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University; Micrdnlms International 300 N INFORMATION TO USERS This reproduction was made from a copy of a document sent to us for microfilming. While the most advanced technology has been used to photograph and reproduce this document, the quality of the reproduction is heavily dependent upon the quality of the material submitted. The following explanation of techniques is provided to help clarify markings or notations which may appear on this reproduction. 1.The sign or “target” for pages apparently lacking from the document photographed is “ Missing Page(s)”. If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent pages. This may have necessitated cutting through an image and duplicating adjacent pages to assure complete continuity. 2. 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These prints are available upon request from the Dissertations Customer Services Department. 5. Some pages in any document may have indistinct print. In all cases the best available copy has been filmed. University; Micrdnlms International 300 N. Zeeb Road Ann Arbor, Ml 46106 8300380 Wilton, John Howard STUDIES OF NATURAL PRODUCTS FROM LIRIODENDRON TULIPIFERA, SIMMONDSIA CAUFORNICA AND HARDWOOD BARK COMPOST. I. NATURALLY-OCCURRING CYTOTOXIC AND ANTIFF.F.DANT SESQUITERPENE LACTONES OF LIRIODENDRON TULIPIFERA. II. ISOLATION, IDENTIFICATION AND ABSOLUTE STRUCTURE ELUCIDATION OF COMPOUNDS FROM SIMMONDSIA CALIFORNICA. III. ISOLATION AND STRUCTURE ELUCIDATION OF ANTIFUNGAL COMPOUNDS PRESENT IN HARDWOOD BARK COMPOST The Ohio Stale University PH.D. 1982 University Microfilms International 300 N. Zeeb Read, Ann Arbor, MI 48106 PLEASE NOTE: In alt cases this material has been filmed in the best possible way from the available copy. Problems encountered with this document have been identified here with a check mark V . 1. Glossy photographs or pages ______ 2. Colored illustrations, paper or print _____ 3. Photographs with dark background _____ 4. Illustrations are poor copy ______ 5. Pages with black marks, not original copy ______ 6. Print shows through as there is text on both sides of page ______ 7. Indistinct, broken or small print on several pages 8. Print exceeds margin requirements ______ 9. Tightly bound copy with print lost in spine ______ 10. Computer printout pages with indistinct print _____ 11. Page(s) ___________ lacking when material received, and not available from school or author. 12. Page(s) ___________ seem to be missing in numbering only as text follows. 13. Two pages numbered ___________ . Text follows. 14. Curling and wrinkled pages ______ 15. Other______________________________________________________________________ University Microfilms International STUDIES OF NATURAL PRODUCTS FROM LIRIODENDRON TULIPIFERA, SIMMONDSIA CALIFORNICA AND HARDWOOD BARK COMPOST. I. NATURALLY-OCCURRING CYTOTOXIC AND ANTIFEEDANT SESQUITERPENE LACTONES OF LIRIODENDRON TULIPIFERA. I I . ISOLATION, IDENTIFICATION AND ABSOLUTE STRUCTURE ELUCIDATION OF COMPOUNDS FROM SIMMONDSIA CALIFORNICA. I I I . ISOLATION AND STRUCTURE ELUCIDATION OF ANTIFUNGAL COMPOUNDS PRESENT IN HARDWOOD BARK COMPOST. DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in the Graduate School of The Ohio State U n iversity By John Howard W ilton, B.A ******* The Ohio State University 1982 Reading Committee: Approved by Dr. Raymond W. Doskotch Dr. Robert W. Brueggemeier Dr. Duane D. M iller C ollege of Pharmacy Dr. Larry W. Robertson This work is dedicated to my w ife, Joanne, for her constant support and understanding throughout. ii ACKNOWLEDGEMENTS The author wishes to extend his sincere appreciation to his adviser, Dr. Raymond W. Doskotch, for his encouragement, excellent guidance and highly contagious enthusiasm. The author also wishes to thank Dr. Jack L. Beal, Dr. Harry A. Hoitink, Dr. Larry W. Robertson, and Dr, Jeffrey W. Williams for their encouragement and support. Special thanks are extended to Mr. John W. Fowble for his endless help and many valuable suggestions. The author acknowledges financial support by the Department of Health, Education and Welfare in the form of the National Research Service Award. The author also wishes to express his appreciation, and best wishes to Mr. Timothy A. Driscoll, whose support, and enthusiasm were endless during the completion of this work. And last, but not least, I thank my loving wife, Joanne, whose constant encouragement, understanding and sacrifices have all helped to make this work a reality. Finally, I thank my parents for their support and the opportunity to obtain a college education. ii i VITA June 21,1952 Born - Buffalo, N.Y., U.S.A. 1974 B.A. (Chemistry - Major) Walsh College Canton, Ohio 1976 Graduate Teaching Associate Division of Pharmacognosy and Natural Products Chemistry College of Pharmacy Ohio State University 1981 Graduate Research Associate National Research Service Award College of Pharmacy Ohio State University PUBLICATIONS "Tulirinol, an Antifeedant Sesquiterpene Lactone for ,’ e Gypsy Moth Larvae from Liriodendron t u lip ife r a ." J. Org. Chem. , 1980, 45, 1441. FIELDS OF STUDY Major Field: Pharmacognosy and Natural Products Chemistry iv TABLE OF CONTENTS PAGE ACKNOWLEDGEMENTS....................................................................................................... i i i VITA....................................................................................................................................... iv LIST OF TABLES............................................................................................................. v ii LIST OF FIGURES.......................................................................................................... xi GENERAL INTRODUCTION............................................................................................. 1 PART I: NATURALLY-OCCURRING CYTOTOXIC AND ANTIFEEDANT SESQUITERPENE LACTONES OF LIRIODENDRON TULIPIFERA................ 2 Chapter 1: T u lirin ol, an Antifeedant Sesqui­ terpene Lactone for the Gypsy Moth Larvae from Lirjodendron tulipifera L ........................................................................ 3 Discussion and Results ....................................................................... U Exper im ental .................................................................................................. 8 Chapter 2: Sesquiterpenes of Lirjodendron tulipifera. Isolation and Characterization of Six Sesqui- terpene Lactones from the Leaves and Root Bark Possessing Cytotoxic and/or Antifeedant Activity 2U Discussion and Results ....................................................................... 30 Ex per im ental .................................................................................................. 51 Chapter 3^ Isolation and Id en tification of Novel Cyclization Products of Lipiferolide, the Major Sesquiterpene of Lirjodendron tu lip ife r a ............................................................................................................... 75 Discussion and Results ........................................................................ 77 Ex per im ental .................................................................................................. 110 v LIST OF REFERENCES.................................................................................................. 155 PART II: ISOLATION, IDENTIFICATION AND ABSOLUTE STRUCTURE ELUCIDATION OF COMPOUNDS FROM SIMMONDSIA CALIFORNICA....................................................................................... 160 Chapter 1: The Isolation and Structural Determination of Three New Cyanoglycosides and Other Constituents from Simmondsia c a lifo r n ic a ................ 161 Discussion and Results ....................................................................... 164 Experimental .................................................................................................. 205 Chapter 2: Determination of the Absolute Stereochemistry of Simmondsin and Related Cyanoglycosides.................................................................................... 269 Discussion and Re su its ....................................................................... 271 Experimental .................................................................................................. 292 LIST OF REFERENCES.................................................................................................. 318 PART III: ISOLATION AND STRUCTURE ELUCIDATION OF ANTIF UNGAL COMPOUNDS PRESENT IN HARDWOOD BARK COMPOST..............................................................................................................................
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