Research Article

Radical Scavenging, Anti-Inflammatory, and Hepatoprotective Activities of Pentacyclic Triterpene isolated from Rosa webbiana

Author(s): Abdullah, Mir Azam Khan* and Achyut Adhikari*

Volume 24, Issue 16, 2023

Published on: 09 November, 2023

Page: [1282 - 1291] Pages: 10

DOI: 10.2174/0113894501261030231101184216

Price: $65

Abstract

Introduction: Rosa webbiana (RW) Wall Ex. Royle is used in traditional medicine in Pakistan for the treatment of several diseases including jaundice. To date, only neuroprotective potential of the plant has been evaluated.

Objective: The current study was designed to isolate bioactive compound(s) and investigate its possible radical scavenging, anti-inflammatory and hepatoprotective activities.

Methods: Column chromatography was done to isolate compounds from the chloroform fraction of RW. The compound was characterized by mass spectrometry, 1H-NMR, and 2D-NMR spectroscopy. Radical scavenging activity was assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydrogen peroxide (H2O2) assays, while anti-inflammatory potential was evaluated via xylene-induced ear edema and carrageenan-induced paw edema models. For hepatoprotection, CCl4-induced model in mice was used.

Results: A triterpene compound (3α, 21β-dihydroxy-olean-12-ene) was isolated from RW fruits (ARW1). The compound exhibited DPPH and H2O2 scavenging activities 61 ± 1.31% and 66 ± 0.48% respectively at 500 μg/ml. ARW1 (at 50 mg/kg) exhibited 62.9 ± 0.15% inhibition of xylene-induced ear edema and 66.6 ± 0.17% carrageenan-induced paw edema in mice. In CCl4-induced hepatotoxic mice, ARW1 significantly countered elevation in alanine transaminase (ALT), alkaline phosphatase (ALP), total bilirubin (T.B), and reduction in total protein (T.P) levels. Liver histomorphological study supported the serum biochemical profile for hepatoprotection. Moreover, ARW1 significantly attenuated the toxic changes in body and liver weight induced by CCl4.

Conclusion: The compound ARW1 exhibited anti-radical, anti-inflammatory and hepatoprotective effects. The anti-inflammatory and hepatoprotective activities may be attributed to anti-oxidant potential of the compound.

Keywords: Triterpene, radical scavenging, anti-inflammatory, isolation, hepatoprotective, Rosa webbiana.

« Previous
Graphical Abstract
[1]
Sini K, Haribabu Y, Sajith M, Sreekumar S J J o C, Research P. in-vitro Cytotoxic activity of Orthosiphon thymi fl orus(Roth.) sleensen leaf extract against dalton lymphoma ascites cell line. J Chem Pharm Res 2012; 4(1): 917-21.
[2]
Aggarwal B B, Kumar A, Bharti A C J A r. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res 2003; 23(1/A): 363-98.
[3]
Cragg G M, Newman D J J J o e. Plants as a source of anti-cancer agents. J Ethnopharmacol 2005; 100((1-2)): 72-9.
[http://dx.doi.org/10.1016/j.jep.2005.05.011]
[4]
Abdullah MAK, Ahmad Waqar, Ahmad Manzoor, Nisar Mohammad. Hepatoprotective effect of the solvent extracts of Viola canescens Wall. ex. Roxb. against CCl4 induced toxicity through antioxidant and membrane stabilizing activity. BMC Complement Altern Med 2017; 17(10)
[5]
Abdullah M A K, Ahmad W, Adhikari A, et al. Exploration of hepatoprotective potential and phytochemicals of ziziphus oxyphylla edgew. Pak Vet J 2020; 40(4): 431-6.
[6]
Zaidi S F, Muhammad J S, Shahryar S, et al. Anti-inflammatory and cytoprotective effects of selected Pakistani medicinal plants in Helicobacter pylori-infected gastric epithelial cells. J Ethnopharmacol 2012; 141(1): 403-10.
[http://dx.doi.org/10.1016/j.jep.2012.03.001]
[7]
Kong F-L, Zhang M-W, Kuang R-B, Yu S-J, Chi J-W, Wei Z-C J C P. Antioxidant activities of different fractions of polysaccharide purified from pulp tissue of litchi (Litchi chinensis Sonn.). Molecules 2010; 15(4): 2152-65.
[8]
Jiangjiang Q, Wei W, Zhang R J C j o n m. Novel natural product therapeutics targeting both inflammation and cancer. Chin J Nat Med 2017; 15(6): 401-16.
[9]
Coussens L M, Werb Z J N. Inflammation and cancer. Nature 2002; 420(6917): 860-7.
[http://dx.doi.org/10.1038/nature01322]
[10]
Hussain S P, Hofseth L J, Harris C C J N R C. Radical causes of cancer. Nat Rev Cancer 2003; 3(4): 276-85.
[http://dx.doi.org/10.1038/nrc1046]
[11]
Ravipati A S, Zhang L, Koyyalamudi S R, et al. Antioxidant and anti-inflammatory activities of selected Chinese medicinal plants and their relation with antioxidant content. BMC Complement Altern Med 2012; 6(12): 173.
[http://dx.doi.org/10.1186/1472-6882-12-173]
[12]
Tasneem S, Liu B, Li B, Choudhary M I, Wang W J P r. Molecular pharmacology of inflammation: Medicinal plants as anti-inflammatory agents. Pharmacol Res 2019; 139: 126-40.
[13]
Nathan C, Ding A J C. Nonresolving inflammation. Cell 2010; 140(6): 871-82.
[http://dx.doi.org/10.1016/j.cell.2010.02.029]
[14]
General USPHSOS, Prevention U S O o D, Promotion H, Control C f D. Prevention, The Surgeon General's call to action to prevent and decrease overweight and obesity 2001.
[15]
Schmid-Schönbein G W J A R B E. Analysis of inflammation. Annu Rev Biomed Eng 2006; 8: 93-131.
[http://dx.doi.org/10.1146/annurev.bioeng.8.061505.095708]
[16]
Mabberley DJ. Mabberley’s plant-book A portable dictionary of plants, their classifications and uses. (3rd ed.). Seattle: University of Washington Botanic Gardens 2008; p. 1040.
[17]
Sheng H, Sun H J N p r. Synthesis, biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases. Nat Prod Rep 2011; 28(3): 543-93.
[18]
Krasutsky P A J N p r. Birch bark research and development Nat Prod Rep 2006; 23(6): 919-42.
[http://dx.doi.org/10.1039/b606816b]
[19]
Cichewicz R H, Kouzi S A J M r r. Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. Med Res Rev 2004; 24(1): 90-114.
[20]
Thurnher D, Turhani D, Pelzmann M, et al. Betulinic acid: A new cytotoxic compound against malignant head and neck cancer cells. Head Neck 2003; 25(9): 732-40.
[21]
Otuki MF, Ferreira J, Lima FV, et al. Antinociceptive properties of mixture of α-amyrin and β-amyrin triterpenes: evidence for participation of protein kinase C and protein kinase A pathways. J Pharmacol Exp Ther 2005; 313(1): 310-8.
[http://dx.doi.org/10.1124/jpet.104.071779] [PMID: 15626726]
[22]
Dashbaldan S, Pączkowski C, Szakiel A J I j o m s. Variations in triterpenoid deposition in cuticular Waxes during development and maturation of selected fruits of Rosaceae family. Int J Mol Sci 2020; 21(24): 9762.
[http://dx.doi.org/10.3390/ijms21249762]
[23]
Mármol I, Sánchez-de-Diego C, Jiménez-Moreno N, Ancín-Azpilicueta C, Rodríguez-Yoldi M J J I j o m s. Therapeutic applications of rose hips from different Rosa species. Int J Mol Sci 2017; 18(6): 1137.
[http://dx.doi.org/10.3390/ijms18061137]
[24]
Dashbaldan S, Rogowska A, Pączkowski C, Szakiel A. Distribution of triterpenoids and steroids in developing rugosa rose (rosarugosa thunb.) accessory fruit. Molecules 2021; 26(17): 5158.
[http://dx.doi.org/10.3390/molecules26175158] [PMID: 34500591]
[25]
Younis W, Asif H, Sharif A, Riaz H, Bukhari I A, Assiri A M J C m. Traditional medicinal plants used for respiratory disorders in Pakistan: a review of the ethno-medicinal and pharmacological evidence. Chin Med 2018; 13(1): 1-29.
[26]
Akbar M, Ahmed M, Hussain A, Zafar M U, Khan M J F J o B. Quantitative forests description from Skardu, Gilgit and Astore Districts of Gilgit-Baltistan. Pakistan 2011; 1: pp. 149-60.
[27]
Khare CP. Indian medicinal plants: an illustrated dictionary. Springer Science & Business Media 2008.
[28]
Nguyen D P, Garcia Alai M M, Kapadnis P B, Neumann H, Chin J W J J o t A C S. Genetically encoding N ϵ-methyl-l-lysine in recombinant histones. J Am Chem Soc 2009; 131(40): 14194-5.
[29]
Abbas Z, Khan S M, Alam J, Khan S W, Abbasi A M J J o e. Medicinal plants used by inhabitants of the Shigar Valley, Baltistan region of Karakorum range-Pakistan. Ethnobiol Ethnomed 2017; 13(1): 53.
[30]
Akhter N, Akhtar S, Kazim S, Khan T J N. Science, Ethnomedicinal study of important medicinal plants used for gynecological issues among rural women folk in district gilgit. 2016; 14: 30-4.
[31]
Hussain I, Bano A, Ullah FJPJB. Traditional drug therapies from various medicinal plants of central karakoram national park. Gilgit-Baltistan Pakistan 2011; 43: 79-84.
[32]
Firdous A, Sarwar S, Shah F A, et al. Contribution of Attenuation of TNF-α and NF-κB in the Anti-Epileptic, Anti-Apoptotic and Neuroprotective Potential of Rosa webbiana Fruit and Its Chitosan Encapsulation. Molecules 2021; 26(8): 2347.
[33]
Cáceres-Castillo D, Mena-Rejón GJ, Cedillo-Rivera R, Quijano L. 21β-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa. Phytochemistry 2008; 69(4): 1057-64.
[http://dx.doi.org/10.1016/j.phytochem.2007.10.016] [PMID: 18061220]
[34]
Braca A, Sortino C, Politi M, Morelli I, Mendez J. Antioxidant activity of flavonoids from Licania licaniaeflora. J Ethnopharmacol 2002; 79(3): 379-81.
[http://dx.doi.org/10.1016/S0378-8741(01)00413-5] [PMID: 11849846]
[35]
Ruch RJ, Cheng S, Klaunig JE. Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis 1989; 10(6): 1003-8.
[http://dx.doi.org/10.1093/carcin/10.6.1003] [PMID: 2470525]
[36]
Walker CIB, Trevisan G, Rossato MF, et al. Antinociceptive activity of Mirabilis jalapa in mice. J Ethnopharmacol 2008; 120(2): 169-75.
[http://dx.doi.org/10.1016/j.jep.2008.08.002] [PMID: 18761072]
[37]
Shahriar M, Ashraf A, Choudhuri M, Basher S. Antinociceptive, anti-inflammatory and anti-diarrheal activities of the hydroalcoholic extract of lasia spinosa linn.(araceae) roots. Lat Am J Pharm 2010; 29(8): 1269-76.
[38]
Muhammad N, Saeed M, Khan H J B c. Antipyretic, analgesic and anti-inflammatory activity of Viola betonicifolia whole plant. BMC Complement Altern Med 2012; 12: 1-8.
[39]
Navarro M, Montilla M, Martín A, Jiménez J, Utrilla M. Free radical scavenger and antihepatotoxic activity of Rosmarinus tomentosus. Planta Med 1993; 59(4): 312-4.
[http://dx.doi.org/10.1055/s-2006-959688] [PMID: 8372145]
[40]
Galigher A E, Kozloff E N. Essentials of practical microtechnique. 1971.
[41]
Huang Q, Zhang S, Zheng L, et al. Hepatoprotective effects of total saponins isolated from Taraphochlamys affinis against carbon tetrachloride induced liver injury in rats. Food Chem Toxicol 2012; 50(3-4): 713-8.
[http://dx.doi.org/10.1016/j.fct.2011.12.009]
[42]
Djordjević VB. Free radicals in cell biology. Int Rev Cytol 2004; 237(237): 57-89.
[http://dx.doi.org/10.1016/S0074-7696(04)37002-6] [PMID: 15380666]
[43]
Abdullah , Khan MA, Ahmad W, et al. Antioxidant, antinociceptive, anti-inflammatory, and hepatoprotective activities of pentacyclic triterpenes isolated from Ziziphus oxyphylla Edgew. Drug Chem Toxicol 2022; 45(4): 1796-807.
[http://dx.doi.org/10.1080/01480545.2021.1880427] [PMID: 33557649]
[44]
Topçu G, Ertaş A, Kolak U, Öztürk M, Ulubelen A. Antioxidant activity tests on novel triterpenoids from Salvia macrochlamys. ARKIVOC 2006; 2007(7): 195-208.
[http://dx.doi.org/10.3998/ark.5550190.0008.716]
[45]
Huang D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J Agric Food Chem 2005; 53(6): 1841-56.
[http://dx.doi.org/10.1021/jf030723c] [PMID: 15769103]
[46]
Parthasarathy S, Bin Azizi J, Ramanathan S, et al. Evaluation of antioxidant and antibacterial activities of aqueous, methanolic and alkaloid extracts from Mitragyna speciosa (Rubiaceae family) leaves. Molecules 2009; 14(10): 3964-74.
[http://dx.doi.org/10.3390/molecules14103964] [PMID: 19924042]
[47]
Keser S, Celik S, Turkoglu S, Yilmaz O, Turkoglu I. Hydrogen peroxide radical scavenging and total antioxidant activity of hawthorn. Chem J 2012; 2(1): 9-12.
[48]
Rajamanikandan S, Sindhu T, Durgapriya D, Sophia D, Ragavendran P, Gopalakrishnan V. Radical scavenging and antioxidant activity of ethanolic extract of Mollugo nudicaulis by in vitro assays. Indian J Pharm Educ Res 2011; 45(4): 310-6.
[49]
Bhatti MZ, Ali A, Ahmad A, Saeed A, Malik SA. Antioxidant and phytochemical analysis of Ranunculus arvensis L. extracts. BMC Res Notes 2015; 8(1): 279.
[http://dx.doi.org/10.1186/s13104-015-1228-3] [PMID: 26123646]
[50]
Yang J, Li S, Xie C, et al. Anti-inflammatory activity of ethyl acetate fraction of the seeds of Brucea Javanica. J Ethnopharmacol 2013; 147(2): 442-6.
[http://dx.doi.org/10.1016/j.jep.2013.03.034] [PMID: 23538165]
[51]
Braca A, Dal Piaz F, Marzocco S, Autore G, Vassallo A, De Tommasi N. Triterpene derivatives as inhibitors of protein involved in the inflammatory process: molecules interfering with phospholipase A2, cycloxygenase, and lipoxygenase. Curr Drug Targets 2011; 12(3): 302-21.
[http://dx.doi.org/10.2174/138945011794815284] [PMID: 20955150]
[52]
Khan MA, Khan H, Khan S, Mahmood T, Khan PM, Jabar A. Anti-inflammatory, analgesic and antipyretic activities of Physalis minima Linn. J Enzyme Inhib Med Chem 2009; 24(3): 632-7.
[http://dx.doi.org/10.1080/14756360802321120] [PMID: 18825533]
[53]
Maity TK, Mandal SC, Mukherjee PK, et al. Studies on antiinflammatory effect ofCassia tora leaf extract (fam. Leguminosae). Phytother Res 1998; 12(3): 221-3.
[http://dx.doi.org/10.1002/(SICI)1099-1573(199805)12:3<221::AID-PTR221>3.0.CO;2-L]
[54]
Vuda M, D’Souza R, Upadhya S, et al. Hepatoprotective and antioxidant activity of aqueous extract of Hybanthus enneaspermus against CCl4-induced liver injury in rats. Exp Toxicol Pathol 2012; 64(7-8): 855-9.
[http://dx.doi.org/10.1016/j.etp.2011.03.006] [PMID: 21478003]
[55]
Tu C, Gao D, Li XF, et al. Inflammatory stress potentiates emodin-induced liver injury in rats. Front Pharmacol 2015; 6: 233.
[http://dx.doi.org/10.3389/fphar.2015.00233] [PMID: 26557087]
[56]
Khan RA, Khan MR, Sahreen S. CCl4-induced hepatotoxicity: Protective effect of rutin on p53, CYP2E1 and the antioxidative status in rat. BMC Complement Altern Med 2012; 12(1): 178.
[http://dx.doi.org/10.1186/1472-6882-12-178] [PMID: 23043521]
[57]
Sallie R, Michael Tredger J, Williams R. Drugs and the liver part 1: Testing liver function. Biopharm Drug Dispos 1991; 12(4): 251-9.
[http://dx.doi.org/10.1002/bdd.2510120403] [PMID: 1873506]
[58]
Wu CR, Hseu YC, Lien JC, Lin LW, Lin YT, Ching H. Triterpenoid contents and anti-inflammatory properties of the methanol extracts of ligustrum species leaves. Molecules 2010; 16(1): 1-15.
[http://dx.doi.org/10.3390/molecules16010001] [PMID: 21187813]
[59]
Safayhi H, Sailer ER. Anti-inflammatory actions of pentacyclic triterpenes. Planta Med 1997; 63(6): 487-93.
[http://dx.doi.org/10.1055/s-2006-957748] [PMID: 9434597]
[60]
Afsar T, Razak S, Almajwal A. Effect of Acacia hydaspica R. Parker extract on lipid peroxidation, antioxidant status, liver function test and histopathology in doxorubicin treated rats. Lipids Health Dis 2019; 18(1): 126.
[http://dx.doi.org/10.1186/s12944-019-1051-2] [PMID: 31142345]
[61]
Peters JM, Boyd EM. Organ weights and water levels of the rat following reduced food intake. J Nutr 1966; 90(4): 354-60.
[http://dx.doi.org/10.1093/jn/90.4.354] [PMID: 5954817]
[62]
Pfeiffer CJ. A mathematical evaluation of the thymic weight parameter. Toxicol Appl Pharmacol 1968; 13(2): 220-7.
[http://dx.doi.org/10.1016/0041-008X(68)90096-3] [PMID: 5726415]
[63]
Chao W-W, Chen S-J, Peng H-C, Liao J-W, Chou S-T J A. Antioxidant activity of graptopetalum paraguayense E. Walther leaf extract counteracts oxidative stress induced by ethanol and carbon tetrachloride Co-induced hepatotoxicity in rats. Antioxidants 2019; 8(8): 251.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy