Non-targeted analysis of vulgarisins by using collisional dissociation mass spectrometry for the discovery of analogues from Prunella vulgaris

Vulgarisins are members of diterpenoids with rare 5/6/4/5 ring skeleton from Prunella vulgaris Linn. ( P . vulgaris ). Their molecular scaffolds comprise different hydroxylation and degree of esterification. Vulgarisins have attracted many attentions in the fields of food and medicine for their pote...

Full description

Saved in:
Bibliographic Details
Published in:Analytical and bioanalytical chemistry 2021-11, Vol.413 (26), p.6513-6521
Main Authors: Ma, Fengwei, Lou, Huayong, Ge, Yonghui, Li, Jinyu, Chen, Chao, Xu, Su, Tang, Lei, Pan, Weidong
Format: Article
Language:English
Subjects:
Analytical Chemistry
Biochemistry
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Chromatography, High Pressure Liquid
Diagnostic systems
Diterpenes
Energy of dissociation
Esterification
Food Science
Fragmentation
High performance liquid chromatography
Hydroxylation
Ionization
Ions
Laboratory Medicine
Liquid chromatography
Mass spectrometry
Mass spectroscopy
Monitoring/Environmental Analysis
Natural products
NMR
NMR spectroscopy
Nuclear magnetic resonance
Plant Extracts - chemistry
Prunella - chemistry
Prunella vulgaris
Research Paper
Scaffolds
Scientific imaging
Sodium
Spectrometry, Mass, Electrospray Ionization
Tandem Mass Spectrometry
Two dimensional analysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Vulgarisins are members of diterpenoids with rare 5/6/4/5 ring skeleton from Prunella vulgaris Linn. ( P . vulgaris ). Their molecular scaffolds comprise different hydroxylation and degree of esterification. Vulgarisins have attracted many attentions in the fields of food and medicine for their potent bioactivities. Firstly, four reference compounds were analyzed by higher-energy collisional dissociation mass spectrometry (HCD MS/MS) and the fragmentation patterns for molecular scaffold were summarized. And then, a high-performance liquid chromatography/electrospray ionization/high-resolution mass spectrometry (HPLC-ESI-HR-MS) method was adopted to investigate the P . vulgaris extracts. Finally, the proposed analysis results were successfully applied to facilitate the discovery of the vulgarisins analogues from P . vulgaris . For the four reference compounds, the sodium adduct was the predominate ion in full scan. A specific fragmentation pathway of [M+Na] + ions leads to produce diagnostic ions of vulgarisins at m / z 325 under HCD, which was formed through consecutive-side chains lost. Twenty-three diterpenoids, including 18 vulgarisins analogues, were identified or tentatively characterized in the botanical extracts of P . vulgaris based on their elemental constituents and characteristic fragment ion profiles. Two new vulgarisins analogues in the plant were isolated and their structures were illustrated based on extensive spectroscopic analysis using 1 D and 2 D nuclear magnetic resonance (NMR) spectroscopy. The HCD MS/MS method, including the profiles of the diagnostic ions induced by characteristic fragmentation, is an effective technique for the discovery of vulgarisins analogues in P . vulgaris . The expected fragmentation pattern knowledge will also facilitate the analysis of other natural products. Graphical abstract
ISSN:1618-2642
1618-2650
DOI:10.1007/s00216-021-03615-x