Copaifera (Leguminoseae) species produce oleoresins of high commercial importance, which are sold from the Amazon region to other Brazilian regions or exported to Europe and North America countries. These oils are very used in cosmetics industries due to their emollient, antibacterial and anti-inflammatory properties, being also used for medicinal purposes, such as anti-inflammatory, antiseptic, antiasthmatic, analgesic, antidiarrheal, healing, aphrodisiac, antioxidant, antitetanic, antiherpes, antimicrobial, anticancer and antitumor, among others. However, in despite of their pharmacological importance, most of the Copaifera oleoresins are generically commercialized as "copaiba oils", without the correct identification of the species the oleoresin was extracted from. In this context, aiming to assure the efficacy, safety and quality of these phytotherapeutics, it was recently approved by FAPESP a thematic project to validate the chemistry and the pharmacology of extracts and active principles of Copaifera species (proc. FAPESP 2011/13630-7). Thus, as part of the dereplication studies of Copaifera oleoresins proposed in that Project, the goals of this proposal are the isolatation and structural elucidation of labdane-type diterpenes from the Copaifera langsdorffii oleoresin, and the investigation of the fragmentation pathways of their protonated and/or deprotonated molecules using tandem mass spectrometry (MS/MS). These diterpenes are amongst the major chemical constituents of the oleoresin of Copaifera. Firstly, they will be analyzed using atmospheric pressure chemical ionization (APCI) and electrospray (ESI) sources in the positive and negative ion modes in order to identify the most adequate ionization source and analysis mode for further dereplication studies proposed in the thematic project. After, the main diagnostic fragment ions will be identified and their formation will be rationalized from structure-fragmentation correlations. Finally, the mechanistic pathways will be elucidated on the basis of thermochemical data obtained by Computational Quantic Chemistry.
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