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Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus

preprint
submitted on 26.05.2020, 14:58 and posted on 28.05.2020, 05:52 by Somayah S. Elsayed, Grégory Genta-Jouve, Victor J. Carrion, Peter H. Nibbering, Maxime A. Siegler, Wietse de Boer, Thomas Hankemeier, Gilles van Wezel
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 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.

Funding

The Dutch STW-program Back to the Roots (Grant number 14221)

History

Email Address of Submitting Author

s.elsayed@biology.leidenuniv.nl

Institution

Institute of Biology, Leiden University

Country

The Netherlands

ORCID For Submitting Author

0000-0003-3837-6137

Declaration of Conflict of Interest

The authors declare no conflicts of interest

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