Ergochrome, eine ungewöhnlich vollständige gruppe dimerer farbstoffe aus claviceps purpurea

Franck, Burchard; Baumann, Gert; Ohnsorge, U.

doi:10.1016/s0040-4039(00)90148-5

Cited by 26 publications

(22 citation statements)

References 4 publications

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“…The yellow ergochromes are dimers of tetrahydroxanthone units [ 7 ]. Four different xanthone derivatives were described as ergochrome units in C. purpurea and all possible combinations of two of these units occur in nature [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus Claviceps purpurea

Neubauer

Dopstadt

Humpf

et al. 2016

Fungal Biol Biotechnol

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Background Claviceps purpurea is a phytopathogenic fungus infecting a broad range of grasses including economically important cereal crop plants. The infection cycle ends with the formation of the typical purple-black pigmented sclerotia containing the toxic ergot alkaloids. Besides these ergot alkaloids little is known about the secondary metabolism of the fungus. Red anthraquinone derivatives and yellow xanthone dimers (ergochromes) have been isolated from sclerotia and described as ergot pigments, but the corresponding gene cluster has remained unknown. Fungal pigments gain increasing interest for example as environmentally friendly alternatives to existing dyes. Furthermore, several pigments show biological activities and may have some pharmaceutical value.ResultsThis study identified the gene cluster responsible for the synthesis of the ergot pigments. Overexpression of the cluster-specific transcription factor led to activation of the gene cluster and to the production of several known ergot pigments. Knock out of the cluster key enzyme, a nonreducing polyketide synthase, clearly showed that this cluster is responsible for the production of red anthraquinones as well as yellow ergochromes. Furthermore, a tentative biosynthetic pathway for the ergot pigments is proposed. By changing the culture conditions, pigment production was activated in axenic culture so that high concentration of phosphate and low concentration of sucrose induced pigment syntheses.ConclusionsThis is the first functional analysis of a secondary metabolite gene cluster in the ergot fungus besides that for the classical ergot alkaloids. We demonstrated that this gene cluster is responsible for the typical purple-black color of the ergot sclerotia and showed that the red and yellow ergot pigments are products of the same biosynthetic pathway. Activation of the gene cluster in axenic culture opened up new possibilities for biotechnological applications like the dye production or the development of new pharmaceuticals.Electronic supplementary materialThe online version of this article (doi:10.1186/s40694-016-0020-z) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus Claviceps purpurea

Neubauer

Dopstadt

Humpf

et al. 2016

Fungal Biol Biotechnol

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“…The extract prepared from this fungal culture showed good anti-inflammatory and anticancer activity, and we describe here the isolation of the active compound ergoflavin from this endophyte culture. Ergoflavin was originally reported as the major secondary metabolite of Claviceps purpurea, but no pharmacological activity was reported [5]. We describe, for the first time, novel antiinflammatory and anticancer properties of ergoflavin.…”

mentioning

confidence: 85%

Anti‐Inflammatory and Anticancer Activity of Ergoflavin Isolated from an Endophytic Fungus

Deshmukh

Prabhu

Kulkarni-Almeida

et al. 2009

Chemistry & Biodiversity

108

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Biodiversity is a major resource for identification of new molecules with specific therapeutic activities. To identify such an active resource, high throughput screening (HTS) of the extracts prepared from such diversity are examined on specific functional assays. Based on such HTS studies and bioactivity-based fractionation, we have isolated ergoflavin, a pigment from an endophytic fungus, growing on the leaves of an Indian medicinal plant Mimosops elengi (bakul). We report here the isolation, structure elucidation, and biological properties of this compound, which showed good anti-inflammatory and anticancer activities.

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“…The authors also identied the absolute stereochemistry at these centres. 152 Büchi and co-workers reported novel secalonic acid F (88, ergochrome BE) and secalonic acid D (91, ergochrome EE) in 1977, following isolation from the fungus Aspergillus aculeatus. 153 The following year, then-novel secalonic acid G (90) was isolated alongside secalonic acids A and E from Pyrenochaeta terrestris and the structure elucidated by CD and NMR spectroscopy.…”

Section: Ergochromesmentioning

confidence: 99%

Xanthone dimers: a compound family which is both common and privileged

2015

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Covering: up to 2014. Xanthone dimers are a widespread, structurally-diverse family of natural products frequently found in plants, fungi and lichens. They feature an intriguing variety of linkages between the component xanthones (benzannulated chromanones). These synthetically elusive secondary metabolites are of great interest due to their broad array of bioactivities, which has led to the xanthones being designated as 'privileged structures'. We seek herein to give an overview of all reliably-described xanthone dimers, their structures, occurrence, and the bioactivities established to date. The possible biosynthetic pathways leading to members of this family are also discussed in light of our current knowledge.

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Ergochrome, eine ungewöhnlich vollständige gruppe dimerer farbstoffe aus claviceps purpurea

Cited by 26 publications

References 4 publications

Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus Claviceps purpurea

Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus Claviceps purpurea

Anti‐Inflammatory and Anticancer Activity of Ergoflavin Isolated from an Endophytic Fungus

Xanthone dimers: a compound family which is both common and privileged

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