1,2,3,4,6-O-Pentagalloylglucose

Details:

Chemical Properties of 1,2,3,4,6-O-Pentagalloylglucose

Cas No.	14937-32-7
PubChem ID	65238	Appearance	Off-white -beige powder
Formula	C41H32O26	M.Wt	940.68
Type of Compound	Phenols	Storage	Desiccate at -20°C
Synonyms	Penta-O-galloyl-β-D-glucose
Solubility	DMSO : 50 mg/mL (53.15 mM; Need ultrasonic) H2O : 6 mg/mL (6.38 mM; Need ultrasonic and warming)
Chemical Name	[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
SMILES	C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
Standard InChIKey	QJYNZEYHSMRWBK-NIKIMHBISA-N
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 1,2,3,4,6-O-Pentagalloylglucose

1 Canarium sp. 2 Carpinus sp. 3 Cornus sp. 4 Elaeocarpus sp. 5 Euphorbia sp. 6 Haemotoxylum sp. 7 Hamamelis sp. 8 Paeonia sp. 9 Pelargonium sp. 10 Picrorhiza sp. 11 Pistacia sp. 12 Primula sp. 13 Punica sp. 14 Quercus sp. 15 Rhus sp. 16 Sanguisorba sp. 17 Terminalia sp.

Biological Activity of 1,2,3,4,6-O-Pentagalloylglucose

Description	1,2,3,4,6-O-Pentagalloylglucose(PGG) has antimutagenic, anti-proliferative, anti-invasive,vasodilatory, anti-inflammatory, anti-parasitic, anti-HBV, and antioxidant activities. PGG may serve as a model for the development of new types of anti-diabetic and anti-metabolic syndrome therapeutics. PGG dilates vascular smooth muscle and suppresses the vascular inflammatory process via endothelium-dependent nitric oxide (NO)/cGMP signaling; it also has inhibition of inducible NO synthase and cyclooxygenase-2 activity.
Targets	PARP | TNF-α | p65 | NF-kB | COX | NOS | PGE | NO | GLUT | PI3K | Akt | HBV | Antifection
In vitro	Study of antimutagenic and antioxidant activities of gallic acid and 1,2,3,4,6-pentagalloylglucose from Pistacia lentiscus. Confirmation by microarray expression profiling.[Pubmed: 17129579 ] Chem.Biol.Interact., 2007, 165(1):1-13. In vitro antioxidant and antimutagenic activities of two polyphenols isolated from the fruits of Pistacia lentiscus was assessed. METHODS AND RESULTS: Antioxidant activity was determined by the ability of each compound to scavenge the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH*), to inhibit xanthine oxidase and to inhibit the lipid peroxidation induced by H(2)O(2) in K562 cell line. Antimutagenic activity was assayed with SOS chromotest using Escherichia coli PQ37 as tester strain and Comet assay using K562 cell line. 1,2,3,4,6-Pentagalloylglucose(1,2,3,4,6-O-Pentagalloylglucose) was found to be more effective to scavenge DPPH* radical and protect against lipid peroxidation. Moreover, these two compounds induced an inhibitory activity against nifuroxazide and aflatoxin B1 mutagenicity. The protective effect exhibited by these molecules was also determined by analysis of gene expression as response to an oxidative stress. For this purpose, we used a cDNA-microarray containing 82 genes related to cell defense, essentially represented by antioxidant and DNA repair proteins. CONCLUSIONS: We found that 1,2,3,4,6-pentagalloylglucose induced a decrease in the expression of 11 transcripts related to antioxidant enzymes family (GPX1, TXN, AOE372, SHC1 and SEPW1) and DNA repair (POLD1, APEX, POLD2, MPG, PARP and XRCC5). The use of Gallic acid, induced expression of TXN, TXNRD1, AOE372, GSS (antioxidant enzymes) and LIG4, POLD2, MPG, GADD45A, PCNA, RPA2, DDIT3, HMOX2, XPA, TDG, ERCC1 and GTF2H1 (DNA repair) as well as the repression of GPX1, SEPW1, POLD1 and SHC1 gene expression. Anti-trypanosomal activity of 1,2,3,4,6-penta-O-galloyl-β -D-glucose isolated from Plectranthus barbatus Andrews (Lamiaceae).[Reference: WebLink] Química Nova, 2012, 35(11):2229-332. MeOH extract from the leaves of Plectranthus barbatus Andrews (Lamiaceae), showed in vitro anti-trypanosomal activity. METHODS AND RESULTS: The bioassay-guided fractionation resulted in the isolation of a gallic acid derivative, identified as 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), after thorough NMR and MS spectral analysis. Finally, this compound was tested against trypomastigote forms of T. cruzi and displayed an EC50 value of 67 μM, at least 6.6-fold more effective than the standard drug benznidazole. CONCLUSIONS: This is the first occurrence of PGG in the Plectranthus genus and the first anti-parasitic activity described for PGG in the literature.
In vivo	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.[Pubmed: 16253226 ] Eur. J.Pharmacol., 2005, 524(1-3):111-9. Vasorelaxant and anti-inflammatory effects of a 1,2,3,4,6-penta-O-galloyl-beta-d-glucose (1,2,3,4,6-O-Pentagalloylglucose,PGG) isolated from the root barks of Paeonia suffruticosa and possible mechanisms responsible were investigated. METHODS AND RESULTS: PGG induced a concentration-dependent relaxation of the phenylephrine-precontracted rat aorta. This effect disappeared with the removal of functional endothelium. Pretreatment of the aortic tissues with either N(G)-nitro-L-arginine methyl ester (L-NAME) or 1H-[1,2,4]-oxadiazole-[4,3-alpha]-quinoxalin-1-one (ODQ) inhibited the relaxation induced by PGG. Incubation of human umbilical vein endothelial cells (HUVECs) or carotid arteries isolated from rats with PGG increased the production of cGMP in a dose-dependent manner, but this effect was blocked by pretreatment with L-NAME and ODQ, respectively. PGG treatment attenuated tumor necrosis factor-alpha (TNF-alpha)-induced nuclear factor-kappaB (NF-kappaB) p65 translocation in human umbilical vein endothelial cells. In addition, PGG suppressed the expression levels of adhesion molecules including intracellular cell adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) induced by TNF-alpha. TNF-alpha-induced monocyte chemoattractant protein-1 (MCP-1) expression was also attenuated by addition of PGG. PGG treatment inhibited cellular adhesion of U937 cells onto human umbilical vein endothelial cells induced by TNF-alpha. CONCLUSIONS: Taken together, the present study suggests that PGG dilates vascular smooth muscle and suppresses the vascular inflammatory process via endothelium-dependent nitric oxide (NO)/cGMP signaling.

Protocol of 1,2,3,4,6-O-Pentagalloylglucose

Kinase Assay

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.[Pubmed: 14609132] Arch Pharm Res. 2003 Oct;26(10):832-9. Activated macrophages express inducible isoforms of nitric oxide synthase (iNOS) and cyclooxygenase (COX-2), and produce excessive amounts of nitric oxide (NO) and prostaglandin E2 (PGE2), which play key roles in the processes of inflammation and carcinogenesis. The root of Paeonia lactiflora Pall., and the root cortex of Paeonia suffruticosa Andr., are important Chinese crude drugs used in many traditional prescriptions. 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (1,2,3,4,6-O-Pentagalloylglucose,PGG) is a major bioactive constituent of both crude drugs. PGG has been shown to possess potent anti-oxidant, anti-mutagenic, anti-proliferative and anti-invasive effects. In this study, we examined the inhibitory effects of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) isolated from the root of Paeonia lactiflora Pall. on the COX-2 and iNOS activity in LPS-activated Raw 264.7 cells, COX-1 in HEL cells. To investigate the structure-activity relationships of gallate and gallic acid for the inhibition of iNOS and COX-2 activity, we also examined (-)-epigallocatechin gallate (EGCG), gallic acid, and gallacetophenone. The results of the present study indicated that PGG, EGCG, and gallacetophenone treatment except gallic acid significantly inhibited LPS-induced NO production in LPS-activated macrophages. All of the four compounds significantly inhibited COX-2 activity in LPS-activated macrophages. Among the four compounds examined, PGG revealed the most potent in both iNOS (IC50 approximately 18 microg/mL) and COX-2 inhibitory activity (PGE2: IC50 approximately 8 microg/mL and PGD2: IC50 approximately 12 microg/mL), respectively. Although further studies are needed to elucidate the molecular mechanisms and structure-activity relationship by which PGG exerts its inhibitory actions, our results suggest that PGG might be a candidate for developing anti-inflammatory and cancer chemopreventive agents.

Cell Research

In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus.[Pubmed: 17015965] 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.[Pubmed: 16137651 ] Biochem Biophys Res Commun. 2005 Oct 21;336(2):430-7. Insulin mimetics from natural sources are potential therapeutics that can act alone or supplement insulin and other anti-diabetic drugs in the prevention and treatment of diabetes. We recently reported the insulin-like glucose transport stimulatory activity of tannic acid (TA) in 3T3-L1 adipocytes. METHODS AND RESULTS: In this study, we find that chemically synthesized 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (1,2,3,4,6-O-Pentagalloylglucose,beta-PGG), one of the components of TA, as well as its natural anomer alpha-PGG possess activity. Mechanistic studies in adipocytes with alpha-PGG, the more potent of the two anomers, reveal that inhibitors that block the insulin-mediated glucose transport, including one that inhibits the insulin receptor (IR), also completely abolish the glucose transport activated by alpha-PGG. In addition, alpha-PGG induces phosphorylation of the IR and Akt, activates PI 3-kinase, and stimulates membrane translocation of GLUT 4. Receptor binding studies indicate that alpha-PGG binds to the IR and affects the binding between insulin and IR by reducing the maximum binding of insulin to IR without significantly altering the binding affinity of insulin to IR. Western blotting analysis of the products of a cross-linking reaction suggests that alpha-PGG may bind to IR at a site located on the alpha-subunit of the receptor. Animal studies demonstrate that PGG reduces blood glucose levels and improves glucose tolerance in diabetic and obese animals. CONCLUSIONS: Our results suggest that PGG may serve as a model for the development of new types of anti-diabetic and anti-metabolic syndrome therapeutics. Biol Pharm Bull. 2006 Oct;29(10):2131-4. This study examined the antiviral activity of the root of Paeonia lactiflora PALL. METHODS AND RESULTS: Among the solvent fractions of the crude drug, the ethyl acetate fraction showed anti-hepatitis B virus (HBV) activity (IC50, 8.1 microg/ml) in an HBV-producing HepG2.2.15 cell culture system. The active anti-HBV principle was isolated and identified as 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (1,2,3,4,6-O-Pentagalloylglucose,PGG) from the crude drug by activity-guided fractionation. PGG isolated from P. lactiflora was examined for the inhibition of HBV multiplication by measurement of HBV DNA and hepatitis B surface antigen (HBsAg) levels in the extracellular medium of HepG2.2.15 cells after 8-d treatment. PGG decreased the level of extracellular HBV (IC50, 1.0 microg/ml) in a dose-dependent manner. PGG also reduced the HBsAg level by 25% at a concentration of 4 microg/ml. The gallate structure of PGG may play a critical role in the inhibition of anti-HBV activity. CONCLUSIONS: These results suggest that PGG could be a candidate for developing an anti-HBV agent.

Preparing Stock Solutions of 1,2,3,4,6-O-Pentagalloylglucose

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	1.0631 mL	5.3153 mL	10.6306 mL	21.2612 mL	26.5765 mL
5 mM	0.2126 mL	1.0631 mL	2.1261 mL	4.2522 mL	5.3153 mL
10 mM	0.1063 mL	0.5315 mL	1.0631 mL	2.1261 mL	2.6577 mL
50 mM	0.0213 mL	0.1063 mL	0.2126 mL	0.4252 mL	0.5315 mL
100 mM	0.0106 mL	0.0532 mL	0.1063 mL	0.2126 mL	0.2658 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

References on 1,2,3,4,6-O-Pentagalloylglucose

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.[Pubmed:16253226]

Eur J Pharmacol. 2005 Nov 7;524(1-3):111-9.

Vasorelaxant and anti-inflammatory effects of a 1,2,3,4,6-penta-O-galloyl-beta-d-glucose (PGG) isolated from the root barks of Paeonia suffruticosa and possible mechanisms responsible were investigated. PGG induced a concentration-dependent relaxation of the phenylephrine-precontracted rat aorta. This effect disappeared with the removal of functional endothelium. Pretreatment of the aortic tissues with either N(G)-nitro-L-arginine methyl ester (L-NAME) or 1H-[1,2,4]-oxadiazole-[4,3-alpha]-quinoxalin-1-one (ODQ) inhibited the relaxation induced by PGG. Incubation of human umbilical vein endothelial cells (HUVECs) or carotid arteries isolated from rats with PGG increased the production of cGMP in a dose-dependent manner, but this effect was blocked by pretreatment with L-NAME and ODQ, respectively. PGG treatment attenuated tumor necrosis factor-alpha (TNF-alpha)-induced nuclear factor-kappaB (NF-kappaB) p65 translocation in human umbilical vein endothelial cells. In addition, PGG suppressed the expression levels of adhesion molecules including intracellular cell adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) induced by TNF-alpha. TNF-alpha-induced monocyte chemoattractant protein-1 (MCP-1) expression was also attenuated by addition of PGG. PGG treatment inhibited cellular adhesion of U937 cells onto human umbilical vein endothelial cells induced by TNF-alpha. Taken together, the present study suggests that PGG dilates vascular smooth muscle and suppresses the vascular inflammatory process via endothelium-dependent nitric oxide (NO)/cGMP signaling.

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.[Pubmed:14609132]

Arch Pharm Res. 2003 Oct;26(10):832-9.

Activated macrophages express inducible isoforms of nitric oxide synthase (iNOS) and cyclooxygenase (COX-2), and produce excessive amounts of nitric oxide (NO) and prostaglandin E2 (PGE2), which play key roles in the processes of inflammation and carcinogenesis. The root of Paeonia lactiflora Pall., and the root cortex of Paeonia suffruticosa Andr., are important Chinese crude drugs used in many traditional prescriptions. 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) is a major bioactive constituent of both crude drugs. PGG has been shown to possess potent anti-oxidant, anti-mutagenic, anti-proliferative and anti-invasive effects. In this study, we examined the inhibitory effects of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) isolated from the root of Paeonia lactiflora Pall. on the COX-2 and iNOS activity in LPS-activated Raw 264.7 cells, COX-1 in HEL cells. To investigate the structure-activity relationships of gallate and gallic acid for the inhibition of iNOS and COX-2 activity, we also examined (-)-epigallocatechin gallate (EGCG), gallic acid, and gallacetophenone. The results of the present study indicated that PGG, EGCG, and gallacetophenone treatment except gallic acid significantly inhibited LPS-induced NO production in LPS-activated macrophages. All of the four compounds significantly inhibited COX-2 activity in LPS-activated macrophages. Among the four compounds examined, PGG revealed the most potent in both iNOS (IC50 approximately 18 microg/mL) and COX-2 inhibitory activity (PGE2: IC50 approximately 8 microg/mL and PGD2: IC50 approximately 12 microg/mL), respectively. Although further studies are needed to elucidate the molecular mechanisms and structure-activity relationship by which PGG exerts its inhibitory actions, our results suggest that PGG might be a candidate for developing anti-inflammatory and cancer chemopreventive agents.

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.[Pubmed:16137651]

Biochem Biophys Res Commun. 2005 Oct 21;336(2):430-7.

Insulin mimetics from natural sources are potential therapeutics that can act alone or supplement insulin and other anti-diabetic drugs in the prevention and treatment of diabetes. We recently reported the insulin-like glucose transport stimulatory activity of tannic acid (TA) in 3T3-L1 adipocytes. In this study, we find that chemically synthesized 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (beta-PGG), one of the components of TA, as well as its natural anomer alpha-PGG possess activity. Mechanistic studies in adipocytes with alpha-PGG, the more potent of the two anomers, reveal that inhibitors that block the insulin-mediated glucose transport, including one that inhibits the insulin receptor (IR), also completely abolish the glucose transport activated by alpha-PGG. In addition, alpha-PGG induces phosphorylation of the IR and Akt, activates PI 3-kinase, and stimulates membrane translocation of GLUT 4. Receptor binding studies indicate that alpha-PGG binds to the IR and affects the binding between insulin and IR by reducing the maximum binding of insulin to IR without significantly altering the binding affinity of insulin to IR. Western blotting analysis of the products of a cross-linking reaction suggests that alpha-PGG may bind to IR at a site located on the alpha-subunit of the receptor. Animal studies demonstrate that PGG reduces blood glucose levels and improves glucose tolerance in diabetic and obese animals. Our results suggest that PGG may serve as a model for the development of new types of anti-diabetic and anti-metabolic syndrome therapeutics.

In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus.[Pubmed:17015965]

Biol Pharm Bull. 2006 Oct;29(10):2131-4.

This study examined the antiviral activity of the root of Paeonia lactiflora PALL. Among the solvent fractions of the crude drug, the ethyl acetate fraction showed anti-hepatitis B virus (HBV) activity (IC50, 8.1 microg/ml) in an HBV-producing HepG2.2.15 cell culture system. The active anti-HBV principle was isolated and identified as 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) from the crude drug by activity-guided fractionation. PGG isolated from P. lactiflora was examined for the inhibition of HBV multiplication by measurement of HBV DNA and hepatitis B surface antigen (HBsAg) levels in the extracellular medium of HepG2.2.15 cells after 8-d treatment. PGG decreased the level of extracellular HBV (IC50, 1.0 microg/ml) in a dose-dependent manner. PGG also reduced the HBsAg level by 25% at a concentration of 4 microg/ml. The gallate structure of PGG may play a critical role in the inhibition of anti-HBV activity. These results suggest that PGG could be a candidate for developing an anti-HBV agent.

Study of antimutagenic and antioxidant activities of gallic acid and 1,2,3,4,6-pentagalloylglucose from Pistacia lentiscus. Confirmation by microarray expression profiling.[Pubmed:17129579]

Chem Biol Interact. 2007 Jan 5;165(1):1-13.

In vitro antioxidant and antimutagenic activities of two polyphenols isolated from the fruits of Pistacia lentiscus was assessed. Antioxidant activity was determined by the ability of each compound to scavenge the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH*), to inhibit xanthine oxidase and to inhibit the lipid peroxidation induced by H(2)O(2) in K562 cell line. Antimutagenic activity was assayed with SOS chromotest using Escherichia coli PQ37 as tester strain and Comet assay using K562 cell line. 1,2,3,4,6-Pentagalloylglucose was found to be more effective to scavenge DPPH* radical and protect against lipid peroxidation. Moreover, these two compounds induced an inhibitory activity against nifuroxazide and aflatoxin B1 mutagenicity. The protective effect exhibited by these molecules was also determined by analysis of gene expression as response to an oxidative stress. For this purpose, we used a cDNA-microarray containing 82 genes related to cell defense, essentially represented by antioxidant and DNA repair proteins. We found that 1,2,3,4,6-pentagalloylglucose induced a decrease in the expression of 11 transcripts related to antioxidant enzymes family (GPX1, TXN, AOE372, SHC1 and SEPW1) and DNA repair (POLD1, APEX, POLD2, MPG, PARP and XRCC5). The use of Gallic acid, induced expression of TXN, TXNRD1, AOE372, GSS (antioxidant enzymes) and LIG4, POLD2, MPG, GADD45A, PCNA, RPA2, DDIT3, HMOX2, XPA, TDG, ERCC1 and GTF2H1 (DNA repair) as well as the repression of GPX1, SEPW1, POLD1 and SHC1 gene expression.

Description

Pentagalloylglucose (Penta-O-galloyl-β-D-glucose) is a gallotannin isolated from various plants. It suppressed interleukin (IL)-4 induced signal pathway in B cell, and inhibited IgE production partially caused by increasing a population of Treg cells in conjunction with Treg-inducing factors. Pentagalloylglucose possesses significant anti-rabies virus (RABV) activity.

Keywords:

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