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SECONDARY METABOLITES COMPOSITION and GEOGRAPHICAL DISTRIBUTION of MARINE SPONGES of the GENUS Dysidea

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SECONDARY METABOLITES COMPOSITION and GEOGRAPHICAL DISTRIBUTION of MARINE SPONGES of the GENUS Dysidea COMPONENT 2C – PROJECT 2C4 Bioprospection & Active Marine Substances Training of Pacifi c students June 2009 MASTER THESIS SECONDARY METABOLITES COMPOSITION AND GEOGRAPHICAL DISTRIBUTION OF MARINE SPONGES OF THE GENUS Dysidea Author: Mayuri Chandra Photo: ©IRD – Eric FOLCHER Photo: ©IRD The CRISP Coordinating Unit was integrated into the Secretariat of the Pacifi c Community in April 2008 to insure maximum coordination and synergy in work relating to coral reef management in the region. The CRISP Programme is implemented as part of the policy developped by the Secretariat of the Pacifi c Regional Environment Programme to contribute to the conservation and sustainable development of coral reefs in the Pacifi c. he Initiative for the Protection and Management of Coral Reefs in the Pacifi c (CRISP), T sponsored by France and prepared by the French Development Agency (AFD) as part of an inter-ministerial project from 2002 onwards, aims to develop a vision for the future of these unique eco-systems and the communities that depend on them and to introduce strategies and projects to conserve their biodiversity, while developing the economic and environmental services that they provide both locally and globally. Also, it is designed as a factor for integration between developed countries (Australia, New Zealand, Japan, USA), French overseas territories and Pacifi c Island developing countries. The CRISP Programme comprises three major components, which are: Component 1A: Integrated Coastal Management and watershed management - 1A1: Marine biodiversity conservation planning - 1A2: Marine Protected Areas CRISP Coordinating Unit (CCU) - 1A3: Institutional strengthening and networking Programme manager : Eric CLUA - 1A4: Integrated coastal reef zone and watershed management SPC - PoBox D5 Component 2: Development of Coral Ecosystems 98848 Noumea Cedex - 2A: Knowledge, monitoring and management of coral reef ecosytems New Caledonia - 2B: Reef rehabilitation Tel : (687) 26 54 71 - 2C: Bioprospection and marine active substances Email : [email protected] - 2D: Development of regional data base (ReefBase Pacifi c) www.crisponline.net Component 3: Programme Coordination and Development - 3A: Capitalisation, value-adding and extension of CRISP Programme activities - 3B: Coordination, promotion and development of CRISP Programme COMPONENT 2C Bioprospection and Marine Active Substances PROJECT 2C-1 : Legal Output - Proposals for an improvement of legal framework in Pacifi c countries for insuring a better benefi t-sharing in bioprospection Component leader : Cécile DEBITUS PROJECT 2C-2: IRD - UMR 152 Taxonomic Output - Improvement of scientifi c knowledge of reef benthic inverte- University of Paul Sabatier brates Toulouse II Faculty of Sciences 31062 Toulouse cedex 9 PROJECT 2C-3 : France Technological Output - Screening and identifi cation of Marine Active Subtances Tel : (33) 5 62 25 98 11 Fax : (33) 5 62 25 98 02 PROJECT 2C-4 : [email protected] Capacity building Output - Training of Pacifi c people in the fi eld of bioprospection This training was eff ective thanks to the fi nancial support of the following agencies: SECONDARY METABOLITES COMPOSITION AND GEOGRAPHICAL DISTRIBUTION OF MARINE SPONGES OF THE GENUS DYSIDEA By Mayuri CHANDRA A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science School of Biological & Chemical Sciences, Faculty of Science, Technology & Environment, The University of the South Pacific Suva, Fiji Islands June, 2009 “Man masters nature not by force but by understanding. This is why science has succeeded where magic failed: because it has looked for no spell to cast on nature.” - JACOB BRONOWSKI ACKNOWLEDGEMENT This project would not have been completed without the help and support of a number of people. My heartfelt acknowledgement goes to the following people and organisations: This work is part of the C2 component of the Coral Reef Initiative in the South Pacific (CRISP) project and funded by the Agence Française de Développement. The research grant for the component completed in Fiji was obtained from the Government of Taiwan. This project was also partly completed in New Caledonia and France, and it was funded by the Government of France with the initiative of the Embassy of France in Fiji and the Centre Régional des Œuvres Universitaires et Scolaires (CROUS). I am grateful to my supervisors, Professor Subramaniam Sotheeswaran and Associate Professor Sadaquat Ali, for giving me an opportunity to pursue my interest in the field of Natural Products research. This project was a good learning ground for me, which provided great experiences along the way. Furthermore, most of this project was completed in New Caledonia and France, and my sincere gratitude goes to my external supervisors, Dr Sylvain Petek, Dr Isabelle Bonnard and Dr Bernard Banaigs for their guidance. Dr Sylvain Petek, my supervisor in New Caledonia, has been a great support and mentor. The research team at the Institut des Recherche et Développement (IRD – Noumea, New Caledonia) was really friendly and helped me greatly to adjust to the new environment and language. Dr Isabelle Bonnard at the Centre de Phytopharmacie, University of Perpignan via Domitia (Perpignan, France), was always there for me whether I had any project- related or personal problems. She is a great mentor and I was able to have a good learning experience, which broadened my knowledge of research. Thanks to the staff and students of Centre de Phytopharmacie, I was also able to explore France to some extent, and the experience was amazing. The sponge samples used in this study were obtained by diving; hence I would like to thank the dive team of the IRD Centre of Nouméa, New Caledonia, for harvesting the sponges. Furthermore, we highly appreciate the governments of New Caledonia, i Vanuatu, Solomon and Fiji Islands for permitting us to collect our samples in their countries, and the Fisheries Departments of these countries for their help and assistance during the collections. I would also like to thank Dr Cécile Debitus, Pierre Pério, and Camille Durand at the Université Paul Sabatier, Toulouse, France, as well as Professor Valeria D’Auria at the University of Naples, Italy, for providing us with technical support in our sample analysis. The anti-microbial testing was carried out partly at the IRD – Noumea, and partly at the Institute of Applied Sciences (IAS), University of the South Pacific. I would like to thank the microbiology team at the IAS (especially Pritesh, Kavita, Girish Lakhan, and Mr. Klaus Feussner) for providing the necessary resources for completing this part of the project. I can not forget my family and friends for their never-ending support in the duration of my project. For all the hours spent in the laboratory, there was always someone to give company or talk to when things became tensed, confusing, or just tiresome. My thanks goes to my friends Nirul, Ardarsh, Roselyn, Joslin, Sujlesh, Riteshma, and the technical staff of the Faculty of Science and Technology, USP, Suva. Kirti and Shital helped me quite a lot during my stay in France. We had a great time together. Finally, the support, blessing and sacrifice of my parents, Mr. Vinod Chandra and Mrs. Kala Chandra, have given me the strength to stay focused on my path to complete this project. Thank you, vinaka vakalevu, and merci beaucoup to everyone who has contributed to this project in one way or another. ii ABSTRACT Dysidea species – Lamellodysidea herbacea, Dysidea arenaria, and Dysidea avara – from New Caledonia were chemically screened to identify the chemical constituents of these sponges. Each species exhibited a specific profile, thus grouping the three species chemically together in distinct taxa. The screening also identified the presence of three different chemical types of L. herbacea present within the same region, New Caledonia. The pattern of occurrence of polybrominated diphenyl ethers (PBDE) in L. herbacea was also mapped for distant geographical sites, which included New Caledonia, Vanuatu, Fiji Islands, Solomon Islands, Moorea Island in French Polynesia, and Mayotte. Comparison and analysis of the chemical fingerprints shows that all the samples belong to the bromo-chemotype of compounds, and similarities and differences exist within the same species in different geographical locations. L. herbacea was further explored for compound isolations and characterization to verify the chemical fingerprints of these sponges. Spectroscopic and chemical analyses confirmed the presence of PBDEs in the L. herbacea analyzed. Eight different PBDEs have been identified, where four of these (compounds 2, 6, 7, and 8) have been successfully isolated and characterized. Crude extracts of the Dysidea sponges were also tested for activity against the fungi Cryptococcus neoformans and Candida albicans. Most extracts were active against Cr. neoformans hence confirming the hypothesis that the action was due to the inhibition of the proper functioning of the protein farnesyl transferase (PFT), which is an essential enzyme in the metabolism of this fungus. Ca. albicans is able to survive even without PFT. Since Plasmodium falciparum (the malarial parasite) is also dependent on PFT for survival, this anti-fungal test is being developed to be used as a pre-test for anti-plasmodial studies. iii SOMMAIRE L’étude et la comparaison des profils chimiques chez Lamellodysidea herbacea, Dysidea arenaria, et Dysidea avara ont été menés afin d’identifier les métabolites secondaires
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