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DFT-based quantitative structure–activity relationship studies for antioxidant peptides

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Abstract

Peptides derived from food sources exhibit many different biological properties, including antioxidant activities. Some antioxidant activities are attributed to the scavenging of free radicals through electron transfer. In this study, the quantum chemical parameters associated with electron transfer were investigated. All calculations were performed using the Gaussian 03 W software package using DFT theory (B3LYP hybrid functions), together with the 6-311 + G (d, p) basis set that supported the experimental free radical (·OH and O2 −·) scavenging activities. The results of the scavenging O2 −· model (R 2 = 0.882, Q 2 = 0.824) demonstrated that O2 −· model has a high statistical significance and remarkable predictive ability; however, ·OH model was not prominent. We used the multiple linear regression to build the model and used the leave-one-out method to verify the regression’s prediction. The results showed that EHOMO and L, related to electron donating ability, are the most important parameters for understanding the free radical especially O2 −· scavenging ability of antioxidant peptides. The information obtained from this study could provide clues for the guided synthesis of antioxidant peptides.

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Acknowledgments

This work is financially supported by the National Natural Science Foundation of China (31171672, 31071523), the Key Programs from MOST (2012BAD34B02, 2011BAK10B05, 2012BAD29B05), Public Program from the General Administration of Quality Supervision (201310128),and Grants from the Ministry of Health Foundation of China (W201304), and Hunan Provincial Innovation Foundation for Postgraduate (CX2014B387).

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Authors and Affiliations

  1. School of Chemistry and Biology Engineering, Changsha University of Science & Technology, Changsha, 410114, China

    Yunhui Cheng, Fang Luo, Zhiyin Zeng, Li Wen, Zhongliang Xiao, Hanping Bu, Fei Lv & Zhou Xu

  2. National Engineering Laboratory for Rice and By-product Deep Processing, Central South University of Forestry and Technology, Changsha, 410114, China

    Qinlu Lin

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  1. Yunhui Cheng
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  2. Fang Luo
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  3. Zhiyin Zeng
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  4. Li Wen
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  5. Zhongliang Xiao
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  6. Hanping Bu
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  7. Fei Lv
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  8. Zhou Xu
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  9. Qinlu Lin
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Correspondence to Yunhui Cheng.

Additional information

Yunhui Cheng and Fang Luo authors contributed to this paper equally.

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Cheng, Y., Luo, F., Zeng, Z. et al. DFT-based quantitative structure–activity relationship studies for antioxidant peptides. Struct Chem 26, 739–747 (2015). https://doi.org/10.1007/s11224-014-0533-0

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  • DOI: https://doi.org/10.1007/s11224-014-0533-0

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