Abstract
Oleoresins from Copaifera species are extensively used in folk medicine in Brazil, which are employed mainly in the production of cosmetic formulations in Brazil, North America and Europe. Considering the lack of validated analytical methods for the analyses of diterpenes in Copaifera oleoresins, it was developed a validated and reliable reversed-phase high-performance liquid chromatography with photodiode array detection (RP-HPLC-PDA) method for the analysis of six diterpenes, including: (-)-polyalthic acid; (13E)-ent-labda-7,13-dien-15-oic acid; ent-8(17)-labden-15,18-dioic acid; (-)-copalic acid; (-)-3β-acetoxycopalic acid and (-)-3β-hydroxycopalic acid. These compounds were isolated from C. duckei, C. reticulata and C. multijuga oleoresins by chromatographic means. The analytical curves were linear with regression coefficients (r2) between 0.9903 and 0.9999. The limits of detection (LOD) and quantification (LOQ) values were 0.35 to 3.09 µg mL-1 and 1.05 to 9.36 µg mL-1, respectively. The method also displayed good precision and accuracy. The developed analytical method is reliable and a useful tool for the analysis of Copaifera oleoresin and its products.
Highlights
The Copaifera genus (Leguminoseae) consists of approximately 72 species, from which 16 of them occur only in Brazil, mainly in Northern region in the states of Amazonas, Pará and Ceará.[1,2] These trees are popularly known as “copaiba”, “copaibeiras” or “pau d’óleo”, and the oleoresins obtained from their trunks are extensively used in folk medicine due to their antiinflammatory, analgesic, wound healing, antimicrobial, antileishmanial and antitumoral properties.[2,3] Such ethnopharmacological relevance has stimulated several researchers to investigate their biological activities, which corroborated their pharmacological potential.[4,5,6,7,8] In addition to their pharmaceutical properties, these balsams are largely used as dietary supplement, employed in the production of flavoring agents, and extensivelyDespite the great relevance of these oleoresins for pharmaceutical and cosmetic industries, most of these commercial balsams have not been authenticated, and their chemical profile has not been well established, hindering their industrial and biomedical applications, as well as impairing the quality and economic value of such products.[9,10]Chemically, the oleoresins of copaiba are predominantly composed by a mixture of volatile and non-volatile compounds comprising mainly sesquiterpenes and acid diterpenes
Compounds 1-6 (Figure 1) were isolated as main diterpenes from OCd, OCm and OCr, and their 1H and 13C nuclear magnetic resonance (NMR) spectroscopic data are in agreement with those previously reported in the literature: (–)-polyalthic acid (1),[28] (13E)-ent-labda-7,13-dien15‐oic acid (2),[29] ent‐8(17)‐labden-15,18-dioic acid (3),[30] (–)-copalic acid (4),[31] (–)-3β-acetoxycopalic acid (5),[32] (–)-3β-hydroxycopalic acid (6).[33]
These compounds were evaluated by thin layer chromatography (TLC) using different solvent systems
Summary
The Copaifera genus (Leguminoseae) consists of approximately 72 species, from which 16 of them occur only in Brazil, mainly in Northern region in the states of Amazonas, Pará and Ceará.[1,2] These trees are popularly known as “copaiba”, “copaibeiras” or “pau d’óleo”, and the oleoresins obtained from their trunks are extensively used in folk medicine due to their antiinflammatory, analgesic, wound healing, antimicrobial, antileishmanial and antitumoral properties.[2,3] Such ethnopharmacological relevance has stimulated several researchers to investigate their biological activities, which corroborated their pharmacological potential.[4,5,6,7,8] In addition to their pharmaceutical properties, these balsams are largely used as dietary supplement, employed in the production of flavoring agents, and extensivelyDespite the great relevance of these oleoresins for pharmaceutical and cosmetic industries, most of these commercial balsams have not been authenticated, and their chemical profile has not been well established, hindering their industrial and biomedical applications, as well as impairing the quality and economic value of such products.[9,10]Chemically, the oleoresins of copaiba are predominantly composed by a mixture of volatile and non-volatile compounds comprising mainly sesquiterpenes and acid diterpenes. Chromatographic analyses of NVCd, NVCm and NVCr were performed through RP-HPLC-PDA using a Shim-pack CLC-ODS column (250 × 4.6 mm i.d., 5 μm; Shimadzu), and an isocratic system consisting of acetonitrile and water with 0.1% acetic acid (8:2 v/v) as mobile phase, which was established through initial experiments using the gradient scouting run evaluation as previously described.[23] The temperature of the column was set at 40 °C, the flow rate was 1.0 mL min-1, the injected volume was 20.0 μL and the detection wavelength was set at 201 nm.
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