Characterization, Antioxidant and Anticholinesterase Activity of Compounds Isolated from Alkaloid Extracts of Citrus aurantifolia Root Bark

Year 2024, Volume: 11 Issue: 3, 1227 - 1236, 30.08.2024

Djélé Alette Edwige Zıale , Demel Axel Adou , Kohue Christelle Chantal N'gaman-kouassı , Julia Deschamp , Nadia Bouchemal , Tony Lionel Palama , Marc Lecouvey , Janat Akhanovna Mamyrbekova-békro , Yves-alain Bekro

https://doi.org/10.18596/jotcsa.1395690

Abstract

Xanthyletin (1), edulinin (2), 1-methyl-2-[(E)-(prop-1-enyl)]quinolin-4-one (3), 1,2-dimethylquinolin-4-one (4), lonchocarpol A (5), grandisinin (6), citracridone-I (7) and 5-hydroxynoracronycin (8) were isolated from alkaloid extracts of the root bark of Citrus aurantifolia. Their structures were characterized using spectral data (NMR, HRMS, and IR). Furthermore, compounds 2, 3, 4, and 6 known in the literature have been isolated for the first time in Citrus aurantifolia. However, compounds 1, 5, 7 and 8 are already known from the plant studied. The concentration required to reduce 50% of free radicals (RC50) was carried out. Compounds 3 (RC50= 185.836 µmol/L) and 4 (RC50= 218.277 µmol/L) compared with vitamin C (RC50= 17.033 µmol/L) showed antioxidant efficacy. The highest anticholinesterase activity was observed for compound 6 at 21.129 µM followed by compounds 3 and 4 at 251.130, 287.208 µM, respectively.

Keywords

Citrus aurantifolia, alkaloids, isollation, antioxidant, anticholinesterase

Thanks

The authors thank the "Ministère de l'Enseignement Supérieur et de la Recherche Scientifique de Côte d'Ivoire (MESRSCI) for the financial support given to Djélé Alette Edwige Zialé for her PhD training at the Laboratoire CSPBAT of the Université Sorbonne Paris Nord, Bobigny (France). They also express their gratitude to the USPN for the access to the NMR Platform and to Professor Malan Djah François for the identification of the plant species studied.

References

• 1. Brookmeyer R, Johnson E, Ziegler‐Graham K, Arrighi HM. Forecasting the global burden of Alzheimer’s disease. Alzheimer’s Dement [Internet]. 2007 Jul 1;3(3):186–91. Available from: <URL>.
• 2. Ahue MK, Bekro JAM, Maurice T, Virieux D, Pirat JL, Bekro YA. Preliminary phytochemical screening and protective effect of Erythrina Senegalensis in an in vivo mouse model of Alzheimer’s disease. J Med Pharm Allied Sci [Internet]. 2017 Mar 1;630–44. Available from: <URL>.
• 3. Ferri CP, Prince M, Brayne C, Brodaty H, Fratiglioni L, Ganguli M, et al. Global prevalence of dementia: a Delphi consensus study. Lancet [Internet]. 2005 Dec 17;366(9503):2112–7. Available from: <URL>.
• 4. Adou DA, guessan AHON, -Békro JAM, Békro YA. Evaluation of the antioxidant potential and aglycone coumarins contents of ethereal extracts of 4 medicinal plants from Côte d’Ivoire. J Pharmacogn Phytochem [Internet]. 2022 Nov 1;11(6):46–9. Available from: <URL>.
• 5. Aisa ER, Tukiran T. Comparison on Total Phenolics and Flavonoids and Antioxidant Activities of Methanol Extract of Horseshoe Crab (Tachypleus gigas) Eggs. J Turkish Chem Soc Sect A Chem [Internet]. 2023 Aug 30;10(3):787–96. Available from: <URL>.
• 6. El Kadmiri N, Hamzi K, El Moutawakil B, Slassi I, Nadifi S. Les aspects génétiques de la maladie d’Alzheimer (Revue). Pathol Biol [Internet]. 2013 Dec 1;61(6):228–38. Available from: <URL>.
• 7. Schliebs R, Arendt T. The significance of the cholinergic system in the brain during aging and in Alzheimer’s disease. J Neural Transm [Internet]. 2006 Nov 9;113(11):1625–44. Available from: <URL>.
• 8. Ziale DAE, Ngaman Kouassi KCC, Deschamp J, Bouchemal N, Palama TL, Lecouvey M, et al. Structural characterization and in vitro biological exploration of phytoconstituents isolated from a chloroform extract of Rauvolfia vomitoria (Apocynaceae) root bark from Côte d’Ivoire. J Pharmacogn Phytochem [Internet]. 2023 Jan 1;12(1):06–14. Available from: <URL>.
• 9. Ettebong E, Ubulom P, Etuk A. Antiplasmodial activity of methanol leaf extract of Citrus aurantifolia (Christm) Swingle. J Herbmed Pharmacol [Internet]. 2019 Sep 1;8(4):274–80. Available from: <URL>.
• 10. Sunday Enejoh O, Oladejo Ogunyemi I, Smart Bala M, Sotonye Oruene I, Musa Suleiman M, Folorunsho Ambali S. Ethnomedical Importance of Citrus Aurantifolia (Christm) Swingle. Pharma Innov J [Internet]. 2015;4(8):1–6. Available from: <URL>.
• 11. Amat-ur-Rasool H, Symes F, Tooth D, Schaffert LN, Elmorsy E, Ahmed M, et al. Potential Nutraceutical Properties of Leaves from Several Commonly Cultivated Plants. Biomolecules [Internet]. 2020 Nov 15;10(11):1556. Available from: <URL>.
• 12. de Andrade JP, Giordani RB, Torras-Claveria L, Pigni NB, Berkov S, Font-Bardia M, et al. The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids. Phytochem Rev [Internet]. 2016 Feb 22;15(1):147–60. Available from: <URL>.
• 13. Assohoun K, Kabran GRM, Bekro JAM, Virieux D, Pirat JL, Bekro YA. Total alkaloids and in vitro antioxidant activity of Crinum jagus L. (Amaryllidaceae) organs from Côte d’Ivoire. Int J Green Herb Chem [Internet]. 2020 Oct 31;9(4):451–63. Available from: <URL>.
• 14. Blois MS. Antioxidant Determinations by the Use of a Stable Free Radical. Nature [Internet]. 1958 Apr;181(4617):1199–200. Available from: <URL>.
• 15. Etekpo SD, N’Gaman-Kouassi K, Yao T, Mamyrbekova-Bekro J, Bekro Y. Phytochemical, Antioxidant and pharmacological study of (SM.) JACQ.- FEL. (Melastomataceae). J Pharm Biol Sci [Internet]. 2022 Jul 28;10(1):37–43. Available from: <URL>.
• 16. Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol [Internet]. 1961 Jul 1;7(2):88–95. Available from: <URL>.
• 17. Amaral JC, da Silva MM, da Silva MFGF, Alves TC, Ferreira AG, Forim MR, et al. Advances in the Biosynthesis of Pyranocoumarins: Isolation and 13 C-Incorporation Analysis by High-Performance Liquid Chromatography–Ultraviolet–Solid-Phase Extraction–Nuclear Magnetic Resonance Data. J Nat Prod [Internet]. 2020 May 22;83(5):1409–15. Available from: <URL>.
• 18. Noulala CGT, Ouete JLN, Atangana AF, Mbahbou GTB, Fotso GW, Stammler HG, et al. Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules [Internet]. 2022 Feb 7;27(3):1104. Available from: <URL>.
• 19. Yang Z duo, Zhang D bo, Ren J, Yang M jun. Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitor. Med Chem Res [Internet]. 2012 Jun 4;21(6):722–5. Available from: <URL>.
• 20. Nguyen NT, Dang PH, Vu NXT, Le TH, Nguyen MTT. Quinoliniumolate and 2 H -1,2,3-Triazole Derivatives from the Stems of Paramignya trimera and Their α-Glucosidase Inhibitory Activities: In Vitro and in Silico Studies. J Nat Prod [Internet]. 2017 Jul 28;80(7):2151–5. Available from: <URL>.
• 21. Yasir M, Tripathi MK, Singh P, Shrivastava R. The Genus Glycosmis [Rutaceae]: A Comprehensive Review on its Phytochemical and Pharmacological Perspectives. Nat Prod J [Internet]. 2019 Mar 18;9(2):98–124. Available from: <URL>.
• 22. Rádl S, Obadalová I. Utilization of Aromatic Denitrocyclization Reaction for the Synthesis of 3-Unsubstituted 1,4-Dihydroquinolin-4-one Derivatives. Collect Czechoslov Chem Commun [Internet]. 2004 Apr;69(4):822–32. Available from: <URL>.
• 23. Ribeiro AB, Abdelnur PV, Garcia CF, Belini A, Severino VGP, da Silva MF das GF, et al. Chemical Characterization of Citrus sinensis Grafted on C. limonia and the Effect of Some Isolated Compounds on the Growth of Xylella fastidiosa. J Agric Food Chem [Internet]. 2008 Sep 10;56(17):7815–22. Available from: <URL>.
• 24. Tahara S, Katagiri Y, Ingham JL, Mizutani J. Prenylated flavonoids in the roots of yellow lupin. Phytochemistry [Internet]. 1994 Aug 10;36(5):1261–71. Available from: <URL>.
• 25. Tian-Shung W, Chang-Sheng K, Furukawa H. Acridone alkaloids and a coumarin from Citrus grandis. Phytochemistry [Internet]. 1983 Jan 1;22(6):1493–7. Available from: <URL>.
• 26. Ye Y, Xu G, Li DL. Acridone alkaloids and flavones from the leaves of Citrus reticulata. Nat Prod Res [Internet]. 2022 Jul 18;36(14):3644–50. Available from: <URL>.
• 27. Segun PA, Ismail FMD, Ogbole OO, Nahar L, Evans AR, Ajaiyeoba EO, et al. Acridone alkaloids from the stem bark of Citrus aurantium display selective cytotoxicity against breast, liver, lung and prostate human carcinoma cells. J Ethnopharmacol [Internet]. 2018 Dec 5;227:131–8. Available from: <URL>.
• 28. Bissim SM, Kenmogne SB, Tcho AT, Lateef M, Ahmed A, Ngeufa Happi E, et al. Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochem Lett [Internet]. 2019 Feb 1;29:148–53. Available from: <URL>.
• 29. Tjahjandarie TS, Pudjiastuti P, Saputri RD, Tanjung M. Antimalarial and antioxidant activity of phenolic compounds isolated from Erythrina crista-galli L. J Chem Pharm Res [Internet]. 2014;6(4):786–90. Available from: <URL>.
• 30. Favier A. Intérêt conceptuel et expérimental dans la compréhension des mécanismes des maladies et potentiel thérapeutique.
• 31. Berkov S, Codina C, Viladomat F, Bastida J. N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum. Bioorg Med Chem Lett [Internet]. 2008 Apr 1;18(7):2263–6. Available from: <URL>.
• 32. Sarikaya BB, Kaya GI, Onur MA, Bastida J, Somer NU. Phytochemical investigation of Galanthus woronowii. Biochem Syst Ecol [Internet]. 2013 Dec;51:276–9. Available from: <URL>.
• 33. Ortiz JE, Garro A, Pigni NB, Agüero MB, Roitman G, Slanis A, et al. Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species. Phytomedicine [Internet]. 2018 Jan 15;39:66–74. Available from: <URL>.
• 34. Ryu HW, Curtis-Long MJ, Jung S, Jeong IY, Kim DS, Kang KY, et al. Anticholinesterase potential of flavonols from paper mulberry (Broussonetia papyrifera) and their kinetic studies. Food Chem [Internet]. 2012 Jun 1;132(3):1244–50. Available from: <URL>.
• 35. Loizzo MR, Tundis R, Bonesi M, Menichini F, De Luca D, Colica C, et al. Evaluation of Citrus aurantifolia peel and leaves extracts for their chemical composition, antioxidant and anti‐cholinesterase activities. J Sci Food Agric [Internet]. 2012 Dec 16;92(15):2960–7. Available from: <URL>.