Pentagalloylglucose

Pentagalloylglucose (Penta-O-galloyl-β-D-glucose) is an orally active gallic tannin compound and an inducer of apoptosis and autophagy. Pentagalloglucose induces cell apoptosis and autophagy through the GSK3β/β-catenin pathway. Pentagalloylglucose inhibits UBE2T-mediated p53 ubiquitination, upregulates p53, downregulates RRM1/RRM2 in pancreatic cancer organoids. Pentagalloglucose has antioxidant, anti mutagenic, anti-inflammatory, anticonvulsant, cardioprotective, anti allergic, cholesterol lowering, and anti-tumor activities[1][2][3][4][5][6].

Product Specifications

CAS Number

[14937-32-7]

Product Name Alternative

Penta-O-galloyl-β-D-glucose; 1,2,3,4,6-Pentagalloyl glucose

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; E1/E2/E3 Enzyme; JAK; Keap1-Nrf2; Reactive Oxygen Species (ROS) ; β-catenin

Type

Natural Products

Related Pathways

Apoptosis; Epigenetics; Immunology/Inflammation; JAK/STAT Signaling; Metabolic Enzyme/Protease; NF-κB; Protein Tyrosine Kinase/RTK; Stem Cell/Wnt

Field of Research

Cancer; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose.html

Purity

99.77

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C1=CC(O)=C(O)C(O)=C1)O[C@@H]([C@@H]([C@@H](COC(C2=CC(O)=C(O)C(O)=C2)=O)O3)OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@H]([C@@H]3OC(C5=CC(O)=C(O)C(O)=C5)=O)OC(C6=CC(O)=C(O)C(O)=C6)=O

Molecular Formula

C41H32O26

Molecular Weight

940.68

Precautions

H302, H315, H319, H335

References & Citations

[1]Zeng J, et al. Pentagalloylglucose disrupts the PALB2-BRCA2 interaction and potentiates tumor sensitivity to PARP inhibitor and radiotherapy. Cancer Lett. 2022 Oct 10;546:215851. |[2]Tong J, et al. Pentagalloylglucose reduces AGE-induced inflammation by activating Nrf2/HO-1 and inhibiting the JAK2/STAT3 pathway in mesangial cells. J Pharmacol Sci. 2021 Dec;147 (4) :305-314. |[3]Fan CW, et al. Pentagalloylglucose suppresses the growth and migration of human nasopharyngeal cancer cells via the GSK3β/β-catenin pathway in vitro and in vivo. Phytomedicine. 2022 Jul 20;102:154192. |[4]Viswanatha GL, et al. Alleviation of transient global ischemia/reperfusion-induced brain injury in rats with 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranose isolated from Mangifera indica. Eur J Pharmacol. 2013 Nov 15;720 (1-3) :286-93. |[5]Kim YH, et al. 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose increases a population of T regulatory cells and inhibits IgE production in ovalbumin-sensitized mice. Int Immunopharmacol. 2015 May;26 (1) :30-6. |[6]Jiang X, et al. Targeting UBE2T Potentiates Gemcitabine Efficacy in Pancreatic Cancer by Regulating Pyrimidine Metabolism and Replication Stress. Gastroenterology. 2023 Jun;164 (7) :1232-1247.