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Article

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

by
Markhabo M. Makhmudova
1,
Markus Bacher
2,
Gokhan Zengin
3,
Thomas Rosenau
2,
Fadia S. Youssef
4,
Diena M. Almasri
5,
Sameh S. Elhady
6 and
Nilufar Z. Mamadalieva
1,*
1
Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent 100170, Uzbekistan
2
Department of Chemistry, Institute of Chemistry of Renewable Resources, University of Natural Resources and Life Sciences Vienna (BOKU), 3430 Tulln, Austria
3
Department of Biology, Science Faculty, Selcuk University, Konya 42130, Turkey
4
Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Abbasia, Cairo 11566, Egypt
5
Department of Pharmacy Practice, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia
6
Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(24), 8781; https://doi.org/10.3390/molecules27248781
Submission received: 4 November 2022 / Revised: 1 December 2022 / Accepted: 6 December 2022 / Published: 11 December 2022
(This article belongs to the Special Issue Analysis of Plant Metabolites, Antioxidants Compound and Enzymes Activity in Plants)
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Abstract

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.
Keywords: Silene viridiflora; triterpene glycoside; silviridoside; antioxidant; enzyme inhibitor; ADME/TOPKAT; drug discovery; sustainability of natural resources Silene viridiflora; triterpene glycoside; silviridoside; antioxidant; enzyme inhibitor; ADME/TOPKAT; drug discovery; sustainability of natural resources

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MDPI and ACS Style

Makhmudova, M.M.; Bacher, M.; Zengin, G.; Rosenau, T.; Youssef, F.S.; Almasri, D.M.; Elhady, S.S.; Mamadalieva, N.Z. Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential. Molecules 2022, 27, 8781. https://doi.org/10.3390/molecules27248781

AMA Style

Makhmudova MM, Bacher M, Zengin G, Rosenau T, Youssef FS, Almasri DM, Elhady SS, Mamadalieva NZ. Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential. Molecules. 2022; 27(24):8781. https://doi.org/10.3390/molecules27248781

Chicago/Turabian Style

Makhmudova, Markhabo M., Markus Bacher, Gokhan Zengin, Thomas Rosenau, Fadia S. Youssef, Diena M. Almasri, Sameh S. Elhady, and Nilufar Z. Mamadalieva. 2022. "Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential" Molecules 27, no. 24: 8781. https://doi.org/10.3390/molecules27248781

APA Style

Makhmudova, M. M., Bacher, M., Zengin, G., Rosenau, T., Youssef, F. S., Almasri, D. M., Elhady, S. S., & Mamadalieva, N. Z. (2022). Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential. Molecules, 27(24), 8781. https://doi.org/10.3390/molecules27248781

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