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Sodium Catechin-(4 ->8)-Epicatechin-(413)-Sulfonate Were

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Sodium Catechin-(4 ->8)-Epicatechin-(413)-Sulfonate Were AN ABSTRACT OF THE THESIS OF YOUNGS00 BAE for the degree of DOCTOR OF PHILOSOPHY in Forest Products presented on January 27, 1989 Title : DOUGLAS-FIR INNER BARK PROCYANIDINS : SULFONATION, ISOLATION AND CHARACTERIZATION /7 Signature redacted for privacy. Abstract approved : Ae",/ Dr. 6sei J. archesy The polymeric procyanidins(condensedtannins)of Douglas-fir inner bark were isolated and their reaction with sodium hydrogen sulfite was studied. Gel permeation chromatography analyses indicated that depolymerization to lower molecular weight flavan-4- and procyanidin-4- sulfonates does not go to completion. A significant amount of higher molecular weight procyanidin sulfonate derivatives remains. Sodium epicatechin-(43)-sulfonate, sodium epicatechin-(413->8)-epicatechin-(413)-sulfonate, sodium 1- (3,4-dihydroxypheny1)-2-hydroxy-3-(2,4,6-trihydroxypheny1)- propane-l-sulfonate, disodium epicatechin-(413,5')- disulfonate, sodium 2,3L-cis-3,4-trans-8,9-cis-9,10-cis-2,10- (3,4-dihydroxydipheny1)-8-(2,4,6-trihydroxypheny1)-3,4,9,10- tetrahydro-2H,8H-pyrano[2,3-h] chromene-(413)-sulfonate and sodium catechin-(4->8)-epicatechin-(413)-sulfonate were isolated from the sulfonation reaction mixture. The last three compounds are new and novel and provide insight into competing reactions. Isolations were accomplished by competing reactions. Isolations were accomplished by repeated chromatography over Sephadex LH-20 with ethanol and various aqueous alcoholic solvent systems. Structural elucidation was carried out using nuclear magnetic resonance spectroscopy, infra red spectroscopy, fast atom bombardment mass spectroscopy and in one case a micro-degradation reaction with phloroglucinol. In the course of this research it was demonstrated that polystyrene standards are not accurate for the gel permeation chromatography analysis of procyanidin acetates. It was also demonstrated that gel permeation chromatography analysis of underivatized polymeric procyanidins can be carried using a N,N-dimethyl- formamide solvent system with polystyrene divinylbenzene co-polymer columns. Douglas-Fir Inner Bark Procyanidins : Sulfonation, Isolation and Characterization by Youngsoo Bae A THESIS submitted to Oregon State University in partial fulfillment of the requirements for the degree of Doctor of Philosophy Completed January 27, 1989 Commencement June 1989 APPROVED : Signature redacted for privacy. Assistant rof sor oFo est Product Chemistry in cha ge of major Signature redacted for privacy. Head of the Departme of Forest Products Signature redacted for privacy. Dean of Grac1te School(' Date thesis is presentedJanuary 27, 1989 Typed by Youngsoo Bae for Youngsoo Bae ACKNOWLEDGEMENTS I wish to thank my major professor, Dr. Joseph J. Karchesy, for his interest, counsel, and encouragement throughout this research. I also wish to acknowledge Dr. Robert L. Krahmer, Dr. Murray L. Laver and Dr. L. Y. Foo for their assistance and counsel during this work. Acknowledgement is also made to Dr. Dwight D. Weller for his helpful discussions and encouragement. I would like also to thank Dr. Douglas F. Barofsky for his helpful discussions on the Fast Atom Bombardment Mass Spectroscopy data and particularly for the use of his laboratory equipment and special chemicals. I also wish to acknowledge Rodger L. Kohnert, Department of Chemistry, Oregon State University, for his assistance in obtaining the 400 MHz Nuclear Magnetic Resonance Spectroscopy data. Acknowledgement is also made to Brian C. Arbogast, Department of Agricultural Chemistry, Oregon State University, for his assistance in obtaining the Fast Atom Bombardment Mass Spectroscopy data. Lastly, I would like to express my appreciation to my parents and my family for their sincere support, patience, and understanding throughout the past five years. This research was supported by the Department of Forest Products, Oregon State University. TABLE OF CONTENTS INTRODUCTION 1 HISTORICAL REVIEW 8 Sulfonation 8 Gel permeation chromatography 13 EXPERIMENTAL 16 General 16 Collection of inner bark 18 Bark extraction 18 Purification of polymeric procyanidins 19 Sulfonation reaction 20 Isolation and purification of procyanidin 23 sulfonate derivatives Characterization of procyanidin sulfonate 24 derivatives 7.1. Sodium epicatechin-(413)-sulfonate 24 7.2. Sodium epicatechin-(48->8)-epicatechin- 26 (413)-sulfonate 7.3. Sodium 1-(3,4-dihydroxypheny1)-2-hydroxy- 27 3-(2,4,6-trihydroxypheny1)-propane-1-sulfonate 7.4. Disodium epicatechin-(413,5')- disulfonate 28 7.5. Sodium 2,3-cis-3,4-trans-8,9-cis-9,10-cis- 30 2,10-(3,4-dihydroxydipheny1)-8-(2,4,6-tri- hydroxypheny1)-3,4,9,10-tetrahydro-2H,8H- propane[2,3-h]chromene-413-sulfonate 7.6. Sodium catechin-(4-->8)-epicatechin-(4B)- 31 sulfonate 7.7. Sodium 1-(3,4-dihydroxypheny1)-2-hydroxy- 33 3-(2,4,6-trihydroxypheny1)-propane-1-sulfonate from (+)-catechin and (-)-epicatechin Gel permeation chromatography(GPC) 35 8.1. GPC analysis of acetylated procyanidin 35 polymers 8.1.1. Acetylation of procyanidin polymer 35 8.1.2. Calibration of GPC system 36 8.1.3. GPC analysis of acetylated procyanidin 37 polymers 8.2. GPC analysis of procyanidin polymers 37 8.2.1. Calibration of GPC system 37 8.2.2. GPC analysis of procyanidin polymers 38 RESULTS AND DISCUSSION 43 Collection and extraction of bark 43 Purification of polymeric procyanidins 45 Sulfonation of polymeric procyanidins 48 Isolation and characterization of procyanidin 50 sulfonates 4.1. Sodium epicatechin-(48)-sulfonate 52 4.2. Sodium epicatechin-(48->8)-epicatechin-(4B)- 57 sulfonate 4.3. Sodium 1-(3,4-dihydroxypheny1)-2-hydroxy- 63 3-(2,4,6-trihydroxypheny1)-propane-1-sulfonate 4.4. Disodium epicatechin-(4B,5')-disulfonate 68 4.5. Sodium 2,3-cis-3,4-trans-8,9-cis-9,10-cis- 79 2,10-(3,4-dihydroxydipheny1)-8-(2,4,6-tri- hydroxypheny1)-3,4,9,10-tetrahydro-2H,8H- pyrano[2,3-h]chromene-(4B)-sulfonate 4.6. Sodium catechin-(4 ->8)-epicatechin-(4B)- 91 sulfonate 4.7. Sodium 1-(3,4-dihydroxypheny1)-2-hydroxy-3- 99 (2,4,6-trihydroxypheny1)-propane-1-sulfonate from (+)-catechin and (-)-epicatechin Gel permeation chromatography(GPC) 105 5.1. GPC analysis of acetylated procyanidin 106 polymers 5.2. GPC analysis of underivatized procyanidin 107 polymers SUMMARY AND CONCLUSIONS 114 LITERATURE CITED 118 LIST OF FIGURES Figure Sample purification scheme. 21 GPC chromatograms on procyanidin sulfonates. 22 Purification scheme of procyanidin sulfonates. 25 Calibration curve of GPC system for procyanidin 40 peracetate analysis. Calibration curve of GPC system for polymeric 42 procyanidin analysis. 13C NMR spectrum of purified polymeric 47 procyanidins. The flow diagram for the isolation of procyanidin 53 sulfonate derivatives. One dimensional TLC of the isolated procyanidin 54 sulfonate derivatives. FAB-MS spectrum of compound (6). 57 1H NMR spectrum of compound (6). 58 13C NMR spectrum of compound (6). 59 FAB-MS spectrum of compound (7). 63 IH NMR spectrum of compound (7). 64 13C NMR spectrum of compound (7). 65 FAB-MS spectrum of compound (5). 69 1H NMR spectrum of compound (5). 70 13C NMR spectrum of compound (5). 71 FAB-MS spectrum of compound (8). 75 1H NMR spectrum of compound (8). 76 13C NMR spectrum of compound (8). 77 The proposed reaction mechanism for the formation 78 of compound (8). FAB-MS spectrum of compound (9). 84 Expanded view of the molecular ion region in 85 FAB-MS spectrum of compound (9). 1H NMR spectrum of compound (9). 86 13C NMR spectrum of compound (9). 87 COSY spectrum of compound (9). 88 HETCOR spectrum of compound (9). 89 The proposed reaction mechanism for the formation 90 of compound (9). FAB-MS spectrum of compound (10). 95 Expanded view of the molecular ion region in 96 FAB-MS spectrum of compound (10). 111NMR spectrum of compound (10). 97 13C NMR spectrum of compound (10). 98 Two dimensional TLC for the partially cleaved 102 products of compound (10). 13C NMR spectrum of compound (5) from 103 (-)-epicatechin sulfonate derivative. 13C NMR spectrum of compound (5) from 104 (+)-catechin sulfonate derivative. GPC chromatogram of procyanidin peracetates. 109 Distribution curve representing the molecular 110 weight profile of procyanidin peracetates. Comparison of the calibration curve between 111 polystyrene and procyanidin oligomer peracetate standards. GPC chromatogram of procyanidin polymers. 112 Distribution curve representing the molecular 113 weight profile of procyanidin polymers. LIST OF SCHEMES Scheme Etherocyclic ring opening reaction of flavan- 11 (3,4)-diol with sulfite ion. Etherocyclic ring opening reaction of (+)-catechin 11 with sodium bisulfite. Sulfonation of southern pine procyanidins with 12 sodium hydrogen sulfite. LIST OF TABLES Table Variation in hydroxylation patterns of principal 5 classes of condensed tannins. Calibration report for procyanidin peracetates. 39 Regression analysis for procyanidin peracetates. 39 Calibration report for procyanidin polymers. 41 Regression analysis for procyanidin polymers. 41 DOUGLAS-FIR INNER BARK PROCYANIDINS : SULFONATION, ISOLATION AND CHARACTERIZATION INTRODUCTION Douglas-fir[Pseudotsuga menziesii(Mirb.) Franco] is the major commercial timber species of the Pacific Northwest, accounting for about three quarters of softwood inventory. Its wood is very strong for its weight and thus highly valued for the production of lumber and construction plywood which are two major and important forest products industries in the state of Oregon. In the process of harvesting and preparation of Douglas-fir logs for these industries a substantial amount of bark is also made available.
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