Conformational characterization of ipomotaosides and their recognition by COX-1 and 2

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...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2014-04, Vol.19 (4), p.5421-5433
Main Authors: Arantes, Pablo R, Sachett, Liana G, Graebin, Cedric S, Verli, Hugo
Format: Article
Language:English
Subjects:
Aqueous solutions
Carbohydrate Conformation
Carbohydrate Sequence
Carbohydrates
COX
Cyclooxygenase 1 - chemistry
Cyclooxygenase 2 - chemistry
Cyclooxygenase Inhibitors - chemistry
disaccharides
docking
Enzymes
Glycosides - chemistry
inflammatory process
Ipomoea batatas - chemistry
ipomotaosides
Magnetic Resonance Spectroscopy
molecular dynamics
Molecular Dynamics Simulation
Plant Extracts - chemistry
Protein Binding
resin glycosides
Resins, Plant - chemistry
Simulation
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules19045421