Antimicrobial Terpenoids from the Oleoresin of the Peruvian Medicinal Plant Copaifera paupera

Abstract

Twelve known diterpenes 1 - 11 and 13, and three known sesquiterpenes 14 - 16, along with a new C₂₀ - C₁₅ 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 μg/ml) against Gram-positive bacteria, comparable with cephotaxime used as control. Compound 2 exhibited moderate cytotoxic activity against four cancer cell lines.

Key words

Copaifera paupera - Leguminosae - Copaiba oil - terpenoids - leishmanicidal - antimicrobial - cytotoxic - aldose reductase inhibitory activities

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1 ^† Deceased