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. 2018 Mar 7;7(1):20.
doi: 10.3390/antibiotics7010020.

Biosynthesis of Rishirilide B

Philipp Schwarzer  1 , Julia Wunsch-Palasis  2 , Andreas Bechthold  3 , Thomas Paululat  4
Affiliations

Biosynthesis of Rishirilide B

Philipp Schwarzer et al. Antibiotics (Basel). .

Abstract

Rishirilide B was isolated from Streptomyces rishiriensis and Streptomyces bottropensis on the basis of its inhibitory activity towards alpha-2-macroglobulin. The biosynthesis of rishirilide B was investigated by feeding experiments with different 13C labelled precursors using the heterologous host Streptomyces albus J1074::cos4 containing a cosmid encoding of the gene cluster responsible for rishirilide B production. NMR spectroscopic analysis of labelled compounds demonstrate that the tricyclic backbone of rishirilide B is a polyketide synthesized from nine acetate units. One of the acetate units is decarboxylated to give a methyl group. The origin of the starter unit was determined to be isobutyrate.

Keywords: biosynthesis; polyketides; rishirilide; streptomyces.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of rishirilide B.
Figure 2
Figure 2
Labelling positions from feeding experiments using different labelled acetates and l-valine.
Figure 3
Figure 3
Proposed pathway of rishirilide B biosynthesis. (a) cyclisation and decarboxylation; (b) aromatization, oxidation; (c) Bayer-Villiger oxidation; (d) hydrolytic ring opening; (e) aldole condensation.
See this image and copyright information in PMC

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