Ritmaleni, Sardjiman, Indah Purwantini
Ritmaleni1,3*, Sardjiman1,3, Indah Purwantini2
1Department of Pharmaceutical Chemistry, Gadjah Mada University, Yogyakarta, Indonesia.
2Department of Biological Pharmacy, Faculty of Pharmacy, Gadjah Mada University, Yogyakarta, Indonesia.
3Curcumin Research Center, Faculty of Pharmacy, Gadjah Mada University, Yogyakarta, Indonesia.
Volume - 14,
Issue - 2,
Year - 2021
PGV-6, HGV-6 and GVT-6 are three among curcumin analogs that successfully synthesized. These analogs have a monoketone on their structure. They have two kind of substituents on their aromatic rings, chloro- and hydroxyl-group. According to SAR analysis, these compounds will have a very good activity as antimicrobial agents. This research is aimed to study the antimicrobial activity of those three compounds by using micro-dilution method. Synthesis of PGV-6, HGV-6 and GVT-6 are carried out by using the aldol condensation reaction between a keton (cycopentanone, cyclohexanone, acetone) and aromatic aldehyde (3,5-Dichloro-4-hydroxybenzaldehyde) in acid condition. First work was to see the inhibition percentage and the second experiment is to see the lowest sensitivity against microbes (bacteria and fungi), of three compounds by using micro-dilution method. From the results, it was obtained that the antimicrobial test against seven bacteria and one fungus, showed that PGV-6 only inhibits the growth of Staphylococcus aureus (SA) bacteria; HGV-6 inhibits Klebsiella pneumonia (KP), Escherichia coli (EC), Pseudomonas aeruginosa (PA) and Staphylococcus aureus (SA) bacteria; GVT-6 inhibits the growth of Klebsiella pneumonia (KP), Escherichia coli (EC), Staphylococcus aureus (SA), Streptococcus faecalis (SF) bacteria. None is active against Candida albicans (CA) fungi. GVT-6 is still sensitive against bacteria at 250 ?L/mg of the concentration. GVT-6 is promising to be more developed as antimicrobial agents as confirmed by its docking study.
Cite this article:
Ritmaleni, Sardjiman, Indah Purwantini. Antimicrobial Activity of Curcumin Analog PGV-6, HGV-6 and GVT-6. Research J. Pharm. and Tech. 2021; 14(2):599-604. doi: 10.5958/0974-360X.2021.00107.4
Ritmaleni, Sardjiman, Indah Purwantini. Antimicrobial Activity of Curcumin Analog PGV-6, HGV-6 and GVT-6. Research J. Pharm. and Tech. 2021; 14(2):599-604. doi: 10.5958/0974-360X.2021.00107.4 Available on: https://www.rjptonline.org/AbstractView.aspx?PID=2021-14-2-3
1. Venugopalan P, Deepthi TV. 2014, Chemical and Pharmacological Studies on Curcuminoids. Asian J. Research Chem. 7(3):355-365.
2. Tripathi K. 2009, Curcumin-The Spice of Life-I. Research J. Pharmacognosy and Phytochemistry. 1(3):153-161.
3. Tripathi K. 2009, Curcumin-The Spice of Life-II. Research J. Pharmacognosy and Phytochemistry. 1(3):162-168.
4. Parvathi P, Geetha RV. 2014, Spices and Oral Health. Research J. Pharm. and Tech. 7(2):235-237.
5. Latheeshjlal L, Murala S, Mehul VJ, Swetha G, Swapna P. 2011, Bioavailability Enhancement of Curcumin through Mucoadhesive Drug Delivery System. Research. J. Pharm. and Tech. 4(3):457-460.
6. Tamijselvy S, Andal P, Priyatharesini, PI. 2019, One-Pot Synthesis of copper (II) complex of Curcumin di Ketimines as models for blue copper Protein. Research J. Pharm. and Tech. 12(3):1343-1346.
7. Sweetha G, Sangeetha B, Prabhu S. 2013, A Review on Curcumin Nanoparticles and Its Controlled Delivery to Treat Degenerative Diseases. Asian J. Pharm. Tech. 3(4):218-222.
8. Reddy SVA, Suresh J, Yadav HKS, Singh A. 2012, A Review on Curcuma longa. Research J. Pharm. and Tech. 5(2):158-165.
9. Prafulla S, Lata P, Priya R, Vidya S. 2019, Novel Curcumin Derivatives: Targeted for Anti-Inflammatory Activity. Asian J. Research Chem. 12(2):49-54.
10. Satapathy A, Rao MV. 2018, Protective effect of Curcumin on 2, 4- Dichlorophenoxy acetic acid exerted Hepatotoxicity in Mice. Research J. Pharm. and Tech. 11(2):637-642.
11. Hamzah H, Hertiani T, Pratiwi SUT, Murti YB, Nuryastuti T. 2020, The Inhibition and Degradation Activity of Demethoxycurcumin as Antibiofilm on C. albicans ATCC 10231. Research J. Pharm. and Tech. 13(1): 377-382.
12. Jayandran M, Haneefa M, Balasubramanian V. 2015, Synthesis, Characterization and Antimicrobial Activities of Turmeric Curcumin and Curcumin Stabilized Zinc Nanoparticles - A Green Approach. Research J. Pharm. and Tech. 8(4):445-451.
13. Mishra S, Narain U, Mishra R, and Misra K. 2005, Design, development and synthesis of mixed bioconjugates of piperic acidglycine, curcumin-glycine/alanine and curcumin-glycine-piperic acid and their antibacterial and antifungal properties. Bioorg. Med. Chem. 13:1477−1486
14. Gunes H, Gulen D, Mutlu R, Gumus A, Tas T, Topkaya AE. 2016, Antibacterial effects of curcumin: An in vitro minimum inhibitory concentration study. Toxicology and Industrial Health. 32 (2):246 – 250
15. Izui S, Sekine S, Maeda K, Kuboniwa M, Takada A, Amano A, Nagata H. 2016, Antibacterial Activity of Curcumin Against Periodontopathic Bacteria. J Periodontol. 87 (1):83 – 90
16. Gupta A, Mahajan S, Sharma R. 2015, Evaluation of antimicrobial activity of Curcuma longa rhizome extract against Staphylococcus aureus. Biotechnology Reports. 6:51–55
17. Groundwater PW, Narlawar R, Liao VWY, Bhattacharya A, Srivastava S, Kunal K, Doddareddy, M, Oza PM, Mamidi R, Marrs ECL, Perry JD, Hibbs DE, Panda D. 2017, A Carbocyclic Curcumin Inhibits Proliferation of Gram-PositiveBacteria by Targeting FtsZ. Biochemistry. 56:514−524
18. Ritmaleni, 2016, Synthesis of Pentagamavunon-0 : an Improved Technique, Int. J. Pharm. Sci. Rev. Res. 39(1):9-11
19. Ritmaleni. 2016, Synthesis of Curcumin Analogs. Review. Int. J. Pharm. Sci. Rev. Res. 37(1):236-241
20. Meiyanto E, Putri DDP, Susidarti RA, Murwanti R, Sardjiman, Fitriasari A, Husnaa U, Purnomo H, Kawaichi M. 2014, Curcumin and its Analogues (PGV-0 and PGV-1) Enhance Sensitivity of Resistant MCF-7 Cells to Doxorubicin through Inhibition of HER2 and NF-kB Activation. Asian Pac. J. Cancer Prev. 15:179 – 184
21. Da’i, M, Jenie UA, Supardjan AM, Kawaichi M, Meiyanto E. 2007, T47D cells arrested at G2M and hyperploidyformation induced by a curcumin analogue, PGV-1. Indon. J Biotechnol. 12: 1005 – 1012
22. Da’i, M, Supardjan AM, Meiyanto E, Jenie UA. 2007, Isomers geometric and cytotoxic effect curcumin analogue PGV-0 and PGV-1 on T47D cells. Indonesian J. Pharm. 18:40-47
23. Ramayanti O, Brinkkemper M, Verkuijlen S, Ritmaleni, L, Go ML, Middeldorp J. 2018, Curcuminoids as EBV lytic activators for adjuvant treatment in EBV-positive carcinomas. Cancers. 10 (4):89
24. Ritmaleni, Sardjiman, Agustina Y, Wulandari E, Purwantini I. 2016, Potency of Tetrahydropentagamavunon-0 (THPGV-0) and Tetrahydropentagamavunon-1 (THPGV-1) as Antifungi Agent. Int. J. Pharm. Sci. Rev. Res. 41(2):132-135
25. Sardjiman. 2000, Synthesis of Some New Series of Curcumin Analogues, Antioxydative, Antiinflammatory, Antibacterial Activities, and Qualitative – Structure Activity Relationships. PhD Thesis. Gadjah Mada University, Yogyakarta
26. Sardjiman, Reksohadiprodjo MS, Hakim L, van der Goot H, Timmerman H. 1997, 1,5-diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure activity relationship. Eur. J. Med. Chem. 32:625-630
27. Sardjiman, Reksohadiprodjo MS, Timmerman H. 2003, Derivatives of Benzylidene CycloHexanone, Benzylidene Cyclopentanone and Benzylidene Acetone and Their Synthesis. US Patent, 6541672
28. Sardjiman, Reksohadiprodjo MS, Timmerman H. 2004, Turunan Benzilidin Sikloheksanon, Benzilidin Siklopentanon, Benzilidin Aseton dan Pembuatannya. Patent Indonesia. ID 0 012 940
29. Sardjiman, Reksohadiprodjo MS, Timmerman H. 1998, European Patent Application. EP0860422 Kind Code: A1
30. Safitri CINH, Ritmaleni R, Rintiswati N, Sardjiman S, Kaneko T. 2018, Antimycobacterial Activity of Benzylidene Acetone analogues of Curcumin Againts Resistant and Sensitive Mycobacterium tuberculosis. IOSR JDMS. 16(12):21-26
31. Safitri CINH, Ritmaleni R, Rintiswati N, Sardjiman S, Kaneko T. 2018, Evaluation of Benzylidene Acetone, Analog of Curcumin, as New Antituberculosis Drugs. Asian J Pharm Clin Res. 11(4):226-23
32. Rotile CA, Fass RJ, Prior RB, Perkins RL. 1975, Microdilution Technique for Antimicrobial Susceptibility Testing of Anaerobic Bacteria, Antimicrobial Agents and Chemotherapy. 7(3):311 – 315
33. Ruswanto, 2015. Molecular docking empat turunan isonicotino hydrazide pada mycobacterium tuberculosis enoyl-acyl carrier protein reductase (InhA). Vol 13:1.
34. Dany. P., Lattimer. J. M., Prakash. M., Steiner. A.W., 2013. Stellar Superfluids.Inspire, INT-PUB-009.