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
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.162.058
Properties
C20H20N2O3
Molar mass 336.39 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Cyclopiazonic acid (CPA) is a toxic fungal secondary metabolite.[1] Chemically, CPA is related to ergoline alkaloids. 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 SERCA ATPase in 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.