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Buchalter, Leonard, 1922 A PHYTOCHEMICAL INVESTIGATION OF THE ROOTS AND TUBERS OF RUMEX HYMENOSEPALUS FAMILY POLYGONACEAE Item Type text; Dissertation-Reproduction (electronic) Authors Buchalter, Leonard, 1922- Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 29/09/2021 09:03:58 Link to Item http://hdl.handle.net/10150/284768 This dissertation has been microfilmed exactly as received 67-381 BUCHALTER, Leonard, 1922- A PHYTOCHEMICAL INVESTIGATION OF THE ROOTS AND TUBERS OF RUMEX HYMENOSEPALUS FAMILY POLYGONACEAE. University of Arizona, Ph.D., 1966 Chemistry, pharmaceutical University Microfilms, Inc., Ann Arbor, Michigan A PHYTOCHEMICAL INVESTIGATION OF THE ROOTS AND TUBERS OF RUMEX HYMENOSEPALUS FAMILY POLYGONACEAE by Leonard Buchalter A Dissertation Submitted to the Faculty of the COLLEGE OF PHARMACY In Partial Fulfillment of the Requirements For the Degree of DOCTOR OF PHILOSOPHY In The Graduate College THE UNIVERSITY OF ARIZONA 1966 THE UNIVERSITY OF ARIZONA GRADUATE COLLEGE I hereby recommend that this dissertation prepared under my direction by T.pnnar^ Bnp.Vialt.pr entitled A Phyhnr.hprr.i p.al Tnvpsti gflH nn nf thf. Rnohs and Tn-h^-rs nf Piimp-ir HvwiftrinsftT)ali]Br Family Pol vgonaceae, be accepted as fulfilling the dissertation requirement of the degree of nnr.t.rvr of Philosophy ertatioji Director Date After inspection of the dissertation, the following members of the Final Examination Committee concur in its approval and recommend its acceptance:* 7-/3-U / /f *This approval and acceptance is contingent on the candidate's adequate performance and defense of this dissertation at the final oral examination. The inclusion of this sheet bound into the library copy of the dissertation is evidence of satisfactory performance at the final examination. STATEMENT BY AUTHOR This dissertation has been submitted in partial fulfillment of requirements for an advanced degree at The University of Arizona and is deposited in the Uni­ versity Library to be made available to borrowers under rules of the Library,, Brief quotations from this dissertation are allowable without special permission, provided that ac*> curate acknowledgment of source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his judgment the proposed use of the material is in the interests of scholarship. In all other instances, however, permission must be obtained from the author. SIGNED; ACKNOWLEDGMENTS I wish to thank my research director, Dr. Jack Cole, for his advice, guidance and continual encouragement; and the other members of the College of Pharmacy faculty for their encouragement throughout this investigation, I also wish to thank members of the faculty of the Department of Chemistry, as well as my undergraduate instructors in Pharmacy at the Philadelphia College of Pharmacy and Science. I wish to thank the Cancer Chemotherapy National Service Center and the National Cancer Institute, U.S. Public Health Service, Bethesda. Maryland, for financial support in part by contract PH-43-63-1136 and research grant CY-5076-MC, and also the American Cancer Society for support from an Institutional Grant at the University of Arizona,, I am especially thankful to my wife, Barbara, and my mother for their inspiration, assistance, and encourage* ment in this endeavor. iii TABLE OF CONTENTS Page LIST OF ILLUSTRATIONS ................. vii LIST OF TABLES. .................... ix ABSTRACT. x INTRODUCTION 1 TANNIN EXTRACTION 3 GENERAL CHEMICAL CHARACTERIZATION OF TANNIN EXTRACT .. 6 Preliminary Chemical Analysis. .......... 6 Infrared Analysis. .....i ••••••••• 8 Ultraviolet Analysis ••••••••••••• 9 General Chemical Characterization of the Tannin Fraction. • •••••• 9 Paper Chromatographic Analysis 10 General Classification Based on Preliminary Paper Chromatographic Investigation , 14 FRACTIONATION OF TANNIN EXTRACT ............ 16 t General Fractionation Procedure . 16 Paper Chromatographic Analysis of Fractions A and B.......... 16 Infrared Analysis of Fractions A and B...... 18 Classification of Fractions A and B... 21 Conversion of Fractions A and B from Leuco- anthocyanidins to Anthocyanidins. 21 Purification of Anthocyanidins Developed in Fractions A and B Prior to Separation 23 General Chemical Analysis of Fraction B...... 25 Separation of Anthocyanidins by Paper Chromatography. ••••••••••• 25 Preparative Paper Chromatography for Isolation of Anthocyanidins .. , 29 Visible Spectral Analysis of Anthocyanidins. • 30 Infrared Spectrum of Cyanidin from Preparative Paper Chromatography. 32 iv V TABLE OF CONTENTS—Continued Page Degradation by Potassium Fusion of Anthocyanidins • 35 Paper Chromatography Identification of Fragments ........ 36 Summary of Phytochemical Investigation of Fraction B 36 General Chemical Analysis of Fraction A, . , • • . 39 Conversion of Fraction A to Anthocyanidins . 41 Paper Chromatography of Anthocyanidins of Fraction A. .. 41 Structure Proof of Anthocyanidins of Fraction A . 42 Potassium Fusion of Fraction A........ 42 Isolation of Leucocyanidin from Fraction A • • 43 Summary of Chemical Analysis of Fraction A • . 46 Theoretical Implications of Phytochemical Analysis of Fraction A • 47 Condensation by Acid 49 Enzymic Condensation Through a Quinone Polymerization Mechanism ....... 49 Polymers with Ether Linkages • •.«••••• 50 ANTI-TUMOR TESTING. 55 History of Testing ...•• ••••• 55 Examination of Five Different Varieties for Anti-Tumor Activity. • •••••• 56 Preliminary Extracts .••••...••••••. 57 Summary of Anti-Tumor Testing. 57 NON-POLAR EXTRACT ........... 65 Preliminary Evaluation 65 Paper Chromatography of Non-Polar Fraction . 66 Extraction Procedure ••••••••••••••• 66 Paper Chromatography of Chrysophanic Acid, Physcion and Emodin. • ••••«.•» 67 Preliminary Thin-Layer Chromatography. ...••• 70 Preparative Thin-Layer Chromatography 72 Isolation of Chrysophanic Acid and Physcion. ... 76 Identification of Chrysophanic Acid. • . • 77 Identification of Physcion . 81 Acetate Derivative. 82 vi TABLE OF CONTENTS--Continued Page Isolation and Identification of Emodin ...... 84 Summary of Materials Identified in7 Non-Polar Extract ............ 89 SUMMARY AND CONCLUSIONS » . , . 91 REFERENCES. 95 f LIST OF ILLUSTRATIONS Figure Page 1. Extraction Procedure for Tannin Fraction • • • • • 5 2. Infrared Spectrum of Tannin Extract. II 3. Ultraviolet Spectrum of Tannin Fraction 12 4. Paper Chromatography of Tannin Extract 15 5. Solvent Fractionation of Tannin Fraction • • • . • 17 6. Infrared Spectrum of Fraction A. ••••••••• 19 7. Infrared Spectrum of Fraction B. ••••••••• 20 8. Conversion of Fractions A and B to Anthocyanidins . 22 9. Anthocyanidin Purification Procedure 26 10. Infrared Spectrum of Cyanidin Chloride, Commercial Sample, 33 11. Infrared Spectrum of Cyanidin Chloride, Synthesized from Fraction B..,..«•••••. 34 12. Degradation of Anthocyanidins by Potassium Fusion, 37 13. Basic Structures of Leucoanthocyanidins and Anthocyanidins from Fraction B . ....... 40 14. Infrared Spectrum of Monomeric Leucocyanidin ... 45 15. Structures Illustrating Types of Condensations . 53 16. Extraction Procedure for the Non-Polar Extract . 68 17. Thin-Layer Chromatography of Non-Polar Extract , , 73 18. Infrared Spectrum of Chrysophanic Acid from Non-Polar Extract . 79 vii viii / LIST OF ILLUSTRATIONS (Continued) Figure Page 19. Infrared Spectrum of Chrysophanic Acid, v Commercial Sample 80 20. Infrared Spectrum of Physcion from Non-Polar Extract ....... 83 21. Infrared Spectrum of Qnodin from Non-Polar Extract 87 22. Infrared Spectrum of Emodin, Commercial Sample. .. ...... 88 23. Anthraquinone Pigments of Non-Polar Extract 90 LIST OF TABLES Table Page 1. Qualitative Tests for Anthocyanidins. 24 2. Rf Values of Anthocyanidins Developed from Fraction B . ....... 28 3. Visible Spectral Analysis of Anthocyanidins from Fraction B, • 31 4. Rf Values of Commercial Samples and Fusion Fragments* 38 5. Anti-Tumor Test Results ••••..•••••••• 60 6. Paper Chromatography of Non-Polar Extract . 71 7. Thin-Layer Chromatography of Non-Polafc Extract 74 8. Rf Values Thin-Layer Chromatography on Silica Gel Layers of Material (A; and Commercial Sample of Chrysophanic Acid. • ••••• 78 9. Rf Values Thin-Layer Chromatography on Silica Gel Layers of Natural Product from Spot No. 1 and Commercial Sample of Emodin 85 ix ABSTRACT The roots and tubers of Rumex Hvmenosepalus yielded a tannin fraction which demonstrated anti-tumor activity. A phytochemical analysis was undertaken to attempt to iden­ tify the material responsible for the anti-tumor activity,, The tannin fraction was identified as one containing poly- phenolic flavanoidal units. The tannin fraction was separated into a polymeric condensed fraction, and a fraction consisting of monomeric units, by means of solvent fractionation with water and ethyl acetate* The polymeric condensed fraction of the tannin extract was chemically identified as consisting of polymeric leucoanthocyanidin (flavan-3:4-diol) units. The individual leucoanthocyanidins present in the condensed portion consisted of leucocyanidin (5:7:3':4*-tetrahydroxyflavan-3:4-diol)9 leucodelphinidin (5:7:3*:4*:5*-pentahydroxyflavan-3:4-diol),
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