Elsevier

LWT

Volume 95, September 2018, Pages 255-261
LWT

Solubility improvement of hesperetin by using different octenyl succinic anhydride modified starches

https://doi.org/10.1016/j.lwt.2018.04.056Get rights and content

Highlights

  • Corn OSAS was the best in improving hesperetin's solubility.

  • The solubility of hesperetin was increased by 9.87 times.

  • The inclusion was confirmed by FT-IR, XRD and DSC.

Abstract

To increase the solubility of hesperetin, four different octenyl succinic anhydride modified starches (OSAS) were prepared from corn, wheat, potato, and sweet potato starches and then complexed with hesperetin. Results showed that corn OSAS was the best among the four OSASs in improving the hesperetin solubility. The solubilization efficiency of hesperetin was increased by 9.87 times when it was complexed with corn OSAS at 44 g/L mass concentration and degree of substitution (DS) at 0.0158 by agitation (1600 r/min, 40 °C) for 4 h under native pH. Compared with the physical mixture of OSAS and hesperetin, the inclusion of their complex was confirmed by FT-IR, XRD and DSC. These results would have provided some basic understandings on the interactions between hesperetin and OSAS on solubility enhancement.

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).

References (45)

  • M. Miao et al.

    Structure and physicochemical properties of octenyl succinic esters of sugary maize soluble starch and waxy maize starch

    Food Chemistry

    (2014)
  • T. Pralhad et al.

    Study of freeze-dried quercetin–cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis

    Journal of Pharmaceutical and Biomedical Analysis

    (2004)
  • A. Reddy et al.

    The pH of beverages in the United States

    The Journal of the American Dental Association

    (2016)
  • A. Roohbakhsh et al.

    Neuropharmacological properties and pharmacokinetics of the citrus flavonoids hesperidin and hesperetin-A mini-review

    Life Sciences

    (2014)
  • S.S. Shi et al.

    Process optimization for cassava starch modified by octenyl succinic anhydride

    Procedia Engineering

    (2012)
  • Y.B. Sun et al.

    Transdermal delivery of the in situ hydrogels of curcumin and its inclusion complexes of hydroxypropyl-β-cyclodextrin for melanoma treatment

    International Journal of Pharmaceutics

    (2014)
  • M.C. Sweedman et al.

    Structure and physicochemical properties of octenyl succinic anhydride modified starches: A review

    Carbohydrate Polymers

    (2013)
  • P.T.B. Trung et al.

    Impact of heat-moisture and annealing treatments onphysicochemical properties and digestibility of starches from different colored sweet potato varieties

    International Journal of Biological Macromolecules

    (2017)
  • X.Y. Wang et al.

    Preparation and characterisation of octenyl succinate starch as a delivery carrierfor bioactive food components

    Food Chemistry

    (2011)
  • S.J. Wang et al.

    Effects of hydrothermal-alkali and freezing-thawing pre-treatments on modification of corn starch with octenyl succinic anhydride

    Carbohydrate Polymers

    (2017)
  • Y.Q. Wei et al.

    Characterization of glabridin/hydroxypropyl-β-cyclodextrin inclusion complex with robust solubility and enhanced bioactivity

    Carbohydrate Polymers

    (2017)
  • Y.F. Xu et al.

    Modification of starch octenylsuccinate by β-amylase hydrolysis in order to increase its emulsification properties

    Food Hydrocolloids

    (2015)
  • Cited by (18)

    • Hydrophobically modified polysaccharides and their self-assembled systems: A review on structures and food applications

      2022, Carbohydrate Polymers
      Citation Excerpt :

      HMP unimers were often used as effective wall materials for HBCs. Because of their hydrophobic moieties, highly branched structure, and/or physical embedding effects, HMP unimers were able to harbor and disperse HBCs, and thus to improve their solubility and permeation, change their crystalline state, and even enable their biological efficacies (Guo et al., 2018; Xie & Yao, 2018). They were also used to protect some HBCs (e.g., CUR, β-carotene (βC), and vitamin E) that were easily oxidized and instable (Hategekimana, Masamba, Ma, & Zhong, 2015; Meng et al., 2020).

    • Effects of pullulanase debranching and octenylsuccinic anhydride modification on the structural properties of maize starch-green tea extract complexes

      2021, Food Hydrocolloids
      Citation Excerpt :

      As seen in Fig. 3b, for inclusion complexes, the characteristic peaks of debranched and OSCS-modified starches at approximately 3000–3700 cm−1 shifted to a higher frequency, indicating that there were interactions between debranched starches and bioactive components of GTE, and bioactive components restrained hydrogen bond formation of debranched and chemically-modified starches (Qi et al., 2017). Results demonstrated that the hydrogen bonding strength in DBS samples decreased, or an amorphous region increased with increasing of phenol or catechin content (Guo et al., 2018). TGA was used to assess thermal stabilities of materials by their mass changes as a function of temperature.

    • Effect of temperature, pH, β- and HP-β-cds on the solubility and stability of flavanones: Naringenin and hesperetin

      2019, LWT
      Citation Excerpt :

      As a result, there is a growing interest in using flavonoids to enrich food products in order to enhance their health functions, as well as in developing flavonoid-based nutraceutical and pharmaceutical products. However, the very poor water solubility of these flavanones imposes considerable limitations to their use (Guo et al., 2018). So, it is necessary to develop new formulations that incorporate naringein and hesperetin in foods to improve their solubility and in vivo bioavalilability.

    View all citing articles on Scopus
    View full text