Host-Guest Inclusion Systems of Morin Hydrate and Quercetin with Two Bis(β-cyclodextrin)s: Preparation, Characterization, and Antioxidant Activity
Li-Juan Zhao A , Song-Lin Yang A C , Wen Jin A , Hui-Wen Yang A , Fei-Yang Li A , Shao-Ming Chi A , Hong-You Zhu B , Ze Lei B and Yan Zhao A DA College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China.
B Guangdong Gusheng Pharmaceutical Technology Co., Ltd, Shantou 515098, China.
C This author contributed to the work equally and should be regarded as co-first author.
D Corresponding author. Email: zhaooyann@163.com
Australian Journal of Chemistry 72(6) 440-449 https://doi.org/10.1071/CH18580
Submitted: 29 November 2018 Accepted: 11 February 2019 Published: 12 March 2019
Abstract
The inclusion complexation behaviour of morin hydrate (MH) and quercetin (QCT) with the two amide-bridged bis(β-cyclodextrin (β-CD))s, 1 and 2, was investigated in both solution and the solid state. The inclusion complexations were characterised by proton nuclear magnetic resonance, 2D rotating-frame Overhauser effect spectroscopy, X-ray powder diffraction, infrared spectroscopy and scanning electron microscopy. Ultraviolet titration analysis indicated that 1 and 2 form 1 : 1 molar stoichiometry inclusion complexes with MH and QCT, and the data obtained showed that 2 with two guests has a higher complex stability constant (KS) when compared with that of 1. Moreover, 1 and 2 were able to solubilize MH and QCT to high levels, up to ~200-fold. Furthermore, the antioxidant activity of MH, QCT and their inclusion compounds were determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging. Together, these results showed that the inclusion complexes exhibited a more effective antioxidant activity when compared with free MH. The satisfactory antioxidant activity and high water solubility of the bis(β-CD)s/flavonoid complexes may have potential use as healthcare products and herbal medicine.
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