Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C41H32O26 |
| Molecular Weight | 940.6772 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]2O[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H](OC(=O)C5=CC(O)=C(O)C(O)=C5)[C@@H]2OC(=O)C6=CC(O)=C(O)C(O)=C6
InChI
InChIKey=QJYNZEYHSMRWBK-NIKIMHBISA-N
InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1
| Molecular Formula | C41H32O26 |
| Molecular Weight | 940.6772 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract. | 2010-09-15 |
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| Antioxidant effects of secondary metabolites from Geranium psilostemon. | 2010-06 |
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| Effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on elastase and hyaluronidase activities and its type II collagen expression. | 2010-04-08 |
|
| 1,2,3,4,6-Penta-O-galloly-beta-D-glucose suppresses hypoxia-induced accumulation of hypoxia-inducible factor-1α and signaling in LNCaP prostate cancer cells. | 2010 |
|
| Penta-O-galloyl-beta-D-glucose induces G1 arrest and DNA replicative S-phase arrest independently of cyclin-dependent kinase inhibitor 1A, cyclin-dependent kinase inhibitor 1B and P53 in human breast cancer cells and is orally active against triple negative xenograft growth. | 2010 |
|
| 1,2,3,4,6-penta-O-galloyl-beta-D-glucose protects splenocytes against radiation-induced apoptosis in murine splenocytes. | 2010 |
|
| Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy. | 2010 |
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| Suppression of thymus- and activation-regulated chemokine (TARC/CCL17) production by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose via blockade of NF-kappaB and STAT1 activation in the HaCaT cells. | 2009-09-11 |
|
| [Chemical constituents from roots of Distylium myricoides]. | 2009-09 |
|
| Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cells. | 2009-08 |
|
| Antioxidant and hepatoprotective activities of thai mango seed kernel extract. | 2009-08 |
|
| Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa. | 2009-07-10 |
|
| A traditional medicinal herb Paeonia suffruticosa and its active constituent 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose have potent anti-aggregation effects on Alzheimer's amyloid beta proteins in vitro and in vivo. | 2009-06 |
|
| Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1. | 2009-05 |
|
| Penta-O-galloyl-beta-D-glucose suppresses prostate cancer bone metastasis by transcriptionally repressing EGF-induced MMP-9 expression. | 2009-04-22 |
|
| 1,2,3,4,6-penta-O-galloyl-beta-D-glucose attenuates renal cell migration, hyaluronan expression, and crystal adhesion. | 2009-03-15 |
|
| Novel biological properties of Oenothera paradoxa defatted seed extracts: effects on metallopeptidase activity. | 2008-09-10 |
|
| 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Galla Rhois protects primary rat hepatocytes from necrosis and apoptosis. | 2008-09 |
|
| Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection. | 2008-08 |
|
| Antioxidative activity of geranium (Pelargonium inquinans Ait) and its active component, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose. | 2008-04 |
|
| Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC. | 2007-09 |
|
| The isolation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Acer truncatum Bunge by high-speed counter-current chromatography. | 2007-05-01 |
|
| Elastin stabilization for treatment of abdominal aortic aneurysms. | 2007-04-03 |
|
| Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose, castalagin, and grandinin. | 2006-12-13 |
|
| In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus. | 2006-10 |
|
| 1,2,3,4,6-penta-O-galloyl-beta-D-glucose up-regulates heme oxygenase-1 expression by stimulating Nrf2 nuclear translocation in an extracellular signal-regulated kinase-dependent manner in HepG2 cells. | 2006-01-14 |
|
| Vasodilatory and anti-inflammatory effects of the 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) via a nitric oxide-cGMP pathway. | 2005-11-07 |
|
| Phenolic constituents of galla Rhois with hepatoprotective effects on tacrine- and nitrofurantoin-induced cytotoxicity in Hep G2 cells. | 2005-11 |
|
| Natural anti-diabetic compound 1,2,3,4,6-penta-O-galloyl-D-glucopyranose binds to insulin receptor and activates insulin-mediated glucose transport signaling pathway. | 2005-10-21 |
|
| Enzymology of gallotannin and ellagitannin biosynthesis. | 2005-09 |
|
| Penta-O-galloyl-beta-D-glucose suppresses tumor growth via inhibition of angiogenesis and stimulation of apoptosis: roles of cyclooxygenase-2 and mitogen-activated protein kinase pathways. | 2005-08 |
|
| Chemical identification of the sources of commercial Fructus Chebulae. | 2005-07-27 |
|
| In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds. | 2005 |
|
| Green tea: Health benefits as cancer preventive for humans. | 2005 |
|
| Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease. | 2004-12-20 |
|
| Theaflavin-3,3'-digallate and penta-O-galloyl-beta-D-glucose inhibit rat liver microsomal 5alpha-reductase activity and the expression of androgen receptor in LNCaP prostate cancer cells. | 2004-07 |
|
| 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose blocks endothelial cell growth and tube formation through inhibition of VEGF binding to VEGF receptor. | 2004-05-10 |
|
| Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds. | 2004-03 |
|
| Penta-O-galloyl-beta-D-glucose inhibits phorbol myristate acetate-induced interleukin-8 [correction of intereukin-8] gene expression in human monocytic U937 cells through its inactivation of nuclear factor-kappaB. | 2004-03 |
|
| Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 activity by 1,2,3,4,6-penta-O-galloyl-beta-D-glucose in murine macrophage cells. | 2003-10 |
|
| Paeonianins A-E, new dimeric and monomeric ellagitannins from the fruits of Paeonia lactiflora. | 2003-06 |
|
| Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves. | 2003-02 |
|
| Inhibitory effects of the root cortex of Paeonia suffruticosa on interleukin-8 and macrophage chemoattractant protein-1 secretions in U937 cells. | 2003-01 |
|
| Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir. | 2002-12 |
|
| Penta-O-galloyl-beta-D-glucose inhibits the invasion of mouse melanoma by suppressing metalloproteinase-9 through down-regulation of activator protein-1. | 2002-10-25 |
|
| 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose protects rat neuronal cells (Neuro 2A) from hydrogen peroxide-mediated cell death via the induction of heme oxygenase-1. | 2002-08-09 |
|
| Respiratory syncytial virus infection induces matrix metalloproteinase-9 expression in epithelial cells. | 2002 |
|
| In vitro anti-proliferative effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on human hepatocellular carcinoma cell line, SK-HEP-1 cells. | 2001-12-10 |
|
| Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography--electrospray ionisation mass spectrometry. | 2001-11-14 |
|
| Inhibition of human immunodeficiency viral replication by tannins and related compounds. | 1992-05 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:28:31 GMT 2025
by
admin
on
Mon Mar 31 22:28:31 GMT 2025
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| Record UNII |
3UI3K8W93I
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| Record Status |
Validated (UNII)
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| Record Version |
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3UI3K8W93I
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131647-34-2
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18082
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102694-50-8
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DTXSID901029765
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99935-72-5
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14937-32-7
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1,2,3,4,6-Pentagalloyl glucose
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98731-29-4
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94008-28-3
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65238
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
PGG decreased the level of extracellular HBV (IC50, 1.0m g/ml) in a dose-dependent manner. PGG also reduced the HBsAg level by 25% at a concentration of 4m g/ml.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
MIC 160 mg/L of ATCC 700392 and ATCC 700824 strains of H. pylori
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The inhibition of protein tyrosine phosphatase 1B (PTP1B) is of substantial interest for the treatment of type-2 diabetes mellitus. Using an in vitro enzyme assay with human recombinant PTP1B 1,2,3,4,6-penta-O-galloyl-D-glucopyranose(1) was isolated from the roots of Paeonia lactiflora as an inhibitor of PTP1B, with an IC50 value of 4.8 uM.
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