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Hypoxis Hemerocallidea Fisch. and Mey. in Vivo and in Vitro

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Hypoxis Hemerocallidea Fisch. and Mey. in Vivo and in Vitro THE BIOSYNTHESIS AND PRODUCTION OF HYPOXOSIDE IN HYPOXIS HEMEROCALLIDEA FISCH. AND MEY. IN VIVO AND IN VITRO BY ARLENE DIANE BAYLEY Submitted in fulfilment of the requirements for the degree of DOCTOR OF PHILOSOPHY in the Department of Botany, Faculty of Science, University of Natal, Pietermaritzburg. APRIL, 1989 PREFACE The experimental work described in this thesis was carried out in the Department of Botany, University of Natal, Pietermaritzburg from January 1985 to December 1988, under the supervision of Professor J. van Staden. These studies, except where the work of others is acknowledged, are the result of my own investigation. iane Bayley April 1989 i i ACKNOWLEDGMENTS My sincere gratitude is extended to the following people: Professor J. van Staden, my supervisor, for his guidance and encouragement throughout; Professor R.N. Pienaar, Dr. N.A.C. Brown and Professor C.S. Whitehead, all of whom advised me in my Research Committee meetings; Professor S.E. Drewes for his expert advice pertaining to chemistry and hypoxoside, and for his gifts of chemicals during the past 4 years; Dr. P.M. Drennan for her valuable assistance and suggestions with the preparation and interpretation of material in the anatomical studies; Mr. V.J. Bandu and Mrs. B.J. White for their assistance with electron microscopy; Mr. M. Hampton and Mr. D. Boddy for their efficient technical assistance with faulty equipment. Dr. M.T. Smith for his perusal of, and useful comments on the content of my introduction; Mrs. K. Hurly, Miss F.E. Drewes and Miss S. Pridmore for their thorough proof reading; Dr. M. E. Aken, Dr. P. M. Drennan, Mrs P. Donnelly and Mr. V. J. Bandu for their advice and help with the preparation of the anatomical plates; Mr. C.E. Reid of Computer Services for his help with the printing; and the postgraduates and research assi stants of the Botany Department who have helped make the last 4 years enjoyable workwise and socially. I wish to especially thank: My parents for their unfailing support and belief in me throughout my university education; Mr. C.H. Norris for maintaining my sanity, iii being patient .and supportive and for his artistic renditions of many of my figures; and Miss C. Ackermann for her assistance with anatomi ca 1 i nterpretat i on and the production of my plates but most importantly for her friendship , moral support and patience with a bad tempered distracted flatmate. I also gratefully acknowledge financial support from the Council for Scientific and Industrial Research from 1985 to 1986. iv ABSTRACT Hypoxoside, a phenolic diglucoside, with a diarylpentane-type structure, is thought to be the medicinally active constituent of corm extracts of Hypoxis hemeroca77idea Fisch. & Mey. which are reputed to alleviate the symptoms of prostate hypertrophy and urinary infections. The bi osynthes is and production of th is un i que phytochemi cal were investigated in H. Hemeroca77idea using both in vivo and in vitro systems. It was found, in root-producing callus, that l4C-phenylalanine and 14C-t-cinnamic acid were efficient precursors for hypoxoside in comparison to 14C-sodium acetate and 14C-acetyl coenzyme-A, which were not incorporated into the phenolic compound. Thus, at least one aryl moiety of hypoxoside was derived, via phenylalanine and t-cinnamic acid, from the shikimate pathway. The acetate pathway did not appear to be i nvo 1ved in the bi osynthet i c process. The data supports the hypothesis that the molecule is formed from two cinnamate units with the loss of a carbon atom, in oppos it into the proposal that the mol ecul e is deri ved from head-to-ta il condensat i on of acetate units onto a propenylic moiety. Despite the structural similarities between hypoxoside and caffeic and p-coumaric acids, these two hydroxycinnamic acids were not efficient precursors for hypoxoside in vivo or in vitro. A number of reasons are put forward to explain this finding. It was found that the greatest concentration of hypoxoside was located in the corms of intact plants. The major bi osynthet i c site of the molecule was also found to be located in this organ. Since the roots v did accumulate the phytochemical to a small extent, the biosynthetic potential of these organs has not been disregarded. That of the leaves has been, however. The report by PAGE (1984) that the upper region of the corm contained a greater con cent rat i on of hypoxos i de than the lower port ion, is substantiated in this study, where this region was found to be more biosynthetically active than the lower half. Light microscopic and electron microscopic studies revealed that starch storing cells, which accumulated phenolics in their vacuoles, contained seemingly synthetically active tubular endoplasmic reticulum in their cytoplasm. A greater number of these cells were concentrated in the upper region as opposed to the lower half of the corm. It is postulated that these cells are the site for biosynthesis and accumulation of hypoxoside. The shikimate pathway, from which the precursors for hypoxoside are derived, was found, through the exposure of intact plants to 14C-carbon dioxide, to be located mainly in the leaves. It is postulated from the above study and one in which l4C-phenylalanine, 14C-t-cinnamic acid, 14C-p-coumaric acid and 14C-caffeic acid were applied to intact plants, that phenylalanine and/or cinnamic acid are the transported form of the shi kimate deri vat i ves. p-Coumari c and caffeic acids, which are metabolically more stable, are envisaged to be the sequestering forms. The investigation of the seasonal production of hypoxoside revealed that most of the synthesis and accumulation occurred after the corms had broken wi nter dormancy and after the fl ush of 1eaf growth had vi slowed down . During dormancy the production of hypoxoside appeared to cease. The jn vjtro studies, where the effects of light, temperature, nutrients, plant growth regulators and supply of potential precursors, on hypoxoside production by root-producing callus were investigated, indicate that this metabolite is not simply a "shunt" metabolite. A number of factors other than precursor availability enhanced, or reduced the jn vjtro production of this phytochemical. Furthermore, production of the phytochemical and growth were not always antagonistic. Hypoxoside, the biosynthesis of which requires a more thorough investigation, is, however, according to this investigation, a typical secondary metabolite in many respects. vii CONTENTS Page PREFACE ACKNOWLEDGMENTS i i ABSTRACT iv LIST OF FIGURES vii i LIST OF PLATES xvii LIST OF TABLES xviii CHAPTER 1 LITERATURE REVIEW 1 CHAPTER 2 BIOSYNTHETIC INVESTIGATIONS 59 CHAPTER 3 SITE, PRECURSOR MOBILITY AND SEASONAL INVESTIGATION FOR HYPOXOSIDE PRODUCTION 158 CHAPTER 4 IN VITRO STUDIES OF HYPOXOSIDE PRODUCTION 265 CHAPTER 5 CONCLUSION 321 REFERENCES 326 vii i LIST OF FIGURES FIGURE Page 1.1 Morphology of H. hemeroca77idea Fisch. & Mey. 1 1.2 General known world distribution of Hypoxis L. 5 1.3 Sitosterol constituents of H. hemeroca77idea corm extracts. 15 1.4 The molecular structure of hypoxoside and rooperol. 17 1.5 The mol ecul ar structure of some di aryl pentane-type compounds. 25 1.6 The molecular structure of the diarylheptanoids. 26 1.7 The molecular structure of the 9-phenylphenalenones. 26 1.8 The molecular structure of the meta, meta-bridged biphenyls. 27 1.9 Examples of complex hydroxycinnamic acid esters. 29 1.10 The major "highways" of plant metabolism. 34 1.11 An illustration of the points at which secondary metabolism branches from primary metabolism. 35 1.12 General structure of representative members of the different categorises of the flavonoids. 40 1.13 The scheme presented by BU' LOCK and POWELL (1964) for the biogenesis of a class of secondary metabolites. 48 2.1.1 The shikimate pathway. 65 2.1.2 A schematic diagram for phenylpropanoid biosynthesis. 67 2.1.3 The molecular structure of hypoxoside. 68 2.1.4 The structure of the flavonoid quercetin. 68 2.1.5 Molecular structures for the diarylheptanoids and 9- phenylphenalenones. 70 2.1.6 The structure of 6-gingerol. 72 ix FIGURE Page 2.1.7 The structure of lachnanthoside. 73 2.1.8 The mechanism proposed by MARINI-BETTOLO, MESSANA, GALEFFI, MSONTHI and CHAPYA (1985) for the formation of hypoxoside. 75 2.2.1 The three types of callus produced in vitro from corm explants of H. hemeroca77idea. 78 2.2.2 Diagrammatic representation of the slicing of the upper halves of the corm of H. hemeroca77idea prior to sterilisation. 79 2.2.3 Four month old malformed roots produced from corm explants of H. hemeroca77 idea. 82 2.2.4 The bands of UV absorbance detected when an extract of root-producing callus was separated by silica gel thin layer chromatography. 84 2.2.5 The trace of UV absorbance at 257 nm obtained upon the HPLC separation of authentic hypoxoside. 86 2.2.6 The absorbance of the hypoxoside / p-nitroanil ine reagent react i on measured between 400 nm and 700 nm. 88 2.2.7 The calibration curve obtained for the hypoxoside / p-nitroaniline reagent reaction. 89 2.2.8 The UV absorbance at 265 nm obtained upon the HPLC separation of authentic caffeic, p-coumaric, ferulic, sinapic and t-cinnamic acids. 95 x FIGURE Page 2.2.9 The absorbance of the p-coumaric acid / p- nitroaniline reagent, caffeic acid / p-nitroaniline reagent, ferulic acid / p-nitroaniline reagent and sinapic acid / p-nitroaniline reagent reactions measured between 350 nm and 750 nm . 97 . 2.2.10 The calibration curves obtained for the p-coumaric acid / p-nitroaniline reagent, caffeic acid / p­ nitroaniline reagent, ferulic acid / p-nitroaniline reagent and sinapic acid / p-nitroanil ine reagent reactions.
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