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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)

Title data

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. Vol. 27 (2016) Issue 5 . - pp. 257-276.
ISSN 1099-1565
DOI: https://doi.org/10.1002/pca.2624

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER137151
Keywords: Amphineurine; Health risk; Hydroxysenecioylretronecine; Isoshimbaine; Marginatine; Pyrrolizidine alkaloid-pharmacophagous insects; Shimbaine
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Plant Systematics
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Plant Systematics > Chair Plant Systematics - Univ.-Prof. Dr. Sigrid Liede-Schumann
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology
Result of work at the UBT: Yes
DDC Subjects: 500 Science
Date Deposited: 15 Jan 2018 14:06
Last Modified: 15 Jan 2018 14:06
URI: https://eref.uni-bayreuth.de/id/eprint/41334