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Molecules 2017, 22(10), 1758; doi:10.3390/molecules22101758

Novel Bioactive Paulomycin Derivatives Produced by Streptomyces albus J1074

Departamento de Biología Funcional e Instituto Universitario de Oncología del Principado de Asturias (I.U.O.P.A), Universidad de Oviedo, C/Julian Claveria s/n, 33006, Oviedo (Asturias), Spain
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Received: 25 September 2017 / Revised: 11 October 2017 / Accepted: 17 October 2017 / Published: 18 October 2017
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Abstract

Four novel paulomycin derivatives have been isolated from S. albus J1074 grown in MFE culture medium. These compounds are structural analogs of antibiotics 273a and 273a containing a thiazole moiety, probably originated through an intramolecular Michael addition. The novel, thiazole, moiety-containing paulomycins show a lower antibiotic activity than paulomycins A and B against Gram-positive bacteria. However, two of them show an improved activity against Gram-negative bacteria. In addition, the four novel compounds are more stable in culture than paulomycins A and B. Thus, the presence of an N-acetyl-l-cysteine moiety linked to the carbon atom of the paulic acid isothiocyanate moiety, via a thioester bond, and the subsequent intramolecular cyclization of the paulic acid to generate a thiazole heterocycle confer to paulomycins a higher structural stability that otherwise will conduce to paulomycin degradation and into inactive paulomenols. View Full-Text
Keywords: antibiotic 273a2; paulic acid; paulomenol; structural analogue; thiazole moiety antibiotic 273a2; paulic acid; paulomenol; structural analogue; thiazole moiety
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Hoz, J.-D.; Méndez, C.; Salas, J.A.; Olano, C. Novel Bioactive Paulomycin Derivatives Produced by Streptomyces albus J1074. Molecules 2017, 22, 1758.

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