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Issue 46, 2020
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The sporothriolides. A new biosynthetic family of fungal secondary metabolites

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Abstract

The biosynthetic gene cluster of the antifungal metabolite sporothriolide 1 was identified from three producing ascomycetes: Hypomontagnella monticulosa MUCL 54604, H. spongiphila CLL 205 and H. submonticulosa DAOMC 242471. A transformation protocol was established, and genes encoding a fatty acid synthase subunit and a citrate synthase were simultaneously knocked out which led to loss of sporothriolide and sporochartine production. In vitro reactions showed that the sporochartines are derived from non-enzymatic Diels–Alder cycloaddition of 1 and trienylfuranol A 7 during the fermentation and extraction process. Heterologous expression of the spo genes in Aspergillus oryzae then led to the production of intermediates and shunts and delineation of a new fungal biosynthetic pathway originating in fatty acid biosynthesis. Finally, a hydrolase was revealed by in vitro studies likely contributing towards self-resistance of the producer organism.

Graphical abstract: The sporothriolides. A new biosynthetic family of fungal secondary metabolites

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Supplementary files

Article information


Submitted
04 Sep 2020
Accepted
20 Oct 2020
First published
21 Oct 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 12477-12484
Article type
Edge Article

The sporothriolides. A new biosynthetic family of fungal secondary metabolites

D. Tian, E. Kuhnert, J. Ouazzani, D. Wibberg, J. Kalinowski and R. J. Cox, Chem. Sci., 2020, 11, 12477
DOI: 10.1039/D0SC04886K

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