E-73, AN ANTITUMOR SUBSTANCE 1127 e n t on qualitative color tests and on Rf. The periodate oxidation information given is difficult to interpret in terms of a unique structure. Quantitative data on the amounts of formaldehyde liberated during periodate oxidation before and after reduction with borohydride would be useful in determining whether the compound tested and found t o be inactive in hemagglutination inhibition tests in the blood group B system was galactose linked a t o the 6 carbon of N-acetylglucosaniine : inhibition of precipitation, which is a more sensitive test, was not carried out. The fucose in blood group B substance from ovarian cyst appears to be linked very differently from the fucose in blood group A and O(H) substances from hog gastric mucin. Only 45 mg. of free fucose (2.6yQ) of 1.7 g. dialysable constituents were found when ovarian cyst B substance was hydrolyzed a t fiH 1.G for 2 hr. a t looo, whereas -17 to 9570 of the fucose in the dialysate was free when hog gastric mucin was treated similarly.'O h blood group A substance derived from human ovarian cyst fluid and partially hydrolyzed a t pH 1.9 also liberated most of the dialysable fucose as free fucose."5 These observations would suggest that part of the fucose in blood group h substance is linked quite differently from that in blood group B substance. 'rhus if the hypothesis of Watkins and were correct that A and B substances are derived from H substance under the influence of the X and B genes, respectively, these genes would also have to modify the fucose portion of the H substance in addition to introducing the specific A and B oligosaccharides side chains to account for the differences in lability of the fucose. Moreover, the findings that the Pl fractions' liberated by mild acid hydrolysis of B and A substance give rise to antibodies which were different in specificity from each other and from the original A and B substances also indicate that the genes determining A or B specificity control other steps in the synthesis of their respective substances in addition to the synthesis of the specific oligosaccharide side chains which are recognized using anti-A and anti-B serum.(35) Unpublished observations. (36) W. M. Watkins and W. T. J. Xorgan, Vox Sanguinis, 4, 97 (1959). SEWThe isolation of E-'73 with antitumor properties together with two diastereoisomeric forms of cycloheximide, fungicidin and two inert crystalline compounds from the culture filtrates of Streptomyces albulus is described.In our cancer-screening program, a new species of actinomycete was isolated from the soil by our microbiology division. Broths from this culture, when tested a t the Sloan-Kettering Institute as well as a t our laboratories showed significant activity against mouse Sarcoma 180 and against human tumor transplants grown in rats. This organism was designated as Streptomyces alhulus,2 and the isolation of the active principle is reported here.The organism is grown in the usual natural media in submerged culture for 3-6 days. The broths are active...
A new polyether antibiotic CP-84,657 (C45H78O14) was isolated by solvent extraction from the fermentation broth of Actinomadura sp. (ATCC 53708). Following purification by column chromatography and crystallization, the structure of CP-84,657 was elucidated by spectroscopic (NMRand MS) methods. The absolute stereochemistry was determined by a single crystal X-ray analysis of the corresponding rubidium salt. CP-84,657 is among the most potent anticoccidal agents known, effectively controlling the Eimeria species that are the major causative agents of chicken coccidiosis at doses of 5 mg/kg or less in feed. It is also active in vitro against certain Gram-positive bacteria, as well as the spirochete, Treponema hyodysenteriae.Interest in polyether antibiotics has remained at a high level for over 20 years, owing largely to the commercial importance of this class of drugs in veterinary medicine. For example, monensin1*, lasalocid1* and salinomycin2) are marketed as anticoccidial agents for poultry, and are used as growth permittants in cattle or swine. Narasin1* and maduramicin3) are also used as anticoccidial agents.In the process of screening actinomycetes for novel antimicrobial substances, a new strain of Actinomadura sp. was found to produce a new polyether antibiotic, CP-84,657 (1). This compound, which was very potent versus Eimeria coccidia in chickens, was shown to be structurally similar to portmicin4), Upon completion of this work5), studies were presented by Hamill et al.6) on the discovery of a new polyether antibiotic, A82810, produced by Actinomadura fibrosa. Although an X-ray analysis of A82810 has not been reported, based on 13C and *H NMRdata it appears that CP-84,657 and A82810 are identical.The present paper describes the taxonomy and fermentation studies on the producing organism of CP-84,657, as well as the isolation, characterization and biological testing of this antibiotic.
A new polyether antibiotic CP-82,009 (C49H84O17) was isolated by solvent extraction from the fermentation broth of Actinomadura sp. (ATCC 53676). Following purification by column chromatography and crystallization, the structure of CP-82,009 was elucidated by spectroscopic (NMRand MS) methods. The absolute stereochemistry was determined by a single crystal X-ray analysis of the corresponding rubidium salt. CP-82,009 is amongthe most potent anticoccidial agents known, effectively controlling the Eimeria species that are the major causative agents of chicken coccidiosis at doses of 5 mg/kg or less in feed. It is also active in vitro against certain Gram-positive bacteria, as well as the spirochete, Serpulina (Treponema) hyodysenteriae.Polyether antibiotics have been an important class of drugs in veterinary medicine for over 20 years. For example, monensin1*, lasalocid1} and salinomycin2) are marketed as anticoccidal agents for poultry, and are used as growth permittants in cattle and swine. Narasin1} and maduramicin3) are also used as anticoccidial agents. In the course of screening actinomycetes for novel antimicrobial substances, a new strain of Actinomadura sp. was found to produce a new polyether antibiotic, CP-82,009 (1). This compound, which was very potent against Eimeria coccidia in chickens, was shown to be structurally similar to septamycin4).The present paper describes the taxonomy and fermentation studies on the producing organism of CP-82,009, as well as the isolation, characterization and biological testing of this antibiotic5).
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