NOBORITOMYCINS A AND B, NEW POLYETHER ANTIBIOTICS

Noboritomycins A and B, two new polycyclic ionophoric polyethers were isolated from a strain of Streptomyces noboritoensis. The crystal structure and absolute configuration of noboritomycin A were established by X-ray analysis of its silver salt C43H63O14Ag. Noboritomycin A is the first metabolic po...

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Bibliographic Details
Published in:Journal of antibiotics 1978, Vol.31(9), pp.820-828
Main Authors: KELLER-JUSLÉN, CAMILLA, KING, HAMILTON D., KUHN, MAX, LOOSLI, HANS-RUDOLF, WARTBURG, ALBERT VON
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - biosynthesis
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Chemical Phenomena
Chemistry
Ethers - biosynthesis
Ethers - isolation & purification
Ethers - pharmacology
Fermentation
Ionophores - isolation & purification
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Streptomyces - classification
Streptomyces - metabolism
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Summary:Noboritomycins A and B, two new polycyclic ionophoric polyethers were isolated from a strain of Streptomyces noboritoensis. The crystal structure and absolute configuration of noboritomycin A were established by X-ray analysis of its silver salt C43H63O14Ag. Noboritomycin A is the first metabolic polyether possessing two carboxylic acid functions on the carbon backbone (C-31), namely a free acid and an additional carboxylic acid ethylester group. An unusual spiroketal system as well as a salicylic acid chromophore represent further remarkable elements. Noboritomycin A shows in this respect a structural relationship to salinomycin and lasalocid respectively. Comparison of physico-chemical data, in particular the interpretation of the 1H- and 13C-NMR spectra, revealed that noboritomycins A and B are structurally closely related, noboritomycin B carrying an ethyl substituent on the aromatic ring in the place of a methyl group present in noboritomycin A. Both metabolites exhibit activity against Gram-positive bacteria and against Eimeria tenella (chicken coccidiosis).
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.31.820