■326 



DESCRIPTlOXy OF ANTIBIOTICS 



References: 



1. Hazen, E. L. and Brown, R. Proc. Soc. 



Exptl. Biol. Med. 76: 93-97, 1951. 



2. Dutcher, J. D. el al. Antibiotics Ann. 



191-194, 1953-1954. 



3. Sternberg, T. H. et al. Antibiotics Ann. 



199-209, 1953-1954. 



4. Campbell, C. C. et al. Antil)iotics Ann. 



210-214, 1953-1954. 



5. British Patent 714,189, August 25, 1954. 



6. Newcomer, V. D. et al. Antibiotics Ann. 



686-690, 1954-1955. 



7. Campbell, C. C. et al. Antibiotics Ann. 



858-862, 1954-1955. 



8. West, M. K. et al. Antibiotics Ann. 231- 



235, 1955-1956. 



9. Seneca, H. Antil)iotics Ann. 697-703, 



1955-1956. 



10. Seneca, H. and Bergendahl, E. Antibiotics 



& Chemotherapy 5: 737-741, 1955. 



11. Brown, R. and Hazen, E. L. 7n Therapy of 



fungus diseases. Sternberg, T. H. and 

 Newcomer, V. D., eds. Little, Brown 

 and Co., Boston, 1955, pp. 164-167. 



12. Dutcher, J. D. et al. In Therapy of fungus 



diseases. Sternberg, T. H. and Newcomer 

 V. D., eds. Little, Brown and Co., Bos- 

 ton, 1955, pp. 168-175. 



13. Hazen, E. L. et al. In Therapy of fungus 



diseases. Sternberg, T. H. and New- 

 comer, V. D., eds. Little, Brown and 

 Co., Boston, 1955, pp. 199-204. 



14. Flarer, F. In Therapy of fungus diseases. 



Sternberg, T. H. and Newcomer, V. D., 

 eds. Little, Brown and Co., Boston, 

 1955, pp. 219. 



15. Stout, H. A. and Pagano, J. F. Antibiotics 



Ann. 704-710, 1955-1956. 



16. Newcomer, V. D. et al. Antibiotics Ann. 



831-836, 1955-1956. 



17. Zaumeyer, W. J. and Wester, R. E. Phyto- 



pathology 46: 470, 1956. 



18. Stewart, 0. T. Brit. Med. J. 1: 658-660, 



1956. 



19. DiMarco, C. R. and Davis, B. H. Plant 



Disease Reptr. 41: 284-288, 1957. 



20. Szkolnik, M. and Hamilton, J. M. Plant 



Disease Reptr. 41: 289-292, 1957. 



21. Ark, P. A. and Thompson, J. B. Plant 



Disease Reptr. 41: 452-454, 1957. 



22. Ark, P. A. and Thompson, J. B. Plant 



Disease Reptr. 41: 460-464, 1957. 



23. Natti, J. Plant Disease Reptr. 41: 780- 



788, 1957. 



24. Yacowitz, H. et al. Poultry Sci. 36: 1171, 



1957. 



25. Dutcher, J. \}. Monographs on Therapy 



2: 87-98, 1957. 



26. Brown, R. and Hazen, E. L. Trans. N. Y. 



Acad. Sci. 19: 447-456, 1957. 



27. Walters, D. R. et al. J. Am. Chem. Soc. 



79: 5076-5077, 1957. 



28. Baum, (1. L. et al. Antibiotics & Chemo- 



therapy 7: 477-482, 1957. 



29. Vandeputte, J. and Gold, W. U. S. Patent 



2,786,781, March 26, 1957. 



30. Hazen, E. L. and Brown, R. F. U. S, Patent 



2,797,183, June 25, 1957. 



31. Gould, C.J. Golf Course Reptr. 25:18-20, 



1957. 



32. Osswald, H. and Seeliger, H. P. R. Arz- 



neimittel-Forsch. 8: 370-374, 1958. 



33. Miller, W. H. Am. J. Botany 43: 183-190, 



1958. 



34. Vandeputte, J. U. S. Patent 2,832,719, April 



29, 1958. 



35. Stessel, G. J. Plant Disease Reptr. 42: 



396-398, 1958. 



36. Vald.skovd,, E. Ceskoslov. Mikroliiol. 3: 



323-325, 1958. 



37. Rao, K. V. and Cullen, W. P. Abstr. 134th 



Meeting Am. Chem. Soc. 22-0-23-0, 1958. 



38. Frank, E. et al. Antibiotics Ann. 898-902, 



1958-1959. 



39. Yacowitz, H. et al. Antil)iotics Ann. 994- 



997, 1958-1959. 



40. Tsay, J. S. e/a/. Antil)iotiki 4(2) : 3-5, 1959. 



Oleandomycin 



Produced by: Streptuinyces antibiutirus (4). This 

 organism produces a minor component in the cul- 

 ture-broths, identified as oleandomycin chloro- 

 hydrin: colorless, felt-like crystals; m. p. 150-153°C 

 (decomposition) (hydrochloride) (16, 18). 



Synonyms: Antibiotic PA 105, matromycin, 

 romicil, amimycin, antibiotic RO 2-7638. 



Method of extraction: I. Mycelium extracted 

 with methyl isobutyl ketone. Extract concentrated 

 in vacuo. Concentrate extracted into water (pH 

 2.0). Aciueous phase washed with benzene to re- 

 move the methyl isobutyl ketone, then extracted 

 with ether at pH 6.5. Removal of ether by distil- 

 lation gives crystals. Recrystallized from hot 

 ethyl acetate (4). Base crystallized from aqueous 

 methanol or acetone (18). II. Paltered broth 

 extracted with methyl isobutyl ketone. Back- 

 extraction with dilute atiueous acid. Extraction 

 with methyl ethyl ketone at pH 9.0 Hydrated 

 oleandomycin hydrochloride precipitated upon the 

 addition of Hci (1). 



Chemical and physical properties: Maerolide (12). 

 Basic substance. Base: Colorless prisms, m.p. 



