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Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol

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Abstract

The objective of this paper is to study the effect of hydroxypropyl-β-cyclodextrin (HP-β-CD) complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol (PAE). The inclusion complex (PAE-HP-β-CD complex) of HP-β-CD and PAE was prepared by a freeze-drying method. Phase solubility tests showed that the stability constant of the inclusion complex was about 33.8 M−1 at 25 °C. The experimental results of proton nuclear magnetic resonance (H-NMR) spectroscopy, differential scanning calorimetry (DSC) and X-ray diffraction (XRD) suggested that PAE was included by HP-β-CD to form the PAE-HP-β-CD complex. Furthermore, the thermogravimetric analysis (TGA) results showed that the thermal stability of PAE was improved when it was complexed with HP-β-CD. Comparing the antioxidant activity of PAE with that of the PAE-HP-β-CD complex at the same concentration revealed that the complex of PAE with HP-β-CD was better able to eliminate radical. Furthermore, the experimental results revealed that the formation of a complex with HP-β-CD increased the water solubility of PAE, improving its apparent inhibitive activity of tyrosinase.

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Acknowledgments

This work was partially supported by a grant from China Medical University (CMU98-OC-01 and CMU99-S-10).

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Authors and Affiliations

  1. School of Chinese Medicine, China Medical University, Taichung, Taiwan

    Jung-Ying Tsao, Kuang-Chia Peng, Shan-Yu Su, Fuu-Jen Tsai & Yuhsin Tsai

  2. School of Post-Baccalaureate Chinese Medicine, China Medical University, Taichung, Taiwan

    Jung-Ying Tsao, Shan-Yu Su, Lieh-Der Chen & Fuu-Jen Tsai

  3. Department of Chinese Medicine, China Medical University Hospital, Taichung, Taiwan

    Jung-Ying Tsao & Shan-Yu Su

  4. Nano-Powder and Thin Film Technology Center, Industrial Technology Research Institute, Tainan, Taiwan

    Chien-Pang Wu & Hsieh-Ho Tsai

  5. Instrument Center of National Cheng Kung University, Tainan, Taiwan

    Pi-Yun Lin

  6. Department of Medical Genetics, Pediatrics and Medical Research, China Medical University Hospital, Taichung, Taiwan

    Fuu-Jen Tsai

  7. Department of Biotechnology and Bioinformatics, Asia University, Taichung, Taiwan

    Fuu-Jen Tsai

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  1. Jung-Ying Tsao
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Correspondence to Yuhsin Tsai.

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Tsao, JY., Wu, CP., Tsai, HH. et al. Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol. J Incl Phenom Macrocycl Chem 72, 405–411 (2012). https://doi.org/10.1007/s10847-011-0003-x

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