A New Strain of Claviceps purpurea Accumulating Tetracyclic Clavine Alkaloids

Schumann, Brigitte; Erge, D.; Maier, W.; Gröger, D.

doi:10.1055/s-2007-971231

Cited by 16 publications

(3 citation statements)

References 5 publications

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“…15 2 and 3 were isolated from C. purpurea and A. fumigatus, respectively. [16][17][18] 2 differs from 3 in the presence of a double bond between C8 and C9. For the formation of 2 from 1, one reduction and an isomerisation step would be necessary.…”

Section: Introductionmentioning

confidence: 99%

New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine

et al. 2011

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Ergot alkaloids are indole derivatives with diverse structures and biological activities. They are produced by a wide range of fungi with Claviceps purpurea as the most important producer for medical use. Chanoclavine-I aldehyde is proposed as a branch point via festuclavine or pyroclavine to clavine-type alkaloids in Trichocomaceae and via agroclavine to ergoamides and ergopeptines in Clavicipitaceae. Here we report the conversion of chanoclavine-I aldehyde to agroclavine by EasG from Claviceps purpurea, a homologue of the festuclavine synthase FgaFS in Aspergillus fumigatus, in the presence of reduced glutathione and NADPH. EasG comprises 290 amino acids with a molecular mass of about 31.9 kDa. The soluble monomeric His(6)-EasG was purified after overproduction in E. coli by affinity chromatography and used for enzyme assays. The structure of agroclavine was unequivocally elucidated by NMR and MS analyses.

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Section: Introductionmentioning

confidence: 99%

New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine

et al. 2011

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“…The new mutant C. purpurea 59 was obtained by multiple mutagenesis with UV-light. In contrast to the mutant 59 the strain Pepty 695/ch and its other variants were obtained merely by a screening of colonies grown after protoplast regeneration (without other mutagenic interventions) [16]. The mutation was induced in this case probably by the snail gut enzyme used for preparation of protoplasts.…”

Section: Discussionmentioning

confidence: 99%

High-production mutant Claviceps purpurea 59 accumulating secoclavines

Křen

1986

FEMS Microbiology Letters

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A new alkaloid-blocked strain has been derived from the tetracyclic-clavine-producing strain Claviceps purpurea 129/35. This strain, strain 59, was selected by a 3-stage UV-mutation of conidia. It produces up to 6.5 g/1 alkaloids, consisting of chanoclavine-I (40-60%), chanoclavine-I-aldehyde (20-30%), elymoclavine (10-15%) and agroclavine (5-10%). The structure of chanoclavine-I-aldehyde was confirmed by 1H and 13C-nuclear magnetic resonance (NMR)

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“…68,73 Festuclavine (10) has so far only been identified in Aspergillus fumigatus, 73,74 while Penicillium strains produced both festuclavine (10) and its stereoisomer pyroclavine (11). 27,32,70,75,76 Agroclavine is mainly produced by Claviceps strains, [77][78][79][80][81] but also by Penicillium commune. 70 Claviceps hirtella mainly produced clavines, together with ergometrine as a minor (3-8%) component of the total ergot alkaloids.…”

Section: Other Related Structuresmentioning

confidence: 99%

Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes

2011

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Ergot alkaloids are toxins and important pharmaceuticals which are produced biotechnologically on an industrial scale. They have been identiﬁed in two orders of fungi and three families of higher plants. The most important producers are fungi of the genera Claviceps, Penicillium and Aspergillus (all belonging to the Ascomycota). Chemically, ergot alkaloids are characterised by the presence of a tetracyclic ergoline ring, and can be divided into three classes according to their structural features, i.e. amide- or peptide-like amide derivatives of D-lysergic acid and the clavine alkaloids. Signiﬁcant progress has been achieved on the molecular biological and biochemical investigations of ergot alkaloid biosynthesis in the last decade. By gene cloning and genome mining, gene clusters for ergot alkaloid biosynthesis have been identiﬁed in at least 8 different ascomycete species. Functions of most structure genes have been assigned to reaction steps in the biosynthesis of ergot alkaloids by gene inactivation experiments or biochemical characterisation of the overproduced proteins.

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A New Strain of Claviceps purpurea Accumulating Tetracyclic Clavine Alkaloids

Cited by 16 publications

References 5 publications

New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine

New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine

High-production mutant Claviceps purpurea 59 accumulating secoclavines

Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes

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