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Ergot Alkaloids: Chemistry, Biosynthesis, Bioactivity, and Methods of Analysis

  • Reference work entry
  • First Online:
Fungal Metabolites

Part of the book series: Reference Series in Phytochemistry ((RSP))

Abstract

Ergot alkaloids are indole derivatives produced by a wide range of fungi, being considered medically important because of their significant effect on the central nervous system of mammals, due to their structural similarity to neurotransmitters. They are also considered mycotoxins due to the severe toxic effects of ergot-contaminated grains on human and animal health. This chapter summarizes different aspects of ergot alkaloids concerning their chemistry, biosynthesis, and bioactivity, discussing the pharmacological activity as well as some important aspects related to their toxicity, occurrence, and regulations. Finally, an overview of analytical methods for the determination of ergot alkaloids is included, whereby high-performance liquid chromatography coupled to fluorescence or mass spectrometer detection are the most widely used methods, although other techniques such as capillary electrophoresis or immunoassays have also been reported.

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Abbreviations

5-HT:

5-Hydroxytryptamine

AA:

Amino acid

AdoMet:

Adenosylmethionine

APCI:

Atmospheric pressure chemical ionization

APPI:

Atmospheric pressure photoionization

ARfD:

Acute reference dose

BGE:

Background electrolyte

CE:

Capillary electrophoresis

CMC:

Critical micellar concentration

CONTAM Panel:

Panel on Contaminants in the Food Chain

CPE:

Cloud point extraction

CZE:

Capillary zone electrophoresis

DMA:

Dimethylallyl

DMAPP:

Dimethylallyl diphosphate

DMAT:

Dimethylallyltryptophan

DMATS:

Dimethylallyltryptophan synthase

d-SPE:

Dispersive solid phase extraction

EA:

Ergot alkaloid

EC:

European Commission

EFSA:

European Food Safety Authority

ELISA:

Enzyme-linked immunosorbent assay

ESI:

Electrospray ionization

EU:

European Union

FAD:

Flavin adenine dinucleotide

FLD:

Fluorescence detection

GC:

Gas chromatography

HPLC:

High-performance liquid chromatography

HRMS:

High-resolution mass spectrometry

IT:

Ion trap

LC:

Liquid chromatography

LD50 :

Lethal dose 50 %

LLE:

Liquid–liquid extraction

LSA:

Lysergic acid amide

LSD:

Lysergic acid diethylamide

MIP:

Molecularly imprinted polymer

MS/MS:

Tandem mass spectrometry

MS:

Mass spectrometry

MT:

Methyltransferase

NIR:

Near infrared

pCEC:

Pressurized capillary electrochromatography

PSA:

Primary secondary amine

Q-TOF:

Quadrupole time of flight

QuEChERS:

Quick, easy, cheap, effective, rugged, and safe

RIA:

Radioimmunoassay

SCX:

Strong cation exchange

SPE:

solid phase extraction

TDI:

Tolerable daily intake

TLC:

Thin layer chromatography

TOF:

Time of flight

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Acknowledgments

Natalia Arroyo-Manzanares received postdoctoral grant from the University of Granada.

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Authors and Affiliations

  1. Laboratory of Food Analysis, Faculty of Pharmaceutical Sciences, Ghent University, Ottergemsesteenweg 460, 9000, Ghent, Belgium

    Natalia Arroyo-Manzanares, José Diana Di Mavungu & Sarah De Saeger

  2. Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Campus Fuentenueva s/n, E-18071, Granada, Spain

    Natalia Arroyo-Manzanares, Laura Gámiz-Gracia & Ana M. García-Campaña

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  1. Natalia Arroyo-Manzanares
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  2. Laura Gámiz-Gracia
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  3. Ana M. García-Campaña
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  4. José Diana Di Mavungu
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  5. Sarah De Saeger
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Correspondence to Natalia Arroyo-Manzanares .

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  1. Faculty of Pharmaceutical Sciences, University of Bordeaux, Bordeaux, France

    Jean-Michel Mérillon

  2. Botany Department, M.L.Sukhadia University, Udaipur, Rajasthan, India

    Kishan Gopal Ramawat

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Arroyo-Manzanares, N., Gámiz-Gracia, L., García-Campaña, A.M., Diana Di Mavungu, J., De Saeger, S. (2017). Ergot Alkaloids: Chemistry, Biosynthesis, Bioactivity, and Methods of Analysis. In: Mérillon, JM., Ramawat, K. (eds) Fungal Metabolites. Reference Series in Phytochemistry. Springer, Cham. https://doi.org/10.1007/978-3-319-25001-4_1

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