tannins and corilagin

Terminalia bellirica (Gaertn.) Roxb. is one of the oldest medicinal herbs of India, Pakistan, Nepal, Bangladesh and Sri Lanka as well as South-East Asia. Its medicinal utility has been described in the different traditional medicinal systems, such as Ayurveda, Unani, Siddha, and traditional Chinese medicine.. The present study is aimed at providing a comprehensive overview on the traditional medicinal use, major phytoconstituents, biological and pharmacological activities and related mechanisms of actions and clinical studies of T. bellirica. Another objective is to describe current limitations and future direction of T. bellirica-related research.. PubMed, ScienceDirect, Scopus, Cochrane Library, and EBOSCO host databases were selected to explore literature published between 1980 and 2020 (till March). Keywords used in various combinations comprised of Terminalia bellirica, phytoconstituents, health effects, pharmacological activities, molecular targets, in vitro, in vivo, clinical studies, and disease prevention.. A broad spectrum in vitro and in vivo studies suggested various biological and pharmacological effects, including antioxidant, anti-inflammatory, immunomodulatory, antimicrobial, hepatoprotective, renoprotective, antidiabetic, anti-hyperlipidemic, and anticancer activities. Diverse bioactivities of T. bellirica have been ascribed to the presence of many bioactive phytochemicals, such as glucoside, tannins, gallic acid, corilagin, ellagic acid, ethyl gallate, galloyl glucose, chebulagic acid, and arjunolic acid.. Preclinical and clinical studies have suggested that T. bellirica plant and its phytoconstituents have immense potential for prevention and treatment of various diseases. Additional in vivo studies and clinical trials are warranted to realize the complete medicinal attributes of this plant.

Topics: Animals; Antioxidants; Gallic Acid; Glucosides; Humans; Hydrolyzable Tannins; Medicine, Ayurvedic; Phytochemicals; Plant Extracts; Plants, Medicinal; Tannins; Terminalia; Triterpenes

The overall impact of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) on our society is unprecedented. The identification of small natural ligands that could prevent the entry and/or replication of the coronavirus remains a pertinent approach to fight the coronavirus disease (COVID-19) pandemic. Previously, we showed that the phenolic compounds corilagin and 1,3,6-tri-O-galloyl-β-D-glucose (TGG) inhibit the interaction between the SARS-CoV-2 spike protein receptor binding domain (RBD) and angiotensin-converting enzyme 2 (ACE2), the SARS-CoV-2 target receptor on the cell membrane of the host organism. Building on these promising results, we now assess the effects of these phenolic ligands on two other crucial targets involved in SARS-CoV-2 cell entry and replication, respectively: transmembrane protease serine 2 (TMPRSS2) and 3-chymotrypsin like protease (3CLpro) inhibitors. Since corilagin, TGG, and tannic acid (TA) share many physicochemical and structural properties, we investigate the binding of TA to these targets. In this work, a combination of experimental methods (biochemical inhibition assays, surface plasmon resonance, and quartz crystal microbalance with dissipation monitoring) confirms the potential role of TA in the prevention of SARS-CoV-2 infectivity through the inhibition of extracellular RBD/ACE2 interactions and TMPRSS2 and 3CLpro activity. Moreover, molecular docking prediction followed by dynamic simulation and molecular mechanics Poisson-Boltzmann surface area (MMPBSA) free energy calculation also shows that TA binds to RBD, TMPRSS2, and 3CLpro with higher affinities than TGG and corilagin. Overall, these results suggest that naturally occurring TA is a promising candidate to prevent and inhibit the infectivity of SARS-CoV-2.

Topics: Algorithms; Angiotensin-Converting Enzyme 2; Coronavirus 3C Proteases; COVID-19; Glucosides; Humans; Hydrolyzable Tannins; Kinetics; Molecular Docking Simulation; Pandemics; Protein Binding; SARS-CoV-2; Serine Endopeptidases; Spike Glycoprotein, Coronavirus; Surface Plasmon Resonance; Tannins; Virus Internalization

Drug discovery from complex mixture like Chinese herbs is a challenge and extensive false positives make the obtainment of specific bioactive compounds difficult. In the present study, a novel sample preparation method was proposed to rapidly reveal the specific bioactive compounds from complex mixtures using α-glucosidase as a case. Firstly, aqueous and methanol extracts of 500 traditional Chinese medicines were carried out with the aim of finding new sources of α-glucosidase inhibitors. As a result, the extracts of fruit of Terminalia chebula (FTC), flowers of Rosa rugosa (FRR) and Eugenia caryophyllata (FEC) as well as husk of Punica granatum (HPG) showed high inhibition on α-glucosidase. On-line liquid chromatography-diode array detection-tandem mass spectrometry and biochemical detection (HPLC-DAD-MS/MS-BCD) was performed to rapidly screen and characterize α-glucosidase inhibitors in these four extracts. After tentative identification, most of compounds with inhibitory activity in the investigated crude extracts were found to be tannins commonly recognized as non-specific enzyme inhibitors in vitro. Subsequently, the four extracts were treated with gelatin to improve specificity of the on-line system. Finally, two compounds with specific α-glucosidase inhibition were identified as corilagin and ellagic acid. The developed method could discover specific α-glucosidase inhibitors in complex mixtures such as plant extracts, which could also be used for discovery of specific inhibitors of other enzymes.

Topics: alpha-Glucosidases; Chromatography, High Pressure Liquid; Drug Discovery; Ellagic Acid; Enzyme Inhibitors; Flowers; Gelatin; Glucosides; Hydrolyzable Tannins; Kinetics; Lythraceae; Medicine, Chinese Traditional; Plant Extracts; Plant Leaves; Plant Preparations; Reproducibility of Results; Rosa; Syzygium; Tandem Mass Spectrometry; Tannins; Terminalia

Punica granatum (family: Lythraceae) is mainly found in Iran, which is considered to be its primary centre of origin. Studies on pomegranate peel have revealed antioxidant, anti-inflammatory, anti- angiogenesis activities, with prevention of premature aging and reducing inflammation. In addition to this it is also useful in treating various diseases like diabetes, maintaining blood pressure and treatment of neoplasms such as prostate and breast cancer.. In this study we identified anti-cancer targets of active compounds like corilagin (tannins), quercetin (flavonoids) and pseudopelletierine (alkaloids) present in pomegranate peel by employing dual reverse screening and binding analysis.. The potent targets of the pomegranate peel were annotated by the PharmMapper and ReverseScreen 3D, then compared with targets identified from different Bioassay databases (NPACT and HIT's). Docking was then further employed using AutoDock pyrx and validated through discovery studio for studying molecular interactions.. A number of potent anti-cancerous targets were attained from the PharmMapper server according to their fit score and from ReverseScreen 3D server according to decreasing 3D scores.. The identified targets now need to be further validated through in vitro and in vivo studies.

Topics: Alkaloids; Antineoplastic Agents; Computer Simulation; Drug Discovery; Flavonoids; Fruit; Glucosides; Humans; Hydrolyzable Tannins; Lythraceae; Molecular Docking Simulation; Molecular Targeted Therapy; Neoplasms; Piperidines; Quercetin; Tannins

Corilagin is a member of polyphenolic tannins. Its antimicrobial activity and action mechanism against Escherichia coli, Staphylococcus aureus and Candida albicans were investigated through membrane permeability. Crystal violet staining determination, outer membrane (OM) and inner membrane (IM) permeability, sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) and atomic force microscopy (AFM) were used as methods for our investigation. The minimum inhibitory concentrations were 62.5, 31.25 and 62.5 µg/mL for E. coli, S. aureus and C. albicans, respectively. Crystal violet results and SDS-PAGE of supernatant proteins showed that corilagin dose-dependently affected membrane permeability of E. coli and C. albicans but not of S. aureus. OM and IM permeability assays revealed comparable results for E. coli. By using AFM, we demonstrated extensive cell surface alterations of corilagin-treated E. coli and C. albicans. SDS-PAGE of precipitated proteins revealed possible targets of corilagin, i.e. Fib, Sae R, Sar S in S. aureus and Tye 7p in C. albicans. In conclusion, corilagin inhibited the growth of E. coli and C. albicans by disrupting their membrane permeability and that of S. aureus by acting on Fib, Sae R and Sar S but not on membrane integrity.

Topics: Candida albicans; Cell Membrane Permeability; Escherichia coli; Gentian Violet; Glucosides; Hydrolyzable Tannins; Microbial Sensitivity Tests; Microscopy, Atomic Force; Staphylococcus aureus; Tannins

The antioxidant and hepatoprotective actions of Terminalia catappa L. collected from Okinawa Island were evaluated in vitro and in vivo using leaves extract and isolated antioxidants. A water extract of the leaves of T. catappa showed a strong radical scavenging action for 1,1-diphenyl-2-picrylhydrazyl and superoxide (O(2)(.-)) anion. Chebulagic acid and corilagin were isolated as the active components from T. catappa. Both antioxidants showed a strong scavenging action for O(2)(.-) and peroxyl radicals and also inhibited reactive oxygen species production from leukocytes stimulated by phorbol-12-myristate acetate. Galactosamine (GalN, 600 mg/kg, s.c.,) and lipopolysaccharide (LPS, 0.5 microg/kg, i.p.)-induced hepatotoxicity of rats as seen by an elevation of serum alanine aminotransferase, aspartate aminotransferase and glutathione S-transferase (GST) activities was significantly reduced when the herb extract or corilagin was given intraperitoneally to rats prior to GalN/LPS treatment. Increase of free radical formation and lipid peroxidation in mitochondria caused by GalN/LPS treatment were also decreased by pretreatment with the herb/corilagin. In addition, apoptotic events such as DNA fragmentation and the increase in caspase-3 activity in the liver observed with GalN/LPS treatment were prevented by the pretreatment with the herb/corilagin. These results show that the extract of T. catappa and its antioxidant, corilagin are protective against GalN/LPS-induced liver injury through suppression of oxidative stress and apoptosis.

Topics: Animals; Antioxidants; Chemical and Drug Induced Liver Injury; Free Radicals; Galactosamine; Glucosides; Hydrolyzable Tannins; Lipopolysaccharides; Liver; Male; Phytotherapy; Plant Extracts; Plant Leaves; Protective Agents; Rats; Rats, Sprague-Dawley; Tannins; Terminalia

Substantial progress has been made in research on natural products which effectively inhibit HIV-1 replication. Many active compounds were isolated from traditionally used medicinal plants including Phyllanthus species. This study shows that aqueous as well as alcohol-based Phyllanthus amarus extracts potently inhibit HIV-1 replication in HeLa CD4(+) cells with 50% effective concentration (EC(50)) values ranging from 0.9 to 7.6 microg/ml. A gallotannin enriched fraction showed enhanced activity (0.4 microg/ml), and the purified gallotannins geraniin and corilagin were most active (0.24 microg/ml). HIV-1 replication was also blocked in CD4(+) lymphoid cells with comparable EC(50) values. Applying a cell-based internalization assay, we could demonstrate 70-75% inhibition of virus uptake at concentrations of 2.5 microg/ml for the water/alcohol extract and geraniin. In addition, a concentration-dependent inhibition of HIV-1 reverse transcriptase (RT) could be demonstrated in vitro. The 50% inhibitory concentration (IC(50)) values varied from 1.8 to 14.6 microg/ml. The ability to inhibit replication of a variety of RT inhibitor-resistant HIV-1 strains points to the potential of P. amarus extracts, as natural products, in the chemotherapy of HIV infections.

Topics: CD4 Antigens; Drug Resistance, Viral; Euphorbiaceae; Glucosides; HeLa Cells; HIV-1; HIV-2; Humans; Hydrolyzable Tannins; Plant Extracts; Plants, Medicinal; Reverse Transcriptase Inhibitors; Tannins; Tumor Cells, Cultured; Virus Replication

The success of green tea as a cancer preventive is based on evidence that green tea contains tannins and antioxidants, does not show toxicity in humans and has long traditional use in Asia. In the light of this, herbal medicines are now also attracting attention as potential sources of cancer preventive agents. Using the inhibition of TNF-alpha release assay, we studied Acer nikoense (Megusurino-ki in Japanese), one of the herbal medicines. The inhibitory activity of TNF-alpha release was found in the leaf extract rather than the bark extract, and the main active constituents were identified as geraniin and corilagin, which are present in another Japanese traditional herb, Geranium thunbergii (Genno-shoko). The IC50 values of TNF-alpha release inhibition were 43 microM for geraniin and 76 microM for corilagin, whereas that for (-)-epigallocatechin gallate (EGCG) was 26 microM. Treatment with geraniin prior to application of okadaic acid, a tumor promoter on mouse skin initiated with 7,12-dimethylbenz(a)anthracene, reduced the percentage of tumor-bearing mice from 80.0 to 40.0% and the average numbers of tumor per mouse from 3.8 to 1.1 in week 20. Thus, geraniin has slightly weaker inhibitory activity than EGCG. Since geraniin and corilagin have been well investigated as representative tannins, we discuss here the new possibility of classical herbal medicine in the development of preventive agents for cancer and other life-style related diseases.

Topics: 3T3 Cells; 9,10-Dimethyl-1,2-benzanthracene; Animals; Anticarcinogenic Agents; Carcinogens; Chromatography, High Pressure Liquid; Glucosides; Hydrolyzable Tannins; Mice; Mice, Inbred BALB C; Plant Extracts; Plant Leaves; Plants, Medicinal; Skin Neoplasms; Tannins; Tumor Necrosis Factor-alpha

An activity directed fractionation of a 50% aqueous ethanol extract of A. wilkesiana and A. hispida leaves resulted in the isolation of gallic acid, corilagin and geraniin as the compounds responsible for the observed antimicrobial activity. Quercetin 3-O-rutinoside and kaempferol 3-O-rutinoside were also isolated from the inactive fraction of A. hispida. The structures were established by permethylation, 2D - NMR ((1)H and (13)C) and MS data.

Topics: Anti-Bacterial Agents; Euphorbiaceae; Glucosides; Humans; Hydrolyzable Tannins; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Plant Extracts; Plant Leaves; Plants, Medicinal; Tannins

Topics: Arachidonic Acid; Arachidonic Acids; Benzopyrans; Ellagic Acid; Glucosides; Glycosides; Humans; Hydrolyzable Tannins; In Vitro Techniques; Leukocytes; Tannins