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Structural Investigation of the Natural Products Composition of Selected South African Seaweeds

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Structural Investigation of the Natural Products Composition of Selected South African Seaweeds STRUCTURAL INVESTIGATION OF THE NATURAL PRODUCTS COMPOSITION OF SELECTED SOUTH AFRICAN SEAWEEDS. By Mwangi Henry Maina. (MSc, B.Ed Science) A thesis submitted in partial fulfillment of the requirement for the award of the degree of Doctor of Philosophy in the Faculty of Natural Sciences University of the Western Cape Department of Chemistry Faculty of Natural Sciences University of the Western Cape Supervisor: Prof. Wilfred T. Mabusela March 2014 ABSTRACT Recently, a great deal of interest has developed towards the isolation of bioactive compounds from marine sources due to their numerous health benefits. Furthermore, marine algae are valuable sources of structurally diverse metabolites with scientifically proven therapeutic claims. The cell walls are rich in sulfated polysaccharides such as fucoidans in brown algae, carrageenans in red algae and ulvans in green algae. These sulfated polysaccharides exhibit many beneficial biological activities such as anticoagulant, antiviral, antioxidative, anticancer and immunomodulating activities. They have great potential for further development as products in cosmeceutical, pharmaceutical and nutraceutical areas. Although the mechanism of action is still not clear, their biological activities could be mainly attributed to their major secondary metabolites namely; phlorotannins, terpenoids and fucoidans. There was use of comprehensive chromatographic separations and a full analysis of isolates using one or other of the spectroscopic techniques. Antioxidant and cytotoxicity tests were perfomed in details for Ecklonia maxima. Furthermore, structural and electronic features of the phlorotannins were compared in an attempt to provide an explanation for the differences in their radical scavenging properties. In this regard, two main radical scavenging mechanisms, hydrogen atom transfer (HAT) and electron transfer (ET), were assessed in order to determine the preferred mode of radical scavenging. Fully relaxed geometry optimizations of the neutral and the radical species were performed utilizing DFT/B3LYP and DFT/UB3LYP methods respectively. In further studies, the structural and functional properties of sulfated polysaccharides from the three brown and one red seaweeds were investigated. This was through detailed analysis of chemical composition of crude and purified polysaccharides using PMP-derivatization of hydrolysed sugars, anion exchange, molecular weight determination, ion chromatography, FT-IR, NMR to ii methylation analysis. The work reports isolation and characterization of compounds from four algae: Ecklonia maxima, phlorotannin derivatives, namely phloroglucinol (22), eckol (23), 7- phloroeckol (24), 2-phloroeckol (25) and a sterol, 24-ethylidine cholesterol (26); Splachinidium rugosum, 24-ethylidine cholesterol (26), 1, 3-Dicapryloyl-2-oleoylglycerol (27), E-3,7,11,15- tetramethylhexa dec-2-en-1-ol (phytol) (28); Macrocystis angustifolia, 24-ethylidine cholesterol (26); a red seaweed Aeodes orbitosa, and E-3, 7, 11, 15-tetramethylhexadec-2-en-1-ol (28) and 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7, 8,9,11,12,14,15,16,17-dodecahydro-1 H-cyclopenta[a]phenanthren-3-ol (β-sitosterol) (29). Experimental findings and theoretical predictions of phlorotannins indicated that the radical scavenging activities followed the order 22 < 23 < 25 < 24. Theoretical studies further indicated the ET mechanism is more significant than the HAT mechanism due to the high BDE values. Their polysaccharide structures were tentatively shown to have a backbone of (13) and (14) linkages with sulfate groups at O-2 and O-2, 3 positions. The only red algae studied contained, 2-O-methyl-D-galactose with (13) and (14)-glycosidic linkages possessing sulfate groups at positions 2 and 6. KEYWORDS: brown algae; phlorotannins; fucoidan, radical scavenging activity; hydrogen atom transfer mechanism. iii DECLARATION I, Henry Maina Mwangi hereby declare that this work is my original dissertation and to my knowledge, it has not been submitted anywhere else for the award of a degree at any other University. Date ………………………………… Signed …............................................................ iv ACKNOWLEDGEMENTS I would like to express my sincere gratitude to my supervisor Prof. Wilfred T. Mabusela for his tireless and persistent effort and great guidance without which this work could not have been accomplished. I am very grateful for the opportunity to work with this esteemed scientist. He has the deepest enthusiasm as well as faith towards chemistry of brown algae. He introduced me to the herbal and carbohydrate chemistry little by little and got me to understand nutraceutical properties of algae. Special thanks to Dr. Ahmed Mohammed at the University of Western Cape for helping me advance my scientific thinking. His pedagogical touch to science has led us to many scientific discussions of both the deepest chemistry as well as in the interesting field of natural products. My most humble gratitude to Prof. Martin Onani at the University of Western Cape for creating great opportunities that enabled me to attend wonderful international conferences and share my research findings to the rest of the world. Dr. Ntevheleni of CSIR Ithemba Laboratories for proof-reading the overall thesis. I thank the staff in the Department of Chemistry for all the help they provided me for my problems in the lab or office. To Lamicare Ltd for the financial support; I am greatly indebted to them all. To my fellow post graduate students during the whole period of my research Ndikho, Carlo, Zizipho, Masande, Asanda, Mduduzi, Koki, Zandile, all of the University of the Western Cape, each one of them contributed greatly towards the completion of this work. My sincere gratitude goes to you all as honest friends, and those in the other labs, for your wise advice. You have provided me plenty of places and occasions to balance my life with non-scientific matters and concerns. Ultimately but not the least, I would not have made it this far were it not for the hand of the Lord God. I thank the Almighty for the gift of good health, strength, endurance, inquisitive and critical thinking mind. v DEDICATION Special thanks to my loving wife Monica and children Edward and Winnie, who has been an inspiration to my struggle over the years. Thanks to my adoring Mum and Dad for their boundless moral support and love in my endeavors into this long journey of my studies. And may the Lord God bless them in a mighty way in everything they do. vi LIST OF PUBLICATIONS Parts of the work reported in this thesis have been published, submitted or prepared for submission as manuscripts for publication in some journals. I. Henry, M. Mwangi, Christie, N, Van Der Westhuizen, J., Jeanine Marnewick, J. and Wilfred, T. Mabusela and Mwadham, M. K (2013). Isolation, identification and radical scavenging activity of phlorotannin derivatives from brown algae, Eklonia maxima species: An Experimental and theoretical study. Free Radicals and Antioxidants 3: S1-S3 http://dx.doi.org/10.1016/j.fra .2013.10.006. II. Henry, M. Mwangi., Martin, O. Onani., Van Der Westhuizen, J., and Wilfred, T. Mabusela. Phloroglucinol and sterol derivatives from the brown alga Ecklonia maxima and their anticancer properties. (Manuscript under review) III. Henry, M. Mwangi., Van Der Westhuizen, J., and Wilfred, T. Mabusela. Sulfated polysaccharide from the brown seaweed Ecklonia maxima, Splachinidium rugosum and Macrocystis angustifolia. (Manuscript) vii Table of contents Abstract ii Declaration iv Acknowledgement v Dedication vi List of publications vii List of abbreviations xvii List of figures xx List of plates xxiii List of schemes xxiii List of tables xxiv Chapter 1: Introduction 1.1 Background 1 1.1.1 Medicinal uses of seaweeds 2 1.1.2 Consumption of seaweeds 6 1.2 Polyphenolics 7 1.2.1 Phlorotannins 8 1.2.1.1 Structural diversity 9 1.2.1.2 Isolation of phlorotannins 10 1.2.1.3 Spectrometric and chromatographic analysis of phlorotannins 11 1.2.1.4 Biological roles of phlorotannins 12 1.2.1.4.1 Primary roles of phlorotannins 12 1.2.1.4.2 Secondary roles of phlorotannins 13 1.2.1.4.3 Medicinal roles of phlorotannins 14 1.3 Seaweeds carotenoids 16 1.4 Seaweeds triterpenoid saponins 18 1.5 Seaweeds lipids 18 viii 1.6 Polysaccharides 19 1.6.1 Structural analysis of polysaccharide s 23 1.6.1.1 GC/MS (Gas Chromatography Mass Spectrometry) 24 1.6.1.2 IEC (Ion Exchange Chromatography) 25 1.6.1.3 Derivatization of carbohydrates for HPLC 25 1.6.1.4 Determination of linkage patterns 26 1.6.1.4.1 Reductive Cleavage Analysis 27 1.6.1.4.2 Peroxidation 28 1.7 Sources and structural characterization of fucoidans 30 1.7.1 Sources 30 1.7.2 Effect of seasonality and locality on fucoidan levels in brown algae 32 1.7.3 Extraction of fucoidan 32 1.7.4 Chemical hydrolysis (mild/partial, for structural analysis) 34 1.7.5 Structural characterization 34 1.7.5.1 Position of sulfate groups 36 1.7.6 Biological activities of fucoidan 37 1.7.7 Applications of Fucoidan and its Oligosaccharides 39 1.8 Antioxidant properties 40 1.9 General information on algae 42 1.9.1 Class Phaeophyceae 42 1.10 Problem statement 46 1.11 Justification 47 1.12 Hypothesis 47 1.13 Objectives 47 1.13.1 General objectives 47 1.13.2 Specific objectives 47 Chapter 2: Materials and methods 2.1 Experimental activities 49 2.1.1 Reagents, equipment and materials 49 2.1.1.1 Chemicals and solvents 49 ix 2.1.1.2 Equipment 49 2.1.1.3 Chromatography 50 2.1.1.3.1 Column chromatography (CC) 50 2.1.1.4 Spectroscopy 51 2.1.1.4.1 Nuclear magnetic resonance
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