DOI QR코드

DOI QR Code

A New Stilbene Dimer and Other Chemical Constituents from Monanthotaxis littoralis with Their Antimicrobial Activities

  • Dongmo, Arnaud Joseph Nguetse (Research Unit of Applied and Environmental Chemistry, Department of Chemistry, Faculty of Science, University of Dschang) ;
  • Ekom, Steve Endeguele (Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang) ;
  • Tamokou, Jean-de-Dieu (Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang) ;
  • Tagousop, Cyrille Ngoufack (Department of Basic Scientific Studies, University Institute of Technology, University of Ngaoundere) ;
  • Harakat, Dominique (Service Commun d'Analyses, Institut de Chimie Moleculaire de Reims (ICMR)) ;
  • Voutquenne-Nazabadioko, Laurence (Groupe Isolement et Structure, Institut de Chimie Moleculaire de Reims (ICMR)) ;
  • Ngnokam, David (Research Unit of Applied and Environmental Chemistry, Department of Chemistry, Faculty of Science, University of Dschang)
  • Received : 2020.10.24
  • Accepted : 2020.12.02
  • Published : 2020.12.31

Abstract

A new dimer stilbene [Monalittorin (1)] and ten known compounds [engeletin (2), aurantiamide acetate (3), lupeol (4), friedelin (5), quercetin (6), tiliroside (7), rutoside (8), astragalin (9), isoquercitrin (10) and quercimeritroside (11)] have been isolated from the leaves of Monanthotaxis littoralis (Annonaceae). The structures of these compounds were established by interpretation of their data, mainly, HR-TOFESIMS, 1-D NMR (1H and 13C) and 2-D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and by comparison with the literature. The evaluation of their antimicrobial activities against three bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli S2 (1) and Pseudomonas aeruginosa PA01) and three fungal strains (Candida albicans ATCC10231, Candida tropicalis PK233 and Cryptococcus neoformans H99) using broth micro dilution method, showed the largest antimicrobial activities of EtOAc fraction and compounds 1, 5, 6, 8 and 11 (MIC = 8 - 64 ㎍/mL). In addition, EtOAc fraction presented synergistic effect with Vancomycin and fluconazole against the tested microorganisms.

Keywords

References

  1. Clara, C.; Matasyoh, J. C.; Wagara, I. N.; Nakavuma, J. Am. J. Chem. Appl. 2014, 1, 54-60.
  2. Bele, M. Y.; Focho, D. A.; Egbe, E. A.; Chuyong, B. G. Afr. J. Plant Sci. 2011, 5, 237-247.
  3. Clara, C.; Matasyoh, J. C.; Wagara, I. N.; Nakavuma, J. Int. J. Microbiol. Res. Rev. 2013, 2, 103-109.
  4. Joubouhi, C.; Tamokou, J. d. D.; Ngnokam, D.; Voutquenne-Nazabadioko, L.; Kuiate, J. R. BMC Complem. Altern. Med. 2017, 17, 1- 8. https://doi.org/10.1186/s12906-016-1536-8
  5. Tagousop, N. C.; Tamokou, J. d. D.; Kengne, I. C.; Ngnokam, D.; Voutquenne-Nazabadioko, L. Chem. Cent. J. 2018, 12, 97. https://doi.org/10.1186/s13065-018-0466-6
  6. Kenfack, J. N.; Ngoudjou, D. T.; Ponou, B. K.; Kühlborn, J.; Tsafack, B. T.; Teponno, R. B.; Opatz, T.; Barboni, L.; Gatsing, D.; Tapondjou, L. A. Sci. J. Chem. 2020, 8, 48-58. https://doi.org/10.11648/j.sjc.20200803.12
  7. CLSI. M27 Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. 4th ed; Clinical and Laboratory Standards Institute; USA, 2017, pp 1-46.
  8. CLSI. M07-A8 Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. 8th ed; Clinical and Laboratory Standards Institute; USA, 2010, pp 1-65.
  9. Bone, R. C. Arch. Intern. Med. 1994, 154, 26-34. https://doi.org/10.1001/archinte.1994.00420010044006
  10. Pel, P.; Chae, H. S.; Nhoek, P.; Kim, Y. M.; Khiev, P.; Kim, G. J.; Nam, J. W.; Choi, H.; Choi, Y. H.; Chin, Y. W. Bioorg. Chem. 2020, 99, 103869. https://doi.org/10.1016/j.bioorg.2020.103869
  11. Niesen, D. B.; Craig, H.; Seeram, N. P. J. Berry Res. 2013, 3, 181-196. https://doi.org/10.3233/JBR-130062
  12. Garg, H. S.; Chaturvedi, R.; Bhakuni, D. S. J. Nat. Prod. 1991, 54, 104-109. https://doi.org/10.1021/np50073a007
  13. Li, J.; Tan, L. H.; Zou, H.; Zou, Z. X.; Long, H. P.; Wang, W. X.; Xu, P. S.; Liu, L. F.; Xu, K. P.; Tan, G. S. J. Nat. Prod. 2020, 83, 216-222. https://doi.org/10.1021/acs.jnatprod.9b00470
  14. Liu, Y.; Zhang, X.; Kelsang, N.; Tu, G.; Kong, D.; Lu, J.; Zhang, Y.; Liang, H.; Tu, P.; Zhang, Q. J. Nat. Prod. 2018, 81, 307-315. https://doi.org/10.1021/acs.jnatprod.7b00736
  15. Zhang, X.; Chen, C.; Li, Y.; Chen, D.; Dong, L.; Na, W.; Wu, C.; Zhang, J.; Li, Y. J. Nat. Prod. 2016, 79, 1249-1258. https://doi.org/10.1021/acs.jnatprod.5b00820
  16. Ma, G. L.; Xiong, J.; Yang, G. X.; Pan, L. L.; Hu, C. L.; Wang, W.; Fan, H.; Zhao, Q. H.; Zhang, H. Y.; Hu, J. F. J. Nat. Prod. 2016, 79, 1354-1364. https://doi.org/10.1021/acs.jnatprod.6b00061
  17. Sagawa, T.; Takaishi, Y.; Fujimoto, Y.; Duque, C.; Osorio, C.; Ramos, F.; Garzon, C.; Sato, M.; Okamoto, M.; Oshikawa, T.; Ahmed, S. U. J. Nat. Prod. 2005, 68, 502-505. https://doi.org/10.1021/np040187y
  18. Ali, A. H.; Hassan, N. M.; Shukor, N. I.; Embi, N.; Latip, J.; Mohd Sidek, H. M. Malays. Appl. Biol. 2014, 43, 73-80.
  19. Zhou, B.; Yang, Z.; Feng, Q.; Liang, X.; Li, J.; Zanin, M.; Jiang, Z.; Zhong, N. J. Ethnopharmacol. 2017, 199, 60-67. https://doi.org/10.1016/j.jep.2017.01.038
  20. Kaundal, M.; Akhtar, M.; Deshmukh, R. J. Neurol. Neurosci. 2017, 8, 1-8. https://doi.org/10.21767/2171-6625.1000195
  21. Mann, A.; Ibrahim, K.; Oyewale, A. O.; Amupitan, J. O.; Fatope, M. O.; Okogum, J. I. Am. J. Chem. 2011, 1, 52-55. https://doi.org/10.5923/j.chemistry.20110102.11
  22. Sinha, R.; Gadhwal, M. K.; Joshi, U. J.; Srivastava, S.; Govil, G. Int. J. Curr. Pharm. Res. 2012, 4, 70-79.
  23. Larit, F.; Benyahia, S.; Benayache, S.; Benayache, F.; Léon, F.; Brouard, I.; Bermijo, J. Int. J. Med. Arom. Plants 2012, 2, 34-37.
  24. Dehaghani, Z. A.; Asghari, G.; Dinani, M. S. J. Agric. Sci. Tech. A 2017, 7, 45-51.
  25. Ghavan-Haghi, F.; Dinani, M. S. J. Herbmed Pharmacol. 2017, 6, 114-118.
  26. Li, H.; Liu, Y.; Yi, Y.; Miao, Q.; Lui, S.; Zhao, F.; Cong, W.; Wang, C.; Xia, C. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2017, 1048, 56-63. https://doi.org/10.1016/j.jchromb.2017.01.041
  27. Legault, J.; Perron, T.; Mshvildadze, V.; Girard-Lalancette, K.; Perron, S.; Laprise, C.; Sirois, P.; Pichette, A. J. Med. Food 2011, 14, 1127-1134. https://doi.org/10.1089/jmf.2010.0198
  28. Tamokou, J.-d.-D.; Mbaveng, T. A.; Kuete, V. In Medicinal Spices and Vegetables from Africa 1st Ed: Therapeutic Potential against Metabolic, Inflammatory, Infectious and Systemic Diseases; Academic Press; Amsterdam, 2017, pp 207-237.
  29. Kengne, I. C.; Tamokou, J. D. D. Invest. Med. Chem. Pharmacol. 2018, 1, 9.