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Computational Study of Shuangancistrotectorine A: A Naphthylisoquinoline Alkaloid with Antimalarial Activity

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Advances in Quantum Systems in Chemistry, Physics, and Biology (QSCP 2018)

Part of the book series: Progress in Theoretical Chemistry and Physics ((PTCP,volume 32))

Abstract

Shuangancistrotectorines A, B, C, D and E are naphthylisoquinoline alkaloids isolated from the twigs of Ancistrocladus tectorius, an indigenous plant in China and South East Asia. Their molecules are all C2-symmetric, i.e., they consist of two identical units. Each unit contains a naphthalene moiety and an isoquinoline moiety. Shuangancistrotectorine B and E are atropo-diastereomers of shuangancistrotectorine A and D respectively. Shuangancistrotectorine A, B and D exhibit very good and specific antimalarial activity, with shuangancistrotectorine A being the most active. The current work presents the results of a detailed conformational study of shuangancistrotectorine A, performed in vacuo and in three solvents with different polarities and different H-bonding abilities (chloroform, acetonitrile and water), using two levels of theory, HF/6-31G(d,p) and DFT/B3LYP/6-31+G(d,p). Particular attention is given to intramolecular hydrogen bonds’ patterns. The results show that intramolecular hydrogen bonds are the dominant factor influencing conformational preferences and energies, and also the other computable molecular properties. The mutual orientation of the moieties is also an energy-influencing factor, and the results show that all the moieties prefer to be perpendicular to each other. Comparisons with the results of other previously-investigated dimeric naphthylisoquinoline alkaloids are also included.

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Acknowledgements

The authors would like to thank the Centre for High Performance Computing (South Africa) for providing computational resources used to conduct this work. M. K. Bilonda is grateful to the National Research Foundation (NRF) of South Africa for a bursary to support her PhD studies.

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Authors and Affiliations

  1. University of Venda, Thohoyandou, South Africa

    Mireille K. Bilonda & Liliana Mammino

Authors
  1. Mireille K. Bilonda
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  2. Liliana Mammino
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Editor information

Editors and Affiliations

  1. School of Mathematical and Natural Sciences, University of Venda, Thohoyandou, South Africa

    Liliana Mammino

  2. Istituto di Scienze e Tecnologie Moleculari, Consiglio Nazionale delle Ricerche, Milan, Italy

    Davide Ceresoli

  3. Laboratoire de Chimie Physique, CNRS & UPMC, Paris, France

    Jean Maruani

  4. Department of Chemistry, Uppsala University, Uppsala, Sweden

    Erkki Brändas

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Bilonda, M.K., Mammino, L. (2020). Computational Study of Shuangancistrotectorine A: A Naphthylisoquinoline Alkaloid with Antimalarial Activity. In: Mammino, L., Ceresoli, D., Maruani, J., Brändas, E. (eds) Advances in Quantum Systems in Chemistry, Physics, and Biology. QSCP 2018. Progress in Theoretical Chemistry and Physics, vol 32. Springer, Cham. https://doi.org/10.1007/978-3-030-34941-7_10

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