Structure elucidation of degradation products of Z-ligustilide by UPLC-QTOF-MS and NMR spectroscopy / 药学学报
Acta Pharmaceutica Sinica
;
(12): 911-916, 2013.
Article
in English
| WPRIM
| ID: wpr-259530
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.
Full text:
Available
Index:
WPRIM (Western Pacific)
Main subject:
Oxidation-Reduction
/
Plants, Medicinal
/
Benzofurans
/
4-Butyrolactone
/
Magnetic Resonance Spectroscopy
/
Chemistry
/
Chromatography, High Pressure Liquid
/
Plant Roots
/
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
/
Ligusticum
Language:
English
Journal:
Acta Pharmaceutica Sinica
Year:
2013
Type:
Article
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