Epirodin, a polyene antibiotic from the mold Epicoccum nigrum.

Ikawa, Miyoshi; McGratten, C J; Burge, William R.; Iannitelli, R C; Uebel, J. J.; Noguchi, Tamao

doi:10.7164/antibiotics.31.159

Cited by 24 publications

(19 citation statements)

References 11 publications

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“…Some antimicrobial compounds produced by E. nigrum have been characterized, such as epicorazines A–B [64], epirodines A–B [65], flavipin [66], epicoccines A–D [67], epipiridones and epicocarines [68]. In particular, flavipin and epicorazines A–B have been associated with E. nigrum biocontrol activity against Monilinia spp., Pythium ssp.…”

Section: Resultsmentioning

confidence: 99%

Epicoccum nigrum P16, a Sugarcane Endophyte, Produces Antifungal Compounds and Induces Root Growth

2012

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BackgroundSugarcane is one of the most important crops in Brazil, mainly because of its use in biofuel production. Recent studies have sought to determine the role of sugarcane endophytic microbial diversity in microorganism-plant interactions, and their biotechnological potential. Epicoccum nigrum is an important sugarcane endophytic fungus that has been associated with the biological control of phytopathogens, and the production of secondary metabolites. In spite of several studies carried out to define the better conditions to use E. nigrum in different crops, little is known about the establishment of an endophytic interaction, and its potential effects on plant physiology.Methodology/Principal FindingsWe report an approach based on inoculation followed by re-isolation, molecular monitoring, microscopic analysis, plant growth responses to fungal colonization, and antimicrobial activity tests to study the basic aspects of the E. nigrum endophytic interaction with sugarcane, and the effects of colonization on plant physiology. The results indicate that E. nigrum was capable of increasing the root system biomass and producing compounds that inhibit the in vitro growth of sugarcane pathogens Fusarium verticillioides, Colletotrichum falcatum, Ceratocystis paradoxa, and Xanthomomas albilineans. In addition, E. nigrum preferentially colonizes the sugarcane surface and, occasionally, the endophytic environment.Conclusions/SignificanceOur work demonstrates that E. nigrum has great potential for sugarcane crop application because it is capable of increasing the root system biomass and controlling pathogens. The study of the basic aspects of the interaction of E. nigrum with sugarcane demonstrated the facultative endophytism of E. nigrum and its preference for the phylloplane environment, which should be considered in future studies of biocontrol using this species. In addition, this work contributes to the knowledge of the interaction of this ubiquitous endophyte with the host plant, and also to a better use of microbial endophytes in agriculture.

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Section: Resultsmentioning

confidence: 99%

Epicoccum nigrum P16, a Sugarcane Endophyte, Produces Antifungal Compounds and Induces Root Growth

2012

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“…in peaches and nectarines [7], [8], [9], against Sclerotinia sclerotiorum in sunflowers [10] and against Pythium in cotton [11]. Many studies have focused on the ability of this fungus to produce antimicrobial compounds such as epicorazins A–B [12], epicoccins A–D [13], epicoccarines A–B and epipyridone [14], flavipin [15] and epirodins [16]. The production of novel bioactive chemical compounds including siderophores [17], antioxidants [18], inhibitors of HIV-1 replication [19], [20], inhibitors of leucemic cells [21], inhibitors of protease [22], inhibitors of telomerase [23] and fluorescent compounds with biotechnological applications [24], [25] have also been described in Epicoccum isolates.…”

Section: Introductionmentioning

confidence: 99%

Polyphasic Analysis of Intraspecific Diversity in Epicoccum nigrum Warrants Reclassification into Separate Species

et al. 2011

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Background Epicoccum nigrum Link (syn. E. purpurascens Ehrenb. ex Schlecht) is a saprophytic ascomycete distributed worldwide which colonizes a myriad of substrates. This fungus has been known as a biological control agent for plant pathogens and produces a variety of secondary metabolites with important biological activities as well as biotechnological application. E. nigrum produces darkly pigmented muriform conidia on short conidiophores on sporodochia and is a genotypically and phenotypically highly variable species. Since different isolates identified as E. nigrum have been evaluated as biological control agents and used for biocompound production, it is highly desirable that this species name refers to only one lineage. However, according to morphological and genetic variation, E. nigrum present two genotypes that may comprise more than one species.Methodology/Principal FindingsWe report the application of combined molecular (ITS and β-tubulin gene sequence analysis, PCR-RFLP and AFLP techniques), morphometric, physiological, genetic compatibility and recombination analysis to study the taxonomic relationships within an endophytic population that has been identified as E. nigrum. This combined analysis established two genotypes showing morphological, physiological and genetic divergence as well as genetic incompatibility characterized by colony inhibition, strongly indicating that these genotypes correspond to different species. Genotype 1 corresponds to E. nigrum while genotype 2 represents a new species, referred to in this study as Epicoccum sp.Conclusions/SignificanceThis research contributes to the knowledge of the Epicoccum genus and asserts that the classification of E. nigrum as a single variable species should be reassessed. In fact, based on the polyphasic approach we suggest the occurrence of cryptic species within E. nigrum and also that many of the sequences deposited as E. nigrum in GenBank and culture collection of microbial strains should be reclassified, including the reference strain CBS 161.73 sequenced in this work. In addition, this study provides valuable tools for differentiation of Epicoccum species.

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“…Ikawa et al. () found that, in acid conditions, epirodin had a tendency to form micelles and colloidal dispersions and to become increasingly insoluble. Development of the intracellular red band in slide dual cultures is thought to be the result of these various pH‐dependent effects which occurred within the cells of B. cinerea and in the PDA immediately adjacent to them.…”

Section: Discussionmentioning

confidence: 99%

“…Epirodins A and B (Ikawa et al 1978) were isolated from an agar culture of E. nigrum and were initially called pigments A and B (Burge et al 1976). They are yellow, interconvertible and light labile.…”

Section: Introductionmentioning

confidence: 99%

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Inhibition of Botrytis cinerea by Epirodin: A Secondary Metabolite from New Zealand Isolates of Epicoccum nigrum

Alcock

Elmer

Marsden

et al. 2015

Journal of Phytopathology

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Many isolates of the saprophytic fungus Epicoccum nigrum produce yellow compounds that diffuse readily into culture media. Historically, two such compounds have been identified; flavipin and epirodin both reported to have antimicrobial properties. Preliminary studies on 280 New Zealand isolates of E. nigrum confirmed that all but two produced a yellow, intensely pigmented substance in sufficient amounts to inhibit the germination of Botrytis cinerea conidia. The compound produced by the inhibitory isolates is epirodin, a polyene antibiotic. Five representative E. nigrum isolates were selected for further investigation. Two of these produced relatively large amounts of epirodin and, in a diffusible metabolite assay, reduced germination of B. cinerea conidia by up to 94%. Another isolate produced a trace amount of epirodin and had no effect on the germination of B. cinerea conidia or on germ tube morphology. The two remaining isolates produced intermediate amounts of epirodin and were only moderately inhibitory to the germination of B. cinerea conidia and to germ tube morphology. In slide dual-culture experiments, epirodin appeared to concentrate in conidia and mycelia of B. cinerea. In acid conditions, as on dual-culture slides of E. nigrum and B. cinerea, the yellow-coloured epirodin underwent a hypsochromic shift, changing colour to become red. The relationship between epirodin production and the suppression of Botrytis growth and development was further investigated using necrotic kiwifruit leaf discs. The E. nigrum isolate that produced the greatest amount of epirodin almost completely inhibited the growth and development of B. cinerea on the leaf discs. In contrast, the efficacy of E. nigrum isolates which produced less epirodin ranged from 78% to just 23%. This is the first report of epirodin production by New Zealand isolates of E. nigrum, and we conclude that isolates that produce high concentrations of epirodin may have potential for plant disease control.

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Epirodin, a polyene antibiotic from the mold Epicoccum nigrum.

Cited by 24 publications

References 11 publications

Epicoccum nigrum P16, a Sugarcane Endophyte, Produces Antifungal Compounds and Induces Root Growth

Epicoccum nigrum P16, a Sugarcane Endophyte, Produces Antifungal Compounds and Induces Root Growth

Polyphasic Analysis of Intraspecific Diversity in Epicoccum nigrum Warrants Reclassification into Separate Species

Inhibition of Botrytis cinerea by Epirodin: A Secondary Metabolite from New Zealand Isolates of Epicoccum nigrum

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