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Vinokurova, N. G.; Boichenko, L. V.; Arinbasarov, M. U.

doi:10.1023/a:1024576703367

Cited by 14 publications

(2 citation statements)

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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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Section: Other Related Structuresmentioning

confidence: 99%

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

2011

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“…2) or its diastereomer pyroclavine in Aspergillus and Penicillium, which have been isolated from both genera. 1, 11 However, an enzymatic formation of 4 or of pyroclavine in A. fumigatus has not yet been demonstrated by an overproduced and purified enzyme or by crude enzyme extracts from a producer.…”

Section: Introductionmentioning

confidence: 99%

Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3

et al. 2010

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Ergot alkaloids are toxins and important pharmaceuticals which are produced biotechnologically on an industrial scale. A putative gene fgaFS has been identified in the biosynthetic gene cluster of fumigaclavine C, an ergot alkaloid of the clavine-type. The deduced gene product FgaFS comprises 290 amino acids with a molecular mass of about 32.1 kDa. The coding region of fgaFS consisting of three exons was amplified by PCR from a cDNA library of Aspergillus fumigatus, cloned into pQE70 and overexpressed in E. coli. The soluble monomeric His(6)-FgaFS was purified by affinity chromatography and used for enzyme assays. It has been shown that FgaFS is responsible for the conversion of chanoclavine-I aldehyde to festuclavine in the presence of the old yellow enzyme FgaOx3. The structure of festuclavine including the stereochemistry was unequivocally elucidated by NMR and MS analyses. Festuclavine formation was only observed when chanoclavine-I aldehyde was incubated with FgaOx3 and FgaFS simultaneously or as a tandem-reaction with a sequence of FgaOx3 before FgaFS. In the absence of FgaFS, two shunt products were formed and did not serve as substrates for FgaFS reaction.

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Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids

Mai¹,

Li²

2013

Natural Products

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Cited by 14 publications

References 1 publication

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

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

Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3

Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids

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