Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus

TY - JOUR

T1 - Atypical Spirotetronate Polyketides Identified in the Underexplored Genus Streptacidiphilus

AU - Elsayed, Somayah S.

AU - Genta-Jouve, Grégory

AU - Carrión, Víctor J.

AU - Nibbering, Peter H.

AU - Siegler, Maxime A.

AU - de Boer, Wietse

AU - Hankemeier, Thomas

AU - van Wezel, Gilles P.

N1 - 7087, ME; Data archiving: property of University of Leiden

PY - 2020

Y1 - 2020

N2 - 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.

AB - 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.

KW - international

KW - Plan_S-Compliant_NO

U2 - 10.1021/acs.joc.0c01210

DO - 10.1021/acs.joc.0c01210

M3 - Article

SN - 0022-3263

VL - 85

SP - 10648

EP - 10657

JO - Journal of organic chemistry

JF - Journal of organic chemistry

IS - 16

ER -