Molecular Encapsulation of Cinnamaldehyde within Cyclodextrin Inclusion Complex Electrospun Nanofibers: Fast-Dissolution, Enhanced Water Solubility, High Temperature Stability, and Antibacterial Activity of Cinnamaldehyde,Journal of Agricultural and Food Chemistry

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Molecular Encapsulation of Cinnamaldehyde within Cyclodextrin Inclusion Complex Electrospun Nanofibers: Fast-Dissolution, Enhanced Water Solubility, High Temperature Stability, and Antibacterial Activity of Cinnamaldehyde
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-09-25 , DOI: 10.1021/acs.jafc.9b02789
Zehra I Yildiz ₁ , Mehmet E Kilic ₁ , Engin Durgun _{1,

2} , Tamer Uyar _{1,

3}

Affiliation

The electrospinning of nanofibers (NFs) of cinnamaldehyde inclusion complexes (ICs) with two different hydroxypropylated cyclodextrins (CDs), hydroxypropyl-β-cyclodextrin (HP-β-CD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CD), was successfully performed in order to produce cinnamaldehyde/CD-IC NFs without using an additional polymer matrix. The inclusion complexation between cinnamaldehyde and hydroxypropylated CDs was studied by computational molecular modeling, and the results suggested that HP-β-CD and HP-γ-CD can be inclusion complexed with cinnamaldehyde at 1:1 and 2:1 (cinnamaldehyde/CD) molar ratios. Additionally, molecular modeling and phase solubility studies showed that water solubility of cinnamaldehyde dramatically increases with cyclodextrin inclusion complex (CD-IC) formation. The HP-β-CD has shown slightly stronger binding with cinnamaldehyde when compared to HP-γ-CD for cinnamaldehyde/CD-IC. Although cinnamaldehyde is a highly volatile compound, it was effectively preserved with high loading by the cinnamaldehyde/CD-IC NFs. It was also observed that cinnamaldehyde has shown much higher temperature stability in cinnamaldehyde/CD-IC NFs compared to uncomplexed cinnamaldehyde because of the inclusion complexation state of cinnamaldehyde within the hydroxypropylated CD cavity. Moreover, cinnamaldehyde still has kept its antibacterial activity in cinnamaldehyde/CD-IC NF samples when tested against Escherichia coli. In addition, cinnamaldehyde/CD-IC NF mats were fast-dissolving in water, even though pure cinnamaldehyde has a water-insoluble nature. In brief, self-standing nanofibrous mats of electrospun cinnamaldehyde/CD-IC NFs are potentially applicable in food, oral-care, healthcare, and pharmaceutics because of their fast-dissolving character, enhanced water solubility, stability at elevated temperature, and promising antibacterial activity.

中文翻译：

肉桂醛在环糊精包合物复合电纺纳米纤维中的分子包封：肉桂醛的快速溶解，增强的水溶性，高温稳定性和抗菌活性

肉桂醛包合配合物（ICs）与两种不同的羟丙基化环糊精（CD），羟丙基-β-环糊精（HP-β-CD）和羟丙基-γ-环糊精（HP-γ-CD）的纳米纤维（NFs）的静电纺丝原为无需使用其他聚合物基质即可成功完成生产肉桂醛/ CD-IC NF的操作。通过计算分子模型研究了肉桂醛与羟丙基化CDs的包合物，结果表明HP-β-CD和HP-γ-CD可以与肉桂醛以1：1和2：1（肉桂醛/ CD）包合。摩尔比。此外，分子建模和相溶解度研究表明，肉桂醛的水溶性会随着环糊精包合物（CD-IC）的形成而急剧增加。与肉桂醛/ CD-IC的HP-γ-CD相比，HP-β-CD与肉桂醛的结合稍强。尽管肉桂醛是一种高度挥发性的化合物，但肉桂醛/ CD-IC NFs可以有效地高负荷保存。还观察到肉桂醛在肉桂醛/ CD-IC NFs中显示出比未络合的肉桂醛更高的温度稳定性，这是因为肉桂醛在羟丙基化CD腔内的包合状态。此外，当对肉桂醛/ CD-IC NF样品进行测试时，肉桂醛仍保持其抗菌活性还观察到肉桂醛在肉桂醛/ CD-IC NFs中显示出比未络合的肉桂醛更高的温度稳定性，这是因为肉桂醛在羟丙基化CD腔内的包合状态。此外，当对肉桂醛/ CD-IC NF样品进行测试时，肉桂醛仍保持其抗菌活性还观察到肉桂醛在肉桂醛/ CD-IC NFs中显示出比未络合的肉桂醛更高的温度稳定性，这是因为肉桂醛在羟丙基化CD腔内的包合状态。此外，当对肉桂醛/ CD-IC NF样品进行测试时，肉桂醛仍保持其抗菌活性大肠杆菌。此外，即使纯肉桂醛具有水不溶性，肉桂醛/ CD-IC NF垫也可快速溶于水。简而言之，电纺制肉桂醛/ CD-IC NFs的自立式纳米纤维垫由于其快速溶解的特性，增强的水溶性，在高温下的稳定性以及有希望的抗菌性，因此潜在地可用于食品，口腔护理，保健和药物。活动。

更新日期：2019-09-26

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