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Characterization of Pinus Spp. Needles by Gas Chromatography and Mass Spectrometry: Application to Plant-Insect Interactions

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Characterization of Pinus Spp. Needles by Gas Chromatography and Mass Spectrometry: Application to Plant-Insect Interactions EDUARDO MANUEL HIPÓLITO PIRES MATEUS Characterization of Pinus spp. needles by gas chromatography and mass spectrometry: Application to plant-insect interactions Dissertação apresentada para obtenção do Grau de Doutor em Ciências do Ambiente pela Universidade Nova de Lisboa, Faculdade de Ciências e Tecnologia LISBOA 2008 To my grandparents Celeste, João, Isabel and Manuel To my children Tomás and Vasco "Everything should be made as simple as possible - but not one bit simpler" Albert Einstein II Acknowledgements First of all I would like to express my gratitude to my supervisor Professor Rosa Paiva for giving me the chance of working with her in the last 20 years and for all her continuous guidance, stimulus, trust and support that promoted my scientific growth and made this work possible. Very special thanks go to my co-supervisor Professor Higuinaldo Chaves das Neves, who introduced me to the chromatographic science and whose suggestions, continuous encouragement, belief in my abilities, logistic and personal support are inseparable from my work and technical growth. I would like to express my deepest gratitude to Dr. Rui Rocha from LECO Instrumentos S.A., for all his valuable and constant support and for opening me the doors which made possible my work with GC × GC. To Professors João Tiago Mexia (CMA/FCT/UNL) and Manuela Oliveira (DM/UE) I express my deepest gratitude for all the support in the final stage of my work, guidance and supervision with the statistical analysis of my data. To Dr. Jitka Zrostlíková, from LECO Corporation, Prague, I would like to thank her technical assistance, support and patience during my staying at the Leco’s Application Laboratory Centre, in Prague, and her advices when I was giving my first steps with ChromaTof and GC × GC analysis. To Professor Fernando Santana and Professor Nunes dos Santos I would like to thank the valuable support at the departure of this process. To Professor Fernando Santana I am also thankful for the opportunities that he gave to me of working with him in research projects and where some of my technical skills have been developed. I am also very thankful to Professor Maria João Cabrita, from ICAM/UE, for allowing me to use their GC/MS for the resin acids analysis, Professor Philip Marriott, from RMIT, for the GC×GC analysis of resin acids, and Professor Joaquim Vital for supplying some of the terpene standards used. Special thanks go to Marco Gomes da Silva for his critically reading of this thesis, all the technical discussions, advices, constant support and company. III I am very grateful to Catarina José, for her work and help with the extraction, derivatization and analysis of resin acids, José Munhá for his help with the SDE work, Lena Farral for her old friendship, interesting discussions and statistical support, Ricardo Barata for the hard work with the retention indices determination, Evelyne Moura for all her help with the geographic and Apostiça data, Luz Fernandes for her technical support and constant availability to operate the GC-TOFMS, Professor Manuela Branco and Helena Santos for their support and help with the Thaumetopoea pityocampa tasks. I am also very grateful to Professor Zvi Mendel from the Department of Entomology/ARO, Israel for providing me the P. halepensis samples from Israel and Greece. This work was possible throughout the following funding: i) the Portuguese project Project PTDC/AGR-CFL/73107/2006, entitled "Analysis of the ongoing evolutionary process of an insect species causing public health concern" and ii) European Project QLK5-CT-2002-00852 entitled “PROMOTH - Global change and Pine Processionary Moth: a new challenge for integrated pest management”. A thanking thought is also due to DCEA/FCT/UNL, where I started and have always been working, which made this thesis possible. At last but not the least, I would like to thank my Mother and Father for the love, advices, constant encouragement and strong support that they always gave me, my Father and Mother- in-law for all the precious support and encouragement, Mena for all support and help with my children, my brother João and Ana for taking care of my kids many times and my brother Miguel for his advices. To my wife Alexandra who in the last leaps of my thesis has been my third (and sometimes fourth) arm, and during the last months have been a lonely mother, dealing with the kids and putting them to bed alone, my biggest and special gratitude for all her patience, understanding and support. For Tomás and Vasco I express my gratitude for their understanding and support, and apologies for my absence. At the end of my acknowledgements and being aware that many people have directly or indirectly contributed to this work, I would like to apologise all those that, for some reason, I have forgotten to thank. Thank you all. IV Sumário A processionária do pinheiro Thaumetopoea pityocampa (Lepidoptera: Notodontidae) é considerado o desfolhador do pinhal mais importante na região mediterrânica. A sua distribuição e dinâmica populacional é influenciada pelas espécies hospedeiras, mas os mecanismos responsáveis pela sobrevivência e êxito reprodutor das populações não são ainda conhecidos. A resistência e/ou susceptibilidade das espécies hospedeiras, poderá dever-se à composição química das agulhas, ou ao “bouquet” de voláteis emitidos pelas árvores hospedeiras. Neste contexto, a caracterização da composição química das agulhas de diferentes espécies de Pinus constitui uma ferramenta importante para a descodificação dos processos de selecção das espécies hospedeiras e consequente, dinâmica populacional de T. pityocampa. Assim, foi estudada a composição química das agulhas das espécies Pinus pinea, P. pinaster, P. halepensis, P. nigra, P. brutia, P. patula, P. radiata, P. taeda, P. elliotti, P. kesiya, P. sylvestris e P. eldarica, plantadas num arboretum na região de Abrantes. As fracções voláteis emitidas pelas agulhas foram amostradas por microextracção por fase sólida (SPME) e por destilação-extracção (SDE). Os ácidos resínicos foram extraídos por solvente e derivatizados antes de serem analisados. As amostras foram analisadas por cromatografia gasosa unidimensional (1D-GC), cromatografia gasosa multidimensional com sistema de transferência por corte (“heart cut”; MDGC), cromatografia bidimensional abrangente (GC × GC) e espectrometria de massa com recurso a diferentes analisadores de massa. Foi também avaliado o potencial de aplicação de espectrometria de massa, utilizando ionização de campo (field ionization; 1D-GC/FI-TOFMS) como modo de ionização. Os resultados obtidos mostraram que as capacidades analíticas da 1D-GC são parcialmente limitadas pelo poder separativo das colunas. A maior sensibilidade e a eliminação dos efeitos de distorção (“peak skewing”) dos espectros de massa colectados por analisadores de massa de tempo de vôo (TOF-”time-of-flight”), em conjunto com a aplicação dos algoritmos de desconvolução espectral e de detecção de picos (“mass spectral deconvolution” e “peak find”), permitiu a detecção de componentes em quantidades vestigiais, com espectros de V massa qualitativos e a extracção qualitativa dos espectros de massa individuais de compostos que co-eluem. Estes resultados conduziram a identificações mais seguras e, consequentemente, à melhoria dos resultados obtidos por 1D-GC/MS, com recurso a analisadores de massa de quadrupolo (1D-GC/qMS). A utilização da GC × GC resultou no aumento da eficiência de separação e da relação sinal- ruído (S/N) dos analitos, maximizando a qualidade dos espectros de massa adquiridos e melhorando a detecção e a identificação dos compostos analisados. A utilização de 1D- GC/FI-TOFMS permitiu a obtenção de informação rápida respeitante à gama de massas e à diversidade de massas moleculares existente nos extractos das diferentes agulhas de pinheiros. A análise por componentes principais permitiu diferenciar as diferentes espécies de pinheiros, de acordo com os seus componentes voláteis e o seu perfil em ácidos resínicos. A análise por mínimos quadrados parciais (PLS) permitiu referenciar os monoterpenos β-pineno, terpinoleno, limoneno+β-felandreno, mirceno, sabineno e os enantiómeros (-)-β-pineno e (+)- limoneno, após cromatografia quiral, como sendo os voláteis que melhor explicam as diferenças encontradas para os níveis de ataque registados, para as diferentes espécies de pinheiros. Não foi encontrada nenhuma relação significativa entre a composição das agulhas em ácidos resínicos e a sobrevivência das larvas de T. pityocampa. Contudo, a detecção de diterpenos da classe dos labdanos nas agulhas forneceu pistas que poderão vir a ser exploradas em trabalhos futuros. Este trabalho foi pioneiro na utilização de 1D-GC/TOFMS e de GC × GC/TOFMS para a análise da fracção volátil emitida por agulhas de pinheiros. A utilização de 1D-GC/TOFMS e de GC×GC/TOFMS, para a mesma amostra, permitiu detectar, respectivamente, 185 e 212 compostos voláteis, enquanto que a utilização de 1D-GC/qMS permitiu detectar 94. A análise, por GC×GC/TOFMS quiral, da composição da fracção volátil emitida pelas diferentes espécies de pinheiros permitiu a detecção de 422 compostos. VI Summary The pine processionary moth Thaumetopoea pityocampa (Lepidoptera: Notodontidae) is considered as the most destructive pine defoliator in the Mediterranean area. Host species appear to influence the distribution and population dynamics of the defoliator, but the mechanisms responsible for its performance are not yet understood. Tree resistance/susceptibility might be due to either
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