Cyclopiazonic acid

Cyclopiazonic acid
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
CAS Number	18172-33-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:22450 ;
ChEMBL	ChEMBL480627 ;
ChemSpider	21106432 ;
ECHA InfoCard	100.162.058
IUPHAR/BPS	5350;
PubChem CID	65261;
	InChI InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1 Key: SZINUGQCTHLQAZ-DQYPLSBCSA-N ; InChI=1/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1 Key: SZINUGQCTHLQAZ-DQYPLSBCBO;
	SMILES CC(=O)C1=C(O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3[nH]cc(c23)[C@@H]45;
Properties
Chemical formula	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).
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	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

↑ 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.
↑ 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.

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