colorless 

 crystals; m.p. 113.5-115°C. |al„ = +68.5° (c = 

 1.35 per cent in chloroform). pK* about 7.8 in 80 

 l^er cent methyl Cellosolve (base). C28H47O7N. 

 Belongs probably to the macrolide group of anti- 

 biotics. Maximal light absorption at 225 m/x (log 

 £ = 4.06) and 286 m;u (log e = 2.23). Infrared 

 spectrum given in the original paper (1). Xarbo- 

 mycin yields desosamine on acid hydrolysis. 



Biological activity: Active against gram-positive 

 bacteria. Cross-resistance with picromycin. 



Toxicity: LDo (mice) 500 mg per kg subcutane- 

 ously. 



References: 



1. Corbaz, R. et al. Helv. Chim. Acta :}»: 935- 



942, 1955. 



2. Anliker, R. et al. Helv. Chim. Acta 39: 



1785-1790, 1950. 



Neocide 



Produced by: Probably an actinomycete. 

 Method of extraction: Dialysis and freeze drying. 



Cheniirul and physical properties: Stable poly- 

 peptide containing cysteine, arginine, lysine, 

 glycine, cystine, glutamic acid, aspartic acid, 

 serine, alanine, and i)roline. 



Biological activity: Antitumor and antibacterial 

 activity. Active in mice on Ehrlich ascites car- 

 cinoma and in rats on sarcoma 45. Causes reduc- 

 tion of number of mitotic figures and necrosis in 

 cancer cells. 



Toxicity: Said to be nontoxic. 



/^e/erenre; 1. Derkach, V. S. Antibiotiki 2(5): 

 40-44, 1957. 



Neoiiie thy 111 vein 



Produced by: Streptomyces sp. This strain also 

 produces methymycin (1). 



Remarks: Differs chemically from methymycin 

 only in location of one hydroxyl group (2). 



Method of extraction: Chromatography of the 

 mother liquors during the isolation of methymy- 

 cin on alumina (deactivated with 10 per cent aque- 

 ous acetic acid). Ether used as solvent and 0.5 to 

 1.0 per cent methanolic ether as developer. Methy- 

 mycin is eluted first, followed by neomethymycin. 

 Crystallized from ether-hexane (2). 



Chemical and physical properties: Macrolide; 

 m.p. 156-158°C. Isomeric with methj'mycin and 

 picromycin. [a]„ = +93° (CHCI3). Ultraviolet 

 absorption spectrum maximiuu (ethanol) at 227.5 

 niM (log e = 4.10). C.-^HwOtX: C = 63.75%; H = 

 9.04%; N = 3.07%; N^(CH,), = 5.9%; C-CH3 = 

 16.76%; — OCH;, = 0.0%. Neutral eciuivalent 

 (perchloric acid titration), 472. Acid hydrolysis 

 (HCl) yields desosamine HCl. (This is also a hy- 

 drolysis i)roduct of picromycin, erythromycin, 

 narbomycin, and methymycin.) Methylene solvate: 

 Large hexagonal plates; m.p. 154-156°C with a 

 gas given off at 135-140°C. [a\„ = +66° (ethanol). 

 Acetone solvate: Long crystals; m.p. 156-158°C. 

 Complete structure of neomethymycin (1, 2): 



HO 



N(CH,)2 



CH3 



OH CH.3 O CHs CH.i i CH3 



I I II I III 



CH;,CH— CH— CH— CH=CH— C— CH— CH,— CH— CH— CH 



I I 



o c=o 



