近红外光谱和混料实验设计研究β-环糊精差异化包封挥发油成分: 以包合α-蒎烯、月桂烯和3-蒈烯为例

doi:10.5246/jcps.2021.06.041

中国药学(英文版) ›› 2021, Vol. 30 ›› Issue (6): 524-537.DOI: 10.5246/jcps.2021.06.041

近红外光谱和混料实验设计研究β-环糊精差异化包封挥发油成分: 以包合α-蒎烯、月桂烯和3-蒈烯为例

李哲¹^,², 丁媛¹, 黄浩³, 王可馨¹, 吴嘉仪¹, 朱琳², 廖正根², 明良山¹^,²^,³^,^*()

1. 江西中医药大学高等研究院中医基础理论分化发展研究中心, 江西南昌 330004
2. 江西中医药大学现代中药制剂教育部重点实验室, 江西南昌 330004
3. 赣南医学院药学院国家中药现代化工程技术研究中心-客家中医药资源研究分中心, 江西赣州 341000

收稿日期:2020-06-22 修回日期:2020-10-15 接受日期:2021-12-01 出版日期:2021-06-29 发布日期:2021-06-29
通讯作者: 明良山
作者简介:
+ Tel.: +86-791-87142859, E-mail: jazmaster@163.com, 20201005@jxutcm.edu.cn
基金资助:
National Natural Science Foundation of China (Grant No. 82003953), China Postdoctoral Science Foundation (Grant No. 2019M662278), Science and Technology Project of Education Department of Jiangxi Province (Grant No. GJJ190688, GJJ201252), Postdoctoral Science Foundation of Jiangxi Province (Grant No. 2019KY42), Key Scientific Research Foundation of Jiangxi University of Traditional Chinese Medicine (Grant No. 2004/538200010402).

Study of β-cyclodextrin differential encapsulation of essential oil components by using mixture design and NIR: Encapsulation of α-pinene, myrcene, and 3-carene as an example

Zhe Li¹^,², Yuan Ding¹, Hao Huang³, Kexin Wang¹, Jiayi Wu¹, Lin Zhu², Zhenggen Liao², Liangshan Ming¹^,²^,³^,^*()

1 Institute for Advanced Study, Research Center for Differentiation and Development of TCM Basic Theory, Jiangxi University of?Chinese Medicine, Nanchang 330004, China
2 Key Laboratory of Preparation of Modern TCM, Ministry of Education, Jiangxi University of?Chinese Medicine, Nanchang 330004, China
3 National Engineering Research Center for Modernization of TCM-Hakka Medical Resources Branch, School of Pharmacy, Gannan Medical University, Jiangxi, Ganzhou 341000, China

Received:2020-06-22 Revised:2020-10-15 Accepted:2021-12-01 Online:2021-06-29 Published:2021-06-29
Contact: Liangshan Ming

摘要/Abstract

摘要：

环糊精包封挥发油形成包合物是提高其稳定性和生物利用度的有效策略。本研究为了实现对多组分成分的包合过程进一步的理解, 研究采用相同分子量的客体分子α-蒎烯、月桂烯和3-蒈烯与β-环糊精通过冷冻干燥形成包合物。研究设计了一个含有28次试验的单纯型格子混料实验, 并通过统计学分析包合行为, 由近红外光谱定量的模型。此外, 利用分子对接技术获得包合物的最优构象并阐明包合行为。结果表明客体分子间的空间结构和占比是影响包封效率的关键因素；二阶导数法预处理法构建近红外模型, 从而实现客体分子在包合物中的快速、无损的含量检测。总之, β-环糊精包封客体分子具有差异化, 近红外光谱可以作为一种快速和无损的检测方法用于定量分析包合物的含量。

关键词: 包合物, 环糊精, 差异包合, 近红外光谱, 分子对接技术

Abstract:

The encapsulation of essential oil components in cyclodextrins (CDs) to form inclusion complexes (ICs) is an effective strategy for improving their stability and bioaccessibility. The aim of the present study was to obtain a deeper understanding of the encapsulation behavior of multi-components in β-CD. Guest molecules of α-pinene, myrcene, and 3-carene, having the same molecular weight, formed ICs with β-CD by a freeze-drying method. A simplex lattice mixture design with 28 experiments was carried out. Statistical analysis was applied to analyze the encapsulation behavior of guest components, and quantitative models of guest components in ICs were constructed by coupling with near-infrared (NIR) spectroscopy and chemometrics analysis. Besides, the molecular docking technique was used to obtain the optimal conformation and explain the binding behavior of inclusion. The results suggested that the spatial structure and ratio of guest molecules were the key factors affecting the encapsulation effect. A non-destructive and rapid NIR analytical model for the guest component in ICs could be obtained by second derivative (2nd der) pretreatment. Collectively, the encapsulation of guest components in β-CD was differentiated, and NIR could be used as a rapid and non-destructive tool for quantitative analysis of ICs.

Key words: Inclusion complexes, Cyclodextrin, Differential encapsulation, NIR spectroscopy, Molecular docking

Supporting:

李哲, 丁媛, 黄浩, 王可馨, 吴嘉仪, 朱琳, 廖正根, 明良山. 近红外光谱和混料实验设计研究β-环糊精差异化包封挥发油成分: 以包合α-蒎烯、月桂烯和3-蒈烯为例[J]. 中国药学(英文版), 2021, 30(6): 524-537.

Zhe Li, Yuan Ding, Hao Huang, Kexin Wang, Jiayi Wu, Lin Zhu, Zhenggen Liao, Liangshan Ming. Study of β-cyclodextrin differential encapsulation of essential oil components by using mixture design and NIR: Encapsulation of α-pinene, myrcene, and 3-carene as an example[J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(6): 524-537.

图/表 9

Figure 1. Configuration of design runs for a simplex lattice design.

Table 1. Formulation and evaluation of batches in a Simplex Lattice design.

Figure 2. A GC chromatogram of α-pinene, myrcene, and 3-carene (Run 9).

Table 2. Estimated regression coefficients for the polynomial model and the analysis of variance for the encapsulation efficacies of α-pinene, myrcene, and 3-carene from ICs.

Figure 3. Interaction effects of independent variables on the EE. EE, Encapsulation efficacy.

Figure 4. Overlap of EE; the white area has an encapsulation efficacy > 60% for all three components; × is the point of experimental design. EE, Encapsulation efficacy.

Figure 5. Spectra within 950–1650 nm. (a) Raw data; (b) MSC pretreatment; (c) SNV pretreatment; (d) 1th der pretreatment; (e) 2nd der pretreatment; (f) Result of PLS fitting after spectra pretreatment by 2nd der. MSC, Multiplicative scatter correction; SNV, Standard normal variate; 1th der, First derivative; 2nd der, Second derivative; PLS, Partial least squares.

Table 3. Parameters of PLS regression models for the determination of α-pinene, myrcene, and 3-carene in the IC.

Figure 6. Molecular structures of guest components inside the cavity of the β-CD with minimum energy obtained by molecular docking modeling. (a) α-Pinene docked into the β-CD cavity; (b) Myrcene docked into the β-CD cavity; (c) 3-Carene docked into the β-CD cavity.

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近红外光谱和混料实验设计研究β-环糊精差异化包封挥发油成分: 以包合α-蒎烯、月桂烯和3-蒈烯为例

Study of β-cyclodextrin differential encapsulation of essential oil components by using mixture design and NIR: Encapsulation of α-pinene, myrcene, and 3-carene as an example

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