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

Abstract

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).

A comprehensive review of glycosylated bacterial natural products

“…In sub-class I , 29 O -glycosylated polyethers were found with variant glycosyl regiospecificity (C5, C6, C15, C18, C22 and C27) including; antibiotics 6016, 1183–1186 A204-A [α-D-amicetose ( 308 )], 1187 carriomycin, 1188,1189 K-41-A, 1190,1191 K-41-B, 1192 X-14868A (maduramicin α), 1193–1196 X-14868C~D, 1193 etheromycin, 1189,1197 >UK-58852, nanhumycin, RP-37454, A80789, CP-120509 [α-D-amicetose ( 308 )], 1198 CP-91243, 1199 CP-91244, 1199 CP-96797, 1200 octacyclomycin, 1201 CP-82009, 1202 semduramicin [α-D-amicetose ( 308 )], 1203 UK-58,852-methylketal, 1204 A-13001-C 1196 and SF-2361, 1205 along with the septamycin analogs. 1206,1207 Of these, β-D-amicetose ( 48a ) was observed in CP-91243 and CP-91244.…”

Polyether ionophores: broad-spectrum and promising biologically active molecules for the control of drug-resistant bacteria and parasites

“…Several other carboxyl ionophores are also reported to have anticoccidial utility in chickens and turkeys. Although these are the most common additives used now, there are several other carboxyl ionophores reported to be more effective than additives marketed at present [49][50][51][52][53][54][55][56][57][58][59].…”

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

“…CP-82009 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 (73).…”