(-)-GAMBOGIC ACID
G0248
2752-65-0
≥99%
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5mg In stock $500.00
25mg In stock $780.00
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Description

(-)-Gambogic acid is a xanthone found in the resin of the Garcinia hanburyi tree and has shown considerable anticancer chemotherapeutic, chemopreventive, and anti-angiogenic activities in both in vitro and in vivo studies. Gambogic acid inhibits cellular growth and induces apoptosis through a variety of mechanisms. This compound induces LRIG1 upregulation and EGFR degradation to inactivate Akt signaling. Additionally, gambogic acid also inhibits NF-κB signaling through interaction with the transferrin receptor, causing reduction of c-MYC expression, inhibition of telomerase activity and mRNA production, and disruption of mitochondrial outer membrane potential.

Product Info

Cas No. 2752-65-0
Formula C38H44O8
Formula Wt. 628.75
Chemical Name (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
IUPAC Name (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
Synonym gambogic acid;Beta-Guttiferrin;GAMBOGIC ACID(AS);cambogicacid;GUTTATIC ACID;GUTTIC ACID;1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonic acid;B"-Guttiferrin;Beta-Guttilactone;AK160232;CID 126963722;GAMBOGICACID;Isogambogic acid;Spectrum_000175;Spectrum2_000388;Spectrum3_000707;Spectrum4_001940;KBioGR_002321;KBioSS_000655;DivK1c_001020;SPBio_000575;KBio1_001020;KBio2_000655;KBio2_003223;KBio2_005791;KBio3_001713;NINDS_001020
Solubility Insoluble in water, soluble in DMSO (25 mg/mL), and ethanol (25 mg/mL).
Appearance Yellow-orange solid

Shipping and Storage

Store Temp -20°C
Ship Temp ambient

References

He XY, Liu XJ, 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. 2013 Jun 7;435(3):397-402. PMID: 23665322.

Gu H, Rao S, Zhao J, et al. Gambogic acid reduced bcl-2 expression via p53 in human breast MCF-7 cancer cells. J Cancer Res Clin Oncol. 2009 Dec;135(12):1777-82. PMID: 19582475.

Nie F, Zhang X, Qi Q, et al. Reactive oxygen species accumulation contributes to gambogic acid-induced apoptosis in human hepatoma SMMC-7721 cells. Toxicology. 2009 Jun 16;260(1-3):60-7. PMID: 19464570.

Pandey MK, Sung B, Ahn KS, et al. Gambogic acid, a novel ligand for transferrin receptor, potentiates TNF-induced apoptosis through modulation of the nuclear factor-kappaB signaling pathway. Blood. 2007 Nov 15;110(10):3517-25. PMID: 17673602.

Wu ZQ, Guo QL, You QD, et al. Gambogic acid inhibits proliferation of human lung carcinoma SPC-A1 cells in vivo and in vitro and represses telomerase activity and telomerase reverse transcriptase mRNA expression in the cells. Biol Pharm Bull. 2004 Nov;27(11):1769-74. PMID: 15516720.