Echinosporamicin, a New Antibiotic Produced by Micromonospora echinospora ssp. echinospora, LL‐P175.

TLN-05220, TLN-05223, new Echinosporamicin-type antibiotics, and proposed revision of the structure of bravomicins

“…The potency of the polycyclic aromatics was stronger than that of vancomycin against all tested pathogens except Streptococcus pneumoniae PenR (LSPQ 3349). Although the specific strains were different, the activity of TLN-05220 seems to be similar to that reported for echinosporamicin 12,13 and bravomicin A. 14 Compound 1 was also evaluated for antitumor activity.…”

“…The presence of five carbonyl carbons (d 187.1 (Â2), 183.3, 181.9 and 159.0), two sets of ortho-coupled aromatic protons (d 8.63 and 8.39; 7.47 and 7.44) and a singlet aromatic proton signal (d 6.73) strongly suggested the presence of a polycyclic aromatic with a core backbone composed of six fused rings, similar to the albofungins, 10 simaomicins 11 and echinosporamicin 3. 12, 13 The presence of a carbonyl carbon at d 187.1 (C-5) resembles the situation with echinosporamicin 3, suggesting the presence of p-benzoquinone ring (ring E) instead of a g-pyrone, as reported in the albofungin and simaomicin antibiotics, in which it could be derived through the oxidative cleavage of an echinosporamicin-like ring E. Furthermore, the proton and carbon NMR data of TLN-05220 (1) were very similar to that of echinosporamicin 3, isolated from M. echinospora ssp. echinospora LL-P175.…”

Secondary Metabolites from Marine Micromonospora: Chemistry and Bioactivities

“…Echinosporamicin exhibited antibacterial activity against methicillin‐resistant Staphylococci and vancomycin‐resistant Enterococci strains. In an in vivo test, echinosporamicin showed efficacy against S. aureus infection in a mouse model with ED 50 of 0.35 mg/kg …”