A xanthonoid with anticancer activity
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Gambogic Acid

Item No. 14761

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-buten-1-yl)-11-(4-methyl-3-penten-1-yl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2Z-butenoic acid
CAS Number
2752-65-0
Synonyms
  • GA
  • β-Guttiferin
Molecular Formula
C38H44O8
Formula Weight
628.8
Purity
≥95% (mixture of epimers)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16.7 mg/mlDMSO: 16.7 mg/mlEthanol: 25 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
291, 361 nm
SMILES
C/C(C(O)=O)=C/C[C@@]1(OC(C)(C)[C@]2([H])C3)[C@@]2(OC4=C(C5=C6C=C[C@](CC/C=C(C)/C)(C)O5)C/C=C(C)/C)C(C(C4=C6O)=O)=C[C@@]3([H])C1=O
InChi Code
InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37
InChi Key
GEZHEQNLKAOMCA-RRZNCOCZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $37

    Add

    5 mg

    $98

    Add

    10 mg

    $139

    Add

    25 mg

    $209

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Gambogic acid (GA) is a xanthonoid that has been found in G. hanburyi resin and has anticancer activity.1,2,3 It binds covalently to the regulatory subunit B (SPTSSB) of the serine palmitoyltransferase complex (Ki = 1.5 µM; kinact = 0.05 min-1) and inhibits de novo sphingolipid biosynthesis.1 GA activates caspases in T47D breast cancer cells (EC50 = 0.78 µM) and inhibits binding of anti-apoptotic proteins to a BH3 peptide (IC50s = 1.47, 1.21, 2.02, 0.66, 1.06, and 0.79 μM for Bcl-xL, Bcl-2, Bcl-W, Bcl-B, Bfl-1, and Mcl-1, respectively), as well as decreases the expression of Bcl-2 and increases the expression of Bax in MGC-803 human gastric carcinoma cells.4,5,6 GA binds to the transferrin receptor (IC50 = 4.1 µM), reduces growth of a variety of cancer cell lines (GI50s = 0.115-1 µM), and induces apoptosis in T47D cells.2 It also inhibits growth of U87 glioma cells, as well as increases the levels of leucine-rich repeats and immunoglobulin-like domains protein 1 (LRIG1), decreases the levels of EGFR, and reduces Akt/mTORC1 signaling in these cells.3 GA inhibits the chymotrypsin activity of the 20S proteasome in a dose-dependent manner and is a slow inhibitor of inward-rectifying potassium channel 2.1 (Kir2.1; IC50 = <0.1 µM).7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoch, D.G., Abegg, D., Hannich, J.T., et al. Combined omics approach identifies gambogic acid and related xanthones as covalent inhibitors of the serine palmitoyltransferase complex. Cell Chem. Bio. 27(5), 586-597 (2020).

    2. Kasibhatla, S., Jessen, K.A., Maliartchouk, S., et al. A role for transferrin receptor in triggering apoptosis when targeted with gambogic acid. Proc. Natl. Acad. Sci. USA 102(34), 12095-12100 (2005).

    3. He, X.y., Liu, X.j., Chen, X., et al. Gambogic acid induces EGFR degradation and Akt/mTORC1 inhibition through AMPK dependent-LRIG1 upregulation in cultured U87 glioma cells. Biochem. Biophys. Res. Commun. 435(3), 397-402 (2013).

    4. Zhang, H.Z., Kasibhatla, S., Wang, Y., et al. Discovery, characterization and SAR of gambogic acid as a potent apoptosis inducer by a HTS assay. Bioorg. Med. Chem. 12(2), 309-317 (2004).

    5. Zhai, D., Jin, C., Shiau, C.W., et al. Gambogic acid is an antagonist of anti-apoptotic Bcl-2-family proteins. Mol. Cancer Ther. 7(6), 1639-1646 (2008).

    6. Zhao, L., Guo, Q.L., You, Q.D., et al. Gambogic acid induces apoptosis and regulates expressions of Bax and Bcl-2 protein in human gastric carcinoma MGC-803 cells. Biol. Pharm. Bull. 27(7), 998-1003 (2004).

    7. Felth, J., Lesiak-Mieczkowska, K., D'Arcy, P., et al. Gambogic acid is cytotoxic to cancer cells through inhibition of the ubiquitin-proteasome system. Invest. New Drugs 31(3), 587-598 (2013).

    8. Zaks-Makhina, E., Li, H., Grishin, A., et al. Specific and slow inhibition of the Kir2.1 K+ channel by gambogic acid. The Journal of Biological Chemisty 284(23), 15432-15438 (2009).