GC–MS screening of the phytochemical composition of Ziziphus honey: ADME properties and in vitro/in silico study of its antimicrobial activity

References

• Abdelgawad, M. A., Oh, J. M., Parambi, D. G., Kumar, S., Musa, A., Ghoneim, M. M., Nayl, A. A., El-Ghorab, A. H., Ahmad, I., Patel, H., Kim, H., & Mathew, B. (2022). Development of bromo-and fluoro-based α, β-unsaturated ketones as highly potent MAO-B inhibitors for the treatment of Parkinson’s disease. Journal of Molecular Structure, 1266, 133545. https://doi.org/10.1016/j.molstruc.2022.133545
   Web of Science ®Google Scholar
• Ahmad, I., Pawara, R., & Patel, H. (2022). In silico toxicity investigation of Methaqualone’s conjunctival, retinal, and gastrointestinal hemorrhage by molecular modelling approach. Molecular Simulation, 48(18), 1639–1649. https://doi.org/10.1080/08927022.2022.2113412
   Web of Science ®Google Scholar
• Al-Ghamdi, A. A., & Ansari, M. J. (2021). Biological and therapeutic roles of Saudi Arabian honey: A comparative review. Journal of King Saud University - Science, 33(2), 101329. https://doi.org/10.1016/j.jksus.2020.101329
   Web of Science ®Google Scholar
• Ali, H., Khan, S., Ullah, R., & Khan, B. (2020). Fluorescence fingerprints of Sidr honey in comparison with uni/polyfloral honey samples. European Food Research and Technology, 246(9), 1829–1837. https://doi.org/10.1007/s00217-020-03536-6
   Web of Science ®Google Scholar
• Aljuhani, A., Ahmed, H. E. A., Ihmaid, S. K., Omar, A. M., Althagfan, S. S., Alahmadi, Y. M., Ahmad, I., Patel, H., Ahmed, S., Almikhlafi, M. A., El-Agrody, A. M., Zayed, M. F., Turkistani, S. A., Abulkhair, S. H., Almaghrabi, M., Salama, S. A., Al-Karmalawy, A. A., & Abulkhair, H. S. (2022). In vitro and computational investigations of novel synthetic carboxamide-linked pyridopyrrolopyrimidines with potent activity as SARS-CoV-2-M Pro inhibitors. RSC Advances, 12(41), 26895–26907. https://doi.org/10.1039/d2ra04015h
   PubMed Web of Science ®Google Scholar
• Almasaudi, S. B., Al-Nahari, A. A. M., Abd El-Ghany, E. S. M., Barbour, E., Al Muhayawi, S. M., Al-Jaouni, S., Azhar, E., Qari, M., Qari, Y. A., & Harakeh, S. (2017). Antimicrobial effect of different types of honey on Staphylococcus aureus. Saudi Journal of Biological Sciences, 24(6), 1255–1261. https://doi.org/10.1016/j.sjbs.2016.08.007
   PubMed Web of Science ®Google Scholar
• Alqurashi, A. M., Masoud, E. A., & Alamin, M. A. (2013). Antibacterial activity of Saudi honey against Gram negative bacteria. Journal of Microbiology and Antimicrobials, 5(1), 1–5. https://doi.org/10.5897/JMA2012.0235
   Google Scholar
• Alsantali, R., Mughal, E., Naeem, N., Alsharif, M., Sadiq, A., Ali, A., Jassas, R., Javed, Q., Javid, A., Sumrra, S. H., Alsimaree, A., Zafar, M., Asghar, B., Altass, H., Moussa, Z., & Ahmed, S. (2022). Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies. Journal of Molecular Structure, 1251, 131933. https://doi.org/10.1016/j.molstruc.2021.131933
   Web of Science ®Google Scholar
• Al-Sayaghi, A. M., Al-Kabsi, A. M., Abduh, M. S., Saghir, S. A. M., & Alshawsh, M. A. (2022). Antibacterial mechanism of action of two types of honey against Escherichia coli through interfering with bacterial membrane permeability, inhibiting proteins, and inducing bacterial DNA damage. Antibiotics, 11(9), 1182. https://doi.org/10.3390/antibiotics11091182
   Google Scholar
• Alshaye, N. A., Mughal, E. U., Elkaeed, E. B., Ashraf, Z., Kehili, S., Nazir, Y., Naeem, N., Abdul Majeed, N., & Sadiq, A. (2022). Synthesis and biological evaluation of substituted aurone derivatives as potential tyrosinase inhibitors: In vitro, kinetic, QSAR, docking and drug-likeness studies. Journal of Biomolecular Structure and Dynamics, 1–16. https://doi.org/10.1080/07391102.2022.2132296
   Google Scholar
• Ashraf, J., Mughal, E. U., Sadiq, A., Bibi, M., Naeem, N., Ali, A., Massadaq, A., Fatima, N., Javid, A., Zafar, M. N., Khan, B. A., Nazar, M. F., Mumtaz, A., Tahir, M. N., & Mirzaei, M. (2021). Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: Synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies. Journal of Biomolecular Structure & Dynamics, 39(18), 7107–7122. https://doi.org/10.1080/07391102.2020.1805364
   PubMed Web of Science ®Google Scholar
• Ayipo, Y. O., Yahaya, S. N., Babamale, H. F., Ahmad, I., Patel, H., & Mordi, M. N. (2021). β-Carboline alkaloids induce structural plasticity and inhibition of SARS-CoV-2 nsp3 macrodomain more potently than remdesivir metabolite GS-441524: Computational approach. Turkish Journal of Biology = Turk Biyoloji Dergisi, 45(4), 503–517. https://doi.org/10.3906/biy-2106-64
   PubMed Web of Science ®Google Scholar
• Azonwade, F. E., Paraïso, A., Agbangnan Dossa, C. P., Dougnon, V. T., N’tcha, C., Mousse, W., & Baba-Moussa, L. (2018). Physicochemical characteristics and microbiological quality of honey produced in Benin. Journal of Food Quality, 2018, 1–13. https://doi.org/10.1155/2018/1896057
   Web of Science ®Google Scholar
• Badr, S. F., El-Sherif, N. A., Shabana, I. I., El-Deeb, M., & Al-Shinqiti, F. Y. M. (2020). Evaluation of genetic variation, antioxidant and antibacterial activities of two Sidr varieties in Medina. Pakistan Journal of Pharmaceutical Sciences, 33(1)
   PubMed Web of Science ®Google Scholar
• Badr, S. F., El-Sherif, N. A., Shabana, I., El-Deeb, M., & Al-Shinqiti, F. Y. M. (2020). Evaluation of genetic variation, antioxidant and antibacterial activities of two Sidr varieties in Medinadoi. Pakistan Journal of Pharmaceutical Sciences, 33(1), 61–69. https://doi.org/10.36721/PJPS.2020.33.1.REG.061-069.1
   PubMed Web of Science ®Google Scholar
• Badraoui, R., Rebai, T., Elkahoui, S., Alreshidi, M., N. Veettil, V., Noumi, E., A. Al-Motair, K., Aouadi, K., Kadri, A., De Feo, V., & Snoussi, M. (2020). Allium subhirsutum L. as a potential source of antioxidant and anticancer bioactive molecules: HR-LCMS phytochemical profiling, in vitro and in vivo pharmacological study. Antioxidants, 9(10), 1003. https://doi.org/10.3390/antiox9101003
   Web of Science ®Google Scholar
• Bax, B. D., Chan, P. F., Eggleston, D. S., Fosberry, A., Gentry, D. R., Gorrec, F., Giordano, I., Hann, M. M., Hennessy, A., Hibbs, M., Huang, J., Jones, E., Jones, J., Brown, K. K., Lewis, C. J., May, E. W., Saunders, M. R., Singh, O., Spitzfaden, C. E., … Gwynn, M. N. (2010). Type IIA topoisomerase inhibition by a new class of antibacterial agents. Nature, 466(7309), 935–940. https://doi.org/10.1038/nature09197
   PubMed Web of Science ®Google Scholar
• Bharadwaj, K. K., Ahmad, I., Pati, S., Ghosh, A., Sarkar, T., Rabha, B., Patel, H., Baishya, D., Edinur, H. A., Abdul Kari, Z., Ahmad Mohd Zain, M. R., & Wan Rosli, W. I. (2022). Potent bioactive compounds from seaweed waste to combat cancer through bioinformatics investigation. Frontiers in Nutrition, 9, 1-16. https://doi.org/10.3389/fnut.2022.889276
   PubMed Web of Science ®Google Scholar
• Boulaamane, Y., Ahmad, I., Patel, H., Das, N., Britel, M. R., & Maurady, A. (2023). Structural exploration of selected C6 and C7-substituted coumarin isomers as selective MAO-B inhibitors. Journal of Biomolecular Structure and Dynamics, 41(6), 2326–2340.
   PubMed Web of Science ®Google Scholar
• Chaudhari, B., Patel, H., Thakar, S., Ahmad, I., & Bansode, D. (2022). Optimizing the Sunitinib for cardio-toxicity and thyro-toxicity by scaffold hopping approach. In Silico Pharmacology, 10(1), 10. https://doi.org/10.1007/s40203-022-00125-1
   PubMedGoogle Scholar
• Cianciosi, D., Forbes-Hernández, T., Afrin, S., Gasparrini, M., Reboredo-Rodriguez, P., Manna, P., Zhang, J., Bravo Lamas, L., Martínez Flórez, S., Agudo Toyos, P., Quiles, J., Giampieri, F., & Battino, M. (2018). Phenolic compounds in honey and their associated health benefits: A review. Molecules, 23(9), 2322. https://doi.org/10.3390/molecules23092322
   PubMed Web of Science ®Google Scholar
• Cohen, F. L., & Tartasky, D. (1997). Microbial resistance to drug therapy: A review. American Journal of Infection Control, 25(1), 51–64. https://doi.org/10.1016/s0196-6553(97)90054-7
   PubMed Web of Science ®Google Scholar
• Ekhtelat, M., Ravaji, K., & Parvari, M. (2016). Effect of Iranian Ziziphus honey on growth of some foodborne pathogens. Journal of Natural Science, Biology, and Medicine, 7(1), 54–57. https://doi.org/10.4103/0976-9668.175069
   PubMedGoogle Scholar
• Enany, M. E., Algammal, A. M., Shagar, G. I., Hanora, A. M., Elfeil, W. K., & Elshaffy, N. M. (2018). Molecular typing and evaluation of Sidr honey inhibitory effect on virulence genes of MRSA strains isolated from catfish in Egypt. Pakistan Journal of Pharmaceutical Sciences, 31(5), 1865–1870.
   PubMed Web of Science ®Google Scholar
• Enany, M., Al-Gammal, A., Hanora, A., Shagar, G., & El Shaffy, N. (2015). Sidr honey inhibitory effect on virulence genes of MRSA strains from animal and human origin. Suez Canal Veterinary Medical Journal. SCVMJ, 20(2), 23–30. https://doi.org/10.21608/scvmj.2015.64562
   Google Scholar
• Farhan, M. M., Guma, M. A., Rabeea, M. A., Ahmad, I., & Patel, H. (2022). Synthesizes, characterization, molecular docking and in vitro bioactivity study of new compounds containing triple beta lactam rings. Journal of Molecular Structure, 1269, 133781. https://doi.org/10.1016/j.molstruc.2022.133781
   Web of Science ®Google Scholar
• Feknous, N., & Boumendjel, M. (2022). Natural bioactive compounds of honey and their antimicrobial activity. Czech Journal of Food Sciences, 40(3), 163–178. https://doi.org/10.17221/247/2021-CJFS
   Web of Science ®Google Scholar
• Gatsing, D., Tchakoute, V., Ngamga, D., Kuiate, J. R., Tamokou, J. D. D., Nji, N. B., Tchouanguep, F. M., & Fodouop, S. P. (2009). In vitro antibacterial activity of Crinum Purpurascens herb leaf extract against the Salmonella species causing typhoid fever and its toxicological evaluation. Iranian Journal of Medical Sciences,34(2), 126–136.
   Google Scholar
• Ghramh, H. A., Ibrahim, E. H., & Kilany, M. (2020). Study of anticancer, antimicrobial, immunomodulatory, and silver nanoparticles production by Sidr honey from three different sources. Food Science & Nutrition, 8(1), 445–455. https://doi.org/10.1002/fsn3.1328
   PubMed Web of Science ®Google Scholar
• Hamadou, W. S., Bouali, N., Badraoui, R., Hadj Lajimi, R., Hamdi, A., Alreshidi, M., Patel, M., Adnan, M., Siddiqui A. J., Noumi E., Rao Pasupuleti V., & Snoussi, M. (2022). Chemical composition and the anticancer, antimicrobial, and antioxidant properties of Acacia honey from the Hail Region: The in vitro and in silico investigation. Evidence-Based Complementary and Alternative Medicine, 2022, 1518511. https://doi.org/10.1155/2022/1518511.
   PubMed Web of Science ®Google Scholar
• Hegazi, A. G., Al Guthami, F. M., Ramadan, M. F., Al Gethami, A. F., Craig, A. M., & Serrano, S. (2022). Characterization of Sidr (Ziziphus spp.) honey from different geographical origins. Applied Sciences, 12(18), 9295. https://doi.org/10.3390/app12189295
   Google Scholar
• Hiller, C. X., Hübner, U., Fajnorova, S., Schwartz, T., & Drewes, J. E. (2019). Antibiotic microbial resistance (AMR) removal efficiencies by conventional and advanced wastewater treatment processes: A review. The Science of the Total Environment, 685, 596–608. https://doi.org/10.1016/j.scitotenv.2019.05.315
   PubMed Web of Science ®Google Scholar
• Israili, Z. H. (2014). Antimicrobial properties of honey. American Journal of Therapeutics, 21(4), 304–323. https://doi.org/10.1097/MJT.0b013e318293b09b
   PubMed Web of Science ®Google Scholar
• Kikiowo, B., Ogunleye, A. J., Inyang, O. K., Adelakun, N. S., Omotuyi, O. I., Metibemu, D. S., David, T. I., Oludoyi, O. O., & Ijatuyi, T. T. (2020). Flavones scaffold of Chromolaena odorata as a potential xanthine oxidase inhibitor: Induced Fit Docking and ADME studies. BioImpacts : BI, 10(4), 227–234. https://doi.org/10.34172/bi.2020.29
   PubMed Web of Science ®Google Scholar
• Kikiowo, B., Ogunleye, A. J., Iwaloye, O., Ijatuyi, T. T., Adelakun, N. S., & Alashe, W. O. (2021). Induced fit docking and automated QSAR studies reveal the ER-α inhibitory activity of Cannabis Sativa in breast cancer. Recent Patents on anti-Cancer Drug Discovery, 16(2), 273–284. https://doi.org/10.2174/1574892816666210201115359
   PubMed Web of Science ®Google Scholar
• Laallam, H., Boughediri, L., Bissati, S., Menasria, T., Mouzaoui, M. S., Hadjadj, S., Hammoudi, R., & Chenchouni, H. (2015). Modeling the synergistic antibacterial effects of honey characteristics of different botanical origins from the Sahara Desert of Algeria. Frontiers in Microbiology, 6, 1239. https://doi.org/10.3389/fmicb.2015.01239
   PubMed Web of Science ®Google Scholar
• Lin, T., Huang, L., Cheng, N., Wang, Y., Ning, Z., Huang, S., Wu, Y., Chen, T., Su, S., & Lin, Y. (2022). The in vitro and in vivo antibacterial activities of uniflorous honey from a medicinal plant, Scrophularia ningpoensis Hemsl., and characterization of its chemical profile with UPLC-MS/MS. Journal of Ethnopharmacology, 296, 115499. https://doi.org/10.1016/j.jep.2022.115499
   PubMed Web of Science ®Google Scholar
• Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23(1-3), 3–25. ‏ https://doi.org/10.1016/S0169-409X(96)00423-1
   Web of Science ®Google Scholar
• Metwali, Z., Abdalla, N., & El-Barrani, R. (2014). A natural alternative to conventional antibiotics. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 5(4), 588–599.
   Google Scholar
• Mizzi, L., Maniscalco, D., Gaspari, S., Chatzitzika, C., Gatt, R., & Valdramidis, V. P. (2020). Assessing the individual microbial inhibitory capacity of different sugars against pathogens commonly found in food systems. Letters in Applied Microbiology, 71(3), 251–258. https://doi.org/10.1111/lam.13306
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Ashraf, J., Hussein, E. M., Nazir, Y., Alwuthaynani, A. S., Naeem, N., Sadiq, A., Alsantali, R. I., & Ahmed, S. A. (2022). Design, synthesis, and structural characterization of thioflavones and thioflavonols as potential tyrosinase inhibitors: In vitro and in silico studies. ACS Omega, 7(20), 17444–17461. https://doi.org/10.1021/acsomega.2c01841
   PubMed Web of Science ®Google Scholar
• Nahrin, A., Junaid, M., Afrose, S. S., Barua, A., Akter, Y., Alam, M. S., Sharmin, T., Ferdousy, S., & Hosen, S. M. Z. (2022). Ziziphus oenoplia Mill.: A systematic review on ethnopharmacology, phytochemistry and pharmacology of an important traditional medicinal plant. Mini Reviews in Medicinal Chemistry, 22(4), 640–660. https://doi.org/10.2174/1389557521666210810153311
   PubMed Web of Science ®Google Scholar
• Nolan, V. C., Harrison, J., & Cox, J. A. (2019). Dissecting the antimicrobial composition of honey. Antibiotics, 8(4), 251. https://doi.org/10.3390/antibiotics8040251
   Google Scholar
• Osmaniye, D., Ahmad, I., Sağlık, B. N., Levent, S., Patel, H. M., Ozkay, Y., & Kaplancıklı, Z. A. (2022). Design, synthesis and molecular docking and ADME studies of novel hydrazone derivatives for AChE inhibitory, BBB permeability and antioxidant effects. Journal of Biomolecular Structure and Dynamics, 3, 1–17. https://doi.org/10.1080/07391102.2022.2139762
   Google Scholar
• Owayss, A. A., Elbanna, K., Iqbal, J., Abulreesh, H. H., Organji, S. R., Raweh, H. S., & Alqarni, A. S. (2020). In vitro antimicrobial activities of Saudi honeys originating from Ziziphus spina‐christi L. and Acacia gerrardii Benth. trees. Food Science & Nutrition, 8(1), 390–401.
   PubMed Web of Science ®Google Scholar
• Pandey, R., Dubey, I., Ahmad, I., Mahapatra, D. K., Patel, H., & Kumar, P. (2022). In silico study of some dexamethasone analogs and derivatives against SARs-CoV-2 target: A cost-effective alternative to remdesivir for various COVID phases. Current Chinese Science, 2(4), 294–309. https://doi.org/10.2174/2210298102666220404102217
   Google Scholar
• Parveen, M., Ghalib, R. M., Khanam, Z., Mehdi, S. H., & Ali, M. (2010). A novel antimicrobial agent from the leaves of Peltophorum vogelianum (Benth.). Natural Product Research, 24(13), 1268–1273. https://doi.org/10.1080/14786410903387688
   PubMed Web of Science ®Google Scholar
• Paul, R. K., Ahmad, I., Patel, H., Kumar, V., & Raza, K. (2023). Phytochemicals from Amberboa ramosa as potential DPP-IV inhibitors for the management of Type-II Diabetes Mellitus: Inferences from in-silico investigations. Journal of Molecular Structure, 1271, 134045. https://doi.org/10.1016/j.molstruc.2022.134045
   Web of Science ®Google Scholar
• Qaid, H. R. A. A. (2021). In-vitro study of Yemen Sidr honey for periodontopathogen bacteria and the benefit effect on cell culture. [Doctoral dissertation]. Universitas Airlangga.
   Google Scholar
• Radwan, H. A., Ahmad, I., Othman, I. M., Gad-Elkareem, M. A., Patel, H., Aouadi, K., Snoussi, M., & Kadri, A. (2022). Design, synthesis, in vitro anticancer and antimicrobial evaluation, SAR analysis, molecular docking and dynamic simulation of new pyrazoles, triazoles and pyridazines based isoxazole. Journal of Molecular Structure, 1264, 133312. https://doi.org/10.1016/j.molstruc.2022.133312
   Web of Science ®Google Scholar
• Sateriale, D., Facchiano, S., Colicchio, R., Pagliuca, C., Varricchio, E., Paolucci, M., Volpe, M. G., Salvatore, P., & Pagliarulo, C. (2020). In vitro synergy of polyphenolic extracts from honey, myrtle and pomegranate against oral pathogens, S. mutans and R. dentocariosa. Frontiers in Microbiology, 11, 1465. https://doi.org/10.3389/fmicb.2020.01465
   PubMed Web of Science ®Google Scholar
• Tople, M. S., Patel, N. B., Patel, P. P., Purohit, A. C., Ahmad, I., & Patel, H. (2023). An in silico-in vitro antimalarial and antimicrobial investigation of newer 7-chloroquinoline based Schiff-bases. Journal of Molecular Structure, 1271, 134016. https://doi.org/10.1016/j.molstruc.2022.134016
   Web of Science ®Google Scholar
• Villoutreix, B. O., Lagorce, D., Labbé, C. M., Sperandio, O., & Miteva, M. A. (2013). One hundred thousand mouse clicks down the road: Selected online resources supporting drug discovery collected over a decade. Drug Discovery Today, 18(21-22), 1081–1089. https://doi.org/10.1016/j.drudis.2013.06.013
   PubMed Web of Science ®Google Scholar
• Zakaria, A. S. (2015). Mechanism of antibacterial action of honey on pathogenic wound bacterial strains: A proteomic analysis. International Research Journal of Pharmacy, 6(11), 778–788. https://doi.org/10.7897/2230-8407.0611151
   Google Scholar