Abstract
In recent years, the use of Sideritis species as bioactive agents is increasing exponentially. The present study aimed to investigate the chemical constituents, as well as the anti-ageing potential of the cultivated Sideritis euboea Heldr. The chemical fingerprinting of the ethyl acetate residue of this plant was studied using 1D and 2D-NMR spectra. Isomeric compounds belonging to acylated flavone derivatives and phenylethanoid glycosides were detected in the early stage of the experimental process through 2D-NMR techniques. Overall, thirty-three known compounds were isolated and identified. Some of them are reported for the first time not only in S. euboea, but also in genus Sideritis L. The anti-ageing effect of the ethyl acetate residue and the isolated specialized products was assessed as anti-hyaluronidase activity. In silico docking simulation revealed the interactions of the isolated compounds with hyaluronidase. Furthermore, the in vitro study on the inhibition of hyaluronidase unveiled the potent inhibitory properties of ethyl acetate residue and apigenin 7-O-β-d-glucopyranoside. Though, the isomers of apigenin 7-O-p-coumaroyl-glucosides and also the 4′-methyl-hypolaetin 7-O-[6′′′-O-acetyl-β-d-allopyranosyl]-(1→2)-β-d-glucopyranoside exerted moderate hyaluronidase inhibition. This research represents the first study to report on the anti-hyaluronidase activity of Sideritis species, confirming its anti-inflammatory, cytotoxic and anti-ageing effects and its importance as an agent for cosmetic formulations as also anticancer potential.
Highlights
Natural Products (NPs) continue to be the major source for drug leads, providing unique structurally diverse chemical scaffolds [1]
The cultivation of Sideritis species has been viewed as a dynamic solution that could contribute to reducing the extensive collection and the potential extinction of the natural wild populations, to produce raw materials in sufficient quantities for the industrial-scale production demanded, and most importantly, to affirm for high quality and standardized products
The methanol extract of the aerial parts of the cultivated S. euboea Heldr. was suspended in boiling water and this water-soluble fraction was successively partitioned with ethyl acetate (EtOAc) and n-butanol (n-BuOH) solvents. 1D and 2D-Nuclear Magnetic Resonance (NMR) spectra of the EtOAc residue are shown in Figures S1–S4, Supplementary Materials
Summary
Natural Products (NPs) continue to be the major source for drug leads, providing unique structurally diverse chemical scaffolds [1]. In the chemistry of NPs, Nuclear Magnetic Resonance (NMR) turns out to be an indispensable tool in the process of screening crude plant extracts for bioactive metabolites [2]. Plant extracts consist of unique and convoluted mixtures of bioactive NPs with complicated and unpredicted spectral patterns. The constantly increasing demand for mountain tea results in serious concerns about the survival of the wild Sideritis populations due to their overharvesting. The cultivation of Sideritis species has been viewed as a dynamic solution that could contribute to reducing the extensive collection (or overharvesting) and the potential extinction of the natural wild populations, to produce raw materials in sufficient quantities for the industrial-scale production demanded, and most importantly, to affirm for high quality and standardized products
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