Skip to main content
Log in

α-Glucosidase Inhibitors from Marrubium astracanicum: Isolation and Molecular Docking

  • Original Article
  • Published:
Revista Brasileira de Farmacognosia Aims and scope Submit manuscript

Abstract

Marrubium astracanicum Jacq., Lamiaceae, is an herbaceous plant distributed in Iran, Turkey, and southern Caucasia. In the present study, α-glucosidase inhibitory principles of M. astracanicum aerial parts were investigated by a bioassay-guided approach. The extraction procedure from the plant aerial parts was carried out successively using petroleum ether, ethyl acetate, and methanol. The ethyl acetate extract, with the highest in vitro α-glucosidase inhibitory activity, was subjected to further chemical investigation. The structures of the isolated compounds were elucidated by 1H-NMR and 13C-NMR spectral analyses as apigenin-7-O-(3′′-(E)-p-coumaroyl)-β-d-glucoside, apigenin-7-O-(6′′-(E)-p-coumaroyl)-β-d-glucoside, martynoside, apigenin-7-O-β-d-glucoside, and verbascoside. In addition, the antidiabetic potential of the isolated compounds was evaluated in an in vitro α-glucosidase inhibitory assay, and kinetic and molecular docking studies were done for the most active compound. Apigenin-7-O-(3′′-(E)-p-coumaroyl)-β-d-glucoside and apigenin-7-O-(6′′-(E)-p-coumaroyl)-β-d-glucoside showed the most potent in vitro α-glucosidase inhibitory activity with IC50 values of 57.4 ± 1.2 and 186.4 ± 2.5 μM, respectively, which was about 4 to 13 times lower than the IC50 value of the reference compound acarbose (751.2 ± 0.4 μM).

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

Download references

Funding

This research was supported by Tehran University of Medical Sciences and Health Services Grants (No. 99-1-104-48267).

Author information

Authors and Affiliations

Authors

Contributions

RK and AH carried out the phytochemical analysis. MRD and MK supervised this study and suggested the original idea. MRD also has participated in interpreting related spectra and writing the manuscript. MAF and SM have contributed to enzyme inhibition assay. HPK conducted the molecular docking study. The current manuscript was critically read and approved by all authors.

Corresponding authors

Correspondence to Mohammad-Reza Delnavazi or Mahnaz Khanavi.

Supplementary Information

ESM 1

(PDF 1281 kb)

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kazemi, R., Delnavazi, MR., Parsa-Khankandi, H. et al. α-Glucosidase Inhibitors from Marrubium astracanicum: Isolation and Molecular Docking. Rev. Bras. Farmacogn. 32, 618–626 (2022). https://doi.org/10.1007/s43450-022-00287-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s43450-022-00287-1

Keywords

Navigation