Enrichment of antioxidants from soy sauce using macroporous resin and identification of 4-ethylguaiacol, catechol, daidzein, and 4-ethylphenol as key small molecule antioxidants in soy sauce

Huipin Li; Lianzhu Lin; Yunzi Feng; Mouming Zhao; Xiuting Li; Qiyuan Zhu; Zuobing Xiao

doi:10.1016/j.foodchem.2017.08.001

Enrichment of antioxidants from soy sauce using macroporous resin and identification of 4-ethylguaiacol, catechol, daidzein, and 4-ethylphenol as key small molecule antioxidants in soy sauce

Food Chem. 2018 Feb 1:240:885-892. doi: 10.1016/j.foodchem.2017.08.001. Epub 2017 Aug 2.

Authors

Huipin Li¹, Lianzhu Lin¹, Yunzi Feng², Mouming Zhao³, Xiuting Li⁴, Qiyuan Zhu¹, Zuobing Xiao⁵

Affiliations

¹ School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China; Guangdong Food Green Processing and Nutrition Regulation Technologies Research Center, Guangzhou 510640, China.
² School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China; Guangdong Food Green Processing and Nutrition Regulation Technologies Research Center, Guangzhou 510640, China. Electronic address: feyzfeng@scut.edu.cn.
³ School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China; Guangdong Food Green Processing and Nutrition Regulation Technologies Research Center, Guangzhou 510640, China; Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology & Business University, Beijing 100048, China; Shanghai Institute of Technology, Shanghai 201418, China. Electronic address: femmzhao@scut.edu.cn.
⁴ Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology & Business University, Beijing 100048, China.
⁵ Shanghai Institute of Technology, Shanghai 201418, China.

PMID: 28946355
DOI: 10.1016/j.foodchem.2017.08.001

Abstract

The adsorption and desorption characteristics of seven macroporous resins on the antioxidants in soy sauce were investigated. SP-207 and SP-825 resins possessing good adsorption and desorption capacities were studied further. The pseudo-second-order kinetics and Langmuir isotherm models were demonstrated to be appropriate to describe the whole exothermic and physical adsorption processes of antioxidants onto resins. The 60% ethanol eluted fraction from soy sauce purified by SP-825 resin column possessed the strongest antioxidant activity. The antioxidant activities and contents of typical soy isoflavones, furanones, pyranones, and phenolic acids in soy sauce were determined. These compounds contributed to 50.02% of the total antioxidant activity of the SP-60% fraction. The key small molecule antioxidant compounds in soy sauce were identified as 4-ethylguaiacol, catechol, daidzein, and 4-ethylphenol by the antioxidants omission experiments. Additionally, the purified active fraction with high contents of antioxidants from soy sauce could be applied as bioactive ingredient in food industry.

Keywords: 4-Ethylguaiacol (PubChem CID: 62465); 4-Ethylphenol (PubChem CID: 31242); Antioxidants; Caffeic acid (PubChem CID: 689043); Catechol (PubChem CID: 289); Chlorogenic acid (PubChem CID: 1794427); Daidzein (PubChem CID: 5281708); Ferulic acid (PubChem CID: 445858); Furanones; Genistein (PubChem CID: 5280961); Glycitein (PubChem CID: 5317750); Isoflavones; Macroporous resins; Phenolic acids; Pyranones; Soy sauce; Syringic acid (PubChem CID: 10742).

MeSH terms

Antioxidants
Catechols
Guaiacol / analogs & derivatives
Isoflavones
Phenols
Soy Foods*

Substances

Antioxidants
Catechols
Isoflavones
Phenols
daidzein
Guaiacol
4-ethylphenol
4-ethylguaiacol