A chemical investigation of Tulbaghia Violacea
- Authors: Burton, Stephanie Gail
- Date: 1990
- Subjects: Liliaceae , Plants -- Analysis
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4528 , http://hdl.handle.net/10962/d1015725
- Description: Tulbaghia violacea, a member of the family Alliaceae is indigenous to the Eastern Cape and is widely used as a herbal remedy for various febrile and gastro-enteric ailments, particularly in young children. Adverse effects, and even fatalities, have been reported following treatment with the plant extract. The project has involved synthesis of model compounds, chromatographic analysis of flavonoid and other constituents of the plant, and examination of the volatile components. Some fifteen flavones were synthesised as chromatographic models and in the course of this work, the development of a new method for synthesis of carboxylic anhydrides was completed. Use of the flavone standards permitted identification of the flavonols kaempferol and quercetin in hydrolysed glycosidic plant extracts. In addition, several sugars were identified, viz., D-glucose, D-fructose, L-arabinose and D-galactose as free sugars, and D-glucose, D-galactose , 1-rhamnose, D- fucose, D-xylose, 1-arabinose and D-fructose as glycosidic sugars, by g.l.c. and g. c. - m. s. analysis of derivatives of isolated sugar mixtures. The presence in the plant extracts of steroidal saponins was also demonstrated. The sulphur compounds, 2,4,5,7-tetrathiaoctane-2,2-dioxide and 2,4,5,7-tetrathiaoctane were isolated from the plant and characterised spectroscopically. This result, together with analysis of volatiles from the plant, has led to a proposal concerning the nature and origin of sulphur compounds in Tulbaghia violacea, showing close correlation with the sulphur compounds in Allium species. Investigation of the biological activity of Tulbaghia violacea extracts showed bacteriostatic activity, particularly of extracts which had not been heated, and which had been prepared from mature plants. Treatment of isolated smooth muscle preparations with Tulbaghia violacea extracts indicated the presence of a β-adrenergic agonist having an inhibitory effect on normal muscle contraction. The results of the investigations indicate that while there may be some basis for use of the plant as an antibacterial, or to treat colic, the adverse effects, caused possibly by the sulphur compounds and/or steroidal saponins present, may override the beneficial effects.
- Full Text:
- Date Issued: 1990
- Authors: Burton, Stephanie Gail
- Date: 1990
- Subjects: Liliaceae , Plants -- Analysis
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4528 , http://hdl.handle.net/10962/d1015725
- Description: Tulbaghia violacea, a member of the family Alliaceae is indigenous to the Eastern Cape and is widely used as a herbal remedy for various febrile and gastro-enteric ailments, particularly in young children. Adverse effects, and even fatalities, have been reported following treatment with the plant extract. The project has involved synthesis of model compounds, chromatographic analysis of flavonoid and other constituents of the plant, and examination of the volatile components. Some fifteen flavones were synthesised as chromatographic models and in the course of this work, the development of a new method for synthesis of carboxylic anhydrides was completed. Use of the flavone standards permitted identification of the flavonols kaempferol and quercetin in hydrolysed glycosidic plant extracts. In addition, several sugars were identified, viz., D-glucose, D-fructose, L-arabinose and D-galactose as free sugars, and D-glucose, D-galactose , 1-rhamnose, D- fucose, D-xylose, 1-arabinose and D-fructose as glycosidic sugars, by g.l.c. and g. c. - m. s. analysis of derivatives of isolated sugar mixtures. The presence in the plant extracts of steroidal saponins was also demonstrated. The sulphur compounds, 2,4,5,7-tetrathiaoctane-2,2-dioxide and 2,4,5,7-tetrathiaoctane were isolated from the plant and characterised spectroscopically. This result, together with analysis of volatiles from the plant, has led to a proposal concerning the nature and origin of sulphur compounds in Tulbaghia violacea, showing close correlation with the sulphur compounds in Allium species. Investigation of the biological activity of Tulbaghia violacea extracts showed bacteriostatic activity, particularly of extracts which had not been heated, and which had been prepared from mature plants. Treatment of isolated smooth muscle preparations with Tulbaghia violacea extracts indicated the presence of a β-adrenergic agonist having an inhibitory effect on normal muscle contraction. The results of the investigations indicate that while there may be some basis for use of the plant as an antibacterial, or to treat colic, the adverse effects, caused possibly by the sulphur compounds and/or steroidal saponins present, may override the beneficial effects.
- Full Text:
- Date Issued: 1990
Synthetic and spectrometric investigation of 1,4-benzoxazepines
- Authors: Whittal, R D
- Date: 1990
- Subjects: Spectrum analysis , Benzodiazepines
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4381 , http://hdl.handle.net/10962/d1005046
- Description: Flavanone (2,3-dihydro-2-phenyl-4H-benzopyran-4-one) and a series of 4'- and 7-halogeno derivatives were prepared from the corresponding 2'-hydroxychalcones [1-(2-hydroxyphenyl)-3-phenyl-2-propen-l-ones], which, in turn, were synthesized by aldol condensation of substituted 2'-hydroxacetophenones with various benzaldehydes. A series of 2,3-dihydro-2-phenyl-l,4-benzoxazepin-5(4H)-ones were prepared by ring expansion of the corresponding flavanones, via the Schmidt reaction, using trimethylsilylazide and trifluoroacetic acid. A series of tetrazoles {2,3-dihydro-2-phenyl-tetrazolo[1,5-d]-1,4-benzoxazepines} were also isolated as by-products of the Schmidt reaction. Flavanone oxime was synthesized for use in Beckmann reactions, and its molecular structure was determined by x-ray crystallography. Attempts to prepare 1,4-benzoxazepinone or its 1,5-analogue via Beckmann rearrangement of flavanone oxime, with polyphosphoric acid or phosphorus pentachloride catalysts, however, were unsuccessful. Several methods for introducing Δ²-unsaturation into the benzoxazepinone system were also examined. High resolution ¹H n.m.r., computer modelling, and molecular mechanics techniques were used to determine the conformations of the heterocycles of the benzoxazepinones and tetrazoles and results are compared with earlier studies in this field. Certain trends in the fragmentation patterns were observed in the low resolution mass spectra of the benzoxazepinones and tetrazoles, and high resolution mass spectrometric data were used to explore the major fragmentation patterns of these compounds.
- Full Text:
- Date Issued: 1990
- Authors: Whittal, R D
- Date: 1990
- Subjects: Spectrum analysis , Benzodiazepines
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4381 , http://hdl.handle.net/10962/d1005046
- Description: Flavanone (2,3-dihydro-2-phenyl-4H-benzopyran-4-one) and a series of 4'- and 7-halogeno derivatives were prepared from the corresponding 2'-hydroxychalcones [1-(2-hydroxyphenyl)-3-phenyl-2-propen-l-ones], which, in turn, were synthesized by aldol condensation of substituted 2'-hydroxacetophenones with various benzaldehydes. A series of 2,3-dihydro-2-phenyl-l,4-benzoxazepin-5(4H)-ones were prepared by ring expansion of the corresponding flavanones, via the Schmidt reaction, using trimethylsilylazide and trifluoroacetic acid. A series of tetrazoles {2,3-dihydro-2-phenyl-tetrazolo[1,5-d]-1,4-benzoxazepines} were also isolated as by-products of the Schmidt reaction. Flavanone oxime was synthesized for use in Beckmann reactions, and its molecular structure was determined by x-ray crystallography. Attempts to prepare 1,4-benzoxazepinone or its 1,5-analogue via Beckmann rearrangement of flavanone oxime, with polyphosphoric acid or phosphorus pentachloride catalysts, however, were unsuccessful. Several methods for introducing Δ²-unsaturation into the benzoxazepinone system were also examined. High resolution ¹H n.m.r., computer modelling, and molecular mechanics techniques were used to determine the conformations of the heterocycles of the benzoxazepinones and tetrazoles and results are compared with earlier studies in this field. Certain trends in the fragmentation patterns were observed in the low resolution mass spectra of the benzoxazepinones and tetrazoles, and high resolution mass spectrometric data were used to explore the major fragmentation patterns of these compounds.
- Full Text:
- Date Issued: 1990