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Investigation of Plants Containing Unusual Ecdysteroids with Ring in Their Side-Chain

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Investigation of Plants Containing Unusual Ecdysteroids with Ring in Their Side-Chain Department of Pharmacognosy University of Szeged Investigation of plants containing unusual ecdysteroids with ring in their side-chain Ph.D. Thesis Attila Ványolós Szeged 2012 Table of Contents ABBREVIATIONS 1. INTRODUCTION ....................................................................................................................... 1 1.1. Structural diversity of ecdysteroids ................................................................................. 2 1.2. Pharmacological effects of ecdysteroids on mammals ................................................... 3 1.3. Aims of our studies ......................................................................................................... 5 1.4. Botanical characterization and taxonomic classification of A. reptans .......................... 6 1.5. Botanical characterization and taxonomic classification of P. vulgare .......................... 6 1.6. Botanical characterization and taxonomic classification of S. wolffii ............................. 7 1.7. Chemical constituents of A. reptans ................................................................................ 7 1.8. Chemical constituents of P. vulgare ............................................................................... 8 1.9. Chemical constituents of S. wolffii .................................................................................. 9 2. MATERIALS AND METHODS ................................................................................................... 10 2.1. Plant material................................................................................................................. 10 2.2. Reagents and standard ecdysteroid samples .................................................................. 10 2.3. General experimental procedures .................................................................................. 10 2.3.1. General methods and apparatus .............................................................................. 10 2.3.2. Chromatographic techniques .................................................................................. 11 2.4. Extraction and isolation ................................................................................................. 13 2.4.1. Extraction and prepurification of the crude extracts of A. reptans and P. vulgare 13 2.4.2. Isolation of ecdysteroids from A. reptans ............................................................... 14 2.4.3. Isolation of ecdysteroids from P. vulgare ............................................................... 15 2.4.4. Extraction and isolation of ecdysteroids from S. wolffii ......................................... 16 3. RESULTS ............................................................................................................................... 16 3.1. Isolation of ecdysteroids................................................................................................ 16 3.2. Characterization of the isolated compounds ................................................................. 20 3.3. Structure determination of the isolated ecdysteroids .................................................... 23 3.3.1. Structure determination of compounds isolated from A. reptans ........................... 23 3.3.2. Structure determination of compounds isolated from P. vulgare ........................... 25 3.3.3. Structure determination of compounds isolated from S. wolffii ............................. 28 3.3.4. Structures of the isolated ecdysteroids.................................................................... 34 4. DISCUSSION .......................................................................................................................... 37 5. SUMMARY ............................................................................................................................. 43 REFERENCES ............................................................................................................................. 44 ACKNOWLEDGEMENTS APPENDIX ABBREVIATIONS 13C NMR = carbon nuclear magnetic resonance spectroscopy 1D = one-dimensional, 2D = two-dimensional 1H NMR = proton nuclear magnetic resonance 20E = 20-hydroxyecdysone CC = column chromatography CID = collision-induced dissociation CoMFA = comparative molecular field analysis COSY = correlation spectroscopy DEPT = distorsionless enhancement by polarization transfer E = ecdysone EcR = ecdysteroid receptor EIMS = electron-impact mass spectroscopy ESIMS = electrospray ionization mass spectroscopy FID = free induction decay HMBC = heteronuclear multiple bond coherence spectroscopy HMQC = heteronuclear multiple quantum coherence spectroscopy HPLC = high-performance liquid chromatography HRESIMS = high resolution electrospray ionization mass spectroscopy MDR = multiple drug resistance MS = mass spectroscopy NOESY = nuclear Overhauser effect spectroscopy NP = normal-phase QSAR = quantitative structure-activity relationship ROESY = rotating-frame Overhauser effect spectroscopy RP = reversed-phase RP-CC = reversed-phase column chromatography RPC = rotation planar chromatography SPE = solid-phase extraction TLC = thin-layer chromatography TOCSY = total correlated spectroscopy UV = ultraviolet 1. INTRODUCTION Ecdysteroids are hormones of arthropods and many other invertebrates. The first ecdysteroid, ecdysone (E) was isolated from silkworm pupae (Bombyx mori) by German scientists, Butenandt and Karlson, in 1954.1 Ecdysteroids play essential roles in all insects, as they regulate major transitional events during insect growth: molting, metamorphosis, reproduction and diapause.2 Many of the morphological, physiological and biochemical processes that occur during molting are induced and modulated by the main molting hormone 20-hydroxyecdysone (20E), although its precursor, E, has a role independent of that of 20E.3 In the 1960s, phytoecdysteroids, the plant analogs of ecdysteroids, were identified in several plant species.4,5 So far, less than 2% of the world’s flora has been investigated for the presence of ecdysteroids, but more than 300 compounds have already been identified. The levels of ecdysteroids in plants are usually between 0.1 and 3% of the dry weight, which is 1000-fold higher than in insects.6 It should be mentioned that some crop plants, for e.g. spinach (Spinacia oleracea) and quinoa (Chenopodium quinoa), contain considerable amounts of ecdysteroids (40-300 µg/g fresh weight).7,8 Their roles in plants are still unclarified, but it is believed that ecdysteroids offer protection against non-adapted phytophagus invertebrates.9 The ready availability of ecdysteroids in different plants species has allowed pharmacological studies, which have suggested that they have many positive pharmacological properties. This is in accordance with the use of some ecdysteroid-containing plants in traditional medicine. In spite of the accumulating evidence of their beneficial pharmacological properties, their mode of action and their metabolism in mammals are still unknown.10 Ecdysteroids are not endogenous participants in the mammalian metabolism, and are not toxic to mammals. They can be toxic to insects by disrupting hormonal processes upon ingestion, which has led to the development of safe insecticides. Nevertheless, the ecdysteroids themselves are not used in the control of pests because of their high polarity and their environmental instability. In contrast, bisacylhydrazines, functional analogs of ecdysteroids, are successful and selective pest control agents.11,12 Most of the actions of ecdysteroids in insects are mediated by the intracellular ecdysteroid receptor (EcR) complex, which modifies the activities of specific gene sets. Since neither ecdysteroids nor the EcR proteins are endogenous components of mammalian cells, this system can be used in the regulation of transfected genes. Because of their low mammalian 1 toxicity, the appropriate ecdysteroid agonists can be used in the generation of ecdysteroid- inducible gene-switch systems.13,14 1.1. Structural diversity of ecdysteroids The basic chemical structure of ecdysteroids is a cyclopentano-perhydrophenanthrene (sterane) skeleton (Figure 1); the number of carbon atoms can be 19, 21, 24, 27 or 29. The C/D ring junction is generally trans, whereas the A/B ring is normally cis (5β-H) and only rarely trans (5α-H). Most ecdysteroids possess a 14α-hydroxy group and a 7-en-6-one chromophore in ring B, which results in characteristic ultraviolet (UV) absorption. Other common structural elements of ecdysteroids are the β-side-chain on C-17 and additional hydroxy groups on C-2, C-3, C-20, C-22 and C-25. The great number of possible ecdysteroid structures (more than 1000) can be explained by the variation in number, position and orientation of the hydroxy groups. Some ecdysteroids are conjugated with acids, alcohols or sugars. Additional unsaturation, or the presence of a cyclic ether or a lactone ring (5- or 6- membered) at C-17 can occur. Phytoecdysteroids are biosynthesized from cholesterol or other sterols (lathosterol, stigmasterol or brassicasterol), although the precise biosynthetic pathways involved in the production of phytoecdysteroids are unknown. Figure 1. Structure of the most common ecdysteroid, 20E. The structural diversity of ecdysteroids has provided a good opportunity for investigations of the structure–insect hormone activity relationships by means of comparative molecular field analysis (CoMFA) and 4D-quantitative structure–activity relationship (QSAR)
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