plantMASST - Community-driven chemotaxonomic digitization of plants

N-acyl lipids are important mediators of several biological processes including immune function and stress response. To enhance the detection of N-acyl lipids with untargeted mass spectrometry-based metabolomics, we created a reference spectral library retrieving N-acyl lipid patterns from 2,700 public datasets, identifying 851 N-acyl lipids that were detected 356,542 times. 777 are not documented in lipid structural databases, with 18% of these derived from short-chain fatty acids and found in the digestive tract and other organs. Their levels varied with diet, microbial colonization, and in people living with diabetes. We used the library to link microbial N-acyl lipids, including histamine and polyamine conjugates, to HIV status and cognitive impairment. This resource will enhance the annotation of these compounds in future studies to further the understanding of their roles in health and disease and highlight the value of large-scale untargeted metabolomics data for metabolite discovery.

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Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

Damiani,

Smith,

Hebra

et al. 2024

Preprint

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SummaryThe Piperaceae plant family is known for its special phytochemistry and is widely recognized as a rich source of bioactive natural products. Piperaceae plants, especially from thePipergenus, have been extensively investigated in the past decades; yet, new alkaloids are still regularly reported from this genus. Here, we investigated the alkaloid diversity ofPiper fimbriulatumusing a metabolomics workflow that combines untargeted LC-MS/MS analysis with a range of recently developed computational tools. In particular, we leverage open libraries of MS/MS spectra and metabolomics data repositories for metabolite annotation and to direct isolation efforts towards structurally-novel compounds (i.e., dereplication). We identified several alkaloids belonging to 5 different classes and isolated one novelseco- benzylisoquinoline alkaloid with a linear quaternary amine nitrogen. Notably, many of the identified compounds were never reported in Piperaceae plants. Our findings expand the known alkaloid diversity of the Piperaceae family, and demonstrate the potential of revisiting well-studied plant families using state-of-the-art computational metabolomics workflows to uncover previously overlooked chemodiversity. Finally, we contextualized our findings in a broader evolutionary framework by mapping literature reports for the identified alkaloid scaffolds onto the angiosperm tree of life, which highlighted the remarkable alkaloid diversity in thePipergenus.Significance StatementWe leveraged untargeted metabolomics with a range of recently developed computational tools to uncover a remarkable diversity of alkaloid scaffolds inPiper fimbriulatum. Our findings demonstrate the potential of revisiting well-studied plant families using state-of-the-art computational metabolomics workflows to uncover previously overlooked chemodiversity.

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plantMASST - Community-driven chemotaxonomic digitization of plants

Cited by 3 publications

References 53 publications

Effective data visualization strategies in untargeted metabolomics

Effective data visualization strategies in untargeted metabolomics

The microbiome diversifiesN-acyl lipid pools - including short-chain fatty acid-derived compounds

Remarkable diversity of alkaloid scaffolds inPiper fimbriulatum

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