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PELEWSKI, Norbert Anthony, 1938- a PHYTOCHEMICAL INVESTIGATION of the BARK of CODONOCARPUS AUSTRALIS A

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PELEWSKI, Norbert Anthony, 1938- a PHYTOCHEMICAL INVESTIGATION of the BARK of CODONOCARPUS AUSTRALIS A This dissertation has been microfilmed exactly as received PELEWSKI, Norbert Anthony, 1938- A PHYTOCHEMICAL INVESTIGATION OF THE BARK OF CODONOCARPUS AUSTRALIS A. CUNNINGHAM. The Ohio State University, Ph.D., 1967 Chemistry, biological University Microfilms, Inc., Ann Arbor, Michigan A PHYTOCHEMICAL INVESTIGATION OP' THE BARK OP CODONOCARFPS AUSTRALIS A. CUNNINGHAM DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of the Ohio State University By Norbert Anthony Pilewski ****** The Ohio State University 1967 Approved by Adviser ollege of Pharmacy ACKNOWLEDGMENTS The author wishes to express his appreciation to his adviser, Dr. Jack L. Beal, for his guidance and support during the course of this investigation and throughout his doctoral program. He also wishes to thank Dr. Raymond VJ. Doskotch of the College of Pharmacy for his helpful advice. The author is especially grateful to Dr. Jozef Tomko, Post Doctoral Fellow at The Ohio State University, College of Pharmacy, and Research Chemist, Chemicky Ustav S.A.V., Bratislava, Czechoslovakia, for his encouragement and pract­ ical advice during this investigation. He is further indebted to Dr. Clara G. Weishaupt, Associate Professor and Curator of the Herbarium at the Department of Botany and Plant Pathology for her technical assistance in the editing of certain portions of the taxo­ nomic section of the thesis. ii VITA December 15, 193& Born; Oil City, Pennsylvania 1961.... B.S., University of Pittsburgh, Pittsburgh, Pennsylvania 1961-1963*••••••• Teaching Assistant, Department of Pharmacognosy, College of Pharmacy, University of Pittsburgh, Pittsburgh, Pennsylvania 1963... M.S., University of Pittsburgh, Pittsburgh, Pennsylvania 1963-1967........ Research Assistant, College of Pharmacy, The Ohio State University, Columbus, Ohio PUBLICATIONS "Studies on False-Positive Alkaloid Reactions With Dragen- dorff's Reagent", Lloydia 312-319 (1962) FIELDS OF STUDY Major Field: Pharmacognosy Professor Jack L. Beal, Adviser iii CONTENTS Page ACKNOWLEDGMENT i i VITA, PUBLICATIONS, AND FIELDS OF STUDY........ iii TABLES.............................................. ix FIGURES............................................ x I. INTRODUCTION AND STATEMENT OF' PROBLEM 1 II. LITERATURE SURVEY........................... 2 A. Botanical Characteristics and Relationships........................... 2 B. The Chemical Constituents of Codonocar­ pus australis A. Cunn. and Plants of Related Genera...... .................. 8 1. Codonocarpus australis A. Cunn.... 8 2. Codonocarpus cotinifolius F. Muell 9 3* Gallesia gorazema Moq ..... 10 *f. Gyrostemon ramulosus Desf. 10 5. Phytolacca arcericana L . , (Phvto- 10 lacca decandra L.).T.............. 6. Phytolacca australis....... 12 7. Phytolacca octandra L ..... 12 8. Rivina aurantiaca.......... 12 9. Rivina humilis L., (Rivina laevis L .) .............................. 12 10. Trichostigma peruvianum... 13 C. Toxicity and Pharmacological Significance of Codonocarpus australis A. Cunn. and Plants of Related Genera................ iM- iv CONTENTS (Cont'd) Page 1. Codonocarpus australis A. Cunn., "Bell Fruit", "Native Poplar"........ l^f 2. Codonocarpus cotlnifolius F. Muell., "Bell Fruit"........................... lb 3. Phytolacca acinosa.................... 1*+ Phytolacca americana L., (Phytolacca decandra L.), "Pokeweed", "Ink Weed", "Pigeon Berry"...................... l*f 5. Phytolacca diolca L., "Bella Somhra Tree".................................. 17 6 . Phytolacca esculenta.................. 17 7. Phytolacca octandra L., "Ink Weed"... 17 8 . Rivina humilis L ., (Rivina laevis L .). "Coral Berry"........................ 17 III. EXPERIMENTAL.................................... 18 A* Materials.................................. 18 B. Reagents and Tests......................... 19 1. Dragendorff reagent........... 19 2. Labat test for rethylenedioxy group.. 19 3 . Mayer's reagent.................... 20 b, Phosphomolybdic acid reagent.......... 20 5. Valser's reagent....................... 20 6. Amberlite IRA-^IO anion-exchange resin 21 7. Nylon 66 powder...................... 21 8. Acid silicic acid: celite-^^ (*+:!)•• 21 v CONTENTS (Cont’d) Methodology........ ...................... 1. Ultraviolet spectral analyses..... 2. Melting point determinations....... 3* Optical rotation measurements...... *+. Infrared spectrophotometric analyses............................. 5* -.K. determinations......... ....... P 9 . 6. Nuclear magnetic resonance spectrophotometric analyses........ 7- Mass spectrometric analysis........ 8. Microanalyses....................... Preliminary Investigation............ 1. Quantitative estimation of total alkaloid content............. ...... Extraction and Fractionation of C. australis A. Cunn.................... 1. Fraction E ........................... 2. Fraction C .......................... 3. Fraction A ............. ............. Chromatographic Separation of the Total Tertiary Alkaloids in Fraction C ....... Isolation of Tertiary Alkaloids from Fraction C ....................... *...... 1. Alkaloid I ........................... a. Melting point................... b. Ultraviolet spectral data...... CONTENTS (Cont'd) Page 2. Alkaloid II .......................... *+2 a. Melting point................... b2 b. Ultraviolet spectral data *+2 3. Alkaloid IV .......................... *+2 a. Melting point...... .......... .. Mf b. Optical rotation................ ^ c. Ultraviolet spectral data Mf d. K determination ....... ^ P a i. Molecular weight..... *+*+ e. Nuclear magnetic resonance data............................. bb f. Labat test for methylenedioxy group........................... h 5 g. Microanalysis................... bj H. Purification of Fraction A • • b7 I. Chromatographic Separation of the Quaternary Alkaloids in Fraction NP-I-212a................................ 51 J. Isolation of Quaternary Alkaloids from Fraction NP-I-212a...................... 57 1. Alkaloid VII......................... 57 a. Melting point................... 57 b. Optical rotation............. 57 c. Ultraviolet spectral data 57 d. Molecular weight from mass spectral data. ...... • 59 vii CONTENTS (Cont'd) Page e. Nuclear magnetic resonance data............................. 5 9 f. Kicroanalysis................... 59 2. Alkaloid IX .......................... 59 a. Melting point.................. 59 b. Optical rotation............... 61 c. Ultraviolet spectral data 61 3. Alkaloid X ........................... 61 a. Melting point................... 61 b. Ultraviolet spectral data...... 61 !+, Alkaloid XI .......................... 63 a. Melting point................... 63 b. Ultraviolet spectral data 63 5. Alkaloid XII......................... 63 a. Melting point................... 65 b. Ultraviolet spectral data 65 IV. SUMMARY....................................... 69 *'• -i LIST OF REFERENCES. ............................ 71 viii TABLES Table Page 1. Results of the Chromatographic Separation of Fraction C (Total Tertiary Alkaloids) on a Neutral Alumina Grade IV Column.......... 37 2. Results of the Chromatographic Separation of NP-I-212a (Quaternary Alkaloid Mixture) on an Acid Silicic Acid: Celite-^? (*+:l) Column...................... ............. 51* 3. Absorption Maxima of the Ultraviolet Spec­ tra of the Alkaloids of C, australis 67 ix FIGURES Figure Page 1. Leaves and Fruit of Codonocarpus australis A. Cunn. (Phytolaccaceae) ............ 6 2. Codonocarpus australis A. Cunn., » <cojtiPLif^Dllus, F. v. M . ....... ••.<*.....*« 7 3. Flow Sheet for the Extraction of the Total Alkaloids........................... 3*+ b, Elution Pattern for Neutral Alumina Grade IV Column......................................... 39 5. The Purification and Separation of the Total Quaternary Alkaloids in Fraction A......... 50 6. Elution Pattern for Acid Silicic Acid: Celite-5^5 (*+:l) Column.................... 53 7. Infrared Spectrum of Alkaloid I ............. ^1 8. Infrared Spectrum of Alkaloid II............. ^3 9. Infrared Spectrum of Alkaloid IV........... *+6 10. Infrared Spectrum of Alkaloid VII............ 58 11. Infrared Spectrum of Alkaloid IX ........ 60 12. Infrared Spectrum of Alkaloid X .............. 62 13. Infrared Spectrum of Alkaloid XI. ............ 6*f lb. Infrared Spectrum of Alkaloid XII ............ 66 x INTRODUCTION AND STATEMENT OF PROBLEM In the search for new medicinal agents from plants, those reported to have medicinal uses in folklore, to he poisonous, or to contain alkaloids are the most promising plants to investigate. Plants containing alkaloids are im­ portant because alkaloids constitute the largest class of medicinal agents from higher plants. In a world-wide search for new medicinal plants conducted by the Eli Lilly & Company of Indianapolis, Indiana, the bark of an Australian tree, Codonocarpus australis A. Cunn. gave a positive test for alkaloids. It, along with several other plants, was considered worthy of further investigation and representative samples of each were sent to Dr. Jack L. Beal, this author's adviser. Of the plants tested, C. australis A. Cunn. gave the strongest alkaloid .e~t. A literature search revealed that this plant had never been chemically investigated and is in the Phytolaccaceae. Until now, this was known as a plant family from which an alkaloid had never been isolated, with the exception of caffeine (39). Since this particular plant did give a test for alkaloids, hence could be assumed to have some pharmacological activity, and had
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