Home Other Building Blocks 1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose

1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose

CAS No.:
14937-32-7
Catalog Number:
AG00AOJG
Molecular Formula:
C41H32O26
Molecular Weight:
940.6772
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥95%
1 week
United States
$139
- +
10mg
≥95%
1 week
United States
$187
- +
25mg
≥95%
1 week
United States
$262
- +
50mg
99%
1 week
United States
$490
- +
100mg
99%
1 week
United States
$807
- +
Product Description
Catalog Number:
AG00AOJG
Chemical Name:
1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose
CAS Number:
14937-32-7
Molecular Formula:
C41H32O26
Molecular Weight:
940.6772
MDL Number:
MFCD03788860
IUPAC Name:
[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
InChI:
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
InChI Key:
QJYNZEYHSMRWBK-NIKIMHBISA-N
SMILES:
O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1OC(COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
EC Number:
604-691-5
UNII:
3UI3K8W93I
Properties
Complexity:
1680  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
940.118g/mol
Formal Charge:
0
Heavy Atom Count:
67  
Hydrogen Bond Acceptor Count:
26  
Hydrogen Bond Donor Count:
15  
Isotope Atom Count:
0
Molecular Weight:
940.681g/mol
Monoisotopic Mass:
940.118g/mol
Rotatable Bond Count:
16  
Topological Polar Surface Area:
444A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.6  
Literature
Title Journal
Reactive oxygen species-mediated activation of JNK and down-regulation of DAXX are critically involved in penta-O-galloyl-beta-d-glucose-induced apoptosis in chronic myeloid leukemia K562 cells. Biochemical and biophysical research communications 20120803
A review of animal and human studies for management of benign prostatic hyperplasia with natural products: perspective of new pharmacological agents. Inflammation & allergy drug targets 20120601
Hamamelitannin from witch hazel (Hamamelis virginiana) displays specific cytotoxic activity against colon cancer cells. Journal of natural products 20120127
Aqueous Extract of Paeonia suffruticosa Inhibits Migration and Metastasis of Renal Cell Carcinoma Cells via Suppressing VEGFR-3 Pathway. Evidence-based complementary and alternative medicine : eCAM 20120101
Involvement of iron in biofilm formation by Staphylococcus aureus. PloS one 20120101
A gallotannin-rich fraction from Caesalpinia spinosa (Molina) Kuntze displays cytotoxic activity and raises sensitivity to doxorubicin in a leukemia cell line. BMC complementary and alternative medicine 20120101
Gelatin tannate reduces the proinflammatory effects of lipopolysaccharide in human intestinal epithelial cells. Clinical and experimental gastroenterology 20120101
Insulin receptor signaling activated by penta-O-galloyl-α-D: -glucopyranose induces p53 and apoptosis in cancer cells. Apoptosis : an international journal on programmed cell death 20110901
Pharmacological evaluation of insulin mimetic novel suppressors of PEPCK gene transcription from Paeoniae Rubra Radix. Journal of ethnopharmacology 20110901
The genome-wide expression profile of 1,2,3,4,6-penta-O-galloyl-β-D-glucose-treated MDA-MB-231 breast cancer cells: molecular target on cancer metabolism. Molecules and cells 20110831
1,2,3,4,6-penta-O-galloyl-β-D-glucose, quercetin, curcumin and lycopene induce cell-cycle arrest in MDA-MB-231 and BT474 cells through downregulation of Skp2 protein. Journal of agricultural and food chemistry 20110622
Oral administration of penta-O-galloyl-β-D-glucose suppresses triple-negative breast cancer xenograft growth and metastasis in strong association with JAK1-STAT3 inhibition. Carcinogenesis 20110601
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose reduces renal crystallization and oxidative stress in a hyperoxaluric rat model. Kidney international 20110301
Conformation of the tridimensional structure of 1,2,3,4,6-pentagalloyl-β-D-glucopyranose (PGG) by (1)H NMR, NOESY and theoretical study and membrane interaction in a simulated phospholipid bilayer: a first insight. Magnetic resonance in chemistry : MRC 20110301
A novel small molecule 1,2,3,4,6-penta-O-galloyl-α-D-glucopyranose mimics the antiplatelet actions of insulin. PloS one 20110101
Bioactivity-guided isolation of 1,2,3,4,6-Penta-O-galloyl-D-glucopyranose from Paeonia lactiflora roots as a PTP1B inhibitor. Journal of natural products 20100924
Oenothera paradoxa defatted seeds extract and its bioactive component penta-O-galloyl-β-D-glucose decreased production of reactive oxygen species and inhibited release of leukotriene B4, interleukin-8, elastase, and myeloperoxidase in human neutrophils. Journal of agricultural and food chemistry 20100922
Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract. Journal of ethnopharmacology 20100915
Antioxidant effects of secondary metabolites from Geranium psilostemon. Natural product communications 20100601
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos. Bioorganic & medicinal chemistry letters 20100301
Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy. Journal of Alzheimer's disease : JAD 20100101
Effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on elastase and hyaluronidase activities and its type II collagen expression. Acta poloniae pharmaceutica 20100101
1,2,3,4,6-penta-O-galloyl-beta-D-glucose protects splenocytes against radiation-induced apoptosis in murine splenocytes. Biological & pharmaceutical bulletin 20100101
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. Breast cancer research : BCR 20100101
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. Biological & pharmaceutical bulletin 20100101
Polyphenol-stabilized tubular elastin scaffolds for tissue engineered vascular grafts. Tissue engineering. Part A 20091001
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. Biochemical and biophysical research communications 20090911
[Chemical constituents from roots of Distylium myricoides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090901
Antioxidant and hepatoprotective activities of thai mango seed kernel extract. Planta medica 20090801
Melanogenesis inhibition by gallotannins from Chinese galls in B16 mouse melanoma cells. Biological & pharmaceutical bulletin 20090801
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. Journal of neurochemistry 20090601
Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1. Carcinogenesis 20090501
Penta-O-galloyl-beta-D-glucose suppresses prostate cancer bone metastasis by transcriptionally repressing EGF-induced MMP-9 expression. Journal of agricultural and food chemistry 20090422
1,2,3,4,6-penta-O-galloyl-beta-D-glucose attenuates renal cell migration, hyaluronan expression, and crystal adhesion. European journal of pharmacology 20090315
Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa. Journal of cosmetic science 20090101
Novel biological properties of Oenothera paradoxa defatted seed extracts: effects on metallopeptidase activity. Journal of agricultural and food chemistry 20080910
1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Galla Rhois protects primary rat hepatocytes from necrosis and apoptosis. Planta medica 20080901
Penta-1,2,3,4,6-O-galloyl-beta-D-glucose induces p53 and inhibits STAT3 in prostate cancer cells in vitro and suppresses prostate xenograft tumor growth in vivo. Molecular cancer therapeutics 20080901
Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection. Phytotherapy research : PTR 20080801
Antioxidative activity of geranium (Pelargonium inquinans Ait) and its active component, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose. Phytotherapy research : PTR 20080401
[Determination of 1, 2, 3, 4, 6-penta-O-galloyl-D-glucose in forty four kinds of Chinese traditional medicines by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080301
Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC. Canadian journal of physiology and pharmacology 20070901
The isolation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Acer truncatum Bunge by high-speed counter-current chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070501
Elastin stabilization for treatment of abdominal aortic aneurysms. Circulation 20070403
Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose, castalagin, and grandinin. Journal of agricultural and food chemistry 20061213
In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus. Biological & pharmaceutical bulletin 20061001
[Studies on HPLC fingerprint of cortex moutan]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061001
Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues. Journal of medicinal chemistry 20060504
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. World journal of gastroenterology 20060114
Role of peptide primary sequence in polyphenol-protein recognition: an example with neurotensin. Biochimica et biophysica acta 20051130
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. European journal of pharmacology 20051107
Phenolic constituents of galla Rhois with hepatoprotective effects on tacrine- and nitrofurantoin-induced cytotoxicity in Hep G2 cells. Biological & pharmaceutical bulletin 20051101
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. Biochemical and biophysical research communications 20051021
Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry 20050901
Anticoagulant 1,2,3,4,6-pentagalloyl-beta-D-glucopyranose isolated from geranium (Pelargonium inquinans Ait). Archives of pharmacal research 20050901
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. Carcinogenesis 20050801
Beta-secretase (BACE1) inhibitors from Sanguisorbae Radix. Archives of pharmacal research 20050701
Green tea: Health benefits as cancer preventive for humans. Chemical record (New York, N.Y.) 20050101
Chemical identification of the sources of commercial Fructus Chebulae. Phytochemical analysis : PCA 20050101
In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds. Antiviral chemistry & chemotherapy 20050101
Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease. Bioorganic & medicinal chemistry letters 20041220
Quantitative examination of oxidized polyphenol-protein complexes. Journal of agricultural and food chemistry 20041006
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. Carcinogenesis 20040701
Characterization of soluble non-covalent complexes between bovine serum albumin and beta-1,2,3,4,6-penta-O-galloyl-D-glucopyranose by MALDI-TOF MS. Journal of agricultural and food chemistry 20040616
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. Cancer letters 20040510
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. International immunopharmacology 20040301
Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds. Chemistry & biodiversity 20040301
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. Archives of pharmacal research 20031001
Paeonianins A-E, new dimeric and monomeric ellagitannins from the fruits of Paeonia lactiflora. Journal of natural products 20030601
Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves. Phytochemistry 20030201
Inhibitory effects of the root cortex of Paeonia suffruticosa on interleukin-8 and macrophage chemoattractant protein-1 secretions in U937 cells. Journal of ethnopharmacology 20030101
Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir. Journal of Asian natural products research 20021201
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. Journal of natural products 20021201
Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves preferentially acylating hexa- and heptagalloylglucoses. Planta 20021101
Penta-O-galloyl-beta-D-glucose inhibits the invasion of mouse melanoma by suppressing metalloproteinase-9 through down-regulation of activator protein-1. European journal of pharmacology 20021025
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. Neuroscience letters 20020809
Inhibition of HIV-1 integrase by galloyl glucoses from Terminalia chebula and flavonol glycoside gallates from Euphorbia pekinensis. Planta medica 20020501
Respiratory syncytial virus infection induces matrix metalloproteinase-9 expression in epithelial cells. Archives of virology 20020101
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. Cancer letters 20011210
Gallotannin biosynthesis: beta-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry 20011101
Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. Journal of natural products 20010801
Ellagic acid formation from galloylglucoses by a crude enzyme of Cornus capitata adventitious roots. Bioscience, biotechnology, and biochemistry 20010801
Seasonal variation in the content of hydrolysable tannins in leaves of Betula pubescens. Phytochemistry 20010501
Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis. Chemical & pharmaceutical bulletin 20010401
Inhibitory effects of ellagi- and gallotannins on rat intestinal alpha-glucosidase complexes. Bioscience, biotechnology, and biochemistry 20010301
Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography--electrospray ionisation mass spectrometry. Phytochemical analysis : PCA 20010101
Induction of apoptosis by penta-O-galloyl-beta-D-glucose through activation of caspase-3 in human leukemia HL-60 cells. European journal of pharmacology 19990924
A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase. Journal of natural products 19980101
Sulfated pentagalloyl glucose (Y-ART-3) inhibits HIV replication and cytopathic effects in vitro, and reduces HIV infection in hu-PBL-SCID mice. Antiviral research 19960501
Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antiviral research 19920501
Properties