New Galloylated Flavanonols from the Australian PlantGlochidion sumatranum
| Autor: | Sheng Yin, Rohan A. Davis, David Brian Camp, Ronald J. Quinn, Vicky M. Avery, Melissa Sykes, Todd Shelper |
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| Rok vydání: | 2010 |
| Předmět: |
Staphylococcus aureus
Stereochemistry Chemical structure Pharmaceutical Science Analytical Chemistry Magnoliopsida chemistry.chemical_compound Isomerism Pseudomonas Drug Discovery Structural isomer Phenols Antibacterial agent Flavonoids Pharmacology Glochidion sumatranum Molecular Structure Plant Stems biology Plant Extracts Organic Chemistry Absolute configuration Flavanonol biology.organism_classification Anti-Bacterial Agents Plant Leaves Complementary and alternative medicine chemistry Molecular Medicine Glochidion |
| Zdroj: | Planta Medica. 76:1877-1881 |
| ISSN: | 1439-0221 0032-0943 |
| DOI: | 10.1055/s-0030-1250071 |
| Popis: | Bioassay-guided fractionation of the CH(2)Cl(2)/MeOH extract from the Australian plant Glochidion sumatranum resulted in the isolation of four new galloylated flavanonols, (2R,3R)-dihydromyricetin-4'-O-(3''-O-methyl)-gallate (1), (2R,3R)-dihydromyricetin-3'-O-(3''-O-methyl)-gallate (2), (2R,3R)-dihydromyricetin-4'-O-gallate (3), and (2R,3R)-dihydromyricetin-3'-O-gallate (4), along with the known compound, (2R,3R)-dihydromyricetin (5). The structures of 1-5 were determined by NMR and MS analysis and their absolute configuration was elucidated by comparison of the CD data with literature values. Compounds 1/2 and 3/4 are two pairs of structural isomers that were shown to interconvert by transesterification during NMR and LC-MS studies. This process involved the intramolecular migration of the galloyl moieties between C-3' and C-4' of the flavanonol skeleton. Compounds 1 and 3 were identified as the more stable isomers. Compounds 1, 3, and 5 showed weak activity against the gram-negative bacterium Pseudomonas aeruginosa and the gram-positive bacterium Staphylococcus aureus. |
| Databáze: | OpenAIRE |
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