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Colegate, Steven M. ; Gardner, Dale R. ; Betz, Joseph M. ; Fischer, Ottmar W. ; Liede-Schumann, Sigrid ; Boppré, Michael:
Pro-toxic 1,2-Dehydropyrrolizidine Alkaloid Esters, including unprecedented 10-membered macrocyclic diesters, in the medicinally-used Alafia cf. caudata and Amphineurion marginatum (Apocynaceae: Apocynoideae: Nerieae and Apocyneae).
In: Phytochemical Analysis.
Bd. 27
(2016)
Heft 5
.
- S. 257-276.
ISSN 1099-1565
DOI: https://doi.org/10.1002/pca.2624
Abstract
However, attraction of pyrrolizidine alkaloid-pharmacophagous insects suggested their presence in Alafia cf. caudata Stapf (Nerieae:Alafiinae) and Amphineurion marginatum (Roxb.) D.J. Middleton (Apocyneae: Amphineuriinae), both used as medicinal plants.Objective – To confirm the presence of dehydropyrrolizidine alkaloids in Alafia cf. caudata and Amphineurion marginatum andidentify their structures.Methods – Methanol extracts of air-dried roots, stems and leaves of non-flowering plantswere analysed using HPLC-ESI(+)MS andMS/MS or collision-induced dissociation MS in low and/or high resolution modes. Pyrrolizidine alkaloids were tentatively identifiedbased on the mass spectrometry data. Solid phase extraction combinedwith semi-preparative HPLC were used to isolate majoralkaloids. Structures were elucidated using NMR spectroscopy.Results – Monoesters of retronecine with senecioic, hydroxysenecioic or syringic acids were identified in roots of Alafia cf.caudata. Two unprecedented 10-membered macrocyclic dehydropyrrolizidine alkaloid diesters were isolated from roots ofAmphineurion marginatum. Pyrrolizidine alkaloids were detected in root and leaf material of Alafia cf. caudata at 0.34 and0.01% dry weight (DW), and 0.13, 0.02 and 0.09% DW in root, leaf and stem material of Amphineurion marginatum.Conclusions – The presence of pro-toxic dehydropyrrolizidine alkaloids suggests that medical preparations of these plants posepotential health risks to consumers. Dehydropyrrolizidine alkaloids are evidently more widespread in Apocynoideae than previouslyassumed, and it would seem rewarding to study other members of this family for the presence of pyrrolizidines,dehydropyrrolizidines and dihydropyrrolizines.