Date of Award

Summer 1989

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

James H. Yuan

Committee Member

Patricia Pleban

Committee Member

Roy L. Williams

Committee Member

John D. Van Norman

Call Number for Print

Special Collections LD4331.C45H355

Abstract

Basic research into reproductive physiology has begun to identify possible new approaches to controlling fertility. Gossypol, a natural polyphenol compound isolated from cottonseed oil, has been shown to be an effective male antifertility agent. The decomposition products of gossypol which are thought to possess more potent antifertility effects than the parent compound gossypol have been studied extensively in more recent research. The purpose of this research is to develop techniques and methods which could be used to identify decomposition products of gossypol. A model decomposition reaction by which a smaller molecule can be isolated in a pure state has been designed. Using this approach, an analytical technique has been developed which allows separation of all the major decomposition products. Gossypol was shown to be unstable in a buffered ethanolic neutral solution. Three major decomposition products were formed after incubation of gossypol in a phosphate buffer/ethanol solution at pH 7.55 for six hours. High Pressure Liquid Chromatography (HPLC) was used to separate the decomposed samples.

The semi-preparative system in particular allowed relatively large samples to be injected, and the isolation procedure then consisted of collecting fractions of interest, followed by suitable work-up procedures. Once the decomposition products were separated, a rotary evaporator was used to remove the solvent. On a repeat of the analysis, an inert gas (dry nitrogen) was used to facilitate evaporation. The identification of the decomposition products of gossypol was done by employing Fourier Transform Infrared Spectroscopy (FT-IR), Mass Spectrometry (MS) and Nuclear Magnetic Resonance Spectroscopy (NMR). As the amounts of decomposition products present were rather small, the semi-prep analytical columns provided adequate capacity to isolate the quantities necessary for MS, NMR, and FTIR. The purity of the isolated compounds was sufficient to obtain successful MS, FT-IR, and NMR data. Results from MS, FT-IR, and NMR studies strongly indicate that the identity of the fraction three decomposition product of gossypol in buffered ethanolic neutral solution is either a lactol, or a quinoid.

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DOI

10.25777/bcax-kg29

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