title: Isoflavones from Maclura pomifera: structural elucidation and in silico evaluation of their interaction with PDE5.
abstract: While osajin and pomiferin are known for their anticancer, antibacterial and antidiabetic properties, scandenone and auriculasin have been proposed as anti-inflammatory and antinociceptive agents. Curiously, these two couples of molecules are, from a chemical point of view, structural isomers which can all be extracted from Maclura pomifera. Although previous works described, separately, the isolation in reasonable amounts of the sole osajin/pomiferin couple or of scandenone/auriculasin, we report the extraction and characterization using direct spectral and chromatographical comparison of the four compounds. 2D NMR allowed to unambiguously assign the correct structures to the isomers. The compounds were screened in silico against PDE5 and their interaction pattern with the protein was compared with that of icarisid II, a natural PDE5 inhibitor.
authors.affiliation: a Department of Pharmaceutical and Pharmacological Sciences , University of Padova , Padova , Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Ribaudo
authors.affiliation: b Accademia Trevigiana per il Territorio , Treviso , Italy.
authors.forename: Tiziano
authors.initials: T
authors.lastname: Vendrame
authors.affiliation: a Department of Pharmaceutical and Pharmacological Sciences , University of Padova , Padova , Italy.
authors.forename: Sergio
authors.initials: S
authors.lastname: Bova
mesh_terms: D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D003198:Computer Simulation; D054706:Cyclic Nucleotide Phosphodiesterases, Type 5 / Q000737:chemistry / Q000378:metabolism*; D007529:Isoflavones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D007536:Isomerism; D031624:Maclura / Q000737:chemistry*; D062105:Molecular Docking Simulation; D015394:Molecular Structure
chemical_list: D001578:Benzopyrans; D007529:Isoflavones; C516713:auriculasin; C516712:scandenone; C474837:pomiferin; C485800:osajin; D054706:Cyclic Nucleotide Phosphodiesterases, Type 5
keywords: PDE5; icarisid II; isoflavonoids; sildenafil