药学学报, 2013, 48(6): 911-916
引用本文:
左爱华, 程孟春, 卓荣杰, 王 莉, 肖红斌. Z-藁本内酯降解产物的UPCL-QTOF-MS和NMR结构鉴定[J]. 药学学报, 2013, 48(6): 911-916.
ZUO Ai-hua, CHENG Meng-chun, ZHUO Rong-jie, WANG Li, XIAO Hong-bin. Structure elucidation of degradation products of Z-ligustilide by UPLC-QTOF-MS and NMR spectroscopy[J]. Acta Pharmaceutica Sinica, 2013, 48(6): 911-916.

Z-藁本内酯降解产物的UPCL-QTOF-MS和NMR结构鉴定
左爱华, 程孟春, 卓荣杰, 王 莉, 肖红斌*
(中国科学院大连化学物理研究所分离分析重点实验室, 辽宁 大连 116023)
摘要:

Z-藁本内酯是中药川芎中主要的苯酞类化合物, 具有神经保护、抗炎、抗增值及扩张血管等多种药理作用。但Z-藁本内酯在自然条件不稳定且易于降解, 限制其研究和应用。本文采用HPLC-UVUPLC-QTOF-MSNMRZ-藁本内酯室温自然光照下的降解行为及降解产物进行考察和鉴定, Z-藁本内酯完全降解后生成5个降解产物, 2个降解产物通过与对照品对比确定为洋川芎内酯I和洋川芎内酯H, 2个降解产物采用半制备HPLC分离后进行1H13C NMR解析, 确定其结构为 (E)-6, 7-反式-双羟基藁本内酯和 (Z)-6, 7-环氧藁本内酯。最后推测了Z-藁本内酯的降解途径, 氧化、水解和异构化是主要的降解反应。

关键词:   
Structure elucidation of degradation products of Z-ligustilide by UPLC-QTOF-MS and NMR spectroscopy
Abstract:

Z-Ligustilide, a major phthalide isolated from a widely used traditional Chinese medicine Ligusticum chuanxiong, possesses various pharmacological activities including neuroprotective, anti-inflammatory, anti- proliferative 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.

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