Host-guest Interaction Between Cucurbit[8]uril and Pinocembrin and Its Influence on the Properties of Pinocembrin†

doi:10.7503/cjcu20170576

Abstract

Abstract:

The inclusion interaction between cucurbit [8] uril(Q[8]) and pinocembrin(PCB) was investigated by means of nuclear magnetic resonance spectrometer(NMR), UV-Visible spectrophotometer(UV-Vis) and differential thermal analysis(DTA). The results showed that PCB formed a molar ratio 1∶2 inclusion complex with Q[8] and located between the ports of the two rings. The stable binding constant is 5.00×10⁹ L²/mol². The effects of Q[8] on water solubility, stability, antioxidant activity and cumulative release of PCB were investigated by means of UV absorption spectroscopy. Phase solubility experiments showed that the solubility of PCB could be increased 4.3 fold by interacting when c(Q[8])=90 μmol/L. Both PCB-Q[8] and PCB had good scavenging effect on 2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate)(ABTS) free radicals, with IC₅₀values of 4.3 and 3.2 μmol/L, respectively. PCB and PCB-Q[8] were stable in the artificial gastric juice, and PCB was degraded completely after 72 h in the artificial intestinal fluid, but the degradation of PCB-Q[8] was hardly found. Q[8] increased the accumulation degree of PCB in artificial gastric and intestinal fluid by 5 and 2 times, respectively.

Key words: Pinocembrin, Cucurbit[8]uril, Inclusion complex, Antioxidant activity

CLC Number:

O624
O641.3

TrendMD:

LIAN Xiaowei, HUANG Jingjing, TAO Zhu, ZHOU Qingdi, ZHANG Qianjun, WEI Gang. Host-guest Interaction Between Cucurbit[8]uril and Pinocembrin and Its Influence on the Properties of Pinocembrin^†[J]. Chem. J. Chinese Universities, 2018, 39(2): 226.

Figures/Tables 11

Fig.1 Structures of pinocembrin(PCB)(A) and Q[8](B)

Fig.2 UV-Vis absorption spectra of PCB with Q[8](A) in aqueous solution and UV-Vis Job’s plot of ΔA against n(Q[8])/n(PCB) at 290 nm(B)Insert of (A) is the plot of absorbance at 290 nm of PCB. (A)c(PCB)=30 μmol/L; n(Q[8])/n(PCB): a. 0; b. 0.4; c. 0.8; d. 1.2; e. 1.6; f. 2; g. 2.4; h. 2.8; i. 3.2; j. 3.6.

Fig.3 UV-Vis absorption spectra of PCB with Q[8](A) in trifluoroacetic acid solution and UV-Vis Job’s plot of ΔA against n(Q[8])/n(PCB) at 290 nm(B)Insert of (A) is the plot of absorbance at 290 nm of PCB. c(PCB)=30 μmol/L; (A) n(Q[8])/n(PCB): a. 0; b. 0.4; c. 0.8; d. 1.2; e. 1.6; f. 2; g. 2.4; h. 2.8; i. 3.2; j. 3.6.

Fig.4 1H NMR spectra(400 MHz, D2O)(A), Hx(B) and 3-Ha(C) for the interaction between Q[8] and PCBa. Q[8]; b. n(PCB)/n(Q[8])=0.33; c. n(PCB)/n(Q[8])=0.5; d. n(PCB)/n(Q[8])=1; e. n(PCB)/n(Q[8])=2; f. PCB.

Fig.5 Possible mode of interaction between PCB and Q[8]

Fig.6 IR spectra of Q[8](a), PCB(b), physical mixture of PCB-Q[8](c) and PCB-Q[8](1∶2, molar ratio)(d)

Fig.7 DTA(A) and TG(B) curves of PCB(a), physical mixture of PCB and Q[8](b), Q[8](c) and PCB-Q[8](d)

Fig.8 UV spectra of saturated PCB in the presence of different concentrations of Q[8](A) and phase solubility graph of PCB in Q[8] at λ=290 nm(B) (A) c(Q[8])/(μmol/L): a. 0; b. 10; c. 30; d. 50; e. 70; f. 90.

Fig.9 Changes in UV absorption on intensity of PCB and PCB-Q[8] inclusion complex over time at pH=1.2(A) and 6.8(B)

Fig.10 Scavenging activity of PCB and PCB-Q[8] at different concentrations(A) and different time(B)

Fig.11 Release curves of PCB and PCB-Q[8] at pH=1.2(A) and 6.8(B)

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