LKT Labs

Biochemicals for Life Science Research

(-)-Gambogic Acid

(-)-Gambogic Acid

Product ID G0248
Cas No. 2752-65-0
Purity ≥99%
Product Unit SizeCostQuantityStock
5 mg $129.20 In stock
25 mg $509.30 In stock
100 mg $1,039.50 In stock
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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
Purity

≥99%
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

beta-Guttiferrin, Cambogic acid, R-gambogic acid, Guttic acid, Guttatic acid, beta-Guttilactone, gambogoic acid
Melting Point

97.5°C
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

Downloads

MSDS

G0248 MSDS PDF
Info Sheet

G0248 Info Sheet PDF

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.

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