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NOVEL SECONDARY METABOLITES FROM SELECTED COLD WATER MARINE INVERTEBRATES By DAVID ELLIS WILLIAMS B.Sc.Hons, King's College, University of London, 1983 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in THE FACULTY OF GRADUATE STUDIES (Department of Chemistry) We accept this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA October 1987 ® David Ellis Williams, 1987 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the head of my department or by his or her representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department The University of British Columbia 1956 Main Mall Vancouver, Canada DE-6(3/81) ABSTRACT. A study of the secondary metabolism of two nudibranchs and one soft coral has led to the isolation of eighteen new and two known secondary metabolites. The structures of all compounds were determined by a combination of the interpretation of spectral data, chemical degradations and interconversions, and single crystal x-ray diffraction analysis. The British Columbian dorid nudibranch Diaulula sandiegensis yielded two new steroidal metabolites, diaulusterols A (41) and B (42). The 25-(3-hydroxybutanoate) residue of diaulusterol A (41) and the 2a,3a-diol array of both 41 and 42 are not commonly encountered in naturally occurring steroids. Both metabolites exhibited considerable antibacterial and antifungal activity. Steroid 41 exhibited fish antifeedant activity. The relative concentration of 4.1 and 42 in the skin extracts of D_. sandiegensis appears to be related to the animals' seasonal abundance. Extracts of the British Columbian soft coral Gersemia rubiformis yielded a series of ten diterpenes possessing cembrane f170-175), pseudopterane (167-169) and gersolane (176) carbon skeletons. The structure of an eleventh diterpene remains unresolved. In addition, the structure of a degraded diterpene possessing a 13-membered ring (122) is tentatively proposed. G. rubiformis represents the first example of a soft coral to - ii - yield pseudopterane diterpenes. The organism is the first to contain cembrane, pseudopterane and gersolane metabolites, a fact which has biogenetic implications. Two new sesquiterpenes were also isolated. Tochuinyl acetate (165) and dihydrotochuinyl acetate (166) represent the first examples of cuparane sesquiterpenes to be isolated from a soft coral. A biogenesis is proposed. Metabolite 166 exhibited fish antifeedant activity. Investigations of Gersemia rubiformis collected in Newfoundland waters revealed that the secondary metabolism differed from west coast specimens. The isolation of the new unstable sesquiterpene (+)-/?-cubebene-3-acetate (178) resulted. Skin extracts of the dendronotoid nudibranch Toquina tetraquetra were examined in an attempt to correlate its feeding dependency and lack of predation to the presence of allomones. Metabolites 165. 166. 170. 179 and the new butanoate diterpene 180 could be traced to the coelenterates which make up the animal's diet. Tochuinyl acetate (165). dihydrotochuinyl acetate (166) and rubifolide (170) were previously found in extracts of Gersemia rubiformis. Ptilosarcenone (179) has been reported as one of the major metabolites of the sea pen Ptilosarcus 213 gurneyi . The exact origin of a sixth metabolite, pukalide (£1) , remains unknown. It is proposed that Tochuina tetraquetra selectively sequesters dietary metabolites for defensive purposes. - iii - Table OJL Contents. Page # Abstract ii List of Figures vi List of Schemes ix List of Tables x Acknowledgements xii Abbreviations xiii I. Introduction 1 A. Overview 1 B. Natural Product Chemistry 1 C. Marine Natural Products 4 II. Nudibranchs 10 A. introduction: Nudibranch Zoology 10 B. Nudibranch Defenses: Evolutionary and Ecological Influences 13 C. The Chemistry of Nudibranchs 19 III. Secondary Metabolites from the Dorid Nudibranch, Diaulula sandiegensis (Cooper, 1862) 23 A. Introduction 23 B. Isolation and Structural Elucidation 25 C. Biological Activities of Diaulusterol A (11) and Diaulusterol B (12) 46 D. Further Observations and Discussion 47 - iv - IV. Soft Corals 52 A. Introduction: Alcyonacean Zoology 52 B. Symbiotic Associations Between Alcyonarians and Algae (Zooxanthellae): Implications to the Origin of Isolated Metabolites 55 C. Why The Interest: The Biological and Ecological Significance of Some Coelenterate Metabolites 58 D. Chemistry of Soft Corals and Alcyonarians In General ..... 61 E. Review of the Chemistry of the Family Nephtheidae 70 V. Secondary Metabolites from the Soft Coral, Gersemia rubiformis (Ehrenberg, 1834), and the Dendronotoid Nudibranch, Toouina tetraquetra (Pallas, 1788) 78 A. Introduction 78 B. Isolation of the Metabolites 83 C. Structural Elucidation and Related Studies . 87 (i) Sesquiterpenes 165 and 166 87 (ii) Pseudopterane diterpenoids, 167-169 . 105 (iii) Cembrane diterpenoids, 170-175 125 (iv) New carbon skeletal metabolites, 176-177 . 175 (v) Sesquiterpene 123. 192 (vi) Pukalide (£3J 206 (vii) Briarein diterpenoids, 179 and 180 .... 206 D. Biological Activities 210 E. Biosynthetic Postulates 212 F. Further Observations and Discussion 216 VI. Experimental 224 VII. Bibliography 258 - v - LAPt Of Figures. Figure Page # 1 Phylogenetic classification of two nudibranchs . 11 2 Typical cryptobranch dor id nudibranch ...... 12 3 13C NMR spectrum of diaulusterol A (H) 26 4 NMR spectrum of diaulusterol A (11) 27 13 5 C NMR spectrum of diaulusterol A triacetate (13J 29 6 *H NMR spectrum of diaulusterol A triacetate (12) 31 7 Contour plot of 2D-HETC0R NMR spectrum of diaulusterol A triacetate (12.) 33 8 Comparison of the coupling constants of 41 and 11 with models 15. and 49-52 38 9 *H NMR spectrum of diaulusterol B (12) 44 10 "^H NMR spectrum of diaulusterol B diacetate (52.) 46 11 Structure of a typical alcyonarian 53 12 Phylogenetic classification of the soft coral, Gersemia rubiformis 54 13 *H NMR spectrum of tochuinyl acetate (165) ... 88 14 13C NMR spectrum of tochuinyl acetate (165) ... 89 15 Contour plot of 2D-HETCOR NMR spectrum of tochuinyl acetate (lfL5J 90 16 Gated decoupled JC NMR spectrum of tochuinyl acetate (1£5J 94 17 SINEPT NMR spectra of tochuinyl acetate (165) . 96 - vi - 18 H NMR spectrum of dihydrotochuinyl acetate (1£6J 101 19 C NMR spectrum of dihydrotochuinyl acetate (1££) 102 20 13C NMR spectrum of gersemolide (167) 107 21 DEPT NMR spectra of gersemolide (167) 108 22 *H NMR spectrum of gersemolide (167) 109 23 Computer generated perspective drawings of gersemolide (167) 113 24 1H NMR spectra of A4,5Z, A7,17-isogersemolide 119 25 1H NMR spectrum of A4'5E, A7,17-isogersemolide (lfi&) 121 26 13C NMR spectrum of A4,5E, A7,17-isogersemolide (169) 122 27 ^ NMR spectrum of rubifolide (170) ....... 126 28 13C NMR spectrum of rubifolide (170) 127 29 400MHz ^-H NMR spectrum of rubifolide (170) . 136 30 400MHz lanthanide shifted 1H NMR spectra of rubifolide (12H) 137 31 *H NMR spectrum of epilophodione (171) 146 32 13C NMR spectrum of epilophodione (171) 147 33 ADEPT NMR spectra of epilophodione (171) .... 148 34 1H NMR spectrum of isoepilophodione A (122) . • . 151 35 13C NMR spectrum of isoepilophodione A (172) . 152 36 *H NMR spectrum of isoepilophodione B (173) . 155 37 Low temperature 1H NMR spectra of isoepilophodione B (122.) 157 38 NMR spectrum of isoepilophodione C (174) . 160 - vii - 39 C NMR spectrum of isoepilophodione C (174) . 161 40 1H NMR spectrum of rubifol (175) 165 41 13C NMR spectrum of rubifol (125.) 166 42 APT NMR spectrum of rubifol (1751 ........ 167 1 43 H NMR spectrum of rubifol (175) in CgDg .... 171 44 "*"H NMR spectrum of unknown diterpene 172 45 Proposed structures for unknown diterpene .... 174 46 XH NMR spectrum of gersolide (176) 176 47 Computer generated perspective drawing of gersolide (176) 178 48 1H NMR spectrum of rubiformate (177) 182 49 13C NMR spectrum of rubiformate (177) 183 1 50 H NMR spectrum of rubiformate (177) in CgD6 . 191 51 C NMR spectrum of ( + ) -y?-cubebene-3-acetate (1781 194 52 *H NMR spectrum of (+)-y?-cubebene-3-acetate (178) 196 53 1H NMR spectrum of the mixture of dihydro epimers 192 and 193 198 54 1H NMR spectrum of the mixture of dihydro epimers 192 and 193 in CgDg 201 55 1H NMR spectrum of the butanoate 1M 207 56 Biogenetic speculation for (+)-/?-cubebene-3-acetate (12&) 216 - viii - ULs_t QL Schemes. Scheme Page # 1 Biogenetic proposal for tochuinyl acetate (165) and dyhydrotochuinyl acetate (166) .... 213 2 Biogenetic proposals for the cembrane, pseudopterane, gersolane and degraded 13-membered ring diterpenoids, 167-177 214 3 Biogenetic proposal for (+) -fj-cubebene-3-acetate (12SJ 217 - ix - List ££ Tables. Table Page # 1 13C NMR data comparison of 41 and 44 32 2 1H NMR data comparison of 41 and 45. 32 3 *H NMR data comparison of the steroidal methyl resonances of Air 45_, A3 and 42 35 13 4 C NMR data comparison of the steroidal methyl resonances of 41f 4£ and A3 36 5 Partial *H NMR assignments for diaulusterol A (11), diaulusterol B (42), triacetate 41 and diacetate 5_3_ 40 6 Partial C NMR assignments for diaulusterol A (41) and triacetate 42 42 7 Results of in vitro antibiotic assays for the steroidal metabolites, diaulusterol A (41) and diaulusterol B (42) 47 8 *H NMR data comparison of 165 and 181 91 9 13C NMR data comparison of 165 and 1£1 92 10 1H NMR assignments for tochuinyl acetate (165) and dihydrotochuinyl acetate (166) 99 11 13C NMR assignments for tochuinyl acetate (1£5_) and dihydrotochuinyl acetate 166 100 12 1H NMR data comparison of 166. 183 and 184 ... 104 13 13C NMR data comparison of 166. 132. and 184 . 105 14 13C NMR assignments for gersemolide (167) and 169.
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