Kohls, Sarah and Scholz-Böttcher, Barbara M. and Teske, Jörg and Zark, Patrik and Rullkötter, Jürgen (2012) Cardiac glycosides from Yellow Oleander (Thevetia peruviana) seeds. Phytochemistry, 75. pp. 114-127. ISSN 0031-9422

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Abstract

Thevetia cardiac glycosides can lead to intoxication, thus they are important indicators for forensic and pharmacologic surveys. Six thevetia cardiac glycosides, including two with unknown structures, were isolated from the seeds of the Yellow Oleander (Thevetia peruviana (Pers.) K. Shum., Apocynaceae). LCESI+– MS(/MS) analysis under high-resolution conditions used as a qualitative survey of the primary glycosides did not lead to fragmentation of the aglycones. Acid hydrolysis of the polar and non-volatile thevetia glycosides under severe conditions yielded the aglycones of the thevetia glycosides and made them amenable to GC–MS analysis. Comparison of mass spectral fragmentation patterns of the aglycones, as well as high-resolution mass spectrometric and NMR data of four of the primary thevetia glycosides including the two unknowns, revealed the structures of the complete set of six thevetia glycosides. The identified compounds are termed thevetin C and acetylthevetin C and differ by an 18,20-oxido- 20,22-dihydro functionality from thevetin B and acetylthevetin B, respectively. The absence of an unsaturated lactone ring renders the glycosides cardio-inactive. The procedures developed in this study and the sets of analytical data obtained will be useful for screening and structure assessment of other, particularly polar, cardiac glycosides.

Item Type:	Article
Uncontrolled Keywords:	Thevetia peruviana, Apocynaceae, Yellow Oleander seeds, Thevetia cardiac glycosides, High-resolution mass spectrometry NMR spectroscopy
Subjects:	Science and mathematics Science and mathematics > Chemistry Science and mathematics > Life sciences, biology Science and mathematics > Plants (botany) Technology, medicine, applied sciences > Medicine and health
Divisions:	Faculty of Mathematics and Science > Institute for Chemistry and Biology of the Marine Environment (ICBM)
Date Deposited:	28 Feb 2014 11:39
Last Modified:	28 Feb 2014 11:39
URI:	https://oops.uni-oldenburg.de/id/eprint/1797
URN:	urn:nbn:de:gbv:715-oops-18780
DOI:	doi:10.1016/j.phytochem.2011.11.019
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