A New Labdane Diterpene From Copaifera langsdorffii Oil-Resin

Copaifera spp. (Fabaceae) is a common tree species found in the tropical region of Latin America, popularly known as copaiba or pau-d'alho. From the trunk of different Copaifera species exude an oil-resin widely used in folk medicine due to it antimicrobial, anti-inflammatory, antitumor, antinociceptive, antileishmanial and healing properties. The oil-resin is composed of volatile compounds and resinous acids, mainly sesquiterpenes and diterpenes, that showed promissing biological activities, specially antimicrobial and anti-inflammatory properties. Contributing to complement the knowledge about the chemical composition of C. langsdorffii oil-resin, here we describe the isolation and structural elucidation of a new labdane diterpene from this source. The oil-resin was purchased from Apis Flora® (Lot 007900117, Ribeirão Preto, SP, Brazil) and fractionated by column vacuum chromatography using potassium hydroxide impregnated silica gel2 to obtain the resinous fraction (RAF). From RAF, the new labdane diterpene (1) was isolated by chromatographic methods and the structure was established by 1D and 2D NMR spectra and HR-ESI-MS. A detailed analysis of spectroscopic data (Table 1) and comparison with literature references3 allowed the identification of 1 (Fig. 1) as 14,15-dinor-13-oxo-8(17)-labden-19-oic acid, and to the best of our knowledge it has not yet been reported for the Fabaceae family.