Pyrrolizidine alkaloids (PA's) are potentially toxic, natural occurring secondary products typically found in the plant family Heliotropiaceae, in the order Boraginales. Two closely related species of the New World genus Euploca and one species from the pantropical genus Heliotropium are being surveyed in this study. Whole plants were collected from Texas during the flowering and fruiting season. Based on previous GC-MS analysis, the PA’s of H. glabriusculum are suspected to be supinine and rinderine. Preliminary GC-MS examination of E. texana and E. racemosa revealed similar PA patterns following comparison of their chromatographic retention times and spectral data. Structural elucidation utilizing GC-MS tentatively identified the PA’s in the two Euploca species to be 9-angeloyl retronecine, helifoline, heliospathine, and the novel compound, 3’-acetyl heliospathine, or their stereoisomers. Further investigation using chromatographic and NMR techniques will determine stereochemical assignments. This is the first comprehensive PA analysis of H. glabriusculum and E. racemosa and the inaugural analyses of E. texana.

Structural analysis of pyrrolizidine alkaloids in Euploca racemosum, E. texana and Heliotropium glabriusculum

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