The Compound Specific Antibacterial Activities of Major Urolithins and Their Methyl Ethers

Yıl 2021, Cilt: 8 Sayı: 2, 579 - 584, 31.05.2021

Hayrettin Ozan Gülcan , Mehmet İlktaç , Bahareh Noshadi , Karar Shukur , Mustafa Gazi

https://doi.org/10.18596/jotcsa.861808

Cited By: 4

Öz

The investigation of biological activities of natural products, particularly considering the secondary metabolites, continuously receives attention. Urolithins, the bioavailable metabolites of ellagitannins, were shown to possess enzyme inhibitor, antioxidant, and anti-inflammatory compounds in scientific studies conducted in the last two decades. Regarding the limited number of studies related to their antimicrobial activity, this study aimed to synthesize major urolithins (Urolithin A and B) concomitant to their methyl ether derivatives and screen their antibacterial activity against some Gram-positive and Gram-negative bacteria. In parallel to the antibacterial activity, the synergistic and antagonist properties of the compounds were also analyzed in the presence of reference beta-lactam antibiotics. The results displayed the improvable characteristics of urolithin scaffold to be employed in antibiotic drug design studies. In addition, the antagonist effect of some compounds on the antibacterial action of standard molecules also pointed out the compound-specific activities of the title molecules.

Anahtar Kelimeler

Urolithin, synthesis, antibacterial activity, antagonism, synergism

Kaynakça

• 1. Koehn FE, Carter GT. The evolving role of natural products in drug discovery. Nature reviews Drug discovery. 2005 Mar;4(3):206-20.
• 2. Ji HF, Li XJ, Zhang HY. Natural products and drug discovery: can thousands of years of ancient medical knowledge lead us to new and powerful drug combinations in the fight against cancer and dementia?. EMBO reports. 2009 Mar;10(3):194-200.
• 3. Wöll S, Kim SH, Greten HJ, Efferth T. Animal plant warfare and secondary metabolite evolution. Natural products and bioprospecting. 2013 Feb 1;3(1):1-7.
• 4. Pathan H, Williams J. Basic opioid pharmacology: an update. British journal of pain. 2012 Feb;6(1):11-6.
• 5. Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. The Journal of antibiotics. 2009 Jan;62(1):5-16.
• 6. Gulcan HO, Unlu S, Esiringu İ, Ercetin T, Sahin Y, Oz D, Sahin MF. Design, synthesis and biological evaluation of novel 6H-benzo [c] chromen-6-one, and 7, 8, 9, 10-tetrahydro-benzo [c] chromen-6-one derivatives as potential cholinesterase inhibitors. Bioorganic & medicinal chemistry. 2014 Oct 1;22(19):5141-54.
• 7. Selma MV, Beltrán D, García-Villalba R, Espín JC, Tomás-Barberán FA. Description of urolithin production capacity from ellagic acid of two human intestinal Gordonibacter species. Food & function. 2014;5(8):1779-84.
• 8. Gonzalez-Barrio R, Truchado P, Ito H, Espin JC, Tomas-Barberan FA. UV and MS identification of urolithins and nasutins, the bioavailable metabolites of ellagitannins and ellagic acid in different mammals. Journal of Agricultural and Food Chemistry. 2011 Feb 23;59(4):1152-62.
• 9. Landete JM. Ellagitannins, ellagic acid and their derived metabolites: a review about source, metabolism, functions and health. Food research international. 2011 Jun 1;44(5):1150-60.
• 10. Seeram NP, Henning SM, Zhang Y, Suchard M, Li Z, Heber D. Pomegranate juice ellagitannin metabolites are present in human plasma and some persist in urine for up to 48 hours. The Journal of nutrition. 2006 Oct 1;136(10):2481-5.
• 11. Lipińska L, Klewicka E, Sójka M. The structure, occurrence and biological activity of ellagitannins: a general review. Acta Scientiarum Polonorum Technologia Alimentaria. 2014 Sep 30;13(3):289-99.
• 12. Ammar OM, Ilktac M, Gulcan HO. Urolithins and their antimicrobial activity: A short review. EMU Journal of Pharmaceutical Sciences. 2019;3(2):117-24.
• 13. Giménez-Bastida JA, Truchado P, Larrosa M, Espín JC, Tomás-Barberán FA, Allende A, García-Conesa MT. Urolithins, ellagitannin metabolites produced by colon microbiota, inhibit quorum sensing in Yersinia enterocolitica: phenotypic response and associated molecular changes. Food chemistry. 2012 Jun 1;132(3):1465-74.
• 14. Noshadi B, Ercetin T, Luise C, Yuksel MY, Sippl W, Sahin MF, Gazi M, Gulcan HO. Synthesis, Characterization, Molecular Docking, and Biological Activities of Some Natural and Synthetic Urolithin Analogs. Chemistry & Biodiversity. 2020 Aug;17(8):e2000197.
• 15. The European Committee on Antimicrobial Susceptibility Testing (EUCAST). Breakpoint tables for interpretation of MICs and zone diameters. Version 11.0, 2021. http://www.eucast.org.
• 16. Leber A. Broth Microdilution Test. In: Clinical Microbiology Procedures Handbook, Fourth Edition. ASM Press, Washington, DC. 2016. pp. 5.2.1.1-5.2.2.10. doi: 10.1128/9781555818814.ch5.2.1.
• 17. Leber A. Synergism Testing: Broth Microdilution Checkerboard and Broth Macrodilution Methods. In: Clinical Microbiology Procedures Handbook, Fourth Edition. ASM Press, Washington, DC. 2016. pp. 5.16.1-5.16.23. doi: 10.1128/9781555818814.ch5.16.
• 18. Ishimoto H, Shibata M, Myojin Y, Ito H, Sugimoto Y, Tai A, Hatano T. In vivo anti-inflammatory and antioxidant properties of ellagitannin metabolite urolithin A. Bioorganic & medicinal chemistry letters. 2011 Oct 1;21(19):5901-4.
• 19. Moghaddam KM, Iranshahi M, Yazdi MC, Shahverdi AR. The combination effect of curcumin with different antibiotics against Staphylococcus aureus. International Journal of Green Pharmacy (IJGP). 2009;3(2).
• 20. Hemaiswarya S, Kruthiventi AK, Doble M. Synergism between natural products and antibiotics against infectious diseases. Phytomedicine. 2008 Aug 1;15(8):639-52.