Effects of Cucurbit[8]uril on the Solubility, Stability and Antioxidation of Cyanidin†

doi:10.7503/cjcu20180448

Abstract

Abstract:

The inclusion of cucurbit[8]uril(Q[8]) with cyanidin(Cy) was investigated and charactrized by means of nuclear magnetic resonance spectrometer, infrared spectroscopy and UV-visible spectrophotometer absorption spectroscopy. The results showed that Q[8] and Cy could form a 1:1 host-guest complex in acid aqueous medium and the host-guest binding constant was determined to be 1.51×10⁶. Phase solubility study results suggested that Q[8] could increase the solubility of saturated Cy solution up to 12.21 times, and the results of time-dependent UV-Vis absorption spectra indicated that the stability of Q[8]/Cy solution was 2.58 times higher than that of Cy solution in the same experimental conditions. The results of anti-oxidation experiments showed that both Q[8]/Cy inclusion compound and Cy showed good antioxidant activity.

Key words: Cucurbit[8]uril, Cyanidin, Solubility, Stability, Antioxidation

CLC Number:

O624
O641.3

TrendMD:

JIANG Jing,HUANG Yali,ZHANG Qilong,XU Hong,SUN Xiaohong. Effects of Cucurbit[8]uril on the Solubility, Stability and Antioxidation of Cyanidin^†[J]. Chem. J. Chinese Universities, 2019, 40(1): 76.

Figures/Tables 9

Fig.1 Scheme of the pH-dependent structure interconversion between dominant forms of anthocyanidins in aqueous solution

Fig.2 Structures of the host Q[8](A) and gust Cy(B)

Fig.3 Changes in UV-Vis absorption spectra(A), the plot(inset) and Job’s plot(B) of Cy with Q[8](A) c(Cy)=20 μmol/L; n(Q[8])/n(Cy), a—m: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.5, 3.0.

Fig.4 1H NMR spectra of interaction between Q[8] and Cy(pH=0.8) a. Cy; b. n(Q[8])/n(Cy)=1:1.

Scheme 1 Interaction of Q[8] with Cy

Fig.5 IR spectra of Q[8](a), Cy(b), Q[8]/Cy physical mixture(c) and Q[8]/Cy inclusion complex(d)

Fig.6 Changes in UV spectra of saturated Cy in the presence of different concentrations of Q8(A) and phase solubility graph of Cy in Q8 at λ=513 nm(B)c(Q[8])/(μmol·L-1): a. 20; b. 40; c. 60; d. 80; e. 100.

Fig.7 Changes in UV absorption intensity of Cy(a) and Q8/Cy(b) inclusion complex over timeInsets are changes in color over time. Left: 0 h; right: 60 h. a. c(Cy)=20 μmol/L; b. n([Q8])/n(Cy)=1:1.

Fig.8 Antioxidant capacity of Cy(a) and Q8/Cy(b) inclusion complex at different concentrations n([Q8])/n(Cy)=1:1.

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