Purpurogallin Explained

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]

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]

Historical work

Purpurogallin, obtained by oxidation of pyrogallol, attracted attention for dyeing. Arthur George Perkin (son of William Henry Perkin, discoverer of the dye mauvine) reported early characterization including the formation of trimethyl ether and the triacetate..[5]

Notes and References

  1. 10.1021/acs.jchemed.1c00699. Synthesis and Analytical Characterization of Purpurogallin: A Pharmacologically Active Constituent of Oak Galls . 2022 . 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. . Journal of Chemical Education . 99 . 2 . 983–993 . 2022JChEd..99..983K . 245366264 .
  2. 10.1016/0006-2952(96)00447-9. 8831727. Molecular structure and antioxidant specificity of purpurogallin in three types of human cardiovascular cells. Biochemical Pharmacology. 52. 7. 1073–80. 1996. Wu. Tai-Wing. Zeng. Ling-Hua. Wu. Jun. Fung. Kwok-Pui. Weisel. Richard D. Hempel. Andrew. Camerman. Norman.
  3. 10.1016/j.bmc.2005.01.037. Benzotropolone inhibitors of estradiol methylation: Kinetics and in silico modeling studies. Bioorganic & Medicinal Chemistry. 13. 7. 2501–7. 2005. Lambert. Joshua D. Chen. Dapeng. Wang. Ching Y. Ai. Ni. Sang. Shengmin. Ho. Chi-Tang. Welsh. William J. Yang. Chung S. 15755652.
  4. 10.1002/anie.201204910. 22969053. Discovery of Small-Molecule Inhibitors of the TLR1/TLR2 Complex. Angewandte Chemie International Edition. 51. 49. 12246–9. 2012. Cheng. Kui. Wang. Xiaohui. Zhang. Shuting. Yin. Hang. 3510333.
  5. 10.1039/ct9038300192 . XX.—Purpurogallin. I . 1903 . Perkin . Arthur George . Steven . Alec Bowring . J. Chem. Soc., Trans. . 83 . 192–201 .

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