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 (r 2 ) 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.Keywords: Copaifera spp., oleoresins, diterpenes, RP-HPLC-PDA IntroductionThe 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 also largely used as dietary supplement, employed in the production of flavoring agents, and extensively commercialized as crude oil in Brazil. Moreover, these natural products are exported to Europe and North America, to be used mainly in cosmetic formulations. 2,9 Despite 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, thus 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. Acid diterpenes stands out for a wide range of the biological properties reported for these oleoresins, such as: antimicrobial, antitumoral, antinociceptive and anti-inflammatory, among others. 3,4,6,[11][12][13][14][15] Despite this fact, most of the studies reporting the chemical identification and quan...
In this article, the in vitro schistosomicidal effects of three Brazilian Copaifera oleoresins (C. duckei, C. langsdorffii, and C. reticulata) are reported. From these botanical sources, the oleoresin of C. duckei (OCd) demonstrated to be the most promising, displaying LC values of 75.8, 50.6, and 47.2 μg/ml at 24, 48, and 72 h of incubation, respectively, against adult worms of Schistosoma mansoni, with a selectivity index of 10.26. Therefore, the major compounds from OCd were isolated, and the diterpene, (-)-polyalthic acid (PA), showed to be active (LC values of 41.7, 36.2, and 33.4 μg/ml, respectively, at 24, 48, and 72 h of incubation). Moreover, OCd and PA affected the production and development of eggs, and OCd modified the functionality of the tegument of S. mansoni. Possible synergistic and/or additive effects of this balsam were also verified when a mixture of the two of its main compounds (PA and ent-labd-8(17)-en-15,18-dioic acid) in the specific proportion of 3:1 (w/w) was tested. The obtained results indicate that PA should be considered for further investigations against S. mansoni, such as, synergistic (combination with praziquantel (PZQ)) and in vivo studies. It also shows that diterpenes are an important class of natural compounds for the investigation of agents capable of fighting the parasite responsible for human schistosomiasis.
The Copaifera species (Leguminoseae) are popularly known as 'copaíba' or 'copaíva' and are grown in the states of Amazonas, Pará and Ceará in northern Brazil. The oleoresins obtained from these species have been extensively used owing to their pharmacological potential and their application in cosmetic and pharmaceutical preparations. In the present study, the development and validation of a novel, rapid and efficient RP-HPLC methodology for the analysis of the diterpene (-)-copalic acid (CA), pointed out as the only chemical marker of the Copaifera genus, are described. The regression equation (Y = 26,707x - 29,498) was obtained with good linearity (r(2) = 0.9993) and the limits of quantification and detection were 9.182 and 3.032 µg/mL, respectively. The precision and the accuracy of the method were adequate (lower than 4%). Finally, the validation parameters evaluated were satisfactorily met, so the developed method represents a suitable tool for application in the quality control of such natural products. Further studies aiming to develop analytical methodologies for each Copaifera species using a more representative number of chemical markers should be performed.
(-)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (-)-hinokinin (HK) and (-)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween® 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HK or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2 - cyclooxygenase-2) interaction in comparison with CUB and HK.
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