RESUMO
Here we report the discovery and synthesis of complex polybrominated p-terphenyl ethers isolated from a mushroom (Boletopsis sp.) used as a traditional medicine by the Kiovi people in the highlands of Papua New Guinea. Boletopsins 13 and 14 represent the first report of polybrominated fungal metabolites to be produced by a terrestrial fungus. The synthetic method employs 2,4,4,6-tetrabromo-2,5-cyclohexadienone to achieve selective polybromination of the extended aromatic system in a selective and sequential manner.
Assuntos
Agaricales/química , Hidrocarbonetos Bromados , Compostos de Terfenil , Basidiomycota , Escherichia coli/efeitos dos fármacos , Hidrocarbonetos Bromados/síntese química , Hidrocarbonetos Bromados/química , Hidrocarbonetos Bromados/isolamento & purificação , Hidrocarbonetos Bromados/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Papua Nova Guiné , Staphylococcus epidermidis/efeitos dos fármacos , Compostos de Terfenil/síntese química , Compostos de Terfenil/química , Compostos de Terfenil/isolamento & purificação , Compostos de Terfenil/farmacologiaRESUMO
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one) massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %). The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one) massoia lactone (1.4 %) and the saturated C-10 derivative delta-decalactone (2.5 %).
Assuntos
Cryptocarya/química , Frutas/química , Lauraceae/química , Óleos Voláteis/química , Casca de Planta/química , Óleos de Plantas/química , Papua Nova GuinéRESUMO
Exhaustive hydro-distillation of the leaves of Piper aduncum and fruits of Piper gibbilimbum (Piperaceae) afforded colorless and pale orange colored oils in 0.35 and 0.30 % yields, respectively. Detailed chemical analysis by GC/MS indicated the volatile constituents of Piper aduncum to be composed of dill apiole (43.3%), beta-caryophyllene (8.2%), piperitione (6.7%) and alpha-humulene (5.1%), whilst the oil of P. gibbilimbum is dominated by the gibbilimbols A-D (74.2%), with the remaining major constituents being the terpenes camphene (13.6%) and alpha-pinene (6.5%).