Neurotoxicity of Penicillium crustosum secondary metabolites: Tremorgenic activity of orally administered penitrem A and thomitrem A and E in mice

Toxicon

Volumn 60, Issue 8, 2012, Pages 1428-1435

  Moldes Anaya, Angel ^a,b   Rundberget, Thomas ^c   Fæste, Christiane K ^c   Eriksen, Gunnar S ^c   Bernhoft, Aksel ^c  

^a Unilab Analyse AS FRAM High North Research Center for Climate and the Environment   (Norway)

^b UNIVERSITY OF TROMSØ   (Norway)

^c NORWEGIAN VETERINARY INSTITUTE   (Norway)

Author keywords

Ataxia; Neurological disease; Penitrem A; Thomitrems; Tremor

Indexed keywords

ALKENE; MYCOTOXIN; PENITREM A; THOMITREM A; THOMITREM E; UNCLASSIFIED DRUG;

ABSORPTION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRAIN LEVEL; CONTROLLED STUDY; CONVULSION; DISEASE SEVERITY; DRUG DOSE; FEEDING; GASTROINTESTINAL TRACT; KIDNEY PARENCHYMA; LIVER LEVEL; MALE; METABOLITE; MOUSE; NEUROTOXICITY; NONHUMAN; PENICILLIUM; PENICILLIUM CRUSTOSUM; PRIORITY JOURNAL; RATING SCALE; TISSUE DISTRIBUTION; TOXIN ANALYSIS; TOXIN STRUCTURE; TREMOR; WEIGHT REDUCTION;

ADMINISTRATION, ORAL; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDOLES; MALE; MICE; MICE, INBRED C57BL; MYCOTOXINS; PENICILLIUM; TANDEM MASS SPECTROMETRY; TREMOR;

ANIMALIA; CANIS FAMILIARIS; MUS; PENICILLIUM; PENICILLIUM CRUSTOSUM;

EID: 84868453416     PISSN: 00410101     EISSN: 18793150     Source Type: Journal    
DOI: 10.1016/j.toxicon.2012.10.007     Document Type: Article

References (32)

1. Breton P., Bizot J.C., Buee J., De la Manche I. Brain neurotoxicity of penitrem A: electrophysiological, behavioural and histopathological study. Toxicon 1998, 36:645-655.
2. Brown R.P., Delp M.D., Lindstedt S.L., Rhomberg L.R., Beliles R.P. Physiological parameter values for physiologically based pharmacokinetic models. Toxicol. Ind. Health 1997, 13:407-484.
3. Cavanagh J.B., Holton J.L., Nolan C.C., Ray D.E., Naik J.T., Mantle P.G. The effects of the tremorgenic mycotoxin penitrem A on the rat cerebellum. Vet. Pathol. 1998, 35:53-63.
4. Ciegler A., Vesonder R.F., Cole R.J. Tremorgenic mycotoxins. Mycotoxins and Other Related Food Problems 1976, vol. 149:163-177. Adv. Chem. Ser., Am. Chem. Soc., Washington D.C.
5. Cole R.J., Dorner J.W., Cox R.H., Raymond L.W. Two classes of alkaloid mycotoxins produced by Penicillium crustosum Thom isolated from contaminated beer. J. Agric. Food Chem. 1983, 31:655-657.
6. Cysewski S.J., Baetz A.L., Pier A.C. Penitrem A intoxication in calves: blood chemical and pathologic changes. Am. J. Vet. Res. 1975, 36:53-58.
7. De Jesus A.E., Steyn P.S., Van Heerden F.R., Vleggaar R., Wessels P.L., Hull W.E. Structure and biosynthesis of the penitrems A-F, six novel tremorgenic mycotoxins from Penicillium crustosum. J. Chem. Soc. Chem. Commun. 1981, 289-291.
8. Eriksen G.S., Hultin-Jäderlund K., Moldes-Anaya A., Schönheit J., Bernhoft A., Jæger G., Rundberget T., Skaar I. Poisoning of dogs with tremorgenic Penicillium toxins. Med. Mycol. 2010, 48:188-196.
9. Gallagher R.T., Hawkes A.D. The potent tremorgenic neurotoxins lolitrem B and aflatrem: a comparison of the tremor response in mice. Experientia 1986, 42:823-825.
10. Gatenby W.A., Munday-Finch S.C., Wilkins A.L., Miles C.O. Terpendole M, a novel indole-diterpenoid isolated from Lolium perenne infected with the endophytic fungus Neotyphodium lolii. J. Agric. Food Chem. 1999, 47:1092-1097.
11. Gordon K.E., Masotti R.E., Waddell W.R. Tremorgenic encephalopathy: a role of mycotoxins in the production of CNS disease in humans?. Can. J. Neurol. Sci. 1993, 20:237-239.
12. Hayes A.W., Presley D.B., Neville J.A. Acute toxicity of penitrem A in dogs. Toxicol. Appl. Pharmacol. 1976, 35:311-320.
13. Jortner B.S., Ehrich M., Katherman A.E., Huckle W.R., Carter M.E. Effects of prolongued tremors due to penitrem A in mice. Drug Chem. Toxicol. 1986, 9:101-116.
14. Knaus H.-G., McManus O.B., Lee S.H., Schmalhofer W.A., Garcia-Calvo M., Helms L.M.H., Sanchez M., Giangiacomo K., Reuben J.P., Smith A.B., Kaczorowski G.J., Garcia M.L. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium activated potassium channels. Biochemistry 1994, 33:5819-5828.
15. Kyriakidis N., Waight E.S., Day J.B., Mantle J.B. Novel metabolites from Penicillium crustosum, including penitrem E, a tremorgenic mycotoxin. Appl. Environ. Microbiol. 1981, 42:61-62.
16. Laakso J.A., Gloer J.B., Wicklow D.T., Dowd P.F. Sulpinine A-C and secopenitrem B: new antiinsectan metabolites from the sclerotia of Aspergillus sulphurous. J. Org. Chem. 1992, 57:2066-2071.
17. 14C-penitrem mycotoxins in sheep bile. Res. Vet. Sci. 1987, 43:199-202.
18. Lewis P.R., Donoghue M.B., Hocking A.D., Cook L., Granger L.V. Tremor syndrome associated with fungal toxin: sequelae of food contamination. Med. J. Aust. 2005, 182:582-584.
19. Moldes-Anaya A., Wilkins A.L., Rundberget T., Fæste C.K. In vitro and in vivo hepatic metabolism of the fungal neurotoxin penitrem A. Drug Chem. Toxicol. 2009, 32:26-37.
20. Moldes-Anaya A., Rundberget T., Uhlig S., Rise F., Wilkins A.L. Isolation and structure elucidation of secopenitrem D, an indole alkaloid from Penicillium crustosum Thom. Toxicon 2011, 57:259-265.
21. Moldes-Anaya A., Fonnum F., Eriksen G.S., Rundberget T., Walaas S.I., Wigestrand M.B. In vitro neuropharmacological evaluation of penitrem-induced tremorgenic syndromes: Importance of the GABAergic system. Neurochem. Int. 2011, 59:1074-1081.
22. Naik J.T., Mantle P.G., Sheppard R.N., Waight E.S. Penitremones A-C, Penicillium metabolites containing an oxidised penitrem carbon skeleton giving insight into structure-tremorgenic relationships. J. Chem. Soc. Perkin Trans. I 1995, 1121-1125.
23. Norris P.J., Smith C.C.T., De Belleroche J., Bradford H.F., Mantle P.G., Thomas A.J., Penny R.H.C. Actions of tremorgenic fungal toxins on neurotransmitter release. J. Neurochem. 1980, 34:33-42.
24. Patterson D.S.P., Roberts B.A., Shreeve B.J., McDonald S.M., Hayes A.W. Tremorgenic toxins produced by soil fungi. Appl. Environ. Microbiol. 1979, 37:172-173.
25. Penn J., Biddle J.R., Mantle P.G., Bilton J.N., Sheppard R.N. Pennigritrem, a naturally occurring penitrem A analogue with novel cyclisation in the diterpenoid moiety. J. Chem. Soc. Perkin Trans. I 1992, 23-26.
26. Penny R.H., O'Sullivan B.M., Mantle P.G., Shaw B.I. Clinical studies on tremorgenic mycotoxicoses in sheep. Vet. Rec. 1979, 105:392-393.
27. Rundberget T., Wilkins A.L. Thomitrem A and E, two new indole-alkaloid isoprenoids from Penicillium crustosum Thom. Phytochemistry 2002, 61:979-985.
28. Rundberget T., Wilkins A.L. Determination of Penicillium toxins in food and feeds using liquid chromatography-mass spectrometry. J. Chromatogr. A 2002, 964:189-197.
29. Tiwary A.K., Puschner B., Poppenga R.H. Using roquefortine C as a biomarker for penitrem A intoxication. J. Vet. Diagn. Invest. 2009, 21:237-239.
30. Wilson B.J., Wilson C.H., Hayes A.W. Tremorgenic toxin from Penicillium cyclopium grown on food materials. Nature 1968, 220:77-78.
31. Wyatt R.D., Hamilton P.B., Colwell W.M., Ciegler A. The effect of tremortin A on chickens. Avian Dis. 1972, 16:461-464.
32. Yamaguchi T., Nozawa K., Hosoe T., Nakajima S., Kawai K.-I. Indolediterpenes related to tremorgenic mycotoxins, penitrems, from Penicillium crustosum. Phytochemistry 1993, 32:1177-1181.