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ARS Home » Pacific West Area » Logan, Utah » Poisonous Plant Research » Research » Publications at this Location » Publication #330155
Title: 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 Apoc

Author
item COLEGATE, STEVEN - Utah State University
item Gardner, Dale
item BETZ, JOSEPH - National Institutes Of Health (NIH)
item FISCHER, OTTMAR - Albert University Of Freiburg
item LIEDE-SCHUMANN, SIGRID - University Of Bayreuth
item BOPPRE, MICHAEL - Albert University Of Freiburg

Submitted to: Phytochemical Analysis
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/7/2016
Publication Date: 9/1/2016
Publication URL: http://handle.nal.usda.gov/10113/5454517
Citation: Colegate, S.M., Gardner, D.R., Betz, J.M., Fischer, O.W., Liede-Schumann, S., Boppre, M. 2016. 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). Phytochemical Analysis. 27(5):257-276.

Interpretive Summary: The attraction of pharmacophagous insects indicated the presence of toxic dehydropyrrolizidine alkaloids in two traditionally used medicinal plants in Africa (Alafia cf. caudata and Amphineurion marginatum). Subsequently, the analysis of collected plant material by solvent extraction and liquid chromatography-mass spectrometry identified a number of different toxic alkaloids as a class known as dehydropyrrolizidine in both plant samples. In addition to previously known toxic alkaloids several new compounds were identified and most notably was the identification of two10-membered macrocyclic dehydropyrrolizidine alkaloid diesters, previously unprecedented in reports from natural sources, were isolated from Amphineurion marginatum. Since both plants are used as traditional medicine this suggests potential health risks to consumers.

Technical Abstract: The attraction of pyrrolizidine alkaloid-pharmacophagous insects indicated the presence of pro-toxic dehydropyrrolizidine alkaloids in Alafia cf. caudata Stapf (Nerieae: Alafinae) and Amphineurion marginatum (Roxb.) D.J. Middleton (Apocyneae: Amphineuriinae). Subsequently, monoesters of retronecine with senecioic, hydroxysenecioic or syringic acids were identified in Alafia cf. caudata, and 10-membered macrocyclic dehydropyrrolizidine alkaloid diesters, previously unprecedented in reports from natural sources, were isolated from Amphineurion marginatum. Since both plants are used as traditional medicine this suggests potential health risks to consumers.