Isolation of Flavonoid (Z)-2-(3-Acetyl-4-Hydroxy Benzylidine)-6-Hydroxy-4-Methoxybenzofuran-3(2h)-One of Rheum Rhabarbarum and Evaluation of Antimicrobial Activity against a Panel of Human Pathogens

Hala I ElzubirDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi ArabiaAbdel Karim MSudan University of Science and Technology, Faculty of Science, SudanAsra Banu SyedaDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi ArabiaLeena S IbrahimDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi ArabiaFatima A KhleefDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi ArabiaHiam M. OsmanDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi Arabia

Vol 10 No 4 (2026): Volume 10, Issue 4, April 2026 | Pages: 347-354

International Research Journal of Innovations in Engineering and Technology

OPEN ACCESS | Research Article | Published Date: 30-04-2026

doi Logo doi.org/10.47001/IRJIET/2026.104049

Abstract

Rheum rhabarbarum, often referred to as rhubarb, has been utilized as a healing herb in various nations.  Particularly, its stems are recognized as a traditional remedy in various cultures. Rhubarbs contain numerous bioactive substances, belonging to diverse groups of phytochemicals, e.g. stilbenes, anthraquinones and flavonoids. In this study Phytochemical screening of Rheum rhabarbarum stems revealed the presence of flavonoids, alkaloids, sterols, saponins and glycosides. Stems Rheum rhabarbarum were macerated with 95% ethanol to prepare for isolation. The method used for isolation was a combination column chromatography (CC) followed by thin layer chromatography (TLC), which gave flavonoid (z)-2-(3-acetyl-4-hydroxy benzylidine)-6-hydroxy-4-methoxybenzofuran-3(2H)-one. And the structures of the isolate were elucidated via a combination of spectral techniques. Also study the antimicrobial activity of ethanol extract of R. rhabarbarum stems against bacterial and fungal strain. And the results showed that the ethanolic extract was very active against Staphylococcus aureus, Bacillus subtilis, and the fungus Candida albicans, and active against Pseudomonas aeruginosa, and inactive against Escherichia coli.

Keywords

Rheum rhabarbarum, medicinal herb, Flavonoid, Antimicrobial, TLC


Citation of this Article

Hala I Elzubir, Abdel Karim M, Asra Banu Syeda, Leena S Ibrahim, Fatima A Khleef, & Hiam M. Osman. (2026). Isolation of Flavonoid (Z)-2-(3-Acetyl-4-Hydroxy Benzylidine)-6-Hydroxy-4-Methoxybenzofuran-3(2h)-One of Rheum Rhabarbarum and Evaluation of Antimicrobial Activity against a Panel of Human Pathogens. International Research Journal of Innovations in Engineering and Technology - IRJIET, 10(4), 347-354. Article DOI https://doi.org/10.47001/IRJIET/2026.104049

References
  1. Rumpunen, K.; Henriksen, K. Phytochemical and morphological characterization of seventy-one cultivars and selections of culinary rhubarb (Rheum spp.). J. Hortic. Sci. Biotechnol., 1999, 74(1), 13-18. https://doi.org/10.1080/14620316.1999.11511064.
  2. Foust, C. M.; Marshall, D. E. Culinary rhubarb production in North America: history and recent statistics. HortScience, 1991, 26(11), 1360-1363.
  3. Nadulski, R.; Skwarcz, J.; Sujak, A.; Kobus, Z.; Zawiślak, K.; Stój, A.; Wyrostek, J. Effect of pre-treatment on pressing efficiency and properties of rhubarb (Rheum rhaponticum L.) juice. J. Food Eng., 2015,166, 370-376. http://dx.doi.org/10.1016/j.jfoodeng.2015.06.035.
  4. Huang, Z.; Xu, Y.; Wang, Q.; Gao, X. Metabolism and mutual biotransformations of anthraquinones and anthrones in rhubarb by human intestinal flora using UPLC-Q-TOF/MS. J. Chromatogr. B., 2019, 1104, 59-66.
  5. Jintao, X.; Yongli, S.; Liming, Y.; Quanwei, Y.; Chunyan, L.; Xingyi, C.; Yun, J. Near-infrared spectroscopy for rapid and simultaneous determination of five main active components in rhubarb of different geographical origins and processing. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2018, 205, 419-427.
  6. Baytop T; Rheum ribes L, In T. Baytop (Ed), Therapy with medicinal plants in Turkey, Noble Tip Pub., 1999, 1, 319-320.
  7. Xing, X. Y.;Zhao, Y. L.; Kong, W. J.; Wang, J. B.; Jia, L.; Zhang, P.; Yan, D.; Zhang. Y.; Li, R.; Xiao, X. H. Investigation of the “dose–time–response” relationships of rhubarb on carbon tetrachloride-induced liver injury in rats. J. Ethnopharmacol., 2011, 135(2), 575-581. doi:10.1016/j.jep.2011.03.053.
  8. Xu, Z. P.; Lu, Z. J.; Chen, J. H.; Deng, X. Y.; Mao, Y. Z.; Huo, X. The effect of rhubarb ethanol-extract on hyperlipidemia and liver fatty in rabbits. Zhongguo Ying Yong Sheng li xue za zhi= Zhongguo Yingyong Shenglixue Zazhi= Chinese.  J. Appl. Physiol., 2007, 23(3), 375-380.
  9. Caballero, B. Guide to nutritional supplements. 2009, Academic Press.
  10. Lugasi, A. The role of antioxidant phytonutrients in the prevention of diseases. Acta Biol. Szeged., 2003, 47(1-4), 119-125.
  11. Hertog, M. G.; Feskens, E. J.; Kromhout, D.; Hollman, P. C. H.; Katan, M. B. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet, 1993, 342(8878), 1007-1011.DOI: 10.1016/0140-6736(93)92876-u.
  12. Knekt, P.; Järvinen, R.; Seppänen, R.; Heliövaara, M.; Teppo, L.; Pukkala, E.; Aromaa, A. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. Am. J. Epidemiol., 1997, 146(3), 223-230. doi.org/10.1093/oxfordjournals.aje.a009257.
  13. Kyle, J. A.;Sharp, L.; Little, J.; Duthie, G. G.; McNeill, G. Dietary flavonoid intake and colorectal cancer: a case–control study. Br. J. Nutr., 2010, 103(3), 429-436. https://doi.org/10.1017/S0007114509991784.
  14. Gupta, T.; Kataria, R.; Sardana, S. A comprehensive review on current perspectives of flavonoids as antimicrobial agent. Curr. Top. Med. Chem., y, 2022, 22(6), 425-434. https://doi.org/10.2174/1568026622666220117104709.
  15. Biharee, A.; Sharma, A.; Kumar, A.; Jaitak, V. Antimicrobial flavonoids as a potential substitute for overcoming antimicrobial resistance. Fitoterapia., 2020,146, 104720. https://doi.org/10.1016/j.fitote.2020.104720.
  16. Taher, R. F., Al-Karmalawy, A. A., Abd El Maksoud, A. I., Khalil, H., Hassan, A., El-Khrisy, E. D. A., & El-Kashak, W. Two new flavonoids and anticancer activity of Hymenosporum flavum: in vitro and molecular docking studies. J. Herbmed Pharmacol., 2021, 10(4), 443-458. https://doi.org/10.34172/jhp.2021.52.
  17. Ilmiah, H. H.; Sulistyaningsih, E.; Joko, T. Fruit morphology, antioxidant activity, total phenolic and flavonoid contents of Salacca zalacca (Gaertner) Voss by applications of goat manures and Bacillus velezensis B-27. J. Sustain. Agric., 2021, 36(2), 270-282, http://dx.doi.org/10.20961/carakatani.v36i2.43798.
  18. Ekoro, I. A.; Edema, M. O.; Ogwuche, C. E. Isolation of Flavonoids, Antioxidant and Antimicrobial Activities of Costus after Ker Gawl. Stem Extracts. World News Nat. Sciences., 2024, 53, 1-16. www.worldnewsnaturalsciences.com
  19. Fazeli-Nasab, B., Ghafari, M., Jahantigh, M., Beigomi, Z., & Saeidi, S. Evaluation of phenolic and flavonoid content, alkaloids, antioxidant capacity and antibacterial properties of methanolic extract of Zahak native medicinal plants against seven pathogens. J. Med. Plants By-Prod., 2023, 13, 57-65. https://doi.org/10.22034/jmpb.2023.128540.
  20. Tehranian, M. J.; Jouki, M.; Shakouri, M. J.; Jafari, S. Functional properties of Ganoderma lucidum extract: Antimicrobial and antioxidant activities. Food Sci. Technol. 2023, 43. https://orcid.org/0000-0003-4114-3633.
  21. Dalastra, V.; Southier, N.; Anaissi, F. J.; Dalastra, J.; Yamazaky, R. K. Flavonoides presentes nos extratos da campomanesia xanthocarpa Berg/Flavonoids present in extracts of campomanesia xanthocarpa Berg. Braz. J. Dev., 2019, 5(7), 8983-8991. DOI:10.34117/bjdv5.
  22. Mohotti, S.; Rajendran, S.; Muhammad, T.; Strömstedt, A. A.; Adhikari, A.;, Burman, R.;  Gunasekera, S. Screening for bioactive secondary metabolites in Sri Lankan medicinal plants by microfractionation and targeted isolation of antimicrobial flavonoids from Derris scandens. J. Ethnopharmacol., 2020, 246,112158. http://dx.dol.org/10.1016/1.1ep.2019.112158PMID31421182.
  23. Prakash, S.; Elavarasan, N.; Subashini, K.; Kanaga, S.; Dhandapani, R.; Sivanandam, M.; Sujatha, V. Isolation of hesperetin-A flavonoid from Cordia sebestena flower extract through antioxidant assay guided method and its antibacterial, anticancer effect on cervical cancer via in vitro and in silico molecular docking studies. J. Mol. Struct., 2020, 1207, 127751. http://dx.doi.org/10.1016/j.molstruc.2020.127751.
  24. Omosa, L. K.; Amugune, B.; Ndunda, B.; Milugo, T. K.; Heydenreich, M.; Yenesew, A.; Midiwo, J. O. Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia. S. Afr. J. Bot., 2014, 91, 58-62.
  25. Cruz, B. G.; Dos Santos, H. S.; Bandeira, P. N.; Rodrigues, T. H. S.; Matos, M. G. C.; Nascimento, M. F.; Coutinho, H. D. Evaluation of antibacterial and enhancement of antibiotic action by the flavonoid kaempferol 7-O-β-D-(6 ″-O-cumaroyl)-glucopyranoside isolated from Croton piauhiensis müll. Microb. Pathog., 2020, 143, 104144.
  26. Cruz, B. G.; Dos Santos, H. S.; Bandeira, P. N.; Rodrigues, T. H. S.; Matos, M. G. C.; Nascimento, M. F.; Coutinho, H. D. Evaluation of antibacterial and enhancement of antibiotic action by the flavonoid kaempferol 7-O-β-D-(6 ″-O-cumaroyl)-glucopyranoside isolated from Croton piauhiensis müll. Microb. Pathog., 2020, 143, 104144. http://dx.doi.org/10.1016/j.micpath.2020.104144PMID:32194182.
  27. Oresanya, I. O.; Sonibare, M. A.; Gueye, B.; Balogun, F. O.; Adebayo, S.; Ashafa, A. O. T.; Morlock, G. Isolation of flavonoids from Musa acuminata Colla (Simili radjah, ABB) and the in vitro inhibitory effects of its leaf and fruit fractions on free radicals, acetylcholinesterase, 15‐lipoxygenase, and carbohydrate hydrolyzing enzymes. J. Food Biochem., 2020, 44(3), e13137. https://doi.org/10.1111/jfbc.13137.
  28. Singh, B.; Singh, J. P.; Kaur, A.; Singh, N. Bioactive compounds in banana and their associated health benefits–A review. Food Chem., 2016, 206, 1-11. https://doi.org/10.1016/j.foodchem.2016.03.033.
  29. Pekamwar, S. S.; Kalyankar, T. M.; Kokate, S. S. Pharmacological activities of Coccinia grandis. J Appl Pharm Sci, 2013, 3(05), 114-119. DOI: 10.7324/JAPS.2013.3522.
  30. Attasih, M.; Pambudi, D. B.; Saad, M. Determination of total phenolic, flavonoid contents, and antioxidant activity evaluation of ethanolic extract from Plumeria alba. JNHM, 2024, 14-27. https://doi.org/10.23917/jnhm.v5i1.3700.
  31. de Rijke, E.; Out, P.; Niessen, W. M.; Ariese, F.; Gooijer, C.; Brinkman, U. A. T. Analytical separation and detection methods for flavonoids. J. Chromatogr. A., 2006, 1112(1-2), 31-63. doi:10.1016/j.chroma.2006.01.019.
  32. Santos-Buelga, C.; García-Viguera, C.; Tomás-Barberán, F. A. On-line identification of flavonoids by HPLC coupled to diode array detection.  Methods Polyphenol Anal., 2003, 92, 127.
  33. Kolodziejczyk-Czepas, J.; Liudvytska, O. Rheum rhaponticum and Rheum rhabarbarum: A review of phytochemistry, biological activities and therapeutic potential. Phytochem. Rev., 2021, 20(3), 589-607. https://doi.org/10.1007/s11101-020-09715-3.