ellagitannin and 1-1-diphenyl-2-picrylhydrazyl

Ethnopharmacological relevance; Several plant species of Miconia genus are commonly used in Brazilian folk medicine as anti-inflammatory agents and for the treatment of infectious diseases. Infusions and extracts of Miconia species are also reported as analgesic, antimicrobial, antimalarial, antioxidant, anti-inflammatory, antinociceptive, antimutagenic, and antitumoral. Aim of the study; To determine the phytochemical composition of an aqueous extract of Miconia latecrenata leaves and to evaluate its antioxidant, antibacterial, antimutagenic and antigenotoxic activities. Materials and Methods; The following methods were used for the different effects: I) antioxidant - β-carotene/linoleic acid, lipid peroxidation, and DPPH• radical scavenging; II) antibacterial - agar well diffusion and MIC methods); III) antimutagenic assays - Ames Test; and IV) antigenotoxic - Plasmid cleavage test. The phytochemical analysis and phenolic quantification were carried out by UPLC-DAD-ESI-MS/MS and colorimetry, respectively. In addition, statistical correlation analysis was performed aiming to evaluate the Pearson correlation between phenolic compounds and biological assays. Results; A high content of tannins was observed and the ellagitannin isomers of 1,2,3,5-tris-galloyl-4,6-HHDP-glucose were identified as the main constituents of the leaves aqueous extract. High antioxidant effect, in different tests, high antibacterial activity to gram-positive and negative strains, as well as high antimutagenic activity were observed. Statistical analysis showed a high Pearson correlation for the tannin content in relation to the results of the antioxidant and antibacterial tests. In general, the antioxidant action of the aqueous extract showed low correlation with the antimutagenic activity. Conclusions; The present results confirmed the expectations regarding the pharmacological profile of M. latecrenata supporting its therapeutic potential in relation to ROS/RNS related disorders. Furthermore, the phenolic compounds of M. latecrenata can act, in turn, minimizing or inhibiting the biological macromolecules damage, especially DNA.

Topics: Anti-Bacterial Agents; Antimutagenic Agents; Antioxidants; Biphenyl Compounds; Escherichia coli; Hydrolyzable Tannins; Melastomataceae; Picrates; Plant Extracts; Plant Leaves; Salmonella typhimurium; Staphylococcus aureus

Two new phenolic compounds, 4-O-glucopyranosyl-5-O-caffeoylshikimic acid (1) and 2,3-digalloyl oregonin (2), were isolated along with eight known phenolic compounds (3-10) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds (1-10) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol.

Topics: Alnus; Antioxidants; Ascorbic Acid; Biphenyl Compounds; Diarylheptanoids; Drug Evaluation, Preclinical; Free Radical Scavengers; Gallic Acid; Glucosides; Hydrolyzable Tannins; Magnetic Resonance Spectroscopy; Phenols; Picrates; Plant Extracts; Plant Leaves; Shikimic Acid; Superoxides