温经汤多成分挥发油β-环糊精及其衍生物包合物的制备、表征及包合行为研究

Study on Preparation, Characterization and Inclusion Behavior of β-Cyclodextrin and Its Derivatives Inclusion Complex of Wenjing Decoction Multi-Component Volatile Oil

    摘要
  • 摘要:
    目的 制备温经汤挥发油环糊精包合物以提高其稳定性，并表征包合物的形成；对比不同环糊精对温经汤挥发油中主要成分桂皮醛、丹皮酚、藁本内酯包合行为差异，探究不同环糊精对温经汤挥发油中多成分包合的影响。
    方法 采用超声法制备温经汤挥发油β-CD及其5种衍生物包合物，HPLC法测定各成分包合率。采用TGA、FT-IR表征包合物的形成。通过相溶解度试验、分子对接研究其包合行为及影响因素。
    结果 成功制备温经汤挥发油β-CD及其衍生物的包合物，且TGA结果显示温经汤挥发油经环糊精包合后热稳定性提升，FT-IR结果显示挥发油中部分成分与环糊精通过氢键等非共价键结合。相溶解度试验结果表明，温经汤挥发油中3种主要成分均以1 ∶ n(n≥1)的摩尔比与β-CD结合，而与β-CD衍生物结合以1 ∶ 1的摩尔比结合。分子对接结果显示，桂皮醛、丹皮酚的苯环及藁本内酯的内酯环均深入环糊精空腔形成包合物。β-CD及其衍生物对温经汤挥发油中各成分的包合率大小均为DM-β-CD＞HP-β-CD＞β-CD＞HE-β-CD＞SBE-β-CD＞CM-β-CD，与相溶解度试验和分子对接得出的亲和力大小一致；而3种成分与β-CD及其衍生物的包合率大小为桂皮醛＞丹皮酚＞藁本内酯，与挥发油中各成分浓度大小一致，但与相溶解度试验和分子对接得出亲和力大小顺序相反。
    结论 β-CD及其衍生物均能成功包合温经汤挥发油，挥发油中成分与环糊精以氢键等非共价键力结合形成包合物，增加了挥发油的稳定性。不同环糊精包合多成分挥发油时对各成分的包合率与挥发性成分和环糊精之间的亲和力以及挥发性成分浓度有关，为温经汤挥发油包合物中主要成分与基准样品的一致性研究提供思路。

     

    Abstract:
    OBJECTIVE To prepare the volatile oil cyclodextrin inclusion compound of Wenjing Decoction to improve its stability and characterize its formation; to compare the inclusion behavior of cinnamaldehyde, paeonol and ligustilide in volatile oil of Wenjing Decoction with different cyclodextrins; and to study the effect of different cyclodextrins on the inclusion of multiple components in the volatile oil of Wenjing Decoction.
    METHODS The inclusion compounds of volatile oil β-CD and its 5 derivatives in Wenjing Decoction were prepared by ultrasonic method, and the inclusion rate of each component was determined by HPLC. TGA and FT-IR were used to characterize the formation of the inclusion complex. The inclusion behavior and influencing factors were studied by phase solubility test and molecular docking.
    RESULTS The inclusion compounds of volatile oil β-CD and its derivatives in Wenjing Decoction were successfully prepared. TGA results showed that the thermal stability of volatile oil in Wenjing Decoction was improved after inclusion by cyclodextrin. FT-IR results showed that some components of the volatile oil were bonded to cyclodextrin through non-covalent bonds such as hydrogen bonds. The results of phase solubility test showed that the three main components in the volatile oil of Wenjing Decoction were combined with β-CD in the molar ratio of 1 ∶ n (n≥1), and with β-CD derivatives in the molar ratio of 1 ∶ 1. The results of molecular docking showed that the benzene rings of cinnamaldehyde and paeonol, and lactone rings of ligustilide penetrated into the cyclodextrin cavity to form clathrates. The inclusion rates of β-CD and its derivatives for each component in the volatile oil of Wenjing Decoction were DM-β-CD > HP-β-CD > β-CD > HE-β-CD > SBE-β-CD > CM-β-CD, which were consistent with the affinity of phase solubility test and molecular docking. The inclusion rates of the three components with β-CD and its derivatives were cinnamaldehyde > paeonol > ligustilide, which was consistent with the concentration of each component in the volatile oil, but the affinity order was opposite to that obtained by phase solubility test and molecular docking.
    CONCLUSION β-CD and its derivatives can successfully incorporate the volatile oil of the decoction. The components of the volatile oil and cyclodextrin are combined to form the inclusion compound by hydrogen bonding and other non-covalent bonding forces, which increases the stability of the volatile oil. The inclusion rate of volatile oil with different cyclodextrins is related to the affinity between volatile components and cyclodextrins and the concentration of volatile components, which provides a way to ensure the consistency between the main component of volatile oil inclusion compound in Wenjing Decoction and the reference sample.

     

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