3,019
Views
6
CrossRef citations to date
0
Altmetric
Research Article

UPLC-PDA-ESI-QTOF-MS/MS fingerprint of purified flavonoid enriched fraction of Bryophyllum pinnatum; antioxidant properties, anticholinesterase activity and in silico studies

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, & show all
Pages 442-454 | Received 13 Apr 2020, Accepted 31 Mar 2021, Published online: 30 Apr 2021

References

  • Abubakar AA, Oladele HA, Adejumoke A, Kayode FJ. 2014. Synergistic effect of combined extract of Bryophyllum pinnatum and Aloe barbadensis enhances anti-microbial activity in vitro. Glob Adv Res J Med Med Sci. 3:26–32.
  • Ademosun AO, Oboh G, Bello F, Ayeni PO. 2016. Antioxidative properties and effect of quercetin and its glycosylated form (rutin) on acetylcholinesterase and butyrylcholinesterase activities. J Evid Based Complementary Altern Med. 21(4):NP11–NP17.
  • Afzal M, Kazmi I, Anwar F. 2013. Antineoplastic potential of Bryophyllum pinnatum (Lam.) on chemically induced hepato carcinogenesis in rats. Phcog Res. 5(4):247–253.
  • Ali Reza ASM, Hossain MS, Akhter S, Rahman MR, Nasrin MS, Uddin MJ, Sadik G, Khurshid AHM. 2018. In vitro antioxidant and cholinesterase inhibitory activities of Elatostema papillosum leaves and correlation with their phytochemical profiles: a study relevant to the treatment of Alzheimer’s disease. BMC Complement Altern Med. 18(1):123–131.
  • Asaduzzaman M, Uddin M, Kader M, Alam A, Rahman AA, Rashid MK, Kato K, Tanaka T, Takeda M, Sadik G. 2014. In vitro acetylcholinesterase inhibitory activity and the antioxidant properties of Aegle marmelos leaf extract: implications for the treatment of Alzheimer’s disease. Psychogeriatrics. 14(1):1–10.
  • Assefa AD, Ko EY, Moon SH, Keum YS. 2016. Antioxidant and antiplatelet activities of flavonoid-rich fractions of three citrus fruits from Korea. 3 Biotech. 6(1):1–10.
  • Badmus JA, Adedosu TO, Fatoki JO, Adegbite V, Adaramoye OA, Odunola OA. 2011. Lipid peroxidation inhibition and antiradical activities of some leaf fractions of Mangifera indica. Acta Pol Pharm. 68(1):23–29.
  • Ben Haj Yahia I, Zaouali Y, Ciavatta ML, Ligresti A, Jaouadi R, Boussaid M, Cutignano A. 2019. Polyphenolic profiling, quantitative assessment and biological activities of Tunisian native Mentha rotundifolia (L.) Huds. Molecules. 24(13):2351–2319.
  • Bensalem J, Dudonné S, Gaudout D, Servant L, Calon F, Desjardins Y, Layé S, Lafenetre P, Pallet V. 2018. Polyphenol-rich extract from grape and blueberry attenuates cognitive decline and improves neuronal function in aged mice. J Nutr Sci. 7(e19):e19–e10.
  • Brand-Williams W, Cuvelier ME, Berset C. 1995. Use of a free radical method to evaluate antioxidant activity. Lebensm-Wiss U-Technol. 28(1):25–30.
  • Brito A, Ramirez JE, Areche C, Sepúlveda B, Simirgiotis MJ. 2014. HPLC-UV-MS profiles of phenolic compounds and antioxidant activity of fruits from three Citrus species consumed in northern Chile. Molecules. 19(11):17400–17421.
  • Chauhan V, Chauhan A. 2006. Oxidative stress in Alzheimer’s disease. Pathophysiology. 13(3):195–208.
  • Cheung J, Rudolph MJ, Burshteyn F, Cassidy MS, Gary EN, Love J, Franklin MC, Height JJ. 2012. Structures of human acetylcholinesterase in complex with pharmacologically important ligands. J Med Chem. 55(22):10282–10286.
  • Chibli LA, Rodrigues KCM, Gasparetto CM, Pinto NCC, Fabri RL, Scio E, Alves MS, Del-Vechio-Vieira G, Sousa OV. 2014. Anti-inflammatory effects of Bryophyllum pinnatum (Lam.) Oken ethanol extract in acute and chronic cutaneous inflammation. J Ethnopharmacol. 154(2):330–338.
  • Chlebek J, Korábečný J, Doležal R, Štěpánková Š, Pérez D, Hošťálková A, Opletal L, Cahlíková L, Macáková K, Kučera T, et al. 2019. In vitro and in silico acetylcholinesterase inhibitory activity of thalictricavine and canadine and their predicted penetration across the blood-brain barrier. Molecules. 24(7):1311–1340.
  • Dohou N, Yamni K, Tahrouch S, Idrissi-Hassani L, Badoc A, Gmira N. 2003. Screening phytochimique d'une endémiqueibéro-marocaine, Thymelaea lythroides. Bull Soc Pharmacolo Bord. 142:61–78.
  • Ellman GL, Courtney KD, Andres V, Feather-Stone RM. 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 7:88–95.
  • Elufioye TO, Olusola DM, Oyedeji AO. 2019. Correlation of total phenolic, flavonoid and tannin content of Bryophyllum pinnatum (Lam.) (Crassulaceae) extract with the antioxidant and anticholinesterase activities. Pharmacology J. 11:1003–1009.
  • Feitosa CM, Freitas RM, Luz NNN, Bezerra MZB, Trevisan MTS. 2011. Acetylcholinesterase inhibition by somes promising Brazilian medicinal plants. Braz J Biol. 71(3):783–789.
  • Fernandes JM, Cunha LM, Azevedo EP, Lourenço EMG, Pedrosa MF, Zucolotto SM. 2019. Kalanchoe laciniata and Bryophyllum pinnatum: an updated review about ethnopharmacology, phytochemistry, pharmacology and toxicology. Rev Bras Farmacogn. 29(4):529–553.
  • Fischer R, Maier O. 2015. Interrelation of oxidative stress and inflammation in neurodegenerative disease: role of TNF. Oxid Med Cell Longev. 2015:610813–610818.
  • Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA, Sanschagrin PC, Mainz DT. 2006. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem. 49(21):6177–6196.
  • Fürer K, Raith M, Brenneisen R, Mennet M, Simões-Wüst A, Von Man-Dach U, Hamburger M, Potterat O. 2013. Two new flavonol glycosides and a metabolite profile of Bryophyllum pinnatum, a phytotherapeutic used in obstetrics and gynaecology. Planta Med. 79:1565–1571.
  • Garayev E, Di Giorgio C, Herbette G, Mabrouki F, Chiffolleau P, Roux D, Sallanon H, Ollivier E, Elias R, Baghdikian B. 2018. Bioassay-guided isolation and UHPLC-DAD-ESI-MS/MS quantification of potential anti-inflammatory phenolic compounds from flowers of Inula montana L. J Ethnopharmacol. 226:176–184.
  • Gupta S, Adak S, Rajak RC, Banerjee R. 2016. In vitro efficacy of Bryophyllum pinnatum leaf extracts as potent therapeutics. Prep Biochem Biotechnol. 46(5):489–494.
  • Huang WJ, Zhang X, Chen WW. 2016. Role of oxidative stress in Alzheimer’s disease. Biomed Rep. 4(5):519–522.
  • Jiménez-González A, Quispe C, Bórquez J, Sepúlveda B, Riveros F, Areche C, Nagles E, García-Beltrán O, Simirgiotis MJ. 2018. UHPLC-ESI-ORBITRAP-MS analysis of the native Mapuche medicinal plant palo negro (Leptocarpha rivularis DC. - Asteraceae) and evaluation of its antioxidant and cholinesterase inhibitory properties. J Enzyme Inhib Med Chem. 33(1):936–944.
  • John KMM, Vijayan D, Kumar RR, Premkumar R. 2005. Factors influencing the efficiency of extraction of polyphenols from young tea leaves. Asian J of Plant Sciences. 5(1):123–126.
  • Johnson G, Moore SW. 2006. The peripheral anionic site of acetylcholinesterase: structure, functions and potential role in rational drug design. Curr Pharm Des. 12(2):217–225.
  • Khan A, Ali T, Rehman SU, Khan MS, Alam SI, Ikram M, Muhammad T, Saeed K, Badshah H, Kim MO. 2018. Neuroprotective effect of quercetin against the detrimental effects of LPS in the adult mouse brain. Front Pharmacol. 9:1–16.
  • Khan H, Marya AS, Kamal MA, Patel S. 2018. Flavonoids as acetylcholinesterase inhibitors: current therapeutic standing and future prospects. Biomed Pharmacother. 101:860–870.
  • Kumar P, Mir S, Semalty A. 2014. Isolation and characterization of novel flavonoid from methanolic extract of Pongamia pinnata pods. Research J of Phytochemistry. 8(1):21–24.
  • Kumar S, Chowdhury S, Kumar S. 2017. In silico repurposing of antipsychotic drugs for Alzheimer’s disease. BMC Neurosci. 18(1):1–9.
  • Li K, Fan H, Yin P, Yang L, Xue Q, Li X, Sun L, Liu Y. 2018. Structure-activity relationship of eight high content flavonoids analyzed with a preliminary assign-score method and their contribution to antioxidant ability of flavonoids-rich extract from Scutellaria baicalensis shoots. Arab J Chem. 11(2):159–170.
  • Liang Z, Zhang J, Huang Y, Zhou C, Wang Y, Zhou CH, Xing SP, Shun QS, Xu YX, Wei G. 2019. Identification of flavonoids in Dendrobium huoshanense and comparison with those in allied species of Dendrobium by TLC, HPLC and HPLC coupled with electrospray ionization multi-stage tandem MS analyses. J Sep Sci. 42(5):1088–1104.
  • Luca M, Luca A, Calandra C. 2015. The role of oxidative damage in the pathogenesis and progression of Alzheimer’s disease and vascular dementia. Oxid Med Cell Longev. 2015:1–8.
  • Moodie LWK, Sepčić K, Turk T, Frangež R, Svenson J. 2019. Natural cholinesterase inhibitors from marine organisms. Nat Prod Rep. 36(8):1053–1092.
  • Muller FL, Lustgarten MS, Jang Y, Richardson A, Van Remmen H. 2007. Trends in oxidative aging theories. Free Radic Biol Med. 43(4):477–503.
  • National Academy of Science. 2011. Guide for the care and use of laboratory animals. Institute for laboratory animal research, national academy of sciences. 8th ed. Washington (DC): National Academies Press; p. 220.
  • Nicolet Y, Lockridge O, Masson P, Fontecilla-Camps JC, Nachon F. 2003. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J Biol Chem. 278(42):41141–41147.
  • Nwidu LL, Elmorsy E, Thornton J, Wijamunige B, Wijesekara A, Tarbox R, Warren A, Carter WG. 2017. Anti-acetylcholinesterase activity and antioxidant properties of extracts and fractions of Carpolobia lutea. Pharm Biol. 55(1):1875–1883.
  • Ogidigo JO, Anosike C, Nwodo OFC, Omotuyi O, Nash O, Metibemu S, Eniafe G, Okpalafe O, Sani M. 2018. In silico molecular docking and pharmacokinetic studies of some selected phyto-constituents of Byrophyllum pinnatum as a potential selective inhibitor of MAO-B. Pharmacologyonline 3(45):14–49.
  • Ojo OA, Ojo AB, Ajiboye BO, Olaiya O, Akawa A, Olaoye O, Anifowose OO, Idowu O, Olasehinde O, Obafemi T, et al. 2018. Inhibitory effect of Bryophyllum pinnatum (Lam.) Oken leaf extract and their fractions on α-amylase, α-glucosidase and cholinesterase enzyme. Pharmacology J. 10:497–506.
  • Omotuyi OI, Nash O, Inyang OK, Ogidigo J, Enejoh O, Okpalefe O, Hamada T. 2018. Flavonoid-rich extract of Chromolaena odorata modulate circulating GLP-1 in Wistar rats: computational evaluation of TGR5 involvement. 3 Biotech. 8(2):124–132.
  • Oufir M, Seiler C, Gerodetti M, Gerber J, Fürer K, Mennet-von Eiff M, Elsas SM, Brenneisen R, von Mandach U, Hamburger M, et al. 2015. Quantification of bufadienolides in Bryophyllum pinnatum leaves and manufactured products by UHPLC-ESIMS/MS. Planta Med. 81(12–13):1190–1197.
  • Panche AN, Diwan AD, Chandra SR. 2016. Flavonoids: an overview. J Nutr Sci. 5(e47): 1–15.
  • Plangger N, Rist L, Zimmermann R, von Mandach U. 2006. Intravenous tocolysis with Bryophyllum pinnatum is better tolerated than beta-agonist application. Eur J Obstet Gynecol Reprod Bio. 124(2):168–172.
  • Qiu C, Fratiglioni L. 2018. Aging without dementia is achievable: current evidence from epidemiological research. J Alzheimers Dis. 62(3):933–942.
  • Queen BL, Tollefsbol TO. 2010. Polyphenols and aging. Curr Aging Sci. 3(1):34–42.
  • Raeisi S. 2013. Molecular docking approach of monoamine oxidase B inhibitors for identifying new potential drugs: Insights into drug-protein interaction discovery. J Cell Mol Res. 5 (1):24–33.
  • Rahman MM, Islam MB, Biswas M, Khurshid Alam AH. 2015. In vitro antioxidant and free radical scavenging activity of different parts of Tabebuia pallida growing in Bangladesh. BMC Res Notes. 8(1):621–630.
  • Ruberto G, Baratta MT, Deans SG, Dorman HJ. 2000. Antioxidant and antimicrobial activity of Foeniculum vulgare and Crithmum maritimum essential oils. Planta Med. 66(8):687–693.
  • Salahdeen HM, Yemitan OK. 2006. Neuropharmacological effects of aqueous leaf extract of Bryophyllum pinnatum in mice. Afr J Med Health Sci. 9:101–107.
  • Sastry GM, Adzhigirey M, Day T, Annabhimoju R, Sherman W. 2013. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des. 27(3):221–234.
  • Sharma A, Bhot M, Chandra N. 2014. In vitro antibacterial and antioxidant activity of Bryophyllum pinnatum (Lam.) Kurz. Int J Pharm Pharm Sci. 6:558–560.
  • Stander MA, Van Wyk B, Taylor MJC, Long HSJ. 2017. Analysis of phenolic compounds in rooibos tea (Aspalathus linearis) with a comparison of flavonoid-based compounds in natural populations of plants from different regions. J Agric Food Chem. 65(47):10270–11028.
  • Suganthy N, Pandima DK. 2016. In vitro antioxidant and anti-cholinesterase activities of Rhizophora mucronata. Pharm Biol. 54(1):118–129.
  • Sun X, Jin L, Ling P. 2012. Review of drugs for Alzheimer’s disease. Drug Discov Ther. 6(6):285–290.
  • Swerdlow RH. 2007. Pathogenesis of Alzheimer’s disease. Clin Interv Aging. 2:347–359.
  • Tönnies E, Trushina E. 2017. Oxidative stress, synaptic dysfunction, and Alzheimer’s disease. JAD. 57(4):1105–1121.
  • Vijayan M, Reddy PH. 2016. Stroke, vascular dementia, and Alzheimer’s disease: molecular links. J Alzheimers Dis. 54(2):427–443.
  • 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. 109:359–363.
  • Wischik CM, Harrington CR, Storey JMD. 2014. Tau-aggregation inhibitor therapy for Alzheimer’s disease. Biochem Pharmacol. 88(4):529–539.
  • Wu L, Tong T, Wan S, Yan T, Ren F, Bi K, Jia Y. 2016. Protective effects of puerarin against Aβ 1-42-induced learning and memory impairments in mice. Planta Med. 83(03–04):224–231.
  • Yang X, Bai ZF, Zhang DW, Zhang Y, Cui H, Zhou HL. 2020. Enrichment of flavonoid-rich extract from Bidens bipinnata L. by macroporous resin using response surface methodology, UHPLC-Q-TOF MS/MS-assisted characterization and comprehensive evaluation of its bioactivities by analytical hierarchy process. Biomed Chromatogr. 34(11):e4933.
  • Zhishen J, Mengcheng T, Jianming W. 1999. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food Chem. 64(4):555–559.