Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile

Authors

  • Kristina Mihajlovic University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovića 12, 34000 Kragujevac, Serbia
  • Vera M Divac University of Kragujevac, Faculty of Science, Department of Chemistry
  • Marina Kostic University of Kragujevac, Institute for Information Technologies, Department of Science, Jovana Cvijica bb, 34000 Kragujevac, Serbia.
  • Marko Zivanovic University of Kragujevac, Institute for Information Technologies, Department of Science, Jovana Cvijica bb, 34000 Kragujevac, Serbia.
  • Jelena Grujic University of Kragujevac, Institute for Information Technologies, Department of Science, Jovana Cvijica bb, 34000 Kragujevac, Serbia.
  • Katarina Virijevic University of Kragujevac, Institute for Information Technologies, Department of Science, Jovana Cvijica bb, 34000 Kragujevac, Serbia.

DOI:

https://doi.org/10.20450/mjcce.2022.2499

Keywords:

terpenic alcohols, selenium, cyclic ethers, cytotoxicity, redox status

Abstract

Terpenic alcohols linalool, nerolidol and α-terpineol were subjected to the PhSe-induced cyclization, where corresponding cyclic ethers were obtained. The heterocyclic product derived from α-terpineol is a derivate of the natural product eucalyptol, while linalool cyclization produces precursors of the natural product karahanaenone. All three cyclic ether products have an organoselenium moiety in the side chain, which can represent a significant source of bioactivities. Biological evaluation of obtained products, in vitro cytotoxicity and redox status parameters, was performed on two model systems: HCT-116 – immortalized colon cancer cell line, and MRC-5 – healthy fibroblasts isolated from lung pleura. The results indicate a strong prooxidative character of all compounds on colon cancer HCT-116 and healthy MRC-5 cells in the highest applied concentrations. Selectivity towards cancer cells was not observed, except when nerolidol-derived product was used for longer exposure time. A biological evaluation was conducted to establish the quantitative relationship between enhanced radical species formation and cell viability.

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Published

2022-06-12 — Updated on 2022-07-01

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How to Cite

Mihajlovic, K., Divac, V. M., Kostic, M., Zivanovic, M., Grujic, J., & Virijevic, K. (2022). Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile. Macedonian Journal of Chemistry and Chemical Engineering, 41(1), 89–98. https://doi.org/10.20450/mjcce.2022.2499 (Original work published June 12, 2022)

Issue

Vol. 41 No. 1 (2022)

Section

Natural Products

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Copyright (c) 2022 Kristina Mihajlovic, Vera M Divac, Marina Kostic, Marko Zivanovic, Jelena Grujic, Katarina Virijevic

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