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G8171

Sigma-Aldrich

Gambogic acid

≥95% (HPLC), powder

Synonyme(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

Formule empirique (notation de Hill):
C38H44O8
Numéro CAS:
2752-65-0
Poids moléculaire :
628.75
Code UNSPSC :
12352200
ID de substance PubChem :
329799975

Pureté

≥95% (HPLC)

Forme

powder

Couleur

yellow to orange

Solubilité

DMSO: ≥10 mg/mL
H2O: insoluble

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

GEZHEQNLKAOMCA-RRZNCOCZSA-N

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Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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
Jing Geng et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 62(2), 165-172 (2012-10-16)
Gambogic acid (GBA) targeted Heat shock protein 90 (Hsp90) and prohibited TNF-α/NF-κB signaling pathway. It can be inferred that the anti-inflammatory activity of GBA results from inhibiting the cytokine production via NF-κB signaling pathway. We used the RAW264.7 cell line
Jing Yang et al.
Journal of natural products, 75(6), 1108-1116 (2012-06-06)
Gambogic acid (1) is a cytotoxic caged xanthone derived from the resin of Garcinia hanburyi. Compound 1 selectively induces apoptosis in cancer cells, at least partially, by targeting the stress response to reactive oxygen species (ROS). However, the molecular mechanism
Hao-Peng Sun et al.
Chemistry & biodiversity, 9(8), 1579-1590 (2012-08-18)
The natural product gambogic acid exhibits high potency in inhibiting cancer cell lines. Rational medicinal modifications on gambogic acid will improve its physicochemical properties and drug-like characters. To investigate the structure-activity relationship of gambogic acid and also to find rational
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