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Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2
- Source :
- Molecules; Volume 19; Issue 4; Pages: 5421-5433, Molecules, Molecules, Vol 19, Iss 4, Pp 5421-5433 (2014)
- Publication Year :
- 2014
- Publisher :
- Multidisciplinary Digital Publishing Institute, 2014.
-
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.
- Subjects :
- Magnetic Resonance Spectroscopy
Stereochemistry
Pharmaceutical Science
Molecular Dynamics Simulation
disaccharides
Article
Analytical Chemistry
lcsh:QD241-441
chemistry.chemical_compound
Molecular dynamics
lcsh:Organic chemistry
Drug Discovery
Pyridine
Carbohydrate Conformation
resin glycosides
Molecule
Cyclooxygenase Inhibitors
Glycosides
Ipomoea batatas
Physical and Theoretical Chemistry
Aqueous solution
Plant Extracts
Organic Chemistry
COX
Metadynamics
Nuclear magnetic resonance spectroscopy
molecular dynamics
inflammatory process
Carbohydrate Sequence
chemistry
Cyclooxygenase 2
Chemistry (miscellaneous)
Docking (molecular)
docking
Cyclooxygenase 1
ipomotaosides
Molecular Medicine
Carbohydrate conformation
Resins, Plant
Protein Binding
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Database :
- OpenAIRE
- Journal :
- Molecules; Volume 19; Issue 4; Pages: 5421-5433
- Accession number :
- edsair.doi.dedup.....417b28d38496a2a735b0023d8455a4e9
- Full Text :
- https://doi.org/10.3390/molecules19045421