Identification, occurrence and activity of quinazoline alkaloids in Peganum harmala
| Autor: | Vicente J. Arán, Tomás Herraiz, Antonio Salgado, Hugo Guillén |
|---|---|
| Přispěvatelé: | Consejo Superior de Investigaciones Científicas (España), Ministerio de Economía, Industria y Competitividad (España) |
| Rok vydání: | 2017 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Magnetic Resonance Spectroscopy Monoamine Oxidase Inhibitors Monoamine oxidase Drug Evaluation Preclinical Disaccharides Toxicology 030226 pharmacology & pharmacy 01 natural sciences Antioxidants Peganine (vasicine) Vasicine b-Carbolines 03 medical and health sciences chemistry.chemical_compound Alkaloids 0302 clinical medicine Antioxidant activity Peganum harmala Quinazoline Glycoside of peganine Chromatography High Pressure Liquid chemistry.chemical_classification Plants Medicinal ABTS Molecular Structure biology Traditional medicine 010401 analytical chemistry Glycoside General Medicine Ayahuasca biology.organism_classification 0104 chemical sciences Biochemistry chemistry Quinazolines Peganum Deoxypeganine Food Science |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 0278-6915 2015-6669 |
| DOI: | 10.1016/j.fct.2017.03.010 |
| Popis: | Peganum harmala L. is a medicinal plant from the Mediterranean region and Asia currently used for recreative psychoactive purposes (Ayahuasca analogue), and increasingly involved in toxic cases. Its psychopharmacological and toxicological properties are attributed to quinazoline and β-carboline alkaloids. In this work three major quinazoline alkaloids were isolated from P. harmala extracts and characterized as peganine (vasicine), deoxypeganine (deoxyvasicine) and a novel compound identified by HPLC-DAD-MS and NMR as peganine β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (peganine glycoside). Peganine appeared in flowers and leaves in high levels; high amounts of deoxypeganine and peganine were found in immature and green fruits whereas peganine and peganine glycoside accumulated in high amount in dry seeds reaching up to 1 and 3.9% (w/w), respectively. Roots and stems contained low amount of quinazolines. Seeds extracts containing both quinazoline and β-carboline alkaloids potently inhibited human monoamine oxidase (MAO)-A. However, quinazoline alkaloids did not contribute to MAO inhibition that was due to β-carbolines, suggesting that MAO-related psychoactive or toxic actions do not arise from quinazolines. Quinazoline alkaloids were poor radical scavengers in the ABTS assay whereas seed extracts had good activity. Quinazoline alkaloids are known to exert bronchodilator and abortifacient actions, and could contribute to such effects reported in P. harmala. The authors are grateful to MINECO (SAF2015-66690-R and SAF2015-68580-C2-2-R), and CSIC (Spain) (project 200470E658) for supporting this work. |
| Databáze: | OpenAIRE |
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