tannins and chebulagic-acid

Coxsackievirus A16 (CVA16) is an etiologic agent of hand, foot, and mouth disease (HFMD) that affects young children, and although typically self-limited, severe complications, and fatal cases have been reported. Due to the lack of specific medication and vaccines against CVA16, there is currently a need to develop effective antivirals to better control CVA16 infections in epidemic areas. In this study, we identified the tannins chebulagic acid (CHLA) and punicalagin (PUG) as small molecules that can efficiently disrupt the CVA16 infection of human rhabdomyosarcoma cells. Both compounds significantly reduced CVA16 infectivity at micromolar concentrations without apparent cytotoxicity. A mechanistic analysis revealed that the tannins particularly targeted the CVA16 entry phase by inactivating cell-free viral particles and inhibiting viral binding. Further examination by molecular docking analysis pinpointed the targets of the tannins in the fivefold axis canyon region of the CVA16 capsid near the pocket entrance that functions in cell surface receptor binding. We suggest that CHLA and PUG are efficient antagonists of CVA16 entry and could be of value as antiviral candidates or as starting points for developing molecules to treat CVA16 infections.

Topics: Antiviral Agents; Benzopyrans; Capsid Proteins; Enterovirus A, Human; Enterovirus Infections; Glucosides; Humans; Hydrolyzable Tannins; Molecular Docking Simulation; Small Molecule Libraries; Tannins; Virus Attachment

The bioassay-directed isolation of Terminalia chebula fruits afforded four human immunodeficiency virus type 1 (HIV-1) integrase inhibitors, gallic acid ( 1) and three galloyl glucoses ( 2 - 4). In addition, four flavonol glycoside gallates ( 5 - 8) from Euphorbia pekinensis containing the galloyl moiety also showed the inhibitory activity at a level comparable to those of 2 - 4. By comparison with the activities of the compounds not bearing this moiety, it is proposed that the galloyl moiety plays a major role for inhibition against the 3'-processing of HIV-1 integrase of these compounds.

Topics: Benzopyrans; Carbohydrate Sequence; Euphorbia; Flavonoids; Fruit; Gallic Acid; Glucosides; Glycosides; HIV Integrase; HIV Integrase Inhibitors; Hydrolyzable Tannins; Molecular Sequence Data; Molecular Structure; Plant Extracts; RNA-Directed DNA Polymerase; Rutin; Tannins; Terminalia

We used the agar dilution method to evaluate the antibacterial effect of Terminalia macroptera leaf (Tml) extract against nine reference and clinical Neisseria gonorrhoeae strains, including penicillin- and tetracycline-resistant and -susceptible strains. Tml possesses anti-N. gonorrhoeae activity against all of the strains and the minimum inhibitory concentrations (MIC) were between 100 and 200 microg ml(-1). We then used a liquid-liquid partition method to divide the Tml extract into five fractions and determined the anti-N. gonorrhoeae activity of each of the fractions. All of the fractions showed antibacterial activity. The most active one was identified as the diethyl ether fraction and had MIC values of between 25 and 50 microg ml(-1) against all of the strains.

Topics: Anti-Bacterial Agents; Benzopyrans; Ellagic Acid; Flavonoids; Gallic Acid; Glucosides; Hydrolyzable Tannins; Luteolin; Neisseria gonorrhoeae; Plant Extracts; Plant Leaves; Tannins; Terminalia

To analyze the hydrolyzable tannins-chebulinic acid (I) and chebulagic acid(II) in Fructus Chebulae and its confusion varieties by using high performance capillary electrophoresis (HPCE) method.. Using a capillary (375 microns OD x 50 microns ID; 81.5 cm x 61.5 cm) and a power supply set at 24 kV, with phosphate-borate buffer containing 20 mmol.L-1 Na2HPO4-60 mmol.L-1 boric acid and a UV detector at 280 nm, sample solution was loaded in decompression mode at the positive end of the capillary, the loading time was 5 s.. The linear ranges of I and II were 0.0842-0.842 and 0.842 and 0.0940-0.940 mg.mL-1 respectively, the correlation coefficient were 0.9966 and 0.9957, the average recoveries were 95.6% (RSD = 4.0%, n = 5) and 95.0% (RSD = 4.4%, n = 5), the RSDs (n = 5) of measurement precision test were 2.2% and 1.7%, the RSDs (n = 6) of reproduction test were 5.4% and 4.0% respectively. The contents of I and II were obviously interrelated with the variety and characteristics of Fructus Chebulae, the contents of I and II in the confusion varieties of Fructus Chebulae were very low.. It is suitable to use I and II as the criterion in quality evaluation of Fructus Chebulae, and the HPCE method is effective for quality evaluation of the crude Fructus Chebulae.

Topics: Benzopyrans; Drug Contamination; Electrophoresis, Capillary; Fruit; Glucosides; Hydrolyzable Tannins; Plants, Medicinal; Quality Control; Tannins; Terminalia

Three hydrolyzable tannins chebulinic acid (I), chebulagic acid(II) and 1,3, 6-tri-O-galloyl-beta-D-glucose (III) in Fructus Chebulae from different habitats were determined by RP-HPLC method. The contents of I and II were obviously interrelated with the variety and characteristics of Fructus Chebulae. It's suitable to use I and II as indexes in quality evaluation of the crude drug of Fructus Chebulae.

Topics: Benzopyrans; Fruit; Glucosides; Hydrolyzable Tannins; Plants, Medicinal; Quality Control; Species Specificity; Tannins; Terminalia