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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Francisco J Luna-VázquezFausto Rivero-Cruz

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.

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Citations

Jun 19, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Francisco J Luna-VázquezMoustapha Bah
Mar 14, 2019·Natural Product Research·Daniela Alejandra Torres-OrtizRivera-Pastrana Dulce María
Sep 22, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cheolmin JoHo-Young Choi
Dec 12, 2019·Critical Reviews in Food Science and Nutrition·Raquel MateosLaura Bravo
Nov 1, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Julianderson CarmoEmiliano Barreto
Apr 4, 2021·International Journal of Molecular Sciences·Anna Bartáková, Marie Nováková
Jul 9, 2021·Fitoterapia·Christian J Valencia-GuzmánCésar Ibarra-Alvarado

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Methods Mentioned

BETA
column chromatography
nuclear magnetic resonance
Assay

Software Mentioned

LigPrep
Prime
Maestro
GraphPad Pad
Schrödinger Maestro Suite
GraphPad
Impact
Protein Preparation Wizard Preparation Wizard
Glide
PRISM

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