Preparation, characterization, solubilization and antioxidant activity of polyamine modified β-cyclodextrins with baicalein inclusion complexes
- 14 Downloads
Inclusion complexes of three different lengths of polyamine modified β-cyclodextrins (β-CDs) (hosts 1–3) with baicalein (BC) were prepared by a solution stirring method, and characterized by UV–Vis spectroscopy, proton nuclear magnetic resonance, scanning electron microscopy, thermogravimetric analysis, and X-ray diffractometry. The results demonstrated that 1:1 inclusion complexes of hosts 1–3 with BC are present. The binding ability of hosts 1–3 towards BC increased according to the sequence H1 > H2 > H3, which was in good agreement with the decreasing chain lengths of these hosts. When compared to BC, the inclusion complexes produced 508-, 451- and 323-fold enhancement in water solubility, respectively. At low concentrations, inclusion complexes 1/BC and 3/BC were observed with a better capacity of scavenging when compared to that of free BC. These findings reflected that the complexation strengthened the antioxidant activity of BC. Moreover, the solubility in water and resistance to oxidation of hosts 1–3/BC were satisfactory, making it possible candidates for application in herbal medicine and as healthcare products.
KeywordsAntioxidant activity Baicalein Inclusion complexes Polyamine modified β-cyclodextrins Solubility
This work was supported by the National Natural Science Foundations (Nos. 21362046 and 21062030), which are gratefully acknowledged.
- 5.Kimata, M., Shichijo, M., Miura, T., Serizawa, I., Inagaki, N., Nagai, H.: Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells. Clin. Exp. Allergy 30, 501–508 (2000). https://doi.org/10.1046/j.1365-2222.2000.00768.x CrossRefPubMedGoogle Scholar
- 6.Kim, D.H., Jeon, S.J., Son, K.H., Jung, J.W., Lee, S., Yoon, B.H., Lee, J.J., Cho, Y.W., Cheong, J.H., Ko, K.H., Ryu, J.H.: The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice. Neurobiol. Learn. Mem. 87, 536–546 (2007). https://doi.org/10.1016/j.nlm.2006.11.005 CrossRefPubMedGoogle Scholar
- 8.Shao, Z.H., Vanden Hoek, T.L., Qin, Y., Becker, L.B., Schumacker, P.T., Li, C.Q., Dey, L..,Barth, E., Halpern, H., Rosen, G.M., Yuan, C.S.: Baicalein attenuates oxidant stress in cardiomyocytes. Am. J. Physiol. Heart Circ. Physiol. 282, H999–H1006 (2002). https://doi.org/10.1152/ajpheart.00163.2001 CrossRefPubMedGoogle Scholar
- 11.Zhou, Y., Dong, W., Ye, J., Hao, H., Zhou, J., Wang, R., Liu, Y.: A novel matrix dispersion based on phospholipid complex for improving oral bioavailability of baicalein: preparation, in vitro and in vivo evaluations. Drug Deliv. 24, 720–728 (2017). https://doi.org/10.1080/10717544.2017.1311968 CrossRefPubMedGoogle Scholar
- 22.Yang, L.J., Wang, S.H., Zhou, S.Y., Zhao, F., Chang, Q., Li, M.Y., Chen, W., Yang, X.D.: Supramolecular system of podophyllotoxin and hydroxypropyl-β-cyclodextrin: characterization, inclusion mode, docking calculation, solubilization, stability and cytotoxic activity. Mater. Sci. Eng. C 76, 1136 (2017). https://doi.org/10.1016/j.msec.2017.03.197 CrossRefGoogle Scholar
- 28.Ren, S.H., Zhang, J.Q., Yan, H.H., Zheng, X., Zhu, H.Y., Jin, Y., Lin, J.: Preparation, characterization, molecular docking and in vitro evaluation of two novel morin hydrate/CD inclusion complexes. J. Incl. Phenom. Macrocycl. Chem. 85, 317–328 (2016). https://doi.org/10.1007/s10847-016-0631-2 CrossRefGoogle Scholar