Enzymatic production of steviol using a commercial β-glucosidase and preparation of its inclusion complex with γ-CD
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Diterpenoid steviol and its derivatives have gained a growing interest for their broad therapeutic benefits in recent years. In nature, steviol exists primarily in the form of glycosides which are subject to hydrolysis after oral injestion. The present study evaluated the production of steviol using a new commercially available β-glucosidase and its inclusion complex, namely γ-cyclodextrin/steviol (γ-CD/steviol). Firstly, steviol was prepared by sequential hydrolysis from stevioside via steviolbioside, with the highest conversion of stevioside at 100% and a total yield of 64.9% based on the results of single factor experiments. To enhance steviol’s aqueous solubility, γ-CD/steviol was prepared by a co-evaporation method. Results showed that the solubility of steviol increased by a factor of 102 times using an 1:1 γ-CD/steviol inclusion complex. Physiochemical properties of the γ-CD/steviol complex were evaluated by HPLC, FT-IR, TGA, XRD, SEM and NMR. At ambient temperature, the γ-CD/steviol complex aqueous solution was extremely stable when assayed in the pH range from 4.01 to 9.18 up to 30 days.
KeywordsSteviol Stevioside Cyclodextrin Inclusion complex Solubility Stability
The authors were grateful to the financial support by National Natural Science Foundation of China (31371837).
- 6.Koubaa, M., Rosello-Soto, E., Sic Zlabur, J., Rezek Jambrak, A., Brncic, M., Grimi, N., Boussetta, N., Barba, F.J.: Current and new insights in the sustainable and green recovery of nutritionally valuable compounds from Stevia rebaudiana Bertoni. J. Agric. Food Chem. 63(31), 6835–6846 (2015)CrossRefGoogle Scholar
- 8.Dusek, J., Carazo, A., Trejtnar, F., Hyrsova, L., Holas, O., Smutny, T., Micuda, S., Pavek, P.: Steviol, an aglycone of steviol glycoside,sweeteners, interacts with the pregnane X (PXR) and aryl hydrocarbon (AHR) receptors in detoxification regulation. Food Chem. Toxicol. 109, 130–142 (2017)CrossRefGoogle Scholar
- 16.Hu, H., Sun, X.O., Tian, F., Zhang, H., Liu, Q., Tan, W.: Neuroprotective effects of isosteviol sodium injection on acute focal cerebral ischemia in rats. Oxid. Med. Cell. Longev. 2016, 1379162 (2016)Google Scholar
- 17.Lohoelter, C., Weckbecker, M., Waldvogel, S.R.: (-)-Isosteviol as a versatile Ex-Chiral-Pool building block for organic chemistry. Chem. Pharm. Bull. (Tokyo) 2013(25), 5539–5554 (2013)Google Scholar
- 20.Yi, J.G., Liang, W.T., Wei, X.Q., Yao, J.B., Yan, Z.Q., Su, D., Zhong, Z.H., Gao, G.W., Wu, W.H., Yang, C.: Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6(A),6(x)-diguanidio-gamma-cyclodextrins. Chin. Chem. Lett. 29(1), 87–90 (2018)CrossRefGoogle Scholar
- 21.Wei, X., Wu, W., Matsushita, R., Yan, Z., Zhou, D., Chruma, J.J., Nishijima, M., Fukuhara, G., Mori, T., Inoue, Y., Yang, C.: Supramolecular photochirogenesis driven by higher-order complexation: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate to slipped cyclodimers via a 2:2 complex with β-cyclodextrin. J. Am. Chem. Soc. 140(11), 3959–3974 (2018)CrossRefGoogle Scholar
- 27.Ohtani, K., Aikawa, Y., Fujisawa, Y., Kasai, R., Tanaka, O., Yamasaki, K.: Solubilization of steviolbioside and steviolmonoside with γ-cyclodextrin and its application to selective syntheses of better sweet glycosides from stevioside and rubusoside. Chem. Pharm. Bull. 39(12), 3172–3174 (1991)CrossRefGoogle Scholar
- 30.Higuchi, T., Connors, K.A.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)Google Scholar