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Molecules 2016, 21(1), 78; doi:10.3390/molecules21010078

Role of Nitric Oxide and Hydrogen Sulfide in the Vasodilator Effect of Ursolic Acid and Uvaol from Black Cherry Prunus serotina Fruits

1
Laboratorio de Investigación Química y Farmacológica de Productos Naturales, Facultad de Química, Universidad Autónoma de Querétaro, Centro Universitario, Querétaro 76010, Mexico
2
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria s/n, México D.F. 04510, Mexico
*
Author to whom correspondence should be addressed.
Academic Editor: Maurizio Battino
Received: 2 December 2015 / Revised: 5 January 2016 / Accepted: 6 January 2016 / Published: 12 January 2016
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [1341 KB, uploaded 12 January 2016]   |  

Abstract

The present research aimed to isolate the non-polar secondary metabolites that produce the vasodilator effects induced by the dichloromethane extract of Prunus serotina (P. serotina) fruits and to determine whether the NO/cGMP and the H2S/KATP channel pathways are involved in their mechanism of action. A bioactivity-directed fractionation of the dichloromethane extract of P. serotina fruits led to the isolation of ursolic acid and uvaol as the main non-polar vasodilator compounds. These compounds showed significant relaxant effect on rat aortic rings in an endothelium- and concentration-dependent manner, which was inhibited by NG-nitro-l-arginine methyl ester (l-NAME), dl-propargylglycine (PAG) and glibenclamide (Gli). Additionally, both triterpenes increased NO and H2S production in aortic tissue. Molecular docking studies showed that ursolic acid and uvaol are able to bind to endothelial NOS and CSE with high affinity for residues that form the oligomeric interface of both enzymes. These results suggest that the vasodilator effect produced by ursolic acid and uvaol contained in P. serotina fruits, involves activation of the NO/cGMP and H2S/KATP channel pathways, possibly through direct activation of NOS and CSE. View Full-Text
Keywords: hydrogen sulfide; in silico study; nitric oxide; Prunus serotina; ursolic acid; uvaol; vasodilation hydrogen sulfide; in silico study; nitric oxide; Prunus serotina; ursolic acid; uvaol; vasodilation
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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. (CC BY 4.0).

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MDPI and ACS Style

Luna-Vázquez, F.J.; Ibarra-Alvarado, C.; Rojas-Molina, A.; Romo-Mancillas, A.; López-Vallejo, F.H.; Solís-Gutiérrez, M.; Rojas-Molina, J.I.; Rivero-Cruz, F. Role of Nitric Oxide and Hydrogen Sulfide in the Vasodilator Effect of Ursolic Acid and Uvaol from Black Cherry Prunus serotina Fruits. Molecules 2016, 21, 78.

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