Phytotoxins: Chemistry, Bioactivity and Potential Practical Applications

A special issue of Toxins (ISSN 2072-6651).

Deadline for manuscript submissions: closed (31 July 2011) | Viewed by 50986

Special Issue Editor

1. Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
2. Institute of Sciences of Food Production, National Research Council, Via Amendola 122/O, 70125 Bari, Italy
Interests: Fungi; Bacterial; plant; metabolites; chemistry; spectroscopy; stereochemistry; biological activity; structure-activity relationships
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phytotoxins are secondary metabolites produced by phytopathogenic microrganisms playing an important role in plant disease development. The chemical nature of these metabolites range from low molecular weight compounds, including all classes of natural products as terpenes, chromanones, butenolides, pyrones, macrolides, aromatic derivatives, amino acids etc., to high molecular weight compounds as proteins, glycoproteins and polysaccharides.

The serious disease induced by both phytopathogenic fungi and bacteria on agrarian as well as on ornamental and forestall plants with consequent heavy losses and damages to the agriculture and environmental patrimony, have prompted multisciplinary studies involving plant pathologists and physiologists as well as natural substance chemists. These studies, which are aimed to know the mechanisms of pathogenesis and to find an environmental friendly control of plant disease, have carried out to the isolation and chemical and biological characterization of several non-host and few host specific phytotoxins.

Several phytotoxins, at various concentrations have showed also different interesting biological activities including antimicrobial, herbicidal and also pharmacological properties. The isolation and chemical characterization of phytotoxins have given an important contribute, together with epidemiological, morphological and biochemical studied, to the correct classification of the microrganism producer. Furthermore, the isolation of toxin natural analogues as well as the preparation of chemical derivatives have allowed to carry out structure-activity relationships investigation and studies on their mode of action,  while very few attempts have made to realize simple, convenient and enantioselective syntheses of phytotoxins, and this is frequently due to their structural complexity.

However, the interesting biological activities of phytotoxins as well their potential practical application in different fields also have prompted studies for their large scale production through the selection of the best fungal or bacterial strain and growth conditions. Furthermore, studies were also carried out for the development of methods, including  HPLC, GC or LC/MS, UV, ionic chromatography, immunochemistry, for the rapid and specific analysis of the toxins in complex samples.

Prof. Dr. Antonio Evidente
Guest Editor

Keywords

  • phytotoxins
  • phytopathogenic fungi and bacteria
  • plant disease
  • chemical and biological properties

Published Papers (4 papers)

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Research

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262 KiB  
Article
Studies in the Use of Magnetic Microspheres for Immunoaffinity Extraction of Paralytic Shellfish Poisoning Toxins from Shellfish
by Raymond Devlin, Katrina Campbell, Kentaro Kawatsu and Christopher Elliott
Toxins 2011, 3(1), 1-16; https://0-doi-org.brum.beds.ac.uk/10.3390/toxins3010001 - 04 Jan 2011
Cited by 7 | Viewed by 9864
Abstract
Paralytic shellfish poisoning (PSP) is a potentially fatal human health condition caused by the consumption of shellfish containing high levels of PSP toxins. Toxin extraction from shellfish and from algal cultures for use as standards and analysis by alternative analytical monitoring methods to [...] Read more.
Paralytic shellfish poisoning (PSP) is a potentially fatal human health condition caused by the consumption of shellfish containing high levels of PSP toxins. Toxin extraction from shellfish and from algal cultures for use as standards and analysis by alternative analytical monitoring methods to the mouse bioassay is extensive and laborious. This study investigated whether a selected MAb antibody could be coupled to a novel form of magnetic microsphere (hollow glass magnetic microspheres, brand name Ferrospheres-N) and whether these coated microspheres could be utilized in the extraction of low concentrations of the PSP toxin, STX, from potential extraction buffers and spiked mussel extracts. The feasibility of utilizing a mass of 25 mg of Ferrospheres-N, as a simple extraction procedure for STX from spiked sodium acetate buffer, spiked PBS buffer and spiked mussel extracts was determined. The effects of a range of toxin concentrations (20–300 ng/mL), incubation times and temperature on the capability of the immuno-capture of the STX from the spiked mussel extracts were investigated. Finally, the coated microspheres were tested to determine their efficiency at extracting PSP toxins from naturally contaminated mussel samples. Toxin recovery after each experiment was determined by HPLC analysis. This study on using a highly novel immunoaffinity based extraction procedure, using STX as a model, has indicated that it could be a convenient alternative to conventional extraction procedures used in toxin purification prior to sample analysis. Full article
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Review

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7521 KiB  
Review
Phytotoxins Produced by Fungi Associated with Grapevine Trunk Diseases
by Anna Andolfi, Laura Mugnai, Jordi Luque, Giuseppe Surico, Alessio Cimmino and Antonio Evidente
Toxins 2011, 3(12), 1569-1605; https://0-doi-org.brum.beds.ac.uk/10.3390/toxins3121569 - 20 Dec 2011
Cited by 162 | Viewed by 15563
Abstract
Up to 60 species of fungi in the Botryosphaeriaceae family, genera Cadophora, Cryptovalsa, Cylindrocarpon, Diatrype, Diatrypella, Eutypa, Eutypella, Fomitiporella, Fomitiporia, Inocutis, Phaeoacremonium and Phaeomoniella have been isolated from decline-affected grapevines all around the [...] Read more.
Up to 60 species of fungi in the Botryosphaeriaceae family, genera Cadophora, Cryptovalsa, Cylindrocarpon, Diatrype, Diatrypella, Eutypa, Eutypella, Fomitiporella, Fomitiporia, Inocutis, Phaeoacremonium and Phaeomoniella have been isolated from decline-affected grapevines all around the World. The main grapevine trunk diseases of mature vines are Eutypa dieback, the esca complex and cankers caused by the Botryospheriaceae, while in young vines the main diseases are Petri and black foot diseases. To understand the mechanism of these decline-associated diseases and the symptoms associated with them, the toxins produced by the pathogens involved in these diseases were isolated and characterised chemically and biologically. So far the toxins of only a small number of these decline fungi have been studied. This paper presents an overview of the toxins produced by the most serious of these vine wood pathogens: Eutypa lata, Phaeomoniella chlamydospora, Phaeoacremonium aleophilum and some taxa in the Botryosphaeriaceae family, and examines how these toxins produce decline symptoms. The chemical structure of these metabolites and in some cases their vivotoxin nature are also discussed. Full article
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726 KiB  
Review
Chemical and Metabolic Aspects of Antimetabolite Toxins Produced by Pseudomonas syringae Pathovars
by Eva Arrebola, Francisco M. Cazorla, Alejandro Perez-García and Antonio de Vicente
Toxins 2011, 3(9), 1089-1110; https://0-doi-org.brum.beds.ac.uk/10.3390/toxins3091089 - 31 Aug 2011
Cited by 39 | Viewed by 10684
Abstract
Pseudomonas syringae is a phytopathogenic bacterium present in a wide variety of host plants where it causes diseases with economic impact. The symptoms produced by Pseudomonas syringae include chlorosis and necrosis of plant tissues, which are caused, in part, by antimetabolite toxins. This [...] Read more.
Pseudomonas syringae is a phytopathogenic bacterium present in a wide variety of host plants where it causes diseases with economic impact. The symptoms produced by Pseudomonas syringae include chlorosis and necrosis of plant tissues, which are caused, in part, by antimetabolite toxins. This category of toxins, which includes tabtoxin, phaseolotoxin and mangotoxin, is produced by different pathovars of Pseudomonas syringae. These toxins are small peptidic molecules that target enzymes of amino acids’ biosynthetic pathways, inhibiting their activity and interfering in the general nitrogen metabolism. A general overview of the toxins’ chemistry, biosynthesis, activity, virulence and potential applications will be reviewed in this work. Full article
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1296 KiB  
Review
Modes of Action of Microbially-Produced Phytotoxins
by Stephen O. Duke and Franck E. Dayan
Toxins 2011, 3(8), 1038-1064; https://0-doi-org.brum.beds.ac.uk/10.3390/toxins3081038 - 22 Aug 2011
Cited by 91 | Viewed by 13218 | Correction
Abstract
Some of the most potent phytotoxins are synthesized by microbes. A few of these share molecular target sites with some synthetic herbicides, but many microbial toxins have unique target sites with potential for exploitation by the herbicide industry. Compounds from both non-pathogenic and [...] Read more.
Some of the most potent phytotoxins are synthesized by microbes. A few of these share molecular target sites with some synthetic herbicides, but many microbial toxins have unique target sites with potential for exploitation by the herbicide industry. Compounds from both non-pathogenic and pathogenic microbes are discussed. Microbial phytotoxins with modes of action the same as those of commercial herbicides and those with novel modes of action of action are covered. Examples of the compounds discussed are tentoxin, AAL-toxin, auscaulitoxin aglycone, hydantocidin, thaxtomin, and tabtoxin. Full article
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