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ISOLATION and IDENTIFICATION of SECONDARY METABOLITES from the BRYOZOAN Cryptosula Zavjalovensis from HOKKAIDO, JAPAN

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ISOLATION and IDENTIFICATION of SECONDARY METABOLITES from the BRYOZOAN Cryptosula Zavjalovensis from HOKKAIDO, JAPAN LOVEILLE JUN AMARILLE GONZAGA ISOLATION AND IDENTIFICATION OF SECONDARY METABOLITES FROM THE BRYOZOAN Cryptosula zavjalovensis FROM HOKKAIDO, JAPAN UNIVERSIDADE DO ALGARVE FACULDADE DE CIÊNCIAS E TECNOLOGIA 2017 LOVEILLE JUN AMARILLE GONZAGA ISOLATION AND IDENTIFICATION OF SECONDARY METABOLITES FROM THE BRYOZOAN Cryptosula zavjalovensis FROM HOKKAIDO, JAPAN Erasmus Mundus MSc in Chemical Innovation and Regulation Mestrado Erasmus Mundus em Inovação Química e Regulamentação Trabalho efetuado sob a orientação de: Work supervised by: Prof. Isabel Cavaco (Universidade do Algarve) Prof. Helena Fortunato (Hokkaido University) UNIVERSIDADE DO ALGARVE FACULDADE DE CIÊNCIAS E TECNOLOGIA 2017 DECLARATION OF AUTHORSHIP ISOLATION AND IDENTIFICATION OF SECONDARY METABOLITES FROM THE BRYOZOAN Cryptosula zavjalovensis FROM HOKKAIDO, JAPAN I declare that I am the author of this work, which is original. The work cites other authors and works, which are adequately referred in the text and are listed in the bibliography. ____________________________________ Loveille Jun A. Gonzaga Copyright: Loveille Jun A. Gonzaga. The University of Algarve has the right to keep and publicize this work through printed copies in paper of digital form, or any other means of reproduction, to disseminate it in scientific repositories and to allow its copy and distribution with educational and/or research objectives, as long as they are non- commercial and give credit to the author and editor. I ACKNOWLEDGEMENTS I would like to extend my heartfelt gratitude to everyone who have been part of my Erasmus Mundus journey. The academic part of it might be concluded with this research work but the journey continues. This work wouldn’t have been possible without the immense help of such amazing people, so I would like to take this opportunity to thank: The European Commission and the EMMC-ChIR program for giving me this opportunity to pursue a relevant and timely international master’s program. Prof. Isabel Cavaco and Prof. Helena Fortunato for their unwavering guidance and supervision throughout this research process; for their time, effort and support. This research study wouldn’t have been possible without you. My family: Ma, Pa, and Vyrnj for being my huge source of encouragement, love and support. My Coca-Cola family, especially Ma’am Sha, Ate Rachel, and Sarrah for your all-out support. I wouldn’t be here without you. Shella Talampas, who was my big sister, friend, adviser, cook, counsellor all rolled into one, and; Wubshet Belay Abagero, my brother from another mother. Thank you for being not just great travel buddies but being my family during this journey. My awesome classmates: Dj Donn, Diana, Yemataw, Ester, Mulatu, Ana, Boryana, Kseniia, Miguel, Diego, Sufian, Zohreh, Pegah, and Erica. This is group is nothing but special. I am so lucky to have been part of this awesome group of friends. Prof. Emilio Tagliavini, and all our professors during our first year in Bologna. Thank you for your warm welcome and all the knowledge you have imparted. Grazie mille! Prof. Tatsufumi Okino, Kuya Julius, Annisa, Julie, and the entire Okino Laboratory for the guidance during my stay at Hokkaido University. Also, Samia Quaiyum for being a great colleague and good friend while I was in Sapporo. (Arigatou gozaimasu!) Prof. Maria da Conceição Monteiro André Oliveira and Ms. Ana Dias of the Mass Spectrometry Facility, Centro de Química Estrutural, Instituto Superior Técnico for their guidance and knowledge with the LC-MS and MS/MS analyses and interpretation; Prof. José Paulo da Silva for assisting with the LC-MS at UAlg; Prof. Vera Ribeiro for her immeasurable support and guidance with the cytotoxicity tests, and; Ms. Nataliya Butenko and everyone at the University of Algarve and Faro who helped a lot during my research year and made my stay in Portugal a memorable one. Muito obrigado! To be honest, this page wouldn’t be enough to thank everyone who have contributed and have been part of my journey. To everyone, maraming maraming salamat! Loveille II TABLE OF CONTENTS DECLARATION OF AUTHORSHIP ....................................................................................................... I ACKNOWLEDGEMENTS ................................................................................................................... II ABSTRACT ..................................................................................................................................... IV RESUMO ......................................................................................................................................... V LIST OF FIGURES ............................................................................................................................ VI LIST OF ABBREVIATIONS AND ACRONYMS ................................................................................... VIII 1. INTRODUCTION ...................................................................................................................... 1 1.1. THE IMPORTANCE OF RESEARCHING NATURAL PRODUCTS ........................................................................ 1 1.2. NATURAL PRODUCTS FROM MARINE ORGANISMS ................................................................................. 3 1.3. BRYOZOANS .................................................................................................................................... 5 1.4. NATURAL PRODUCTS FROM BRYOZOANS ............................................................................................. 8 1.5. CRYPTOSULA ZAVJALOVENSIS ........................................................................................................... 12 1.6. OBJECTIVES AND METHODOLOGY ..................................................................................................... 16 1.6.1. Separation by Solvent Extraction ..................................................................................... 16 1.6.2. Solid Phase Extraction and Reversed-Phase Chromatography ........................................ 16 1.6.3. Analysis by Liquid Chromatography-Mass Spectrometry (Electrospray Ionization) ....... 18 2. EXPERIMENTAL SECTION ...................................................................................................... 20 2.1. GENERAL EXPERIMENTAL PROCEDURES ............................................................................................. 20 2.2. SAMPLE COLLECTION ...................................................................................................................... 21 2.3. PRELIMINARY TESTS AT HOKKAIDO UNIVERSITY ................................................................................... 23 2.3.1. Solvent Extraction ............................................................................................................. 23 2.3.2. Solid Phase Extraction and Reversed-Phase Chromatography ........................................ 24 2.3.3. Cytotoxicity Screening ...................................................................................................... 24 2.3.4. Liquid Chromatography-Mass Spectrometry ................................................................... 26 2.4. ANALYSES AT THE UNIVERSITY OF ALGARVE ........................................................................................ 26 2.4.1. Solvent Extraction ............................................................................................................. 27 2.4.2. Solid Phase Extraction ...................................................................................................... 27 2.4.3. Liquid Chromatography-Mass Spectrometry ................................................................... 27 2.4.4. Tandem Mass Spectrometry ............................................................................................. 28 3. RESULTS AND DISCUSSION ................................................................................................... 29 3.1. PRELIMINARY TESTS ....................................................................................................................... 29 3.1.1. Cytotoxicity Screening ...................................................................................................... 29 3.1.2. Liquid Chromatography-Mass Spectrometry ................................................................... 32 3.2. RESULTS FROM THE UNIVERSITY OF ALGARVE ..................................................................................... 33 3.2.1. Liquid Chromatography-Mass Spectrometry ................................................................... 33 3.2.2. Tandem Mass Spectrometry ............................................................................................. 38 3.2.2.1 Peak m/z = 566 ............................................................................................................................................. 40 3.2.2.2 Peak m/z = 586 ............................................................................................................................................. 41 3.2.2.3 Peak m/z = 612 ............................................................................................................................................. 42 3.2.2.4 Peak m/z = 614 ............................................................................................................................................. 43 3.2.2.5 Peak m/z = 568 ............................................................................................................................................
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