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Theoretical conformational analysis of rutin

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Abstract

The structural properties of rutin were determined by using a computational multistep progression. In the first step a stochastic strategy based on a molecular mechanics calculation was adopted to obtain a preliminary screening of the low-energy rutin conformations. The most stable structures obtained by the random conformational search were used as a starting point for an Austin Model 1 (AM1) semiempirical optimization. After this treatment, 16 structures characterized by a more stable frontal in respect to back disposition of the glycosidic chain of rutin were identified. To validate the results found from the stochastic search a molecular dynamics simulation was carried out. The results evidenced the presence of a global minimum highly stabilized by a hydrogen bond between the hydroxyl in the 3′ position of the B ring and the endocyclic oxygen of the rhamnose unit followed by approximately 8 kJ mol−1 less stable local minima with similar energy values. Finally, the reliability of the molecular model was confirmed by comparing the calculated electronic absorption spectrum with that measured on a methanolic rutin solution.

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Authors and Affiliations

  1. Institute of Applied Physics “Nello Carrara”, National Research Council, via Madonna del Piano 10, 50019, Sesto Fiorentino, Italy

    Paolo Matteini & Giovanni Agati

  2. Department of Organic Chemistry “Ugo Schiff”, University of Florence, via della Lastruccia 3, 50019, Sesto Fiorentino, Italy

    Andrea Goti

Authors
  1. Paolo Matteini
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  2. Andrea Goti
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  3. Giovanni Agati
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Correspondence to Paolo Matteini.

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Matteini, P., Goti, A. & Agati, G. Theoretical conformational analysis of rutin. Monatsh Chem 141, 793–800 (2010). https://doi.org/10.1007/s00706-010-0330-4

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  • DOI: https://doi.org/10.1007/s00706-010-0330-4

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