Isolation and characterization of luteolin and ferulic acid from Plumbago auriculata cultivated in Iraq
DOI:
https://doi.org/10.31351/vol33iss(4SI)pp271-281Keywords:
Flavonoid, FTIR, HPLC, Identification, LC-MS/MS, PhenolAbstract
Plumbago auriculata is a perennial plant belong to Plumbaginaceae family. It is an endemic genus of 18 species in South Africa. All plant parts have many phytochemical compounds appearing several pharmacological activities. The study was aimed to isolate and identify of the bioactive phenolic compounds (luteolin and ferulic acid) from Plumbago auriculata cultivated in Iraq by various chromatographic and spectroscopic techniques. The plant materials were defatted with n-hexane solvent by maceration for 48hr, and extracted by soxhlet apparatus using 85% methanol solvent, then fractionated with the solvents of petroleum ether, chloroform, and ethyl acetate. High performance liquid chromatography (HPLC) was used to identify luteolin and ferulic acid in the fraction of ethyl acetate. The identified compounds were isolated using analytical HPLC, then characterized and identified the isolated compounds using various detecting techniques including , HPLC by comparing with their standards and spiking, Fourier transform infrared spectroscopy (FTIR), in addition to the liquid chromatography mass spectrometry (LC-MS/MS). The results of spectroscopic techniques confirmed the existence of luteolin and ferulic acid in the fraction of ethyl acetate, as it concluded that the data for the isolated compounds were coincided with that reported for the compounds in literatures. These isolated polyphenolic compounds which have various pharmacological activities may demonstrate some of the therapeutic uses of P.auriculata plant.
How to Cite
Publication Dates
Received
Revised
Accepted
Published Online First
References
Zirjawi OS, Almousawi UMN, Khamees AH. Exploring regional variation: Antioxidant potential
of Lycium barbarum L. samples collected across Iraq. Multidiscip Sci J. 2024.
Gany Yassin S, Mohammed T. Molecular and chemical properties of a common medicinal plants in Iraq. EurAsian J Biosci. 2020; 14(September):7515–26.
Ajeel ZH, Hamad MN. Detection and isolation of some flavonoids and aromatic acid from head(capsule) of cynara scolymus cultivated in Iraq. Iraqi J Pharm Sci. 2020; 29(2):202–13.
Naser EH, Kathem SH. Phytochemical investigation of some bioactive compounds from twigs and leaves of Juniperus oxycedrus L. plant grown in Iraq. Iraqi J Pharm Sci; 2023; 32(3).
Simpson MG. Plant systematics. 2nd edition. Academic Press; 2010. p. 309.
The Plant List. A working list of all plant species: Plumbago. 2017. Available from site: http://www.theplantlist.org/tpl1.1/search?q=Plumbago.
Ferrero V, de Vega C, Stafford GI, Van SJ, Johnson SD. Heterostyly and pollinators in Plumbago auriculata (Plumbaginaceae). South African Journal of Botany. 2009; 10: 1-7.
Tharmaraj RJJM, Antonysamy JM. Screening of bacterial activity of selected Plumbago species against bacterial pathogens. Journal of Microbial Experimentation. 2015; 2:1-7.
Ittiyavirah SP, Paul AS. Gastroprotective effect of plumbagin and ethanolic extract of plumbaginales in experimentally-induced ulcer. Journal of HerbMed Pharmacology. 2016; 5:92-98.
Jose B, Dhanya BP, Silja PK, Krishnan PN, Satheeshkumar K. Plumbago rosea L. A Review on Tissue culture and pharmacological research. International Journal of Pharmaceutical Sciences Review and Research. 2014; 25: 246-256.
Padhye S, Dandawate P, Yusufi M, Ahmad A, Sarkar FH. Perspectives on medicinal properties of plumbagin and its analogs. Medicinal Research Reviews. 2010; 10: 1-28.
Lakshmanan G, Bupesh G, Vignesh A, Sathiyaseelan A, Murugesan K. Micropropagation and anticancer activity of methanolic extract of Plumbago auriculata Lam. International Journal of Advanced Biotechnology and Research. 2016;4: 2001-2011.
Del Rio D, Costa LG, Lean ME, Crozier A. Polyphenols and health: What compounds are involved? Nutr. Metab. Cardiovasc. Dis. 2010; 20:1–6.
Bhuyan DJ, Basu A. Phenolic compounds potential health benefits and toxicity.1st edition. CRC Press; 2017.
Kumara N, Goel N. Phenolic acids: natural versatile molecules with promising therapeutic applications. Biotechnology Reports. 2019; 24.
Arampatzis AS, Pampori A, Droutsa E, Laskari M, Karakostas P, Tsalikis L, Barmpalexis P, Dordas C, Assimopoulou AN. Occurrence of luteolin in the greek flora, isolation of luteolin and its action for the treatment of periodontal diseases. Molecules journal. 2023; 28(3):7720.
Li L, Zhou R, Lv H, Song L, Xue X, Wu L. Inhibitive effect of luteolin on sevoflurane-induced neurotoxicity through activation of the autophagy pathway by HMOX1. ACS Chem. Neurosci. 2021; 12:3314–3322.
Hasym AMO, Nor NM, Adnan LHM, Ahmad NZB, Septama AW, Najihah NN, Lwin OM, Simbak N. Effects of apigenin, luteolin, and quercetin on the natural killer (NK-92) cells proliferation: a potential role as immunomodulatory. Sains Malaysiana. 2021; 50:821–828.
Singh DK, Tousif S, Bhaskar A, Devi A, Negi K, Moitra B, Ranganathan A, Dwivedi VP, Das G. Luteolin as a potential host-directed immunotherapy adjunct to isoniazid treatment of tuberculosis. Plos Pathogen. 2021; 17.
Wang X, Wang L, Dong R, Huang K, Wang C, Gu J, Luo H, Liu K, Wu J, Sun H, Meng Q. Luteolin ameliorates LPS-induced acute liver injury by inhibiting TXNIP-NLRP3 inflammasome in mice. Phytomedicine. 2021; 87:153586.
Xu H, Linn BS, Zhang Y. A Review on the antioxidative and prooxidative properties of luteolin. Ren J. React. Oxygen Species. 2019;7:136–147.
Ganai, Shabir AS, Farooq AB, Zahoor AM, Mudasir AM, Mohd AY, Manzoor A. Phytotherapy Research. 2021; 35: 3509-3532.
Heal HH, Al-Dallee ZT, Khadim EJ. Extraction, isolation and identification of luteolin flavonoid from Vitex pseudonegundo leaves. IOP Conf. Series: Earth and Environmental Science. 2023; 1262.
Srinivasan M, Sudheer AR, Menon VP. Ferulic acid: therapeutic potential through its antioxidant property. J Clin Biochem Nutr. 2007; 40:92–100.
Antonopoulou I, Varriale S, Topakas E, Rova U, Christakopoulos P, Faraco V. Enzymatic synthesis of bioactive compounds with high potential for cosmeceutical application. Appl Microbiol Biotechnol. 2016; 100:6519–43.
Abdlkareem SK, Kadhim EJ. Isolation, identification, and quantification of two compounds from Cassia glauca cultivated in Iraq. Iraqi J Pharm Sci. 2023; 32(3).
Hasan HT, Kadhim EJ. Phytochemical investigation of leaves and seeds of Corchorus olitorius L. cultivated in Iraq. Asian J Pharm Clin Res. 2018; 11(11): 408-417.
Khamees AH, Kadhim EJ. Isolation, characterization and quantification of a pentacyclic triterpinoid compound ursolic acid in Scabiosa palaestina L. distributed in the north of Iraq. Plant science today. 2022; 9(1):178–182.
Al-Jaberi AMZ, Al-Fadal SAM, Abdul-Jalil TZ, Al-Wafi H. HPLC isolation of rutin, hesperidin and quercetin from Ruta chalepensis extract growing in Iraq. Pharmacogn J. 2023;15(4): 606-611.
Khamees AH, Fawzi HA, Sahib HB. Phytochemical investigation and assessment of the hypoglycemic activity of two herbal extracts from selected Iraqi medicinal plants in alloxan-stimulated diabetic rats: a comparative study. F1000 research. 2020; 9:247.
Ngamsuk S, Huang TC, Hsu JL. Determination of phenolic compounds, procyanidins, and antioxidant activity in processed Coffea arabica L. leaves. Foods journal. 2019;8(9):389.
Sarker SD, Latif Z, Gray AI. Natural products isolation. 2nd ed. Totowa, NJ: Humana press; 2005. p. 515.
Hamad MN. Detection and isolation of flavonoids from Calendula officinalis (F. Asteraceae) cultivated in Iraq. Iraqi J Pharm Sci. 2016;25(2):1–6.
Panchal H, Shah M. Development of simultaneous LCMS/MS method for the quantitation of apigenin, luteolin and quercetin in Achillea millefolium extract. Pharm Lett. 2017;12:72-86.
Rajhard S, Hladnik L, Vicente FA, Srcic S, Grilic M, Likozar B. Solubility of luteolin and other polyphenolic compounds in water, nonpolar, polar aprotic and protic solvents by applying FTIR/HPLC. Process journal. 2021; 9(11): 1952.
Kalinowska M, Piekut J, Bruss A, Follet C, Sienkiewicz-Gromiuk J , S´wisłocka R , Rza˛czyn´ ska Z , Lewandowski W. Spectroscopic (FT-IR, FT-Raman, 1H, 13C NMR, UV/VIS), thermogravimetric and antimicrobial studies of Ca(II), Mn(II), Cu(II), Zn(II) and Cd(II) complexes of ferulic acid. HAL open science. 2014; 122: 631-638.
Panchal, Shah. Development of simultaneous LC-MS/MS method for the quantitation of apigenin, luteolin and quercetin in Achillea millefolium extract. Pharm Lett. 2017; 12:72-86.
Sliwka-Kaszynska M, Anusiewicz I, Skruski P. The mechanism of a retro-diels–alder fragmentation of luteolin: theoretical studies supported by electrospray ionization tandem mass spectrometry results. Molecules journal. 2022; 27(3): 1032.
He M, Peng G, Xie F, Hong L, Cao Q. Liquid chromatography–high‑resolution mass spectrometry with ROI strategy for non‑targeted analysis of the in vivo/in vitro ingredients coming from Ligusticum chuanxiong hort. Chromatographia. 2019; 82:1069–1077.
Sinosaki NBM, Tonin APP, Ribeiro MAS, Poliseli CB, Roberto SB, Silveira R,Visentainer JV, Santos OO, Meurerd EC. Structural study of phenolic acids by triple quadrupole mass spectrometry with electrospray ionization in negative mode and H/D isotopic exchange. J. Braz. Chem. Soc. 2019; 00(00): 1-7.
Selim NM, Melk MM, Melek FR, Saleh DO, Sobeh M, El-Hawary SS. Phytochemical profiling and anti-fibrotic activities of Plumbago indica L. and Plumbago auriculata Lam. in thioacetamide-induced liver fibrosis in rats. Scientific reports. 2022;12:9864.
Abdulhussein AJ, Mutlag SH, Khamees AH, Sahib HB. Evaluation of antiangiogenic and antioxidant activity of Harpagophytum procumbens (devil’s claw). Drug invention today. 2018; 10(4).
Hussein AM, Kadum EJ. Identification and isolation of caffeic, chlorogenic and ferulic acids in aerial parts of Capparis spinose wildly grown in Iraq. Iraqi J Pharm Sci. 2020; 29(2).
Sato Y, Itagaki S, Kurokawa T, Ogura J, Kobayashi M, Hirano T, Sugawara M, Iseki K. In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. International Journal of Pharmaceutics. 2011; 403(1-2): 136-138.
Graf E. Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992;13(4):435-48.
Srinivasan M, Sudheer AR, Menon VP. Ferulic acid: therapeutic potential through its antioxidant property. J Clin Biochem Nutr. 2007; 40(2):92-100.
Papuc C, Goran GV, Predescu CN, Nicorescu V, Stefan G. Plant polyphenols as antioxidant and antibacterial agents for shelf-life extension of meat and meat products: classification, structures, sources, and action mechanisms. Comprehensive reviews in food science and food safety. 2017; 16: 1243-1268.
Zang, Igarashi, Li. Anti-diabetic effects of luteolin and luteolin-7-O-glucoside on KK-A y mice. Bioscience, Biotechnology, and Biochemistry. 2016; 80(8):1580-1586.
Sangeetha. Luteolin in the management of type 2 diabetes mellitus. Current research in nutrition and food science journal. 2019; 7(2): 393-398.
Downloads
Published
Issue
Section
License
Copyright (c) 2025 Iraqi Journal of Pharmaceutical Sciences
This work is licensed under a Creative Commons Attribution 4.0 International License.
