Citation: CHI Shao-Ming, YANG Song-Lin, JIN Wen, YANG Hui-Wen, WANG Yu-Fei, LEI Ze, ZHU Hong-You, ZHAO Yan. Inclusion and Antioxidant Properties of Taxifolin, Quercetin and Morin Hydrate with Diaminopropane Bridged Bis(β-cyclodextrin)s[J]. Chinese Journal of Analytical Chemistry, ;2020, 48(2): 215-223. doi: 10.19756/j.issn.0253-3820.191554 shu

Inclusion and Antioxidant Properties of Taxifolin, Quercetin and Morin Hydrate with Diaminopropane Bridged Bis(β-cyclodextrin)s

1.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China;
2.
Guangdong Goodscend Pharmaceutical Technology Co., Ltd, Shantou 515098, China

Received Date: 16 September 2019
Revised Date: 21 November 2019

Fund Project: This work was supported by the National Natural Science Foundation of China (Nos.21362046, 21062030) and the Yangfan Innovative and Entepreneurial Research Team Project (No. 201312S09).

Taxifolin (TFL), quercetin (QCT) and morin hydrate (MH) are common flavonoids in nature. They have many biological activities, such as antioxidant, anti-inflammatory, anti-allergic, anti-tumor and so on, but these compounds have poor water solubility and low oral utilization rate, which hinder the pharmacological action of these compounds. The bridged bis(β-cyclodextrin)s (bis(β-CD)s) has been known as it can significantly alter the molecular binding ability and the water solubility toward drug molecules, through the cooperative binding of drug molecule by two hydrophobic cavities located in close vicinity. In this work, the inclusion behavior of TFL, QCT and MH with diaminopropane bridged bis (β-CD)s) (H2) in solution and solid phase was studied. The three inclusion complexes (TFL/H2, QCT/H2 and MH/H2) were characterized by ultraviolet visible spectrum (UV-VIS), ¹H nuclear magnetic resonance spectrum (¹H NMR), two-dimensional nuclear magnetic resonance spectrum (2D NMR), scanning electron microscope (SEM), X-Ray diffraction spectrum (XRD) and Fourier transform infrared spectroscopy (FT-IR). The results showed that the A ring and C ring of the three flavonoids were separately included in two β-CD cavities from narrow side of H2, forming a 1:1 cooperative sandwich binding mode. The order of stability constant (K_S) of the three inclusion complexes was K_MH/_H2 > K_TFL/_H2 > K_QCT/_H2. The inclusion complex stability depended greatly on the host-guest size, shape matching relation and hydrogen bond interaction force. After the formation of inclusion complex, the solubility of TFL, QCT and MH in water increased by 130.2, 180.4 and 210.1 times, respectively. In addition, the antioxidant activities were determined by 1-diphenyl-2-trinitrophenylhydrazide (DPPH) radical scavenging method. Excitingly, the antioxidant activities of TFL/H2and MH/H2 inclusion complexes presented a satisfactory antioxidant activity, which was even higher than that of free drugs. The study provided an important reference for the development of flavonoids with high water solubility and good antioxidant activity.
- Taxifolin,
- Quercetin,
- Morin hydrate,
- Diaminopropane bridged bis(β-cyclodextrin)s,
- Cooperative bonding,
- Water solubility,
- Antioxidant activity
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