Abstract
Many natural product chemists are working to identify a wide variety of novel secondary metabolites from natural materials and are eager to avoid repeatedly discovering known compounds. Here, we developed liquid chromatography/mass spectrometry (LC/MS) data-processing protocols for assessing high-throughput spectral data from natural sources and scoring the novelty of unknown metabolites from natural products. This approach automatically produces representative MS spectra (RMSs) corresponding to single secondary metabolites in natural sources. In this study, we used the RMSs of Agrimonia pilosa roots and aerial parts as models to reveal the structural similarities of their secondary metabolites and identify novel compounds, as well as isolation of three types of nine new compounds including three pilosanidin- and four pilosanol-type molecules and two 3-hydroxy-3-methylglutaryl (HMG)-conjugated chromones. Furthermore, we devised a new scoring system, the Fresh Compound Index (FCI), which grades the novelty of single secondary metabolites from a natural material using an in-house database constructed from 466 representative medicinal plants from East Asian countries. We expect that the FCIs of RMSs in a sample will help natural product chemists to discover other compounds of interest with similar chemical scaffolds or novel compounds and will provide insights relevant to the structural diversity and novelty of secondary metabolites in natural products.
Highlights
Many natural product chemists are working to identify a wide variety of novel secondary metabolites from natural materials and are eager to avoid repeatedly discovering known compounds
We introduced a new scoring system, the Fresh Compound Index (FCI), which evaluates the dissimilarity of the representative mass spectrometry (MS) spectra (RMSs) in a sample against 65,322 reference RMSs obtained from 466 medicinal plants that have been added to our in-house database
The RMSs are tentatively considered to be derived from single metabolites that are well separated on the ultra-performance liquid chromatography (UPLC) system, and the RMSs are used to investigate the structural characteristics of the secondary metabolites in the extracts of natural materials
Summary
Many natural product chemists are working to identify a wide variety of novel secondary metabolites from natural materials and are eager to avoid repeatedly discovering known compounds. We developed liquid chromatography/mass spectrometry (LC/MS) data-processing protocols for assessing high-throughput spectral data from natural sources and scoring the novelty of unknown metabolites from natural products. This approach automatically produces representative MS spectra (RMSs) corresponding to single secondary metabolites in natural sources. We introduced a new scoring system, the Fresh Compound Index (FCI), which evaluates the dissimilarity of the RMSs in a sample against 65,322 reference RMSs obtained from 466 medicinal plants that have been added to our in-house database This scoring system helps natural product researchers discover unusual secondary metabolites that can contribute to expanding the chemical diversity of natural products
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