Cyclopiazonic acid

ID 2: 71

Toxin: y

Trivial name:

9H-​Pyrrolo[1′,​2′:2,​3]​isoindolo[4,​5,​6-​cd]​indol-​9-​one, 10-​acetyl-​2,​6,​6a,​7,​11a,​11b-​hexahydro-​11-​hydroxy-​7,​7-​dimethyl-​, (6aα,​11aβ,​11bα)​- (8CI); Cyclopiazonic acid; NSC 117181; α-​Cyclopiazonic acid

Systematic name:

9H-Pyrrolo[1′,2′:2,3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-rel-

Molecular formulae: 

C₂₀H₂₀N₂O₃

Molecular weight: 336.39

Chemical abstract number: 18172-33-3

Chemical type: Alkaloid

Literature reference:

• Production of alkaloids and related substances by fungi. XI. Isolation of cyclopiazonic imine, and bis(secodehydrocyclopiazonic acid) from the cultures of Aspergillus versicolor. Ohmomo, Sadahiro; Sugita, Masanori; Abe, Matazo. Nippon Nogei Kagaku Kaishi (1973), 47(1), 57-63.
  Production of cyclopiazonic acid by Aspergillus flavus Link. Luk, K. C.; Kobbe, B.; Townsend, J. M. Applied and Environmental Microbiology (1977), 33(1), 211-12.
  Mycotoxins of Aspergillus oryzae strains used in the food industry as starters and enzyme producing molds. Orth, R. Annales de la Nutrition et de l’Alimentation (1977), 31(4-5-6), 617-24.
  Production of cyclopiazonic acid by Aspergillus tamarii Kita. Dorner J W, Applied and environmental microbiology (1983), 46(6), 1435-7.
  Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati.Med Mycol.Larsen TO, Smedsgaard J, Nielsen KF, Hansen MA, Samson RA, Frisvad JC. 2007 May;45(3):225-32.

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/54682463
• http://aem.asm.org/content/33/1/211
• http://aem.asm.org/content/46/6/1435
• http://www.tandfonline.com/doi/abs/10.1080/13693780601185939

Aspergillus Species known to produce this metabolite:

• /species/a-versicolor
• /species/a-flavus
• /species/a-oryzae
• /species/a-tamarii

Toxicity:

Tremorgenic toxin. Causes degenerative changes in the liver, kidney and other organs. Intraperitoneal LD50 in the rat 2.3 mg/kg body-weight and oral LD50 of the sodium salt of cyclopiazonic acid is reported to be 19 mg/kg body-weight.

Date uploaded: 2007-09-25 14:42:26

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Mycotoxin & Metabolites

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Aspergillus species produce a large number of secondary metabolites, sometimes referred to as extrolites. We attempt to list them all here and we also collect published papers.

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