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UBC Theses and Dissertations

Studies of N. sylvestris plant cell cultures in the biotransformation of dibenzylbutanolides Lam, Edward Charles


The studies in this thesis investigate the possible use of plant cell cultures in combination with synthetic chemistry in developing new and inexpensive routes to podophyllotoxin (1) and related aryltetralins. Also of some interest was the characterization of reaction parameters involved in successfully performing biotransformations using these cultures. To that end 65, 113, and 114 were obtained or synthesized from readily available aromatic aldehydes, and employed in a "one-pot" tandem conjugate addition to produce 111 and 112. The substrates 108, 109, and 110 were then readily obtained by debenzylation. Biotransformation of these substrates was then carried out using peroxidase-rich broth from plant cell cultures of Nicotiana sylvestris as a reaction medium. [Figures.] Biotransformation of dibenzylbutanolide 108 with broth from 10 day old cell culture was found to result in the production of ketone 128. The effects of such factors as culture age, hydrogen peroxide level, and peroxidase activity on the outcome of the biotransformation were investigated. It was found that using broth from older, 30 day old cultures resulted in fragmentation of the substrate, giving 131 and 132. The biotransformation of dibenzylbutanolide 109 was also carried out, and was also found to give ketone 128. A similar outcome was observed when compound 110 was subject to biotransformation, which gave ketone 139 as the product. [Figures.]

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