Details

Autor(en) / Beteiligte

• Mohamed, Osama G
• Khalil, Zeinab G
• Salim, Angela A
• Cui, Hui
• Blumenthal, Antje
• Capon, Robert J

Titel

Lincolnenins A–D: Isomeric Bactericidal Bianthracenes from Streptomyces lincolnensis

Ist Teil von

• Journal of organic chemistry, 2021-08, Vol.86 (16), p.11011-11018

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2021

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Cultivation profiling followed by chemical analysis of Streptomyces lincolnensis yielded four new isomeric bianthracenes, lincolnenins A–D (1–4), with relative stereostructures assigned on the basis of detailed spectroscopic analysis. Lincolnenins A (1) and B (2) exhibit restricted rotation about alternate bianthracene 9–9′ and 9–8′ bridges, respectively, and exist as single atropisomers, whereas C (3) and D (4) are thermally interconvertible atropisomers sharing a common 8–8′ bianthracene bridge. Absolute configurations were assigned to 1–4 on the basis of diagnostic ROESY correlations and ECD calculations, whereas acid-mediated dehydration of 1 led to formation and revision of the absolute configuration of the biosynthetically related known Streptomyces antibiotic, setomimycin (5). Lincolnenin A (1) exhibited significant bactericidal activity against multiple susceptible and drug-resistant Gram-positive pathogens (MIC99 < 2.0 μM), including Mycobacterium tuberculosis H37Ra (MIC99 = 0.9 μM).