Synthetic-biology-based discovery of a fungal macrolide from <i>Macrophomina phaseolina</i>

Morishita, Yohei; Taniguchi, Tohru; Adachi, Kiyohiro; Fujita, Makoto; Asai, Toshinobu

doi:10.1039/d0ob00519c

Cited by 19 publications

(16 citation statements)

References 17 publications

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“…Phanerochaete chrysosporium is a decomposer in carbon cycle [93]. Macrophomina phaseolina produced macrolide [94]. These results suggested that the microbial network topology structure and composition were substantially shaped in the M. incognita-infested soils in this mountain ecosystem.…”

Section: Discussionmentioning

confidence: 78%

Intergrated metagenomics and metabolomics analysis discovers nematicidal microbes, enzymes and metabolites from the plant rhizosphere microbiota

Lin

Yuan

Ruan

et al. 2021

Preprint

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Background: Meloidogyne incognita infestation has led to huge economic loss worldwide. Nematicidal microorganisms provide an effective strategy to control M. incognita . In order to find microorganisms and new metabolites with high nematicidal activity, we collected M. incognita - infested tobacco rhizosphere soils and non-infested rhizosphere soils, and investigated functional genes, microbial community and network, and metabolites via metagenomics and metabolomics analyses. Results: Rhizosphere microbial composition, function, network and metabolites were altered accompanying with M . incognita infestation. Abundances of nematicidal microorganisms, metabolites, antibiotics and extracellular enzymes’ genes in the non-infested rhizosphere microbiota were higher than those in M. incognita -infested rhizosphere microbiota. Abundances of functions genes involved in secondary metabolites biosynthesis and carbohydrate transport and metabolism in the non-infested rhizosphere microbiota were higher than M. incognita -infested rhizosphere microbiota. Contents of 102 metabolites were different in the two rhizosphere microbiota. Contents of 35 metabolites (acetophenone, indole-3-acetic acid, etc.) in the non-infested rhizosphere microbiota were higher than those in M . incognita -infested rhizosphere microbiota. Acetophenone showed high nematicidal (LC 50 = 0.66 μg/ml) and repellent activities against M. incognita . Co-occurrence network analyses found Bacillus showed a stronger positive correlation with acetophenone. Nematicidal microorganisms were isolated from soils, and one isolate of B . amyloliquefaciens W1 produced acetophenone. Exposing J2 larvae of M. incognita to liquid culture filtrate of W1 resulted in a mortality rate of 98.8% after 24 h. Other isolates such as Aspergillus , Achromobacter , Acinetobacter , Bacillus , Burkholderia , Comamonas , Enterobacter , Lysobacter , Microbacterium , Paenibacillus , Pantoea , Pseudomonas , Streptomyces and Variovorax produced extracellular nematicidal enzymes. Conclusions: M eloidogyne incognita -infested rhizophere microbiota differed in microbial community composition, network structure, function genes and metabolites contents from the non-infested rhizosphere microbiota. Abundances of nematicidal microorganisms and metabolites, and genes involved in secondary metabolites biosynthesis and carbohydrate metabolism in the non-infested rhizosphere microbiota were higher than those in M . incognita -infested rhizosphere microbiota. Network complexity in M . incognita -infested rhizosphere microbiota was lower than that in non-infested rhizosphere microbiota. Keystone microorganisms were also different between these two networks. Acetophenone was identified as a new nematicidal compound with high activity to kill and repel M. incognita , and B. amyloliquefacens W1 isolated from non-infested soil produced acetophenone against M. incognita .

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Section: Discussionmentioning

confidence: 78%

Intergrated metagenomics and metabolomics analysis discovers nematicidal microbes, enzymes and metabolites from the plant rhizosphere microbiota

Lin

Yuan

Ruan

et al. 2021

Preprint

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“…mandshuricum ( Xixin ) with synchrotron radiation and 1 . Most recently, Morishita, Fujita, et al solved phaseolide A ( 22 ), a 12-membered macrolactone genomically mined from Macrophomina phaseolina , using the Cl congener of 1 . For metabolite analysis, Fujita et al coupled HPLC with 1 to analyze reductive reactions on organic compounds by Saccharomyces cerevisiae .…”

Section: Diversity Of Crystalline Matricesmentioning

confidence: 99%

Application of Crystalline Matrices for the Structural Determination of Organic Molecules

Cardenal

Ramadhar

2021

ACS Cent. Sci.

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While single-crystal X-ray diffraction (SC-XRD) is one of the most powerful structural determination techniques for organic molecules, the requirement of obtaining a suitable crystal for analysis limits its applicability, particularly for liquids and amorphous solids. The emergent use of preformed porous crystalline matrices that can absorb organic compounds and stabilize them via host–guest interactions for observation via SC-XRD offers a way to overcome this hindrance. A topical and current discussion of SC-XRD in organic chemistry and the use of preformed matrices for the in crystallo analysis of organic compounds, with a particular focus on the absolute structure determination of chiral molecules, is presented. Preformed crystalline matrices that are covered include metal–organic frameworks (MOFs) as used in the crystalline sponge method, metal–organic polyhedra (MOPs, coordination cages), porous organic materials (POMs)/porous organic molecular crystals (POMCs), and biological scaffolds. An outlook and perspective on the current technology and on its future directions is provided.

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“…Despite the immense potential of the method and recent improvements and successes (Hoshino et al, 2016;Hayes et al, 2016;Ramadhar et al, 2015a,b;Easun et al, 2017;Cuenca et al, 2016;Cardenal & Ramadhar, 2021;Bosch et al, 2014;Goh et al, 2018;Inokuma et al, 2016Inokuma et al, , 2014Kersten et al, 2017;Lee et al, 2017;Li et al, 2019;Matsuda et al, 2016;Mitsuhashi et al, 2018;Morishita et al, 2020;Morita et al, 2020;Rissanen, 2017;Vinogradova et al, 2014;Wada et al, 2018;Waldhart et al, 2016;Yoshioka et al, 2016;Yuan et al, 2019;Zigon et al, 2015;de Poel et al, 2019;Urban et al, 2016;Sakurai et al, 2017) it is still far from being the universal way to determine the structure of troublesome compounds, because the method still faces some serious challenges: the time-consuming process of analysis is highly dependent on the analytes and must be carried out in separate batches for each sample. The obtained crystal structures are often crystallographically challenging because of the nature of the particular host-guest interactions (Cardenal & Ramadhar, 2021;Hoshino et al, 2016;Zigon et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

The benefits of Cu Kβ radiation for the single-crystal X-ray structure determination of crystalline sponges

Meurer¹,

Eßen²,

Kühn³

et al. 2022

Int Union Crystallogr J

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The crystalline sponge method facilitates the X-ray structure determination of samples that do not crystallize or are too sparsely available to afford viable crystallization. By including these materials in a metal–organic framework, the structure of the guest molecules can be determined. Some of the inherent difficulties of this method are discussed and the use of Cu Kβ radiation is presented as a simple and effective means to improve the quality of the diffraction data that can be obtained from a sponge crystal.

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Synthetic-biology-based discovery of a fungal macrolide from Macrophomina phaseolina

Abstract: Genome mining and heterologous biosynthesis led to the discovery of a 12 membered macrolide from Macrophomina phaseolina.

Cited by 19 publications

References 17 publications

Intergrated metagenomics and metabolomics analysis discovers nematicidal microbes, enzymes and metabolites from the plant rhizosphere microbiota

Intergrated metagenomics and metabolomics analysis discovers nematicidal microbes, enzymes and metabolites from the plant rhizosphere microbiota

Application of Crystalline Matrices for the Structural Determination of Organic Molecules

The benefits of Cu Kβ radiation for the single-crystal X-ray structure determination of crystalline sponges

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