Isolation and purification of five phenolic compounds from the Xinjiang wine grape (Vitis Vinifera) and determination of their antioxidant mechanism at cellular level
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Xinjiang wine grapes (Vitis Vinifera) are extraordinarily rich sources of stilbenes. In this study, two pair of isomers of resveratrol dimers trans-ε-viniferin (1) and (+)-cis-ε-viniferin (2), astilbin (4) and isoastilbin (5), and resveratrol tetramer (−)-hopeaphenol (3) were isolated and purified. Their structures were determined by means of nuclear magnetic resonance and mass spectrometry analysis. Then, cellular antioxidant activity of the five phenolic compounds was evaluated in human hepatoma (Hep G2) cells. Results indicated that (4) has the strongest antioxidant activity (10 µg/mL), while (5) is the weakest one. Mechanism process of antioxidant at genes expression was elaborated by real-time quantitative PCR, which showed that the five stilbenes could down-regulation of oxidative stress genes and apoptosis genes. Therefore, this study provides the useful evidence for these compounds to develop the functional foods and nutritional supplements.
KeywordsXinjiang wine grape Isolation Purification Phenolic compounds Cell-based antioxidant activity Real-time quantitative PCR
This work was financially supported by National Natural Sciences Foundation of China (31671904, 31460411, 2136202 and 31260402), the Fundamental Research Funds for the Central Universities (GK201603095), Agricultural Science and Technology Innovation and Research (2016NY-184 and 2016NY-195), and Oversea Scholarship Program of Shaanxi Normal University.
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Conflict of interest
The authors declare that they have no conflict of interest.
Compliance with ethics requirements
This article does not contain any studies with human or animal subjects.
- 12.Vlassopoulos A, Lean MEJ, Combet E (2014) Oxidative stress, protein glycation and nutrition-interactions relevant to health and disease throughout the lifecycle. Proc Nutr Soc, 73, 430–438Google Scholar
- 14.Utkualp N, Ozdemir A (2015) Oxidative stress and chronic diseases. Oxid Commun 38:1690–1696Google Scholar
- 15.Zamora-Perez AL, Ortiz-Garcia YM, Lazalde-Ramos BP, Guerrero-Velazquez C, Gomez-Meda BC, Ramirez-Aguilar MA, Zuniga-Gonzalez GM (2015) Increased micronuclei and nuclear abnormalities in buccal mucosa and oxidative damage in saliva from patients with chronic and aggressive periodontal diseases. J Periodontal Res 50:28–36CrossRefGoogle Scholar
- 29.He YH, Kenji T, Yoshiaki T, Masatake N (2005) Structural confirmation of (+)-cis-ε-Viniferin. Chin J Nat Med 3:90–93Google Scholar
- 34.Jiao X, Li B, Zhang Q, Gao N, Zhang X, Meng X (2017) Effect of invitro-simulated gastrointestinal digestion on the stability and antioxidant activity of blueberry polyphenols and their cellular antioxidant activity towards hepg2 cells. International Journal of Food Science & TechnologyGoogle Scholar
- 36.Moscow JA, Morrow CS, He R, Mullenbach GT, Cowan KH (1992) Structure and function of the 5′-flanking sequence of the human cytosolic selenium-dependent glutathione peroxidase gene (hgpx1). J Biol Chem 267(9):5949Google Scholar