Isolation of Ferulic Acid - A Bioactive Phenolic Compound from Pineapple Peel and Evaluation of its In-vitro Anti-inflammatory Potential
Abstract
Fruit wastes and their byproducts may cause serious environmental problems, since it accumulates in agro-industrial yards without having any significant and commercial value. Pineapple(Family - Bromeliaceae) is one of the leading edible tropical fruit produced in the world. Pineapple peel is the massive waste produced by the pineapple processing industry leading to environmental pollution. In this regard, efforts have been made in order to tap the potential of this bio-waste as source of bioactive compounds by isolating, purifying and characterizing known as well as novel secondary metabolites from it and can be used for studying its application in various industries. A phenolic compound namely Ferulic acid is isolated from this bio-waste and its structure has been elucidated by Fourier Transform Infrared (FT-IR) spectroscopy, Liquid Chromatography-Mass Spectrometry (LC-MS), High Performance Liquid Chromatography (HPLC), 1H NMR and 13C Nuclear Magnetic Resonance (NMR) spectra. The anti-inflammatory potential of Ferulic acid was studied in vitro on Lipopolysaccharide (LPS) stimulated Ralph and Williams (RAW) and Tamm-Horsefall Protein-1 (THP-1) cell lines. The levels of pro-inflammatory enzymes such as cyclooxygenase (COX), lipooxygenase (LOX), and myeloperoxidase (MPOX) activities on THP-1 cell lines and the tested compound, exhibited a dose-dependent anti-inflammatory activity. Ferulic acid showed remarkable activity by COX (78.47%) and LOX (78.63%) inhibition in LPS stimulated THP-1 cells at 100 μg/mL. Different concentrations of Ferulic Acid (FER) effectively decreased the MPOX (92.76℅) level in a dose dependent manner and the results were comparable to standard drug Indomethacin. The isolated phenolic compound, ferulic acid, effectively lowered inflammatory cytokines like Tumour Necrosis Factor Alpha (TNF-α), Interleukin-6 (IL-6) and Interleukin-1 Beta (IL-1β) along with prostaglandin E2 and leukotriene C4 and cellular nitrate levels in LPS stimulated RAW cells.
Keywords:
Pineapple peel, Ferulic acid, 1H NMR, 13C NMR, In-vitro anti-inflammatory activityDOI
https://doi.org/10.25004/IJPSDR.2021.130515References
Russell W, Duthie G. Plant secondary metabolites and gut health: The case for phenolic acids. Proceedings of the Nutrition Society. 2011; 70:389-396.
Li AN, Li S, Zhang YJ, Xu XR, Chen YM, Li HB. Resources and biological activities of natural polyphenols. Nutrients. 2014; 6:6020-6047.
Tropea A, Wilson D, La Torre LG, Curto RB, Saugman P, Troy-Davies P, Dugo G, Waldron KW. Bioethanol production from pineapple wastes. Journal of Food Research. 2014; 3:60-70.
Lepoivre M, Chenais B, Yapo A, Lemaire G, Thelander L, Tenu JP. Alterations of ribonucleotide reductase activity following induction of the nitrite-generating pathway in adenocarcinoma cells. Journal of Biological Chemistry. 1990; 265:14143-14149.
Walker MC, Gierse JK. In vitro assays for cyclooxygenase activity and inhibitor characterization. In: Ayoub SS, Flower RJ, Seed MP (Eds). Cyclooxygenases-Methods and Protocols. United States: Humana Press; 2010. p. [131-144].
Axelrod B, Cheesbrough TM, Laakso S. [53] Lipoxygenase from soybeans: EC 1.13. 11.12 Linoleate: oxygen oxidoreductase. In: Lowenstein JM (Ed). Methods in enzymology. United States: Academic Press; 1981 p. [441-451].
Pulli B, Ali M, Forghani R, Schob S, Hsieh KL, Wojtkiewicz G, Linnoila JJ, Chen JW. Measuring myeloperoxidase activity in biological samples. PloS one. 2013; 8:e67976.
Touchstone JC. Practice of thin layer chromatography. 3rd Ed. New York. John Wiley & Sons; 1992.
Kumar N, Pruthi V. Potential applications of ferulic acid from natural sources. Biotechnology Reports. 2014; 4:86-93.
Anuradha V, Srinivas PV, Rao RR, Manjulatha K, Purohit MG, Rao JM. Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L . B ioorganic & M edicinal Chemistry. 2006;14:6820-6826.
Hirun N, Dokmaisrijan S, Tantishaiyakul V. Experimental FTIR and theoretical studies of gallic acid-acetonitrile clusters. Spect rochimica Act a Par t A: Molecular and Biomolecular Spectroscopy. 2012; 86:93-100.
Preetha TS, Mohan SN, Deepthi SR. Chemical Fingerprinting of Spilanthes acmella L . ( Murr.)-An A cutely T hreatened M edicinal Plant of Pharmaceutical Importance by HPLC, FTIR and UV-VIS Spectroscopic Tools. World Journal of Pharmacy and Pharmaceutical Science. 2014; 3:1275-1287.
Le Gall G, Colquhoun IJ, Davis AL, Collins GJ, Verhoeyen ME. Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification. Journal of Agricultural and Food Chemistry. 2003; 51:2447-2456.
Kumar N, Pruthi V. Structural elucidation and molecular docking of ferulic acid from Parthenium hysterophorus possessing COX-2 inhibition activity. 3 Biotech. 2015; 5:541-551.
Sajjadi SE, Shokoohinia Y, Moayedi NS. Isolation and Identification of Ferulic Acid from aerial parts of Kelussia odoratissima Mozaff. Jundishapur Journal of Natural Pharmaceutical Products. 2012; 7:159-162.
Asif M, Khodadadi E. Medicinal uses and chemistry of flavonoid contents of some common edible tropical plants. Archives of Advances in Biosciences. 2013; 4:119-138.
Nagai T, Yukimoto T. Preparation and functional properties of beverages made from sea algae. Food chemistry. 2003; 81:327-332.
Benoit I, Navarro D, Marnet N, Rakotomanomana N, Lesage-Meessen L, Sigoillot JC, Asther M, Asther M. Feruloyl esterases as a tool for the release of phenolic compounds from agro-industrial by-products. Carbohydrate Research. 2006; 341:1820-1827.
Tilay A, Bule M, Kishenkumar J, Annapure U. Preparation of ferulic acid from agricultural wastes: Its improved extraction and purification. Journal of Agricultural and Food Chemistry. 2008; 56: 7644-7648.
Christophoridou S , D ais P, Tseng L H, S praul M . S eparation a nd identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with post column solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR). Journal of Agricultural and Food Chemistry. 2005; 53:4667-4679.
Dussossoy E, Brat P, Bony E, Boudard F, Poucheret P, Mertz C, Giaimis J, Michel A. Characterization, anti-oxidative and anti-inflammatory effects of Costa Rican Noni juice (Morinda citrifolia L.). Journal of ethnopharmacology. 2011; 133:108-115.
Hsu CL, Fang SC, Yen GC. Anti-inflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc. Food and function. 2013; 4:1216-1222.
Sergent T, Piront N, Meurice J, Toussaint O, Schneider YJ. Anti-inflammatory effects of dietary phenolic compounds in an in vitro model of inflamed human intestinal epithelium. Chemico-Biological Interactions. 2010; 188:659-667.
Nakamura M, Omura S. Quercetin regulates the inhibitory effect of monoclonal non-specific suppressor factor β on tumor necrosis factor-α production in LPS-stimulated macrophages. Bioscience, Biotechnology and Biochemistry. 2008; 72:1915-1920.
Anitha P, Priyadarsini RV, Kavitha K, Thiyagarajan P, Nagini S. Ellagic a cid c oordinately a ttenuates W nt/β-catenin a nd N F-κB signaling pathways to induce intrinsic apoptosis in an animal model of oral oncogenesis. European Journal of Nutrition. 2013; 52: 75-84.
Maxia A, Sanna C, Frau MA, Piras A, Karchuli MS, Kasture V. Anti-inflammatory Activity of Pistacia lentiscus essential oil: Involvement of IL-6 and TNF-α. Natural Product Communications. 2011; 6:1543-1544.
Mease PJ. Tumour necrosis factor (TNF) in psoriatic arthritis: pathophysiology and treatment with TNF inhibitors. Annals of the Rheumatic Diseases. 2002; 61:298-304.
Zhao BT, Hung ND, Lee JH, Min BS, Woo MH. Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells. Bioorganic and Medicinal Chemistry letters. 2017; 27:524-529.
Deepa J, Aleykutty NA, Jyoti H. Comparative evaluation of in vitro anti-inflammatory activity of Psidium guajava and Syzygium cumini leaves. International Journal of Ayurveda and Pharma Research. 2017; 5:33-41.
Tian R, Ding Y, Peng YY, Lu N. Inhibition of myeloperoxidase-and neutrophil-mediated hypochlorous acid formation in vitro and endothelial cell injury by (−)-epigallocatechin gallate. Journal of Agricultural and Food chemistry. 2017; 65:3198-3203.
Published
Abstract Display: 563 
PDF Downloads: 539 
