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Target prediction and antioxidant analysis on isoflavones of demethyltexasin: a DFT study

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Abstract

Glycosylated flavonoids are often found in supplementary food sources and are structurally more active than aglycones, as the glycosyl unit offers better solubility, stability, and functionality. The most common glycosyl units present in most secondary metabolites are glucoside and rhamnoside attached to flavonoid moiety. In the present work, 4’-O–glycosylated (4’-O-glucoside and 4’-O-rhamnoside) demethyltexasin, a soy isoflavone bearing a chromen nucleus, is investigated through a green route aided by density functional theory. Antioxidant activity is computed via three different antioxidant mechanisms, in which hydrogen atom abstraction is facilitated effectively in both gas and solvent phases. The 6–OH site (A-ring) in both isoflavone demethyltexasin glucoside (DMTG) and isoflavone demethyltexasin rhamnoside (DMTR) acted as better radical scavenging sites. Charge localization in B-ring is well altered by the glycosyl and rhamnosyl groups attached. Target prediction analysis supports DMTG with good binding ability with the selected homosapien class targets. The results depict that even though the flavonoid possessing rhamnosyl unit induces charge delocalization at the 4’-O position, it offers resistance toward antioxidant activity when compared to glycosyl moeity.

The contour representation of antioxidants demethyltexasin 4’-O- glucoside (DMTG) and demethyltexasin 4’-O- rhamnoside (DMTR) against reactive oxygen species(ROS)

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Acknowledgments

The authors are sincerely thankful to the Science and Engineering Research Board, Department of Science and Technology (DST–SERB), and Government of India for funding the research. Grant Id. (EMR/2016/002892).

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Authors and Affiliations

  1. Quantum Computing and Phytochemistry Research Laboratory, Bannari Amman Institute of Technology, Sathyamangalam, Tamil Nadu, 638 401, India

    K. Anbazhakan, K. Sadasivam & R. Praveena

  2. Department of Physics, Bannari Amman Institute of Technology, Sathyamangalam, Tamil Nadu, 638 401, India

    K. Anbazhakan & K. Sadasivam

  3. Department of Chemistry, Bannari Amman Institute of Technology, Sathyamangalam, Tamil Nadu, 638 401, India

    R. Praveena

  4. Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, Tamil Nadu, 641 020, India

    M. Dhandapani

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  1. K. Anbazhakan
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Correspondence to R. Praveena.

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Anbazhakan, K., Sadasivam, K., Praveena, R. et al. Target prediction and antioxidant analysis on isoflavones of demethyltexasin: a DFT study. J Mol Model 25, 169 (2019). https://doi.org/10.1007/s00894-019-4045-0

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