RESUMO
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 (NMR and MS) methods. The absolute stereochemistry was determined by a single crystal X-ray analysis of the corresponding rubidium salt. CP-82,009 is among the 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.
Assuntos
Actinomycetales/classificação , Antibacterianos/isolamento & purificação , Coccidiostáticos/isolamento & purificação , Éteres/isolamento & purificação , Piranos/isolamento & purificação , Actinomycetales/metabolismo , Animais , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Galinhas , Coccidiostáticos/farmacologia , Éteres/farmacologia , Fermentação , Conformação Molecular , Piranos/farmacologia , Difração de Raios XRESUMO
A new polyether antibiotic CP-82,996 (C50H86O16) was isolated by solvent extraction from the fermentation broth of Actinomadura sp. (ATCC 53764). Following purification by silica gel column chromatography and crystallization, the structure of CP-82,996 was determined by a single crystal X-ray analysis. The structure is closely related to monensin, but is unique in that it contains two sugar groups, whereas monensin has none. The 1H and 13C NMR chemical shifts and assignments for CP-82,996 were elucidated, and they were compared with those determined previously for monensin. CP-82,996 is active against certain Gram-positive bacteria, and is a very potent anticoccidial agent. It effectively controlled chicken coccidiosis caused by several Eimeria species at 5-10 ppm in feed, and is 10-20 times more potent than monensin.
Assuntos
Antibacterianos/biossíntese , Bactérias/efeitos dos fármacos , Coccidiose/veterinária , Nocardiaceae/metabolismo , Doenças das Aves Domésticas/tratamento farmacológico , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antibacterianos/uso terapêutico , Galinhas , Coccidiose/tratamento farmacológico , Fermentação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Microscopia Eletrônica de Varredura , Estrutura Molecular , Monensin/análogos & derivados , Monensin/química , Monensin/isolamento & purificação , Monensin/farmacologia , Monensin/uso terapêutico , Nocardiaceae/classificação , Nocardiaceae/ultraestrutura , Difração de Raios XRESUMO
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 (NMR and 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.
Assuntos
Actinomycetales/metabolismo , Antibacterianos/biossíntese , Bactérias/efeitos dos fármacos , Coccidiostáticos/isolamento & purificação , Eimeria/efeitos dos fármacos , Actinomycetales/classificação , Animais , Antibacterianos/análise , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Galinhas , Coccidiose/tratamento farmacológico , Coccidiostáticos/análise , Coccidiostáticos/farmacologia , Cristalografia , Fermentação , Furanos/análise , Furanos/isolamento & purificação , Furanos/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Piranos/farmacologiaRESUMO
A new monocarboxylic acid ionophore antibiotic related to zincophorin, CP-78,545 (1), was found in the culture broth of Streptomyces sp. N731-45. CP-78,545 was extracted with organic solvents and purified by column chromatography. The metabolite, which is active in vitro against certain Gram-positive bacteria, as well as the anaerobe Treponema hyodysenteriae, and a coccidium Eimeria tenella, was isolated as a water insoluble magnesium salt (2) in 2:1 (ligand/metal) stoichiometry. The structure of CP-78,545 was elucidated by spectroscopic (NMR and MS) methods, and the relative stereochemistry was determined by single-crystal X-ray analysis of the cadmium salt (3). CP-78,545, i.e., 24-dehydrozincophorin, is unique since its molecular backbone contains a terminal double bond previously not found in other polyether ionophores.