Synthesis, Characterization, and Antibacterial Activity Study of Novel Curcuminoids Derivatives

Authors

  • Mustafa M. AL-Hakiem Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah, Iraq
  • Mustafa Q. Alderawy Department of Pharmacognosy and Medicinal Plant, College of Pharmacy, University of Basrah, Basrah, Iraq.
  • Riham Adnan Department of Pharmacognosy and Medicinal Plant, College of Pharmacy, University of Basrah, Basrah, Iraq.
  • Rita S Elias Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah, Iraq

DOI:

https://doi.org/10.31351/vol33iss1pp154-162

Keywords:

curcumin, Pyrazole, Chemical synthesis, Antibacterial activity, Curcuminoids

Abstract

Curcumin is a well-known compound with broad spectrum biological activities, but unfortunately rapid degradation properties and low bioavailability. Therefore, several attempts have been made to overcome these obstructions through chemical modifications. This investigation aimed to prepare several curcuminoids and their pyrazole derivatives and study their antibacterial activity. Curcuminoids and their pyrazole derivatives were synthesized, and their Chemical structures were established from their mass, 1H NMR, and 13C NMR spectra, followed by an in vitro study of the antibacterial activity of these compounds against the gram-negative Escherichia coli and the gram-positive Staphylococcus aureus using disc diffusion method. No compound has recorded any activity against Escherichia coli, while compounds 1-9 have shown anti-staphylococcus activity, compounds 11-14 didn’t present any activity, and compound 10 shows activity at the lowest studied concentration only. These findings suggest that the pyrazole substitution on curcumin derivatives that do not bear an aromatic hydroxyl group would diminish their anti-staphylococcal activity. More antibacterial activity studies are suggested regarding compound 10 activity

Received: 28/1 /2023

Accepted: 27/4 /2023

References

Prasad S, Aggarwal BB, Herbal Medicine: Biomolecular and Clinical Aspects. 2nd edition, CRC Press/Taylor & Francis, Boca Raton (FL), 2011, Chapter 13. Available from: https://www.ncbi.nlm.nih.gov/books/NBK92752/

Lee W H, Loo C Y, Bebawy M, Luk F, Mason R S, & Rohanizadeh R . Curcumin and its derivatives: their application in neuropharmacology and neuroscience in the 21st century. Curr. Neuropharmacol. 2013; 11(4): 338-378. https://doi.org/10.2174/1570159X11311040002

Memarzia A, Khazdair M R, Behrouz S, Gholamnezhad Z, Jafarnezhad M, Saadat S, & Boskabady M H. Experimental and clinical reports on anti-inflammatory, antioxidant, and immunomodulatory effects of Curcuma longa and curcumin, an updated and comprehensive review. BioFactors. 2021; 47: 311-350. https://doi.org/10.1002/biof.1716

Wang Z, Mu W, Li P, Liu G, & Yang J. Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo. Eur. J. Pharm. Sci. 2021; 160: 105756. https://doi.org/10.1016/j.ejps.2021.105756.

Foti M C, Slavova-Kazakova A, Rocco C, & Kancheva V D. Kinetics of curcumin oxidation by 2, 2-diphenyl-1-picrylhydrazyl (DPPH): An interesting case of separated coupled proton–electron transfer. Org. Biomol. Chem. 2016; 14(35): 8331-8337. https://doi.org/10.1039/C6OB01439A

Arslan A K, Uzunhisarcıklı E, Yerer M B, & Bishayee A. The golden spice curcumin in cancer: A perspective on finalized clinical trials during the last 10 years. J Cancer Res Ther. 2022; 18(1): 19.‏ https://doi.org/10.4103/jcrt.JCRT_1017_20

Nasery M, Varzandeh M, Pahlavanneshan S, Mohamadi N, Sarhadi S, Fekri H S, Mohammadinejad R, & Ahn K S. Curcumin: A potential therapeutic natural product for adenocarcinomas. Phytochem. Lett. 2022; 49: 45-55,74-3900. https://doi.org/10.1016/j.phytol.2022.02.013.

Zoi V, Galani V, Lianos GD, Voulgaris S, Kyritsis AP, Alexiou G A. The Role of Curcumin in Cancer Treatment. Biomedicines 2021; 9: 1086. https://doi.org/10.3390/biomedicines9091086

Chakraborti S, Dhar G, Dwivedi V, Das A, Poddar A, Chakraborti G, Gautam Basu G, Chakrabarti P, Surolia A, & Bhattacharyya B. Stable and potent analogues derived from the modification of the dicarbonyl moiety of curcumin. Biochemistry 2013;52(42): 7449-7460. https://doi.org/10.1021/bi400734e

Mohammadi E, Amini S M, Mostafavi S H, Amini S M. An overview of antimicrobial efficacy of curcumin-silver nanoparticles. J. Nanomed. Res. 2021; 6: 105-11. https://doi.org/10.22034/nmrj.2021.02.002

Wang Y J, Pan M H, Cheng A L, Lin L I, Ho Y S, Hsieh C Y, & Lin J K. Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal. 1997; 15(12): 1867-1876. https:// doi.org/ 10.1016 / s0731-7085(96)02024-9.

Omidfar K, Khorsand F, & Azizi M D. New analytical applications of gold nanoparticles as label in antibody-based sensors. Biosens Bioelectron. 2013; 43: 336-347. https://doi.org/10.1016/j.bios.2012.12.045

Kaur P, Arora V, & Kharb R. Pyrazole as an anti-inflammatory scaffold: A comprehensive review. Int. J. Health Sci. 2021; 6: 8281–8289. https://doi.org/10.53730/ijhs.v6nS2.7106

Lei Y J, Bi Y, & Jie O Y. Synthesis of some curcumin analogues under ultrasound irradiation. Adv Mat Res . 2011; 332: 1623-1626. https://doi.org/10.4028/www.scientific.net/AMR.332-334.1623

Neamah F O, Saeed B A, & Elias R S. Ultrasonic Waves Assisted Synthesis of Curcuminoids Based on 3-Methylacetylacetone and in Situ Synthesis of Gold Nanoparticles Capped with Curcuminoids. JAC. 2008; 4(3): 494–501. https://doi.org/10.24297/jac.v4i3.946

Amolins M W, Peterson L B, & Blagg B S. Synthesis and evaluation of electron-rich curcumin analogues. Bioorg. Med. Chem. 2009;17(1): 360-367. https://doi.org/10.1016/j.bmc.2008.10.057

Jebur J H, Hassan Q M, Al-Mudhaffer M F, Al-Asadi A S, Elias R S, Saeed B A, & Emshary C A. The gamma radiation effect on the surface morphology and optical properties of alpha-methyl curcumin: PMMA film. Physica Scripta. 2020; 95(4): 045804.‏ https://doi.org/ 10.1088/1402-4896/ab5ca0

Hamed O A, Mehdawi N, Taha A A, Hamed E M, Al-Nuri M A, & Hussein A S. Synthesis and antibacterial activity of novel curcumin derivatives containing heterocyclic moiety. Iran J Pharm Res. 2013;12(1): 47, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813224

Bauer A W. Antibiotic susceptibility testing by a standardized single disc method. Am J clin pathol. 1966; 45:149-158. https://pubmed.ncbi.nlm.nih.gov/5325707/

Seleshe S, & Kang S N. In vitro antimicrobial activity of different solvent extracts from Moringa stenopetala leaves. Prev. Nutr. Food Sci. 2019;24(1): 70. https://doi.org/10.3746/pnf.2019.24.1.70

Pedersen U, Rasmussen P B, & Lawesson S O. Synthesis of naturally occurring curcuminoids and related compounds. Justus Liebigs Ann. Chem. 1985;1985(8): 1557-1569. https://doi.org/10.1002/jlac.198519850805

Prasad D, Praveen A, Mahapatra S, Mogurampelly S, & Chaudhari S R. Existence of β-diketone form of curcuminoids revealed by NMR spectroscopy. Food Chem. 2021; 360:130000. https://doi.org/10.1016/j.foodchem.2021.130000.

Kim B R, Park J Y, Jeong H J, Kwon H J, Park S J, Lee I C, Ryu Y B, & Lee W S. Design, synthesis, and evaluation of curcumin analogues as potential inhibitors of bacterial sialidase. J Enzyme Inhib Med Chem. 2018; 33(1): 1256-1265. https://doi.org/10.1080/14756366.2018.1488695

Trigo-Gutierrez JK, Vega-Chacón Y, Soares AB, Mima E Gd O. Antimicrobial Activity of Curcumin in Nanoformulations: A Comprehensive Review. Int. J. Mol. Sci. 2021; 22: 7130. https://doi.org/10.3390/ijms22137130

Munir Z, Banche G, Cavallo L, Mandras N, Roana J, Pertusio R, Ficiarà E, Cavalli R, & Guiot C. Exploitation of the Antibacterial Properties of Photoactivated Curcumin as ‘Green’ Tool for Food Preservation. Int. J. Mol. Sci. 2022; 23: 2600. https://doi.org/10.3390/ijms23052600

Kim M K, Park J C, & Chong Y. Aromatic hydroxyl group plays a critical role in antibacterial activity of the curcumin analogues. Nat. Prod. Commun. 2012; 7(1):57-58. https://doi.org/1934578X1200700120.‏

Schraufstätter E, & Bernt H. Antibacterial action of curcumin and related compounds. Nature 1949; 164(4167): 456-457.‏ https://doi.org/10.1038/164456a0

Hussain Y, Alam W, Ullah H, Dacrema M, Daglia M, Khan H, Arciola C R. Antimicrobial Potential of Curcumin: Therapeutic Potential and Challenges to Clinical Applications. Antibiotics 2022; 11: 322. https://doi.org/10.3390/antibiotics11030322 .

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Published

2024-03-29

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Vol. 33 No. 1 (2024): Iraqi J Pharm Sci

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