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Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

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Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates by Joanna M. Wojnar A thesis submitted to the Victoria University of Wellington in fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry Victoria University of Wellington 2008 Abstract This study describes the isolation and structure elucidation of several known and 13 new compounds from New Zealand marine organisms. Furthermore, it describes the development of a digital mask program for the analysis of HSQC spectra of crude sponge extracts. This was used as a screening tool to identify secondary metabolite producers that warranted further analysis. As reports of metabolites from New Zealand nudibranchs are poorly repre- sented in the literature, a study of five New Zealand nudibranch species was undertaken. These coloured and seemingly undefended nudibranchs are known to concentrate or sequester toxic metabolites from their prey, facilitating rapid isolation and structure elucidation of these metabolites. This study resulted in the isolation of a variety of metabolite classes; two new compounds, 13α- acetoxypukalide diol (30) and lopholide diol (31) from the nudibranch Tritonia incerta, are described. Examination of the sponge Raspailia agminata resulted in the isolation of a novel family of partially acetylated glycolipids which contain up to six glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MS- guided isolation eventually led to the purification of agminosides A–E (145– 149). An unidentified sponge of the order Dictyoceratida was found to contain a new isomer (186) of the known sesterterpene variabilin. As variabilin-type compounds are predominantly found from sponges of the family Irciniidae, the unidentified sponge is most likely an irciniid. In addition, the sponge contained two prenylated quinones, one of which, 189, is a new isomer of a known sponge metabolite. The sponge Darwinella oxeata contained four new nitrogenous diterpenes of the aplysulphurane (rearranged spongian) skeleton, oxeatamide A (214), iso- oxeatamide A (215), oxeatamide A 23-methyl ester (216) and oxeatamide B (217). ii O O OMe OMe HO HO O O OH OH O O OAc O OAc O O 30 31 O HO O 13 OR O OR1 O OAc O A F HO O OH OH OAc HO OH O O AcO OAc E B AcO O O O OAc HO O OAc O D C O OAc HO AcO OAc OAc 145 R=Ac R1 = Ac 146 R=Ac R1 = H 147 R=H R1 = Ac 148 R=H R1 = H O HO O 13 OAc O OAc O OAc O A F HO O OH OAc O O AcO OAc B OH O OAc HO O OAc O D C O OAc HO AcO OAc OAc 149 iii OH O O O 186 O MeO O 189 O N N COOR COOH O COOH COOH 214 R = H 215 216 R = Me O H N N N COOH 217 iv To my grandfather, Prof. Dr. habil. Eng. Tadeusz Senkara, who would have been proud. v Acknowledgments It’s been an interesting few years, with the usual ups and downs of research, the frustrations and the excitements, the trials and triumphs, the brick walls and the eureka! moments. I would not have kept my sanity were it not for the great atmosphere and camraderie of the lab. Katie’s comment, when describing one of her first days in our group, epitomizes that spirit best: “I laughed till my face hurt!” I will start by thanking my supervisor, Peter Northcote, for his enthusiasm, excellent suggestions and encyclopedic knowledge of NMR and natural products that always amazed me (how can you tell it’s a linear furano-terpene from that dirty, crude proton?!). It has been a pleasure working for you. Secondly, I will mention my “other head”: Wendy Popplewell. I know we were called the two-headed monster, but it always amazed me how many people managed to get us confused. You have been a great friend and I have enjoyed our trips together (conferences and dive trips alike). Thank you for being my sounding-board, thank you for your suggestions, thank you for helping me un- tangle some of my sentences. Thank you to Greta Moraes, the Silica Queen, for taking me under your wing and teaching me how to run a “proper” column. I learned a lot from you, and enjoyed sharing a lab bench with you. Thank you to John Ryan, NMR Guy Extraordinaire. Where would we all be without your NMR skills and knowledge? Thank you for all your help throughout the years, for teaching me about NMR, and for your meticulous editing of my writing (even if I didn’t agree with you about Oxford commas). I must thank the other members of our group: Katie (“I’m sorry”) Dowle for useful discussions on the oxeatamides and good suggestions. Jonathan Singh, our token male in the last few years, for always being a gentleman. Mike Page for R. agminata identification and underwater photo. Catherine Gray and Jenn Hadfield for spending that summer screening sponges for us. Helen Woolner vi for doing sponge spicule mounts and working on our sample database. Izabela Pomer for always being ready to help and bringing us cake. Arab Spice (aka Mina Razzak) for venturing into the mammoth building of the Cambridge University library to get me papers. Stephen Mackey for the early work on R. agminata and the soft coral. To all the members of the lab, short or long term: you have been great friends and colleagues, making the lab a fun place to work in. There are of course lots of other people whose help and support has been invaluable. So thank you to Joanne Harvey for various synthetic chemistry discussions and for careful editing of my writing. Thank you to her synthetic chemistry group for letting me “borrow” reagents. Thank you to Brian Halton for setting a high standard. Thank you especially to Rob Keyzers for editing and lots of helpful questions and suggestions. To Almas Zayya: thank you for being my friend. A big thank you to the general staff of the school: Darren, Teresa, Gordon, Jackie, Sally, Lisa, Rhys, Alan, Manu, Scotty. Sometimes you may be unappreci- ated, but without you working in the background, research would be impossible. Thank you to Kate McGrath and Celia Simpson for dealing with the adminis- trative side of the degree. I would like to thank the National Institute of Water and Atmospheric Re- search (NIWA) for the prosaically named MNP1002 sponge, which turned out to be so interesting. I must also thank all the other divers who collected the sam- ples I worked on. They are Peter and Wendy of course, but also Toby Pugno, for making us laugh, and Kel Nairn, for being an all round excellent diver and boat companion. I must thank Kel as well for the underwater photo of D. oxeata. I also need to mention a diver I have never met: thank you to Ian Skipworth (http://www.ianskipworth.com/) for letting me use his beautiful nudibranch photos in this thesis. The School of Biological Sciences has kindly run a range of bioassays on my compounds: thank you to James Matthews, David Bellows, Ariane Chan, and Christopher Miller especially. A special thanks to James as well for helping me with the MALDI. Of course I must gratefully acknowledge my sources of funding: the Cancer Society Training Scholarship, the Curtis-Gordon Scholarship, the Marine Natural Products Scholarship and the VUW Completion Scholarship. I would like to thank my brother Maciek, firstly for writing the digital mask program. It has been an interesting exercise in communication between two vii people speaking completely different languages: chemistry and computer science. It taught me a lot. I would also like to thank him for always coming to the lab to ask for a ride home, for always being ready with an argument, for always asking why, for being a great brother. But most of all thank you for introducing me to Linux and LATEX—it has been a steep learning curve (sometimes seemingly vertical!) but without it Microsoft would have driven me mad during this write- up. Finally, thank you to the rest of my family. Words seem not enough, but I will try. Thank you for all the sacrifices you have made. Thank you for your unwavering support, thank you for your confidence in me, thank you for listening. Thank you for all those little things that mean so much: thank you for sending me home with food, buying me chocolate, fixing my leaky taps. I know I can always rely on you. viii Contents Abstract ii Dedication v Acknowledgments vi Contents ix List of Figures xiii List of Tables xvii List of Schemes xix 1 Introduction 1 1.1 Natural products as pharmaceutical leads .............. 1 Identifying lead compounds ..................... 3 1.2 Marine environment ......................... 5 The New Zealand marine ecoregion ................. 6 Marine natural products ....................... 6 Chemical defense in the marine environment ............ 7 Marine natural products in clinical trials .............. 9 1.3 Sponges ................................ 10 Microbial symbiosis in marine sponges ............... 10 1.4 Nudibranchs .............................. 12 Nudibranch defense .......................... 12 1.5 Research aims ............................. 14 1.6 Concluding remarks .......................... 14 2 Chemical Analysis of New Zealand Nudibranchs 15 2.1 Natural products from nudibranchs ................. 15 ix Terpenes ................................ 15 Macrolides ............................... 17 Peptides ................................ 19 2.2 New Zealand nudibranchs ...................... 20 2.3 Tritonia incerta ............................ 21 Metabolites isolated from T. incerta ................ 22 Cembranoid diterpenes from octocorals ............... 29 Concluding remarks .......................... 30 2.4 Dendrodoris denisoni ......................... 31 Metabolites isolated from D. denisoni ................ 32 Drimane sesquiterpenes ........................ 32 Concluding remarks .......................... 33 2.5 Aphelodoris luctuosa ........................
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