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Part I. the Isolation and Characterization of Alkaloids of Caulophyllum Thalictroides (L.) Michx.; Part II. the Isolation and Characterization of Alkaloid and Neutral Principles of Magnolia

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Part I. the Isolation and Characterization of Alkaloids of Caulophyllum Thalictroides (L.) Michx.; Part II. the Isolation and Characterization of Alkaloid and Neutral Principles of Magnolia 71-27,470 FLOM, Michael Stephen, 1940- PART I. THE ISOLATION AND CHARACTERIZATION OF ALKALOIDS OF CAULOPHYLLUM THALICTROIDES (L.) MICHX. PART II. THE ISOLATION AND CHARACTERIZATION OF ALKALOID AND NEUTRAL PRINCIPLES OF MAGNOLIA ACUMINATA L. The Ohio State University, Ph.D., 1971 P harmacology University Microfilms, A XEROX Company , Ann Arbor, Michigan THIS DISSERTATION HAS BEEN MICROFILMED EXACTLY AS RECEIVED PART I. THE ISOLATION AND CHARACTERIZATION OF ALKALOIDS OF CAULOPHYLLUM THALICTROIDES (L.) MICHX. PART II. THE ISOLATION AND CHARACTERIZATION OF ALKALOID AND NEUTRAL PRINCIPLES OF MAGNOLIA ACUMINATA L. DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University by Michael Stephen Flom, B .Sc., M.Sc. sjt * * * * * The Ohio State University Approved by A dviser College of Pharmacy ACKNOWLEDGMENTS I wish to acknowledge my adviser, Professor Raymond W. Doskotch, for his direction, assistance, and patience throughout this study. Also, I gratefully thank my parents whose undying faith has been an inspiration to me in my undergraduate and graduate career. Finally, my greatest appreciation belongs to my wife, Elaine, who has stood as a solid foundation to support me throughout my graduate studies. As to my son, Bradley, and daughter, Jessica, they have eased the burden of my studies and brought untold joy to me. VITA January 9, 1940................................... Born - St. Louis, Missouri 1962 .......................................................... B.Sc. Chemistry; University of California at Los Angeles; Los Angeles, California 1962-196 3 ............................................... Teaching Assistant; College of Phar­ macy, University of Wisconsin; Madison, Wisconsin 1963-196 5 ............................................... Research Assistant; College of Phar­ macy, University of Wisconsin; Madison, Wisconsin 1965 .......................................................... M.Sc. Pharmacy (Pharmaceutical Chemistry); University of Wisconsin; Madison, Wisconsin 1965-1968 .......................................... „. Research Assistant; College of Phar­ macy, The Ohio State University, Columbus, Ohio 1968-1970............................................... Quality Control Director, International Chemical and Nuclear Corp., Irvine California 1970-1971............................................... Graduate Student; College of Pharmacy, The Ohio State University; Columbus, Ohio PUBLICATIONS ’’Isolation and Characterization of Alkaloids from Caulophyllum thalictroides”. Flom, M. S., Doskotch, R. W. and Beal, J. L ., J. Pharm. Sci., 56, 1515 (1967). iii "Steroid Hormone Analogs. IV. C-Nor-D-homoestrone", Kupchan, S. M ., By, A. W. and Flom, M. S., J. Org. Chem., 33, 911 (1968). FIELDS OF STUDY Major Field: Pharmacognosy and Natural Products Chemistry Studies in Organic Chemistry. Professors Melvin Newman, Harold Shechter, Leo Paquette and Robert Ouellette. Studies in Biochemistry. Professors Thomas Diamondstone, Joseph Mendicino, Richard Moore, George Serif and Junius Snell. Studies in Pharmacognosy and Natural Products Chemistry. Professors Jack L. Beal and Raymond W. Doskotch. iv TABLE OF CONTENTS Page ACKNOWLEDGMENTS............................................................................................ ii VITA.............................................. iii LIST OF TABLES....................................................................................................... vii LIST OF FIGURES................................................................................................ viii PART I„ The Isolation and Characterization of Alkaloids of Caulophvllum thalictroides (L.) Michx. Introduction and Historical.......................................................................... 1 A. Botanical Description................................ .................................. 1 B. Prior Investigations of Caulophyllum thalictroides 1 C. Chemotaxonomy of the Lupine Alkaloids................................ 5 D. Objective of Research.................................................................. 5 Experimental...................................................................................................... 6 A. Source of Plant Material. .................................. 6 B. Methodology—Chemical and Physical Analysis ................. 6 C. Purity of Reagents ........................................................... 8 D. Extraction and Initial Separation.............................................. 8 E. Identification of Caulosaponin................................................... 9 F. Isolation of Magnoflorine Chloride............................................ 12 G. Separation and Identification of the Textiary Alkaloids... 13 D iscussion............................ 19 Summary of Findings....................................................................................... 22 Bibliography....................................................................................................... 109 v Page PART II. The Isolation and Characterization of Alkaloid and Neutral Principles of Magnolia acuminata L. Introduction.................................................................................................. 23 A. Botanical, Taxonomic, and Historical Description of Magnolia acuminata L....................................................... 23 B. Alkaloids of the Family Magnoliaceae. ...................... 24 C. Sesquiterpenes of the Family Magnoliaceae................. 34 D. Lignans of the Family Magnoliaceae................................. 35 E. Objective of Research............................................................. 38 Experimental................................................................................................ 39 A. Source of Plant Material....................................................... 39 B. Methodology—Chemical and Physical Analysis ............. 39 C. Extraction of Initial Separation........................................... 39 D. Examination of Tertiary Alkaloid Fraction...................... 42 E. Examination of the Quaternary Alkaloid Fraction 46 F. Examination of the Neutral Fraction of M. acuminata.............................................................................. 53 G. Syntheses of Epoxides and Biphenyls................................. 83 D iscussion....................................................................................................... 95 Summary of Findings................................................................................... 108 Bibliography....................................... I l l vi LIST OF TABLES Table Page 1. Separation of Tertiary Alkaloid Mixture from C. thalictroides......................... 15 2. Separation of Tertiary Alkaloid Mixture from M. acuminata. .......................................................................................... 43 3. Separation of Quaternary Alkaloid from M. acuminata 47 4. Eluting Solvents for Column of Neutral Fraction of M. acuminata............................................................................................ 54 5. Separation of Skellysolve B Fraction from M. acuminata.......................... 55 6 . Separation of Purified Neutral Fraction from M. acuminata............................................................................................ 6 8 vii LIST OF FIGURES Figure Page 1. Flowsheet for Separation of CL thalictroides............................ 10 2. Flowsheet for Separation of M. acuminata.................................. 41 3. Infrared Spectrum of N-Methyllindcarpine Methiodide in KBr................................................................................. 48 4. NMR Spectrum of N-Methyllindcarpine Methiodide in DMSO-dg............................................................................................ 51 5. NMR Spectrum of Calopiptin in CDClg.......................................... 58 6 . NMR Spectrum of Galgravin in CDClg......................................... 62 7. NMR Spectrum of Veraguensin in CDClg..................................... 65 8 . Infrared Spectrum of Aeuminatin in CHClg................................. 71 9. Mass Spectrum of Aeuminatin.......................................................... 73 10. NMR Spectrum of Aeuminatin in CDClg........................................ 75 viii PART I THE ISOLATION AND CHARACTERIZATION OF ALKALOIDS OF CAULOPHYLLUM THALICTROIDES (L„) MICHX. INTRODUCTION AND HISTORICAL A. Botanical Description (1) Caulophyllum thalictroides (L„) Michx. (family, Berberidaceae) is commonly called blue-cohosh or squaw root. According to Lloyd (1), blue- cohosh is derived from the Algonkian word cohosh which literally means rough with hairs and its color from the bluish color of the plant and berries. The latter common name was introduced by Peter Smith who stated that Indian squaws used the rhizomes to facilitate childbirth and for certain uterine disorders. The genus name Caulophyllum is derived from two Greek words meaning stem and leaf while the species was so named by Linnaeus, because of the similarity of the plant leaves to those of the genus Thalictrum. This North American plant, which grows to a height of two feet, is found in rich shady woods from New Brunswick and Southern Ontario to the Southern Alleghenies and between the Eastern coastal plain and the Mississippi Valley. B. Prior Investigations The plant was first examined by Mayer (2) who found it to contain a
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