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Secondary Plant Metabolites As Defense Against Herbivores and Oxidative Stress

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Secondary Plant Metabolites As Defense Against Herbivores and Oxidative Stress Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology 567 _____________________________ _____________________________ Secondary Plant Metabolites as Defense against Herbivores and Oxidative Stress Synthesis, Isolation and Biological Evaluation BY KATHARINA BRATT ACTA UNIVERSITATIS UPSALIENSIS UPPSALA 2000 Dissertation for the Degree of Doctor of Philosophy in Organic Chemistry presented at Uppsala University in 2000 ABSTRACT Bratt, K. 2000. Secondary Plant Metabolites as Defense against Herbivores and Oxidative Stress. Synthesis, Isolation and Biological Evaluation. Acta Univ. Ups, Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology 567. 53 pp. Uppsala. ISBN 91-554-4807-0. In this thesis the isolation, synthesis and biological evaluation of natural defense compounds against herbivores or oxidative stress is discussed. The first part concerns the metabolites of platyphylloside ((5S)-5-hydroxy-1,7-bis-(4- hydroxyphenyl)-3-heptanone-5-O-β-D-glucopyranoside), a phenolic glucoside found in birch (Betula pendula) that possess digestibility inhibiting activity in herbivores. The structure-activity relationship of platyphylloside analogues were investigated regarding to stereochemistry and substitution pattern on the aromatic rings. The metabolites formed in vitro in rumen fluid were synthesized and the active metabolite determined as (R)-centrolobol (1,7-bis-(4-hydroxyphenyl)-3-heptanol). Treatment of mice and rats with rac-centrolobol did not effect either food intake or body weight. Effect of platyphylloside in moose was also investigated, and the results indicate that there was an in vivo digestibility reducing activity. The second part concerns naturally occurring antioxidants. Avenanthramides is a class of phenolic antioxidants found in oat (Avena sativa). Avenanthramides derived from either anthranilic acid or 5-hydroxyanthranilic acid were evaluated for their antioxidative capacity and quantified in oat extracts. Avenanthramides derived from 5- hydroxyanthranilic acid possessed higher activity than those from anthranilic acid. The order of reactivity depending on substitution pattern on the phenolic moiety was found to be 4-hydroxy < 4-hydroxy-3-methoxy < 3,5-dimethoxy-4-hydroxy and 3,4- dihydroxy. A synthesis towards antioxidative compounds such as 4-deoxycarbazomycin was developed. The third part concerns the isolation of compounds from Lodgepole pine (Pinus contorta) with antifeedant activity against pine weevil (Hylobius abietis). Two compounds possessing high activity were isolated and identified. Katharina Bratt, Department of Organic Chemistry, Institute of Chemistry, University of Uppsala, Box 531, SE-751 21 Uppsala, Sweden ã Katharina Bratt 2000 ISSN 1104-232X ISBN 91-554-4807-0 PAPERS INCLUDED IN THE THESIS This thesis is based on the following papers and appendix, referred to in the text as Roman numerals I-VII. I Synthesis and Digestibility Inhibition of Diarylheptanoids: Structure-Activity Relationship. Bratt, K.; Sunnerheim, K. J. Chem. Ecol. 1999, 25, 2703. II Synthesis of the Metabolites from Platyphylloside and Evaluation of Their Digestibility Inhibiting Activity. Bratt, K.; Sunnerheim, K. Submitted. III Digestion Inhibiting Effects of Weeping Birch (Betula pendula) in a Moose (Alces alces L). A Pilot Study. Sunnerheim, K.; Rehbinder, C.; Bratt, K.; Cedersmyg, O. Ragnifer, 2000, Accepted. IV Avenanthramides in oats: Structure – Antioxidative activity relationship. Bratt, K.; Sunnerheim K.; Bryngelsson, S.; Häll Dimberg, L. Manuscript. V Towards Synthesis of Carbazole Alkaloids with Oxygen in 3-position. Bratt, K.; Bäckvall, J.-E.; Sunnerheim, K. Preliminary Manuscript VI Pine Weevil (Hylobius abietis) Antifeedants from Lodgepole Pine (Pinus contorta). Bratt, K.; Sunnerheim, K.; Nordenheim, H.; Nordlander, G.; Långström, B. Submitted. VII Appendix: Supplementary material. Reprints were made with kind permission from the publishers. CONTRIBUTION REPORT The author wishes to clarify her own contributions to research results presented in the present thesis. Paper I. All synthetic work; significantly contributed to the interpretation of the results and writing the manuscript. Paper II. All synthetic work; significantly contributed to the interpretation of the results and writing the manuscript. Paper III. Synthesized the reference compounds for identification in the feces samples. Paper IV. All synthesis and characterizing of avenanthramides; carried out the experimental work in collaboration with the other authors; equally contributed to the interpretation of the results and writing the manuscript. Paper V. All synthetic work; significantly contributed to the interpretation of the results and writing the manuscript. Paper VI. All isolation, characterization and synthesis of active compounds; equally contributed to the interpretation of the results and writing the manuscript. LIST OF ABBREVIATIONS BHA 2-tert-butyl-4-methoxyphenol BHT 2,6-di-tert-butyl-4-methylphenol BTSP bis(trimethylsilyl)peroxide BuLi butyllithium Bz benzoyl DIBAL diisobutylaluminium hydride DMSO dimethyl sulfoxide DHP 3,4-dihydro-2H-pyran DPPH 2,2-diphenyl-1-picrylhydrazyl ee enatiomeric excess eq. equation HOAc acetic acid HPLC high-performance liquid chromatography IR infrared spectroscopy IVOMD in vitro organic matter digestibility LAH lithium aluminium hydride LDA lithium diisopropylamide mCPBA 3-chloroperoxybenzoic acid Me methyl MoOPH oxodiperoxymolybdenium(pyridine)- (hexamethylphosphoric triamide) MS mass spectroscopy NMR nuclear magnetic resonance Np naphtyl PCC pyridinium chlorochromate Ph phenyl rt. room temperature TBHP tert-butyl hydroperoxide THF tetrahydrofuran THP tetrahydropyran TMS trimethylsilyl TsOH p-toluensulfonic acid UV ultraviolet spectroscopy CONTENTS ABSTRACT PAPERS INCLUDED IN THE THESIS CONTRIBUTION REPORT LIST OF ABBREVIATIONS 1. INTRODUCTION 1 1.1 Natural Products 1 1.2 Primary and Secondary Metabolism 1 1.3 Chemical Defense in Plants 3 1.4 Natural Product Synthesis 8 1.5 This thesis 9 2. METABOLITES OF PLATYPHYLLOSIDE: A DIGESTIBILITY REDUCING COMPOUND IN BIRCH (Betula pendula Roth.)I, II, II 11 2.1 Platyphylloside and its Metabolites 11 2.2 Structure-Activity Relationship 13 2.3 Determination of the Active Metabolite from Platyphylloside 17 2.4 Digestibility Inhibiting Effects of Platyphylloside in Moose (Alces Alces) 20 2.5 Platyphylloside: Conclusions 22 3. NATURALLY OCCURING ANTIOXIDANTSIV, V 23 3.1 Avenanthramides, Phenolic Antioxidants from Oats (Avena sativa) 23 3.2 Synthetic Studies Towards the Synthesis of 3-Oxygenated Carbazole Alkaloids 29 3.3 Antioxidants: Conclusions and outlook 34 4. PINE WEEVIL (Hylobius abietis) ANTIFEEDANTS FROM PINE (Pinus contorta)VI 35 4.1 Introduction 35 4.2 Results and Discussion 36 4.4 Antifeedants: Conclusions and outlook 43 5. ACKNOWLEDGEMENTS 44 1 1. INTRODUCTION 1.1 Natural Products Man has used natural products since the dawn of time as remedies for diseases, spices, narcotics, dyes, and poison for warfare and hunting. Most of these compounds were used in their crude forms and the active components were mostly not isolated until the nineteenth century. A number of these natural products are still in use today. Morphine (1), first isolated from opium (Papaver somniferum and P. setigrum)1 in 1803 is a well-known example. It is one of the most powerful analgesics known, and it also possesses strong narcotic effects. HO O H NCH H 3 HO 1 Another example is quinine (2) an anti-malaria agent isolated from the Cinchona tree. As early as in the seventeenth century, Thomas Sydenman, a Bachelor of Medicine, prescribed a mixture of powdered bark of the cinchona tree and syrup of cloves as a remedy for malaria.1 H H N HO H MeO N 2 1.2 Primary and Secondary Metabolism When discussing metabolism it is common to distinguish between primary and secondary metabolism. Primary metabolism refers to the processes producing the carboxylic acids of the Krebs cycle, α-amino acids, carbohydrates, fats, proteins and nucleic acids, all essential for the survival and well-being of the organism.2 All 1 Mann, J. Secondary Metabolism. Clarendon Press, Oxford, 1987. 2 Torssell, K. B. G. Natural Product Chemistry. A mechanistic, biosynthetic and ecological approach. Apotekarsocieteten-Swedish Pharmaceutical Press, 1997. 2 organisms possess the same metabolic pathways by which these compounds are synthesized and utilized. Secondary metabolites, on the other hand, are non-essential to life but contribute to the species’ fitness for survival.2 Secondary metabolites are also produced using other metabolic pathways than primary metabolites. These pathways are more characteristic for the particular family or genus and are related to the mechanism of evolution of species. In fact, the specific constituents in a certain species have been used to help with systematic determination, groups of secondary metabolites being used as markers for botanical classification (chemotaxonomy).2 The division between primary and secondary metabolism is not clear: and the two types are linked together because primary metabolism provides the small molecules that are the starting materials of the secondary metabolic pathways (Figure 1). CO2 + H2O (photosynthesis) hν Monosaccharides POLYSACCHARIDES CO H GLYCOSIDES 2 NUCLEIC ACIDS CINNAMIC ACID DERIVATIVES HO OH OTHER AROMATIC COMPOUNDS LIGNANS OH CH3COCO2H Shikimic acid Pyruvic acid Aromatic amino acids PEPTIDES CH COSCoA 3 Aliphatic amino acids PROTEINS Acetyl-SCoA ALKALOIDS PHENOLS H3C OH -O CCH
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