ArticleThe Journal of organic chemistry2013
HiFSA fingerprinting applied to isomers with near-identical NMR spectra: the silybin/isosilybin case.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
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Who cites it
48 citing papers in PubMed.
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- Comparative Assessment of Phytoconstituents, Antioxidant Activity and Chemical Analysis of Different Parts of Milk ThistleMolecules (Basel, Switzerland) · 2022Article
- Silymarin (milk thistle extract) as a therapeutic agent in gastrointestinal cancer.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2021Review
- Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners.International journal of molecular sciences · 2021Review
- NMR-Based Quantum Mechanical Analysis Builds Trust and Orthogonality in Structural Analysis: The Case of a Bisdesmosidic Triglycoside asJournal of natural products · 2021Article
- Quantum mechanical NMR full spin analysis in pharmaceutical identity testing and quality control.Journal of pharmaceutical and biomedical analysis · 2021Review
- Targeting Trimeric and Tetrameric Proanthocyanidins ofJournal of natural products · 2020Article
- Proanthocyanidin Dimers and Trimers fromJournal of natural products · 2019Article
- Formulation Strategies for Enhancing the Bioavailability of Silymarin: The State of the Art.Molecules (Basel, Switzerland) · 2019Review
- Quality Control of Therapeutic Peptides byThe Journal of organic chemistry · 2019Article
- The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.Natural product reports · 2019Review
- Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)-Chemistry, Bioavailability, and Metabolism.Molecules (Basel, Switzerland) · 2017Review
- Isolation and structural characterization of dihydrobenzofuran congeners of licochalcone A.Fitoterapia · 2017Article
- qNMR for profiling the production of fungal secondary metabolites.Magnetic resonance in chemistry : MRC · 2017Article
- Evolution of Quantitative Measures in NMR: Quantum Mechanical qHNMR Advances Chemical Standardization of a Red Clover (Trifolium pratense) Extract.Journal of natural products · 2017Article
- Computer-assistedMagnetic resonance in chemistry : MRC · 2017Article
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8 authors.
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Abstract
This study demonstrates how regio- and diastereo-isomers with near-identical NMR spectra can be distinguished and unambiguously assigned using quantum mechanical driven (1)H iterative Full Spin Analysis (HiFSA). The method is illustrated with four natural products, the flavonolignans silybin A, silybin B, isosilybin A, and isosilybin B, which exhibit extremely similar coupling patterns and chemical shift differences well below the commonly reported level of accuracy of 0.01 ppm. The HiFSA approach generated highly reproducible (1)H NMR fingerprints that enable distinction of all four isomers at (1)H frequencies from 300 to 900 MHz. Furthermore, it is demonstrated that the underlying numeric (1)H NMR profiles, combined with iterative computational analysis, allow parallel quantification of all four isomers, even in difficult to characterize reference materials and mixtures. The results shed new light on the historical challenges to the qualitative and quantitative analysis of these therapeutically relevant flavonolignans and open new opportunities to explore hidden diversity in the chemical space of organic molecules.
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