Struktur und Biosynthese von Collinolacton aus Streptomyces sp. und Beiträge zum Screening neuer Wirkstoffe

TL;DRAbstract

The cyclodecatrien collinolactone is a new microbial natural product from Streptomyces sp. Gö 40/10 and represents a hitherto unknown chemical class of substances. The structure elucidation was performed with modern spectroscopic methods (1D/2D-NMR, HR-ESI-MS, IR, UV) and revealed the unique combination of a 7-10-6-cyclodecatrien structure with a hydroxyl group, an ethyl side chain, and two lactones. Collinolactone exists as a mixture of two rotamers of a double bond in the ratio of 4:1. By feeding [13C]-labelled precursors to the producing strain, fermentation under 18O2 rich atmosphere and NMR-spectroscopic analysis of the natural product the polyketide biosynthetic origin of all carbon and oxygen atoms in the collinolactone skeleton was proven. These studies suggests a biosynthetic pathway starting from the formation of a nonaketide via PKS and macrolactonization, followed by a so far unkown rearrangement of the double bonds under formation of the tricyclic skeleton, and finally int

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