292 



]:)E8CR1PTI0N.S OF ANTIBIOTICS 



but no 6-gluco8amine (6-desoxy-<)-amino-D-glu- 

 cose) as with kanamycin A. N-acetyl kananij/rin B: 

 Decomposes gradually at 220-250°C. [«)" = +150° 

 (c = 0.42 per cent in water, 1). 



Biological activity: Active on gram -positive and 

 gram-negative liacteria, including mycobacteria. 

 Almost 2 to 3 times as active as kanamycin A 

 against bacteria such as Aerobacter aerogenes, B. 

 cereus, B. subtilis, Br. bronchisepiica, E. coli, K. 

 pneumoniae, Staph, aureus, and Proteus spp. Not 

 active on Clostridia or ('. albicans, Salmonella, 

 or Serratia marcescens. Neither kanamycin A nor 

 B is very active on streptococci. B is less active 

 than A on mycobacteria (2). 



Toxicity: More toxic to animals than kanamy- 

 cin A (3). 



References: 



1. Schmitz, H. et al. J. Am. Chem. See. »(»: 



2911-2912, 1958. 



2. Gourevitch, A. et al. Antil)iotics & Chemo- 



therapy 8: 149-159, 1958. 



3. Hubef, K. Quoted in Finegold, S. N. et al. 



Antibiotics Ann. 606-622, 1958-1959. 



Lagosin 



Produced by: Streptnmyces sp. (1). 



Synonym: Antibiotic A 246. 



Method of extraction: Mycelium (60 per cent of 

 the activity) extracted with 80 per cent aqueous 

 acetone. Extract concentrated iu vacuo. A small 

 amount of n-butanol added to the aqueous residue 

 and the water removed by concentration in vacuo. 

 Precipitated from residual solution by addition of 

 diethyl ether in excess. Filtrate (40 per cent of the 

 activity) extracted with n-butanol. Extracts con- 

 centrated, then treated as above (1). 



Chemical and physical properties: Macrocyclic 

 lactone, with pentaene chromophore. Crystalline 

 substance; m.p. about 235°C (decomposition). 

 [afn = -160° (c = 0.2 per cent in methanol). 

 Ultraviolet absorption spectnun maxima at 325, 

 340, and 358 m^ (J^lcm 1491). C41H66-70O14 . Perhy- 

 dro derivative: C^iHts-soOh ; m.p. 156-157°C. 

 [a]^" = +3.5° (c = 1.98 per cent in methanol) 

 (1-3). Structural formula given in Chapter 6 and 

 reference 4. 



Biological activity: Active on yeasts and fila- 

 mentous fungi (1). 



References: 



1. Ball, S. et al. J. Gen. Microbiol. 17: 96- 



103, 1957. 



2. Dhar, M. L. ct al. Proc. Chem. Soc. 148- 



149, 1958. 



3. Dhar, M. L. et al. Proc. Chem. Soc. 154- 



155, 1958. 



4. Dhar, M. L. cl al. Proc. Chem. Soc. 310- 

 311, 1960. 



Laveiiduliii 



Produced by: Strcptomyces lavendulae (1). 



Synonym: Streptothricin-like antibiotic. 



Method of extraction: Like that for actinorubin. 



Chemical and physical properties: Basic sub- 

 stance. HCl salt: White powder. Helianlhate: 

 Orange needles in clusters; m.p. 212-220°C (de- 

 composition). Soluble in 80 per cent aqueous 

 methanol; insoluble in 20 per cent methanol. C = 

 51.16%; H = 5.99%; N = 17.32%; S = 9.17%. 

 Probable empirical formula: C49H63O18N13S3 (1). 

 Major component in l)roth indistinguishable from 

 streptothricin on paper chromatography (wet 

 butanol-jo-toluenesulfonic acid) (4j. 



Biological activity: Active on gram-positive and 

 gram-negative bacteria, including mycobacteria. 

 Slightly active on Trichophyton interdigitale (16 

 Mg per mlj. Cross-resistance with actinorul)in 

 and streptothricin (3). 



Toxicity: LDiuo (mice) 28.5 mg per kg intra- 

 peritoneally. Toxic effects at therapeutic levels 

 (2). 



References: 



1. Junowicz-Kocholaty, R. and Kocholaty, W. 



J. Biol. Chem. 168: 757-764, 1947. 



2. Morton, H. E. Proc. Soc. Exptl. Biol. Med. 



64: 327-331, 1947. 



3. Kelner, A. and Morton, H. E. J. Bacteriol. 



.i3: 695-704, 1947. 



4. Benedict, R. G. Botan. Rev. 19: 229-320, 



1953. 



Lenaiiiyciii 



Produced by: Strcptomyces sp. 



Method of extraction: Broth adjusted to pH 4.0, 

 filtered, then extracted with n-l)utyl acetate. The 

 aqueous phase concentrated //; vacuo and the 

 gummy Inown sul)stance which precipitates on 

 addition of absolute ethanol is discarded. Ac|ue- 

 ous ethanolic filtrate treated with alumina, then 

 concentrated in vacuo with addition of absolute 

 methanol. Addition of acetone gives an inactive 

 white precipitate. Concentrate of the mother 

 liquor gives a crude precipitate of lenamycin on 

 standing in desiccator. Recrj'stallization from 

 methanol. 



Chemical and physical properties: Organic acid 

 amide. Needles; m.p. 202-207°C (decomposition) 

 (d.p. 290-300°). Optically inactive. C = 40.89%; 

 H = 4.42%; N = 22.91%. No S, halogen, or met- 

 als. C4H4N2O2-.3 . Ultraviolet absorption spectrum 

 maximum at 216 niyu {E\7m 817). Infrared absorp- 



