Phyllostictines A–D, oxazatricycloalkenones produced by Phyllosticta cirsii, a potential mycoherbicide for Cirsium arvense biocontrol

Evidente, Antonio; Cimmino, Alessio; Andolfi, Anna; Vurro, Maurizio; Zonno, Maria Chiara; Cantrell, Charles L.; Motta, Andréa

doi:10.1016/j.tet.2007.12.010

Cited by 49 publications

(53 citation statements)

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“…The N-ethyl b-lactam ring appears to be less important while the importance of other rings remains to be ascertained. 182 Antimicrobial and zootoxic activities were assayed for (-)-phyllostictines A and B at up to 100 lg/disk and were completely inactive against G. candidum and E. coli Migula (Gram-negative bacteria). (-)-Phyllostictine A at 5 lg/disk inhibited Lactobacillus sp.…”

Section: Phytotoxins Produced By Phyllosticta Cirsii New Phytotoxic Omentioning

confidence: 99%

“…The integrity of oxazatricycloalkenone structure in (-)-phyllostictine A appears important for antimicrobial and zootoxic activities. 182 Phyllostictines A-D are the first fungal metabolites described for the oxatricycloalkanenone group as natural compounds with interesting biological activities. Phyllostictine A also showed both herbicidal and antibacterial (Grampositive bacteria) properties.…”

Section: Phytotoxins Produced By Phyllosticta Cirsii New Phytotoxic Omentioning

confidence: 99%

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Relationships between the stereochemistry and biological activity of fungal phytotoxins

2011

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Toxins produced by phytopathogenic fungi assume great importance because of their involvement in several plant diseases. Although such pathogens are known to have seriously damaged crops, forest, and environmental resources, they represent a very important tool to develop new environmentally friendly herbicides and fungicides. This review deals with the relationships between the biological activity of some phytotoxins produced by pathogenic fungi for major forest plants and for damaging weeds and their stereochemistry. In particular, the methods used to determine their relative and/or absolute configuration will be illustrated. These include the application of Mosher's and Murata's methods, X-ray diffractometric analysis, circular dichroism, and the use of computational methods to determine the theoretical optical rotatory power as well as the CD spectrum. The importance of determining the absolute configuration to achieve the total synthesis of some phytotoxins, interesting for their potential practical application, is also discussed.

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Section: Phytotoxins Produced By Phyllosticta Cirsii New Phytotoxic Omentioning

confidence: 99%

Section: Phytotoxins Produced By Phyllosticta Cirsii New Phytotoxic Omentioning

confidence: 99%

Relationships between the stereochemistry and biological activity of fungal phytotoxins

2011

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“…2 In 2008, Evidente et al reported the isolation and structural elucidation of a new class of natural herbicide produced by the fungus Phyllosticta cirsii. 3 Four new compounds named phyllostictines A-D (1-4) based upon a unique oxazatricycloalkenone skeleton were identified ( Figure 1). Members of the phyllostictine family show variation in the size of the lactam and carbocyclic rings, the nature of the substituent at C-5, and the level of oxidation.…”

Section: Introductionmentioning

confidence: 99%

Ring closing metathesis reactions of α-methylene-β-lactams: application to the synthesis of a simplified phyllostictine analogue with herbicidal activity

et al. 2015

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Michael. (2015) Ring closing metathesis reactions of α-methylene-β-lactams : application to the synthesis of a simplified phyllostictine analogue with herbicidal activity. Organic & Biomolecular Chemistry, Volume 13 (Number 28). pp. 7655-7663. Permanent WRAP url:http://wrap.warwick.ac.uk/70250 Copyright and reuse:The Warwick Research Archive Portal (WRAP) makes this work by researchers of the University of Warwick available open access under the following conditions. Copyright © and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable the material made available in WRAP has been checked for eligibility before being made available.Copies of full items can be used for personal research or study, educational, or not-forprofit purposes without prior permission or charge. Provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. Ring closing metathesis (RCM) reactions of -methylene--lactams are used to construct strained 11-and 12-membered macrocycles that mimic key structural elements of phyllostictine A. The highest yield and stereoselectivity was achieved making 12-membered macrocycle Z-19 with use of a p-methoxyphenyl group on the lactam nitrogen. Interestingly, substrate concentration had an important influence on the stereochemical course of the reaction. A simplified analogue produced using this approach displays phytotoxic activity against Chlamydomonas reinhardtii suggesting that the -methylene--lactam subunit is responsible, at least in part, for the herbicidal activity of phyllostictine A .

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“…are commonly known to produce various kinds of secondary metabolites for example, Phyllosticta derivatives exhibiting growth-inhibitory activity in five cancer cell lines have been isolated from P. cirsii. Phytotoxins, phyllosinol, brefeldin, and PMtoxin are known as fungal pathogenic derivatives from Phyllosticta [20]. Recently, the phytotoxins guignarenones A-F and alaguignardic acid have been isolated which could stimulate the development of herbicides of natural origin [21][22][23].…”

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confidence: 99%

“…In addition, antimicrobial activity active on growth inhibitor of Escherichia coli, Bacillus cereus, and Pseudomonas aeruginosa [24][25]. P. cirsii has been isolated from diseased leaves of Cirsium arvense and it evaluated as a potential biocontrol agent of this noxious perennial weed; furthermore, it produces different phytotoxic metabolites with potential herbicidal activity when grown in liquid cultures [20]. …”

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Lignocellulolytic Capability of Endophytic Phyllosticta sp.

CB¹

2017

J Bacteriol Mycol

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The Dothideomycetes represent the largest fungal class of Ascomycota. It is an ubiquitous class of fungi whose members span a wide spectrum of lifestyles and host interactions. The endophytic fungus Phyllosticta is one members of the Dothideomycetes, causing disease in economic crops. Phyllosticta was screened for the degradation of lignocellulosic biomass of commercial relevance, such as rice straw, rice husk, sorghum, wheat straw, miscanthus, lavender flower, and lavender straw. The highest degrading strains were identified from an initial screen and further analyzed for the secretion of lignocellulosic enzymes during growth on the different biomasses. With Phyllosticta capitalensis (MFLUCC14-0233), maximum activity of arabinase (944.18 U/ml culture), cellulase (27.10 U/ml), xylanase (10.85 U/ml), pectinase (465.47 U/ml), and laccase (35.68 U/ml) activities could be detected in the secretome during growth on lavender flowers and lavender straw. Phyllosticta capitalensis is thus an interesting new strain for the production of lignocellulosic enzymes during growth on cheap agro-industrial biomass. Keywords:Agro-industrial residues; Biological pretreatment; Dothideomycetes; Lignocellulosic biomass; Lignocellulytic enzyme; Phyllosticta IntroductionThe Dothideomycetes represent the largest fungal class within the phylum Ascomycota. It is a ubiquitous class of fungi whose members span a wide spectrum of lifestyles and host interactions [1][2][3]. Members of the Dothideomycetes can cause disease in every major crop [4]. Approximately 1,300 genera and 19,000 species have been identified either as endophytes, plant pathogens, or as saprophytes degrading plant biomass, thus threatening agriculture and food security throughout the world [5][6][7][8]. In addition to their mode of life, the Dothideomycetes are known for producing secondary metabolites grouped into four main categories based on their biosynthetic origin: polyketides, non-ribosomal peptides, terpenoids and tryptophan derivatives [9]. These secondary metabolites can be both toxic and beneficial to plants and humankind in applications such as agrochemicals, antibiotics, immunosuppressant's, antiparasitics, antioxidants and anticancer agents [10]. New Dothideomycetes are still being discovered worldwide and a large number of these strains remained unexplored regarding their potential use in biotechnology [11][12].Endophytes provide a broad variety of bioactive secondary metabolites with unique structures and so this class of fungi could be used as potential "nanofactories" producing a range of "green" alternatives to currently employed chemicals [13]. Although the ecological significance of endophytes is not completely clear, it is known that these fungi can exploit dead leaves immediately after their senescence and before they fall from the tree [14], and so could be also exploited for the production of enzymes acting on plant biomass.A well-known representative of Dothideomycetes fungi in metabolite studies is Phyllosticta (with a Guignardia anamorph)...

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Phyllostictines A–D, oxazatricycloalkenones produced by Phyllosticta cirsii, a potential mycoherbicide for Cirsium arvense biocontrol

Cited by 49 publications

References 11 publications

Relationships between the stereochemistry and biological activity of fungal phytotoxins

Relationships between the stereochemistry and biological activity of fungal phytotoxins

Ring closing metathesis reactions of α-methylene-β-lactams: application to the synthesis of a simplified phyllostictine analogue with herbicidal activity

Lignocellulolytic Capability of Endophytic Phyllosticta sp.

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