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Characterization and Biological Evaluation of Secondary Metabolites from Vernonia Oligocephala, Chemistry and Applications of Green Solvents

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Characterization and Biological Evaluation of Secondary Metabolites from Vernonia Oligocephala, Chemistry and Applications of Green Solvents Characterization and Biological Evaluation of Secondary Metabolites from Vernonia oligocephala, Chemistry and Applications of Green Solvents A Dissertation Submitted for The Fulfillment of the Requirement for the Award of Degree of Doctor of Philosophy in Chemistry By Rizwana Mustafa Department of Chemistry The Islamia University of Bahawalpur Bahawalpur-63100, Pakistan 2016 Summary SUMMARY The present thesis consists of two parts, Part A deals with the isolation of natural products. Plants are being used as medicine since the beginning of human civilization, perhaps as early as origin of man. Healing powers are reported to be present in plants and therefore it is assumed that they have medicinal properties. The present Ph. D thesis deals with isolation of bioactive constituents from medicinally important plant of Pakistan namely Vernonia oligocephala. Part B deals with green solvents (ILs) and their chemistry. Mixtures of ionic liquids, ILs, and molecular solvents are used because of practical advantages. Solvation by mixture of solvents is, however, complex because of preferential solvation. Part A Characterization and biological evaluation of secondary metabolites from Vernonia oligocephala Part B Chemistry and applications of green solvents Page # iv Summary Part A: Characterization and biological evaluation of secondary metabolites from Vernonia oligocephala The genus Vernonia is the largest genus among the vernoniae tribe with up to 1000 species. It is found mostly in tropical regions, mostly grow in marshy and wet areas, tropical forest, tropical savannahs, desert, and even in dry frosty regions. It consists of annuals, lianas, trees, shrubs and perennials. The Genus Vernonia is important for medicinal, food and industrial uses e.g. the leaves of V. amygdalina, and V. colrarta are eaten as food. The methanolic extract Vernonia oligocephala results in isolation and structural isolation of one new compound (142) and eight known compounds (43, 44, 126, 143-147) were isolated. New Compounds isolated from V. oligocephala 1 Characterization of Oligocephlate (142) 20 30 18 12 22 25 26 17 28 9 14 16 29 1 O 10 3 5 7 27 O 23 24 142 R. Mustafa et al., J. Chem. Soc. Pak., 35, 972-975 (2013). Compounds isolated for the first time from V. oligocephala 1. β-Sitosterol (126) 2. Oleanolic Acid (143) Page # v Summary 3. 5,7,4'-Trihydroxyflavone (144) 4. Apigenin-7-p-Coumerate (145) 5. Kaemferol (44) 6. 1sorhamnetin (146) 7. β-Sitosterol 3-O-β-D-glucopyranoside (147) 8. Quercetin (43) 29 29 30 28 3' OH 21 26 19 21 2' 18 20 25 23 8 5' 17 HO 9 O 2 17 11 28 OH 1 12 27 25 26 13 6' 19 H 16 9 6 3 9 14 1 10 1 15 O 5 10 H H 3 5 7 27 3 H OH O 7 HO RO 5 H 23 24 143 144 126 R = H 147 R = Glucose 3' 2' OH 8" 3' 8 HO OH HO O 5' 9'' 2' 8a 2 6' 2" 6" O 8 5' 6 4a 1" 9 O 2 5" 3" 6' OH O 6 3 10 OH O 5 145 OH O 44 OCH3 OH OH OH 2' 2' 8 HO O 5' HO 8 O 5' 2 6' 8a 6' 6 4a 6 4a 3 5 OH 5 OH OH O OH O 146 43 The structures of these compounds were elucidated by spectral studies including UV, IR, EI-MS, HR-EI-MS, FAB-MS, HR-FAB-MS, NMR techniques including 1D (1H, 13C) and 2D NMR (HMQC, HMBC, COSY, NOESY) and chemical transformations. The new compound Page # vi Summary oligocephalate (142) were tested against the enzyme α-glucosidase, which displayed inhibitory activity against this enzyme. Part B: Chemistry and applications of green solvents Mixtures of ionic liquids, ILs, and molecular solvents are used because of practical advantages. Solvation by mixture of solvents is, however, complex because of preferential solvation. We probed this phenomenon by examining the spectral response of a solvatochromic dye, 2,6-dichloro-4-(2,4,6- triphenylpyridinium-1yl)phenolate (WB), in mixtures of the ILs 1-(1-butyl)-3- methylimidazolium acetate, (1-methoxyethyl-3-methylimidazolium acetate, with dimethyl sulfoxide, DMSO and water, W, over the entire mole fraction () range, at 15, 25, 40, and 60 °C. The empirical polarity of the mixtures, ET(WB) showed nonlinear dependence on DMSO and W due to dye preferential solvation. We treated the solvatochromic data by a model that includes the formation of the “mixed” solvents IL-DMSO, and IL-W; the concentrations of these third components were calculated from density data. Solvent exchange equilibrium constants in the solvation layer of WB (ϕ) were calculated; their values showed that IL-DMSO and IL-W are the most efficient solvent in each medium. Due to its hydrogen-bonding capacity, IL-W is more efficient than IL-DMSO. We used the results of molecular dynamics simulations to corroborate the conclusions drawn. Our solvatochromic results are relevant to cellulose dissolution in IL-DMSO because the same interaction mechanisms (solvophobic; hydrogen bonding) are determinant to dye solvation and biolpolymer dissolution. R. Mustafa et al., The Journal of Physical Chemistry B, (Submitted). Page # vii Chapter # 01 Introduction CHAPTER# 1 INTRODUCTION Natural products Medicinal Importance of Natural Products and Bioactive Secondary Metabolites Page # 1 Chapter # 01 Introduction 1 The Importance of Medicinal Plants With the beginning of life on earth, the association of human and animal with the plants starts, because the supply of oxygen, shelter, food and medicine to them by plants. With the passage of time, when human societies start forming, they start to study plant according to the necessities of life and start to categories it according to their uses. From the multiple uses of plants, their ability to heal can be recorded from earliest of myths. With the passage of time the coding of the plants continue according to the ability to ease pain and to treat the diseases. This plant based medicine system start primarily from the local area that in future lead to well develop medicinal system; the Ayurvedic and Unani of the Indian subcontinent, the Chinese and Tibetan of other parts of Asia, the Native American of North America, the Amazonian of South America and several local systems within Africa. World Health Organization (WHO) reported that about 70% world population use plants as primary health remedy, 35,000 to 70,000 species has been used up to now for medicine, from the 250,000 species of plants 14-28% occurred all around the world (Farnsworth NR 1991; Akerele 1992; Fransworth 1992; Padulosi S 2002) and almost 35-70% species of all medicinal plants are being used world-wide (Padula De 1999). Up to now more than 50 major medicines has been formed from the tropical pants. From the 250,000 species of higher plants from the whole world, only 17% has been properly investigated for their active biological constituents (Fransworth 1992; Moerman 2009). Due to this reason and of high chemical and biological diversity of plants there is a Page # 2 Chapter # 01 Introduction lot of renewable sources in the plant area that can help in the development of pharmaceuticals (Moerman 2009). Table 1. Important drugs produced by medicinal plants Sr. Drug Structure Source Use Referenc No e OH 1 Vinblastine N Catharanthus roseus Anticancer Bagg (2000) H N N H H CO 3 H O H3CO N OAc OH O OCH3 2 Ajmalacine Catharanthus roseus Anticancer, (Wink N H 1998) N H H Hypotensive O H H3CO O 3 Rescinna H CO Rauvolfia serpentina Tranquilizer (Fife 1960) 3 N N mie H H H O H O OCH3 H3CO OCH O 3 OCH3 OCH3 4 Reserpine OCH3 Rauvolfia serpentina Tranquilizer (Baumeister O OCH3 N H O OCH3 H3CO N 2003) H H OCH H3COOC 3 5 Quinine Cinchona sp. Antimalarial, (Hanbury OCH3 N 1874) OH N 6 Pilocarpine H3C Pilocarpus jaborandi Antiglucoma (Rosin 1991) H H CH3 O N O N O 7 Cocaine H3C N Erythroxylum coca Topical (Aggrawal OCH3 Anaesthetic 1995) O O Page # 3 Chapter # 01 Introduction 8 Morphine HO Papaver somniferum Painkiller (Smith 2007) O H H N CH3 HO 9 Codeine H3CO Papaver somniferum Anticough (Codeine 2011) O H H N CH3 HO 10 Atropine H3C N Atropa belladonna Spasmolytic, WHO OH Cold O O 11 Cardiac Digitalis sp. For congestive(Newman O glycosides heart failure 2008) OAc HO O O OH OH OH 12 Taxol Taxus baccata Breast and(Wani 1971) AcO O OH ovary cancer O O NH O H O AcO OH OH O O 13 Berberine O Berberis Leishmaniasis (Exell O 2007) N+ H3CO OCH3 H C 14 Pristimerin 3 COOCH3 Celastrus paniculata Antimalarial (King 2009) CH3 H3C H CH3 O CH3 HO CH3 OH 15 Quassinoids O Ailanthus Antiprotozoal (Fiaschetti HO OH 2011) O H H O O H H Page # 4 Chapter # 01 Introduction 16 Plumbagin O Plumbago indica Antibacterial, (van der Vijver Antifungal 1972) O OH 17 Diospyrin O OH Diospyros Montana Antifungal (Ray 1998) O OH O O 18 Gossypol Gossypium sp. Antispermato (Polsky OH O OH HO OH 1989) OH O HO 19 Allicin O- Allium sativum Antifungal, (Cavallito S+ 1944) S Amoebiasis 20 Ricin Ricinus communis Abundant (Lord 1994) O protein Source HN N N N N N O N H CO 21 Emetine 3 Cephaelis ipecacuanha Amoebiasis (Wiegrebe N 1984) H3CO H H H OCH3 HN OCH3 22 Glycyrrhizi COOH Glycyrrhizia glabra Antiulcer (I. Kitagawa H O n 2002) HOOC HO O HO H O O O HO H HO OH O 24 Nimbidin OAc Azadirachta indica Antiulcer (Santhaku H3CO H mari 1981) O H O O O OCH3 Page # 5 Chapter # 01 Introduction 25 Catechin OH Acacia catechu Antiulcer (Zheng 2008) HO O OH OH OH 26 Sophoradin H3C CH3 Sophora subprostrata Antiulcer (Kazuaki OH 1975) HO CH3 H3C CH3 CH 3 OH O 27 Magnolol Magnolia bark Peptic ulcer (Alice 1981) HO OH 28 Forskolin Coleus forskohlii Hypotensive, (Bernard OH O Cardiotonic 1984) OH OAc H OH 29 Digitoxin, O Digitalis thevetia Cardio tonic (Belz 2001) OH OH HO H Digoxin O O H OH O O O O H H OH 30 Indicine O- Heliotropium indicum Anticancer (Powis N+ N-oxide 1979) OH O HO O OH O 31 Homoharr N Cephalotaxus Anticancer (Kantarjia H ingtonine O and O O O Cancer.
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