Purpurogallin

Purpurogallin is an aglycone natural product. It is an orange-red solid that is soluble in polar organic solvents but not in water. Its glycoside (ether-linked to sugar), called dryophantin, is found in nutgalls and oak barks. Purpurogallin can be prepared by oxidation of pyrogallol with sodium periodate.[1]

Purpurogallin
Chemical structure of 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 checkY☒N ?)
Infobox references

Medicinal aspects

Purpurogallin is bioactive[2] It can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase.[3] It potently and specifically inhibits TLR1/TLR2 activation pathway.[4]

References
  1. Kelly-Hunt, Alexandra E.; Mehan, Aman; Brooks, Sarah; Leanca, Miron A.; McKay, Jack E. D.; Mahamed, Nashad; Lambert, Daniel; Dempster, Nicola M.; Allen, Robert J.; Evans, Andrew R.; Sarker, Satyajit D.; Nahar, Lutfun; Sharples, George P.; Drew, Michael G. B.; Fielding, Alistair J.; Ismail, Fyaz M. D. (2022). "Synthesis and Analytical Characterization of Purpurogallin: A Pharmacologically Active Constituent of Oak Galls" (PDF). Journal of Chemical Education. 99 (2): 983–993. Bibcode:2022JChEd..99..983K. doi:10.1021/acs.jchemed.1c00699. S2CID 245366264.
  2. 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.
  3. 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.
  4. 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.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.