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. 2018 Oct 30:6:528.
doi: 10.3389/fchem.2018.00528. eCollection 2018.

Marine Bacterial Aromatic Polyketides From Host-Dependent Heterologous Expression and Fungal Mode of Cyclization

Chunshuai Huang  1   2 , Chunfang Yang  1 , Yiguang Zhu  1 , Wenjun Zhang  1 , Chengshan Yuan  1 , Changsheng Zhang  1   2
Affiliations

Marine Bacterial Aromatic Polyketides From Host-Dependent Heterologous Expression and Fungal Mode of Cyclization

Chunshuai Huang et al. Front Chem. .

Abstract

The structure diversity of type II polyketide synthases-derived bacterial aromatic polyketides is often enhanced by enzyme controlled or spontaneous cyclizations. Here we report the discovery of bacterial aromatic polyketides generated from 5 different cyclization modes and pathway crosstalk between the host and the heterologous fluostatin biosynthetic gene cluster derived from a marine bacterium. The discovery of new compound SEK43F (2) represents an unusual carbon skeleton resulting from a pathway crosstalk, in which a pyrrole-like moiety derived from the host Streptomyces albus J1074 is fused to an aromatic polyketide SEK43 generated from the heterologous fluostatin type II PKSs. The occurrence of a new congener, fluoquinone (3), highlights a bacterial aromatic polyketide that is exceptionally derived from a characteristic fungal F-mode first-ring cyclization. This study expands our knowledge on the power of bacterial type II PKSs in diversifying aromatic polyketides.

Keywords: aromatic polyketides; cyclization modes; heterologous expression; pathway crosstalk; type II polyketide synthase.

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Figures

Figure 1
Figure 1
Chemical structures of compounds 1–6.
Figure 2
Figure 2
Selected key COSY and HMBC correlations of SEK43F (2) and fluoquinone (3). Key HMBC correlations connecting units A and B of 2 are in red.
Figure 3
Figure 3
Proposed biosynthesis scheme leading to diversified APKs by taking 5 different cyclization strategies (A–E) and a pathway crosstalk between the host S. albus and the heterologous fls gene cluster (A,B).
See this image and copyright information in PMC

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