Molecular Network-Guided Alkaloid Profiling of Aerial Parts of Papaver nudicaule L. Using LC-HRMS.

Jae-Hyeon Oh,In Jin Ha,Kwangho Song,Min Young Lee,Seok-Geun Lee

doi:10.3390/molecules25112636

Abstract

Papaver nudicaule L. (Iceland poppy) is widely used for ornamental purposes. A previous study demonstrated the alleviation of lipopolysaccharide-induced inflammation mediated by P. nudicaule extract through nuclear factor-kappa B and signal transducer and activator of transcription 3 inactivation. As isoquinoline alkaloids are chemical markers and bioactive constituents of Papaver species, the present study investigated the alkaloid profile of aerial parts of five P. nudicaule cultivars with different flower colors and a P. rhoeas cropped for two years. A combination of liquid chromatography high-resolution mass spectrometry and molecular networking was used to cluster isoquinoline alkaloids in the species and highlight the possible metabolites. Aside from the 12 compounds, including rotundine, muramine, and allocryptopine, identified from Global Natural Products Social library and reported information, 46 structurally related metabolites were quantitatively investigated. Forty-two and 16 compounds were proposed for chemical profiles of P. nudicaule and P. rhoeas, respectively. Some species-specific metabolites showed similar fragmentation patterns. The alkaloid abundance of P. nudicaule differed depending on the flower color, and the possible chemical markers were proposed. These results show that molecular networking-guided dereplication allows investigation of unidentified metabolites. The derived chemical profile may facilitate evaluation of P. nudicaule quality for pharmacological applications.

Highlights

IntroductionPlants in the Papaver L. genus from Papaveraceae (commonly known as poppy) family have been used for traditional medicinal practices and ornamental purposes for a long time
Plants in the Papaver L. genus from Papaveraceae family have been used for traditional medicinal practices and ornamental purposes for a long time
To organize the compound candidates for the alkaloid profiling of P. nudicaule and P. rhoeas, the liquid chromatography (LC)-mass spectrometry (MS)/MS data from 12 extracts was submitted to molecular networking through the Global Natural Products Social (GNPS) web platform

Summary

Introduction

Plants in the Papaver L. genus from Papaveraceae (commonly known as poppy) family have been used for traditional medicinal practices and ornamental purposes for a long time. (Iceland poppy) are widely used for ornamentation owing to their multicolored flowers. Nudicaulins, which are flavonoid-derived indole alkaloids, along with pelargonidin, kaempferol, and gossypetin glycosides, are responsible for the white, red, orange, and yellow colored petals of different P. nudicaule cultivars [1,2]. P. nudicaule belongs to the Papaveraceae family, and is an annual herbaceous species. This plant can produce various alkaloids, isoquinoline alkaloids (IAs) [3]. IAs from Papaver species possess potent pharmacological properties, including narcotic analgesic, antimicrobial, muscle relaxant, cough suppressant, and anticancer

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