Stictic acid

Stictic acid
Names
	Systematic IUPAC name 1,4-Dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-1,3-dihydro-7H-2,6,12-trioxabenzo[5,6]cyclohepta[1,2-e]indene-11-carbaldehyde
Identifiers
CAS Number	549-06-4;
3D model (JSmol)	Interactive image;
ChemSpider	66327;
ECHA InfoCard	100.161.455
PubChem CID	73677;
CompTox Dashboard (EPA)	DTXSID20972053 ;
	InChI InChI=1S/C19H14O9/c1-6-4-9(25-3)8(5-20)15-10(6)17(22)27-14-7(2)13(21)11-12(16(14)26-15)19(24)28-18(11)23/h4-5,19,21,24H,1-3H3 Key: SKCUFZLDTAYNBZ-UHFFFAOYSA-N;
	SMILES O=C1OC(O)C2=C3C(OC(C(C(C)=CC(OC)=C4C=O)=C4O3)=O)=C(C)C(O)=C21;
Properties
Chemical formula	C19H14O9
Molar mass	386.312 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Stictic acid is an aromatic organic compound, a product of secondary metabolism in some species of lichens.^[1]

Stictic acid is the subject of medical research into cancer. Argentinian research showed that stictic acid extracted from Antarctic lichens has an apoptotic effect.^[2] Subsequent cancer research has found that the compound has tumor suppressing effects via action on mutant p53 proteins in cancer cells.^[3]

References

^ Lohézic-Le Dévéhat, Françoise; Tomasi, Sophie; Elix, John A.; Bernard, Aurélie; Rouaud, Isabelle; Uriac, Philippe; Boustie, Joël (2007). "Stictic Acid Derivatives from the Lichen Usnea articulata and Their Antioxidant Activities". Journal of Natural Products. 70 (7): 1218–20. doi:10.1021/np070145k. PMID 17629329.
^ Correché, ER; Enriz, RD; Piovano, M; Garbarino, J; Gómez-Lechón, MJ (2004). "Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens". Alternatives to laboratory animals : ATLA. 32 (6): 605–15. PMID 15757498.
^ Wassman, Christopher D.; Baronio, Roberta; Demir, Özlem; Wallentine, Brad D.; Chen, Chiung-Kuang; Hall, Linda V.; Salehi, Faezeh; Lin, Da-Wei; Chung, Benjamin P.; Wesley Hatfield, G.; Richard Chamberlin, A.; Luecke, Hartmut; Lathrop, Richard H.; Kaiser, Peter; Amaro, Rommie E. (2013). "Computational identification of a transiently open L1/S3 pocket for reactivation of mutant p53". Nature Communications. 4: 1407. doi:10.1038/ncomms2361. PMC 3562459. PMID 23360998.

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[1] Lohézic-Le Dévéhat, Françoise; Tomasi, Sophie; Elix, John A.; Bernard, Aurélie; Rouaud, Isabelle; Uriac, Philippe; Boustie, Joël (2007). "Stictic Acid Derivatives from the Lichen Usnea articulata and Their Antioxidant Activities". Journal of Natural Products. 70 (7): 1218–20. doi:10.1021/np070145k. PMID 17629329.

[2] Correché, ER; Enriz, RD; Piovano, M; Garbarino, J; Gómez-Lechón, MJ (2004). "Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens". Alternatives to laboratory animals : ATLA. 32 (6): 605–15. PMID 15757498.

[3] Wassman, Christopher D.; Baronio, Roberta; Demir, Özlem; Wallentine, Brad D.; Chen, Chiung-Kuang; Hall, Linda V.; Salehi, Faezeh; Lin, Da-Wei; Chung, Benjamin P.; Wesley Hatfield, G.; Richard Chamberlin, A.; Luecke, Hartmut; Lathrop, Richard H.; Kaiser, Peter; Amaro, Rommie E. (2013). "Computational identification of a transiently open L1/S3 pocket for reactivation of mutant p53". Nature Communications. 4: 1407. doi:10.1038/ncomms2361. PMC 3562459. PMID 23360998.

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