Influence of Interaction with Cucurbit[7]uril on Solubility, Stability and Antioxidant Activity of 2'-Hydroxychalcone†

doi:10.7503/cjcu20160733

Abstract

Abstract:

The host-guest interactions and properties of 2'-hydroxychalcone(CET) with cucurbit[7]uril(Q[7]) were investigated by means of ¹H NMR, IR, UV-Vis absorption and fluorometry spectroscopy. The results revealed that 2'-hydroxychalcone could form an inclusion complex of 1∶1 with Q[7]. The inclusion constants of CET with Q[7] obtained by UV absorption and fluorescence spectroscopy were 1.0248×10⁶ and 1.253×10⁶, respectively. The phase-solubility experiments revealed that the solubility of CET increased 52 times by interacting with Q[7][c(Q[7])=1×10^-3 mol/L]. The time-scaled UV absorption spectra showed that Q[7] increases the stability of CET by 3.5 times. The antioxidant activity(ABTS method) of both the CET@Q[7] inclusion complex and CET proved to be good scavenging effect to the ABTS radical, IC₅₀ values were 3.4×10^-5 and 2.4×10^-5 mol/L, respectively. Thus, Q[7] could not only increase the solubility and stability of CET, but also have little effect on the antioxidant activity of CET. As a result, stability and water solubility were obviously improved.

Key words: Chalcone, Cucurbit[7]uril(Q[7]), Inclusion complex, Antioxidant activity, Stability

CLC Number:

O641.3

TrendMD:

LI Mengjie, LIAN Xiaowei, XU Zhiling, XING Xuyang, ZHANG Jianxin, LI Rui, TAO Zhu, ZHANG Qianjun. Influence of Interaction with Cucurbit[7]uril on Solubility, Stability and Antioxidant Activity of 2'-Hydroxychalcone^†[J]. Chem. J. Chinese Universities, 2017, 38(3): 442.

Figures/Tables 10

Fig.1 Structures of 2'-hydroxychalcone(CET)(A) and Q[7](B)

Table 1 Data from gCOSY 2D NMR spectrum of CET[V(CD3OD)∶V(D2O)=2∶3, 400 MHz]

Position	δ, H	¹H-¹H COSY	Position	δ, H	¹H-¹H COSY
2,4,6	7.78(3H, brs)	2,4,6-H/3,5-H	4'	7.61(1H, t)	4'-H/3',5'-H
3,5	7.48(2H, brs)	3,5-H/2,4,6-H	5'	7.09(1H, t)	5'-H/4',6'-H
α, β	7.87(2H, s)		6'	8.15(1H, d)	6'-H/5'-H
3'	7.03(1H, d)	3'-H/4'-H

Fig.2 1H NMR spectra of CET(a), Q[7]@CET system CET[n(Q[7])∶n(CET)=1∶1](b) and Q[7](c)

Scheme 1 Interaction of CET with Q[7]

Fig.3 Changes in UV spectra(A), the plot(inset) and Job’s plot(B) of CET with Q[7]

Fig.4 Changes in fluorescence spectra and plot(insert) of CET(2.5 μmol/L) with Q[7] c(CET)/(μmol·L-1) from top to bottom: 0, 6.25, 12.5, 18.75, 25.0, 31.25, 37.5, 43.75, 50.0, 62.5, 75.0.

Fig.5 IR spectra of CET(a), Q[7](b), physical mixture of CET and Q[7](c), as well as CET@Q[7] inclusion complex(d)

Fig.6 Changes in UV spectra of saturated CET in the presence of different concentrations of Q[7](A) and phase solubility graph of CET in Q[7] at λ=322 nm(B) c(Q[7])/(μmol·L-1) from bottom to top: 20, 40, 60, 80, 100.

Fig.7 Changes in UV absorption intensity of CET(a) and CET@Q[7](b) inclusion complex over time

Fig.8 Scavenging activity of CET(a) and CET@Q[7](b) inclusion complex at different concentrations(A) and different time(B)

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