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Enhancing Water Solubility and Stability of Natamycin by Molecular Encapsulation in Methyl-β-Cyclodextrin and its Mechanisms by Molecular Dynamics Simulations

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Abstract

In this study, the antifungal compound natamycin was encapsulated in methyl-β-cyclodextrin (heptakis(2,6-di-O-methyl)-β-cyclodextrin, Me-β-CD) to improve its aqueous solubility and stability. The aqueous solubilities of natamycin in the presence of β-CD, 2-hydroxypropyl-β-CD, 6-O-α-maltosyl-β-CD, and Me-β-CD were compared. The Me-β-CD showed the best result to increase the solubility of natamycin in aqueous. The pH stability of natamycin was improved by the formation of inclusion complex with Me-β-CD, especially at acidic conditions. The degradation of natamycin under UV-light exposure followed first-order kinetics with half-life times (t1/2) of 59.2 and 157.5 min in pure form and Me-β-CD inclusion complex, respectively. The in vitro antifungal activities of natamycin/Me-β-CD complex against Aspergillus niger food pathogen were evaluated. The results demonstrated that the natamycin/Me-β-CD complex could effectively improve the aqueous solubility and photostability of natamycin without compromising in antifungal activities. Finally, the molecular inclusion mechanisms and geometrical configurations of the natamycin/Me-β-CD complex were studied using molecular dynamics simulations. This research may lead to the development of more effective inclusion-based delivery systems to encapsulate and protect lipophilic antimicrobial agents for food applications.

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Acknowledgments

The authors acknowledge support from the Key Research and Development Project of Zhejiang Province, China (2019C02088).

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Authors and Affiliations

  1. School of Food Science and Biotechnology, Zhejiang Gongshang University, Xuezheng Street No. 18, Hangzhou, 310018, China

    Sheng Fang, Xinling Peng, Jian Wang, Jie Chen & Yuecheng Meng

  2. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, 310014, China

    Xianrui Liang

  3. School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo, 315016, China

    Jian Shen

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  1. Sheng Fang
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  2. Xinling Peng
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  3. Xianrui Liang
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Correspondence to Sheng Fang.

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Fang, S., Peng, X., Liang, X. et al. Enhancing Water Solubility and Stability of Natamycin by Molecular Encapsulation in Methyl-β-Cyclodextrin and its Mechanisms by Molecular Dynamics Simulations. Food Biophysics 15, 188–195 (2020). https://doi.org/10.1007/s11483-019-09620-z

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  • DOI: https://doi.org/10.1007/s11483-019-09620-z

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