Stability, Antioxidant Activity and Intestinal Permeation of Oleuropein Inclusion Complexes with Beta-Cyclodextrin and Hydroxypropyl-Beta-Cyclodextrin

被引:10
作者
Liu, Hui [1 ]
Luo, Jinhua [1 ]
Yang, Ping [1 ]
Yang, Xiulan [2 ]
Yan, Jun [1 ]
Yao, Qian [1 ]
机构
[1] Chengdu Univ, Sch Pharm, Sichuan Ind Inst Antibiot,Sichuan Educ Dept, Key Lab Med & Edible Plants Resources Dev, Chengdu 610106, Peoples R China
[2] Chengdu Univ, Sch Food & Bioengn, Chengdu 610106, Peoples R China
关键词
oleuropein; beta-CD; hydroxypropyl-beta-CD; stability; intestinal permeation; ORAL BIOAVAILABILITY; PHENOLIC-COMPOUNDS; OLIVE OIL; SOLUBILITY; OPTIMIZATION; ENHANCEMENT; DISSOLUTION; MECHANISM; HEALTH; LEAVES;
D O I
10.3390/molecules27165077
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Compared to beta-cyclodextrins (beta-CD), hydroxypropyl-beta-cyclodextrins (HP-beta-CD) are a more popular material used to prepare inclusion complexes due to their superior solubility and intestinal absorption. In this study, oleuropein (OL) inclusion complexes with beta-CD (beta-CD:OL) and HP-beta-CD (HP-beta-CD:OL) were prepared and the formation of inclusion complexes was validated by IR, PXRD, and DSC. A phase solubility test showed that the lgK (25 degrees C) and binding energy of beta-CD:OL and HP-beta-CD:OL was 2.32 versus 1.98, and -6.1 versus -24.66 KJ/mol, respectively. Beta-CD:OL exhibited a more powerful effect than HP-beta-CD:OL in protecting OL from degradation upon exposure to light, high temperature and high humidity. Molecular docking, peak intensity of carbonyls in IR, and ferric reducing power revealed that beta-CD:OL formed more hydrogen bonds with the unstable groups of OL. Both inclusion complexes significantly enhanced the solubility, intestinal permeation and antioxidant activity of OL (p < 0.05). Though HP-beta-CD:OL had higher solubility and intestinal absorption over beta-CD:OL, the difference was not significant (p > 0.05). The study implies that lower binding energy is not always associated with the higher stability of a complex. Beta-CD can protect a multiple-hydroxyl compound more efficiently than HP-beta-CD with the intestinal permeation comparable to HP-beta-CD complex.
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页数:18
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