![1,2,3,4,6-pentakis[O-(3,4,5-trihydroxybenzoyl)]-D-glucopyranose](/Databaselist/images/loading.webp)
50678-27-8Relevant academic research and scientific papers
Preparation method of 1,2,3,4,6-O-pentagalloylglucose standard sample
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0038, (2017/12/05)
The invention discloses a preparation method of a 1,2,3,4,6-O-pentagalloylglucose standard sample. The method comprises the steps that after gallnuat sodium tannic acid is degraded by a methanol acetic acid solution, reduction vaporation is performed to remove an organic solvent, then, diethyl ether and ethyl acetate are used for extraction, ethyl acetate is subjected to partial reduction vaporization to remove an organic solvent, and freeze drying is performed to obtain a crude 1,2,3,4,6-O-pentagalloylglucose product; then, methyl alcohol is used for dissolution, chromatographic separation is performed through sephadex chromatographic columns, the elution portion of 70% acetone is collected, reduction vaporization is performed to remove acetone, a water phase is subjected to freeze drying to obtain the 1,2,3,4,6-O-pentagalloylglucose standard sample. The 1,2,3,4,6-O-pentagalloylglucose standard sample obtained through the method is good in homogeneity, accurate in measurement size and good in stability, and therefore the high-quality standard sample is provided for performing detection, quantification and the like on the content of 1,2,3,4,6-O-pentagalloylglucose.
1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) analogs: Design, synthesis, anti-tumor and anti-oxidant activities
Shaikh, Qurat-Ul-Ain,Yang, Meiting,Memon, Khadim Hussain,Lateef, Mehreen,Na, Du,Wan, Shengbiao,Eric, Deslandes,Zhang, Lijuan,Jiang, Tao
, p. 72 - 81 (2016/05/24)
1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) 12 has been reported for its antioxidant activities, where the free OH groups in PGG seem to be critical for activities. To explore PGG-based compounds as chemotherapeutic agents and to analyze the contribution of specific OH groups in PGG for anti-cancer activities, we designed and synthesized a series of 27 benzoic and cinnamic acid analogs of PGG. These analogs were tested for cytotoxicities against two human lung (A549 and H1299) and two human colon (HCT116 and HT29) cancer cell lines. Compound 12 (PGG) had highest cytotoxicities against HCT116 and A549 cells with IC50 of 1.61 μM and 3.02 μM, respectively. In contrast, the compound 16 (1,2,3,4,6-pentakis[-O-(4-hydroxy-3-methoxybenzoyl)]-α,β-D-glucopyranose, PVG) was most effective at killing HT29 and H1299 cells with IC50 of 1.76 μM and 3.65 μM, respectively, indicating the mutual contribution of m-methoxy and p-hydroxy groups to the observed cytotoxicities. Moreover, cinnamic acid analogs were less active than the benzoic acid analogs evidenced by higher IC50 values. Furthermore, in cinnamic acid analogs the hydrogenation of double bond to saturated 2-C side chain enhance the cytotoxicities in all four cell lines. Compounds also possess good anti-oxidant and reducing activities. Compound 12 and 26 show the highest antioxidant and reducing activities.
Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
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Page/Page column 61, (2015/09/22)
The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.
Gallotannins and Tannic Acid: First Chemical Syntheses and in Vitro Inhibitory Activity on Alzheimer's Amyloid β-Peptide Aggregation
Sylla, Tahiri,Pouységu, Laurent,Dacosta, Grégory,Deffieux, Denis,Monti, Jean-Pierre,Quideau, Stéphane
supporting information, p. 8217 - 8221 (2015/07/07)
The screening of natural products in the search for new lead compounds against Alzheimer's disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β-amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using "tannic acid", a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins, a hexagalloylglucopyranose and a decagalloylated compound whose structure is commonly used to depict "tannic acid", are now described. These depsidic gallotannins and simpler galloylated glucose derivatives all inhibit amyloid β-peptide (Aβ) aggregation invitro, and monogalloylated α-glucogallin and a natural β-hexagalloylglucose are shown to be the strongest inhibitors.
Designing allosteric inhibitors of factor XIa. Lessons from the interactions of sulfated pentagalloylglucopyranosides
Al-Horani, Rami A.,Desai, Umesh R.
supporting information, p. 4805 - 4818 (2014/07/07)
We recently introduced sulfated pentagalloylglucopyranoside (SPGG) as an allosteric inhibitor of factor XIa (FXIa) (Al-Horani et al., J. Med Chem. 2013, 56, 867-878). To better understand the SPGG-FXIa interaction, we utilized eight SPGG variants and a range of biochemical techniques. The results reveal that SPGG's sulfation level moderately affected FXIa inhibition potency and selectivity over thrombin and factor Xa. Variation in the anomeric configuration did not affect potency. Interestingly, zymogen factor XI bound SPGG with high affinity, suggesting its possible use as an antidote. Acrylamide quenching experiments suggested that SPGG induced significant conformational changes in the active site of FXIa. Inhibition studies in the presence of heparin showed marginal competition with highly sulfated SPGG variants but robust competition with less sulfated variants. Resolution of energetic contributions revealed that nonionic forces contribute nearly 87% of binding energy suggesting a strong possibility of specific interaction. Overall, the results indicate that SPGG may recognize more than one anion-binding, allosteric site on FXIa. An SPGG molecule containing approximately 10 sulfate groups on positions 2 through 6 of the pentagalloylglucopyranosyl scaffold may be the optimal FXIa inhibitor for further preclinical studies.
Synthesis and antitumor activity of ellagic acid peracetate
Ren, Yulin,Still, Patrick C.,Kinghorn, A. Douglas,Wei, Min,Chen, Xiaozhuo,Himmeldirk, Klaus,Yuan, Shunzong,Deng, Youcai,Yu, Jianhua
supporting information, p. 631 - 636,6 (2020/08/31)
Ellagic acid (1) was synthesized for the first time from methyl gallate through α-pentagalloylglucose (α-PGG), and ellagic acid peracetate (3,4,3′,4′-tetra-O-acetylellagic acid, 2) was derived from 1 by acetylation. Oral administration of 2 suppressed melanoma growth significantly in C7BL/6 immunocompetent mice without having any effect on natural killer (NK) cell activity. Comparison of the immunoenhancing activities of 1 and 2 indicated that the latter compound increased white blood cell quantities in peripheral blood and immune cells enriched from the bone marrow and liver of mice. Therefore, both the antitumor efficacy and the immunity enhancement by 2 were greater than those by 1. In addition, on oral administration, neither 1 nor 2 resulted in whole body, liver, or spleen weight changes of normal, tumor-free mice, indicating that these compounds are potentially nontoxic to mice. It was shown that ellagic acid peracetate (2) inhibits B16 melanoma cell growth in vitro and induces B16 cell apoptosis, corresponding to BCL-2 down-regulation. Collectively, the present data imply that 2 can suppress tumor growth by enhancing mouse immunity and inducing tumor cell apoptosis without apparent side effects.
Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos
Tamura, Satoru,Yang, Gang-Ming,Yasueda, Natsuko,Matsuura, Yoshiharu,Komoda, Yasumasa,Murakami, Nobutoshi
scheme or table, p. 1598 - 1600 (2010/06/16)
By use of the model virus, expressing the HCV envelope proteins E1 and E2, bioassay guided separation of the MeOH extract from Rosa rugosa Thunb. disclosed tellimagrandin I (1) together with eugeniin (2) and casuarictin (3) as the potent HCV invasion inhibitors. Furthermore, structure-activity relationship analysis of some relative tannins including the synthesized analogs elucidated the partial structures crucial for potent activity of 1.
Plasminogen Activator Inhibitor-1 Inhibitors And Methods Of Use Thereof To Modulate Lipid Metabolism
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, (2009/01/23)
The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.
Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues
Ren, Yulin,Himmeldirk, Klaus,Chen, Xiaozhuo
, p. 2829 - 2837 (2007/10/03)
The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the α- and β-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-α-D-glucopyranose (43) and tetra-O-galloyl-α- D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl- α-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.
