Issue 1, 2019

Dalmanol biosyntheses require coupling of two separate polyketide gene clusters

Abstract

Polyketide–polyketide hybrids are unique natural products with promising bioactivity, but the hybridization processes remain poorly understood. Herein, we present that the biosynthetic pathways of two immunosuppressants, dalmanol A and acetodalmanol A, result from an unspecific monooxygenase triggered hybridization of two distinct polyketide (naphthalene and chromane) biosynthetic gene clusters. The orchestration of the functional dimorphism of the polyketide synthase (ChrA) ketoreductase (KR) domain (shortened as ChrA KR) with that of the KR partner (ChrB) in the bioassembly line increases the polyketide diversity and allows the fungal generation of plant chromanes (e.g., noreugenin) and phloroglucinols (e.g., 2,4,6-trihydroxyacetophenone). The simultaneous fungal biosynthesis of 1,3,6,8- and 2-acetyl-1,3,6,8-tetrahydroxynaphthalenes was addressed as well. Collectively, the work may symbolize a movement in understanding the multiple-gene-cluster involved natural product biosynthesis, and highlights the possible fungal generations of some chromane- and phloroglucinol-based phytochemicals.

Graphical abstract: Dalmanol biosyntheses require coupling of two separate polyketide gene clusters

Supplementary files

Article information

Article type
Edge Article
Submitted
19 Aug 2018
Accepted
21 Nov 2018
First published
27 Nov 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 73-82

Dalmanol biosyntheses require coupling of two separate polyketide gene clusters

Z. Z. Zhou, H. J. Zhu, L. P. Lin, X. Zhang, H. M. Ge, R. H. Jiao and R. X. Tan, Chem. Sci., 2019, 10, 73 DOI: 10.1039/C8SC03697G

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