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G8171

Sigma-Aldrich

Gambogic acid

≥95% (HPLC), powder

Synonym(s):

1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonic acid, B"-Guttiferrin, Beta-Guttiferrin, Beta-Guttilactone, Cambogic acid, Guttatic acid, Guttic acid

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About This Item

Empirical Formula (Hill Notation):
C38H44O8
CAS Number:
Molecular Weight:
628.75
UNSPSC Code:
12352200
PubChem Substance ID:

Assay

≥95% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: ≥10 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

C\C(C)=C\CC[C@@]1(C)Oc2c(C\C=C(\C)C)c3O[C@@]45[C@@H]6C[C@@H](C=C4C(=O)c3c(O)c2C=C1)C(=O)[C@]5(C\C=C(\C)C(O)=O)OC6(C)C

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

InChI key

GEZHEQNLKAOMCA-RRZNCOCZSA-N

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Biochem/physiol Actions

Gambogic acid acts as a caspase activator and apoptosis inducer, which causes an irreversible arrest in the G2/M phase of the cell cycle.

Features and Benefits

This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tao Chen et al.
Molecules (Basel, Switzerland), 17(6), 6249-6268 (2012-05-29)
Gambogic acid (GA) is in a phase II clinical trial as an antitumor and antiangiogenesis agent. In this study, 36 GA derivatives were synthesized and screened in a zebrafish model to evaluate their antiangiogenic activity and toxicity. Derivatives 4, 32
Li-jing Yang et al.
Acta pharmacologica Sinica, 34(2), 191-198 (2013-01-01)
Gambogic acid (GA) is the main active ingredient of gamboge, a brownish to orange dry resin secreted from Garcinia hanburyi, a plant that is widely distributed in nature. Recent in vitro and in vivo studies have demonstrated that GA exerts
Lianghua Fang et al.
International journal of nanomedicine, 7, 4109-4118 (2012-08-14)
The present study evaluated whether magnetic nanoparticles containing Fe(3)O(4) could enhance the activity of gambogic acid in human colon cancer cells, and explored the potential mechanisms involved. Cytotoxicity was evaluated by MTT assay. The percentage of cells undergoing apoptosis was
Zhengyun Zou et al.
BMC complementary and alternative medicine, 12, 58-58 (2012-05-02)
Gambogic acid has a marked anti-tumor effect for gastric and colorectal cancers in vitro and in vivo. However, recent investigations on gambogic acid have focused mainly on mono-drug therapy, and its potential role in cancer therapy has not been comprehensively
Abhishek Shetty et al.
Plant physiology and biochemistry : PPB, 118, 643-652 (2017-08-15)
The plant derived xanthanoid gambogic acid (GA) is well known for its anticancer activity. To date, biological actions of GA on plant system have not been reported. In the present study, we evaluated the potential acute genotoxic activity of GA

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