Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 3; p. 684
• Main Authors: Ünlü, Ayşe, Teralı, Kerem, Uğurlu Aydın, Zübeyde, Dönmez, Ali A, Yusufoğlu, Hasan Soliman, Çalış, İhsan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 21-01-2022; MDPI
• Subjects: Anti-inflammatory agents; Anti-Inflammatory Agents - analysis; Asthma; Autoimmune diseases; Binding sites; Chromatography, High Pressure Liquid - methods; Endemic species; Enzymatic activity; Enzymes; Flavonoids - isolation & purification; Flavonoids - pharmacology; Flowers & plants; Glucosides - isolation & purification; Glucosides - pharmacology; Hydrogen bonding; Inflammatory diseases; liriodendrin; Metabolites; molecular docking; Molecular Docking Simulation; Molecular Structure; Nitric oxide; Nitric-oxide synthase; NMR; Nuclear magnetic resonance; ombuoside; Peroxidase; Phenylpropionates - isolation & purification; Phenylpropionates - pharmacology; Phytochemicals; Phytochemicals - analysis; Phytochemicals - isolation & purification; Plant Extracts - pharmacology; Plant Roots - chemistry; Polygala; Polygala - genetics; Polygala - metabolism; Prostheses; Secondary metabolites; Sucrose; Sucrose - isolation & purification; Sucrose - metabolism; sucrose esters; syringin; Turkey; Turkey; liriodendrin; ombuoside; molecular docking; sucrose esters; syringin
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27030684

species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on
, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3'-disinapoyl-sucrose (
), 6-
-sinapoyl,3'-
-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (
), 3'-
-(
-methyl-feruloyl)-sucrose (
), 3'-
-(sinapoyl)-sucrose (
), 3'-
-trimethoxy-cinnamoyl-sucrose (glomeratose) (
), 3'-
-feruloyl-sucrose (sibiricose A5) (
), sinapyl alcohol 4-
-glucoside (syringin or eleutheroside B) (
), liriodendrin (
), and 7,4'-di-
-methylquercetin-3-
-β-rutinoside (ombuin 3-
-rutinoside or ombuoside) (
). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (
H NMR,
C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some
-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities.