ABSTRACT
Z-Ligustilide, a major phthalide isolated from a widely used traditional Chinese medicine Ligusticum chuanxiong, possesses various pharmacological activities including neuroprotective, anti-inflammatory, antiproliferative and vasorelaxing effects. However, it is unstable and inclined to degrade in natural conditions, which limits its study and application greatly. In this study, degradation behavior of Z-ligustilide and its degradation products stored at room temperature under direct sunlight were investigated and structure elucidated by HPLC-UV, UPLC-QTOF-MS and NMR. Z-ligustilide degradation and total five degradation products were generated and detected. Two degradation products were unequivocally identified as senkyunolide I and senkyunolide H by comparison with reference compounds. Another two degradation products were further isolated by semi-preparative HPLC and structure elucidated as (E)-6, 7-trans-dihydroxyligustilide and (Z)-6, 7-epoxyligustilide by 1H and 13C NMR, respectively. The degradation pathways of Z-ligustilide were finally proposed. Oxidation, hydrolysis and isomerization are the major degradation reactions.
Subject(s)
4-Butyrolactone , Metabolism , Benzofurans , Metabolism , Chromatography, High Pressure Liquid , Hydrolysis , Ligusticum , Chemistry , Magnetic Resonance Spectroscopy , Metabolic Networks and Pathways , Oxidation-Reduction , Plant Roots , Chemistry , Plants, Medicinal , Chemistry , Spectrometry, Mass, Matrix-Assisted Laser Desorption-IonizationABSTRACT
<p><b>OBJECTIVE</b>To analyze and identify the chemical constituents in rat brain tissues after oral administration of Chuanxiong Rhizoma extracts.</p><p><b>METHOD</b>The dosed and blank rat brain tissues were analyzed by UPLC-Q-TOF-MS. Different peaks were observed in total ion chromatograms and then identified according to their retention time, accurate mass weight, MS and MS/MS data.</p><p><b>RESULT</b>After oral administration of Chuanxiong Rhizoma extracts, 3 compounds were absorbed into rat brain tissues through BBB. They were identified as senkyunolide I, senkyunolide A and ligustilide.</p><p><b>CONCLUSION</b>The study is helpful for interpreting effective substance of Ligusticum chuanxiong.</p>
Subject(s)
Animals , Female , Humans , Rats , Brain , Metabolism , Chromatography, High Pressure Liquid , Methods , Drugs, Chinese Herbal , Pharmacokinetics , Ligusticum , Chemistry , Mass Spectrometry , Methods , Rats, Sprague-Dawley , Rhizome , ChemistryABSTRACT
Ligustilide is contained highly or around 1% in such umbelliferous plants as Angelica sinensis and Ligusticum chuanxiong, is one of main bioactive constituents. It shows many pharmacological activities related to their efficacy. At present, ligustilide has attracted extensive attention and more and more studies have been reported, indicating that it is a promising compound. This essay summarizes the progress of pharmacological effects of ligustilide on neuroprotection, vasodilatation, anti-caner and anti-tumor, analgesia and anti-inflammation, and pharmacokinetics including absorption, distribution, metabolism and excretion, providing basis for further studies and development of ligustilide.