Purpurogallin

• CAT Number: I008912
• CAS Number: 569-77-7
• Molecular Formula: C11H8O5
• Molecular Weight: 220.18
• Purity: ≥95%
• Synonyms: 2,3,4,5-tetrahydroxybenzo[7]annulen-6-one
• InChI: 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)
• InChIKey: WDGFFVCWBZVLCE-UHFFFAOYSA-N
• SMILES: C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O

Purpurogallin is a naturally phenol extracted from the plants of Quercus spp, has potent xanthine oxidase (XO) inhibitory activity with an IC50 of 0.2 µM. Purpurogallin has antioxidant and anti-inflammatory effects[1][2][3].
Purpurogallin (50 or 100 µM; 7 or 25 hours; BV2 murine microglial cells) treatment attenuates the production of pro-inflammatory cytokines, including interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) by suppressing their mRNA and protein expression in LPS-stimulated BV2 microglial cells[1].
Purpurogallin (100 µM; 75-120 minutes; BV2 murine microglial cells) exhibits anti-inflammatory properties by suppressing the phosphatidylinositol 3-kinase/Akt and mitogen-activated protein kinase signaling pathways in LPS-stimulated BV2 microglial cells[1].
Purpurogallin (100-400 μg/kg; intraperitoneal injection; for 48 or 72 hours; male Sprague-Dawley rats) exerts its neuroinflammation effect through the dual effect of inhibiting IL-6 and TNF-α mRNA expression and reducing HMGB1 protein and mRNA expression[2].

Reference

[1]. Park HY, et al. Purpurogallin exerts anti‑inflammatory effects in lipopolysaccharide‑stimulated BV2 microglial cells through the inactivation of the NF‑κB and MAPK signaling pathways. Int J Mol Med. 2013 Nov;32(5):1171-8.
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[2]. Chang CZ, et al. Purpurogallin, a natural phenol, attenuates high-mobility group box 1 in subarachnoid hemorrhage induced vasospasm in a rat model. Int J Vasc Med. 2014;2014:254270.
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[3]. Honda S, et al. Conversion to purpurogallin, a key step in the mechanism of the potent xanthine oxidase inhibitory activity of pyrogallol. Free Radic Biol Med. 2017 May;106:228-235.
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