nach oben

Erschienen in:

2017 | OriginalPaper | Buchkapitel

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

verfasst von : Natalia Arroyo-Manzanares, Laura Gámiz-Gracia, Ana M. García-Campaña, José Diana Di Mavungu, Sarah De Saeger

Erschienen in: Fungal Metabolites

Verlag: Springer International Publishing

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

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.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Vorheriges Kapitel Fungal Protease Inhibitors

Nächstes Kapitel Lanostanoids from Fungi as Potential Medicinal Agents

Tudzynski P, Neubauer L (2014) Ergot alkaloids. Chapter 14. In: Martín JF, García-Estrada C, Zeilinger S (eds) Biosynthesis and molecular genetics of fungal secondary metabolites. Springer, London

Krska R, Crews C (2008) Significance, chemistry and determination of ergot alkaloids: a review. Food Addit Contam 25:722–731CrossRef

Wallwey C, Li S-M (2011) Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes. Nat Prod Rep 28:496–510CrossRef

Young CA, Schardl CL, Panaccione DG, Florea S, Takach JE, Charlton ND, Moore N, Webb JS, Jaromczyk J (2015) Genetics, genomics and evolution of ergot alkaloid diversity. Toxins 7:1273–1302CrossRef

EFSA Panel on Contaminants in the Food Chain (CONTAM) (2012) Scientific opinion on ergot alkaloids in food and feed. EFSA J 10:2798 (158 pp.)CrossRef

Klotz JL (2015) Activities and effects of ergot alkaloids on livestock physiology and production. Toxins 7:2801–2821CrossRef

EFSA (2005) Opinion of the scientific panel on contaminants in the food chain on a request from the commission related to ergot as undesirable substance in animal feed. EFSA J 225:1–27

Komarova EL, Tolkachev ON (2001) The chemistry of peptide ergot alkaloids. Part 1. Classification and chemistry of ergot peptides. Pharm Chem J 35:504–513CrossRef

Kumar A, Bhansali RR (2007) Production of ergot alkaloids from Claviceps. In: Ramawat KG (ed) Biotechnology, second edition: secondary metabolites. CRC Press, Boca Raton

10.

Crews C (2015) Analysis of ergot alkaloids. Toxins 7:2024–2050CrossRef

11.

Stoll A (1920) Zur kenntnis der mutterkornalkaloide. Verh Naturf Ges 101:190–191

12.

Buchta M, Cvak L (1999) Ergot alkaloids and other metabolites of the genus Claviceps. In: Kren V, Cvak L (eds) Ergot: the genus Claviceps. Harwood Academic Publishers, London

13.

Flieger M, Wurst M, Shelby R (1997) Ergot alkaloids – sources, structures and analytical methods. Folia Microbiol 42:3–30CrossRef

14.

Mukherjee J, Menge M (2000) Progress and prospects of ergot alkaloid research. Adv Biochem Eng Biotechnol 68:1–20

15.

Bräse S, Gläser F, Kramer CS, Lindner S, Linsenmeier AM, Masters KS, Meister AC, Ruff BM, Zhong S (2013) Ergot alkaloids. Chapter 4. In: The chemistry of mycotoxins. Springer, WienCrossRef

16.

Wallwey C, Li S-M (2012) Production, detection, and purification of clavine-type ergot alkaloids. In: Keller NP, Turner G (eds) Fungal secondary metabolism. Methods and protocols, vol 944, Methods in molecular biology. Humana Press, New York

17.

Powell RG, Flattner RD, Yates SG (1990) Ergobalansine, a new ergot-type peptide alkaloid isolated from Cenchrus echinatus (sandbur grass) infected with Balansia obtecta, and produced in liquid cultures of B. obtecta and Balansia cyperi. J Nat Prod 53:1272–1279CrossRef

18.

Uhlig S, Petersen D (2008) Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses. Toxicon 52:175–185CrossRef

19.

Müller C, Kemmlein S, Klaffke H, Krauthause W, Preiss-Weigert A, Wittkowski R (2009) A basic tool for risk assessment: a new method for the analysis of ergot alkaloids in rye and selected rye products. Mol Nutr Food Res 53:500–507CrossRef

20.

Lehner AF, Craig M, Fannin N, Bush L, Tobin T (2005) Electrospray [+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds. J Mass Spectrom 40:1484–1502CrossRef

21.

Hafner M, Sulyok M, Schuhmacher R, Crews C, Krska R (2008) Stability and epimerisation behaviour of ergot alkaloids in various solvents. World Mycotoxin J 1:67–78CrossRef

22.

Rutschmann J, Stadler PA (1978) Chemical background. In: Berde B, Schild HO (eds) Ergot alkaloids and related compounds. Springer, Berlin

23.

Maulding HV, Zoglio MA (1970) Physical chemistry of ergot alkaloids and derivatives. Ionization constants of several medicinally active bases. J Pharm Sci 59:700–701CrossRef

24.

Scott P (2007) Analysis of ergot alkaloids – a review. Mycotoxin Res 23:113–121CrossRef

25.

Saxton JE (1960) The indole alkaloids. In: Manske RHF (ed) The alkaloids: chemistry and physiology, vol 7. Academic, London

26.

McPhail AT, Sim GA, Frey AJ, Ott H (1966) Fungal metabolites. Part V. X-ray determination of the structure and stereochemistry of new isomers of the ergot alkaloids of the peptide type. J Chem Soc B 377–395

27.

Smith DJ, Shappell NW (2002) Technical note: epimerization of ergopeptine alkaloids in organic and aqueous solvents. J Anim Sci 80:1616–1622CrossRef

28.

Andrae K, Merkel S, Durmaz V, Fackeldey K, Köppen R, Weber M, Koch M (2014) Investigation of the ergopeptide epimerization process. Computation 2:102–111CrossRef

29.

Lauber U, Schnaufer R, Gredziak M, Kiesswetter Y (2005) Analysis of rye grains and rye meals for ergot alkaloids. Mycotoxin Res 21:258–262CrossRef

30.

Ware GM, Price G, Carter L, Eitenmiller RR (2000) Liquid chromatographic preparative method for isolating ergot alkaloids, using a particle-loaded membrane extracting disk. J AOAC Int 83:1395–1399

31.

Schardl CL, Panaccione DG, Tudzynski P (2006) Ergot alkaloids-biology and molecular biology. Alkaloids Chem Biol 63:45–86CrossRef

32.

Panaccione DG (2010) Ergot alkaloids. In: Hofrichter M (ed) The mycota X. Springer, Berlin

33.

Gerhards N, Neubauer L, Tudzynski P, Li S-M (2014) Biosynthetic pathways of ergot alkaloids. Toxins 6:3281–3295CrossRef

34.

Hulvova H, Galuszka P, Frebortova J, Frebort I (2013) Parasitic fungus Claviceps as a source for biotechnological production of ergot alkaloids. Biotechnol Adv 31:79–89CrossRef

35.

Lorenz N, Wilson EV, Machado C, Schardl CL, Tudzynski P (2007) Comparison of ergot alkaloid biosynthesis gene clusters in Claviceps species indicates loss of late pathway steps in evolution of C. fusiformis. Appl Environ Microbiol 73:7185–7191CrossRef

36.

Gao Q, Jin K, Ying SH, Zhang Y, Xiao G, Shang Y, Duan Z, Hu X, Xie XQ, Zhou G, Peng G, Luo Z, Huang W, Wang B, Fang W, Wang S, Zhong Y, Ma LJ, Leger RJS, Zhao GP, Pei Y, Feng MG, Xia Y, Wang C (2011) Genome sequencing and comparative transcriptomics of the model entomopathogenic fungi Metarhizium anisopliae and M. acridum. PLoS Genet 7:1–18CrossRef

37.

Kozlovsky AG, Zhelifonova VP, Antipova TV, Zelenkova NF (2011) Physiological and biochemical characteristics of the genus Penicillium fungi as producers of ergot alkaloids and quinocitrinins. Appl Biochem Microbiol 47:426–430CrossRef

38.

Ge HM, Yu ZG, Zhang J, Wu JH, Tan RX (2009) Bioactive alkaloids from endophytic Aspergillus fumigatus. J Nat Prod 72:753–755CrossRef

39.

Kozlovsky AG, Zhelifonova VP, Antipova TV (2013) Fungi of the genus Penicillium as producers of physiologically active compounds. Appl Biochem Microbiol 49:1–10CrossRef

40.

Wallwey C, Heddergott C, Xie X, Brakhage AA, Li SM (2012) Genome mining reveals the presence of a conserved gene cluster for the biosynthesis of ergot alkaloid precursors in the fungal family Arthrodermataceae. Microbiology 158:1634–1644CrossRef

41.

Jakubczyk D, Cheng JZ, O’Connor SE (2014) Biosynthesis of the ergot alkaloids. Nat Prod Rep 31:1328–1338CrossRef

42.

Beaulieu WT, Panaccione DG, Hazekamp CS, Mckee MC, Ryan KL, Clay K (2013) Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae). J Chem Ecol 39:919–930CrossRef

43.

Markert A, Steffan N, Ploss K, Hellwig S, Steiner U, Drewke C, Li SM, Boland W, Leistner E (2008) Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus. Plant Physiol 147:296–305CrossRef

44.

Schardl CL, Young CA, Pan J, Florea S, Takach JE, Panaccione DG, Farman ML, Webb JS, Jaromczyk J, Charlton ND, Nagabhyru P, Chen L, Shi C, Leuchtmann A (2013) Currencies of mutualisms: sources of alkaloid genes in vertically transmitted epichloae. Toxins 5:1064–1088CrossRef

45.

Scandola M, Games DE, Costa C, Allegri G, Bertazzo A, Curcuruto O, Traldi P (1994) Structural study of alkaloids from Securidaca longipedunculata roots II. Isolation and characterization by supercritical fluid chromatography/mass spectrometry. J Heterocycl Chem 31:219–224CrossRef

46.

Kucht S, Gross J, Hussein Y, Grothe T, Keller U, Basar S, Konig WA, Steiner U, Leistner E (2004) Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides. Planta 219:619–625CrossRef

47.

Schardl CL (2001) Epichloë festucae and related mutualistic symbionts of grasses. Fungal Genet Biol 33:69–82CrossRef

48.

Panaccione DG, Beaulieu WT, Cook D (2014) Bioactive alkaloids in vertically transmitted fungal endophytes. Funct Ecol 28:299–314CrossRef

49.

Lorenz N, Haarmann T, Pazoutová S, Jung M, Tudzynski P (2009) The ergot alkaloid gene cluster: functional analyses and evolutionary aspects. Phytochemistry 70:1822–1932CrossRef

50.

Young JC, Chen ZJ (1982) Variability in the content and composition of alkaloid found in Canadian ergot. III. Triticale and barley. J Environ Sci Health B 17:93–107CrossRef

51.

Mainka S, Dänicke S, Böhme H, Ueberschär K-H, Liebert F (2007) On the alkaloid content of ergot (Claviceps purpurea). Landbauforschung Volkenrode 57:51–59

52.

Appelt M, Ellner FM (2009) Investigations into the occurrence of alkaloids in ergot and single sclerotia from the 2007 and 2008 harvests. Mycotoxin Res 25:95–101CrossRef

53.

Franzmann C, Wachter J, Dittmer N, Humpf HU (2010) Ricinoleic acid as a marker for ergot impurities in rye and rye products. J Agric Food Chem 58:4223–4229CrossRef

54.

Pažoutová S (2002) The evolutionary strategy of Claviceps. In: White F, Bacon CW, Hywel-Jones NL (eds) Clavicipitalean fungi: evolutionary biology, chemistry, biocontrol and cultural impacts. Marcel Dekker, New York

55.

Tudzynski P, Tenberge KB, Oeser B (1995) Claviceps purpurea. In: Kohmoto K, Singh US, Singh RP (eds) Pathogenesis and host specificity in plant diseases. Pergamon Press/Elsevier, Oxford

56.

Molloy JB, Moore CJ, Bruyeres AG, Murray SA, Blaney BJ (2003) Determination of dihydroergosine in sorghum ergot using an immunoassay. J Agric Food Chem 51:3916–3919CrossRef

57.

Krishnamachari KA, Bhat RV (1976) Poisoning by ergoty bajra (pearl millet) in man. Indian J Med Res 64:1624–1628

58.

Banks GT, Mantle PG, Szczyrbak CA (1974) Large-scale production of clavine alkaloids by Claviceps fusiformis. J Gen Microbiol 82:345–361CrossRef

59.

Agurell S, Ramstad E (1965) A new ergot alkaloid from Mexican maize ergot. Acta Pharm Suec 2:231–238

60.

Lee SL, Floss HG, Heinstein P (1976) Purification and properties of dimethylallylpyrophosphate: tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps sp. SD 58. Arch Biochem Biophys 177:84–94CrossRef

61.

Tudzynski P, Correia T, Keller U (2001) Biotechnology and genetics of ergot alkaloids. Appl Microbiol Biotechnol 57:593–605CrossRef

62.

Metzger U, Schall C, Zocher G, Unsöld I, Stec E, Li SM, Heide L, Stehle T (2009) The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria. Proc Natl Acad Sci U S A 106:14309–14314CrossRef

63.

Hassam SB, Floss HG (1981) Biosynthesis of ergot alkaloids. Incorporation of (17R)-[17-³H]- and (17S)-[17-³H] chanoclavine-I into elymoclavine by Claviceps. J Nat Prod 44:756–758CrossRef

64.

Abea M, Ohmomoa S, Ōhashia T, Tabuchia T (1969) Isolation of chanoclavine-(1) and two new interconvertible alkaloids, rugulovasine A and B, from the cultures of Penicillium concavo-rugulosum. Agric Biol Chem 33:469–471CrossRef

65.

Robinson SL, Panaccione DG (2015) Diversification of ergot alkaloids in natural and modified fungi. Toxins 7:201–218CrossRef

66.

Lorenz N, Olšovská J, Šulc M, Tudzynski P (2010) The alkaloid cluster gene ccsA of the ergot fungus Claviceps purpurea encodes the chanoclavine-I-synthase, an FAD-containing oxidoreductase mediating the transformation of N-methyl-dimethylallyltryptophan to chanoclavine-I. Appl Environ Microbiol 76:1822–1830CrossRef

67.

Goetz KE, Coyle CM, Cheng JZ, O’Connor SE, Panaccione DG (2011) Ergot cluster-encoded catalase is required for synthesis of chanoclavine-I in Aspergillus fumigatus. Curr Genet 57:201–211CrossRef

68.

Coyle CM, Cheng JZ, O’Connor SE, Panaccione DG (2010) An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways. Appl Environ Microbiol 76:3898–3903CrossRef

69.

Cheng JZ, Coyle CM, Panaccione DG, O’Connor SE (2010) Controlling a structural branch point in ergot alkaloid biosynthesis. J Am Chem Soc 132:12835–12837CrossRef

70.

Matuschek M, Wallwey C, Wollinsky B, Xie X, Li SM (2012) In vitro conversion of chanoclavine-I aldehyde to the stereoisomers festuclavine and pyroclavine controlled by the second reduction step. RSC Adv 2:3662–3669CrossRef

71.

Xie X, Wallwey C, Matuschek M, Steinbach K, Li SM (2011) Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation. Magn Reson Chem 49:678–681CrossRef

72.

Wallwey C, Matuschek M, Xie X-L, Li S-M (2010) 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. Org Biomol Chem 8:3500–3508CrossRef

73.

Matuschek M, Wallwey C, Xie X, Li SM (2011) New insights into ergot alkaloid biosynthesis in Claviceps purpurea: an agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine. Org Biomol Chem 9:4328–4335CrossRef

74.

Liu X, Wang L, Steffan N, Yin WB, Li SM (2009) Ergot alkaloid biosynthesis in Aspergillus fumigatus: FgaAT catalyses the acetylation of fumigaclavine B. ChemBioChem 10:2325–2328CrossRef

75.

Maier W, Schumann B, Gröger D (1988) Microsomal oxygenases involved in ergoline alkaloid biosynthesis of various Claviceps strains. J Basic Microbiol 28:83–93CrossRef

76.

Haarmann T, Ortel I, Tudzynski P, Keller U (2006) Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways. ChemBioChem 7:645–652CrossRef

77.

Walzel B, Riederer B, Keller U (1997) Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea. Chem Biol 4:223–230CrossRef

78.

Ortel I, Keller U (2009) Combinatorial assembly of simple and complex d-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea. J Biol Chem 284:6650–6660CrossRef

79.

Barrow KD, Mantle PG, Quigley FR (1974) Biosynthesis of dihydroergot alkaloids. Tetrahedron Lett 16:1557–1560CrossRef

80.

Blaney BJ, Maryam R, Murray S-A, Ryley MJ (2003) Alkaloids of the sorghum ergot pathogen (Claviceps africana): assay methods for grain and feed and variation between sclerotia/sphacelia. Aust J Agric Res 54:167–175CrossRef

81.

Stoll A, Hofman A (1965) The ergot alkaloids. In: Manske RHF (ed) The alkaloids: chemistry and physiology, vol 8. Academic, London

82.

Berde B, Stürmer E (1978) Introduction to the pharmacology of ergot alkaloids and related compounds. In: Berde B, Schild HO (eds) Ergot alkaloids and related compounds. Springer, BerlinCrossRef

83.

Stadler PA, Giger R (1984) Ergot alkaloids and their derivatives in medical chemistry and therapy. In: Krosgard-Larson P, Christensen CH, Kofod H (eds) Natural products and drug development. Munksgaard, Copenhagen

84.

Hart C (1999) Forged in St. Anthony’s fire: drugs for migraine. Mod Drug Discovery 2:20–31

85.

Gröger D (1972) Ergot. In: Kadis S, Ciegler A, Ajl SJ (eds) Microbial toxins, volume VIII: fungal toxins. Academic, London

86.

Görnemann T, Jähnichen S, Schurad B, Latté KP, Horowski R, Tack J, Flieger M, Pertz HH (2008) Pharmacological properties of a wide array of ergolines at functional alpha1-adrenoceptor subtypes. Naunyn Schmiedebergs Arch Pharmakol 376:321–330CrossRef

87.

Villalon CM, de Vries P, Rabelo G, Centurion D, Sanchez-Lopez A, Saxena PR (1999) Canine external carotid vasoconstriction to methysergide, ergotamine and dihydroergotamine: role of 5-HT1B/1D receptors and α2-adrenoceptors. Br J Pharmacol 126:585–594CrossRef

88.

Willems EW, Trion M, de Vries P, Heiligers JOC, Villalon CM, Saxena PR (1999) Pharmacological evidence that α1- and α2-adrenoceptors mediate vasoconstriction of carotid arteriovenous anastomoses in anaesthetized pigs. Br J Pharmacol 127:1263–1271CrossRef

89.

Tfelt-Hansen PC, Koehler PJ (2008) History of the use of ergotamine and dihydroergotamine in migraine from 1906 and onward. Cephalalgia 28:877–886CrossRef

90.

de Groot AN, van Dongen PW, Vree TB, Hekster YA, van Roosmalen J (1998) Ergot alkaloids. Current status and review of clinical pharmacology and therapeutic use compared with other oxytocics in obstetrics and gyneacology. Drugs 56:523–535CrossRef

91.

Wadworth AN, Crisp P (1992) Co-dergocrine mesylate: a review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in age-related cognitive decline. Drugs Aging 2:153–173CrossRef

92.

Ninomiya I, Klguchl T (1990) Ergot alkaloids. In: Brossi A (ed) The alkaloids, vol 38. Academic, San Diego

93.

Eich E, Eichberg D, Miiller WEG (1984) Clavines. New antibiotics with cytostatic activity. Biochem Pharmacol 33:523–526CrossRef

94.

Eich E, Becker C, Eichberg D, Maidhof A, Miiller WEG (1986) Clavines as antitumor agents. Part 5. In vitro activity of semisynthetic festuclavines. Pharmazie 41:156–157

95.

Mrusek M, Seo E-J, Greten HJ, Simon M, Efferth T (2015) Identification of cellular and molecular factors determining the response of cancer cells to six ergot alkaloids. Investig New Drugs 33:32–44CrossRef

96.

Fanchamps A (1978) Introduction to the pharmacology of ergot alkaloids and related compounds. In: Berde B, Schild HO (eds) Some compounds with hallucinogenic activity. Springer, BerlinCrossRef

97.

Barrett A, Morgan L, Raggatt PR, Hobbs JR (1976) Bromocriptine in the treatment of advanced breast cancer. Clin Oncol 2:373–377

98.

Thobois S (2006) Proposed dose equivalence for rapid switch between dopamine receptor agonists in Parkinson’s disease: a review of the literature. Clin Ther 28:1–12CrossRef

99.

Moubarak AS, Piper EL, Johnson ZB, Flieger M (1996) HPLC method for detection of ergotamine, ergosine, and ergine after intravenous injection of a single dose. J Agric Food Chem 44:146–148CrossRef

100.

Van Dongen PWJ, de Groot ANJA (1995) History of ergot alkaloids from ergotism to ergometrine. Eur J Obstet Gynecol Reprod Biol 60:109–116CrossRef

101.

Eadie MJ (2003) Convulsive ergotism: epidemics of the serotonin syndrome? Lancet Neurol 2:429–434CrossRef

102.

Handeland K, Vikøren T (2005) Presumptive gangrenous ergotism in free-living moose and a roe deer. J Wildl Dis 41:636–642CrossRef

103.

Mohamed R, Gremaud E, Tabet JC, Guy PA (2006) Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: usefulness of precursor ion scan experiments. Rapid Commun Mass Spectrom 20:2787–2799CrossRef

104.

Kokkonen M, Jestoi M (2010) Determination of ergot alkaloids from grains with UPLC-MS/MS. J Sep Sci 33:2322–2327CrossRef

105.

Floss HG, Cassady JM, Robbers JE (1973) Influence of ergot alkaloids on pituitary prolactin and prolactin-dependent processes. J Pharm Sci 62:699–715CrossRef

106.

Fuller JG (1968) The day of St. Anthony’s fire. Signet, New York

107.

Bhat RV, Roy DN, Tulpule PG (1976) The nature of alkaloids of ergoty pearl millet or bajra and its comparison with alkaloids of ergoty rye and ergoty wheat. Toxicol Appl Pharmacol 36:11–17CrossRef

108.

Demeke T, Kidane Y, Wuhib E (1979) Ergotism – a report on an epidemic, 1977–78. Ethiop Med J 17:107–113

109.

Urga K, Debella A, Medihn YW, Agata N, Bayu A, Zewdie W (2002) Laboratory studies on the outbreak of gangrenous ergotism associated with consumption of contaminated barley in Arsi, Ethiopia. Ethiop J Heal Dev 16:317–323

110.

Bennett JW, Klich M (2003) Mycotoxins. Clin Microbiol Rev 16:497–516CrossRef

111.

Hogg RA (1991) Poisoning of cattle fed ergotised silage. Vet Rec 129:313–314CrossRef

112.

Porter JK (1995) Analysis of endophyte toxins: fescue and other grasses toxic to livestock. J Anim Sci 73:871–880CrossRef

113.

Miles CO, Lane GA, Di Menna ME, Garthwaite I, Piper EL, Ball OJ-P, Latch GCM, Allen JM, Hunt MB, Bush LP, Min FK, Fletcher I, Harris PS (1996) High levels of ergonovine and lysergic acid amide in toxic Achnatherum inebrians accompanying infection by an Acremonium-like endophytic fungus. J Agric Food Chem 44:1285–1290CrossRef

114.

Uhlig S, Vikoren T, Ivanova L, Handeland K (2007) Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach. Rapid Commun Mass Spectrom 21:1651–1660CrossRef

115.

Griffith RW, Grauwiler J, Hodel C, Leist KH, Matter B (1978) Toxicologic considerations. In: Berde B, Schild HO (eds) Ergot alkaloids and related compounds. Springer, Berlin

116.

Korn AK, Gross M, Usleber E, Thom N, Köhler K, Erhardt G (2014) Dietary ergot alkaloids as a possible cause of tail necrosis in rabbits. Mycotoxin Res 30:241–250CrossRef

117.

Mulac D, Humpf H-U (2011) Cytotoxicity and accumulation of ergot alkaloids in human primary cells Dennis. Toxicology 282:112–121CrossRef

118.

Larson BT, Harmon DL, Piper EL, Griffis LM, Bush LP (1999) Alkaloid binding and activation of D2 dopamine receptors in cell culture. J Anim Sci 77:942–947CrossRef

119.

Larson BT, Samford MD, Camden JM, Piper EL, Kerley MS, Paterson JA, Turner JT (1995) Ergovaline binding and activation of D2 dopamine receptors in GH4ZR7 cells. J Anim Sci 73:1396–1400CrossRef

120.

Oda T, Kume T, Izumi Y, Takada-Takatori Y, Niidome T, Akaike A (2008) Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells. Eur J Pharmacol 598:27–31CrossRef

121.

Mulac D, Lepski S, Ebert F, Schwerdtle T, Humpf HU (2013) Cytotoxicity and fluorescence visualization of ergot alkaloids in human cell lines. J Agric Food Chem 61:462–471CrossRef

122.

Zhang X, Nan Z, Li C, Gao K (2014) Cytotoxic effect of ergot alkaloids in Achnatherum inebrians infected by the Neotyphodium gansuense endophyte. J Agric Food Chem 62:7419–7422CrossRef

123.

Strickland JR, Looper ML, Matthews JC, Rosenkrans JF, Flythe MD, Brown KR (2011) Board-invited review: St. Anthony’s fire in livestock: causes, mechanisms, and potential solutions. J Anim Sci 89:1603–1626CrossRef

124.

Porter JK, Thompson FN Jr (1992) Effects of fescue toxicosis on reproduction in livestock. J Anim Sci 70:1594–1603CrossRef

125.

Varga L, Lutterbeck PM, Pryor JS, Wenner R, Erb H (1972) Suppression of puerperal lactation with an ergot alkaloid: a double-blind study. Br Med J 2:743–744CrossRef

126.

Kopinski JS, Blaney BJ, Downing JA, McVeigh JF, Murray SA (2007) Feeding sorghum ergot (Claviceps africana) to sows before farrowing inhibits milk production. Aust Vet J 85:169–176CrossRef

127.

Kopinski JS, Blaney BJ, Murray SA, Downing JA (2008) Effect of feeding sorghum ergot (Claviceps africana) to sows during mid-lactation on plasma prolactin and litter performance. J Anim Physiol Anim Nutr 92:554–561CrossRef

128.

Zeilmaker GH, Carlsen RA (1962) Experimental studies on the effect of ergocornine methanesulphonate on the luteotrophic function of the rat pituitary gland. Acta Endocrinol 41:321–335

129.

Schams D, Reinhardt V, Karg H (1972) Effects of 2-BR-alpha-ergocryptine on plasma prolactin level during parturition and onset of lactation in cows. Experientia 28:697–699CrossRef

130.

Walner BM, Booth NH, Robbins JD, Bacon CW, Porter JK, Kiser TE, Wilson R, Johnson B (1983) Effect of an endophytic fungus isolated from toxic pasture grass on serum prolactin concentrations in the lactating cow. Am J Vet Res 44:1317–1322

131.

Bernard N, Jantzem H, Becker M, Pecriaux C, Bénard-Laribière A, Montastruc JL, Descotes J, Vial T, French Network of Regional Pharmacovigilance Centres (2015) Severe adverse effects of bromocriptine in lactation inhibition: a pharmacovigilance survey. BJOG 122:1244–1251CrossRef

132.

Malysheva S, Larionova D, Diana Di Mavungu J, De Saeger S (2014) Pattern and distribution of ergot alkaloids in cereals and cereal products from European countries. World Mycotoxin J 7:217–230CrossRef

133.

Storm ID, Have Rasmussen P, Strobel BW, Hansen HCB (2008) Ergot alkaloids in rye flour determined by solid-phase cation-exchange and high-pressure liquid chromatography with fluorescence detection. Food Addit Contam 25:338–346CrossRef

134.

Crews C, Anderson WAC, Rees G, Krska R (2009) Ergot alkaloids in some rye-based UK cereal products. Food Addit Contam Part B Surveill 2:79–85CrossRef

135.

Reinhold L, Reinhardt K (2011) Mycotoxins in foods in Lower Saxony (Germany): results of official control analyses performed in 2009. Mycotoxin Res 27:137–143CrossRef

136.

Masloff S (2006) Ergot alkaloids in foods. III. Ergot alkaloids in cereals and cereal products. J Verbr Lebensm 1:153–154CrossRef

137.

Fajardo JE, Dexter JE, Roscoe MM, Nowicki TW (1995) Retention of ergot alkaloids in wheat during processing. Cereal Chem 72:291–298

138.

Bryła M, Szymczyk K, Jędrzejczak R, Roszko M (2015) Application of liquid chromatography/ion trap mass spectrometry technique to determine ergot alkaloids in grain products. Food Technol Biotechnol 53:18–28CrossRef

139.

Lombaert GA, Pellaers P, Roscoe V, Mankotia M, Neil R, Scott PM (2003) Mycotoxins in infant cereal foods from the Canadian retail market. Food Addit Contam 20:494–504CrossRef

140.

Bürk G, Hobel W, Richt A (2006) Ergot alkaloids in cereal products: results from the Bavarian health and food safety authority. Mol Nutr Food Res 50:437–442CrossRef

141.

Schoch C, Schlatter C (1985) Gesundheitsrisiken durch mutterkorn in getreide. Mitt Geb Lebensmittelunters Hyg 76:631–644

142.

European Commission (2012) Commission Recommendation of 15 March 2012 on the monitoring of the presence of ergot alkaloids in feed and food. Off J Eur Union L77:20–21

143.

Fanali S, Flieger M, Steinerova N, Nardi A (1992) Use of cyclodextrins for the enantioselective separation of ergot alkaloids by capillary zone electrophoresis. Electrophoresis 13:39–43CrossRef

144.

Aboul-Enein HY, Bakr SA (1997) Simultaneous determination of caffeine and ergotamine in pharmaceutical dosage formulation by capillary electrophoresis. J Liq Chromatogr Relat Technol 20:47–55CrossRef

145.

Ma Y, Meyer KG, Afzal D, Agena EA (1993) Isolation and quantification of ergovaline from Festuca arundinacea (tall fescue) infected with the fungus Acremonium coenophialum by high-performance capillary electrophoresis. J Chromatogr A 652:535–538CrossRef

146.

Frach K, Blaschke G (1998) Separation of ergot alkaloids and their epimers and determination in sclerotia by capillary electrophoresis. J Chromatogr A 808:247–252CrossRef

147.

Kvasnicka F, Bíba B, Cvak L (2005) Capillary zone electrophoresis separation of enantiomers of lisuride. J Chromatogr A 1066:255–258CrossRef

148.

Himmelsbach M, Ferdig M, Rohrer T (2014) Analysis of paspalic acid, lysergic acid, and iso-lysergic acid by capillary zone electrophoresis with UV- and quadrupole time-of-flight mass spectrometric detection. Electrophoresis 35:1329–1333CrossRef

149.

Felici E, Wang CC, Fernández LP, Gomez MR (2015) Simultaneous separation of ergot alkaloids by capillary electrophoresis after cloud point extraction from cereal samples. Electrophoresis 36:341–347CrossRef

150.

Müller C, Klaffke HS, Krauthause W, Wittkowski R (2006) Determination of ergot alkaloids in rye and rye flour. Mycotoxin Res 22:197–200CrossRef

151.

Köppen R, Rasenko T, Merkel S, Mönch B, Koch B (2013) Novel solid-phase extraction for epimer-specific quantitation of ergot alkaloids in rye flour and wheat germ oil. J Agric Food Chem 61:10699–10707CrossRef

152.

Ruhland M, Tischler J (2008) Determination of ergot alkaloids in feed by HPLC. Mycotoxin Res 24:73–79CrossRef

153.

Walker K, Duringer J, Craig AM (2015) Determination of the ergot alkaloid ergovaline in tall fescue seed and straw using a QuEChERS extraction method with high-performance liquid chromatography − fluorescence detection. J Agric Food Chem 63:4236–4242CrossRef

154.

Nakamichi T, Yawata A, Hojo H, Kagaya H, Kobayashi S, Chikuma T (2012) Monitoring of methylergometrine in human breast milk by solid-phase extraction and high-performance liquid chromatography with fluorimetric detection. Pharmazie 67:482–484

155.

Diana Di Mavungu J, Malysheva SV, Sanders M, Larionova D, Robbens J, Dubruel P, Van Peteghem C, De Saeger S (2012) Development and validation of a new LC–MS/MS method for the simultaneous determination of six major ergot alkaloids and their corresponding epimers. Application to some food and feed commodities. Food Chem 135:292–303CrossRef

156.

Malysheva SV, Diana Di Mavungu J, Schoeters E, Larionova DA, Goryacheva IY, De Saeger S (2013) Rapid and sensitive LC-MS/MS determination of ergot alkaloids in buffered solutions: application to in vitro testing of a clay-based mycotoxin binder. World Mycotoxin J 6:105–115CrossRef

157.

Lenain P, Diana Di Mavungu J, Dubruel P, Robbens J, De Saeger S (2012) Development of suspension polymerized molecularly imprinted beads with metergoline as template and application in a solid-phase extraction procedure toward ergot alkaloids. Anal Chem 84:10411–10418CrossRef

158.

Najafabadi AS, Mofid MR, Mohammadi R, Moghim S (2010) Quantification of ergovaline using HPLC and mass spectrometry in Iranian Neotyphodium infected tall fescue. Res Pharm Sci 5:135–143

159.

Jarmusch AK, Musso AM, Shymanovich T, Jarmusch SA, Weavil MJ, Lovin ME, Ehrmann BM, Saari S, Nichols DE, Faeth SH, Cech NB (2016) Comparison of electrospray ionization and atmospheric pressure photoionization liquid chromatography mass spectrometry methods for analysis of ergot alkaloids from endophyte-infected sleepygrass (Achnatherum robustum). J Pharm Biomed Anal 117:11–17CrossRef

160.

Malysheva SV, Diana Di Mavungu J, Goryacheva IY, De Saeger S (2013) A systematic assessment of the variability of matrix effects in LC-MS/MS analysis of ergot alkaloids in cereals and evaluation of method robustness. Anal Bioanal Chem 405:5595–5604CrossRef

161.

Martos PA, Thompson W, Diaz GJ (2010) Multiresidue mycotoxin analysis in wheat, barley, oats, rye and maize grain by high- performance liquid chromatography-tandem mass spectrometry. World Mycotoxin J 3:205–223CrossRef

162.

Liao C-D, Wong JW, Zhang K, Hayward DG, Lee NS, Trucksess MW (2013) Multi-mycotoxin analysis of finished grain and nut products using high-performance liquid chromatography − triple-quadrupole mass spectrometry. J Agric Food Chem 61:4771–4782CrossRef

163.

Ezekiel CN, Bandyopadhyay R, Sulyok M, Warth B, Krska R (2012) Fungal and bacterial metabolites in commercial poultry feed from Nigeria. Food Addit Contam 29:1288–1299CrossRef

164.

Zachariasova M, Dzuman Z, Veprikova Z, Hajkova K, Jiru M, Vaclavikova M, Zachariasova A, Pospichalova M, Florian M, Hajslova J (2014) Occurrence of multiple mycotoxins in European feeding stuffs, assessment of dietary intake by farm animals. Anim Feed Sci Technol 193:124–140CrossRef

165.

Malachová A, Sulyok M, Beltrán E, Berthiller F, Krska R (2014) Optimization and validation of a quantitative liquid chromatography–tandem mass spectrometric method covering 295 bacterial and fungal metabolites including all regulated mycotoxins in four model food matrices. J Chromatogr A 1362:145–156CrossRef

166.

Sulyok M, Krska R, Schuhmacher R (2010) Application of an LC–MS/MS based multi-mycotoxin method for the semi-quantitative determination of mycotoxins occurring in different types of food infected by moulds. Food Chem 119:408–416CrossRef

167.

Uhlig S, Eriksen GS, Hofgaard IS, Krska R, Beltrán E, Sulyok M (2013) Faces of a changing climate: semi-quantitative multi-mycotoxin analysis of grain grown in exceptional climatic conditions in Norway. Toxins 5:1682–1697CrossRef

168.

Straumfors A, Uhlig S, Eriksen GS, Heldal KK, Eduard W, Krska R, Sulyok M (2015) Mycotoxins and other fungal metabolites in grain dust from Norwegian grain elevators and compound feed mills. World Mycotoxin J 8:361–373CrossRef

169.

Malachova A, Dzuman Z, Veprikova Z, Vaclavikova M, Zachariasova M, Hajslova J (2011) Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market. J Agric Food Chem 59:12990–12997CrossRef

170.

Arroyo-Manzanares N, Malysheva SV, Bussche JV, Vanhaecke L, Diana Di Mavungu J, De Saeger S (2014) Holistic approach based on high resolution and multiple stage mass spectrometry to investigate ergot alkaloids in cereals. Talanta 118:359–367CrossRef

171.

Arroyo-Manzanares N, Diana Di Mavungu J, Uka V, Gámiz-Gracia L, García-Campaña AM, De Saeger S (2015) An integrated targeted and untargeted approach for the analysis of ergot alkaloids in cereals using UHPLC – hybrid quadrupole time-of-flight mass spectrometry. World Mycotoxin J. doi:10.3920/WMJ2015.1900

172.

Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW (2014) Identification of legal highs – ergot alkaloid patterns in two Argyreia nervosa products. Forensic Sci Int 242:62–71CrossRef

173.

Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW (2015) Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Forensic Sci Int 249:281–293CrossRef

174.

Shelby RA, Kelley VC (1990) An immunoassay for ergotamine and related alkaloids. J Agric Food Chem 38:1130–1134CrossRef

175.

Schnitzius JM, Hill NS, Thompson CS, Craig AM (2001) Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay. J Vet Diagn Investig 13:230–237CrossRef

176.

Shelby RA, Kelley VC (1991) Detection of ergot alkaloids in tall fescue by competitive immunoassay with a monoclonal antibody. Food Agric Immunol 3:169–177CrossRef

177.

Tunali B, Shelby RA, Morgan-Jones G, Kodan M (2000) Endophytic fungi and ergot alkaloids in native Turkish grasses. Phytoparasitica 28:375–377CrossRef

178.

Ayers AW, Hill NS, Rottinghaus GE, Stuedemann JA, Thompson FN, Purinton PT, Seman DH, Dawe DL, Parks AH, Ensley D (2009) Ruminal metabolism and transport of tall fescue ergot alkaloids. Crop Sci 49:2309–2316CrossRef

179.

Roberts CA, Kallenbach RL, Hill NS, Rottinghaus GE, Evans TJ (2009) Ergot alkaloid concentrations in tall fescue hay during production and storage. Crop Sci 49:1496–1502CrossRef

180.

Hopkins AA, Young CA, Panaccione DG, Simpson WR, Mittal S, Bouton JH (2010) Agronomic performance and lamb health among several tall fescue novel endophyte combinations in the South-Central USA. Crop Sci 50:1552–1561CrossRef

181.

Wiegand R, Klette KL, Stout PR, Gehlhausen JM (2002) Comparison of EMIT II, CEDIA, and DPC RIA assays for the detection of lysergic acid diethylamide in forensic urine samples. J Anal Toxicol 26:519–523CrossRef

182.

Saitman A, Park H-D, Fitzgerald RL (2014) False-positive interferences of common urine drug screen immunoassays. J Anal Toxicol 38:387–396CrossRef

183.

Agurell S, Ohlsson A (1971) Gas chromatography of ergot alkaloids. J Chromatogr 61:339–342CrossRef

184.

Barrow KD, Quigley FR (1975) Ergot alkaloids II. Determination of agroclavine by gas–liquid chromatography. J Chromatogr 105:393–395CrossRef

185.

Jegorov A (1999) Analytical chemistry of ergot alkaloids. In: Kren V, Cvak L (eds) Ergot: the genus Claviceps. Harwood Academic Publishers, London

186.

Scott PM (1993) Gas chromatography of mycotoxins. In: Betina V (ed) Chromatography of mycotoxins – techniques and applications. Elsevier, Amsterdam

187.

Bukowski N, Eaton AN (1993) The confirmation and quantitation of LSD in urine using gas-chromatography mass-spectrometry. Rapid Commun Mass Spectrom 7:106–108CrossRef

188.

Musshoff F, Daldrup T (1997) Gas chromatographic mass spectrometric determination of lysergic acid diethylamide (LSD) in serum samples. Forensic Sci Int 88:133–140CrossRef

189.

Nakahara Y, Kikura R, Takahashi K, Foltz RL, Mieczkowski T (1996) Detection of LSD and metabolite in rat hair and human hair. J Anal Toxicol 20:323–329CrossRef

190.

Nelson CC, Foltz RL (1992) Determination of lysergic-acid diethylamide (LSD), iso-LSD, and N-demethyl-LSD in body-fluids by gas-chromatography tandem mass-spectrometry. Anal Chem 64:1578–1585CrossRef

191.

Klug C, Baltes W, Kronert W, Weber R (1988) A method for the determination of ergot alkaloids in food. Z Lebensm Unters Forsch 186:108–113CrossRef

192.

Kozlovsky AG, Zhelifonova VP, Antipova TV, Baskunov BP, Ivanushkina NE, Ozerskaya SM (2014) Exo-metabolites of mycelial fungi isolated in production premises of cheese-making and meat-processing plants. Food Addit Contam Part A 3:300–306CrossRef

193.

Berry AJ, Games DE, Perkins JR (1986) Supercritical fluid chromatographic and supercritical fluid-mass spectrometric studies of some polar compounds. J Chromatogr 363:147–158CrossRef

194.

Stahl M, Jakob A, von Brocke A, Nicholson G, Bayer E (2002) Comparison of different setups for one- and two-dimensional capillary high-performance liquid chromatography and pressurized capillary electrochromatography coupled on-line with mass spectrometry. Electrophoresis 23:2949–2962CrossRef

195.

Roberts CA, Benedict HR, Hill NS, Kallenbach RL, Rottinghaus GE (2005) Determination of ergot alkaloid content in tall fescue by near- infrared spectroscopy. Crop Sci 45:778–783CrossRef

196.

Vermeulen P, Pierna JAF, van Egmond HP, Zegers J, Dardenne P, Baeten V (2013) Validation and transferability study of a method based on near-infrared hyperspectral imaging for the detection and quantification of ergot bodies in cereals. Anal Bioanal Chem 405:7765–7772CrossRef

Titel: Ergot Alkaloids: Chemistry, Biosynthesis, Bioactivity, and Methods of Analysis
verfasst von: Natalia Arroyo-Manzanares
Laura Gámiz-Gracia
Ana M. García-Campaña
José Diana Di Mavungu
Sarah De Saeger
Verlag: Springer International Publishing
Buch: Fungal Metabolites
Print ISBN: 978-3-319-25000-7

Electronic ISBN: 978-3-319-25001-4

Copyright-Jahr: 2017
DOI: https://doi.org/10.1007/978-3-319-25001-4_1