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Lincolnenins A–D: Isomeric Bactericidal Bianthracenes from Streptomyces lincolnensis
- Source :
- The Journal of Organic Chemistry; August 2021, Vol. 86 Issue: 16 p11011-11018, 8p
- Publication Year :
- 2021
-
Abstract
- Cultivation profiling followed by chemical analysis of Streptomyces lincolnensisyielded 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 1–4on the basis of diagnostic ROESY correlations and ECD calculations, whereas acid-mediated dehydration of 1led to formation and revision of the absolute configuration of the biosynthetically related known Streptomycesantibiotic, setomimycin (5). Lincolnenin A (1) exhibited significant bactericidal activity against multiple susceptible and drug-resistant Gram-positive pathogens (MIC99< 2.0 μM), including Mycobacterium tuberculosisH37Ra (MIC99= 0.9 μM).
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 86
- Issue :
- 16
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs54880930
- Full Text :
- https://doi.org/10.1021/acs.joc.0c02492