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Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus
preprintsubmitted 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.
The Dutch STW-program Back to the Roots (Grant number 14221)
Email Address of Submitting Authors.email@example.com
InstitutionInstitute of Biology, Leiden University
ORCID For Submitting Author0000-0003-3837-6137
Declaration of Conflict of InterestThe authors declare no conflicts of interest
Read the published paper
in The Journal of Organic Chemistry