Dereplication Study on Glaucium Aleppicum Boiss. in Jordan

Abstract

The secondary metabolite constituents of Glaucium aleppicum Boiss. et Hausskn. ex Boiass. (Papaveraceae) were investigated using an in-house developed Ultra Performance Liquid Chromatography-Photodiode Array-High Resolution Tandem Mass Spectrometry (UPLC-PDA-HRMS-MS/MS) method. In this study the powerful resolution and short analysis time afforded by UPLC coupled to the outstanding mass accuracy of an Orbitrap mass spectrometer was used to develop a rapid and effective dereplication method to identify secondary metabolite constituents of G. aleppicum in crude extracts. In addition, HCD MS/MS and UV (photodiode array) spectra were used as an integral part of the strategy. This methodology was applied on a small amount of extract (~ 1 mg) of G. aleppicum to dereplicate twelve compounds. Five of which have been isolated previously from G. aleppicum: allocryptopine, protopine, corydine, isocorydine, and norchelidonine. Seven were new to the species, these include: dehydroglaucine, norisocorydine, chelerythrine, norsanguinarine, dihydrochelerythrine, corytuberine, and fumaflorine methyl ester. In addition to one more compound that was unidentified and thus considered new.

Exploring Chemical Composition, Antioxidant, Enzyme Inhibitory and Cytotoxic Properties of Glaucium acutidentatum Hausskn. & Bornm. from Turkey Flora: A Novel Source of Bioactive Agents to Design Functional Applications

“…Two peaks, 28 and 29, with precursor ions at m / z 354.1237 and 370.1624, respectively, had the same basic skeleton of protopine alkaloid. By comparing their fragmentation behavior with those reported by Barakat, et al [ 57 ], compound 28 was unambiguously identified as protopine, while compound 29 as α-allocryptopine, identified for the first time in G. acutidentatum . Diagnostic ions with m / z values of 189 and 188, resulting from B-ring cleavage and/or RDA fragmentation, observed in the MS/MS spectra of both compounds, confirmed our assumption [ 50 ].…”

“…Compound 26 presented a similar fragmentation pattern but differed in the intensity of the generated product ions. A comparison of the product ions with the highest intensity at m/z 311.1266 for compound 23 and at m/z 279.0994 for compound 26 allowed their identification as isocorydine and corydine, respectively, reported in G. aleppicum by Barakat et al (2016). Two compounds, 27 and 31, afforded precursor ions at m/z 372 and a molecular formula of C21H25NO5, suggesting the glaucine structure with an additional OH group.…”