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. 2023 Nov 22;145(46):25080-25085.
doi: 10.1021/jacs.3c10179. Epub 2023 Nov 10.

Genome Mining from Agriculturally Relevant Fungi Led to a d-Glucose Esterified Polyketide with a Terpene-like Core Structure

Chunsheng Yan, Wenyu Han, Qingyang Zhou, Kanji Niwa, Melody J Tang, Jessica E Burch, Yalong Zhang, David A Delgadillo, Zuodong Sun, Zhongshou Wu, Steven E Jacobsen, Hosea Nelson, K N Houk, Yi Tang

Genome Mining from Agriculturally Relevant Fungi Led to a d-Glucose Esterified Polyketide with a Terpene-like Core Structure

Chunsheng Yan et al. J Am Chem Soc. .

Abstract

Comparison of biosynthetic gene clusters (BGCs) found in devastating plant pathogens and biocontrol fungi revealed an uncharacterized and conserved polyketide BGC. Genome mining identified the associated metabolite to be treconorin, which has a terpene-like, trans-fused 5,7-bicyclic core that is proposed to derive from a (4 + 3) cycloaddition. The core is esterified with d-glucose, which derives from the glycosidic cleavage of a trehalose ester precursor. This glycomodification strategy is different from the commonly observed glycosylation of natural products.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Examples of SMs biosynthesized from fungal BGCs anchored by HPRKSs. Treconorin was discovered in this work.
Figure 2
Figure 2
Bioinformatic analysis and reconstitution of tre BGC. (A) Comparison of the tre BGC in ThT22 to homologous BGCs in four major plant pathogens. (B) Metabolic analysis of heterologous reconstitution of the tre BGC in A. nidulans, except trace i, which is from ThT22 to indicate the presence of 5. Selected ion monitoring traces at the indicated m/z values are shown. The multipliers indicated are used to magnify certain peaks. * indicates peaks (m/z+ 499) that are present in the control and are not related to the expression of tre BGC.
Figure 3
Figure 3
(Top) Proposed biosynthetic pathway of compounds 5 and 3. (Bottom) Computed energy profile for the proposed mechanism from compound 11′ to compound 7′. For the 3D structures of TS1 and TS2, unimportant hydrogens have been omitted for clarity, and bond lengths for partially formed bonds are given in Å. The trehalose is replaced by methyl to simplify the computation. Computational method: ωB97X-D/def2-QZVPP/SMD(water)//ωB97X-D/def2-SVP/IEEPCM(water) under standard state (298 K, 1 atm, 1 M).
See this image and copyright information in PMC

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