published_or_final_version / Civil and Structural Engineering / Master / Master of Philosophy

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Oil-bearing plants are important sources of edible oil and proteins; they have attracted attention recently because of their antioxidant, antimicrobial and anti-inflammatory properties. The objective of this work was to investigate the nature of phenolic compounds in oil-bearing plants and the effects of phenolic compounds on protein isolates from soybean and flaxseed. Proteins were isolated from full-fat and defatted soybean and flaxseed using sodium hydroxide extraction and isoelectric precipitation. Free phenolic compounds were extracted from the oil-bearing plants and protein isolates using methanol; for bound phenolic compounds the oil-bearing plants and proteins were subjected to basic and acidic hydrolysis followed by methanol extraction. Total free and bound phenolic compounds were determined by spectrophotometric analysis. Reversed phase-HPLC was used for separation of individual phenolic compounds, which were identified by mass spectrometry (MS). Molecular characteristics and biological properties of the protein isolates were studied using RP-HPLC, polyacrylamide gel electrophoresis (PAGE) and MS. Thermal and gelation properties of protein isolates were investigated using differential scanning calorimetry (DSC) and rheometry. Generally, bound phenolic compounds (20%-30% of total phenolic content) were higher in protein isolates from flaxseed than in protein isolates from soybean (10%-20% of total phenolic content). With flaxseed protein isolates, removal of phenolic compounds showed little effect on the electropherotic behavior of the proteins or the protein subunits. Native-PAGE. SDS-PAGE and RP-HPLC for the peptides profiles of hydrolyzed protein isolates from both full-fat and defatted soybean revealed the removal of free and bound phenolic compounds affect on the biological properties of protein isolates. Removal of free and bound phenolic compounds affected the thermal stability and gelation properties of protein isolates from flaxseed and soybean.

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A new method for the acetalization of carbonyl compounds using chlorotrimethylsilane under mild conditions is described. Carbonyl compounds are acetalized by ethylene glycol with chlorotrimethylsilane. / Two isomeric methyl olivetolates were synthesised by the condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the corresponding electrophilic components. This reaction has clearly indicated the discriminative behaviour of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene towards different electrophilic sites thus leading to regio-selectivity. / A new method for the synthesis of olivetol is described. This method provides a shorter route to olivetol from acyclic precursors. / A new synthesis of (DELTA)('1)-tetrahydrocannabinol is described. The synthesis is patterned after biogenetic considerations. / A new method for the synthesis of poly (beta)-carbonyl compounds using diketene and enol silyl ethers is described. / The possibility of synthesising gossypol by the cyclo-aromatization procedure was investigated.

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