HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

Emira Noumi^{1

2}, Mejdi Snoussi^{1

3}, El Hassane Anouar⁴, Mousa Alreshidi¹, Vajid N Veettil¹, Salem Elkahoui^{1

5}, Mohd Adnan¹, Mitesh Patel⁶, Adel Kadri^{7

8}, Kaïss Aouadi^{9

10}, Vincenzo De Feo¹¹, Riadh Badraoui^{1

12

13}

Affiliations

¹ Department of Biology, College of Science, University of Hail, P.O. Box 2440, Ha'il 2440, Saudi Arabia.
² Laboratory of Bioressources: Integrative Biology and Recovery, High Institute of Biotechnology-University of Monastir, Monastir 5000, Tunisia.
³ Laboratory of Genetics, Biodiversity and Valorisation of Bioressources, High Institute of Biotechnology-University of Monastir, Monastir 5000, Tunisia.
⁴ Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia.
⁵ Laboratory of Bioactive Substances, Center of Biotechnology of Borj Cedria, BP 901, Hammam lif 2050, Tunisia.
⁶ Bapalal Vaidya Botanical Research Centre, Department of Biosciences, Veer Narmad South Gujarat University, Surat 395007, India.
⁷ Department of Chemistry, College of Science and Arts in Baljurashi, Albaha University, Albaha 65527, Saudi Arabia.
⁸ Department of Chemistry, Faculty of Science of Sfax, University of Sfax, BP 1117, Sfax 3000, Tunisia.
⁹ Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.
¹⁰ Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia.
¹¹ Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 132, Fisciano, 84084 Salerno, Italy.
¹² Section of Histology-Cytology, Medicine College of Tunis, Tunis El Manar University, Road Djebel Lakhdhar, La Rabta-Tunis 1007, Tunisia.
¹³ Laboratory of Histo-Embryology and Cytogenetic, Medicine College of Sfax, Sfax University, Sfax 3029, Tunisia.

PMID: 33167507
PMCID: PMC7694502
DOI: 10.3390/antiox9111089

HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

Emira Noumi et al. Antioxidants (Basel). 2020.

. 2020 Nov 5;9(11):1089.

doi: 10.3390/antiox9111089.

Authors

Affiliations

¹ Department of Biology, College of Science, University of Hail, P.O. Box 2440, Ha'il 2440, Saudi Arabia.
² Laboratory of Bioressources: Integrative Biology and Recovery, High Institute of Biotechnology-University of Monastir, Monastir 5000, Tunisia.
³ Laboratory of Genetics, Biodiversity and Valorisation of Bioressources, High Institute of Biotechnology-University of Monastir, Monastir 5000, Tunisia.
⁴ Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia.
⁵ Laboratory of Bioactive Substances, Center of Biotechnology of Borj Cedria, BP 901, Hammam lif 2050, Tunisia.
⁶ Bapalal Vaidya Botanical Research Centre, Department of Biosciences, Veer Narmad South Gujarat University, Surat 395007, India.
⁷ Department of Chemistry, College of Science and Arts in Baljurashi, Albaha University, Albaha 65527, Saudi Arabia.
⁸ Department of Chemistry, Faculty of Science of Sfax, University of Sfax, BP 1117, Sfax 3000, Tunisia.
⁹ Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.
¹⁰ Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia.
¹¹ Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 132, Fisciano, 84084 Salerno, Italy.
¹² Section of Histology-Cytology, Medicine College of Tunis, Tunis El Manar University, Road Djebel Lakhdhar, La Rabta-Tunis 1007, Tunisia.
¹³ Laboratory of Histo-Embryology and Cytogenetic, Medicine College of Sfax, Sfax University, Sfax 3029, Tunisia.

PMID: 33167507
PMCID: PMC7694502
DOI: 10.3390/antiox9111089

Abstract

In this study, we investigate the phytochemical profile, anticancer, and antioxidant activities of Teucrium polium methanolic extract using both in vitro and in silico approaches. The results showed the identification of 29 phytochemical compounds belonging to 13 classes of compounds and 20 tripeptides using High Resolution-Liquid Chromatography Mass Spectrometry (HR-LCMS). 13R-hydroxy-9E,11Z octadecadienoic acid, dihydrosamidin, valtratum, and cepharantine were the main compounds identified. The tested extract showed promising antioxidant activities (ABTS-IC₅₀ = 0.042 mg/mL; 1,1-diphenyl-2-picrylhydrazyl (DPPH)-IC₅₀ = 0.087 mg/mL, β-carotene-IC₅₀ = 0.101 mg/mL and FRAP-IC₅₀ = 0.292 mg/mL). Using both malignant Walker 256/B and MatLyLu cell lines, T. polium methanolic extract showed a dose/time-dependent antitumor activity. The molecular docking approach revealed that most of the identified molecules were specifically binding with human peroxiredoxin 5, human androgen, and human progesterone receptors with high binding affinity scores. The obtained results confirmed that T. polium is a rich source of bioactive molecules with antioxidant and antitumor potential.

Keywords: HR-LCMS; MatLyLu; Teucrium polium L.; Walker 256/B; anticancer; antioxidant; molecular docking; phytochemistry.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

**Figure 1**
Vegetative growth (a), budding (b), and full bloom (c) of *T. polium* collected from Hail region.

**Figure 2**
Chemical structures of the most dominant identified compounds in *T. polium* methanolic extract by using High Resolution-Liquid Chromatography Mass Spectrometry (HR-LCMS). (A). 13R-hydroxy-9E,11Z-octadecadienoic acid, (B). Rhoifolin, (C). Sericetin diacetate, (D). Selinidin, (E). Harpagoside, (F). Valtratum, (G). Triptonide, (H). Koparin 2′-Methyl Ether, (I). Dihydrosamidin (J). 10S,11R-Epoxy-punaglandin, (K). 4, 16alpha, 17beta-Estriol 3-(beta-D-glucuronide), (L). Khayanthone. (M). 10-Hydroxyloganin, (N). 7-Epiloganin tetraacetate, (O). Cepharanthine, (P). Deoxyloganin tetraacetate, (Q). Carapin-8 (9)-Ene, (R). 1-dodecanoyl-sn-glycerol.

**Figure 3**
Anticancer effect of *T. polium* methanolic extract on malignant Walker 256/B mammary gland carcinoma cells (White) and MatLyLu prostate cancer cells (gray) in 24 (A) and 48 h (B). Legend: * p < 0.05, ** p < 0.01, *** p < 0.001.

**Figure 4**
Three-dimensional (**right**) and two-dimensional (**left**) closest interactions between active site residues of peroxiredoxin 5 and some molecules belonging to different class compounds with the best score result. Legend: (A): Compound 13 (CMP-N-acetylneuraminic acid, Class: Amino Sugar), (B): Compound 14 (Carapin-8 (9)-Ene, Class: Limnoid), (C): Compound 10 (Sericetin diacetate, Class: Flavonol), and (D): Compound 8 (Cepharantine, Class: Alkaloid).

**Figure 5**
Three-dimensional (**right**) and two-dimensional (**left**) closest interactions between active site residues of the human progesterone receptor and some molecules belonging to different class compounds with the best score result. Legend: (A): Compound 8 (Cepharantine, Class: Alkaloid), (B): Compound 20 (Triptonide, Class: Diterpene triepoxide), (C): Compound 10 (Sericetin diacetate, Class: Flavonol), (D): Compound 24 (16alpha,17beta-Estriol 3-(beta-D-glucuronide, Class: Steroidal glycosides), (E): Compound 14 (Carapin-8 (9)-Ene, Class: Limnoid), (F): Compound 28 (Khayanthone, Class: Limnoid).

**Figure 6**
Three-dimensional (**right**) and 2D **(left**) closest interactions between the active site residues of the human androgen and some molecules belonging to different class compounds with the best score result. Legend: (A): Compound 15 (Selinidin, Class: coumarin derivative), (B): Compound 18 (larixol acetate), (C): Compound 19 (Valtratum, Class: Terpene) and (D): Compound 22 (dihydrosamidin, Class: coumarins).

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HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

Affiliations

HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

Authors

Affiliations

Abstract

Conflict of interest statement

Figures

References

Grants and funding

LinkOut - more resources

Full Text Sources

Miscellaneous