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Pederin-Type Pathways of Uncultivated Bacterial Symbionts: Analysis of O-Methyltransferases and Generation of a Biosynthetic Hybrid
Ist Teil von
Journal of the American Chemical Society, 2009-03, Vol.131 (8), p.2780-2781
Ort / Verlag
United States: American Chemical Society
Erscheinungsjahr
2009
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
The complex polyketide pederin is a potent antitumor agent isolated from Paederus spp. rove beetles. We have previously isolated a set of genes from a bacterial endosymbiont that are good candidates for pederin biosynthesis. To biochemically study this pathway, we expressed three methyltransferases from the putative pederin pathway and used the partially unmethylated analogue mycalamide A from the marine sponge Mycale hentscheli as test substrate. Analysis by high-resolution MS/MS and NMR revealed that PedO regiospecifically methylates the marine compound to generate the nonnatural hybrid compound 18-O-methylmycalamide A with increased cytotoxicity. To our knowledge, this is the first biochemical evidence that invertebrates can obtain defensive complex polyketides from bacterial symbionts.