Antioxidant and Cytotoxic Activity of a New Ferruginan A from Olea ferruginea: In Vitro and In Silico Studies

Zafar Ali Shah; Adil A H Mujawah; Irfan Ullah; Abdur Rauf; Umer Rashid; Anees Ahmed Khalil; Syed Muhammad Mukarram Shah; Aini Pervaiz; Farzana Shaheen; Yahya S Al-Awthan; Muhammad Nasimullah Qureshi; Mohammed A Al-Duais; Omar Bahattab; Zainab M Almarhoon; Yahia N Mabkhot; Mohammad S Mubarak

doi:10.1155/2022/8519250

Antioxidant and Cytotoxic Activity of a New Ferruginan A from Olea ferruginea: In Vitro and In Silico Studies

Oxid Med Cell Longev. 2022 Jan 20:2022:8519250. doi: 10.1155/2022/8519250. eCollection 2022.

Authors

Zafar Ali Shah¹, Adil A H Mujawah², Irfan Ullah¹, Abdur Rauf¹, Umer Rashid³, Anees Ahmed Khalil⁴, Syed Muhammad Mukarram Shah⁵, Aini Pervaiz⁵, Farzana Shaheen⁶, Yahya S Al-Awthan^{7

8}, Muhammad Nasimullah Qureshi¹, Mohammed A Al-Duais^{9

10}, Omar Bahattab⁷, Zainab M Almarhoon¹¹, Yahia N Mabkhot¹², Mohammad S Mubarak¹³

Affiliations

¹ Department of Chemistry, University of Swabi, Swabi, 23561 Khyber Pakhtunkhwa, Pakistan.
² Department of Chemistry, College of Science and Arts, Qassim University, Ar Rass 51921, Saudi Arabia.
³ Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, 22060 Abbottabad, Pakistan.
⁴ University Institute of Diet and Nutritional Sciences, Faculty of Allied Health Sciences, The University of Lahore, Pakistan.
⁵ Department of Pharmacy, University of Swabi, Swabi, 23561 Khyber Pakhtunkhwa, Pakistan.
⁶ H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Kararchi 75270, Pakistan.
⁷ Department of Biology, Faculty of Science, University of Tabuk, Tabuk, Saudi Arabia.
⁸ Department of Biology, Faculty of Science, Ibb University, Ibb, Yemen.
⁹ Department of Biochemistry, Faculty of Science, University of Tabuk, Tabuk, Saudi Arabia.
¹⁰ Biochemistry Unit, Chemistry Department, Faculty of Science, Ibb University, Ibb, Yemen.
¹¹ Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
¹² Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha, Saudi Arabia.
¹³ Department of Chemistry, The University of Jordan, Amman 11942, Jordan.

Abstract

Studies of the ethyl acetate extract bark extract of Olea ferruginea led to the isolation of one new compound Ferruginan A (1) in addition to two known compounds, Ferruginan (2) and cycloolivil (3). Structures of the isolated compounds were confirmed by mass spectrometry (MS) and NMR spectral data. The ethyl acetate fraction and compounds (1-3) were evaluated against breast cancer cell line (MCF-7) and as antioxidants using the free radical scavenging assay. Results revealed that compound 2 exhibits significant antioxidant activity with an IC₅₀ value of 21.74 μg/mL. In addition, the ethyl acetate fraction showed good cytotoxic activity (79.31% inhibition at 250 μg/mL), whereas compounds 1-3 exerted mild cytotoxic activity (IC₅₀ = 8.03-12.01 μg/mL) as compared to the standard (IC₅₀ = 4.41 μg/mL) against MCF-7. Docking studies suggested that antioxidant activity is due to the chelation of compounds with copper present in the active site of tyrosinase. These results suggest that the extract exhibits considerable antioxidant activity, and the isolated compounds exert moderate anticancer activity.

MeSH terms

Antioxidants / chemistry*
Biological Products / chemistry*
Computer Simulation
Humans
In Vitro Techniques
Olea / chemistry*
Plant Extracts / chemistry*

Substances

Antioxidants
Biological Products
Plant Extracts