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A Contribution to the Study of the Alkaloids in the Genus Zanthoxylum (Rutaceae)

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This dissertation has been microfilmed exactly as received 66-15,065 AWAD, Albert Tewfik, 1 9 2 8 - A CONTRIBUTION TO THE STUDY OF THE ALKALOIDS IN THE GENUS ZANTHOXYLUM (RUTACEAE). The Ohio State University, Ph.D., 1966 Health Sciences, pharmacy University Microfilms, Inc., Ann Arbor, Michigan Albert Tewfik Awad 1967 All Rights Reserved A CONTRIBUTION TO THE STUDT OF THE ALKALOIDS IN THE GENUS ZANTHOXILUM (RUTACEAE) DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University Albert Tewfik Awad, B.Se., M.Sc, # s}< # $ % £ The Ohio State University 1966 Approved by Adviser College of Pharmacy ACKNOWLEDGMENTS I would like to express my personal gratitude and my very sincere appreciation to my adviser, Dr. Jack L. Beal, Professor of Pharmacognosy, for his patience and constant encouragement, his under­ standing and generous assistance which rendered this work a success and my association with him friendly, pleasant and rewarding. I am also indebted to Dr. Michael P. Cava, for his helpful suggestions,and to Dr. Sunil Talapatra,particularly for the deter­ mination of the N.M.R. sp ectra. To the members of the reading and examination committee, Drs. Raymond M. Doskotch, Jules B. LaPidus and J. William Burley, I wish to extend my appreciation for their constructive criticism. I gratefully acknowledge the financial support of the U.A.R. Government during my studies. To my colleagues in the College of Pharmacy and to many others — whose names it is not possible to mention in this space — a warm thank you is due. Last, but not least, I cordially express my thanks and admira­ tion to my wife Elvira whose sacrifices, remarkable perseverence and wholehearted cooperation made possible the accomplishment of this dissertation which I would like to dedicate to my children, Joseph, Amal and Samuel. i i VITA November 25, 1928 Born - Cairo, Egypt, U.A.R. June 1952 . B.Sc., Pharmacy, College of Pharmacy, Cairo University, Egypt 1952-195^ . Retail Pharmacist, Drug Stores, Cairo, Egypt 1955 ..................... Analyst "Oil and Soap Factory NAIF-EMAD", Tanta, Egypt 1956-1961 . Teaching and Research Assistant, Pharmacognosy Department, College of Pharmacy, Cairo Uni­ versity, Egypt September 1960. M.Sc., in Pharmacognosy, College of Pharmacy, Cairo University, Egypt 1962-1966 . Ph.D ., Pharmacy, The Ohio S tate U niversity, College of Pharmacy, Columbus, Ohio FIELDS OF STUDY Major Field: Pharmacognosy. Professors Jack L. Beal, Adviser and Raymond M. Doskotch Studies in Biochem istry. P rofessors J.F . Snell; R.O. Moore; J. Gander; G.S. Serif; D.H. Ives and J.F. Mendicino Studies in Plant Physiology. Professor J.W. Burley Studies in Chemistry. Professors H. Schechter; M.S. Newman and Q. VanWinkle Studies in Pharmacology. Professors J.W. Nelson, A. lye, and H. Wolf Honor S o cieties: Rho Chi and Sigma Xi Awards: The Golden Medal of the Egyptian Pharmaceutical Society, in Pharmacognosy in 1952. i i i PUBLICATIONS 1. A. Botanical Study of Cassia obovata Coll Growing in Egypt, Part I: The Leaves and Stem, J, Bot. U.A.R., 5» 61, 1962, 2. Part II: The Fruit, Ibid., 5, 85, 1962. 3* The Identification of the Anthracene Derivatives of the Leaves and Pods of Cassia obovata Coll, Grown in Egypt. Lloydia 25, 238, 1962. The Evaluation of the Leaves and Pods of Cassia obovata Coll Growing In Egypt. Bull. Fac. Pharm. Vol. I, pp. 1 - 6 , 1962. 5. The Anthracene Derivatives of the Leaves and Pods of Cassia acutifolia Delile Cultivated in Egypt. Their Nature and Determination. Ibid., Vol. I, pp. 7—21,. 1 962 . 6. The Isolation and Identification of Three Alkaloids from the Bark of Zanthoxvlum elephantiasis Macf., submitted for publication to J. Pharm. Sci. iv CONTENTS Page ACKNOWLEDGMENTS......................................... i i VITA ................................... ................................................................ i i i TABLES........................................................................................................ ix FIGURES ................................................................................................................ x CHARTS........................................................................................................ x i INTRODUCTION.................................................................................................... 1 STATEMENT OF PROBLEM........................................................................... 7 LITERATURE SURVEV Taxonomy o f the Genus Zanthoxvlum ............................. 3 B otanical D escription o f the Genus Zanthoxvlum .... 9 The Taxonomic Problem of the Genus Zanthoxvlum L. 11 Geographical D istrib u tio n of the Genus Zanthoxvlum L. 13 Description of Z. elephantiasis Macf. (Yellow Sanders). 15 Description of Z. martinicense DC. (Prickly Yellow, Yellow H ercules).................................................... 16 A lkaloids in the Genus Zanthoxvlum L. ................... - 16 1. Furoquinoline Alkaloids............................................... 18 a) The unusual behavior of the furoquinoline alkaloids towards alkyl halides ................... 18 b) Demethylation and rem ethylation ................... 19 c) Hydrogenolysis of the double bond in the fur an rin g ........................................................ 19 2. 6-Canthinone A lkaloids.......................................... 20 3. Quinazolino-carboline Alkaloids.............................. 23 4. Benzylisoquinoline A l k a l o i d s ........................ 27 A. Aporphine alkaloids ................. ..... 28 B. Protopine alkaloids . ................................... 33 C. Protoberberine a lk a lo id s .................................... 34 D. Benzophenanthridine alkaloids ...... 38 5. Simple Amine and Amide A lkaloids ........................... 40 v CON TENTS—Continued Page EXPERIMENTAL............................................................................................... 55 Source of Plant M aterial..................................................... 55 Methodology............................ .......................................................... 55 Part I. Investigation of the Alkaloids of the Bark of Z. elephantiasis Macf. ................................ 56 ” A. Preliminary Investigation..................................... 56 1. Quantitative Estimation of Total Alkaloid Content ........................ 56 2. Investigation of the Probable Number of Alkaloids in Z. elephantiasis Bark ..................... 58 a) Successive solvent extract . ...... 58 b) Horizontal paper chromatography of the extracts ................. ......... 59 c) Fractionation of the alcohol extract into tertiary and quaternary alk alo id s .......................................... ..... 60 d) Further purification and fractiona­ tion of the "tertiary alkaloid fraction" ...................................................... 61 Conclusions .......................................... ........ 62 B. General Extraction and Fractionation of the Alkaloids in the Bark of Z. elephantiasis ................. 62 1. Extraction of Tbtal~Alkaloids ............................. 62 2. Fractionation using 2 Per Cent Aqueous Tartaric Acid ........................................ 63 3. Treatment of the Tartaric Acid Soluble Extractive .................................................................. 63 k, Isolation of Two Alkaloids in the Chloro­ form Extract ..... .............................................. 6k 5. Purification of Base I I ......................................... 65 6. Treatment of the Tartaric Acid Insoluble R e s i d u e ..................................................... 66 7. Preparation of Reineckate of the Quaternary Alkaloids .... ......................... ....... 66 8. Conversion of the Quaternary Alkaloid Reineckates to Chlorides by an Ion- Exchange Resin Method ............ 67 9. Thin-Layer Chromatography of the Crude Quaternary Alkaloidal Chlorides ....... 68 v i CON TEN TS—Continued Page 10. Column Chromatography of Crude Quaternary Chlorides and Isolation of One Quaternary Alkaloid Chloride .............................................................. 69 11. Conversion of the Remainder of the Quaternary Reineckates to Chlorides and Isolation of One Quaternary Alkaloid Chloride by Column Chromatography ......................................... 71 C. The Identification of the Three Crystalline Alkaloids Iso la te d from the Bark of Z. elephantiasis Macf.................................................... 72 1. Identification of Base I (5-methoxy- 6-canthinone) ................... 73 a) Preparation of 5-methoxy-6- canthinone hydrochloride ......... 75 b) Preparation of 5-methoxy-6- canthinone p icrate.................................................. 75 c) Preparation of 5-methoxy-6-can- thinone methiodide....................................... 75 2. Identification of Base II (6-canthinone) . 75 3. Identification of the Quaternary Alka­ loid (Laurifoline Chloride) .......................................... 77 Nuclear Magnetic Resonance Spectra of the Three Alkaloids . ..................................... 80 a) N.M.R. spectra of 5-methoxy-6- c a n th in o n e.................................................................. 80 b) N.M.R. spectra of 6-canthinone ........................ 80 c) N.M.R. spectra of la u rifo lin e chloride . 81 Part II. Investigation of the Alkaloids of the Bark of Z. m artinicense D C . .................................................................................
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    DESMODIUM ALKALOIDS PART IP CHEMICAL AND PHARMACOLOGICAL EVALUATION OF D. GANGETICUM By S. Ghosal and S. K. Bhattacharya Introduction The members of the genus Desmodiurn (Papilionaceae) are mostly shrubs, widely distributed in tropical and sub-tropical habitats and particularly abundant in India. They are well known for their various medicinal uses in the Indian system of medicine (Chopra et al., 1956). Among about four dozen Desmodium species available in this country, chemical and pharmacological evaluation of D. pulchel- lurn Benth. ex Baker (Ghosal et al., 1971) and only preliminary chemical in- vestigation of the entitled species (Ghosal and Banerjee, 1969) have been re- ported so far. The medicinal uses of the plant extracts and the high alkaloid con- tent of the two aforementioned species prompted us to examine in detail the alka- loid content and pharmacological properties of the available Desmodium species. Such investigation would also serve to locate the active principles of the plants with respect to the reported medicinal uses of their crude extracts.The initial chemical investigation with D. gangeticum DC has now been complemented by detail chemical and pharmacological evaluation of the species at different stages of its development. The results are reported in this paper. Experimental The general procedure for the separation and identification of the CHCla-soluble alkaloids involved gradient-pH extraction from aqueous AcOH solution; column chromatographic reso· lution over Brockman neutral alumina; paper chromatography (Whatrna~ 3MM papers) anc TLC (silica gel G, E. Merck) of the eluates from column chromatorgaphic runs in presence 0 markers (Ghosal and Mukherjee, 1966; Ghosal et aI., 1971a); preparation of picrate hydrochloride, and methiodide where possible; and determination of UV, IR, NMR and mas spectra of the single entities.