Using Enzyme Assays to Evaluate the Structure and Bioactivity of Sponge-Derived Meroterpenes
| Autor: | Eric K. Hoobler, Karen Tenney, Sarah J. Robinson, Theodore R. Holman, Michelle Riener, Frederick A. Valeriote, Phillip Crews, Steven T. Loveridge |
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| Rok vydání: | 2009 |
| Předmět: |
Blood Platelets
Reticulocytes Stereochemistry Xanthones Pharmaceutical Science Pharmacognosy Article Analytical Chemistry Terpene Papua New Guinea chemistry.chemical_compound Drug Discovery Animals Humans Lipoxygenase Inhibitors Phenols Nuclear Magnetic Resonance Biomolecular Pharmacology chemistry.chemical_classification Molecular Structure biology Terpenes Chemistry Organic Chemistry Diastereomer Stereoisomerism Biological activity Enzyme assay Terpenoid Porifera Enzyme Complementary and alternative medicine biology.protein Molecular Medicine Diterpenes Sesquiterpenes |
| Zdroj: | Journal of Natural Products. 72:1857-1863 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Enzyme screening of crude sponge extracts prioritized a 2005 Papua New Guinea collection of Hyrtios sp. for further study. The MeOH extract contained puupehenone and four puupehenone analogues (1, 2, 3, 5, and 7) along with a new diastereomer, 20-epi-hydroxyhaterumadienone (4), and a new analogue, 15-oxo-puupehenoic acid (6). The drimane terpene core of 4 and 6 was rapidly dereplicated, and the modified Mosher's method identified 4, while 1D and 2D NMR techniques were used to solve 6. These compounds plus noteworthy repository natural products and standards were tested against three lipoxygenase isozymes, human 5-, 12-, and 15-lipoxygenases. Significant potency and selectivity profiles were exhibited in the human 5-lipoxygenase assay by puupehenone (1) and jaspaquinol (9) and structural factors responsible for activity identified. |
| Databáze: | OpenAIRE |
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