CP-82,009, a potent polyether anticoccidial related to septamycin and produced by Actinomadura sp.

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.

CP-82,996, a novel diglycoside polyether antibiotic related to monensin and produced by Actinomadura sp.

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.

CP-60,993, a new dianemycin-like ionophore produced by Streptomyces hygroscopicus ATCC 39305: fermentation, isolation and characterization.

CP-60,993, 19-epi-dianemycin, is a novel polycyclic ether antibiotic produced by Streptomyces hygroscopicus ATCC 39305. Fermentation recovery, purification and crystallization were achieved using standard procedures. CP-60,993 was characterized as a monocarboxylic acid. Elemental analysis suggested a molecular formula of C47H78O14 for the free acid and C47H77O14 Na for the sodium salt. Crystalline from CP-60,993 sodium salt shows the following properties: m.p. 193-205 degrees C, E1%(1 cm) = 157 at 232 nm, [alpha]25 degrees C(D) + 11.0 (c 1, methanol). The structure, determined by MS, PMR and CMR, differs from dianemycin only in the stereochemistry at position 19. This was confirmed by X-ray crystallography carried out on the rubidium salt of CP-60,993. It exhibited activity in vitro against Gram-positive and anaerobic bacteria, efficacy against Eimeria coccidia in vivo in poultry, and stimulation in vitro of rumen propionic acid production.

CP-84,657, a potent polyether anticoccidial related to portmicin and produced by Actinomadura sp.

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.

UK-69,753, a novel member of the efrotomycin family of antibiotics. I. Taxonomy of the producing organism, fermentation and isolation.

UK-69,753 is a novel antibiotic structurally related to efrotomycin and factumycin, produced by a new strain of Amycolatopsis orientalis (ATCC 53550). The antibiotic potency in the fermentation broth was monitored by HPLC with diode array detection. A six tube counter current distribution was used to purify UK-69,753.

CP-78,545, a new monocarboxylic acid ionophore antibiotic related to zincophorin and produced by a Streptomyces.

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.

UK-63,052 complex, new quinomycin antibiotics from Streptomyces braegensis subsp. japonicus; taxonomy, fermentation, isolation, characterisation and antimicrobial activity.

UK-63,052 complex, a new group of quinomycin-like antibiotics comprising UK-63,052 (factor A), UK-63,598 (factor C), UK-65,662 (factor B) and several uncharacterised minor components, is produced by a new subspecies of the genus Streptomyces for which the name Streptomyces braegensis Dietz subsp. japonicus, is proposed. The strain, N617-29, is characterised by a negative melanin reaction, grey aerial mycelium, spiral spore chains and smooth or slightly warty spores. Structure determination has identified UK-63,052, C56H68N10O14S2, UK-63,598, C53H62N10O14S2 and UK-65,662, C55H66N10O14S2 as quinaldic acid substituted quinomycins with unusual bridgehead sulfur substitution as shown in Fig. 3.

Endusamycin, a novel polycyclic ether antibiotic produced by a strain of Streptomyces endus subsp. aureus.

Endusamycin formerly called CP-63,517 (C47H77O14Na), is a novel polycyclic ether antibiotic produced by a new strain of Streptomyces endus subsp. aureus (ATCC 39574). Recovery, fractionation and purification were achieved using standard procedures. Forms include the endusamycin free acid, mp 95 approximately 105 degrees C, lambda max 232 nm (log E 4.16), [alpha]25D +47.4 degrees (c 0.5, methanol) and a crystalline sodium salt, mp 215 approximately 220 degrees C, lambda max 232 nm, (log E 4.15), [alpha]25D +25 degrees (c 0.5, methanol). The structure is shown below, Fig. 1. Endusamycin exhibited; antibacterial activity, in vitro against Gram-positive and anaerobic bacteria, effectiveness against coccidia in poultry, and stimulation of propionic acid production in an in vitro system.

CP-54,883 a novel chlorine-containing polyether antibiotic produced by a new species of Actinomadura: taxonomy of the producing culture, fermentation, physico-chemical and biological properties of the antibiotic.

The novel chlorine-containing acidic polycyclic ether antibiotic CP-54,883 (C41H62O12Cl2) [corrected] is produced by the fermentation of Actinomadura routienii Huang sp. nov. This report presents the taxonomy and the fermentation conditions for the antibiotic-producing culture. The antibiotic is mainly active against Gram-positive bacteria. It protects chickens against Eimeria challenge in vivo and enhances rumen propionic acid in vitro. The physico-chemical properties are also characterized.