Cyclopiazonic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Cyclopiazonic acid
Cyclopiazonic acid.svg
Names
IUPAC name
(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Identifiers
18172-33-3 N
ChEBI CHEBI:22450 YesY
ChEMBL ChEMBL480627 YesY
ChemSpider 21106432 YesY
Jmol-3D images Image
PubChem 65261
Properties
C20H20N2O3
Molar mass 336.38 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Cyclopiazonic acid (CPA) is a toxic fungal secondary metabolite.[1] Chemically, it is an indole tetramic acid. CPA was originally isolated from Penicillium cyclopium and subsequently from other fungi including Penicillium griseofulvum, Penicillium camemberti, Penicillium commune, Aspergillus flavus, and Aspergillus versicolor. CPA only appears to be toxic in high concentrations. Biologically, CPA is a specific inhibitor of Ca2+-ATPase in the intracellular Ca2+ storage sites.[2]

References[edit]

  1. ^ Holzapfel, C. W. (1968). "The isolation and structure of cyclopiazonic acid, a toxic metabolite of Penicillium cyclopium Westling". Tetrahedron 24 (5): 2101–2119. doi:10.1016/0040-4020(68)88113-X. PMID 5636916. 
  2. ^ Sosa, M. J.; Córdoba, J. J.; Díaz, C; Rodríguez, M; Bermúdez, E; Asensio, M. A.; Núñez, F (2002). "Production of cyclopiazonic acid by Penicillium commune isolated from dry-cured ham on a meat extract-based substrate". Journal of food protection 65 (6): 988–92. PMID 12092733.  edit