Antibacterial and antioxidant activity of compounds from Citrus sinensis peels and in silico molecular docking study

Year 2023, Volume: 10 Issue: 3, 437 - 458, 27.08.2023

Raey Yohanes , Teshome Geremew , Tarekegn Tafese Milkyas Endale Annisa

https://doi.org/10.21448/ijsm.1180610

Cited By: 3

Abstract

The increasing prevalence of drug resistance, adverse side effects of existing antibiotics, and the resurgence of previously known infections have necessitated the search for new, safe, and effective antimicrobial agents. The peels of Citrus sinensis (300 g) were extracted using maceration and ultrasonic-assisted extraction methods with ethanol, resulting in yields of 20.99 g and 11.5 g (7%, 7.5%), respectively. Silica gel column chromatographic separation of the ethanol extract yielded N-(1,3,4,5-tetrahydroxydecan-2-y1)octanamide (1), decanoic acid (2), β-sitosterol-3-O-β-D-glucopyranoside derivative (3), and (z)-ethyl tetradec-7-enoate (4). GC-MS analysis of the essential oil detected 7 chemical components accounting for 99.84% of the total composition of which limonene was found to be the predominant constituent (87.5%). In vitro antibacterial tests revealed promising zones of inhibition by ethanol extract (12.67±0.58 mm, at 150 mg/mL), compound 4 (15.67±2.88 mm, at 6 mg/mL), and compound 1 (12.00±0.00 mm, at 6 mg/mL) against E. faecalis, S. typhimurium, and P. aeruginosa, respectively, compared to gentamicin (13.00±1.73 mm, 18.00±1.00 mm, and 16.67±1.15 mm, respectively at 10 µg/mL). DPPH radical scavenging activity indicated that compound 1 exhibited an IC50 value of 0.05 mg/mL, compared to ascorbic acid's 0.016 mg/mL. In silico molecular docking studies revealed that compounds 1 and 3 had the lowest scoring poses against E. coli DNA gyrase B enzyme, human peroxiredoxin 5, and S. aureus pyruvate kinase, respectively. These findings support traditional applications of Citrus peels in treating infectious diseases, particularly against Gram-positive strains, and highlight their potential use as antibacterial ingredients in cosmetics.

Keywords

Citrus sinesis, Antimicrobial activity, Antioxidant activity, Molecular docking, Essential oils

References

• Angew O.N. (2007). High concentration of vitamin C in orange, Functional foods. Trends in Food Science and Technology, 30, 19-21.
• Akinyemi, K.O., Oluwa, O.K., Omomigbehin, E.O., Nuamsetti, T., Dechayuenyong, P., Tantipaibulvut, S., Mohanka, R., Dqg, R., Ri, Q., Wudfwv, P., Materials, A., Pdlqwdlqlqj, D. E., Vdpsohv, W. K. H., Dq, L. Q., Dq, R., Fhqwulixjhg, Z., Usp, D. W., Fhqwulixjh, X., Tfs, E., … Divakar, D. D. (2016). Antibacterial Activity of Citrus sinensis ( Orange ) Peel on Bacterial Isolates from Wound. BMC Complementary and Alternative Medicine, 3(1), 3374-3381.
• Almas, K., Skaug, N., & Ahmad, I. (2005). An in vitro antimicrobial comparison of miswak extract with commercially available non-alcohol mouthrinses. International Journal of Dental Hygiene, 3(1), 18-24.
• Ayukekbong, J.A., Ntemgwa, M., & Atabe, A.N. (2017). The threat of antimicrobial resistance in developing countries: Causes and control strategies. Antimicrobial Resistance and Infection Control, 6(1), 1–8.
• Azam, S.S., & Abbasi, S.W. (2013). Molecular docking studies for the identification of novel melatoninergic inhibitors for acetylserotonin-O-methyltransferase using different docking routines. Theoretical Biology and Medical Modelling, 10(1), 1-16.
• Baba, J., Mohammed, S.B., Ya’aba, Y., & Umaru, F.I. (2018). Antibacterial Activity of Sweet Orange Citrus sinensis on some Clinical Bacteria Species Isolated from Wounds. Journal of Family Medicine and Community Health, 5(4), 1154.
• Burt S. (2004). Essential oils: their antibacterial properties and potential applications in foods-a review. International Journal of Food Microbiology, 94(3), 223-53.
• Bourgou, S., Rahali, F.Z., Ourghemmi, I., Tounsi, M.S. (2012). Changes of peel essential oil composition of four tunisian citrus during fruit maturation. The Scientific World Journal, 2012, 1-10.
• Crowell, P.L., Gould, M.N. (1994). Chemoprevention and therapy of cancer by d-limonene. Critical Reviews in Oncogenesis.5(1), 1-22.
• Chee, H.Y., Kim, H., Lee, M.H. (2009). In vitro Antifungal Activity of Limonene against Trichophyton rubrum. Mycobiology. 37(3), 243-6.
• Edogbanya, P.R.O, Suleiman, M.O., Olorunmola, J.B., Oijagbe, (2019). Comparative study on the antimicrobial effects of essential oils from peels of three citrus fruits. MOJ Biololgy and Medicine, 4(2), 49-54.
• Etebu, E., & Nwauzoma, A.B. (2014). A review on sweet orange (Citrus sinensis) health, diseases and management. American Journal of Research Communication, 2(2), 33–70.
• Friedman, M., Henika, P.R., & Mandrell, R.E. (2002). Bactericidal Activities of Plant Essential Oils and Some of Their Isolated Constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. Journal of Food Protection, 65(10), 1545-1560.
• Galma, W., Endale, M., Getaneh, E., Eswaramoorthy, R., Assefa, T., Melaku, Y. (2021). Molecular docking analysis, antibacterial and antioxidant activities of extracts and isolated compounds from the roots extract of Cucumis prophetarum, BMC chemistry, 15(32), 1-17.
• Hamid, A.A., Aiyelaagbe, O.O., Negi, A.S., Kaneez, F., Luqman, S., Oguntoye, S.O., Kumar, S. B., & Zubair, M. (2019). Isolation and antiproliferative activity of triterpenoids and fatty acids from the leaves and stem of Turraea vogelii Hook. f. ex benth. Natural Product Research, 33(2), 296-301.
• Hanuš, L.O., Rosenthal, D., Řezanka, T., Dembitsky, V.M., Moussaief, A.(2008). Fast and easy GC/MS identification of myrrh resins. Pharmaceutical Chemsitry Journal, 42(12), 719-20.
• Hodek, P., Trefil, P., & Stiborová, M. (2002). Flavonoids-potent and versatile biologically active compounds interacting with cytochromes P450. Chemico-Biological Interactions, 139(1), 1-21.
• Koehn, F.E., & Carter, G.T. (2005). The evolving role of natural products in drug discovery. Nature Reviews Drug Discovery, 4(3), 206-220.
• Mursiti, S., Lestari, N. A., Febriana, Z., Rosanti, Y.M., Ningsih, T.W. (2019). The activity of Limonene from sweet orange peel (Citrus sinesis L.) extract as a natural insecticide controller of bedbugs (Cimex cimicidae). Oriental Journal of Chemistry, 35(4), 1420-1425.
• Nisha, N.S., Swedha, A.A., Rahaman, J., Basheer J., Sayeed A.(2013). Antibacterial activity ofCitrus sinensis peel against enteric pathogens. International Journal of Pharmaceutical Research and Bio-Science, 2(5), 1-13.
• Nishibe, S., Tamayama, Y., Sasahara, M., & Andary, C. (1995). A phenylethanoid glycoside from Plantago asiatica. Phytochemistry, 38(3), 741-743.
• Osarumwense, P.O. (2017). Anti-inflammatory Activity of Methanoilc and Ethanolic Extracts of Citrus sinensis peel (L) Osbeck on Carrageenan induced Paw Oedema in Wistar rats. Journal of Applied Sciences and Environmental Management, 21(6), 1223.
• Peshin, T., Kar. H.K. (2017). Isolation and Characterization of β-Sitosterol-3-O-βD-glucoside from the Extract of the Flowers of Viola odorata, British Journal of Pharmaceutical Research, 16(4), 1-8.
• Riffel, A., Medina, L.F., Stefani, V., Santos, R.C., Bizani, D., & Brandelli, A. (2002). In vitro antimicrobial activity of a new series of 1,4-naphthoquinones. Brazilian Journal of Medical and Biological Research, 35(7), 811-818.
• Safdar, M.N., Kausar, T., Jabbar, S., Mumtaz, A., Ahad, K., & Saddozai, A.A. (2017). Extraction and quantification of polyphenols from kinnow ( Citrus reticulate L.) peel using ultrasound and maceration techniques. Journal of Food and Drug Analysis, 25(3), 488-500.
• Saini, A., Panesar, P.S., & Bera, M.B. (2019). Comparative Study on the Extraction and Quantification of Polyphenols from Citrus Peels Using Maceration and Ultrasonic Technique. Current Research in Nutrition and Food Science Journal, 7(3), 678-685.
• Shetty, S.B., Mahin-Syed-Ismail, P., Varghese, S., Thomas-George, B., Kandathil-Thajuraj, P., Baby, D., Haleem, S., Sreedhar, S., & Devang-Divakar, D. (2016). Antimicrobial effects of Citrus sinensis peel extracts against dental caries bacteria: An in vitro study. Journal of Clinical and Experimental Dentistry, 8(1), 71-77.
• Shimada, T. (2006). Salivary proteins as a defense against dietary tannins. Journal of Chemical Ecology, 32(6), 1149-1163.
• Sofowora, A. (1993). Recent trends in research into African medicinal plants. Journal of Ethnopharmacology, 38(2-3), 197-208.
• Sofowora, A. (1996). Research on Medicinal Plants and Traditional Medicine in Africa. The Journal of Alternative and Complementary Medicine, 2(3), 365-372.
• Suja, D., Bupesh, G., Nivya, R. Mohan, V., Ramasamy, P., Muthiah, N.S., Arul, A.E., Meenakumari, K., Prabu, K. (2017). Phytochemical Screening, Antioxidant, Antibacterial Activities of Citrus limon and Citrus Sinensis Peel Extracts. International Journal of Pharmacognosy & Chinese Medicine, 1(2), 1-7.
• Tripoli, E., Guardia, M. La, Giammanco, S., Majo, D. Di, & Giammanco, M. (2007). Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review. Food Chemistry, 104(2), 466-479.
• Uraku, A.J., Uraku, O.H., Nwankwo, V. O.U, Okoye, C.J., Ozioma, P.E., Edenta, C., Ezeali, C., (2020). Medicinal prospective of Citrus limon and Citrus sinensis peels essential oil by Gas Chromatography/Mass Spectrometry (GC/MS) compositional analysis. Journal of Bioscience and Biotechnology Discovery, 5(3), 53-59.
• Williams, C.A., Harborne, J.B., & Clifford, H.T. (1973). Negatively charged flavones and tricin as chemosystematic markers in the palmae. Phytochemistry, 12(10), 2417-2430.
• Wong, S.E., & Lightstone, F.C. (2011). Accounting for water molecules in drug design. Expert Opinion on Drug Discovery, 6(1), 65-74.
• Young, W.K., Ji, K.M., Young, C.B., Yeon, B.D., Seong, K.L., Seul, M.C., Duck, S.L., Myung, C.C., Kyungsil, Y., Hyung, S.K., (2013). Safety evaluation and risk assessment of d-limonene. Journal of Toxicology and Enviromental Health Part B., 16, 17-38.