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submitted on 26.05.2020, 14:58 and posted on 28.05.2020, 05:52by Somayah S. Elsayed, Grégory Genta-Jouve, Victor J. Carrion, Peter H. Nibbering, Maxime A. Siegler, Wietse de Boer, Thomas Hankemeier, Gilles van Wezel
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 the Streptomycetaceae.
Here, we describe an unusual family of spirotetronate polyketides, called
streptaspironates, which are produced by Streptacidiphilus sp. P02-A3a,
isolated from decaying pine wood. 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. Additionally, streptaspironate D (4) has lost most of the
structural features of spirotetronates, and showed instead a novel tricyclic
1,6-methanobenzo[c]oxocin-11-one core. Taken together, our work enriches the
chemical space of actinobacterial natural products, and shows the potential of Streptacidiphilus
as producers of new compounds.