Synthesis Of 1,3-Dicinnamoyl-2-Acetylglycerol, A Natural Product Derived from Genus Populus that Demonstrates Beaver Repellent Properties
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Authors
Sheehy, Drew
Issue Date
2016
Type
Thesis
Language
Keywords
aspen , beaver , chemical ecology , defense , natural product , synthesis
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Abstract
Quaking aspen tree sprouts have been observed to be ignored by foraging beavers in favor of adult trees, despite a nutritional advantage possessed by the sprouts. This unexpected behavior has been found to be related to the presence of a yet undescribed compound present in sprout bark, concentrations of which are significantly diminished in the mature form. Furthermore, the concentration of this repellent compound is generally greater in the bark of sprouts that are descendant from an adult that had been cut down, such as by a beaver. This suggests a previously undescribed inducible defense by aspen to beaver herbivory. To confirm the structure of this compound and provide an avenue for future study, a synthesis pathway for the carbon skeleton structure was determined. The structure targeted for synthesis is an acetylated bi-cinnamic triglyceride derivative with a plane of symmetry about the central glyceric carbon. The structure was confirmed via nuclear magnetic resonance (NMR) and compared favorably to LC/MS spectra of aspen extract, but was structurally inconsistent with the repellent compound previously isolated. The inconsistency offers clues to the true structure, which is most likely a para-hydroxylated derivative of the synthetic product. A synthesis of this molecule is also proposed in this manuscript. This synthetic pathway will facilitate future study of the compound’s repellent properties on beaver and other mammals by eliminating the need for the laborious collection of natural product. Should the compound prove marketable, an economically viable production process has been established.
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In Copyright(All Rights Reserved)