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Download The A COMPARATIVE PHYTOCHEMICAL STUDY OF CAPRIFOLIACEAE by CHARLES WILLIAM GLENNIE B. Sc. Dalhousie University, 1963 M. S. University of Rhode Island, 1966 A THESIS SUBMITTED IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF Doctor of Philosophy in the Department of - Botany We accept this thesis as conforming to the required standard The University of British Columbia November, 19&9• In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree tha permission for extensive copying of this thesis for scholarly purposes may be granted by the Head of my Department or by his representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Depa rtment The University of British Columbia Vancouver 8, Canada Abstract A comparative phytochemical study of the Caprifolia- ceae.was undertaken. No such study has ever been done. Extracts of fresh leaf material from 5° taxa collected through• out North America were examined for their content of phenolic compounds. Acid and base hydrolysis of the extracts yielded a large array of common phenolic acids and several unknowns. The unknowns occurred in small amounts and were not identified. The cyanogenetic glucoside, sambunigrin, was found to occur only in the genus Sambucus. Chlorogenic acid isomers were identified in the unhydrolyzed extracts of all plants exam• ined. A chromatography system for the separation of these isomers is described. The dicaffeoylquinic acid isomers (isochlorogenic acid) occurred in all genera examined except; Sambucus which contained the monocaffeoylquinic acid isomers. Scopoletin, a 6 Me-7-OPI-coumarin, was present in hydrolyzed extracts of Meigela. This is the only report of scopoletin in the Caprifoliaceae although other coumarins have been found in Diervilla and Symphoricarpos. A crys• talline compound was isolated from extracts of the leaves of Viburnum davidii and was identified as 2 ' , 4-, 4'-trihydroxy- dihydrochalcone. This is the first report of this compound iv being found, in plant material and also it is the first-report of a dihydrochaleone with the 2',V dihydroxy structure rather than the 2',4',6'trihydroxy structure as found in phloretin. The flavonoids identified in this study yielded either the flavonols kaempferol or quercetin or the flavones apigenin or luteolin on hydrolysis. These four compounds displayed a wide variation of glycosylation and distribution throughout the taxa examined.. The flavonols, which are considered to be the more primitive compounds, are found in Viburnum and Sambucus instead of the flavones. This would suggest that these genera are the. most primitive of the family. The relatively more advanced flavones are more prominent in Symphoricarpos and Trlosteum thus suggesting that they are the more advanced genera of the family. The comparatively primitive compound amentoflavone (a biflavonyl) was found in Viburnum carlesii and V. X burkwoodii. The occurrence of sambunigrin in Sambucus only and the absence of the dicaffeoylquinic esters in Sambucus support the idea that Sambucus is sufficiently different to be put into its own family, Sambucaceae (Hoch, 1892), ACKNOWLEDGMENTS Thv. author wishes to express his sincere apprecia• tion to Dr. B. A. Bohm, for his guidance during this study.- The author also wishes to sincerely thank the members of his graduate committee for their advice,and encouragement, Thanks are also due to Dr. Warren Steck, National Research Council, Saskatoon for authentic samples of chloro• genic acid isomers, Dr. L. Horhammer, Munich for a sample of amentoflav;me and to Mr. Marcel Raymond, Montreal Botanical Garden, for allowing the author to collect plant material. The author wishes to express special thanks to Dr. Roy Taylor, University of British Columbia Botanical Garden, for help during the preparation of this manuscript. This investigation was supported by a National Resea.rc Council Grant and carried out in the laboratories of the .Botany'Department, University of British Columbia. The author also wishes to thank Dr. R. D. Gibbs, McGill.University, for consultation and encouragement during this study. TABLE OF CONTENTS PAGE I INTRODUCTION . 1 II LITERATURE REVIEW (A) Early Classification Systems 3 (B) Current Classification of the Caprifoliaceae ............. ^ (C) Cytology of Caprifoliaceae 7 (D) Other Systematic Work on the Caprif oliaceae .......... t . 12 (E) Chemistry of the Caprif oliaceae 15 III MATERIALS AND METHODS (A) Collection of Plant Material ....... 23 (B) Extraction of Plant Material 28 (C) Chromatography of Phenolic Acids ..... 28 (D) Examination of Plant Material for Hydrogen Cyanide Producing Compounds 30 (E) Identification of Sambunigrin ....... 31 (F) Identification of Chlorogenic Acid Isomers ..... 31 (G) [dentification of Scopoletin'in Hydrolysates of Weigela Species ........... 32 (H) The Isolation of 2 ' , k, k'-Trihydroxydihydro- chalcone from Viburnum davidii 34 vi PAGE (I) Identification of the Sugar Residue .... 35 (J) Determination of the Glueose-Aglycone Ratio 36 (K) Base Cleavage of the Aglyeone . 37 (L) "^C Precursor Studies 37 (M) Identification of Flavonoids ....... 38 IV RESULTS (A) . Distribution of Phenolic Acids ...... 4l (B) Plants Containing a Hydrogen Cyanide Producing Compound ........... 50 (C) Identification of Sambunigrin 50 (D) Distribution of Chlorogenic Acid Isomers . 51 (E) Identification of Scopoletin in Hydrolysates or" Weigela Species 6o '(F) The Isolation and Identification of 2',4,4'-. Trihydroxydihydrochalccne from Viburnum davidli 60 (G) Identification of Flavonoids ....... 65 V DISCUSSION (A) Distribution of Phenolic Acids ...... 91 (B) Plants Containing Hydrogen Cyanide Producing Compounds ........... 91 •(C) Distribution of Chlorogenic Acid Isomers . 92 (D) Presence of Scopoletin in Hydrolysates of Welgela Species and Hybrids . 93 (E) Distribution of Flavonoids in the Caprif oliaceae 94 VI REFERENCES 115 LIST OF TABLES PAGE I Cytology of Caprifoliaceae 8 II Fluorescence, Color Reactions and Rf Values of Phenolic Acids . 4-5 III Distribution of Phenolic Acids 4-7 IV Rf Values of Chlorogenic Acid Isomers •. 52 V Distribution of the Isomers of Chlorogenic Acid Found in the Caprif oliaceae 54 VI Ultraviolet Spectral Characteristics of 2' , 4, 4-' -Trihydroxydihydrochale one and Related Compounds .' 62 VII Rf Values of Flavonoids ............ 68 VIII Distribution of the Flavonoids in the Caprifoliaceae ........ ... 84 IX Flavonoids of Sambucus . 97 X Flavonoids of Viburnum 99 Xi Flavonoids of Lonicera 103 LIST OF FIGURES PAGE 1 Chroffiatogram of Phenolic Acidi; 4-3 2 Structures>of Compounds Found in Caprifoliaceae . ....... 67 3 Polygonal Representation of the Paired Affinities Indices of the Genera of the Caprif ol iaceae , , 107 INTRODUCTION The Caprif oliaceae is a family of about 'four hundred, species in 15 genera (Engler, 1964, p. 4-73). The family occurs mainly in the temperate regions of the northern hem• isphere. Members of this family are used extensively as ornamentals. Five genera, totaling 14- species, are naturally occurring over most of British Columbia (Taylor, 1966). The family Caprifoliaceae. is described by shrubs or rarely trees or herbs; leaves opposite normally without stipules; calyx tube with 4 to 5 lobes; corolla tube with 4 to 5 lobes; stamens equal to the number of corolla lobes and inserted on the tube; ovary inferior, 1 to 5. rarely to 8 celled, each cell with 1 to many ovules; fruit a berry, drupe, achene or capsule. One of the major problems in the classification of the Caprifoliaceae has been the position of Sambucus. It was originally placed in the Caprifoliaceae (Fritsch, 1888) but in 1892 H5ch removed Sambucus from the Caprifoliaceae and placed it in a separate family. Since then most workers have left it in the Caprifoliaceae with reservations. The following work was undertaken to see if infor• mation obtained from phytochemical methods would support Hoch's idea and to see how phytochemical evidence would 2 support the classification system of the Caprifoliaceae in general. In the literature there have been many reports of various compounds found in members of the Caprifoliaceae but prior to this work no exhaustive phytochemical examina• tion has been done. In this study 56 taxa in 10 of 15 genera recognized by Engler were examined.. Included in the study were phenolic acids, the various "chlorogenic acids" and flavonoids,, Tests for cyanogenetic compounds were also per• formed . A review of taxonomic research concerned with the Caprifoliaceae is presented. In it the various categories arrived at using non-chemical evidence are described and discussed with particular emphasis upon the position occupied by Sambucus. A brief statement is also made concerning the phytochemical position of the Caprifoliaceae with reference to neighbouring families. LITERATURE REVIEW (A) Early Classification Systems Early taxonomists customarily split the Caprifolia- ceae into two tribes: the Sambuceae and the Lonicereae. Bentham and Hooker (1873) made the separation into two tribes on corolla shape. In Tribe I, Sambuceae, they included Adoxa, Sambucus and Viburnum with their rotate, and/or actinomorph:-.c corollas. In Tribe II, Lonicereae, they included Microsplen- ium, Triosteum, Symphoricarpos, Abelia, Linnaea, Lonlcera, Leycesteria, Diervilla, Pen ta pyx is and Alseuosmia
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