Solubility improvement of hesperetin by using different octenyl succinic anhydride modified starches
Introduction
Citrus flavonoids include flavanones, flavones, and anthocyanins etc., among which hesperidin and naringin are main components (Khan, Huma, & Dangles, 2014). Hesperetin (Fig. 1a) is the aglycone form of hesperidin, possessing potential health benefits such as antioxidant, anticarcinogenic, anti-inflammatory, anti-bacterial and anti-allergic activities (Mehrdad, Ramin, Hamideh, Ali, & Fatemeh, 2015; Roohbakhsh, Parhiz, Soltani, Rezaee, & Iranshahi, 2014). However, hesperetin has poor water solubility and consequently low bioavailability in living organism (Li et al, 2012b; Li, Jiang, Xu, & Gu, 2015). The low solubility also limits its direct application in food, medicine, cosmetics and other industries. Therefore, exploring methods to improve the solubility of hesperetin would be of high interests to industries.
Octenyl succinic anhydride modified starch (OSAS, Fig. 1b) is produced by the esterification reaction between starch and octenyl succinic anhydride (Sweedman, Tizzotti, Schäfer, & Gilbert, 2013; Zhang et al., 2015). It has been used as a new food emulsifier with the advantages that both hydrophilic and hydrophobic groups (1:1) are simultaneously introduced into the long chains of the starch, so it can exist in the oil-water interface stably and prevent the agglomeration of the emulsions. In addition, simple to prepare and in low cost (Song, 2007; Xu, Huang, Fu, & Jane, 2015). Recently, many scholars have reported the application of β-cyclodextrin in improving the solubility of flavonoids, such as hesperetin (Yang et al., 2016), hesperidin (Corciova, Ciobanu, Poiata, & Marangoci, 2014), naringin (Cui, Zhang, Sun, & Jia, 2012; Shulman et al., 2011; Wen, Liu, Yuan, Ma, & Zhu, 2010; Zhang, Liu, Hu, Bai, & Zhang, 2016) and quercetin (Borghetti, Lula, Sinisterra, & Bassani, 2009; Pralhad & Rajendrakumar, 2004). Other modified starches such as OSA-cyclodextrin (Lei, Liu, Ye, Chen, & Zhao, 2014) and hydroxypropyl-β-cyclodextrin (Jantarat et al., 2014; Sun et al., 2014) were also used to increase the solubility of curcumin, the principal curcuminoid of turmeric (Curcuma longa). However, to our knowledge, there is no report on the solubilization of hesperetin by OSAS.
In the present work, four types of OSAS were prepared by selecting starch origins, mass concentrations and degree of substitution (DS) of OSAS, and their structure differences were determined by scanning electron microscope (SEM). The hesperetin solubilization conditions were optimized and then the potential inclusion mechanisms between hesperetin and OSAS were evaluated by fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and differential scanning calorimetry (DSC). The results of this research could provide some fundamental knowledge on understanding the interactions between citrus flavonoids and OSAS and the improvement of water solubility of citrus flavonoids by OSAS.
Section snippets
Materials
Four common commercial starches were selected in this study. Corn, wheat, and potato starches of food grade were obtained from Taizhou Haoshihui Condiment Co., Ltd. (Jiangsu, China) and sweet potato starch was purchased from Shijiazhuang Zhongxing Sugar Co., Ltd. (Hebei, China). Octenyl succinic anhydride (OSA) was purchased from Jinan Haohua Industry Co., Ltd. (Shandong, China) and hesperetin (PC>98%) was obtained from Xi'an Xiaocao Botanical Development Co., Ltd. (Shanxi, China). Sodium
Solubilization efficiency of hesperetin by different OSAS
The maximum absorption wavelength of hesperetin was detected at 285 nm, which was consistent with the published results (Gu, Chen, Zhang, & Zang, 2016; Ko, Cheigh, & Chung, 2014). The maximum absorption of hesperetin-OSAS was also detected at 285 nm. Since OSAS had no absorption peak at 285 nm, this indicates that OSAS has no effect on the absorption spectra of hesperetin and hesperetin-OSAS complex. Because the hesperetin content in the supernatant was positively correlated with absorbance
Conclusions
OSAS, used as a new food surfactant, is relatively simple to prepare and in low cost. Compared with native hesperetin, corn OSAS was 9.87 times higher in improving the solubility of hesperetin in water, which would give some fundamental knowledge for the improvement of water solubility of citrus flavonoids by OSAS. The inclusion of corn OSAS and hesperetin had been confirmed by FT-IR, XRD and DSC analysis, which provided a sound basis for further investigation of the interaction between
Acknowledgements
This work was financially supported by the National Natural Science Foundation of China (31571892) and the Major Agricultural Program of Science and Technology of Zhejiang Province (2014C02021).
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