Synthesis, Bioactivity, and QSAR Study of 3,4-Dichlorophenyl Isoxazole-Substituted Stilbene Derivatives against the Phytopathogenic Fungus Botrytis cinerea

Here, we characterized a negative single-stranded (−ss)RNA mycovirus, Botrytis cinerea mymonavirus 1 (BcMyV1), isolated from the phytopathogenic fungus Botrytis cinerea. The genome of BcMyV1 is 7863 nt in length, possessing three open reading frames (ORF1–3). The ORF1 encodes a large polypeptide containing a conserved mononegaviral RNA-dependent RNA polymerase (RdRp) domain showing homology to the protein L of mymonaviruses, whereas the possible functions of the remaining two ORFs are still unknown. The internal cDNA sequence (10-7829) of BcMyV1 was 97.9% identical to the full-length cDNA sequence of Sclerotinia sclerotiorum negative stranded RNA virus 7 (SsNSRV7), a virus-like contig obtained from Sclerotinia sclerotiorum metatranscriptomes, indicating BcMyV1 should be a strain of SsNSRV7. Phylogenetic analysis based on RdRp domains showed that BcMyV1 was clustered with the viruses in the family Mymonaviridae, suggesting it is a member of Mymonaviridae. BcMyV1 may be widely distributed in regions where B. cinerea occurs in China and even over the world, although it infected only 0.8% of tested B. cinerea strains.

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The Search for Quorum Sensing in Botrytis cinerea: Regulatory Activity of Its Extracts on Its Development

Plants ◽

10.3390/plants9020168 ◽

2020 ◽

Vol 9 (2) ◽

pp. 168

Author(s):

Esteban D. Rosero-Hernández ◽

Fernando L. Echeverri

Keyword(s):

Quorum Sensing ◽

Botrytis Cinerea ◽

Biological Activities ◽

Phytopathogenic Fungus ◽

Effective Strategies ◽

Promising Strategy ◽

Phytotoxic Effect ◽

Large Crop ◽

Germ Tubes ◽

Great Inhibition

Botrytis cinerea is a phytopathogenic fungus that causes large crop and post-harvest losses. Therefore, new and effective strategies are needed to control the disease and to reduce resistance to fungicides. Modulating pathogenicity and virulence by manipulating microbial communication is a promising strategy. This communication mechanism, called Quorum Sensing (QS), has already been reported in bacteria and yeasts; however, it has not yet been studied in B. cinerea. To establish the existence of this biochemical process in B. cinerea, we prepared extracts at different growth times (D1-D12), which were applied to fresh cultures of the same fungi. The chemical analysis of the extracts obtained from several fermentations showed different compositions and biological activities. We confirmed the presence of several phytotoxins, as well as compounds 1-phenylethanol and 3-phenylpropanol. Day five extract (0.1%) inhibited conidia germination and elongation of germ tubes, day seven extract (1%) produced the greatest phytotoxic effect in tomato leaves, and day nine extract (0.1%) was a sporulation inhibitor. In contrast, the extracts from days 7, 9, and 12 of fermentation (0.1% and 0.01%) promoted pellet and biofilm formation. Sporulation was slightly induced at 0.01%, while at 0.1% there was a great inhibition. At the highest extract concentrations, a biocidal effect was detected, but at the lowest, we observed a QS-like effect, regulating processes such as filamentation, morphogenesis, and pathogenesis. These results of the biological activity and composition of extracts suggest the existence of a QS-like mechanism in B. cinerea, which could lead to new non-biocidal alternatives for its control through interference in the pathogenicity and virulence mechanisms of the fungi.

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NADPH Oxidases Are Involved in Differentiation and Pathogenicity in Botrytis cinerea

Molecular Plant-Microbe Interactions ◽

10.1094/mpmi-21-6-0808 ◽

2008 ◽

Vol 21 (6) ◽

pp. 808-819 ◽

Cited By ~ 167

Author(s):

Nadja Segmüller ◽

Leonie Kokkelink ◽

Sabine Giesbert ◽

Daniela Odinius ◽

Jan van Kan ◽

...

Keyword(s):

Botrytis Cinerea ◽

Nicotinamide Adenine Dinucleotide ◽

Amino Acid Sequences ◽

Host Tissue ◽

Regulatory Subunit ◽

Phytopathogenic Fungus ◽

Wild Type ◽

Nadph Oxidases ◽

Knock Out

Nicotinamide adenine dinucleotide (NADPH) oxidases have been shown to be involved in various differentiation processes in fungi. We investigated the role of two NADPH oxidases in the necrotrophic phytopathogenic fungus, Botrytis cinerea. The genes bcnoxA and bcnoxB were cloned and characterized; their deduced amino acid sequences show high homology to fungal NADPH oxidases. Analyses of single and double knock-out mutants of both NADPH oxidase genes showed that both bcnoxA and bcnoxB are involved in formation of sclerotia. Both genes have a great impact on pathogenicity: whereas bcnoxB mutants showed a retarded formation of primary lesions, probably due to an impaired formation of penetration structures, bcnoxA mutants were able to penetrate host tissue in the same way as the wild type but were much slower in colonizing the host tissue. Double mutants showed an additive effect: they were aberrant in penetration and colonization of plant tissue and, therefore, almost nonpathogenic. To study the structure of the fungal Nox complex in more detail, bcnoxR (encoding a homolog of the mammalian p67phox, a regulatory subunit of the Nox complex) was functionally characterized. The phenotype of ΔbcnoxR mutants is identical to that of ΔbcnoxAB double mutants, providing evidence that BcnoxR is involved in activation of both Bcnox enzymes.

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Elicitation – a tool to improve secondary metabolites production in Melissa Officinalis L. Suspension cultures / Elicitácia ako nástroj na zlepšenie produkcie sekundárnych metabolitov v suspenzných kultúrach Melissa Officinalis L.

Acta Facultatis Pharmaceuticae Universitatis Comenianae ◽

10.1515/afpuc-2015-0012 ◽

2015 ◽

Vol 62 (s9) ◽

pp. 46-50 ◽

Cited By ~ 2

Author(s):

J. Urdová ◽

M. Rexová ◽

P. Mučaji ◽

A. Balažová

Keyword(s):

Methyl Jasmonate ◽

Botrytis Cinerea ◽

Suspension Cultures ◽

Hydroxycinnamic Acid ◽

Phytopathogenic Fungus ◽

Growth Media ◽

Melissa Officinalis ◽

Hydroxycinnamic Acid Derivatives ◽

Elicitor Treatment ◽

Metabolites Production

Abstract Our recent study is focussed on the investigation of the influence of biotic (Botrytis cinerea, methyl jasmonate) and abiotic (cadmium and cobalt chloride) elicitors on Melissa officinalis L. (lemon balm) suspension cultures production properties. The plant material was treated with different concentrations of methyl jasmonate (10 and 100 μmol.l−1), with a phytopathogenic fungus hydrolyzate (Botrytis cinerea, 1 and 2 ml with glucose equivalent 24 μg.ml−1), cadmium and cobalt (II) chloride (both at concentrations 100 μmol.l−1 and 1 μmol.l−1). Elicited suspension cultures were harvested after 24, 48 and 72 h of elicitor treatment. The elicitation effect was evaluated based on hydroxycinnamic acid derivatives content expressed as rosmarinic acid in dose- and time-dependent manners. The Botrytis cinerea hydrolyzate exhibited the best effect on Melissa officinalis L. suspension cultures production properties among biotic elicitors (glucose equivalent 24 mg.ml−1, 1 ml, after 72 h of treatment). The hydroxycinnamic acid derivatives content increased in triplicate compared to non-elicited samples. Methyl jasmonate affected the suspension cultures production properties moderately at concentration 10 μmol.l−1. Chlorides salts of cobalt and cadmium stimulated phenolic compounds production effectively at concentrations 100 μmol.l−1. The presence of cobalt and cadmium ions in suspension cultures growth media increased the hydroxycinnamic acid derivatives content twofold and quadruple, respectively.

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Estrogenic Active Stilbene Derivatives as Anti-Cancer Agents: A DFT and QSAR Study

IEEE/ACM Transactions on Computational Biology and Bioinformatics ◽

10.1109/tcbb.2017.2779505 ◽

2019 ◽

Vol 16 (2) ◽

pp. 560-568

Author(s):

Bilal Nizami ◽

Elham Mousavinezhad Sarasia ◽

Mehbub I. K. Momin ◽

Bahareh Honarparvar

Keyword(s):

Qsar Study ◽

Anti Cancer ◽

Stilbene Derivatives

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Comparative analysis of Botrytis cinerea in response to the microbial secondary metabolite benzothiazole using iTRAQ-based quantitative proteomics

Phytopathology ◽

10.1094/phyto-11-20-0503-r ◽

2020 ◽

Author(s):

Kaidi Cui ◽

Leiming He ◽

Yunhe Zhao ◽

Wei Mu ◽

Jin Lin ◽

...

Keyword(s):

Antifungal Activity ◽

Botrytis Cinerea ◽

Mitochondrial Membrane ◽

Molecular Mechanisms ◽

Glyoxylate Cycle ◽

Pathogenic Fungi ◽

Phytopathogenic Fungus ◽

Future Research ◽

Design And Synthesis ◽

The Glyoxylate Cycle

Benzothiazole is a microbial volatile compound with strong antifungal activity against the phytopathogenic fungus Botrytis cinerea, but its mode of action against fungi remains largely unknown. Understanding the molecular mechanisms underlying its activity could aid the design and synthesis of new similar compounds against pathogenic fungi. Based on the results of morphological and antifungal activity assays, B. cinerea was exposed to 2.5 μL/L benzothiazole for 12, 24 and 48 h, and an iTRAQ-based quantitative proteomic analysis showed that 378 out of 5,110 identified proteins were differentially expressed proteins (DEPs). The majority of these DEPs were associated with carbohydrate metabolism, oxidation-reduction processes and energy production. Further analysis showed that benzothiazole inhibited mitochondrial membrane organization and decreased the mitochondrial membrane potential of B. cinerea. In addition, the key enzymes of the glyoxylate cycle were downregulated after benzothiazole treatment, and a biochemical analysis indicated that the inhibition of the glyoxylate cycle by benzothiazole blocked nutrient availability and interfered with ATP generation. This study provides markers for future research of the molecular responses of B. cinerea to benzothiazole stress.

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