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Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C

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Abstract

Melinjo seed extract contains melinjo resveratrol compounds that has antioxidant activity. The radical-scavenging sites required for the antioxidant activity, however, is yet to be located. We report a computational study that aims to locate scavenging sites of the simplest resveratrol dimer, gnetin C. We consider the reaction of gnetin C and hydroperoxyl radical energetically with the basis of density-functional calculations, to be compared with the reaction of the resveratrol monomer, trans-resveratrol, and hydroperoxyl radical. The results show that OH group at the para position is the most reactive scavenging site for both molecules. Besides the OH group, gnetin C also provides two CH groups in the furan ring that are favorable as scavenging sites. Therefore, furan ring plays an important role in the scavenging activity, which is contrary to the experimental speculation that propose resorcinol ring. Our study shows the prospect of density-functional calculation for studying the radical-scavenging reaction.

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Acknowledgements

All calculations using Gaussian 09 software are performed in the computer facility at Research Research Center for Nanoscience and Nanotechnology, Institut Teknologi Bandung, Indonesia and Global Education Center, National Institute of Technology, Akashi College, Japan. VK thanks Rizka Nur Fadilla, Susan Aspera, Ryo Kishida, and Ryan Lacdao Arevalo for insightful discussions. VK and LSPB are grateful for the doctoral scholarship from Lembaga Pengelola Dana Pendidikan (LPDP) VK is also grateful for the Sandwich Program of Akashi College. FR appreciates partial financial support from Universitas Airlangga. This work is partially supported by the Ministry of Education and Culture, and the Ministry of Research and Technology of Republic of Indonesia, under the grant scheme “Penelitian Dasar Unggulan Perguruan Tinggi (PDUPT),” and the WCU Program managed by Institut Teknologi Bandung.

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Authors and Affiliations

  1. Research Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Surabaya, 60115, Indonesia

    Vera Khoirunisa, Febdian Rusydi & Lusia S. P. Boli

  2. Engineering Physics Study Program, Institut Teknologi Sumatera (ITERA, Lampung, 35365, Indonesia

    Vera Khoirunisa

  3. Advanced Functional Materials Research Group, Institut Teknologi Bandung, Bandung, 40132, Indonesia

    Vera Khoirunisa, Lusia S. P. Boli, Adhitya G. Saputro & Hermawan K. Dipojono

  4. Department of Physics, Faculty of Science and Technology, Universitas Airlangga, Surabaya, 60115, Indonesia

    Febdian Rusydi

  5. Research Center for Nanosciences and Nanotechnology, Institut Teknologi Bandung, Bandung, 40132, Indonesia

    Adhitya G. Saputro, Heni Rachmawati & Hermawan K. Dipojono

  6. School of Pharmacy, Institut Teknologi Bandung, Bandung, 40132, Indonesia

    Heni Rachmawati

  7. National Institute of Technology, Akashi College, Hyogo, 674-8501, Japan

    Hiroshi Nakanishi & Hideaki Kasai

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  1. Vera Khoirunisa
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  8. Hermawan K. Dipojono
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Contributions

Conceptualization: Febdian Rusydi; Methodology: Febdian Rusydi and Vera Khoirunisa; Formal analysis: Vera Khoirunisa, Lusia S. P. Boli; Investigation: Vera Khoirunisa; Writing - original draft preparation: Vera Khoirunisa; Writing - review and editing: Febdian Rusydi, Adhitya G. Saputro, Heni Rachmawati and Hermawan K. Dipojono; Resources: Hideaki Kasai and Hiroshi Nakanishi.

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Correspondence to Febdian Rusydi or Hermawan K. Dipojono.

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Khoirunisa, V., Rusydi, F., Boli, L.S.P. et al. Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C. Food Biophysics 16, 337–345 (2021). https://doi.org/10.1007/s11483-021-09666-y

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