Next Article in Journal
Quantification, Antioxidant and Antimicrobial Activity of Phenolics Isolated from Different Extracts of Capsicum frutescens (Pimenta Malagueta)
Next Article in Special Issue
Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
Previous Article in Journal
In Vitro Studies of the Activity of Dithiocarbamate Organoruthenium Complexes against Clinically Relevant Fungal Pathogens
Previous Article in Special Issue
MALDI-TOF MS Analysis of Cellodextrins and Xylo-oligosaccharides Produced by Hindgut Homogenates of Reticulitermes santonensis
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,*
1 Centro de Biotecnologia, Universidade Federal do Rio Grande do Sul, Avenida Bento Gonçalves 9500, CP 15005, Porto Alegre, RS 91500-970, Brazil 2 Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Cidade Universitária, Seropedica, RJ 23897-000, Brazil
* Author to whom correspondence should be addressed.
Received: 5 March 2014 / Revised: 18 April 2014 / Accepted: 21 April 2014 / Published: 24 April 2014
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
View Full-Text   |   Download PDF [1346 KB, uploaded 18 June 2014]   |   Browse Figures

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.

Share & Cite This Article

Export to BibTeX |
EndNote


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.

View more citation formats

Supplement

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert