Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae

Rieger, Patrick H; Liermann, Johannes C.; Opatz, Till; Anke, Heidrun; Thines, Eckhard

doi:10.1038/ja.2010.31

Cited by 16 publications

(16 citation statements)

References 22 publications

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“…Caripia montagnei ), was found to inhibit conidial germination and appressorium formation in P. oryzae without being cytotoxic, antibacterial and nematicidal (Rieger et al, 2010). Candida biofilm formation was reduced by 63–98% when sub-MIC levels of Boesenbergia pandurata (finger root) oil were used (Taweechaisupapong et al, 2010).…”

Section: New Ecologically Friendly Strategies To Manage Fungal Biofilmentioning

confidence: 99%

Fungal Biofilms: Targets for the Development of Novel Strategies in Plant Disease Management

et al. 2017

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The global food supply has been facing increasing challenges during the first decades of the 21st century. Disease in plants is an important constraint to worldwide crop production, accounting for 20–40% of its annual harvest loss. Although the use of resistant varieties, good water management and agronomic practices are valid management tools in counteracting plant diseases, there are still many pathosystems where fungicides are widely used for disease management. However, restrictive regulations and increasing concern regarding the risk to human health and the environment, along with the incidence of fungicide resistance, have discouraged their use and have prompted for a search for new efficient, ecologically friendly and sustainable disease management strategies. The recent evidence of biofilm formation by fungal phytopathogens provides the scientific framework for designing and adapting methods and concepts developed by biofilm research that could be integrated in IPM practices. In this perspective paper, we provide evidence to support the view that the biofilm lifestyle plays a critical role in the pathogenesis of plant diseases. We describe the main factors limiting the durability of single-site fungicides, and we assemble the current knowledge on pesticide resistance in the specific context of the biofilm lifestyle. Finally, we illustrate the potential of antibiofilm compounds at sub-lethal concentrations for the development of an innovative, eco-sustainable strategy to counteract phytopathogenic fungi. Such fungicide-free solutions will be instrumental in reducing disease severity, and will permit more prudent use of fungicides decreasing thus the selection of resistant forms and safeguarding the environment.

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Section: New Ecologically Friendly Strategies To Manage Fungal Biofilmentioning

confidence: 99%

Fungal Biofilms: Targets for the Development of Novel Strategies in Plant Disease Management

et al. 2017

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“…In 2010 Rieger et al reported the flat structure of the fungal secondary metabolite (+)‐caripyrin ( 1 ; Figure 1), which they isolated from submerged cultures of the basidiomycete Caripia montagnei . The compound exhibits selective and strong inhibition of conidial germination in the rice blast fungus Magnaporthe oryzae , the causal agent of blast, a devastating disease in cultivated rice 1. However, the absolute configuration of its two stereogenic centers remained unknown.…”

Section: Introductionmentioning

confidence: 99%

Assignment of the Absolute Configuration and Total Synthesis of (+)‐Caripyrin

Andernach

Opatz

2014

Eur J Org Chem

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The antifungal secondary metabolite (+)‐caripyrin was studied by vibrational circular dichroism spectroscopy. Analysis of the recorded data, with the Boltzmann weighted‐average of the spectra calculated at the B3LYP/6‐311G(d,p) level of theory for all relevant conformers, unequivocally proved the (R,R)‐configuration for the dextrorotatory natural product. Based on this finding, a short enantioselective synthesis of (+)‐caripyrin was developed.

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“…13 The fungal strain IBWF-029-96 was identified as Penicillium sp. Its conidiophores showed all morphological characteristics of the genus as described.…”

Section: Biological Assaysmentioning

confidence: 99%

“…13 Seeds of Setaria italica, Lepidium sativum, O. sativa CO-39 and Triticum aestivum RIBAND were used. The assay was performed thrice.…”

Section: Biological Assaysmentioning

confidence: 99%

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GKK1032A2, a secondary metabolite from Penicillium sp. IBWF-029-96, inhibits conidial germination in the rice blast fungus Magnaporthe oryzae

et al. 2011

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The rice blast fungus Magnaporthe oryzae is the most important pathogen on cultivated rice because of its economic relevance and destructiveness. 1 Blast disease caused by this heterothallic ascomycete destroys about 10-30% rice yield every year. 2 In order to infect and colonize the host plant Oryza sativa, conidia of the fungus attach to the leaf surface and germinate by sending out a germ tube. Induced by the hard hydrophobic surface, appressoria required for penetration differentiate. Within the specialized infection structure compatible solutes, for example, glycerol, accumulate. 3 The solutes are retained within the cell by a melanin layer. As a consequence, water flows into the infection structure to generate turgor required for a mechanically penetration of the plant cuticle. As the functionality of the appressorium is an essential prerequisite for a successful infection of the host plant, the melanin layer is a pathogenicity factor in M. oryzae. Agrochemicals interfering with the biosynthesis of the biopolymer, for example, tricyclazole, have been successfully used in the past as protective agents. 4 After penetration, the hyphae disperse within the plant to form conidiophores and conidia. The spores are spread in the field via wind and water. 2 Due to the resistance development against commercially available fungicides, there is a demand for lead structures for the development of novel fungicides. 4 Secondary metabolites from nature have in the past been used as lead structures for successful pesticides. The widely used class of QoI (quinone outside inhibitor)-fungicides is based on the structure of strobilurin A, a secondary metabolite found in cultures of the basidiomycete Strobilurus tenacellus. 5 As fungi represent an almost inexhaustible reservoir for natural compounds, screening approaches are conducted for the identification of new secondary metabolites interfering either with pathogenic differentiation or fungal vegetative growth. In this course, compound GKK1032A 2 (1) was identified from cultures of the fungus Penicillium sp. IBWF-029-96. The compound has been described as a metabolite from fungal cultures. In this note, we describe a biological activity of this compound, which has not been reported before. 6,7 M. oryzae strain 70-15 was obtained from the Fungal Genetics Stock Centre, Kansas City, KS, USA. The strain was cultured on complete medium (CM) medium as described previously. 8 Botrytis cinerea, Fusarium graminearum and Phytophthora infestans were provided by BASF SE. EXPERIMENTAL PROCEDURE Organisms Fermentation and isolationThe strain Penicillium sp. IBWF-029-96 was fermented in yeast malt glucose medium in a 20-l fermenter (Biostat A-20, Braun Melsungen, Melsungen, Germany) at room temperature with aeration (4.5 l min À1 ) and agitation (120 r.p.m.). A well-grown culture (200 ml) in the same medium was used as inoculum. Daily samples were withdrawn to measure pH, glucose and maltose content as well as mycelial dry weight and in order to quantify the bioactive secondary metabolite ...

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Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae

Cited by 16 publications

References 22 publications

Fungal Biofilms: Targets for the Development of Novel Strategies in Plant Disease Management

Fungal Biofilms: Targets for the Development of Novel Strategies in Plant Disease Management

Assignment of the Absolute Configuration and Total Synthesis of (+)‐Caripyrin

GKK1032A2, a secondary metabolite from Penicillium sp. IBWF-029-96, inhibits conidial germination in the rice blast fungus Magnaporthe oryzae

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