GC-MS metabolites profiling of anethole-rich oils by different extraction techniques: antioxidant, cytotoxicity and in-silico enzymes inhibitory insights

Dina M El-Kersh; Nada M Mostafa; Shaimaa Fayez; Tarfah Al-Warhi; Mohammed A S Abourehab; Wagdy M Eldehna; Mohamed A Salem

doi:10.1080/14756366.2022.2097445

GC-MS metabolites profiling of anethole-rich oils by different extraction techniques: antioxidant, cytotoxicity and in-silico enzymes inhibitory insights

J Enzyme Inhib Med Chem. 2022 Dec;37(1):1974-1986. doi: 10.1080/14756366.2022.2097445.

Authors

Dina M El-Kersh¹, Nada M Mostafa², Shaimaa Fayez², Tarfah Al-Warhi³, Mohammed A S Abourehab⁴, Wagdy M Eldehna^{5

6}, Mohamed A Salem⁷

Affiliations

¹ Department of Pharmacognosy, Faculty of Pharmacy, The British University in Egypt (BUE), Cairo, Egypt.
² Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, Egypt.
³ Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.
⁴ Department of Pharmaceutics Faculty of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia.
⁵ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, Egypt.
⁶ School of Biotechnology, Badr University in Cairo, Badr City, Cairo, Egypt.
⁷ Department of Pharmacognosy and Natural products, Faculty of Pharmacy, Menoufia University, Menoufia, Egypt.

Abstract

GC-MS profiling and metabolomics study of anise and star anise oils obtained by hydrodistillation, n-hexane, and microwave-assisted extraction methods were conducted herein. Trans-anethole was the major phenylpropanoid in both oils. Principal component and hierarchical cluster analyses revealed a clear separation of different extraction methods. Microwave-assisted star anise oil (MSA) revealed the highest anethole content (93.78%). MSA oil showed antioxidant activity using DPPH and ABTS assays, this was verified via an in-silico docking study of its major compounds on human tyrosinase and NAD(P)H oxidase. Trans-anethole displayed the best fitting scores (-8.9 and -10.1 Kcal/mole, respectively). MSA oil showed promising cytotoxic activity on different cell lines, mainly the cervical (HeLa) cell lines. Cell cycle inhibition at the G0-G1 phase was observed with an early apoptotic effect of the oil on HeLa cells. Trans-anethole achieved the best docking scores (-7.9, -9.3 and -9.9 Kcal/mole) for in-silico study on EGFR, CDK2 and CDK4 enzymes engaged in cancer, respectively.

Keywords: Essential oils; GC-MS profiling; antioxidant; cytotoxicity activity; in-silico study; metabolomics.

MeSH terms

Allylbenzene Derivatives
Anisoles
Antioxidants* / pharmacology
Gas Chromatography-Mass Spectrometry
HeLa Cells
Humans
Oils, Volatile* / chemistry

Substances

Allylbenzene Derivatives
Anisoles
Antioxidants
Oils, Volatile
anethole

Grants and funding

The authors extend their appreciation to the Princess Nourah bint Abdulrahman University Researchers Supporting Project number (PNURSP2022R25), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia. “The authors would like to thank the Deanship of Scientific Research at Umm Al-Qura University for supporting this work by Grant Code: (22UQU4290565DSR39), maabourehab@uqu.edu.sa”.