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Acknowledgements 1would like to express my sincere gratitude to Professor William A. Ayer for the guidance, patience, faith, and encouragement he provided me during the course of my studies at the University of Alberta. 1am grateful to Professor M. Adjangba for his encouragement to continue my studies and to the "Université du Bénin au Togo" for financial support during my undergraduate studies in Canada. 1would like to extend my gratitude to Dr. L. M. Browne for her help in learning various fungal culturing techniques and for her help in the preparation of this thesis. 1 sincerely thank Drs. S. Attah-Poku, P. Setiloane, and H. Wynn for their help in editing the thesis. 1wish to thank: Dr. D. Ward for his valuable suggestions, the members of the research group for their helpful assistance, Dr. T. Nakashima, Mr. T. Brisbane, and Mr. G. Bigam for their helpful contribution in determining the lH NMR and DC NMR spectra, Mr. L. Harrower and Mr. J. Olekszyk for the determination of the mass spectra, Mr. R. N. Swindlehurst and his staff for the determination of FTIR spectra, Mrs. A. Szenthe for growing the Arthrosporae fungus and for the biological tests, Julie for the proofreading of this thesis, Mrs. L. Ziola for her typing of the manuscript, and The Department of Chemistry, University of Alberta, for financial support. My sincere gratitude to Mrs. Dorothy Ayer and her family, and to my many friends: Celine, Gertrude, Pauline, Hossein, Azim, Joe, and Pancho who, through their friendship and moral support have helped me to successfully complete this work. Finally, 1express my deep gratitude to Amber for her love. vii
Abstract Acknowledgements List of Tables List of Figures List of Schemes 1. Introduction II. Discussion Arthrosporone (20) Anhydroarthrosporone (21) TABLE Of CONTENTS Structure and Stereochemistry of Arthrosporone (20) Arthrosporol (23) Dehydroarthrosporodione (23) 4-0-Acetylarthrosporol (24) Tetracyclic ether (25) Isocyclohumuladiol (26) III. Experimental Growth of the fungus Extraction of the crude metabolites Isolation of arthrosporone (20). tetracyclic ether (25) and isocyclohumuladiol (26) Isolation of anhydroarthrosporone (21) Isolation of dehydroarthrosporodione (23) and O-acetylarthrosporol (24) Study of the Biological Activity of Arthrosporae Metabolites using a Paper Disk Diffusion Method Bibliography Appendix viii Page v vii x IX XI 13 14 25 45 58 72 77 79 82 92 93 94 96 100 103 127 133 141
Page 1: THE UI\JIVERSITY OF ALBERTA ANTIFUN
Page 4 and 5: Abstract A fungus observed to inhib
Page 8 and 9: LIST Of TABLES Table Page 1. Taxono
Page 10 and 11: LIST OF SCHEMES Scheme Page 1. ln v
Page 12: of the landscape. C. ulmi. causal a
Page 15 and 16: Fig. 1. Photo of Arthrosporae fungu
Page 17: 8 9 10 11 7 OH RI =O. Rl =
Page 21 and 22: 18 OH anhydroarthrosporone 12 11. a
Page 24 and 25: major components as evidenced by ex
Page 26: The IH-NMR spectrum of arthrosporon
Page 31 and 32: (C) 1 1 CH) o OH ml z 252 IM-) CH)
Page 33 and 34: 28 HO OH 30 32 OH OH o o o 29 33 31
Page 35: (C) o Àmax (calcdl 231 nm; obs. 23
Page 39 and 40: expected to undergo a retro-aldol c
Page 41: The HRMS of 41 exhibits a base peak
Page 49 and 50: molecular formula was established a
Page 55 and 56: downfield proton (H-4) at 0 3.84. T
Page 57 and 58:
Examination of the IH NMR spectra o
Page 59 and 60:
Figure 6: Ring C viewed from the to
Page 62:
Table 9: lH NMR Spectral Data for A
Page 65 and 66:
21 Scheme XIII in which the reactio
Page 67 and 68:
HO HO OH 9 21 &0 " OH 0 60 Scheme X
Page 69 and 70:
fully substituted carbons bearing o
Page 71 and 72:
83= 20 o AI R -= Ac 12 R-=H _-OH Ta
Page 73:
Table 13. IR Spectral Data (CHCI] c
Page 76 and 77:
47 .....OH The IH NMR data for 68 s
Page 79:
The striking difference between the
Page 83 and 84:
Table 18. IH NMR Spectral Data for
Page 85:
The IH NMR spectrum of 23 (Figure 1
Page 88:
The IH NMR spectrum of 24 (Figure 1
Page 92 and 93:
Further evidence for the configurat
Page 97 and 98:
(Cl XXIV H H XXII H H H XXIII H HO
Page 99:
Table 20. lH NMR Spectra Data for I
Page 103 and 104:
spectrometer coupled to a D5-9 comp
Page 105 and 106:
Separation of the Neutral Metabolit
Page 107 and 108:
An impure fraction (1 10 mg) contai
Page 109:
H-9b), 1.97 (1H, brt, 12 Hz, H-1 1a
Page 118:
The unsaturated acetate 34 (5 mg, 0
Page 122 and 123:
cm- I . HREIMS: mlz (formula. inten
Page 124:
FTIR (CHCl l , cast): 3424 (br), 29
Page 128 and 129:
(ether / Skellysolve BI keta-dial 6
Page 130 and 131:
Hz), 1.48 (2H, M), 1.09 (3H, s), 1.
Page 132 and 133:
FTIR: (CHCI!, 0.1 MM) 3560. 1716 (s
Page 134 and 135:
cis-2{3-3a, 10, 10-Tetramethyltricy
Page 137 and 138:
13.5 and 4 Hz, H-6b), 2.34 (1H, td,
Page 139 and 140:
Table 4: Antibiotic Bioassay of Cru
Page 141 and 142:
Table 6: Antifungal Bioassay of Pur
Page 143 and 144:
BIBLIOGRAPHY 1. Hiratsuka. Y.; Tsun
Page 145 and 146:
2720. 25. Turner, W.B,; Aldridge, D
Page 147 and 148:
. Dauben, W.G.; Hart, D.J. J. Org.
Page 149:
69. a. Hashimoto, H.; Ito, T., Mats
Page 153 and 154:
6 5 4 3 2 Figure 3. 400 MHz IH NMR
Page 155:
imp. J'---J.------I • , t t ! 1 4
Page 158:
,---r 1 1 ! , 1 ! l , 3 ( 1 ! 1 ! 2
Page 162 and 163:
Entrée 1 - Préambule 2 - Abstract
Page 165:
INTRODUCTION Dans le cadre de la re
Page 172:
1) un carbonyle appartenant à un s
Page 177:
V Préparation des dérivés 1 - 8-
Page 180 and 181:
13 - OXYDATION DE LA DEHYDROARTHROS
Page 182 and 183:
BIBLIOGRAPHIE 1. R. J. Stipes and R
Page 184:
HC 3 C02 Et 0 C0 2 Et H 3 C H 3 C H
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