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Processes 2019, 7(4), 208; https://doi.org/10.3390/pr7040208

Benzoic Acid Derivatives of Ifloga spicata (Forssk.) Sch.Bip. as Potential Anti-Leishmanial against Leishmania tropica

1
Department of Pharmacy, University of Malakand, Chakdara, Khyber Pakhtunkhwa 18800, Pakistan
2
Department of Pharmacy, Kohat University of Science & Technology, Kohat 26000, Pakistan
3
Department of Chemistry, Kohat University of Science & Technology, Kohat 26000, Pakistan
4
Faculty of Pharmacy, Universiti Teknologi MARA Puncak Alam Campus, Bandar Puncak Alam, Selangor 42300, Malaysia
5
Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA Puncak Alam Campus, Bandar Puncak Alam, Selangor 42300, Malaysia
6
Department of Biotechnology Abdul Wali Khan University, Mardan 23200, Pakistan
7
Suleiman Bin Abdullah Aba-Alkhail center for Interdisciplinary Research in Basic Sciences, International Islamic University, Islamabad 46000, Pakistan
8
Institute of Integrative Biosciences IIB, CECOS University, Peshawar 25000, Pakistan
*
Authors to whom correspondence should be addressed.
Received: 23 February 2019 / Revised: 1 April 2019 / Accepted: 4 April 2019 / Published: 11 April 2019
(This article belongs to the Special Issue Extraction, Characterization and Pharmacology of Natural Products)
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Abstract

This study aimed to appraise the anti-leishmanial potentials of benzoic acid derivatives, including methyl 3,4-dihydroxybenzoate (compound 1) and octadecyl benzoate (compound 2), isolated from the ethnomedicinally important plant Ifloga spicata (I. spicata). Chemical structures were elucidated via FT-IR, mass spectrometry, and multinuclear (1H and 13C) NMR spectroscopy. Anti-leishmanial potentials of the compounds were assessed using Leishmania tropica promastigotes. Moreover, acridine orange fluorescent staining was performed to visualize the apoptosis-associated changes in promastigotes under a fluorescent microscope. A SYTOX assay was used to check rupturing of Leishmania promastigote cell membranes using 0.1% Triton X-100 as positive control. A DNA interaction assay was carried out to assess DNA attachment potential. AutoDock software was used to check the binding affinity of compounds with surface enzyme leishmanolysin gp63 (1LML). Both compounds exhibited considerable anti-leishmanial potential, with LD50 values of 10.40 ± 0.09 and 14.11 ± 0.11 μg/mL for compound 1 and compound 2, respectively. Both compounds showed higher binding affinity with the leishmanolysin (gp63) receptor/protease of Leishmania, as assessed using computational analysis. The binding scores of compounds 1 and 2 with target gp63 were −5.3 and −5.6, respectively. The attachment of compounds with this receptor resulted in their entry into the cell where they bound with Leishmania DNA, causing apoptosis. The results confirmed that the investigated compounds have anti-leishmanial potential and are potential substitutes as natural anti-leishmanial agents against L. tropica. View Full-Text
Keywords: Ifloga spicata; benzoic acid derivatives; Leishmania tropica; docking; DNA interaction; apoptosis Ifloga spicata; benzoic acid derivatives; Leishmania tropica; docking; DNA interaction; apoptosis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Shah, S.M.; Ullah, F.; Ayaz, M.; Sadiq, A.; Hussain, S.; Ali Shah, A.-U.-H.; Shah, S.A.A.; Ullah, N.; Ullah, F.; Ullah, I.; Nadhman, A. Benzoic Acid Derivatives of Ifloga spicata (Forssk.) Sch.Bip. as Potential Anti-Leishmanial against Leishmania tropica. Processes 2019, 7, 208.

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