Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2014 Dec 10;6(12):3281-95.
doi: 10.3390/toxins6123281.

Biosynthetic Pathways of Ergot Alkaloids

Affiliations
Free PMC article
Review

Biosynthetic Pathways of Ergot Alkaloids

Nina Gerhards et al. Toxins (Basel). .
Free PMC article

Abstract

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes.

Figures

Figure 1
Figure 1
Chemical structures of ergot alkaloids: (a) ergoline ring (core structure of all ergot alkaloids); (b) core structure of clavines; (c) core structure of ergoamides; and (d) core structure of ergopeptines.
Figure 2
Figure 2
Formation of the ergoline scaffold-biosynthetic pathway.
Figure 3
Figure 3
Postulated reaction mechanism for the formation of chanoclavine-I from 4-DMA-l-abrine via a diene and an epoxide intermediate.
Figure 4
Figure 4
Formation of fumigaclavines in Aspergillus fumigatus and Penicillium commune.
Figure 5
Figure 5
Formation of lysergic acid and ergotamine from agroclavine in C. purpurea.
Figure 6
Figure 6
Formation of ergonovine and ergopeptines in C. purpurea.
Figure 7
Figure 7
Ergot alkaloid gene cluster in C. purpurea (modified after [26]).

Similar articles

See all similar articles

Cited by 18 articles

See all "Cited by" articles

References

    1. Haarmann T., Rolke Y., Giesbert S., Tudzynski P. Ergot: From witchcraft to biotechnology. Mol. Plant Pathol. 2009;10:563–577. doi: 10.1111/j.1364-3703.2009.00548.x. - DOI - PMC - PubMed
    1. Schiff P.L. Ergot and its alkaloids. Am. J. Pharm. Educ. 2006;70:1–10. doi: 10.5688/aj700598. - DOI - PubMed
    1. Jakubczyk D., Cheng J.Z., O’Connor S.E. Biosynthesis of the ergot alkaloids. Nat. Prod. Rep. 2014;31:1328–1338. doi: 10.1039/C4NP00062E. - DOI - PubMed
    1. Wallwey C., Li S.M. Ergot alkaloids: Structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes. Nat. Prod. Rep. 2011;28:496–510. doi: 10.1039/c0np00060d. - DOI - PubMed
    1. Schardl C.L., Panaccione D.G., Tudzynski P. Ergot alkaloids—Biology and molecular biology. Alkaloids Chem. Biol. 2006;63:45–86. - PubMed

Publication types

Feedback