Biosynthesis of ergot alkaloids and related compounds

Floss, Heinz G.

doi:10.1016/0040-4020(76)85047-8

Cited by 196 publications

(122 citation statements)

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“…Fungi derived from two relatively divergent ascomycete orders (Hypocreales and Eurotiales) produce ergot alkaloids. Several fungi in the family Clavicipitaceae (order Hypocreales), including the ergot fungi in the genus Claviceps and certain grass endophytes in the genera Epichloë (including their imperfect relatives in the genus Neotyphodium) and Balansia, produce ergot alkaloids in association with their grass hosts (3,6,7,14,25). The rather distantly related imperfect fungus Aspergillus fumigatus, a common saprophyte and opportunistic human pathogen with close relatives in the order Eurotiales, produces ergot alkaloids in broth culture (4,23) and in association with its airborne conidia (13).…”

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An Ergot Alkaloid Biosynthesis Gene and Clustered Hypothetical Genes from Aspergillus fumigatus

Coyle

Panaccione

2005

Appl Environ Microbiol

108

140

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The ergot alkaloids are a family of indole-derived mycotoxins with a variety of significant biological activities. Aspergillus fumigatus, a common airborne fungus and opportunistic human pathogen, and several fungi in the relatively distant taxon Clavicipitaceae (clavicipitaceous fungi) produce different sets of ergot alkaloids. The ergot alkaloids of these divergent fungi share a four-member ergoline ring but differ in the number, type, and position of the side chains. Several genes required for ergot alkaloid production are known in the clavicipitaceous fungi, and these genes are clustered in the genome of the ergot fungus Claviceps purpurea. We investigated whether the ergot alkaloids of A. fumigatus have a common biosynthetic and genetic origin with those of the clavicipitaceous fungi. A homolog of dmaW, the gene controlling the determinant step in the ergot alkaloid pathway of clavicipitaceous fungi, was identified in the A. fumigatus genome. Knockout of dmaW eliminated all known ergot alkaloids from A. fumigatus, and complementation of the mutation restored ergot alkaloid production. Clustered with dmaW in the A. fumigatus genome are sequences corresponding to five genes previously proposed to encode steps in the ergot alkaloid pathway of C. purpurea, as well as additional sequences whose deduced protein products are consistent with their involvement in the ergot alkaloid pathway. The corresponding genes have similarities in their nucleotide sequences, but the orientations and positions within the cluster of several of these genes differ. The data indicate that the ergot alkaloid biosynthetic capabilities in A. fumigatus and the clavicipitaceous fungi had a common origin.

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confidence: 99%

“…The ergot alkaloids are a complex family of indole-derived mycotoxins with varied and significant biological activities (6,7,14,25). Fungi derived from two relatively divergent ascomycete orders (Hypocreales and Eurotiales) produce ergot alkaloids.…”

mentioning

confidence: 99%

An Ergot Alkaloid Biosynthesis Gene and Clustered Hypothetical Genes from Aspergillus fumigatus

Coyle

Panaccione

2005

Appl Environ Microbiol

108

140

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“…Due to their long biotechnological tradition, with manifold applications in therapy (Tudzynski et al 2001), the physiology and biochemistry of ergopeptine formation have been studied in minute detail (Floss 1976;Socic and Gaberc-Porekar 1992;Gro¨ger and Floss 1998). Nevertheless, an uncomfortable premonition of scar- Figure 11.…”

Section: Ergopeptinesmentioning

confidence: 99%

Endophytes: exploiting biodiversity for the improvement of natural product-based drug discovery

Staniek

Woerdenbag

Kayser

2008

Journal of Plant Interactions

132

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Endophytes, microorganisms that colonize internal tissues of all plant species, create a huge biodiversity with yet unknown novel natural products, presumed to push forward the frontiers of drug discovery. Next to the clinically acknowledged antineoplastic agent, paclitaxel, endophyte research has yielded potential drug lead compounds with antibacterial, antiviral, antioxidant, insulin mimetic, anti-neurodegenerative and immunosuppressant properties. Furthermore, while being implicated in livestock neurotoxicosis, some endophyte-produced alkaloids have been shown to display insecticidal activity. The endophyte-host relationship is postulated to be a 'balanced antagonism'. Moreover, the plausibility of horizontal gene transfer (HGT) hypothesis is taken into account. Knowledge of the genetic background of endophytic natural product biosynthesis is discussed on the basis of loline alkaloids, ergopeptines, lolitrems and maytansinoids. The current dynamic progress in genomics will contribute to a better understanding of endophytic microbes and to further exploiting them as a source of pharmaceutically relevant compounds.

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“…Though the number of natural products possessing a 3,4-fused azepinoindole skeleton was limited, 6,8,[10][11][12][13][14][15][16][17][18] those compounds were attracting great interest as synthetic targets. 19) Therefore, 1 and 2 were the new members of relatively rare class of natural products.…”

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Hyrtinadines C and D, New Azepinoindole-Type Alkaloids from a Marine Sponge <i>Hyrtios</i> sp.

et al. 2016

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Biosynthesis of ergot alkaloids and related compounds

Cited by 196 publications

References 199 publications

An Ergot Alkaloid Biosynthesis Gene and Clustered Hypothetical Genes from Aspergillus fumigatus

An Ergot Alkaloid Biosynthesis Gene and Clustered Hypothetical Genes from Aspergillus fumigatus

Endophytes: exploiting biodiversity for the improvement of natural product-based drug discovery

Hyrtinadines C and D, New Azepinoindole-Type Alkaloids from a Marine Sponge <i>Hyrtios</i> sp.

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