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;
UNII	X9TLY4580Z ;
CompTox Dashboard (EPA)	DTXSID00891798 ;
	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	336.391 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. Ingestion of CPA causes one to be an anorexic, to be dehydrated, to lose weight, to be immobile, and has some sign of spasm when near death. They can be found in molds, corns, peanuts, and other fermented products, such as cheese and sausages.[2]Biologically, CPA is a specific inhibitor of SERCA ATPase in intracellular Ca²⁺ storage sites.[3] CPA inhibits SERCA ATPase by keeping it in one specific confirmation, thus, preventing it from forming another.[4] CPA also binds to SERCA ATPase at the same site as another inhibitor, thapsigargin (TG). In this way, CPA lowers the ability of SERCA ATPase to bind an ATP molecule.[5]

References

Holzapfel, C.W. (January 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.
Bullerman, L.B. (2003). "MYCOTOXINS | Classifications". Encyclopedia of Food Sciences and Nutrition. pp. 4080–4089. doi:10.1016/B0-12-227055-X/00821-X. ISBN 978-0-12-227055-0.
Sosa, María J.; Córdoba, Juan J.; Díaz, Carmen; Rodríguez, Mar; Bermúdez, Elena; Asensio, Miguel A.; Núñez, Félix (June 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): 988–992. doi:10.4315/0362-028X-65.6.988. PMID 12092733.
Soler, Fernando; Plenge-Tellechea, Fernando; Fortea, Isabel; Fernandez-Belda, Francisco (March 1998). "Cyclopiazonic Acid Effect on Ca²⁺-Dependent Conformational States of the Sarcoplasmic Reticulum ATPase. Implication for the Enzyme Turnover". Biochemistry. 37 (12): 4266–4274. doi:10.1021/bi971455c. PMID 9521749.
Ma, Hailun; Zhong, Lilin; Inesi, Giuseppe; Fortea, Isabel; Soler, Fernando; Fernandez-Belda, Francisco (November 1999). "Overlapping Effects of S3 Stalk Segment Mutations on the Affinity of Ca²⁺-ATPase (SERCA) for Thapsigargin and Cyclopiazonic Acid". Biochemistry. 38 (47): 15522–15527. doi:10.1021/bi991523q. PMID 10569935.

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[1] Holzapfel, C.W. (January 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.

[:0-2] Bullerman, L.B. (2003). "MYCOTOXINS | Classifications". Encyclopedia of Food Sciences and Nutrition. pp. 4080–4089. doi:10.1016/B0-12-227055-X/00821-X. ISBN 978-0-12-227055-0.

[3] Sosa, María J.; Córdoba, Juan J.; Díaz, Carmen; Rodríguez, Mar; Bermúdez, Elena; Asensio, Miguel A.; Núñez, Félix (June 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): 988–992. doi:10.4315/0362-028X-65.6.988. PMID 12092733.

[4] Soler, Fernando; Plenge-Tellechea, Fernando; Fortea, Isabel; Fernandez-Belda, Francisco (March 1998). "Cyclopiazonic Acid Effect on Ca²⁺-Dependent Conformational States of the Sarcoplasmic Reticulum ATPase. Implication for the Enzyme Turnover". Biochemistry. 37 (12): 4266–4274. doi:10.1021/bi971455c. PMID 9521749.

[5] Ma, Hailun; Zhong, Lilin; Inesi, Giuseppe; Fortea, Isabel; Soler, Fernando; Fernandez-Belda, Francisco (November 1999). "Overlapping Effects of S3 Stalk Segment Mutations on the Affinity of Ca²⁺-ATPase (SERCA) for Thapsigargin and Cyclopiazonic Acid". Biochemistry. 38 (47): 15522–15527. doi:10.1021/bi991523q. PMID 10569935.