LC–NMR for Natural Product Analysis: A Journey from an Academic Curiosity to a Robust Analytical Tool

Sci ◽  
2021 ◽  
Vol 3 (1) ◽  
pp. 6
Author(s):  
Tesfay Gebretsadik ◽  
Wolfgang Linert ◽  
Madhu Thomas ◽  
Tarekegn Berhanu ◽  
Russell Frew
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Liquid Chromatography ◽  
Magnetic Resonance ◽  
Natural Product ◽  
Solid Phase ◽  
Structural Information ◽  
Analytical Tool ◽  
Molecular Formula ◽  
Product Analysis ◽  
Nuclear Magnetic

Liquid chromatography (LC)–nuclear magnetic resonance (NMR) combines the advantage of the outstanding separation power of liquid chromatography (LC) and the superior structural elucidating capability of nuclear magnetic resonance (NMR). NMR has proved that it is a standout detector for LC by providing maximum structural information about plant originated extracts, particularly on the isolating ability of isomeric (same molecular formula) and/or isobaric (same molecular weight) compounds as compared to other detectors. The present review provides an overview of the developmental trends and application of LC–NMR in natural product analysis. The different LC–NMR operational modes are described, and how technical improvements assist in establishing this powerful technique as an important analytical tool in the analysis of complex plant-derived compounds is also highlighted. On-flow, stop-flow and loop-storage modes, as well as the new offline mode LC–solid phase extraction (SPE)–NMR and capillary LC (capLC)–NMR configurations which avoid the ingestion of expensive deuterated solvents throughout the experiment, are mentioned. Utilization of cryogenic probe and microprobe technologies, which are the other important promising approaches for guaranteeing sensitivity, are also described. Concluding remarks and future outlooks are also discussed.

scholarly journals Degradation Characteristics of a Novel PAF Receptor Antagonist, SY0916, in Aqueous Solution

2019 ◽  
Vol 2019 ◽  
pp. 1-8
Author(s):  
Bo Jin ◽  
Yanan Wang ◽  
Tingting Zhang ◽  
Wanting Yin ◽  
Dongfeng Zhang ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Liquid Chromatography ◽  
Magnetic Resonance ◽  
Solid Phase ◽  
Degradation Products ◽  
Aqueous Media ◽  
Unsaturated Ketone ◽  
Phase I Clinical Trials ◽  
Degradation Behaviour ◽  
Nuclear Magnetic

SY0916 has been proven to be a potent treatment agent against rheumatoid arthritis in preclinical studies and has been shown to be safe in phase I clinical trials. However, SY0916 is unstable in water, which is frequently used in pharmaceutical development processes. The degradation behaviour and stability of SY0916 in aqueous solutions were investigated at different pH levels, periods of time, and temperatures. Two degradation products (DPs) were successfully separated and characterized by liquid chromatography coupled to high-resolution tandem mass spectrometry (LC-HRMS/MS), liquid chromatography coupled to nuclear magnetic resonance with solid phase extraction (LC-SPE-NMR), and nuclear magnetic resonance (NMR). SY0916 decomposed to its α,β-unsaturated ketone in protonic solvents, and the α,β-unsaturated ketone further transformed into its alcohol form through a conjugate addition reaction in aqueous media. The results of this study indicate that the pH of the buffer solutions should be maintained between 3.0 and 3.6 for maximum SY0916 stability. Factors that affect degradation should be carefully controlled to mitigate or avoid drug decay.

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