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Molecules 2014, 19(4), 5421-5433; doi:10.3390/molecules19045421
Article

Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2

1
, 1
, 2
 and 1,*
Received: 5 March 2014; in revised form: 18 April 2014 / Accepted: 21 April 2014 / Published: 24 April 2014
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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Abstract: The aerial parts of Ipomoea batatas are described herein to produce four new resin glycosides, designated as ipomotaosides A, B, C, and D. Ipomotaoside A was found to present inhibitory activity on both cyclooxygenases. However, the conformational elucidation of these molecules may be difficult due to their high flexibility. In this context, the current work presents a conformational characterization of ipomotaosides A–D in aqueous and nonaqueous solvents. The employed protocol includes metadynamics evaluation and unrestrained molecular dynamics simulations (MD). The obtained data provided structural models for the ipomotaosides in good agreement with previous ROESY distances measured in pyridine. Accordingly, the most abundant conformation of ipomotaoside A in solution was employed in flexible docking studies, providing a structural basis for the compound’s inhibition of COX enzymes. The so-obtained complex supports resin glycosides’ role as original scaffolds for future studies, aiming at structural optimization and development of potential new anti-inflammatory agents.
Keywords: ipomotaosides; resin glycosides; disaccharides; molecular dynamics; docking; COX; inflammatory process ipomotaosides; resin glycosides; disaccharides; molecular dynamics; docking; COX; inflammatory process
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Arantes, P.R.; Sachett, L.G.; Graebin, C.S.; Verli, H. Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2. Molecules 2014, 19, 5421-5433.

AMA Style

Arantes PR, Sachett LG, Graebin CS, Verli H. Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2. Molecules. 2014; 19(4):5421-5433.

Chicago/Turabian Style

Arantes, Pablo R.; Sachett, Liana G.; Graebin, Cedric S.; Verli, Hugo. 2014. "Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2." Molecules 19, no. 4: 5421-5433.


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