The isolation and structure of CP-120, 509, a new polyether antibiotic related to semduramicin and produced by mutants of Actinomadura roseorufa.

Abstract

Following the discovery of the semi-synthetic anticoccidial ionophore semduramicin1'2* (UK-61,689), a mutation program was undertaken to produce this polyether antibiotic by direct fermenta-tion3). The producing culture of the antibiotic UK-58,852, Actinomadura roseorufa ATCC53666, was chosen as the parental strain to be mutagenically treated to induce a semduramicin-producing mutant4'5). The two compounds differ from each other in that the A-ring sugar moiety of UK-58,852 is replaced by a hydroxyl group in semduramicin. Recently, we described the formation of two new polyether antibiotics, CP-91,243 and CP-91,244,

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.…”

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

“…This compound is also active against certain Gram-positive bacteria in vitro as well as the spirochete S. hyodysenteriae, the causative agent in swine dysentery (94,95). The ionophores W341C 40 and CP-120509 41 (96) were produced by Streptomyces W341 (57).…”

Structures and Properties of Naturally Occurring Polyether Antibiotics

“…Its crystal structure was reported [60]. CP-120509 exhibited in vitro activity against certain Gram-positive bacteria and the spirochete Serpulina hyodysenteriae , the causative agent of swine dysentery, but was inactive against Gram-negative bacteria.…”

“…CP-120509 exhibited in vitro activity against certain Gram-positive bacteria and the spirochete Serpulina hyodysenteriae , the causative agent of swine dysentery, but was inactive against Gram-negative bacteria. It afforded excellent anticoccidial activity against Eimeria acervulina in chickens at levels between 30 and 60 mg/kg in fed [60]. …”