Chemical analysis of selected Eastern Cape medicinal plants
- Authors: Mahanjana, Lungelwa
- Date: 2022-04
- Subjects: Medicinal plants -- South Africa --Eastern Cape , Traditional medicine --South Africa -- Eastern Cape Maps
- Language: English
- Type: Doctoral theses , text
- Identifier: http://hdl.handle.net/10948/55976 , vital:54560
- Description: In the rural parts of the Eastern Cape Province of South Africa, the use of medicinal plants to treat or manage diseases, including those associated with diabetes and HIV, is a common practice. However, the phytochemistry, safety and efficacy of these medicinal plants remain less investigated. Based on available traditional medicinal knowledge (through traditional healers, university library resources, ethnobotanical and science journals and other internet resources), traditional uses and availability, three plant species, namely Bulbine latifolia L. Wild, Dicerothamnus rhinocerotis Koek. and Olea europaea subsp. africana (Mill.) P.S. Green were selected and investigated for their hytoconstituents and biological effects. Phytochemical screening of the three medicinal plants was carried out quantitatively and qualitatively using spectrophotometric methods. Chemical profiling of the crude methanol extracts of all the plant species was successfully done by high-performance thin layer chromatography (HPTLC) and tentative identification of the secondary metabolites was achieved by liquid chromatography–mass spectrometry (LCMS). Cytotoxicity effect investigations on the crude extracts of the three species was done using the 3-[4,5- dimethylthiazole-2-yl]-2,5- hiphenyltetrazolium bromide (MTT) assay against HeLa cervical cancer cells. Isolation and purification of single compounds was done using chromatographic techniques (column chromatography (CC), and preparative thin-layer chromatography (PTLC)). Characterisation of single compounds was achieved using spectroscopic techniques such as Nuclear Magnetic Resonance (NMR), High Resolution Mass Spectrometry (HRMS), Ultra Violet Spectroscopy (UV-vis), Fourier-Transformed Infra-Red Spectroscopy (FTIR) and Single-Crystal X-ray Diffraction (XRD). For the first time from the methanol crude extract of the tubers of B. latifolia, the crystal structure of the phenylanthraquinone, knipholone (3.12) (1-(3-acetyl-2,6- dihydroxy-4- methoxyphenyl)-4,5-dihydroxy-2-methylanthraquinone), was isolated and elucidated along with its derivatives, isoknipholone (3.14), knipholone-6’-methyl (3.27). Moreover, two new compounds, (M)-8-O-β-D-glucopyranosyl-10’-α-L-rhamnopyranosyl-1,1',8',10'-tetrahydroxy 3,3'-dimethyl-[10,7'-bianthracene]-4,9,9'(10'H)-trione (3.23a) and (P)- 8-O-β-D glucopyranosyl-10’-α-L-rhamnopyranosyl-1,1',8',10'-tetrahydroxy-3,3'-dimethyl-[10,7'- bianthracene]-4,9,9'(10'H)-trione (3.23b) were isolated. , Thesis (PhD) -- Faculty of Science, School of Biomecular and Chemical Sciences, 2022
- Full Text:
- Date Issued: 2022-04
- Authors: Mahanjana, Lungelwa
- Date: 2022-04
- Subjects: Medicinal plants -- South Africa --Eastern Cape , Traditional medicine --South Africa -- Eastern Cape Maps
- Language: English
- Type: Doctoral theses , text
- Identifier: http://hdl.handle.net/10948/55976 , vital:54560
- Description: In the rural parts of the Eastern Cape Province of South Africa, the use of medicinal plants to treat or manage diseases, including those associated with diabetes and HIV, is a common practice. However, the phytochemistry, safety and efficacy of these medicinal plants remain less investigated. Based on available traditional medicinal knowledge (through traditional healers, university library resources, ethnobotanical and science journals and other internet resources), traditional uses and availability, three plant species, namely Bulbine latifolia L. Wild, Dicerothamnus rhinocerotis Koek. and Olea europaea subsp. africana (Mill.) P.S. Green were selected and investigated for their hytoconstituents and biological effects. Phytochemical screening of the three medicinal plants was carried out quantitatively and qualitatively using spectrophotometric methods. Chemical profiling of the crude methanol extracts of all the plant species was successfully done by high-performance thin layer chromatography (HPTLC) and tentative identification of the secondary metabolites was achieved by liquid chromatography–mass spectrometry (LCMS). Cytotoxicity effect investigations on the crude extracts of the three species was done using the 3-[4,5- dimethylthiazole-2-yl]-2,5- hiphenyltetrazolium bromide (MTT) assay against HeLa cervical cancer cells. Isolation and purification of single compounds was done using chromatographic techniques (column chromatography (CC), and preparative thin-layer chromatography (PTLC)). Characterisation of single compounds was achieved using spectroscopic techniques such as Nuclear Magnetic Resonance (NMR), High Resolution Mass Spectrometry (HRMS), Ultra Violet Spectroscopy (UV-vis), Fourier-Transformed Infra-Red Spectroscopy (FTIR) and Single-Crystal X-ray Diffraction (XRD). For the first time from the methanol crude extract of the tubers of B. latifolia, the crystal structure of the phenylanthraquinone, knipholone (3.12) (1-(3-acetyl-2,6- dihydroxy-4- methoxyphenyl)-4,5-dihydroxy-2-methylanthraquinone), was isolated and elucidated along with its derivatives, isoknipholone (3.14), knipholone-6’-methyl (3.27). Moreover, two new compounds, (M)-8-O-β-D-glucopyranosyl-10’-α-L-rhamnopyranosyl-1,1',8',10'-tetrahydroxy 3,3'-dimethyl-[10,7'-bianthracene]-4,9,9'(10'H)-trione (3.23a) and (P)- 8-O-β-D glucopyranosyl-10’-α-L-rhamnopyranosyl-1,1',8',10'-tetrahydroxy-3,3'-dimethyl-[10,7'- bianthracene]-4,9,9'(10'H)-trione (3.23b) were isolated. , Thesis (PhD) -- Faculty of Science, School of Biomecular and Chemical Sciences, 2022
- Full Text:
- Date Issued: 2022-04
Reactions towards the synthesis of the uncommon P57 cymarose moiety
- Authors: Mahanjana, Lungelwa
- Date: 2013
- Subjects: Chemistry, Organic , Organic compounds -- Synthesis
- Language: English
- Type: Thesis , Masters , MTech
- Identifier: http://hdl.handle.net/10948/6711 , vital:21136
- Description: The work described in this study aims to investigate methods that will improve a lengthy synthetic pathway in the synthesis of the P57 cymarose moiety, and to examine the conformational structure of certain glycosides in order to shed light on the problematic stereochemical issues surrounding the formation of the cymarose glycosyl donor. The cymarose moiety forms part of the trisaccharide derivative present in P57, an appetite suppressant molecule. Modification of reaction steps in the conversion of the stereochemistry at C-3 of a previously reported synthesis of the P57 cymarose moiety was carried out. The first step was the selective oxidation of D-glucal using Pd/C in the presence of acetonitrile. These reaction conditions are more appropriate for the oxidation step to avoid decomposition of the formed molecules. Successive protection of the free OH groups was followed by NaBH4 reduction under stereo-controlled conditions, influenced by CeCl3•7H2O. However, the reduced product could not be isolated from the starting material and this led to ambiguous results when attempting to confirm whether the conversion of the stereochemistry at C-3 had occurred or not. The effect of reaction conditions, such as change in reaction temperature, during the preparation of the cymarose glycosyl donor was studied in order to find suitable reaction conditions to produce α,β-allo derivatives with high stereoselectivity. Compared to the reported synthetic method, this set-up gave improved yields with, unfortunately, similar or slightly lower selectivity to the formation of α-altro:α,β-allo derivative. Examination of the conformational structure of the allal derivative, in order to understand the mechanism at work during the placement of the directing group at C-2, was carried out using molecular modelling. The mechanistic implications of this very short study are discussed and it provides some insights into the likely pathway of the iodination reaction and its selectivity in particular, to the D-allose system.
- Full Text:
- Date Issued: 2013
- Authors: Mahanjana, Lungelwa
- Date: 2013
- Subjects: Chemistry, Organic , Organic compounds -- Synthesis
- Language: English
- Type: Thesis , Masters , MTech
- Identifier: http://hdl.handle.net/10948/6711 , vital:21136
- Description: The work described in this study aims to investigate methods that will improve a lengthy synthetic pathway in the synthesis of the P57 cymarose moiety, and to examine the conformational structure of certain glycosides in order to shed light on the problematic stereochemical issues surrounding the formation of the cymarose glycosyl donor. The cymarose moiety forms part of the trisaccharide derivative present in P57, an appetite suppressant molecule. Modification of reaction steps in the conversion of the stereochemistry at C-3 of a previously reported synthesis of the P57 cymarose moiety was carried out. The first step was the selective oxidation of D-glucal using Pd/C in the presence of acetonitrile. These reaction conditions are more appropriate for the oxidation step to avoid decomposition of the formed molecules. Successive protection of the free OH groups was followed by NaBH4 reduction under stereo-controlled conditions, influenced by CeCl3•7H2O. However, the reduced product could not be isolated from the starting material and this led to ambiguous results when attempting to confirm whether the conversion of the stereochemistry at C-3 had occurred or not. The effect of reaction conditions, such as change in reaction temperature, during the preparation of the cymarose glycosyl donor was studied in order to find suitable reaction conditions to produce α,β-allo derivatives with high stereoselectivity. Compared to the reported synthetic method, this set-up gave improved yields with, unfortunately, similar or slightly lower selectivity to the formation of α-altro:α,β-allo derivative. Examination of the conformational structure of the allal derivative, in order to understand the mechanism at work during the placement of the directing group at C-2, was carried out using molecular modelling. The mechanistic implications of this very short study are discussed and it provides some insights into the likely pathway of the iodination reaction and its selectivity in particular, to the D-allose system.
- Full Text:
- Date Issued: 2013
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