PHYTOCHEMICAL SCREENING AND BIOLOGICAL EVALUATION OF DYPSIS LEPTOCHEILOS LEAVES EXTRACT AND MOLECULAR DOCKING STUDY OF THE ISOLATED COMPOUNDS
DOI:
https://doi.org/10.22159/ijpps.2020v12i11.39481Keywords:
Antimicrobial, Antioxidant, Cytotoxicity, Docking, Dypsis leptocheilos, PolyphenolicAbstract
Objective: phytochemical investigation of the ethyl acetate fraction (EAF) of 80% aqueous methanol extract (AME) of Dypsis leptocheilos leaves, in addition to evaluation of the antioxidant, cytotoxic and antimicrobial activities of the AME and EAF. Docking was used to predict and understand cytotoxicity of the isolated compounds.
Methods: The ethyl acetate fraction (EAF) of Dypsis leptocheilos leaves was subjected to different chromatographic separation techniques. Structures of the isolated compounds were established by different spectroscopic techniques (1H/13C NMR). Antioxidant activity was evaluated by DPPH assay, while cytotoxicity was evaluated by MTT cell viability assay. Antimicrobial activity was evaluated by agar diffusion method. The docking study was conducted using Auto Dock Vina; the estrogen receptor (PDB 5t92) was used as a receptor for the docking.
Results: Chromatographic separation techniques were led to the isolation of five phenolic compounds; these compounds were identified to be apigenin 8-C-β-D-glucopyranoside (Vitexin) (1), apigenin 6-C-β-D-glucopyranoside (Isovitexin) (2), luteolin 7-O-β-D-glucopyranoside (3), luteolin 8-C-β-D-glucopyranoside (Orientin) (4), luteolin 6-C-β-D-glucopyranoside (Isoorientin) (5). They were isolated and identified for the first time from this plant species. The AME and EAF showed moderate activity against Gram positive and Gram negatvie bacteria, while both of them showed similar and powerful antioxidant activity with SC50 = 12.8±0.56 µg/ml and SC50 = 17±0.77 µg/ml respectively, compared to ascorbic (reference drug) SC50 = 14.2±0.35 µg/ml. The EAF showed higher cytotoxic activity on the MCF-7 cells (human breast cancer cell line), with IC50 = 12.3 ± 1.82 µg/ml, compared to Vinblastine Sulfate (reference drug). All isolated compounds showed good binding affinity to the estrogen receptors existed in the MCF-7 cell.
Conclusion: Five phenolic compounds were isolated for the first time from the EAF of Dypsis leptocheilos leaves. The AME and EAF extracts showed variable antioxidant, antimicrobial and cytotoxic activities.
Downloads
References
Pavithr S, Sekar T. Phytochemical profiling, free-radical scavenging and anti-inflammatory activities of meliosma simplicifolia (L.). Int J Pharm Pharm Sci 2020;12:62-8.
Dransfield J, Beentje H. The palms of madagascar, royal botanic gardens, kew and the international palm society; 1995.
Imtilemla A, Bareh V, Barbhuiya SB, Sailo L. Preliminary phytochemical screening and in vitro antioxidant activity of the methanolic extract of Lindernia ruellioides (Colsm.) pennell. Asian J Pharm Clin Res 2020;13:141-6.
Lengauer T, Rarey M. Computational methods for biomolecular docking. Curr Opin Struct Biol 1996;6:402-6.
Meng EC, Shoichet BK, Kuntz ID. Automated docking with grid‐based energy evaluation. J Comput Chem 1992;13:505-24.
Mabry TJ, Markham KR, Thomas MB. Ultraviolet spectra of isoflavones, flavanones and dihydroflavonols in the systematic identification of flavonoids. Springer Berlin Heidelberg; 1970. p. 165-226.
Yen GC, Duh PD. Scavenging effect of methanol extracts of peanut hulls on free radical and active oxygen species. J Agric Food Chem 1994;42:629-32.
Hindler JA, Howard BJ, Keiser JF. Antimicrobial agents and susceptibility testing. In: Howard BJ. (Editor). Clinical and Pathogenic Microbiology. Mosby-Year Book Inc. St. Louis, MO, USA; 1994.
Mosmann T. Rapid colorimetric assay for cellular growth and survival application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.
Gomha SM, Riyadh SM, Mahmmoud EA, Elaasser MM. Synthesis and anticancer activities of thiazoles, 1, 3-thiazines, and thiazolidine using chitosan-grafted-poly (vinyl pyridine) as basic catalyst. Heterocycles 2015;91:1227-43.
Trott O, Olson AJ. Auto dock vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem 2010;31:455-61.
Abagyan R, Totrov M, Kuznetsov D. ICM-a a new method for protein modeling and design: Applications to docking and structure prediction from the distorted native conformation. J Comput Chem 1994;15:488-506.
Baxter J. Local optima avoidance in depot location. J Oper Res Soc 1981;32:815-9.
Blum A, Blesa M, Sampels M. Hybrid metaheuristics: an emerging approach to optimization (Eds.). Berlin, Heidelberg: Springer-Verlag; 2008. p. 261-89.
Nassar MI, Gaara AH, Marzouk MS, El-Din E, El-Khrisy AM. Anew gentisic acid glycoside and C-glycosyl flavones from Erythrina indica with the antioxidant activity evaluation. Bull Fac Pharm Cairo Univ 2003;41:207-9.
El-Toumy SA, Omara EA, Nada SA, Bermejo J. Flavone C-glycosides from Montanoa bipinnatifida stems and evaluation of hepatoprotective activity of extract. JMPR 2011;5:1291-6.
Kubacey TM, Haggag EG, El-Toumy SA, Ahmed AA, El-Ashmawy IM, Youns MM. Biological activity and flavonoids from Centaurea alexanderina leaf extract. J Pharm Res 2012;5:3352-61.
Li H, Zhou P, Yang Q, Shen Y, Deng J, Li L, et al. Comparative studies on anxiolytic activities and flavonoid compositions of Passiflora edulis ‘edulis’ and Passiflora edulis ‘flavicarpa’. J Ethnopharmacol 2011;133:1085-90.
Choo CY, Sulong NY, Man F, Wong TW. Vitexin and isovitexin from the leaves of Ficus deltoidea with in vivo α-glucosidase inhibition. J Ethnopharmacol 2012;142:776-81.
Mohamed TK, Kamal AM, Nassar MI, Ahmed MA, Haggag EG, Ezzat HA. Phenolic contents of Gleditsia triacanthos leaves and evaluation of its analgesic anti-inflammatory, hepatoprotective and antimicrobial activities. Life Sci J 2013;10:3445-66.
Agrawal PK, Thakur RS, Bansal MC. In 13C NMR of flavonoids agrawal (ed) Elsevier, New York; 1989;6:287-93.
Zhang Y, Jiao J, Liu C, Wu X, Zhang Y. Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography. Food Chem 2008;107:1326-36.
Sezik E, Aslan M, Yesilada E, Ito S. Hypoglycaemic activity of Gentiana olivieri and isolation of the active constituent through bioassay-directed fractionation techniques. Life Sci J 2005;76:1223-38.
Chiruvella KK, Mohammed A, Dampuri G, Ghanta RG, Raghavan SC. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int J Biomed Sci 2007;3:269.
Chandrika M, Chellaram M. Efficacy of antioxidation and anti-inflammation of the leaf extracts of borreria hispida. Int J Pharm Pharm Sci 2016;8:369-72.
Ibrahim RR, Ibrahim HA, Shabana SS, El-Hosari DG, Ali SA, Mahgoub S, et al. New phenolic compounds from calothamnus quadrifidus R. Br. aerial parts and their antioxidant activity. Nat Prod Res 2020;8:1-9.
Wei Y, Li J, Qing J, Huang M, Wu M, Gao F, et al. Discovery of novel hepatitis c virus NS5B polymerase inhibitors by combining random forest, multiple e-pharmacophore modeling and docking. PLoS ONE 2016;11(Suppl 2):e0148181.
Published
How to Cite
Issue
Section
