Ailanthus excelsa leaf extract: Chemical characterization, antischistosomal activity, and in silico study of isolated phenolic compounds as promising thioredoxin glutathione reductase inhibitors

Theodor Bilharz Research Institute

Bibliographic Information

Authors: Mohammed H.S.; William S.; Aboushousha T.; Taleb H.M.A.; Sabour R.; Ghareeb M.A.

Journal: Journal of Applied Pharmaceutical Science

Publisher: Open Science Publishers LLP Inc.

Publication Date: 1 February 2023

Volume / Issue: Volume 13 / Issue 2

Pages: 124–145

ISSN: 22313354

DOI: 10.7324/JAPS.2023.130215

Scopus: View on Scopus

Document Type: Article

Access: All Open Access; Gold Open Access

Authors and Affiliations

Mohammed H.S., Department of Pharmacognosy and Medicinal Plants, Faculty of Pharmacy (Girls), Al-Azhar University, Cairo, Egypt; William S., Department of Parasitology, Theodor Bilharz Research Institute, Giza, Egypt; Aboushousha T., Department of Pathology, Theodor Bilharz Research Institute, Giza, Egypt; Taleb H.M.A., Department of Environmental Research, Theodor Bilharz Research Institute, Giza, Egypt; Sabour R., Department of Medicinal Pharmaceutical Chemistry and Drug Design, Faculty of Pharmacy (Girls), Al-Azhar University, Cairo, Egypt; Ghareeb M.A., Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Egypt

Abstract

Hepatic schistosomiasis is the most well-known chronic condition, with a variety of clinical symptoms. In the current study, the metabolite profile of the Ailanthus excelsa leaf butanol extract was investigated using chromatographic isolation and Liquid chromatography electrospray ionization /mass spectrometry (LC-ESI-MS/MS) analysis. Also, its schistosomicidal effect was examined in vivo regarding disease progression in a comparative experimental study to praziquantel (PZQ). The parasitological parameters (total worm burden, tissue egg load, and oogram pattern) of the infected and the treated mice were counted. A histopathological examination of the liver granuloma took place as well. The extract (at a dose of 500 mg/kg) caused a significant worm reduction of 41.30% and also a significant reduction in intestinal egg load (6.36 ± 1.12 vs. 17.82 ± 2,024.6). Data also showed a reduction in immature eggs in the extract group (33.00 ± 2.45 vs. 57.4 ± 3.89) when compared to the infected untreated group. Five phenolic compounds were isolated and identified as gallic acid (1), methyl gallate (2), quercitrin (3), isoquercitrin (4), and kaempferin (5). Furthermore, molecular docking was utilized for the first time to evaluate the efficacy of the isolated compounds (1–5) in disrupting the essential worm enzyme thioredoxin glutathione reductase. Compounds 3–5 showed high docking scores ranging from −7.054 to −11.370 kcal/mol that were comparable to that of PZQ (−6.407 kcal/mol). Moreover, LC-ESI-MS/MS profiling led to the identification of 33 secondary metabolites. These compounds were classified as phenolic acids, flavonoids, iridoids, stilbenoids, chalcones, tannins, and coumarins. The findings suggest that the A. excelsa leaf extract could be used as a naturally occurring antischistosomal agent and this emphasizes the significance of phenolic components. © 2023 Hala Sh. Mohammed et al. This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/).

Keywords

Ailanthus excelsa; antischistosomal activity; docking; LC-ESI-MS/ MS; polyphenolics; TGR; 3,4,5 trihydroxy benzoic acid; Ailanthus excelsa extract; antischistosomal agent; benzoic acid derivative; butanol; chalcone derivative; coumarin derivative; flavonoid; gallic acid; gallic acid methyl ester; iridoid; isoquercetin; kaempferol 3 o alpha l rhamnopyranoside; methyl 3,4,5 trihydroxy benzoate; oxidoreductase inhibitor; phenol; plant extract; plant medicinal product; praziquantel; quercetin 3 o alpha l rhamnopyranoside; quercetin 3 o beta d glucopyranoside; quercitrin; tannin derivative; thioredoxin glutathione reductase inhibitor; unclassified drug; animal experiment; animal model; animal tissue; antiparasitic activity; Article; carbon nuclear magnetic resonance; chemical analysis; chemical structure; column chromatography; computer model; controlled study; egg size; electrospray mass spectrometry; experimental schistosomiasis mansoni; fibrosis; histopathology; hydrogen bond; in vivo study; inflammation; liquid chromatography-mass spectrometry; liver granuloma; male; molecular docking; mouse; nonhuman; oocyte development; oogram pattern; paper chromatography; parasite egg count; parasitological parameters; plant leaf; polyamide column chromatography; proton nuclear magnetic resonance; retention time (chromatography); thin layer chromatography; tissue egg load; total worm burden

Citation Information

Scopus Citations: 7

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