Purpurogallin

Purpurogallin is an orange-red, crystalline compound, and the aglycone of several glycosides from nutgalls and oak barks.[1] It can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase.[2] It potently and specifically inhibits TLR1/TLR2 activation pathway.[3]

Purpurogallin
Names
Preferred IUPAC name
1,7,8,9-Tetrahydroxy-2H-benzo[7]annulen-2-one
Other names
Purpurogalline
2,3,4,6-Tetrahydroxybenzocyclohepten-5-one
PPG
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.478
KEGG
MeSH C026133
UNII
  • InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14) N
    Key: WDGFFVCWBZVLCE-UHFFFAOYSA-N N
  • C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O
Properties
C11H8O5
Molar mass 220.180 g·mol−1
Appearance Red crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

References
  1. Wu, Tai-Wing; Zeng, Ling-Hua; Wu, Jun; Fung, Kwok-Pui; Weisel, Richard D; Hempel, Andrew; Camerman, Norman (1996). "Molecular structure and antioxidant specificity of purpurogallin in three types of human cardiovascular cells". Biochemical Pharmacology. 52 (7): 1073–80. doi:10.1016/0006-2952(96)00447-9. PMID 8831727.
  2. Lambert, Joshua D; Chen, Dapeng; Wang, Ching Y; Ai, Ni; Sang, Shengmin; Ho, Chi-Tang; Welsh, William J; Yang, Chung S (2005). "Benzotropolone inhibitors of estradiol methylation: Kinetics and in silico modeling studies". Bioorganic & Medicinal Chemistry. 13 (7): 2501–7. doi:10.1016/j.bmc.2005.01.037. PMID 15755652.
  3. Cheng, Kui; Wang, Xiaohui; Zhang, Shuting; Yin, Hang (2012). "Discovery of Small-Molecule Inhibitors of the TLR1/TLR2 Complex". Angewandte Chemie International Edition. 51 (49): 12246–9. doi:10.1002/anie.201204910. PMC 3510333. PMID 22969053.


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