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Chemical and Biological Insights on Phaulopsis falcisepala: A Source of Bioactive Compounds with Multifunctional Anticancer Potentials

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Abstract

In spite of remarkable progress and success made in anticancer research, major challenges in treatment of cancer remain recurrence of tumour and adverse effects of anticancer drugs. The search for novel, effective and safe anticancer agents, therefore remains important. This study investigated the chemical constituents of Phaulopsis falcisepala, a plant used in ethnomedicine to treat cancer; and evaluated anticancer and drug-likeness potentials of the constituents against selected non-small cell lung cancer (NSCLC), breast cancer, and chronic myelogenous leukemia (CML) targets. Lupeol and a mixture of stigmasterol and β-sitosterol were isolated from P. falcisepala and characterized using NMR, MS and IR data. Additional fifteen compounds, including piperine, piperanine, feruloyltyramine, asperglaucide and 6,7-dihydroflavopereirine were putatively identified in the plant by analysis of its MS/MS data against tandem MS/MS data repository using the Global Natural Products Social Molecular Networking tool (GNPS). Using molecular docking, stigmasterol (‒ 7.8 to ‒ 10.1 Kcal/mol), β-sitosterol (‒7.0 to ‒ 9.9 Kcal/mol), and lupeol (‒ 8.2 to ‒ 9.2 Kcal/mol) showed considerable binding affinities against non-small cell lung cancer and breast cancer molecular targets when compared to the reference inhibitors (‒ 8.4 to ‒ 10.8 Kcal/mol). Piperine (‒ 8.5 to ‒ 9.8 Kcal/mol), piperanine (‒ 8.5 to ‒ 9.6 Kcal/mol), and 6,7-dihydroflavopereirine (‒ 8.0 to ‒ 10.2 Kcal/mol) exerted good interactions with the active site, allosteric site and mutant form of BCR-ABL, an important target in chronic myelogenous leukemia. Many of the compounds in P. falcisepala were shown to possess fair to favourable drug likeness and ADME properties. However, lupeol, stigmasterol and β-sitosterol were predicted to have poor oral absorption.

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Acknowledgements

The authors appreciate the Department of Chemistry, Nelson Mandela University for the provision of facilities for isolating and elucidating the structures of compounds and the Département de Pharmacognosie, Faculté de Pharmacie, Université Paris-Saclay for the facilities for the UPLC-HRMS/MS analysis.

Funding

This study was supported by Tertiary Education Trust Fund (TETFUND) under Grant: DR&D/CE/NRF/STI/70/VOL.I and Royal Society of Chemistry (RSC) under Grant: R20-4483.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Lagos, CMUL Campus, Idi-araba, Lagos, Nigeria

    Akolade R. Oladipupo, Stephenie Chinwe Ama Alaribe, Celina O. Ogah & Herbert A. B. Coker

  2. Department of Chemistry, Nelson Mandela University, P.O. Box 77000, Port Elizabeth, 6031, South Africa

    Adeniyi S. Ogunlaja

  3. Equipe Chimie des Substances Naturelles, BioCIS, Université Paris-Saclay, CNRS, 92290, Châtenay-Malabry, France

    Mehdi A. Beniddir

  4. Department of Cell Biology and Genetics, Faculty of Science, University of Lagos, Akoka, Yaba, Lagos, Nigeria

    Joy Okpuzor

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Oladipupo, A.R., Alaribe, S.C.A., Ogunlaja, A.S. et al. Chemical and Biological Insights on Phaulopsis falcisepala: A Source of Bioactive Compounds with Multifunctional Anticancer Potentials. Chemistry Africa 6, 1175–1189 (2023). https://doi.org/10.1007/s42250-022-00553-8

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