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Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential

Markhabo M. MakhmudovaInstitute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent 100170, UzbekistanMarkus BacherDepartment of Chemistry, Institute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), 3430 Tulln, AustriaGokhan ZenginDepartment of Biology, Science Faculty, Selcuk University, Konya 42130, TurkeyThomas RosenauDepartment of Chemistry, Institute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), 3430 Tulln, AustriaFadia S. YoussefDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbasia, Cairo 11566, EgyptDiena M. AlmasriDepartment of Pharmacy Practice, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaSameh S. ElhadyDepartment of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaNilufar Z. MamadalievaInstitute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent 100170, Uzbekistan
Moleculesjournal2022en
ABI

Annotatsiya

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary.

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