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Chemical Structure| 14937-32-7 Chemical Structure| 14937-32-7

Structure of 14937-32-7

Chemical Structure| 14937-32-7

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1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose, a natural product isolated and purified from the peel of Punica granatum L., suppresses interleukin (IL)-4 induced signal pathway in B cell, and inhibits IgE production partially caused by increasing a population of Treg cells in conjunction with Treg-inducing factors.

Synonyms: Penta-O-galloyl-β-D-glucose; Pentagalloylglucose; DB-03208

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Product Details of 1,2,3,4,6-O-pentagalloylglucose

CAS No. :14937-32-7
Formula : C41H32O26
M.W : 940.68
SMILES Code : 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
Synonyms :
Penta-O-galloyl-β-D-glucose; Pentagalloylglucose; DB-03208
MDL No. :MFCD03788860
InChI Key :QJYNZEYHSMRWBK-NIKIMHBISA-N
Pubchem ID :65238

Safety of 1,2,3,4,6-O-pentagalloylglucose

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Peripheral blood mononuclear cells (PBMCs) 20 µM PGG significantly inhibited the levels of IFN-β, TNF-α, IL-6, and CXCL10 PMC11428449
THP-1 cells 5, 10, 20 µM 1 h PGG reduced the expression of p-IRF3 and p-STING protein and inhibited the expression of IFN-β, TNF-α, IL-6, and CXCL10 PMC11428449
Bone marrow-derived macrophages (BMDMs) 5, 10, 20 µM 1 h PGG gradient inhibited the phosphorylation of IRF3 and STING and reduced the mRNA expression of IFN-β, TNF-α, IL-6, ISG15, and CXCL10 PMC11428449
TRAMP-C2 cells 25 μM 24 h PGG significantly inhibited the growth of TRAMP-C2 cells and induced caspase-independent programmed cell death and autophagic features PMC2838500
PC-3 cells 50, 75 μM 4 days PGG significantly decreased the number of adherent PC-3 cells and induced autophagic features and caspase-independent programmed cell death PMC2838500
BHK-21 cells 10 μM 24 h PGG significantly downregulated the level of phosphorylated STAT3 (p-STAT3) and upregulated SOCS3 whether PGG was used with or without CVS-11 infection, and, as expected, PGG induced significant inhibition of virus replication at the levels of all proteins and mRNAs and virus titers. PMC6714789
MC3T3-E1 cells 1×10−3 µM 24 h PGG significantly enhanced cell viability and decreased cell apoptosis by restoring mitochondrial function, attenuating reactive oxygen species levels, decreasing the mitochondrial membrane potential, and enhancing ATP production. PMC11547736

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6 mice Acetaminophen-induced acute liver injury model Intraperitoneal injection 20 and 40 mg/kg Single administration, lasting 24 hours PGG reduced serum ALT, AST, and ALP levels, improved liver tissue damage and apoptosis, and inhibited acetaminophen-induced cGAS-STING pathway activation PMC11428449
Sprague Dawley rats LPS-induced acute lung injury model Intraperitoneal injection 60 and 30 mg/kg Administered 48, 24, and 1 hour before LPS, lasting for 3 days PGG inhibited inflammation and oxidative stress by activating the AMPK/PI3K/Akt/Nrf2 pathway, significantly alleviating pulmonary edema and histological changes, reducing total leukocyte count and pro-inflammatory cytokines IL-6 and IL-1β production, and decreasing oxidative stress markers MDA formation and SOD depletion. PMC9699101
Nude mice Human DU145 and PC-3 prostate cancer xenograft models Not specified 20 mg/kg Daily administration PGG suppressed the growth of human DU145 and PC-3 prostate cancer xenografts in nude mice, suggesting potential utility as a PCa chemotherapeutic or chemopreventive agent PMC2838500
Sprague Dawley (SD) male rats LPS-induced acute lung injury model Oral 17.16 mg/kg Administered 48, 24, and 1 hour before LPS, lasting for 12 hours PGG significantly inhibited lung edema, attenuated pulmonary histological changes, and reduced the number of total cells and neutrophils in BALF. PMC6304083

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.06mL

0.21mL

0.11mL

5.32mL

1.06mL

0.53mL

10.63mL

2.13mL

1.06mL

References

[1]Kim YH, Yang X, 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.

[2]Viswanatha GL, Shylaja H, Mohan CG. 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.

[3]Kim YH, Yang X, Yamashita S, Kumazoe M, Huang Y, Nakahara K, Won YS, Murata M, Lin IC, Tachibana H. 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

[4]de Almeida NEC, Do TD, LaPointe NE, Tro M, Feinstein SC, Shea JE, Bowers MT. 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose Binds to the N-terminal Metal Binding Region to Inhibit Amyloid β-protein Oligomer and Fibril Formation. Int J Mass Spectrom. 2017 Sep;420:24-34

[5]Cryan LM, Bazinet L, Habeshian KA, Cao S, Clardy J, Christensen KA, Rogers MS. 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2. J Med Chem. 2013 Mar 14;56(5):1940-5

[6]Xiang Q, Tang J, Luo Q, Xue J, Tao Y, Jiang H, Tian J, Fan C. In vitro study of anti-ER positive breast cancer effect and mechanism of 1,2,3,4-6-pentyl-O-galloyl-beta-d-glucose (PGG). Biomed Pharmacother. 2019 Mar;111:813-820

[7]Lin MH, Shu JC, Huang HY, Cheng YC. Involvement of iron in biofilm formation by Staphylococcus aureus. PLoS One. 2012;7(3):e34388

 

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