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Terpenoids from two British Columbia nudibranchs

University of British Columbia

The two British Columbia nudibranchs Cadiina luteomarginata and Acanthadoris nanaimoensis have sweet fragrances. The possible importance of odours in the interactions of marine organisms initially aroused our chemical curiosity. The results of our research concerning the structural investigation of seven terpenoids obtained from the organic extracts of these two opisthobranch molluscs is presented in this thesis. Five of the molecules isolated from luteomarginata have been identified as furodysin (53), furodysinin (54), microcionin-2 (55), albicanyl acetate (51) and albicanol (52). A sixth molecule, luteone (57) which gives the sweet fragrance to C. luteomarginata has been partially characterized . A crystalline derivative of this methyl ketone has been submitted for X-ray diffraction analysis. The sweet fragrance of A. nanaimoensis has been related to the presence of a sesquiterpenoid (existing as two constitutional isomers, in a 5:1 ratio). Three hypothetical structures based on spectral analysis, chemical reactions and biosynthetic reasoning are proposed. The biological origin of the seven terpenoids has also been investigated and is discussed in this thesis.

Text

2010-03-24

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http://hdl.handle.net/2429/22453

Chemistry

University of British Columbia

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