In Vitro and In Silico Evaluation of Anticholinesterase and Antidiabetic Effects of Furanolabdanes and Other Constituents from Graptophyllum pictum (Linn.) Griffith
-
Published:2023-06-16
Issue:12
Volume:28
Page:4802
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Metiefeng Nathalie Tanko1, Tamfu Alfred Ngenge234ORCID, Fotsing Tagatsing Maurice1, Tabopda Turibio Kuiate1, Kucukaydin Selcuk3ORCID, Noah Mbane Martin1ORCID, de Theodore Atchade Alex1, Talla Emmanuel2, Henoumont Celine5ORCID, Laurent Sophie5ORCID, Anouar El Hassane6ORCID, Dinica Rodica Mihaela4ORCID
Affiliation:
1. Department of Organic Chemistry, Faculty of Science, The University of Yaounde I, Yaounde 812, Cameroon 2. Department of Chemical Engineering, School of Chemical Engineering and Mineral Industries, University of Ngaoundere, Ngaoundere 454, Cameroon 3. Department of Medical Services and Techniques, Koycegiz Vocational School of Health Services, Mugla Sitki Kocman University, Mugla 48800, Turkey 4. Department of Chemistry, Physics and Environment, Faculty of Sciences and Environment, ‘Dunarea de Jos’ University of Galati, 47 Domneasca Str., 800008 Galati, Romania 5. Laboratory of NMR and Molecular Imaging, Department of General, Organic and Biomedical Chemistry, University of Mons, B-7000 Mons, Belgium 6. Department of Chemistry, College of Sciences and Humanities in Al-Kharj, Prince Sattam bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia
Abstract
Graptophyllum pictum is a tropical plant noticeable for its variegated leaves and exploited for various medicinal purposes. In this study, seven compounds, including three furanolabdane diterpenoids, i.e., Hypopurin E, Hypopurin A and Hypopurin B, as well as with Lupeol, β-sitosterol 3-O-β-d-glucopyranoside, stigmasterol 3-O-β-d-glucopyranoside and a mixture of β-sitosterol and stigmasterol, were isolated from G. pictum, and their structures were deduced from ESI-TOF-MS, HR-ESI-TOF-MS, 1D and 2D NMR experiments. The compounds were evaluated for their anticholinesterase activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BchE), as well as their antidiabetic potential through inhibition of α-glucosidase and α-amylase. For AChE inhibition, no sample had IC50 within tested concentrations, though the most potent was Hypopurin A, which had a percentage inhibition of 40.18 ± 0.75%, compared to 85.91 ± 0.58% for galantamine, at 100 µg/mL. BChE was more susceptible to the leaves extract (IC50 = 58.21 ± 0.65 µg/mL), stem extract (IC50 = 67.05 ± 0.82 µg/mL), Hypopurin A (IC50 = 58.00 ± 0.90 µg/mL), Hypopurin B (IC50 = 67.05 ± 0.92 µg/mL) and Hypopurin E (IC50 = 86.90 ± 0.76 µg/mL). In the antidiabetic assay, the furanolabdane diterpenoids, lupeol and the extracts had moderate to good activities. Against α-glucosidase, lupeol, Hypopurin E, Hypopurin A and Hypopurin B had appreciable activities but the leaves (IC50 = 48.90 ± 0.17 µg/mL) and stem (IC50 = 45.61 ± 0.56 µg/mL) extracts were more active than the pure compounds. In the α-amylase assay, stem extract (IC50 = 64.47 ± 0.78 µg/mL), Hypopurin A (IC50 = 60.68 ± 0.55 µg/mL) and Hypopurin B (IC50 = 69.51 ± 1.30 µg/mL) had moderate activities compared to the standard acarbose (IC50 = 32.25 ± 0.36 µg/mL). Molecular docking was performed to determine the binding modes and free binding energies of Hypopurin E, Hypopurin A and Hypopurin B in relation to the enzymes and decipher the structure–activity relationship. The results indicated that G. pictum and its compounds could, in general, be used in the development of therapies for Alzheimer’s disease and diabetes.
Funder
‘Dunarea de Jos’ University, Galati, Romania
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference71 articles.
1. Phytochemical screening, antioxidant activity, total polyphenols and flavonoids content of different extracts of propolis from Tekel (Ngaoundal, Adamawa region, Cameroon);Talla;J. Phytopharmacol.,2014 2. Targeting oxidative stress in disease: Promise and limitations of antioxidant therapy;Forman;Nat. Rev. Drug Discov.,2021 3. New mono-ether of glycerol and triterpenes with DPPH radical scavenging activity from Cameroonian propolis;Talla;Nat. Prod. Res.,2017 4. Oxidative stress and antioxidant potential of one hundred medicinal plants;Hassan;Curr. Top. Med. Chem.,2017 5. Phenolic composition, antioxidant and enzyme inhibitory activities of Parkia biglobosa (Jacq.) Benth., Tithonia diversifolia (Hemsl) A. Gray, and Crossopteryx febrifuga (Afzel.) Benth;Tamfu;Arabian J. Chem.,2022
Cited by
2 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
|
|