Cardiac glycosides from Yellow Oleander (Thevetia peruviana) seeds.

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). LC-ESI⁺-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.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Kohls S,Scholz-Böttcher BM,Teske J,Zark P,Rullkötter J

doi

10.1016/j.phytochem.2011.11.019

subject

Has Abstract

pub_date

2012-03-01 00:00:00

pages

114-27

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(11)00506-1

journal_volume

75

pub_type

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