punicalagin and chebulinic-acid

Ellagitannins are literally a class of tannins. Triggered by the oxidation of the phenolic parts on β-pentagalloyl-d-glucose, ellagitannins are generated through various structural conversions, such as the coupling of the phenolic parts, oxidation to highly complex structures, and the formation of dimer and lager analogs, which expand the structural diversity. To date, more than 1000 natural ellagitannins have been identified. Since these phenolic compounds exhibit a variety of biological activities, ellagitannins have potential applications in medicine and health enhancement. Within the context of identifying suitable applications, considerations need to be based on correct structural features. This review describes the structural revisions of 32 natural ellagitannins, namely alnusiin; alnusnin A and B; castalagin; castalin; casuarinin; cercidinin A and B; chebulagic acid; chebulinic acid; corilagin; geraniin; isoterchebin; nobotanin B, C, E, G, H, I, J, and K; punicalagin; punicalin; punigluconin; roxbin B; sanguiin H-2, H-3, and H-6; stachyurin; terchebin; vescalagin; and vescalin. The major focus is on the outline of the initial structural determination, on the processes to find the errors in the structure, and on the methods for the revision of the structure.

Topics: Benzopyrans; Glucosides; Hydrolyzable Tannins; Molecular Structure; Oxidation-Reduction; Phenols; Terminology as Topic

Topics: Acetylcholinesterase; Binding Sites; Fruit; Hydrolyzable Tannins; Kinetics; Molecular Docking Simulation; Protein Binding; Spectroscopy, Fourier Transform Infrared; Terminalia

This study identified and quantified hydrolysable tannins (HTs) in Terminalia ferdinandiana Exell (Kakadu plum) fruit, freeze dried powder extracted with 80% aqueous acetone (AA) and 80% aqueous acidified ethanol (AAE), using UHPLC-Q/Orbitrap/MS/MS. The vitamin C and ellagic acid were quantified by UHPLC-PDA. A total of seven HTs were identified: corilagin, 3,4,6-tri-O-galloyl-β-d-glucose, elaeocarpusin, chebulinic acid, chebulagic acid, helioscopin B, and punicalagin, with five classified as ellagitannins. The two extracts AA and AAE, comprised of gallic acid (2.5 and 2.2 mg/g DW), punicalagins α and β (2.8 and 1.3 mg/g DW), respectively, and both contained ellagic acid (~4 g/100 g DW). These extracts showed high antioxidant properties and strong antimicrobial effects against methicillin-resistant Staphylococcus aureus clinical isolate, Staphylococcus aureus, and Shewanella putrefaciens. These results suggest that Kakadu plum fruit is a rich, edible source of ellagitannins, ellagic acid and vitamin C with potential applications in food, cosmetic and nutraceutical industries.

Topics: Anti-Bacterial Agents; Antioxidants; Ethanol; Freeze Drying; Fruit; Glucosides; Hydrolyzable Tannins; Methicillin-Resistant Staphylococcus aureus; Plant Extracts; Powders; Solvents; Tandem Mass Spectrometry; Terminalia

The aqueous extract of galls from Terminalia chebula Retz. (Combretaceae) was fractionated on Diaion and refractionated on octadecyl silica column. Six phenolic compounds were isolated and identified as gallic acid (1), punicalagin (2), isoterchebulin (3), 1,3,6-tri-O-galloyl-β-D-glucopyranose (4), chebulagic acid (5) and chebulinic acid (6). All of the compounds showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and melanin inhibitory activities than ascorbic acid, butylated hydroxytoluene, α-tocopherol, arbutin and kojic acid, the reference compounds. Gallic acid (1) exhibited inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages. However, all isolated compounds exhibited less activity than the reference compounds in mushroom tyrosinase inhibition and human tumour cytotoxicity assays. This study has demonstrated that the phenolic compounds isolated from galls of T. chebula might contribute significantly due to their antioxidant and whitening activities.

Topics: Analysis of Variance; Animals; Benzopyrans; Biphenyl Compounds; Cell Line, Tumor; Cell Proliferation; Chemical Fractionation; Free Radical Scavengers; Gallic Acid; Glucosides; Humans; Hydrolyzable Tannins; Melanins; Mice; Molecular Structure; Nitric Oxide; Phenols; Picrates; Plant Extracts; Plant Tumors; 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