WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206103
Description: Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. This natural chemical has shown promising antitumor activity in clinical trials. Gambogic acid inhibits cell proliferation, angiogenesis and metastasis. Gambogic acid is currently in clinical trials in China.
MedKoo Cat#: 206103
Name: Gambogic acid
Chemical Formula: C38H44O8
Exact Mass: 628.30362
Molecular Weight: 628.75
Elemental Analysis: C, 72.59; H, 7.05; O, 20.36
Synonym: B-Guttiferrin; Beta-Guttiferrin; Beta-Guttilactone; Cambogic acid; Guttatic acid; Guttic acid.
IUPAC/Chemical Name: (Z)-4-((1S,3aR,5S,11R,14aS)-8-hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-2,3a,4,5,7,11-hexahydro-1H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a-yl)-2-methylbut-2-enoic acid
InChi Key: GEZHEQNLKAOMCA-RRZNCOCZSA-N
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+,38-/m1/s1
SMILES Code: O=C(O)/C(C)=C\C[C@@](C([C@]1([H])C=C23)=O)(OC(C)(C)[C@]4([H])C1)[C@@]24OC5=C(C(O)=C(C=C[C@](CC/C=C(C)/C)(C)O6)C6=C5C/C=C(C)\C)C3=O
Gambogic acid is the principal pigment of gambooge resin which, in addition to early medicinal uses in Southeast Asia, is also a sought after dye due to the bright orange color it imparts to cloth. According to traditional Chinese medical documentation, gamboge was described as poisonous and acidic and possessed the ability to detoxify, kill parasites, and stop bleeding as a hemostatic agent. Gambogic acid has also been used in various food preparations in Asian cultures. (http://en.wikipedia.org/wiki/Gambogic_acid) In studies conducted with mice and transplanted tumors (from human lung carcinoma SPC-A1 cells), tumor growth remained suppressed for up to 21 days during treatment with gambogic acid. The ratio of relative tumor volume (RTV) for the treated group of mice to the control group indicates the gambogic acid was having an impact on tumor size while having no adverse effects on body weight or mortality. Tumor volume was measured twice each week during the study, and the ratio of treated to control group tumor volume ranged from 45.0% to 72.7% for the 8 mg/kg dose and from 55.6% to 78.8% for the 4 mg/kg dose. Tumor growth rate shows a dependence on the dose of gambogic acid, with the 8 mg/kg dose providing improved results at suppressing tumor growth in these trials. (http://en.wikipedia.org/wiki/Gambogic_acid) The effect of gambogic acid on the growth of SPC-A1 cells was also investigated. Cells were cultured with various concentrations of gambogic acid, and then living cells were counted. The results indicate that both the concentration of gambogic acid used to treat the cells as well as the length of treatment affected the growth inhibiting factor. For the same length of exposure, the higher the concentration of gambogic acid that was administered, the greater the effect on inhibiting cell growth. When comparing cultures at the same dose, the longer the cells were exposed to gambogic acid, the higher the growth inhibition. Results indicate that cell growth is dependent on both the magnitude of the dose administered as well as the length of time exposed to gambogic acid. (http://en.wikipedia.org/wiki/Gambogic_acid)
1: Qi Q, Lu N, Li C, Zhao J, Liu W, You Q, Guo Q. Involvement of RECK in gambogic acid induced anti-invasive effect in A549 human lung carcinoma cells. Mol Carcinog. 2014 Feb 14. doi: 10.1002/mc.22138. [Epub ahead of print] PubMed PMID: 24532189.
2: Wang Y, Xiang W, Wang M, Huang T, Xiao X, Wang L, Tao D, Dong L, Zeng F, Jiang G. Methyl jasmonate sensitizes human bladder cancer cells to gambogic acid-induced apoptosis through down-regulation of EZH2 expression by miR-101. Br J Pharmacol. 2014 Feb;171(3):618-35. doi: 10.1111/bph.12501. PubMed PMID: 24490857.
3: Duan D, Zhang B, Yao J, Liu Y, Sun J, Ge C, Peng S, Fang J. Gambogic acid induces apoptosis in hepatocellular carcinoma SMMC-7721 cells by targeting cytosolic thioredoxin reductase. Free Radic Biol Med. 2014 Apr;69:15-25. doi: 10.1016/j.freeradbiomed.2013.12.027. Epub 2014 Jan 7. PubMed PMID: 24407164.
4: Liu N, Huang H, Liu S, Li X, Yang C, Dou QP, Liu J. Calcium channel blocker verapamil accelerates gambogic acid-induced cytotoxicity via enhancing proteasome inhibition and ROS generation. Toxicol In Vitro. 2014 Apr;28(3):419-25. doi: 10.1016/j.tiv.2013.12.008. Epub 2013 Dec 27. PubMed PMID: 24373880.
5: Shi X, Chen X, Li X, Lan X, Zhao C, Liu S, Huang H, Liu N, Liao S, Song W, Zhou P, Wang S, Xu L, Wang X, Dou QP, Liu J. Gambogic acid induces apoptosis in imatinib-resistant chronic myeloid leukemia cells via inducing proteasome inhibition and caspase-dependent Bcr-Abl downregulation. Clin Cancer Res. 2014 Jan 1;20(1):151-63. doi: 10.1158/1078-0432.CCR-13-1063. Epub 2013 Dec 12. PubMed PMID: 24334603; PubMed Central PMCID: PMC3938960.
6: Wang LH, Li Y, Yang SN, Wang FY, Hou Y, Cui W, Chen K, Cao Q, Wang S, Zhang TY, Wang ZZ, Xiao W, Yang JY, Wu CF. Gambogic acid synergistically potentiates cisplatin-induced apoptosis in non-small-cell lung cancer through suppressing NF-κB and MAPK/HO-1 signalling. Br J Cancer. 2014 Jan 21;110(2):341-52. doi: 10.1038/bjc.2013.752. Epub 2013 Dec 3. PubMed PMID: 24300974; PubMed Central PMCID: PMC3899775.
7: Liu N, Huang H, Xu L, Hua X, Li X, Liu S, Yang C, Zhao C, Zhao C, Li S, Dou QP, Liu J. The combination of proteasome inhibitors bortezomib and gambogic acid triggers synergistic cytotoxicity in vitro but not in vivo. Toxicol Lett. 2014 Jan 30;224(3):333-40. doi: 10.1016/j.toxlet.2013.11.021. Epub 2013 Nov 26. PubMed PMID: 24291039.
8: Wang LH, Yang JY, Yang SN, Li Y, Ping GF, Hou Y, Cui W, Wang ZZ, Xiao W, Wu CF. Suppression of NF-κB signaling and P-glycoprotein function by gambogic acid synergistically potentiates adriamycin -induced apoptosis in lung cancer. Curr Cancer Drug Targets. 2014 Jan;14(1):91-103. PubMed PMID: 24245692.
9: Xu P, Li J, Shi L, Selke M, Chen B, Wang X. Synergetic effect of functional cadmium-tellurium quantum dots conjugated with gambogic acid for HepG2 cell-labeling and proliferation inhibition. Int J Nanomedicine. 2013;8:3729-36. doi: 10.2147/IJN.S51622. Epub 2013 Sep 30. PubMed PMID: 24109183; PubMed Central PMCID: PMC3792847.
10: Yu F, He C, Waddad AY, Munyendo WL, Lv H, Zhou J, Zhang Q. N-octyl-N-arginine-chitosan (OACS) micelles for gambogic acid oral delivery: preparation, characterization and its study on in situ intestinal perfusion. Drug Dev Ind Pharm. 2013 May 17. [Epub ahead of print] PubMed PMID: 23679668.