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Chemical Composition of Portuguese Propolis Bioactive Properties

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Chemical Composition of Portuguese Propolis Bioactive Properties CHEMICAL COMPOSITION OF PORTUGUESE PROPOLIS BIOACTIVE PROPERTIES SORAIA ISABEL DOMINGUES MARCOS FALCÃO Thesis submitted to the Faculty of Sciences of the University of Porto in partial fulfillment of the requirements for the degree of Doctor in Chemistry Supervisor: Professora Doutora Ana Cristina Moreira Freire Co-Supervisor: Professor Doutor Miguel José R. Vilas Boas 2013 I II To my Parents and Miguel III IV Acknowlegdments To Fundação para a Ciência e a Tecnologia (FCT) for my PhD Grant with reference SFRH/BD/44855/2008 financially supported by program QREN-POPH-Tipology 4.1- Advanced Formation, European Social Fund and MCTES. To Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto for accepting me as a PhD student in the Doctoral Program of Chemistry. To my supervisor, Professor Cristina Freire, for accepting to supervise my work, for her knowledge, the dedication in supervising this work, her friendship, the valuable advices and suggestions and the constant availability for helping me. To my co-supervisor, Professor Miguel Vilas-Boas, for the excellent work and dedication in supervising, his knowledge and for the fruitful discussions. For always questing me about my results and the encouragement given in pursuing new scientific goals. For all the accomplished goals and above all for his friendship. To have worked under your supervision made me grow up and recognize that professional success is the result of the effort and dedication. To Professor Ana Cristina Figueiredo from Departamento de Biologia, Faculdade de Ciências, Universidade de Lisboa for welcoming me so well during my research trainings/stay in Lisbon, and for the profitable discussions regarding volatile compounds, for revising my work, for her patience, friendship, sympathy and for the constant availability in the discussing of the results. To Professor Maria do Rosário Domingues from the Departamento de Química, Universidade de Aveiro for welcoming me during my work of mass spectrometry and for her help in the MS characterization of propolis extracts and availability in the discussion of the chemical structures of propolis composition. V To Professor Susana M. Cardoso from Escola Superior Agrária de Coimbra, for her friendship, patience, availability and fruitful discussions about propolis MS characterization as well as for the help in revising my MS results. To Professor Paula Gomes, from the Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, for welcoming in my LC-MS studies. To Doctor Nuno Vale, from the Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, for his friendship since “ancient times”, for the collaboration in the biological studies and the help in the LC-MS characterization of the propolis extracts. To the Members of the Scientific Committee of the Doctoral Program of Chemistry and to all the Professors of Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, for their enthusiasm in teaching and for sharing their scientific knowledge during my undergraduate formation. To Federação Nacional de Apicultores de Portugal, for providing the propolis samples. To Professor Isabel Ferreira, from Escola Superior Agrária de Bragança, for her friendship, sympathy, encouragement and support during this work and for her valuable advices. To Eng. Sá Morais, from Escola Superior Agrária de Bragança, for his friendship, availability and precious help in the resolution of all kind of chromatographic problems. To Lillian Barros, from Laboratório de Química e Bioquímica Aplicada, for the help in the laboratory and the talks about MS characterization of phenolic compounds. For all the good moments in the lab and in our travels to scientific congresses. Above all, for her friendship and fellowship during the last 7 years. To all my colleagues from Laboratório de Química e Bioquímica Aplicada, past and present, for the pleasant moments spent in the Lab and for all the shared laughs, in particular to João, Ricardo, Sandrina, Rafaela, and to the more recent members Filipa, VI Ângela, Inês, Márcio, Carla, Eliane. Special thanks for Vânia, Hélder, Andreia, Joana and Sofia with whom I worked more directly, in the bee’s world, during these four years. To Anabela Sousa, Ana Paula Pereira, Ivo Oliveira, Daniela Correia and Sofia Meirinho start companions in the adventure of the PhD, for their friendship and for all the good moments. To all my friends outside the chemistry world, especially Marta, Humberto (and the little ones Gonçalo and Joana), for always being present in the good and bad moments, for the lifetime friendship, for the support, long talks dinners and weekends. A special thanks to my family. To my mother, for her unconditional love, friendship, support, encouragement, wise advices, for always help me in my life, believing in me and being by my side in all the moments. To my father, for his love, friendship and for always be present in my life given me encouragement and support. To my grandfather for the friendship and support. To my grandmothers and godmother, that are no longer here but are always present in my heart and who are an inspiration and an example of courage. Finally, to my husband Miguel, for his love, friendship, for giving me support and motivation in all moments, for always believing in me and being in my side in the good and bad moments. For all the fantastic moments, laughs and happiness in my life. To my unborn baby, who is so little but who I love so much, for giving me strength and courage to finish this work. VII VIII Abstract The characterization of Portuguese propolis from different continental and islands regions has as its main target the establishment of quality criteria and biological activity that enable the association of this beehive product with its phytogeographic origin, in an attempt to standardize the product and contribute for its commercial valorization. The results here described are structured according to seven resulting scientific publications: three published, two submitted for publication and two in final conclusion. To begin, the study focused on the evaluation of the physical and chemical properties of forty propolis samples from six Portuguese regions, particularly in terms of water, ashes, wax contents and colour index. Besides these parameters, the phenolic composition and the antioxidant activity were also assessed using spectrophotometric techniques. The results attested the existence of two different types of propolis within the six regions under study. The first, with an orange colour and a botanical origin in poplar, common in temperate regions, revealed a high content in phenolics which reflects in its high bioactivity. The second, with darker green colour was less rich in phenolics and generally less bioactive. Propolis is a matrix with high phenolic complexity so that the phenolic identification was achieved through electrospray ionization coupled to tandem mass spectrometry (ESI-MSn) and liquid chromatography with diode-array detection coupled to electrospray ionization tandem mass spectrometry (LC/DAD/ESI-MSn). The results allowed the identification of seventy six phenolic compounds, which included not only the typical phenolic acids and flavonoids found in propolis from temperate zones but also new compounds which have never been referred to in the literature. Within the new compounds, it was possible to found esterified and/or hydroxylated derivatives of flavonoids and unsual pinocembrin/pinobanksin derivatives containing a phenylpropanoic acid derivative moiety in their structure. In addition to these compounds, it was also possible to identify an unusual group of quercetin and kaempferol glycosides, described for the first time in propolis. In order to establish a correlation between the propolis samples and its geographical and botanical origin, the study was extended to the quantification of the phenolic fraction using reversed phase high-performance liquid chromatography (HPLC). The resinous extracts of Populus x canadensis and Cistus ladanifer, two potential floral sources for propolis production, were also considered. Flavonoids were predominant in all samples, with propolis from north, central coast and Azores archipelago presenting a richer composition in phenolic compounds, similar to those observed in poplar buds, while the central interior and south samples, revealed several kaempferol derivatives, resembling the Cistus ladanifer exudates. The compound kaempferol-dimethyl-ether can indeed be considered as a marker compound for botanical origin discrimination since it was found only in the last group of samples. IX The evaluation of the volatile fraction of propolis by gas chromatography coupled to mass-spectrometry (GC-MS), revealed a well diversify composition, with two hundred and one compounds detected, where terpenoids were predominante. The comparison with the essential oils extracted from the floral sources also allowed the association of Populus x canadensis and Cistus ladanifer volatiles with Portuguese propolis. Nevertheless, other Populus species as well as other plants like Juniperus genus may contribute to the resin in specific geographical locations. The electrochemical techniques, especially cyclic voltammetry and differential pulse voltammetry, are alternatives to the spectrophotometric methods in the evaluation of antioxidant activity, mainly due to its sensitive to the electronic transfer process. Its application in the current work showed
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