Simulation of oleuropein structural conformation in vacuum, water and triolein-water systems using molecular dynamics

Souilem, Safa, Treesuwan, Witcha, Kobayashi, Isao, Khalid, Nauman, Bouallagui, Zouhaier, Neves, Marcos A., Uemura, Kunihiko, Isoda, Hiroko, Sayadi, Sami and Nakajima, Mitsutoshi 2016, Simulation of oleuropein structural conformation in vacuum, water and triolein-water systems using molecular dynamics, Food research international, vol. 88, pp. 79-90, doi: 10.1016/j.foodres.2016.04.003.

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Title Simulation of oleuropein structural conformation in vacuum, water and triolein-water systems using molecular dynamics
Author(s) Souilem, Safa
Treesuwan, Witcha
Kobayashi, Isao
Khalid, NaumanORCID iD for Khalid, Nauman
Bouallagui, Zouhaier
Neves, Marcos A.
Uemura, Kunihiko
Isoda, Hiroko
Sayadi, Sami
Nakajima, Mitsutoshi
Journal name Food research international
Volume number 88
Start page 79
End page 90
Total pages 12
Publisher Elsevier
Place of publication London, Eng.
Publication date 2016-10
ISSN 0963-9969
Summary Oleuropein, the main phenolic compound of olive leaves, exhibits a unique blend of biological activities and has been shown to locate itself at the oil-water (O/W) interface. This behavior could influence the physico-chemical properties of dispersed systems such as emulsions. In this work, we study the effect of the microenvironment (vacuum, water, and triolein-water) on the conformational preferences of oleuropein using molecular dynamics (MD) simulations at 300K for at least 30ns. The seven torsions that describe the flexible skeleton of oleuropein were monitored together with the distance between the glucose (Glu) and hydroxytyrosol (Hyd) moieties (dglu-hyd) of the molecule. The obtained trajectories demonstrated that oleuropein adopts different conformations that depend on the environment. The preferential conformers in each system were analyzed for their molecular geometry and internal energy. In vacuum, the oleuropein preferential conformation is tight with the glucose moiety in close proximity with the hydroxytyrosol moiety. In water, oleuropein preferential conformers presented large differences in their structural properties, varying from a close like U form, and a semi-opened form, to an opened form characterized by high fluctuations in dglu-hyd values. In a triolein-water system, oleuropein tends to adopt a more open form where the glucose moiety could be approximately aligned with the hydroxytyrosol and elenolic acid moieties. Based on a calculation at the HF/6-31G* level, these flexibilities of oleuropein required energy of 19.14kcal/mol in order to adopt the conformation between water and triolein-water system. A radial distribution function (RDF) analysis showed that specific hydroxyl groups of Hyd and Glu interact with water molecules, enabling us to understand the amphiphilic character of oleuropein at the triolein-water interface. MD calculations together with interfacial tension measurements revealed that the oleuropein binding at O/W interface is an enthalpy driven mechanism.
Language eng
DOI 10.1016/j.foodres.2016.04.003
Field of Research 090802 Food Engineering
080110 Simulation and Modelling
0904 Chemical Engineering
0908 Food Sciences
Socio Economic Objective 860303 Plant Extracts (e.g. Pyrethrum
HERDC Research category C1.1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2016, Elsevier
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Document type: Journal Article
Collection: School of Life and Environmental Sciences
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