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


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Unlu A., Terali K., Aydin Z. U., Donmez A. A., Yusufoglu H. S., ÇALIŞ İ.

MOLECULES, vol.27, no.3, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 3
  • Publication Date: 2022
  • Doi Number: 10.3390/molecules27030684
  • Journal Name: MOLECULES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Agricultural & Environmental Science Database, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, EMBASE, MEDLINE, Metadex, Veterinary Science Database, Directory of Open Access Journals, Civil Engineering Abstracts
  • Keywords: liriodendrin, molecular docking, ombuoside, sucrose esters, syringin, OLIGOSACCHARIDE MULTI-ESTERS, TRITERPENOID SAPONINS, SUCROSE ESTERS, NITRIC-OXIDE, PHENYLPROPANOID GLYCOSIDES, ANTINOCICEPTIVE PROPERTIES, HYDROALCOHOLIC EXTRACT, SABULOSA POLYGALACEAE, CHEMICAL-CONSTITUENTS, ADJUVANT ACTIVITIES
  • Hacettepe University Affiliated: Yes

Abstract

Polygala 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 Polygala inexpectata, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3 '-disinapoyl-sucrose (1), 6-O-sinapoyl,3 '-O-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (2), 3 '-O-(O-methyl-feruloyl)-sucrose (3), 3 '-O-(sinapoyl)-sucrose (4), 3 '-O-trimethoxy-cinnamoyl-sucrose (glomeratose) (5), 3 '-O-feruloyl-sucrose (sibiricose A5) (6), sinapyl alcohol 4-O-glucoside (syringin or eleutheroside B) (7), liriodendrin (8), and 7,4 '-di-O-methylquercetin-3-O-beta-rutinoside (ombuin 3-O-rutinoside or ombuoside) (9). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (H-1 NMR, C-13 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 pi-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some Polygala-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities.