Antiradical and anti-acethylcholinesterase constituents from the methylene chloride extract of Ganoderma applanatum (Pers.) Pat (Ganodermataceae) and molecular docking study. - 2025
Antiradical and anti-acethylcholinesterase constituents from the methylene chloride extract of Ganoderma applanatum (Pers.) Pat (Ganodermataceae) and molecular docking study.
[en] Alzheimer's disease (AD) is a non-communicable disease with global impact. Inhibitors of acetylcholinesterase (AChE) are suitable therapies for AD. In this work, we report the isolation of antiacetylcholinesterase compounds from the methylene chloride (DCM) extract of the medical fungus Ganoderma applanatum (Pers.) Pat (Ganodermataceae). Chemical evaluation of this extract using chromatographic technics led to the isolation of a (1:1) mixture of ergosterol (1) and stellasterol (2), palmitic acid (3), ganodermanondiol (4), lucidumol B (5) and lupeol (6). Structures of these compounds were determined using spectroscopic analysis such as IR, MS, 1D & 2D NMR and literature. The acetylation reaction has been performed on the mixture (1 + 2) and compound 4, leading to the obtention the mixture of 3-acetyl-ergosterol (7) and 3-acetylstellasterol (8) along with 24-acetyl-ganodermanondiol (9) respectively. Total phenolic content was determined for DCM, Ethyl acetate and n-butanol extracts. To assess their antiradical scavenging potential, DPPH was used as free radical. The Inhibition power of acetylcholinesterase was evaluated in vitro using the Ellman reagent. Amongst all tested extracts, the DCM extract showed the high amount of total phenolic compounds with a value of 133.9512 mg EAG/g EX. The same extract showed a very good antiradical scavenging potential with an IC50 of 0.0021 mg/mL. The mixture (1 + 2) showed the highest antiradical scavenging activity with IC50 of 0.0770 mg/mL. The results obtained demonstrated that the acetylation has reduced the antiradical scavenging potential. Concerning the acetylcholinesterase inhibition power, the DCM extract and the mixture (1 + 2) showed a very good power with an inhibition percentage of 89%. The acetylation has also reduced the activity of the obtained derivative. The results provide insights into the potential efficacy of these compounds as acetylcholinesterase inhibitors. The binding interactions of the isolated and acetylated derivatives against acetylcholinesterase protein (PBP 3i6m) of Torpedo californica were studied using Autodock software. Ergosterol (-11.9 kcal/mol) binds better to the protein biding site through significant pi-sigma interactions.
Research center :
CMMI - Centre de Recherche en Microscopie et Imagerie Médicale
Disciplines :
Public health, health care sciences & services Neurology Physical, chemical, mathematical & earth Sciences: Multidisciplinary, general & others Biochemistry, biophysics & molecular biology
Author, co-author :
Feunaing, Roméo Toko ; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon
Gbaweng Yaya, Joël Abel ; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon ; Centre for Research on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies, Yaounde, Cameroon
Nyemb, Jean Noël ; Department of Refining and Petrochemistry, National Advanced School of Mines and Petroleum Industries, The University of Maroua, Kaele, Cameroon
Bassigue, Noël Issa; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon
Ketsemen, Hervé Landry ; Department of Organic Chemistry, Faculty of Science, The University of Yaounde 1, Yaounde, Cameroon
HENOUMONT, Céline ; Université de Mons - UMONS > Faculté de Médecine et de Pharmacie > Service de Chimie générale, organique et biomédicale
Kandeda, Antoine Kavaye ; Department of Biology and Animal Physiology, Faculty of Science, The University of Yaounde 1, Yaounde, Cameroon
LAURENT, Sophie ; Université de Mons - UMONS > Faculté de Médecine et de Pharmacie > Service de Chimie générale, organique et biomédicale ; Department of Organic Chemistry, Faculty of Science, The University of Yaounde 1, Yaounde, Cameroon
Talla, Emmanuel; Department of Chemistry, Faculty of Science, University of Ngaoundere, Ngaoundere, Cameroon
Language :
English
Title :
Antiradical and anti-acethylcholinesterase constituents from the methylene chloride extract of Ganoderma applanatum (Pers.) Pat (Ganodermataceae) and molecular docking study.
R550 - Institut des Sciences et Technologies de la Santé R100 - Institut des Biosciences
Funders :
International Foundation for Science
Funding text :
The authors are grateful to the International Foundation for Science (IFS) which partially supported this work through the grant number I1-F-6564-1 obtained by Dr. Yaya Gbaweng. Authors also thanks the bioprofiling platform supported by the European Regional Development Fund and the Walloon Region, Belgium.
Anonymous. 2000. Compendium of pharmaceuticals and specialties. 25th ed. Toronto, Canada: Canadian Pharmacists Association.
Basnet BB, Liu L, Bao L, Liu H., 2017. Current and future perspective on antimicrobial and anti–parasitic activities of Ganoderma sp: an update. Mycology. 8(2):111–124. doi:10.1080/21501203.2017.1324529.
Bateman RJ, Xiong C, Benzinger TLS, Fagan AM, Goate A, Fox NC, Marcus DS, Cairns NJ, Xie X, Blazey TM, et al.2012. Clinical and biomarker changes in dominantly inherited Alzheimer’s disease. N Engl J Med. 367(9):795–804. doi:10.1056/NEJMoa1202753.
Brenowitz WD, Hubbard RA, Keene CD, Hawes SE, Longstreth WT, Jr, Woltjer RL, Kukull WA., 2017. Mixed neuropathologies and estimated rates of clinical progression in a large autopsy sample. Alzheimer’s Dementia. 13(6):654–662. doi:10.1016/j.jalz.2016.09.015.
Byard RW, Langlois NEI., 2019. Wandering dementia: a syndrome with forensic implications. J Forensic Sci. 64(2):443–445. doi:10.1111/1556-4029.13885.
Daouda N, Mbaye DM, Gassama A, Lavaud C, Pilard SD., 2017. Determination structurale de triterpenoides isloés des feuilles de Combretum glutinosim Perr. (Combretaceae). Int J Biol Chem Sci. 11:488–498.
Dilip SE, Sonia A, Van DS, Lalith SRG, Ravi LC, Wijesundera L, Anthony LJC, John W, Murray HGM., 2006. Lanostane triterpenoids from the Sri Lankan Basidiomycete Ganoderma applanatum. J Nat Prod. 69(8):1245–1248. doi:10.1021/np0602214.
Elkind MSV., 2010. Infectious burden: a new risk factor and treatment target for atherosclerosis. Infect Disord Drug Targets. 10:84–90.
Farrer LA, Cupples LA, Haines JL, Hyman B, Kukull WA, Mayeux R, Myers RH, Pericak-Vance MA, Risch N, van Duijn CM, et al.1997. Effects of age, sex, and ethnicity on the association between apolipoprotein E genotype and Alzheimer disease: a meta-analysis. JAMA. 278(16):1349–1356. doi:10.1001/jama.1997.03550160069041.
Ferreira J, Santos S, Pereira H., 2020. In vitro screening for acetylcholinesterase inhibition and antioxidant activity of Quercus suber Cork and corkback extracts. Evi-Bas Com Alt Med. 9:220–234.
Fratiglioni L, Ahlbom A, Viitanen M, Winblad B., 1993. Risk factors for late-onset Alzheimer’s disease: a population-based, casecontrol study. Ann Neurol. 33(3):258–266. doi:10.1002/ana.410330306.
Ge F-H, Duan M-H, Li J, Shi Q-L., 2017. Ganoderin A, a novel 9,11-secosterol from Ganoderma lucidum spores oil. J Asian Nat Prod Res. 19(12):1252–1257. doi:10.1080/10286020.2017.1313834.
Green RC, Cupples LA, Go R, Benke KS, Edeki T, Griffith PA, Williams M, Hipps Y, Graff-Radford N, Bachman D, et al.2002. Risk of dementia among white and African American relatives of patients with Alzheimer disease. JAMA. 287(3):329–336. doi:10.1001/jama.287.3.329.
Hai-Guo S, Qian W, Lin Z, Xing-Rong P, Wen-Yong X, Ming-Hua Q., 2021. Functional triterpenoids from medical fungi Ganoderma applanatum: a continnuous search for antiadipogeneic agents. Biorg Chem. 112:104977.
Hatami T, Emami SA, Miraghaee SS, Mojarrab, MJI., 2014. Total phenolic contents and antioxidant activities of different extracts and fractions from the aerial parts of Artemisia biennis Willd. Ir J Pharmaceut Res. 13:551.
Hebert LE, Bienias JL, Aggarwal NT, Wilson RS, Bennett DA, Shah RC, Evans DA., 2010. Change in risk of Alzheimer disease over time. Neurology. 75(9):786–791.,. doi:10.1212/WNL.0b013e3181f0754f.
Hoang VT, Nguyen TT, Tuan NN, Doan MD, Tran DT., 2018. The triterpenoid and steroid from the fruiting body of Ganoderma applanatum (Pers.) Pat. In Vietnam. Viet J Sci Technol. 56:5050–5556.
Howes MJR, Perry NSL, Houghton PJ., 2003. Plants with traditional uses and activities, relevant to the management of Alzheimer’s disease and other cognitive disorders. Phytother Res. 17(1):1–18. doi:10.1002/ptr.1280.
Jack CR, Lowe VJ, Weigand SD, Wiste HJ, Senjem ML, Knopman DS, Shiung MM, Gunter JL, Boeve BF, Kemp BJ, et al.2009. Serial PiB and MRI in normal, mild cognitive impairment and Alzheimer’s disease: implications for sequence of pathological events in Alzheimer’s disease. Brain. 132(Pt 5):1355–1365. doi:10.1093/brain/awp062.
Katarzyna SZ, Balik M, Szczepkowski A, Trepa M, Zengin G, Kała K, Muszyńska B., 2023. A review of chemical composition and bioactivity studies of the most promising species of Ganoderma spp. Diversity. 15(8):882. doi:10.3390/d15080882.
Khalilova GA, Turaev AS, Mulkhitdinov BI, Khaitmetova SB, Normakhamatov NS., 2022. Cytotoxic effects and antitumor activity of polysaccharides isolated from the fruiting body of Ganoderma lucidum basidial mushroom. Pharm Chem J. 56(8):1045–1048. doi:10.1007/s11094-022-02750-8.
Ma J, Liu C, Chen Y, Jiang J, Qin Z., 2011. Cellular and molecular mechanisms of the Ganoderma applanatum extracts induces apoptosis on SGC–7901 gastric cancer cells. Cell Biochem Funct. 29(3):175–182. doi:10.1002/cbf.1735.
Mahamat A, Nyemb JN, Gade IS, Talla E, Laurent S, Mbafor JT., 2021. Leptadeniamide, a new ceramide from Leptadenia hastata Pers. (Decne) (Asclepiadeceae) and antimicrobial activity. Intern J Chem Scie. 5(2):01–05.
Min B, Nakamura N, Miyashiro H, Bae K, Hattori M., 1998. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease. Chem Pharm Bull (Tokyo). 46(10):1607–1612. doi:10.1248/cpb.46.1607.
Monika OJ, Magdalena J, Magdalena MD, Adriana B, Tomasz PR, Grzegorz J, Jerzy W, Martyna KS., 2014. Exopolysaccharide from Ganoderma applanatum as a promising bioactive compound with cytostatic and antibacterial properties. BioMed Res Int. 743812:10p. doi:10.1155/2014/743812.
Moradali M-F, Mostafavi H, Hejaroude G-A, Tehrani AS, Abbasi M, Ghods S., 2006. Investigation of potential antibacterial properties of methanol extracts from fungus Ganoderma applanatum. Chemotherapy. 52(5):241–244. doi:10.1159/000094866.
NIA (National Institute on Aging). 2023. [accessed 2023 Dec 15]. https://www.nia.nih.gov/health/what-causes-alzheimers-disease.
Oh MH, Houghton PJ, Whang WK, Cho JH., 2004. Screening of Korean herbal medicines used to improve cognitive function for anti-cholinesterase activity. Phytomedicine. 11(6):544–548. doi:10.1016/j.phymed.2004.03.001.
Path Canada. 1994. Field test methods for the determination of iron in fortified foods. Health Bridje. 1–8p. https://hdl.handle.net/10625/29582.
Rahman AU, Choudhary MI., 2001. Bioactive natural products as a potential source of new pharmacophores a theory of memory. Pure Appl Chem. 73(3):555–560. doi:10.1351/pac200173030555.
Reiman EM, Quiroz YT, Fleisher AS, Chen K, Velez-Pardo C, Jimenez-Del-Rio M, Fagan AM, Shah AR, Alvarez S, Arbelaez A, et al.2012. Brain imaging and fluid biomarker analysis in young adults at genetic risk for autosomal dominant Alzheimer’s disease in the presenilin 1 E280A kindred: a case-control study. Lancet Neurol. 11(12):1048–1056. 2012; doi:10.1016/S1474-4422(12)70228-4.
Sakava P, Nyemb JN, Matchawe C, Kumcho MP, Tagatsing MF, Nsawir BJ, Talla E, Atchadé ADT, Laurent S, Henoumont C., 2024. Chemical constituents and antibacterial activities of Cameroonian dark brown propolis against potential biofilm-forming bacteria. Nat Prod Res. doi:10.1080/14786419.2024.2437024.
Saunders AM, Strittmatter WJ, Schmechel D, George-Hyslop PH, Pericak-Vance MA, Joo SH, Rosi BL, Gusella JF, Crapper-MacLachlan DR, Alberts MJ, et al.1993. Association of apolipoprotein E allele epsilon 4 with late-onset familial and sporadic Alzheimer’s disease. Neurology. 43(8):1467–1472. doi:10.1212/wnl.43.8.1467.
Schulz V., 2003. Ginkgo extract or cholinesterase inhibitors in patients with dementia: what clinical trial and guidelines fail to consider. Phytomedicine. 10 Suppl 4:74–79. doi:10.1078/1433-187x-00302.
Shamameh M, Syamak FG, Mohammad RA, Atousa V., 2019. Antioxidant Activity and Some Biochemical Properties of Ganoderma applanatum (Pers.) Pat. from Iran. Adv Res Mic Met Tech. 2:61–69.
Vega-Mendoza M, West H, Sorace A, Bak TH., 2015. The impact of late, non-balanced bilingualism on cognitive performance. Cognition. 137:40–46. doi: 10.1016/j.cognition.2014.12.008.25596355
Venditti A, Frezza C, Sciubba F, Serafini M, Bianco A., 2017. Primary and secondary metabolites of an European edible mushroom and its nutraceutical value: Suillus bellinii (Inzenga) Kuntze. Nat Prod Res. 31(16):1910–1919. doi:10.1080/14786419.2016.1267731.
Villemagne VL, Burnham S, Bourgeat P, Brown B, Ellis KA, Salvado O, Szoeke C, Macaulay SL, Martins R, Maruff P, et al.2013. Amyloid β deposition, neurodegeneration, and cognitive decline in sporadic Alzheimer’s disease: a prospective cohort study. Lancet Neurol. 12(4):357–367. doi:10.1016/S1474-4422(13)70044-9.
Vinutha B, Prashanth D, Salma K, Sreeja SL, Pratiti D, Padmaja R, Radhika S, Amit A, Venkateshwarlu K, Deepak M., 2007. Screening of selected Indian medicinal plants for acetylcholinesterase inhibitory activity. J Ethnopharmacol. 109(2):359–363. doi:10.1016/j.jep.2006.06.014.
WHO. 2023a. Ageing and health. [accessed 2023 Jul 31]. https://www.who.int/news-room/fact-sheets/detail/ageing-and-health.