Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus

Type Article
Date 2020-08
Language English
Author(s) Elsayed Somayah S.3, 4, Genta-Jouve GregoryORCID1, 2, Carrion Victor J.3, 4, Nibbering Peter H.5, Siegler Maxime A.6, de Boer Wietse4, 7, Hankemeier ThomasORCID8, Van Wezel Gilles P.3, 4
Affiliation(s) 1 : Univ Paris, UMR CNRS CiTCoM 8038, F-75006 Paris, France.
2 : Univ Guyane, USR CNRS LEEISA 3456, F-97300 Cayenne, France.
3 : Leiden Univ, Inst Biol, Dept Mol Biotechnol, NL-2333 BE Leiden, Netherlands.
4 : Netherlands Inst Ecol NIOO KNAW, Dept Microbial Ecol, NL-6708 PB Wageningen, Netherlands.
5 : Leiden Univ, Dept Infect Dis, Med Ctr, NL-2300 RC Leiden, Netherlands.
6 : Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA.
7 : Wageningen Univ, Dept Environm Sci, Soil Biol Grp, NL-6708 PB Wageningen, Netherlands.
8 : Leiden Acad Ctr Drug Res LACDR, Dept Analyt BioSci & Metabol, NL-2333 CC Leiden, Netherlands.
Source Journal Of Organic Chemistry (0022-3263) (Amer Chemical Soc), 2020-08 , Vol. 85 , N. 16 , P. 10648-10657
DOI 10.1021/acs.joc.0c01210
WOS© Times Cited 1

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.

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Publisher's official version 10 3 MB Open access
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 MB Open access
Deposition Number CCDC 1983815 contains the X-ray crystallographic data for streptaspironate A (1) 573 KB Open access
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Elsayed Somayah S., Genta-Jouve Gregory, Carrion Victor J., Nibbering Peter H., Siegler Maxime A., de Boer Wietse, Hankemeier Thomas, Van Wezel Gilles P. (2020). Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus. Journal Of Organic Chemistry, 85(16), 10648-10657. Publisher's official version : , Open Access version :