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Antibacterial and Antioxidant Activity of Isoflavans from the Roots of Rhynchosia ferruginea and In Silico Study on DNA Gyrase and Human Peroxiredoxin

Year 2021, Volume: 8 Issue: 4, 321 - 336, 26.12.2021
https://doi.org/10.21448/ijsm.962120

Abstract

Rhynchosia ferruginea (Udusalim, Afan Oromo) is a medicinal plant traditionally used to treat skin infection, intestinal problems and amoebiasis. Silica gel chromatographic separation of dichloromethane/methanol (1:1) roots extract yielded isoflavan (1), isoflavene (2) and 1, 3-dilinoleoyl-2-stearoylglycerol (3), reported herein for the first time from the genus. Antibacterial activity was examined using disc diffusion method against E. coli, S. aureus, P. aeruginosa and S. pyogenes. AutoDoc vina 4.2 soft ware was used for molecular docking analysis of compounds against human peroxidoxin 5 and DNA gyrase B enzymes. Isoflavan (1) displayed zone of inhibition of 9.67 ± 0.58 mm and 10.67 ± 0.58 mm whereas isoflavene (2) showed 10.33 ± 1.15 mm and 10 ± 1.00 mm against E. coli and S. aureus, respectively, compared to ciprofloxacin (15.67±0.58 mm for both strains). DPPH radical scavenging assay of the dichloromethane/methanol (1:1) roots extract and isoflavan (1) exhibited better radical scavenging activity with IC50 value of 17.7 and 32, respectively. Molecular docking analysis revealed that 1 and 2 exhibited similar binding affinity of -7.4 kcal/mol compared to ciprofloxacin (-7.3 kcal/mol). In silico analysis against human peroxidoxin 5 (PDB ID: 1HD2) revealed minimum binding affinity of - 3.7 and - 2.0 kcal/mol for compounds 1 and 2, respectively, compared to ascorbic acid (-4.9 kcal/mol). The in vitro antibacterial and antioxidant activity of compounds 1 and 2 suggest the potential use of these compounds as drug lead candidates which corroborate with the traditional uses of the roots of R. ferruginea.

Thanks

The authors are highly thankful to Adama Science and Technology University (ASTU) for MSc study opportunity given to Mr. Kalid Hussien. Department of Chemistry, Addis Ababa University is duly acknowledged for access to NMR instrument.

References

  • Ansari, Q.A, Ahmed, S.A.,Waheed, M.A., Juned, S.A. (2013). Extraction and Determination of Antioxidant Activity of Withania somnifera Dunal. Pelagia Research Library European Journal of Experimental Biology, 3(5), 502-507.
  • Anza, M., Endale M., Cardona, L., Cortes, D., Eswaramoorthy, R., Cabedo, N., Abarca, B., Zueco, J., Rico, H., Domingo-Ortí, I., Palomino-Schätzlein, M. (2021). Cytotoxicity, antimicrobial activity, molecular docking, drug likeness and DFT analysis of benzo[c]phenanthridine alkaloids from roots of Zanthoxylum chalybeum. Biointerface Research in Applied Chemistry, 12(2),1569-1586.
  • Bekele, B., Adane, L.,Tariku, Y., Hailu, A.(2013). Evaluation of Antileishmanial Activities of Triglycerides Isolated from Roots of Moringa stenopetala. Medicinal Chemistry Research, 22(10), 4592-99.
  • Eswaramoorthy, R., Hailekiros, H., Kedir, F., Endale, M. (2021). In silico Molecular Docking, DFT Analysis andADMET Studies of Carbazole Alkaloid and Coumarins from Roots of Clausena anisata: A PotentInhibitor for Quorum Sensing. Advances and Applications in Bioinformatics and Chemistry, 14, 13-24.
  • Fan, J.I., Kuang, Y., Dong, Z.,Yi, Y., Zhou, B., Li, X., Qiao, X., Ye, M. (2020). Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza Uralensis as PTP1B and α-Glucosidase Inhibitors. Journal of Natural Products, 83(4), 814-824.
  • Galma, W., Endale, M., Getaneh, E., Eswaramoorthy, R., Assefa, T., Melaku, Y. (2021). Antibacterial and antioxidant activities of extracts and isolated compounds from the roots extract of Cucumis prophetarum and in silico study on DNA gyrase and human peroxiredoxin 5. BMC Chemistry, 15(32),1-17.
  • Gundidza, M., Gweru, N., Magwa, M.L., Ramalivhana, N.J., Humphrey, G., Samie, A., Mmbengwa, V. (2009). Phytochemical Composition and Biological Activities of Essential Oil of Rhynchosiaminima (L) (DC) (Fabaceae). African Journal of Biotechnology, 8(5), 721-724.
  • Hangun-Balkir, Y., McKenney, M. (2012). Determination of Antioxidant Activities of Berries and Resveratrol. Green Chemistry Letters and Reviews, 5(2), 147-53.
  • Jima, T., Megersa, M. (2018). Ethnobotanical Study of Medicinal Plants Used to Treat Human Diseases in Berbere District, Bale Zone of Oromia Regional State, South East Ethiopia. Evidence-Based Complementary and Alternative Medicine, 2018, 1-17.
  • Joseph, B., Kumbhare, P., Kale, M. (2013). Preliminary Phytochemical Screening of Selected Medicinal Plants. Inernational Research Journal of Science and Engineering, 29(2), 12-16.
  • Petrovska, B. B. (2012). Historical review of medicinal plants' usage. Pharmacognosy Reviews, 6(11), 1-5.
  • Mansourian, M., Fassihi, A.,Saghaie, L., Madadkar, S., Mahnam, K., Abbasi, M. (2015). QSAR and Docking Analysis of A2B Adenosine Receptor Antagonists Based on Non-Xanthine Scaffold. Medicinal Chemistry Research, 24(1), 394-407.
  • Muhammad, N., Uddin, N., Ali, N. (2019). Ethnomedicinal Uses and Inter Specific Diversity Encourage Conservation of Rhynchosia Species Growing in Hilly Areas of Swat. Agricultural Research & Technology: Open Access Journal, 20(2), 96-107.
  • Proestos, C., Lytoudi, K., Mavromelanidou, O., Zoumpoulakis, P., Sinanoglou, V. (2013). Antioxidant Capacity of Selected Plant Extracts and Their Essential Oils. Antioxidants, 2(6), 11-22.
  • Rungsung, W., Ratha, K., Dutta, S., Dixit, A., Hazra, J. (2015). Secondary Metabolites of Plants In Drugs Discovery. World Journal of Pharmaceutical Research,4(7), 604-13.
  • Tanaka, H., Oh-Uchi, T., Etoh, H., Shimizu, H., Tateishi, Y. (2002). Isoflavonoids from the Roots of Erythrina poeppigiana. Phytochemistry, 60(8), 789-94.

Antibacterial and Antioxidant Activity of Isoflavans from the Roots of Rhynchosia ferruginea and In Silico Study on DNA Gyrase and Human Peroxiredoxin

Year 2021, Volume: 8 Issue: 4, 321 - 336, 26.12.2021
https://doi.org/10.21448/ijsm.962120

Abstract

Rhynchosia ferruginea (Udusalim, Afan Oromo) is a medicinal plant traditionally used to treat skin infection, intestinal problems and amoebiasis. Silica gel chromatographic separation of dichloromethane/methanol (1:1) roots extract yielded isoflavan (1), isoflavene (2) and 1, 3-dilinoleoyl-2-stearoylglycerol (3), reported herein for the first time from the genus. Antibacterial activity was examined using disc diffusion method against E. coli, S. aureus, P. aeruginosa and S. pyogenes. AutoDoc vina 4.2 soft ware was used for molecular docking analysis of compounds against human peroxidoxin 5 and DNA gyrase B enzymes. Isoflavan (1) displayed zone of inhibition of 9.67 ± 0.58 mm and 10.67 ± 0.58 mm whereas isoflavene (2) showed 10.33 ± 1.15 mm and 10 ± 1.00 mm against E. coli and S. aureus, respectively, compared to ciprofloxacin (15.67±0.58 mm for both strains). DPPH radical scavenging assay of the dichloromethane/methanol (1:1) roots extract and isoflavan (1) exhibited better radical scavenging activity with IC50 value of 17.7 and 32, respectively. Molecular docking analysis revealed that 1 and 2 exhibited similar binding affinity of -7.4 kcal/mol compared to ciprofloxacin (-7.3 kcal/mol). In silico analysis against human peroxidoxin 5 (PDB ID: 1HD2) revealed minimum binding affinity of - 3.7 and - 2.0 kcal/mol for compounds 1 and 2, respectively, compared to ascorbic acid (-4.9 kcal/mol). The in vitro antibacterial and antioxidant activity of compounds 1 and 2 suggest the potential use of these compounds as drug lead candidates which corroborate with the traditional uses of the roots of R. ferruginea.

References

  • Ansari, Q.A, Ahmed, S.A.,Waheed, M.A., Juned, S.A. (2013). Extraction and Determination of Antioxidant Activity of Withania somnifera Dunal. Pelagia Research Library European Journal of Experimental Biology, 3(5), 502-507.
  • Anza, M., Endale M., Cardona, L., Cortes, D., Eswaramoorthy, R., Cabedo, N., Abarca, B., Zueco, J., Rico, H., Domingo-Ortí, I., Palomino-Schätzlein, M. (2021). Cytotoxicity, antimicrobial activity, molecular docking, drug likeness and DFT analysis of benzo[c]phenanthridine alkaloids from roots of Zanthoxylum chalybeum. Biointerface Research in Applied Chemistry, 12(2),1569-1586.
  • Bekele, B., Adane, L.,Tariku, Y., Hailu, A.(2013). Evaluation of Antileishmanial Activities of Triglycerides Isolated from Roots of Moringa stenopetala. Medicinal Chemistry Research, 22(10), 4592-99.
  • Eswaramoorthy, R., Hailekiros, H., Kedir, F., Endale, M. (2021). In silico Molecular Docking, DFT Analysis andADMET Studies of Carbazole Alkaloid and Coumarins from Roots of Clausena anisata: A PotentInhibitor for Quorum Sensing. Advances and Applications in Bioinformatics and Chemistry, 14, 13-24.
  • Fan, J.I., Kuang, Y., Dong, Z.,Yi, Y., Zhou, B., Li, X., Qiao, X., Ye, M. (2020). Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza Uralensis as PTP1B and α-Glucosidase Inhibitors. Journal of Natural Products, 83(4), 814-824.
  • Galma, W., Endale, M., Getaneh, E., Eswaramoorthy, R., Assefa, T., Melaku, Y. (2021). Antibacterial and antioxidant activities of extracts and isolated compounds from the roots extract of Cucumis prophetarum and in silico study on DNA gyrase and human peroxiredoxin 5. BMC Chemistry, 15(32),1-17.
  • Gundidza, M., Gweru, N., Magwa, M.L., Ramalivhana, N.J., Humphrey, G., Samie, A., Mmbengwa, V. (2009). Phytochemical Composition and Biological Activities of Essential Oil of Rhynchosiaminima (L) (DC) (Fabaceae). African Journal of Biotechnology, 8(5), 721-724.
  • Hangun-Balkir, Y., McKenney, M. (2012). Determination of Antioxidant Activities of Berries and Resveratrol. Green Chemistry Letters and Reviews, 5(2), 147-53.
  • Jima, T., Megersa, M. (2018). Ethnobotanical Study of Medicinal Plants Used to Treat Human Diseases in Berbere District, Bale Zone of Oromia Regional State, South East Ethiopia. Evidence-Based Complementary and Alternative Medicine, 2018, 1-17.
  • Joseph, B., Kumbhare, P., Kale, M. (2013). Preliminary Phytochemical Screening of Selected Medicinal Plants. Inernational Research Journal of Science and Engineering, 29(2), 12-16.
  • Petrovska, B. B. (2012). Historical review of medicinal plants' usage. Pharmacognosy Reviews, 6(11), 1-5.
  • Mansourian, M., Fassihi, A.,Saghaie, L., Madadkar, S., Mahnam, K., Abbasi, M. (2015). QSAR and Docking Analysis of A2B Adenosine Receptor Antagonists Based on Non-Xanthine Scaffold. Medicinal Chemistry Research, 24(1), 394-407.
  • Muhammad, N., Uddin, N., Ali, N. (2019). Ethnomedicinal Uses and Inter Specific Diversity Encourage Conservation of Rhynchosia Species Growing in Hilly Areas of Swat. Agricultural Research & Technology: Open Access Journal, 20(2), 96-107.
  • Proestos, C., Lytoudi, K., Mavromelanidou, O., Zoumpoulakis, P., Sinanoglou, V. (2013). Antioxidant Capacity of Selected Plant Extracts and Their Essential Oils. Antioxidants, 2(6), 11-22.
  • Rungsung, W., Ratha, K., Dutta, S., Dixit, A., Hazra, J. (2015). Secondary Metabolites of Plants In Drugs Discovery. World Journal of Pharmaceutical Research,4(7), 604-13.
  • Tanaka, H., Oh-Uchi, T., Etoh, H., Shimizu, H., Tateishi, Y. (2002). Isoflavonoids from the Roots of Erythrina poeppigiana. Phytochemistry, 60(8), 789-94.
There are 16 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Articles
Authors

Kalid Hussein This is me 0000-0002-6742-7880

Rajalakshmanan Eswaramoorthy 0000-0002-8331-2100

Yadessa Melaku This is me 0000-0003-2599-0517

Milkyas Endale Annisa 0000-0002-5301-9923

Publication Date December 26, 2021
Submission Date July 3, 2021
Published in Issue Year 2021 Volume: 8 Issue: 4

Cite

APA Hussein, K., Eswaramoorthy, R., Melaku, Y., Endale Annisa, M. (2021). Antibacterial and Antioxidant Activity of Isoflavans from the Roots of Rhynchosia ferruginea and In Silico Study on DNA Gyrase and Human Peroxiredoxin. International Journal of Secondary Metabolite, 8(4), 321-336. https://doi.org/10.21448/ijsm.962120
International Journal of Secondary Metabolite

e-ISSN: 2148-6905