Antimicrobial and Antiinsectan Phenolic Metabolites of Dalea searlsiae
| Autor: | Gil Belofsky, Christina M. Coleman, Daneel Ferreira, Eric Foss, Patrick F. Dowd, Jane Diamond, Mario Aronica, Jacob Darley, Felipe Santana |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Circular dichroism
Staphylococcus aureus Stereochemistry Bacillus cereus Pharmaceutical Science Microbial Sensitivity Tests Spodoptera 010402 general chemistry 01 natural sciences Plant Roots Article Analytical Chemistry chemistry.chemical_compound Anti-Infective Agents Phenols Drug Discovery Bioassay Animals Oxacillin Pharmacology Flavonoids Chromatography biology Molecular Structure 010405 organic chemistry Organic Chemistry fungi food and beverages Fabaceae biology.organism_classification Antimicrobial Streptococcus mutans 0104 chemical sciences Complementary and alternative medicine chemistry Larva Flavanones Molecular Medicine Dalea Bacteria |
| Zdroj: | Journal of Natural Products |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Continued interest in the chemistry of Dalea spp. led to investigation of Dalea searlsiae, a plant native to areas of the western United States. Methanol extractions of D. searlsiae roots and subsequent chromatographic fractionation afforded the new prenylated and geranylated flavanones malheurans A-D (1-4) and known flavanones (5 and 6). Known rotenoids (7 and 8) and isoflavones (9 and 10) were isolated from aerial portions. Structure determination of pure compounds was accomplished primarily by extensive 1D- and 2D-NMR spectroscopy. The absolute configurations of compounds 1-5, 7, and 8 were assigned using electronic circular dichroism spectroscopy. Antimicrobial bioassays revealed significant activity concentrated in the plant roots. Compounds 1-6 exhibited MICs of 2-8 μg/mL against Streptococcus mutans, Bacillus cereus, and oxacillin-sensitive and -resistant Staphylococcus aureus. Aerial metabolites 7-10 were inactive against these organisms, but the presence of 7 and 8 prompted investigation of the antiinsectan activity of D. searlsiae metabolites toward the major crop pest Spodoptera frugiperda (fall armyworm). While compounds 1-10 all caused significant reductions in larval growth rates, associated mortality (33-66%) was highest with flavanone 4 and rotenoids 7 and 8. These findings suggest a differential allocation of antimicrobial and antiinsectan plant resources to root and aerial portions of the plant, respectively. |
| Databáze: | OpenAIRE |
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