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University Microfilms INFORMATION TO USERS This dissertation was produced from a microfilm copy of the original document. White the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the original submitted. The following explanation of techniques is provided to help you understand markings or patterns which may appear on this reproduction. 1. The sign pr "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 thru an image and duplicating adjacent pages to insure you complete continuity. 2. When an image on the film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image. 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University Microfilms 300 North Zeeb Road Ann Arbor, Michigan 43106 A Xerox Education Company 73-11,472 CHEN, (Thin-Nan Rolland, 1941- A PHYTOCHEMICAL INVESTIGATION OF THE BARK OF DORYPHQRA SASSAFRAS ENDLICHER. The Ohio State University, Ph.D., 1972 Health Sciences, pharmacy ; • ;/: University Microfilms, A XEROX Company, Ann Arbor, Michigan THIS DISSERTATION HAS BEEN MICROFILMED EXACTLY AS RECEIVED. A PHYTOCHEMICAL INVESTIGATION OP THE BARK OF DORYPHQRA SASSAFRAS ENDLICHER Dissertation Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Chin-Nan Rolland Chen, B.Sc., M.Sc* ****** The Ohio State University 1972 Approved by / Adviser lege of Pharmacy PLEASE NOTE: Some pages may have indistinct print. Filmed as received. University Microfilms, A Xerox Education Company ACKNOWLEDGMENTS I wish to express my sincere appreciation to ,my, . adviser, Professor Jack L. Beal, for his guidance, support, patience and constant encouragement during the course of investigation and throughout my doctoral pro­ gram. I would like to thank Professor Raymond W. Doskotch for his invaluable advices and determination of n.m.r. spectra and to Professor Lester A. Mitscher for his interest and determination of the circular dichroism spectra. I wish to thank Dr. K. Tomita for providing anonaine hydrochloride and corypalline, Dr. M..- .Shamma for sup­ plying isocorydine hydrochloride and Dr-. E. Brochmann- Hanssen for furnishing reticuline. Special thanks are due to my fellow graduate stu­ dents, who generously provided so many stimulating comments and suggestions. And last, but not least, I am especially grateful to my parents for their unfailing support and encourage­ ment during the years of my education. ii VITA October 18, 19*H............. Born - Tainan, Taiwan I9 6 6........................ B.Sc., Pharmacy, Taipei Medical College, Taipei, Taiwan 1967-I96 8....................Teaching Assistant, College of Pharmacy, University of Houston, Houston, Texas I9 6 8........................ M.Sc., Pharmacognosy, College of Pharmacy, University of Houston, Houston, Texas 1968-197 2....................Research Assistant, College of Pharmacy, The Ohio State University, Columbus, Ohio FIELDS OF STUDY Major Field* Pharmacognosy and Natural Product Chemistry Professor Jack L. 3eal, Adviser iii TABLE OP CONTENTS Page ACKNOWLEDGMENT, ...... 11 VITA AND FIELDS OP STUDY........................ iii LIST OP ILLUSTRATIONS........................... viii Chart ..... vlii Table............ ................. ........ ix Figure...................................... x INTRODUCTION................................... 1 Botanical description...................... 1 The alkaloids of the family Monimiaceae...... 2 The chemical constituents and pharmacological significance of Doryphora sassafras Endlicher 6 The syntheses of the alkaloids of Doryphora sassafras Endlicher .................. 9 STATEMENT OF PROBLEM............. ........... 12 EXPERIMENTAL................................... 13 Materials ......... ............. .......... 13 ‘Methodology............... ................. 13 Chemical analyses......... .......... 13 Valser's reagent.................. 13 Mayer' s reagent...................... 14 Dragendorff's reagent................. 14 Phosphomolybdic acid reagent...... 15 iv Table of contents (continued) Page Iodoplatinic acid reagent.............. 15 Labat's test for methylenedioxy group.. 15 Gibb*s test............. 16 Millon's test......... 16 Evan's test for O-dihydroxyphenol...... 16 Amberlite IRA-*HO anion-exchange resin. 1? Chromatographic analyses........... 17 Physical analyses ........ 18 Melting point determination.......... 18 Infrared spectrophotometric analyses... 18 Ultraviolet spectral analyses.• 18 Nuclear magnetic resonance spectro- metric analyses......... 19 Mass spectrometric analyses.......... 19 Elemental analyses .............. 19 Circular dichroism analyses.......... 19 Optical rotation analyses ........ 20 Preliminary investigation........ 20 Quantitative estimation of total alkaloid content................. 20 Pilot study of the extraction procedure.... 23 General extraction and fractionation of the bark of Doryphora sassafras Endlicher........ 26 Thin layer chromatographic examination of the total alkaloids........ 31 v Table of contents (continued) Page Chromatographic separation and isolation of tertiary alkaloids........................ 3^ The tertiary non-phenolic precipitate fraction (Fraction B)......... 34 The isolation of alkaloid I (Doryanine) 35 The isolation of alkaloid II (Lirio- denine)........................... 38 The isolation of alkaloid III (Iso- corydine)............. 39 The isolation of alkaloid IV (And- naine) ......... 40 The tertiary phenolic precipitate fraction (Fraction D )..... ............ 42 The isolation of alkaloid V (Doryphor- nine)................. **5 Methylation of doryphornine............ 45 Synthesis of doryphornine...............46 The isolation of alkaloid VI (Reti- culine)......... 54 Methylation of reticuline...............$6 The isolation of alkaloid VII (Base A). 56 Fraction £..... 57 The isolation of alkaloid VIII (Dory- flavine)........ 58 Methylation of doryflavine ....... 60 Acetylation of doryflavine ...... 61 Acetylation of doryflavine dimethyl- ether .......................62 vi Table of contents (continued) Page The tertiary non-phenolic alkaloid fraction (Fraction F)............................. 63 The isolation of doryanine, liriodenine isocorydine and anonaine .......... 63 The tertiary phenolic alkaloid fraction (Fraction G ).......... ................... 66 The isolation of alkaloid VI (Reti- culine)................... ........... 66 The isolation of alkaloid IX (Base B).. 66 Attempted methylation of base B....... 69 N-methylation of base B .............. 70 The isolation of alkaloid X (Cory- palline)............................. 71 Chromatographic separation and isolation of the total quaternary alkaloid fraction...... 73 The isolation of alkaloid XI (Choline chloride)............................ 73 Antimicrobial testing of the isolated compounds ................. ......... 77 DISCUSSION..................................... 79 SUMMARY ................................... 101 REFERENCES... ..... 103 APPENDIX......................... ............. 107 vii LIST OP ILLUSTRATIONS Chart Page I Flow sheet for the extraction of the total alkaloids................................... 28 II Flow sheet for the fractionation of the tertiary precipitate alkaloids.............. 30 III Flow sheet for the fractionations of the tertiary and quaternary alkaloids. ...... 32 viii Table Page 1. Results of thin layer chromatographic examination ..............*.......... 33 2. Results of the column chromatography of the tertiary non-phenolic precipitate fraction (Fraction B)... • ......... ..... 36 1 3 . Results of the column chromatography of the phenolic precipitate fraction (Fraction D)............................. 43 k, Results of the column chromatography of fraction E ............... ............... 58 . 5. Results of the column chromatography of the tertiary non-phenolic alkaloid fraction (Fraction F)................... ......... 6k 6 . Results of the column chromatography of the tertiary phenolic alkaloid fraction (Fraction G)..................... ....... 67 7. Results of the column chromatography of the total quaternary alkaloids (Fraction H) 7k 8. Results of the antimicrobial testing....... 78 9 . Comparison of uv, ir and n.m.r. absorption spectra of doryflavine and related com­ pounds ......................... ......... 92 ix Figure Page 1. The synthesis of doryafranine ............. 10
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