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第 36 卷第 4 期 精 细 化 工 Vol.36, No.4
201 9 年 4 月 FINE CHEMICALS Apr. 2019

食品与饲料用化学品
不同环糊精对角鲨烯的包合作用

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张光杰 ，杜 磊 ，路志芳 ，袁 超 ，陈 笛
（1. 安阳工学院 生物与食品工程学院，河南 安阳 455000；2. 齐鲁工业大学 食品科学与工程学院，山
东 济南 250353）
摘要：角鲨烯是一种含有 6 个非共轭双键的直链三萜，其生理功能显著，但因水溶性及稳定性较差，限制了其
应用。采用相溶解度法，在 25、40 和 55 ℃下，考察了 α-环糊精、β-环糊精、γ-环糊精、羟丙基-β-环糊精及甲
基-β-环糊精对角鲨烯的包合作用，绘制相溶解图并计算包合过程中的热力学参数。结果表明:各相溶解图均为
A L 型，且 γ-环糊精的包合效果及增溶效果最为显著。γ-环糊精对角鲨烯的包合常数(K)最大可达 1778.0860 L/mol，
最大可将角鲨烯的溶解度增大至原来的 309.0935 倍。包合过程中的热力学参数焓变（ΔH）及熵变（ΔS）均为
正值，而吉布斯自由能（ΔG）均为负值，表明包合过程为吸热的自发反应，且无序化增加（熵增加）是环糊精
空腔包封角鲨烯分子的主要驱动力。
关键词：相溶解度；环糊精；角鲨烯；包合作用；食品化学品
中图分类号：TS209 文献标识码：A 文章编号：1003-5214 (2019) 04-0703-05

Inclusion of Squalene with Different Cyclodextrins

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ZHANG Guang-jie , DU Lei , LU Zhi-fang , YUAN Chao , CHEN Di
（1. School of Biotechnology and Food, Anyang Institute of Technology, Anyang 455000, Henan, China; 2. School of
Food Science and Engineering, Qilu University of Technology, Jinan 250353, Shandong, China）
Abstract: Squalene is a linear triterpenoid with six non-conjugated double bonds. Its physiological function
is remarkable, but its application is limited due to its poor water solubility and stability. The interactions
between squalene and different cyclodextrins, including α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin,
hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin were studied by phase solubility method at
different temperatures (25, 40 and 55 ℃). The phase dissolution diagrams were plotted and the
thermodynamic parameters during the inclusion process were calculated. The results showed that all phase
dissolving diagrams were A L type. The inclusion effect and solubilization effect of γ-cyclodextrin were the
most remarkable. The inclusion constant K of γ-cyclodextrin for squalene was up to 1778.0860 L/mol, and
the solubility of squalene increased to 309.0935 times. The thermodynamic parameters enthalpy change
(ΔH) and entropy change (ΔS) of the inclusion process were both positive values, while Gibbs free energy
(ΔG) were both negative values, indicating that the inclusion process was an endothermic spontaneous
reaction, and the increase of disorder (entropy increase) was the main driving force for the encapsulation of
squalene molecules in cyclodextrin cavities.
Key words: phase solubility; cyclodextrin; squalene; inclusion; food chemicals
Foundation items: National Natural Science Foundation of China (31571881); Henan Province Science
and Technology Attack Project (172102110003)

[3]
角鲨烯是 1906 年由日本化学家在鲨鱼肝油中 各类鲨鱼的肝脏中，且深海鲨鱼的含量最高 ，同
发现的一种高度不饱和且含有 6 个非共轭双键的直 时部分植物资源 [4-5] 中也有少量存在。1931 年，首次
链三萜类脂质非极性不皂化化合物 [1-2] ，主要存在于 被人工利用化学方法成功合成，并被命名为 2，6，

收稿日期：2018-08-24; 定用日期：2019-01-28; DOI: 10.13550/j.jxhg.20180621
基金项目：国家自然科学基金项目（31571881）；河南省科技攻关项目（172102110003）
作者简介：张光杰（1982—），男，博士生，讲师，E-mail：65671385@qq.com。