RESUMO
Callophycoic acids A-H (1-8) and callophycols A and B (9 and 10) were isolated from extracts of the Fijian red alga Callophycus serratus, and identified by NMR, X-ray, and mass spectral analyses. These natural products represent four novel carbon skeletons, providing the first examples of diterpene-benzoic acids and diterpene-phenols in macroalgae. Compounds 1-10 exhibited antibacterial, antimalarial, and anticancer activity, although they are less bioactive than diterpene-benzoate macrolides previously isolated from this red alga.
Assuntos
Benzoatos/química , Diterpenos/química , Fenóis/química , Rodófitas/química , Animais , Benzoatos/isolamento & purificação , Benzoatos/farmacologia , Cristalografia por Raios X , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , Fenóis/isolamento & purificação , Fenóis/farmacologiaRESUMO
Bromophycolides C-I (1-7) were isolated from extracts of the Fijian red alga Callophycus serratus and identified by NMR and mass spectral techniques. These novel natural products share a carbon skeleton and biosynthetic origin with previously identified bromophycolides A (8) and B (9), which form a rare group of diterpene-benzoate macrolides. Bromophycolides C-I (1-7) displayed modest antineoplastic activity against a range of human tumor cell lines.
Assuntos
Antineoplásicos/isolamento & purificação , Diterpenos/isolamento & purificação , Macrolídeos/isolamento & purificação , Rodófitas/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Fiji , Humanos , Macrolídeos/química , Macrolídeos/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Células Tumorais CultivadasRESUMO
[structures: see text] Three diterpene-benzoate natural products, with novel carbon skeletons and an unusual proposed biosynthesis, were isolated from extracts of the Fijian red alga Callophycus serratus and identified by a combination of X-ray crystallographic, NMR, and mass spectral analyses. Bromophycolide A (1) displayed cytotoxicity against several human tumor cell lines via specific apoptotic cell death. This represents the first discovery of natural products incorporating a diterpene and benzoate skeleton into a macrolide system.
Assuntos
Antineoplásicos/isolamento & purificação , Benzoatos/isolamento & purificação , Diterpenos/isolamento & purificação , Macrolídeos/isolamento & purificação , Rodófitas/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Benzoatos/química , Benzoatos/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Farmacorresistência Bacteriana , Ensaios de Seleção de Medicamentos Antitumorais , Fiji , Humanos , Macrolídeos/química , Macrolídeos/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Células Tumorais CultivadasRESUMO
Although macrophyte herbivore interactions in freshwater systems were generally disregarded for many years, recent data suggest that herbivory can be intense and important in structuring freshwater communities. This has led to the hypothesis that chemical defenses should be common among freshwater plants, but few studies have reported such chemical defenses, and no previous studies have assessed the frequency of chemical defenses among a substantial number of freshwater plant species. In a study of 21 macrophyte species co-occurring with the omnivorous crayfish Procambarus acutus in a southeastern USA wetland environment, we found that extracts of 11 species (52%) deterred feeding by P. acutus when tested in artificial foods at natural concentrations. Of these 11 chemically defended species, one species, Eupatorium capillifolium, consistently had a more unpalatable extract following mechanical damage to plant tissue, indicative of an activated chemical defense. Because herbivores are commonly nitrogen-limited and select food based on several plant traits, including plant nutritional value, it might be expected that chemical defenses would be especially important for protein-rich plants. However, we found no relationship between soluble protein concentration and deterrence of plant extracts.
