Isolation and Structure of Harzianum A: A New Trichothecene from Trichoderma harzianum

Corley, David G.; Miller-Wideman, Margaret; Durley, Richard C.

doi:10.1021/np50105a019

Cited by 81 publications

(55 citation statements)

References 8 publications

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“…HPLC analysis of culture supernatants of the T. arundinaceum Ta37 strain resolved three main peaks at 21.1, 22.9, and 39.0 min. The antifungal activity of HA had been previously reported (14), and our bioassay confirmed this. K. marxianus was sensitive only to the fractions collected around the 22.9-min peak.…”

Section: Resultssupporting

confidence: 89%

Identification of Loci and Functional Characterization of Trichothecene Biosynthesis Genes in Filamentous Fungi of the Genus Trichoderma

Cardoza

Malmierca

Hermosa

et al. 2011

Appl Environ Microbiol

129

196

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Trichothecenes are mycotoxins produced by Trichoderma, Fusarium, and at least four other genera in the fungal order Hypocreales. Fusarium has a trichothecene biosynthetic gene (TRI) cluster that encodes transport and regulatory proteins as well as most enzymes required for the formation of the mycotoxins. However, little is known about trichothecene biosynthesis in the other genera. Here, we identify and characterize TRI gene orthologues (tri) in Trichoderma arundinaceum and Trichoderma brevicompactum. Our results indicate that both Trichoderma species have a tri cluster that consists of orthologues of seven genes present in the Fusarium TRI cluster. Organization of genes in the cluster is the same in the two Trichoderma species but differs from the organization in Fusarium. Sequence and functional analysis revealed that the gene (tri5) responsible for the first committed step in trichothecene biosynthesis is located outside the cluster in both Trichoderma species rather than inside the cluster as it is in Fusarium. Heterologous expression analysis revealed that two T. arundinaceum cluster genes (tri4 and tri11) differ in function from their Fusarium orthologues. The Tatri4-encoded enzyme catalyzes only three of the four oxygenation reactions catalyzed by the orthologous enzyme in Fusarium. The Tatri11-encoded enzyme catalyzes a completely different reaction (trichothecene C-4 hydroxylation) than the Fusarium orthologue (trichothecene C-15 hydroxylation). The results of this study indicate that although some characteristics of the tri/TRI cluster have been conserved during evolution of Trichoderma and Fusarium, the cluster has undergone marked changes, including gene loss and/or gain, gene rearrangement, and divergence of gene function.Trichothecenes are a group of over 200 sesquiterpenoidderived secondary metabolites that vary by the pattern of oxygenations and esterifications of a core tricyclic structure with an epoxide function. These metabolites are produced by species in at least six genera of the fungal order Hypocreales (class Sordariomycetes): Fusarium, Myrothecium, Spicellum, Stachybotrys, Trichoderma, and Trichothecium. Trichothecenes are considered mycotoxins because they are often found as contaminants in food and animal feed and they can induce vomiting, alimentary hemorrhaging, and dermatitis in humans and livestock. These symptoms most likely result from the ability of trichothecenes to inhibit protein synthesis (40) and/or to induce apoptosis in eukaryotic cells (45). Trichothecenes also can act as immunosuppressors (51) and neurotoxins (36). Trichothecenes are phytotoxic (17). Previously (56), we observed that overproduction of trichodermin in Trichoderma brevicompactum reduced tomato seed germination and plant growth while increasing the size of the lesions produced when the pathogen was artificially inoculated on tomato plants previously colonized by Trichoderma spp.

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Section: Resultssupporting

confidence: 89%

Identification of Loci and Functional Characterization of Trichothecene Biosynthesis Genes in Filamentous Fungi of the Genus Trichoderma

Cardoza

Malmierca

Hermosa

et al. 2011

Appl Environ Microbiol

129

196

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“…It is a potent mycotoxin with an important bearing on human health (McKean et al 2006). In addition, a culture of T. harzianum was found in 1994 to produce harzianum A (102) (Corley et al 1994). This compound showed cytotoxicity to HT1080 and HeLa cell lines with IC 50 values of 0.65 and 5.07 lg/ml, respectively (Lee et al 2005).…”

Section: Trichothecenesmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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Trichoderma species are free-living fungi that are highly interactive in root, soil and foliar environments and have been used successfully in field trials to control many crop pathogens. Structural and biological studies of the metabolites isolated from Trichoderma species are reviewed. This review, encompassing all the literature in this field up to the present and in which 269 references are cited, also includes a detailed study of the biological activity of the metabolites, especially the role of these metabolites in biological control mechanisms. Some aspects of the biosynthesis of these metabolites and related compounds are likewise discussed.

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“…Chaetomium and Trichoderma also have species that produce mycotoxins that are nocivous to human and animal health and cause perilous food losses (Hou et al, 1972;Udagawa et al, 1979;Corley et al, 1994;Pitt and Hocking, 1999;Sautour et al, 2002;Dantigny et al, 2005;Mandeel, 2005). Trichoderma harzianum and Trichoderma viride, for instance, can cause severe losses in mushroom production because, their presence in the mushroom compost or casing layer, cause the emerging mushrooms to be badly spotted and often distorted Annals of Microbiology, 56 (1) 65-69 (2006) Antimicrobial activities of various essential oils against foodborne pathogenic or spoilage moulds (due to the production of chitinases and glucanases).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activities of various essential oils against foodborne pathogenic or spoilage moulds

et al. 2006

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The use of essential oils in the food industry, as natural sanitizing agents, requires the definition of optimal conditions. The aim of the present work was to evaluate some antimicrobial activity parameters as mycelial growth inhibition, minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of six essential oils against Aspergillus niger, Aspergillus terreus, Chaetomium globosum, Penicillium chrysogenum, Penicillium pinophilum, Trichoderma harzianum and Trichoderma viride. The antimicrobial activity of essential oils was monitored by the macrodiluition technique. The mycelial growth inhibition, fungistatic and fungicidal concentrations were recorded for each strain that showed sensitivity to the essential oils. The essential oils of catnip, cinnamon, tea tree and thyme essential oils exhibited a large spectrum antimicrobial activities; those of clary sage and laurel inhibited the mycelial growth in a few fungal strains. The essential oils of cinnamon and thyme had the lowest MIC and MFC values against all the fungi assayed, followed by catnip, tea tree, clary sage and laurel. The use of these natural products rather than, the currently used antifungal chemicals, may be of interest given that: i) essential oils are of natural origin which means they are safer for human health and the environment and ii) there is less chance that the pathogenic microorganisms will develop resistance.

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Isolation and Structure of Harzianum A: A New Trichothecene from Trichoderma harzianum

Cited by 81 publications

References 8 publications

Identification of Loci and Functional Characterization of Trichothecene Biosynthesis Genes in Filamentous Fungi of the Genus Trichoderma

Identification of Loci and Functional Characterization of Trichothecene Biosynthesis Genes in Filamentous Fungi of the Genus Trichoderma

Secondary metabolites from species of the biocontrol agent Trichoderma

Antimicrobial activities of various essential oils against foodborne pathogenic or spoilage moulds

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