Dynamic Nature of the Ligustilide Complex

TitreDynamic Nature of the Ligustilide Complex
Type de publicationArticle de revue
AuteurSchinkovitz, Andreas , Pro, Samuel M, Main, Matthew, Chen, Shaonong, Jaki, Birgit U, Lankin, David C, Pauli, Guido
EditeurAmerican Chemical Society
TypeArticle scientifique dans une revue à comité de lecture
Année2008
LangueAnglais
DateJan-09-2008
Numéro9
Pagination1604-11
Volume71
Titre de la revueJournal of Natural Products
ISSN0163-3864
Résumé en anglais

Monomeric phthalides such as Z-ligustilide (1) and Z-butylidenephthalide (2) are major constituents of medicinal plants of the Apiaceae family. While 1 has 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 pure 1 and 2, a gentle and rapid two-step countercurrent isolation procedure was developed. From a supercritical CO2 fluid extract ofAngelica sinensis roots, the phthalides were isolated with high GC-MS purities of 99.4% for 1and 98.9% for 2 and 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 pure 1 was conducted. GC-MS and (qH)NMR analysis of artificially degraded 1 provided 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.

URL de la noticehttp://okina.univ-angers.fr/publications/ua10584
DOI10.1021/np800137n
Lien vers le document

http://pubs.acs.org/doi/abs/10.1021/np800137n

Titre abrégéJ. Nat. Prod.