Antimicrobial terpenoids from the oleoresin of the Peruvian medicinal plant Copaifera paupera.
Twelve known diterpenes 1 - 11 and 13, and three known sesquiterpenes 14 - 16, along with a new C(20) - C(15) terpenoid 17, with a structure based on an unprecedented skeleton in which a labdane diterpene is linked to a monocyclic sesquiterpene by an ester bridge, were isolated from the oleoresin of the Peruvian medicinal plant Copaifera paupera (Herzog) Dwyer (Leguminosae). Their structures were elucidated on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC and HMBC), and by comparison with data in the literature. The leishmanicidal, antimicrobial, cytotoxic, and aldose reductase inhibitory activities were studied. Compounds 1 and 11 showed significant antimicrobial activity (MIC < 10 microg/ml) against Gram-positive bacteria, comparable with cephotaxime used as control. Compound 2 exhibited moderate cytotoxic activity against four cancer cell lines.
D000449:Aldehyde Reductase / Q000378:metabolism; D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D007887:Fabaceae; D019073:HT29 Cells / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010568:Peru; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D013729:Terpenes; C018620:oleoresins; D000449:Aldehyde Reductase