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Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids

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Natural Products

Abstract

Ergot alkaloids are secondary metabolites with significantly toxicological and pharmacological relevance and have been identified in different fungi of Ascomycota and several families of higher plants. Lysergic acid amides or peptides produced by the fungus Claviceps purpurea of the family Clavicipitaceae, e.g., ergometrine, ergotamine, or ergotoxine, and their semisynthetic derivatives are widely used in modern medicine for treatment of diverse diseases. Large-scale productions of ergot alkaloids for pharmaceutical applications have been achieved by biotechnological processes including field cultivation of Claviceps purpurea on rye or in submerged cultures. Some members of the fungal family of Trichocomaceae such as Aspergillus fumigatus and Penicillium commune produce clavine-type ergot alkaloids. These substances consist merely of the ergoline ring system as a common structure of most ergot alkaloids and lack an amide or peptidyl moiety in comparison to ergoamides or ergopeptines. Diverse analytical methods were developed for detection and determination of ergot alkaloids as mycotoxins in foods, cereals, and livestock feeds. Significant progress has also been achieved on the molecular biological and biochemical investigations of ergot alkaloid biosynthesis in the last years. The reaction steps from prenylation of tryptophan to formation of the ergoline ring system have been studied in detail.

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Abbreviations

4-DMA-l-abrine:

N-methyl-4-dimethylallyltryptophan

4-l-DMAT:

4-dimethylallyltryptophan

5-HT:

5-hydroxytryptamine

A. fumigatus :

Aspergillus fumigatus

acetyl-CoA:

Acetyl coenzyme A

C. purpurea :

Claviceps purpurea

C. fusiformis :

Claviceps fusiformis

DMAPP:

Dimethylallyl diphosphate

DMATS:

Dimethylallyl tryptophan synthase

E. coli :

Escherichia coli

EA:

Ergot alkaloid

ELISA:

Enzyme-linked immunosorbent assay

GSH:

Reduced glutathione

HPLC:

High performance liquid chromatography

LSD:

Lysergic acid diethylamide

N. lolii :

Neotyphodium lolii

NADH:

Nicotinamide adenine mononucleotide-phosphate

NFκB:

Nuclear factor κB

NRPS:

Nonribosomal peptide synthetase

P. commune :

Penicillium commune

SAM:

S-adenosyl methionine

TLC:

Thin-layer chromatography

TLR 4:

Toll-like receptor 4

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  1. Philipps-Universität Marburg, Institut für Pharmazeutische Biologie und Biotechnologie, Deutschhausstrasse 17A, 35037, Marburg, Germany

    Peter Mai & Dr. Shu-Ming Li

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  1. Peter Mai
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  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Mai, P., Li, SM. (2013). Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_24

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