التفاصيل البيبلوغرافية
العنوان:
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)
المؤلفون:
Dale R. Gardner , Steven M. Colegate , Ottmar W. Fischer , Michael Boppré , Sigrid Liede-Schumann , Joseph M. Betz
المصدر:
Phytochemical Analysis . 27:257-276
بيانات النشر:
Wiley, 2016.
سنة النشر:
2016
مصطلحات موضوعية:
0106 biological sciences , Magnetic Resonance Spectroscopy , Stereochemistry , Plant Science , 010603 evolutionary biology , 01 natural sciences , Biochemistry , High-performance liquid chromatography , Mass Spectrometry , Analytical Chemistry , chemistry.chemical_compound , Alkaloids , Drug Discovery , Pyrroles , Cation Exchange Resins , Medicinal plants , Chromatography, High Pressure Liquid , Caudata , Plants, Medicinal , Apocynaceae , biology , Alkaloid , Solid Phase Extraction , Esters , General Medicine , biology.organism_classification , Apocynoideae , Complementary and alternative medicine , chemistry , Pyrrolizidine , Retronecine , Molecular Medicine , 010606 plant biology & botany , Food Science
الوصف:
INTRODUCTION: Within the Apocynoideae (Apocynaceae) pro‐toxic dehydropyrrolizidine alkaloids have been reported only in Echiteae. 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 and identify their structures. METHODS: Methanol extracts of air‐dried roots, stems and leaves of non‐flowering plants were analysed using HPLC‐ESI(+)MS and MS/MS or collision‐induced dissociation MS in low and/or high resolution modes. Pyrrolizidine alkaloids were tentatively identified based on the mass spectrometry data. Solid phase extraction combined with semi‐preparative HPLC were used to isolate major alkaloids. 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 of Amphineurion marginatum. Pyrrolizidine alkaloids were detected in root and leaf material of Alafia cf. caudata at 0.34 and 0.01% 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 pose potential health risks to consumers. Dehydropyrrolizidine alkaloids are evidently more widespread in Apocynoideae than previously assumed, and it would seem rewarding to study other members of this family for the presence of pyrrolizidines, dehydropyrrolizidines and dihydropyrrolizines. Copyright © 2016 John Wiley & Sons, Ltd.
تدمد:
0958-0344
DOI:
10.1002/pca.2624
URL الوصول:
https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c28c5b64a4a691add6a29249aa8287f https://doi.org/10.1002/pca.2624
Rights:
CLOSED
رقم الانضمام:
edsair.doi.dedup.....7c28c5b64a4a691add6a29249aa8287f
قاعدة البيانات:
OpenAIRE