Dynamic Nature of the Ligustilide Complex
| Autor: | David C. Lankin, Matthew Main, Samuel M. Pro, Birgit U. Jaki, Shao-Nong Chen, Guido F. Pauli, Andreas Schinkovitz |
|---|---|
| Přispěvatelé: | Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), University of Illinois at Chicago, University of Illinois [Springfield] |
| Jazyk: | angličtina |
| Rok vydání: | 2008 |
| Předmět: |
Angelica sinensis
[SDV]Life Sciences [q-bio] Pharmaceutical Science 01 natural sciences Plant Roots Article Analytical Chemistry Phthalide chemistry.chemical_compound Countercurrent chromatography 4-Butyrolactone Drug Discovery Sample preparation Nuclear Magnetic Resonance Biomolecular Pharmacology chemistry.chemical_classification Chromatography Plants Medicinal biology Molecular Structure 010405 organic chemistry 010401 analytical chemistry Organic Chemistry Supercritical fluid extraction Stereoisomerism biology.organism_classification Supercritical fluid 0104 chemical sciences Fluid extract Complementary and alternative medicine chemistry Phthalic Anhydrides Molecular Medicine Lactone |
| Zdroj: | Journal of Natural Products Journal of Natural Products, American Chemical Society, 2008, 71 (9), pp.1604-11. ⟨10.1021/np800137n⟩ |
| ISSN: | 0163-3864 1520-6025 |
| DOI: | 10.1021/np800137n⟩ |
| Popis: | International audience; Monomeric phthalides such asZ-ligustilide (1) andZ-butylidenephthalide (2) are major constituents of medicinal plants of the Apiaceae family. While1has been associated with a variety of observed biological effects, it is also known for its instability and rapid chemical degradation. For the purpose of isolating pure1and2, a gentle and rapid two-step countercurrent isolation procedure was developed. From a supercritical CO2fluid extract ofAngelica sinensisroots, the phthalides were isolated with high GC-MS purities of 99.4% for1and 98.9% for2and consistently lower qHNMR purities of 98.1% and 96.4%, respectively. Taking advantage of molarity-based qHNMR methodology, a time-resolved study of the dynamic changes and residual complexity of pure1was conducted. GC-MS and (qH)NMR analysis of artificially degraded1provided evidence for the phthalide degradation pathways and optimized storing conditions. Parallel qHNMR analysis led to the recognition of variations in time- and process-dependent sample purity and has impact on the overall assessment of time-dependent changes in complex natural products systems. The study underscores the importance of independent quantitative monitoring as a prerequisite for the biological evaluation of labile natural products such as monomeric phthalides. |
| Databáze: | OpenAIRE |
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