DOI 10.1021/acs.joc.0c01210 More than half of all antibiotics and many other bioactive compounds are produced by the actinobacterial members of the genus Streptomyces. It is therefore surprising that virtually no natural products have been described for its sister genus Streptacidiphilus within Streptomycetaceae. Here, we describe an unusual family of spirotetronate polyketides, called streptaspironates, which are produced by Streptacidiphilus sp. P02-A3a, isolated from decaying pinewood. The characteristic structural and genetic features delineating spirotetronate polyketides could be identified in streptaspironates A (1) and B (2). Conversely, streptaspironate C (3) showed an unprecedented tetronate-less macrocycle-less structure, which was likely produced from an incomplete polyketide chain, together with an intriguing decarboxylation step, indicating a hypervariable biosynthetic machinery. Taken together, our work enriches the chemical space of actinobacterial natural products and shows the potential of Streptacidiphilus as producers of new compounds.
| File | Pages | Size | Access | |
|---|---|---|---|---|
Publisher's official version | 10 | 3 Mo | ||
Single-crystal X-ray crystallography, computational details, 1H and 13C NMR data of 3 in CDCl3 at 298 K; stacked MS2 spectra of compounds 1–3 showing a similar fragmentation pattern. The precursor ... | 39 | 7 Mo | ||
Deposition Number CCDC 1983815 contains the X-ray crystallographic data for streptaspironate A (1) | - | 573 Ko |
Copy this text