Purpurogallin | CAS#569-77-7 | PLK1 inhibitor | TLR inhibitor

MedKoo Cat#: 406451 | Name: Purpurogallin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Purpurogallin, also known as PPG, is the aglycon of several glycosides from nutgalls and oak barks. Purpurogallin can inhibit hydroxyestradiol methylation by catechol-O-methyltransferase. Purpurogallin potently and specifically inhibits PLK, TLR1/TLR2 activation pathway. Purpurogallin showed antiplatelet and antithrombotic activities; anti‑inflammatory effects; antitumor activity, anti-oxidation activities; hepatoprotecting effects; antibacterial activity toward gram-positive bacteria.

Chemical Structure

Purpurogallin

CAS#569-77-7

Theoretical Analysis

MedKoo Cat#: 406451

Name: Purpurogallin

CAS#: 569-77-7

Chemical Formula: C11H8O5

Exact Mass: 220.0372

Molecular Weight: 220.18

Elemental Analysis: C, 60.00; H, 3.66; O, 36.33

Price and Availability

Size	Price	Availability	Quantity
500mg	USD 550.00
1g	USD 950.00

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Related CAS #

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Synonym

Purpurogallin; PPG;

IUPAC/Chemical Name

2,3,4,5-tetrahydroxy-6H-benzo[7]annulen-6-one.

InChi Key

WDGFFVCWBZVLCE-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C1C=CC=C(C=C(O)C(O)=C2O)C2=C1O

Appearance

red solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Purpurogallin is effective against Gram-positive bacteria (MICs: 11-110 µg/ml), Gram-negative bacteria (MIC: 110 µg/ml), and P. falciparum strain FCB1 clone NC-1 (IC50: 55 µM). It scavenges DPPH radicals and reduces ROS production in keratinocytes. Purpurogallin inhibits EGFR (IC50: 27.5 µM), GST (IC50: 8 µM), prolyl endopeptidase (IC50: 16 µM), glyoxalase I (IC50: 50 µM), and COMT (Ki: 0.074 µM) in cell-free assays.

In vitro activity:

Purpurogallin effectively shields human HaCaT keratinocytes from the destructive effects of UVB radiation and particulate matter 2.5 (PM2.5). It prevents apoptosis induced by UVB radiation and PM2.5 and influences the balance of pro-apoptotic and anti-apoptotic proteins through caspase signaling pathways when exposed to UVB irradiation. Purpurogallin reduced apoptosis through MAPK signaling pathways. Reference: Biomol Ther (Seoul). 2019 Jul 1;27(4):395-403. https://pubmed.ncbi.nlm.nih.gov/30419635/

In vivo activity:

Purpurogallin demonstrated neuroprotective activity against cerebral ischemia/reperfusion injury in a middle cerebral artery occlusion (MCAO/R) mouse model. Purpurogallin treatment reduced cerebral infarct area, cerebral edema, and neurological deficits in MCAO/R mice. It decreased neuronal apoptosis, levels of endoplasmic reticulum stress proteins, and inflammatory factors in the peri-infarct region of the brain. Purpurogallin acted by blocking the TLR4/NF-κB pathway in the MCAO/R mouse model. Reference: Int Immunopharmacol. 2022 Oct;111:109057. https://pubmed.ncbi.nlm.nih.gov/35964408/

Preparing Stock Solutions

The following data is based on the product molecular weight 220.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zhen AX, Piao MJ, Hyun YJ, Kang KA, Ryu YS, Cho SJ, Kang HK, Koh YS, Ahn MJ, Kim TH, Hyun JW. Purpurogallin Protects Keratinocytes from Damage and Apoptosis Induced by Ultraviolet B Radiation and Particulate Matter 2.5. Biomol Ther (Seoul). 2019 Jul 1;27(4):395-403. doi: 10.4062/biomolther.2018.151. PMID: 30419635; PMCID: PMC6609104. 2. Kim K, Kim TH, Ihn HJ, Kim JE, Choi JY, Shin HI, Park EK. Inhibitory Effect of Purpurogallin on Osteoclast Differentiation in Vitro through the Downregulation of c-Fos and NFATc1. Int J Mol Sci. 2018 Feb 17;19(2):601. doi: 10.3390/ijms19020601. PMID: 29463002; PMCID: PMC5855823. 3. Cheng Z, Li X, Ye X, Yu R, Deng Y. Purpurogallin Reverses Neuronal Apoptosis and Enhances "M2" Polarization of Microglia Under Ischemia via Mediating the miR-124-3p/TRAF6/NF-κB Axis. Neurochem Res. 2023 Feb;48(2):375-392. doi: 10.1007/s11064-022-03752-4. Epub 2022 Sep 21. PMID: 36131212. 4. Li X, Cheng Z, Chen X, Yang D, Li H, Deng Y. Purpurogallin improves neurological functions of cerebral ischemia and reperfusion mice by inhibiting endoplasmic reticulum stress and neuroinflammation. Int Immunopharmacol. 2022 Oct;111:109057. doi: 10.1016/j.intimp.2022.109057. Epub 2022 Aug 11. PMID: 35964408.

In vitro protocol:

In vivo protocol:

1. Cheng Z, Li X, Ye X, Yu R, Deng Y. Purpurogallin Reverses Neuronal Apoptosis and Enhances "M2" Polarization of Microglia Under Ischemia via Mediating the miR-124-3p/TRAF6/NF-κB Axis. Neurochem Res. 2023 Feb;48(2):375-392. doi: 10.1007/s11064-022-03752-4. Epub 2022 Sep 21. PMID: 36131212. 2. Li X, Cheng Z, Chen X, Yang D, Li H, Deng Y. Purpurogallin improves neurological functions of cerebral ischemia and reperfusion mice by inhibiting endoplasmic reticulum stress and neuroinflammation. Int Immunopharmacol. 2022 Oct;111:109057. doi: 10.1016/j.intimp.2022.109057. Epub 2022 Aug 11. PMID: 35964408.

1: Zhao P, Liu W, Wang S, Lun J. Purpurogallin carboxylic acid exhibits synergistic effects with 5‑fluorouracil on liver cancer cells in vitro by targeting ABCG2. Exp Ther Med. 2024 May 8;28(1):276. doi: 10.3892/etm.2024.12564. PMID: 38800042; PMCID: PMC11117098. 2: Ratti A, Fassi EMA, Forlani F, Zangrossi M, Mori M, Cappitelli F, Roda G, Villa S, Villa F, Grazioso G. Unlocking the Antibiofilm Potential of Natural Compounds by Targeting the NADH:quinone Oxidoreductase WrbA. Antioxidants (Basel). 2023 Aug 14;12(8):1612. doi: 10.3390/antiox12081612. PMID: 37627607; PMCID: PMC10451263. 3: Halbach L, Chevrollier LA, Doting EL, Cook JM, Jensen MB, Benning LG, Bradley JA, Hansen M, Lund-Hansen LC, Markager S, Sorrell BK, Tranter M, Trivedi CB, Winkel M, Anesio AM. Pigment signatures of algal communities and their implications for glacier surface darkening. Sci Rep. 2022 Oct 21;12(1):17643. doi: 10.1038/s41598-022-22271-4. PMID: 36271236; PMCID: PMC9587043. 4: Cheng Z, Li X, Ye X, Yu R, Deng Y. Purpurogallin Reverses Neuronal Apoptosis and Enhances "M2" Polarization of Microglia Under Ischemia via Mediating the miR-124-3p/TRAF6/NF-κB Axis. Neurochem Res. 2023 Feb;48(2):375-392. doi: 10.1007/s11064-022-03752-4. Epub 2022 Sep 21. PMID: 36131212. 5: Li X, Cheng Z, Chen X, Yang D, Li H, Deng Y. Purpurogallin improves neurological functions of cerebral ischemia and reperfusion mice by inhibiting endoplasmic reticulum stress and neuroinflammation. Int Immunopharmacol. 2022 Oct;111:109057. doi: 10.1016/j.intimp.2022.109057. Epub 2022 Aug 11. PMID: 35964408. 6: Chen S, Chen L, Jiang H. Integrated Bioinformatics and Clinical Correlation Analysis of Key Genes, Pathways, and Potential Therapeutic Agents Related to Diabetic Nephropathy. Dis Markers. 2022 May 21;2022:9204201. doi: 10.1155/2022/9204201. PMID: 35637650; PMCID: PMC9148260. 7: Liao YC, Kim T, Silva JL, Chen BY. A New Approach for Quantifying Purpurogallin in Brewed Beverages Using LC-MS in Combination with Solid Phase Extraction. Foods. 2022 May 16;11(10):1429. doi: 10.3390/foods11101429. PMID: 35626999; PMCID: PMC9141120. 8: Perini L, Gostinčar C, Likar M, Frisvad JC, Kostanjšek R, Nicholes M, Williamson C, Anesio AM, Zalar P, Gunde-Cimerman N. Interactions of Fungi and Algae from the Greenland Ice Sheet. Microb Ecol. 2023 Jul;86(1):282-296. doi: 10.1007/s00248-022-02033-5. Epub 2022 May 24. PMID: 35608637; PMCID: PMC10293465. 9: Zhang S, Wu X, Xiao Y. Conversion of lignin-derived 3-methoxycatechol to the natural product purpurogallin using bacterial P450 GcoAB and laccase CueO. Appl Microbiol Biotechnol. 2022 Jan;106(2):593-603. doi: 10.1007/s00253-021-11738-5. Epub 2021 Dec 31. PMID: 34971410. 10: Olawale F, Iwaloye O, Elekofehinti OO. Virtual screening of natural compounds as selective inhibitors of polo-like kinase-1 at C-terminal polo box and N-terminal catalytic domain. J Biomol Struct Dyn. 2022;40(24):13606-13624. doi: 10.1080/07391102.2021.1991476. Epub 2021 Oct 20. PMID: 34669551. 11: Pakosz Z, Lin TY, Michalczyk E, Nagano S, Heddle JG. Inhibitory Compounds Targeting Plasmodium falciparum Gyrase B. Antimicrob Agents Chemother. 2021 Sep 17;65(10):e0026721. doi: 10.1128/AAC.00267-21. Epub 2021 Aug 2. PMID: 34339271; PMCID: PMC8448092. 12: Wang YF, He RJ, Li DP, Huang YL. Three new compounds from the leaves of Castanopsis tibetana Hance. Nat Prod Res. 2022 Oct;36(19):4906-4910. doi: 10.1080/14786419.2021.1910690. Epub 2021 Apr 24. PMID: 33896288. 13: Souto JA, Sarno F, Nebbioso A, Papulino C, Álvarez R, Lombino J, Perricone U, Padova A, Altucci L, de Lera ÁR. A New Family of Jumonji C Domain-Containing KDM Inhibitors Inspired by Natural Product Purpurogallin. Front Chem. 2020 May 25;8:312. doi: 10.3389/fchem.2020.00312. PMID: 32523934; PMCID: PMC7261929. 14: Richard SA. Elucidating the novel biomarker and therapeutic potentials of High-mobility group box 1 in Subarachnoid hemorrhage: A review. AIMS Neurosci. 2019 Dec 2;6(4):316-332. doi: 10.3934/Neuroscience.2019.4.316. PMID: 32341986; PMCID: PMC7179354. 15: Hoham RW, Remias D. Snow and Glacial Algae: A Review1. J Phycol. 2020 Apr;56(2):264-282. doi: 10.1111/jpy.12952. Epub 2020 Feb 29. PMID: 31825096; PMCID: PMC7232433. 16: Hachim MY, Hachim IY, Elemam NM, Hamoudi RA. Toxicogenomic analysis of publicly available transcriptomic data can predict food, drugs, and chemical- induced asthma. Pharmgenomics Pers Med. 2019 Aug 26;12:181-199. doi: 10.2147/PGPM.S217535. PMID: 31692590; PMCID: PMC6717055. 17: Novak AJE, Grigglestone CE, Trauner D. A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A. J Am Chem Soc. 2019 Oct 2;141(39):15515-15518. doi: 10.1021/jacs.9b08892. Epub 2019 Sep 23. PMID: 31518120; PMCID: PMC7249536. 18: Wu CQ, Chen GH. Detection of synergistic effect of superoxide dismutase and jujubosides on scavenging superoxide anion radical by capillary electrophoresis. Biomed Chromatogr. 2019 Oct;33(10):e4630. doi: 10.1002/bmc.4630. Epub 2019 Aug 1. PMID: 31243785. 19: Xie X, Zu X, Liu F, Wang T, Wang X, Chen H, Liu K, Wang P, Liu F, Zheng Y, Bode AM, Dong Z, Kim DJ. Purpurogallin is a novel mitogen-activated protein kinase kinase 1/2 inhibitor that suppresses esophageal squamous cell carcinoma growth in vitro and in vivo. Mol Carcinog. 2019 Jul;58(7):1248-1259. doi: 10.1002/mc.23007. Epub 2019 May 17. PMID: 31100197. 20: Rambabu M, Jayanthi S. Virtual screening of National Cancer Institute database for claudin-4 inhibitors: Synthesis, biological evaluation, and molecular dynamics studies. J Cell Biochem. 2019 May;120(5):8588-8600. doi: 10.1002/jcb.28147. Epub 2018 Nov 26. PMID: 30474874.