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Studies in Marine Natural Products

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Studies in Marine Natural Products STUDIES IN MARINE NATURAL PRODUCTS A thesis submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry at the University of Canterbury by Warren J. MacLean ucvUNIVERSITY OF CANTERBURY Te Whare Wananga o Waitaha CHRISTCHURCH ;,..'EW ZEALAND University of Canterbury Christchurch, New Zealand November 2005 ENCiS IRARYESIS ABSTRACT ABSTRACT The marine environment continues to be a prolific source of structurally diverse and biologically active natural products. Over the past few decades both macro­ and micro-organisms have been extensively studied for such compounds. Annual reviews are dominated by novel compounds isolated from marine sponges, even though investigations have more recently been focused on micro-organisms. After decades of research into the development of marine natural products as potential pharmaceuticals, many marine compounds now feature prominently in current pre-clinical and clinical trials. This thesis represents a continuation of work in the area of isolation and structural elucidation of novel and/or biologically active natural products from both marine macro- and micro-organisms. The four novel C31 polyacetylenic compounds 2.23, 2.24, 2.25 and 2.26 were isolated as the major components of the cytotoxic extract of the New Zealand manne sponge Rhabderemia stelletta, using bioassay-guided separation techniques. However, these structures were not unambiguously assigned due to the low resolution of the NMR signals associated with the long-chain alkyl protons and carbons. Elucidation was also hindered by compound degradation during structural analysis. The partial structures were identified via mass spectrometry and NMR spectroscopy and comparison of structural data for similar compounds reported in the literature. ABSTRACT II The novel pteridines 3.13 and 3.15 were isolated as the maJor and mmor . components, respectively, from the cytotoxic organic extract of an as yet unidentified Antarctic marine sponge 02WM01-33. Identification was achieved using mass spectrometry and NMR spectroscopy, and comparison of these data to those published in the literature for similar structures. Although pteridines are distributed widely throughout nature, 3.13 and 3.15 represent a chemically interesting group of compounds as they possess a mono-oxygenated methyl side chain, which has not been previously reported among any of the naturally occurring pteridines. The novel hydantoin compound 4.8 was isolated as the major biologically active component of the organic extract of the Antarctic marine sponge Suberites sp. using microtitre plate P388 assay guided fractionation. The relative stereochemistry of 4.8 was determined using lD-NOESY experimental data. This work represents the first isolation of the hydantoin 4.8 as a natural product from a marine sponge. This compound has been reported previously in the literature, but only as a synthetic product. The two novel anthraquinone compounds 5.35 and 5.41 were isolated as minor components of the cytotoxic organic extract of the Antarctic marine sponge­ derived fungus Aspergillus sp., along with the three known anthraquinones 5.32, 5.34 and 5.40. This series of work revealed several areas in the literature that require revising: these include, (i) the compounds 5.31 and 5.41 were both reported as a new metabolites in 1985 and 2003, respectively, however, both compounds had been previously isolated and reported in 1966; (ii) the compound 5.36 requires the correct structural assignment in the literature; and finally, (iii) the compound 5.35 has two isomeric structures reported in the AntiMarin database, however, neither of these structures match the experimental 1 H NMR data supplied by the author of the database. The three novel compounds 6.9, 6.13 and 6.15 were isolated from the organic extract of an Antarctic marine sponge-derived fungus Ulocladuim sp., along with the previously reported compounds 6.6, 6.7 and 6.16. These compounds were ABSTRACT iii identified using NMR spectroscopy and mass spectrometry. This work highlights an inconsistency in the literature regarding the structural assignment of two carbons for the known compound 6.16. The structural assignment of these carbons was confirmedby the independent isolation of 6.16 by another member of the Marine Group. ACKNOWLEDGEMENTS IV ACKNOWLEDGEMENTS First and foremost I must extend my gratitude to my supervisors, Professors Murray Munro and John Blunt, for their guidance, support and encouragement throughout my years of study in the Marine Group. Recognition must go to Gill Ellis for all of her expert help in sample identification and storage of samples collected in Antarctica, not to mention the hundreds of biological assays run on sample extracts. Thanks to the technical staff of the Chemistry department which include; Bruce Clarke for mass spectrometry, the lads in the mechanical workshop for their help from time to time. Rob McGregor for his glassblowing skills and the multi talented attributes of Wayne Mackay. Thanks must go to Nie Cummings of the School of Biological Sciences Department forwork relating to the culturing of fungal samples. Many thanks to the team at the Australian Institute of Marine Sciences (AIMS) and PharmaMar, for the opportunity to travel to Antarctica as a member of K059. To Nicole Webster, Andrew Negri, Carsten Wolff, Chris Battershill, Ren Naylor, James Monkovitch and Steve Mercer, thanks for the deep water sponge, fungal and bacterial samples that set me free and the chance to get naked and wet under the ice. Thanks to the past and present members of the marine group, Scott Bringans, Tim Harwood, Annabel Murphy, Marie Squire, Sonia van der Sar, Dr Sylvia Urban, your help has been greatly appreciated, above all Dr Sean 'seabass' Devenish for his expert advice during many late night structural elucidation sessions, and for an ACKNOWLEDGEMENTS V extra pair of hands when surgery was required on the HPLC. Also, for running additional mass spectrometry and of course most importantly, helping to develop the 'weapon of mass destruction' (patent pending) not to mention the high jinks that made life bearable. I could not have asked for a better Jab buddy, you have helped me along through my PhD journey more than you can imagine ..... cheers! A special thank you must also go to Sarah Rickford and her 'eagle eyes' for proof reading this thesis in preparation for its submission. Thanks to PharmaMar for financial support through the firstfew years of my PhD, and to Southern Gas Services Ltd for financial support during the final years of my PhD. Thanks to David Mcdonald, Nicolas Heaphy and all the other people that have long since left, this list would be fartoo long to write out in full,thank you for the opportunity of getting to know you. To my dearly departed Grandma, who never quite understood what I did at University but took great pleasure at showing me offto her closest friends, sorry you didn't get to see me graduate, but I know you'll be watching from your lazy boy in the sky. Finally, to my wife Melissa, your support, patience strength and understanding have made my long years of study at Canterbury University a pleasure. Your amazing adaptive ability never ceases to amaze me. Thank you for your continued love and support. TABLE OF CONTENTS VI TABLE OF CONTENTS ABSTRACT i ACKNOWLEDGEMENTS iv TABLE OF CONTENTS Vl LIST OF TABLES xiii LIST OF FIGURES xv LIST OF ISOLATION SCHEMES XX ABBREVIATIONS xxi CHAPTER 1: INTRODUCTION 1 1.1 Introduction 1 1.2 What are Natural Products? 1 1.3 Some Famous Natural Products 3 1.4 Why Search the Marine Environment 7 1.5 Recent Advances in the Discovery of Natural Products JO 1.6 WhyContinue Prospecting for Biologically Active Natural Products? 11 1.7 The Phylum Porifera, an Overview 18 1.8 Marine Fungi, an Overview 22 1.9 Antarctic Sponges 23 I.JO TheCurrent State of Play 28 1.11 TheAim of this Thesis 36 CHAPTER 2: ISOLATION OF COMPOUNDS FROM THE NEW ZEALAND MARINE SPONGE Rhabderemia stelletta (OJMNP0729) 37 2.1 General Introduction 37 TABLE OF CONTENTS Vil 2.2 Introduction 44 2.3 Extraction of Marine Sponge Rhabderemia stelletta 44 2.4 Chromatographic Isolation of Bioactives 46 2.4.1 Reversed Phase (C,s) Flash Chromatography of the Organic Extract of the Marine Sponge R. Stelletta 46 2.4.2 Normal Phase (DIOL) Chromatography of Fraction wj m12-312 47 2.4.3 Reversed Phase (C,s) Semi-preparative Chromatography of Fractions wj m12-701 to wjm12-703 47 2.5 Structural Elucidation of Compounds Isolated from Rhabderemia stelletta 48 2.5.1 Structural Elucidation of 2.23 48 2.5.2 Structural Elucidation of 2.24 58 2.5.3 Structural Elucidation of 2.25 66 2.5.4 Structural Elucidation of 2.26 73 2.6 Biological Activity 80 2.7 Concluding Remarks 80 2.8 Summaryof Isolation 83 CHAPTER 3: ISOLATION OF COMPOUNDS FROM AN UNIDENTIFIED ANTARCTIC MARINE SPONGE (02WMOJ-33) 84 3.1 General Introduction 84 3.2 Introduction 88 3.3 Extraction of the Unidentified Antarctic Marine Sponge (02WM01-33) 89 3.4 Chromatographic Isolation of Bioactives 91 3.4.1 Reversed Phase (C,s) Flash Chromatography of the Organic Extract of 02WM01-33 91 3.4.2 Reversed Phase (C,s) Semi-preparative HPLC Chromatography of Fraction wjm20-203 91 3.5 Structural Elucidation of Compounds Isolated from 02WM01-33 92 3.5.1 Structural Elucidation of 3.13 92 TABLE OF CONTENTS Vlll 3. 5. 2 Structural Elucidation of 3.15 98 3.6 Biological Activity 102 3.7 Concluding Remarks 103 3.8 Summary of Isolation 104 CHAPTER 4: ISOLATION OF COMPOUNDS FROM THE ANTARCTIC MARINE SPONGE Suberites sp. (02WM01-46) 105 4.1 General Introduction 105 4.2 Introduction 107 4.3 Extraction of the Antarctic Marine Sponge Suberites sp.
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