In Silico, Cytotoxic and Antioxidant Potential of Novel Ester, 3-hydroxyoctyl -5- trans-docosenoate Isolated from Anchusa arvensis (L.) M.Bieb. Against HepG-2 Cancer Cells

Abstract

Background

Cancer is one of the chronic health conditions worldwide. Various therapeutically active compounds from medicinal plants were the current focus of this research in order to uncover a treatment regimen for cancer. Anchusa arvensis (A. anchusa) (L.) M.Bieb. contains many biologically active compounds.

Methods

In the current study, new ester 3-hydroxyoctyl -5- trans-docosenoate (compound-1) was isolated from the chloroform soluble fraction of A. anchusa using column chromatography. Using MTT assay, the anticancer effect of the compound was determined in human hepatocellular carcinoma cells (HepG-2) compared with normal epithelial cell line (Vero). DPPH and ABTS radical scavenging assays were performed to assess the antioxidant potential. The Molecular Operating Environment (MOE-2016) tool was used against tyrosine kinase.

Results

The structure of the compound was elucidated based on IR, EI, and NMR spectroscopy technique. It exhibited a considerable cytotoxic effect against HepG-2 cell lines with IC₅₀ value of 6.50 ± 0.70 µg/mL in comparison to positive control (doxorubicin) which showed IC₅₀ value of 1.3±0.21 µg/mL. The compound did not show a cytotoxic effect against normal epithelial cell line (Vero). The compound also exhibited significant DPHH scavenging ability with IC₅₀ value of 12 ± 0.80 µg/mL, whereas ascorbic acid, used as positive control, demonstrated activity with IC₅₀ = 05 ± 0.15 µg/mL. Similarly, it showed ABTS radical scavenging ability (IC₅₀ = 130 ± 0.20 µg/mL) compared with the value obtained for ascorbic acid (06 ± 0.85 µg/mL). In docking studies using MOE-2016 tool, it was observed that compound-1 was highly bound to tyrosine kinase by having two hydrogen bonds at the hinge region. This good bonding network by the compound might be one of the reasons for showing significant activity against this enzyme.

Conclusion

Our findings led to the isolation of a new compound from A. anchusa which has significant cytotoxic activity against HepG-2 cell lines with marked antioxidant potential.

Keywords:

• cancer
• Anchusa arvensis
• 3-hydroxyoctyl-5
• trans-docosenoate
• cytotoxicity against HepG-2 cell lines
• antioxidant

Acknowledgments

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through research group no RGP-262. The authors are also thankful to the Department of Pharmacy, University of Malakand, for provision of a laboratory.

Abbreviations

MTT, 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazolium bromide; A. arvensis, Anchusa arvensis; TKs, tyrosine kinases; DMSO, dimethyl sulfoxide.

Author Contributions

SH, FU, WA, and RU performed experimental work and data collection. Data were evaluated by MA, AAS, and SAAS. Computational studies were performed by AW. MA, SH and SMS were involved in literature search and manuscript preparation. MA, SH and refined the manuscript for publication. AAS, RU, and FAN financially supported the research work. All authors contributed to data analysis, drafting and revising the article, gave final approval of the version to be published, and agree to be accountable for all aspects of the work.

Disclosure

The authors report no conflicts of interest in this work.