Pyrrolizidine alkaloids (PA’s) are potentially toxic, naturally occurring secondary products typically found in the plant family Boraginaceae. Previous work has allowed the elucidation of unsaturated PA 9-monoesters stereoisomers, such as lycopsamine, echinatine, and intermedine. As part of a continuing alkaloid analysis of the family Boraginaceae, plant samples Cryptantha costata, Cryptantha recurvata, Cerinthe major, and Omphalodes alienoides were collected during the past two years and subsequently analyzed by nuclear magnetic resonance spectroscopy (NMR). Comparison of these known unsaturated PA 9-monoesters to the previously listed plants will allow us to predict preliminary assignments of stereochemical configurations at the chiral 7, 8, and 3’ positions. This will further establish the structural elucidation of PA’s in our lab.

NMR analysis of pyrrolizidine alkaloid monoesters from the plant family Boraginaceae

253rd National Meeting (2017)

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