Design, Synthesis, Characterization and Biological Evaluation of Novel Depsides as Potential Antibacterials

  • Manoj Kumari More Shri G. S. Institute of Technology and Science, 23 Sir M. Visvesvaraya Marg, Indore, MP, 452003

Abstract

Sixteen depsides were synthesized to screen for their antibacterial activity. All of them were reported for the first time. Their chemical structures were clearly determined by FTIR, 1H NMR, ESI mass spectra. All the compounds were assayed for antibacterial and antifungal activities against two Gram-positive bacterial strains (Bacillus subtilis ATCC 6633) and (Staphylococcus aureus ATCC 29747)and two gram-negative bacterial strains (Escherichia coli ATCC 8739) and (Pseudomonas aeruginosa ATCC 25619) the MIC and zone of inhibition calculated by cup-plate method and serial dilution method and two fungal strains (Aspergillus niger ATCC 90292) and (Candida albicans ATCC 24433)by the micro-broth dilution method.Compound2-(2- propoxy -2-oxoethylphenyl (4-methoxyphenyl)acetate(P6) and 2-(2- propoxy-2-oxoethylphenyl(4-methylphenyl)acetate(P7) showed powerful antibacterial activities against E. coli with MIC of 2.0 40mg/ml while compound 2-(2- propoxy -2-oxoethylphenyl(4-methylphenyl)acetate (P7) and 2-(2- propoxy -2-oxoethylphenyl and (3-methoxyphenyl)acetate (P8) exhibited significant antibacterial activities against B. subtilis with MIC of 3.12 40mg/ml, which were superior to the positive controls amoxycillin trihydrate and ciprofloxacin HCl, respectively and compound 2-(2- propoxy -2-oxoethyl) phenyl 4-methylbenzoate (P8) was found to have highest antifungal activity against Candida albicans ATCC 24433. On the basis of the biological results, quantitative structure activity relationships were discussed.


Keywords: Depsides, Antibacterials, Antifungal, Quantitative structure activity relationship.

Keywords: Depsides, Antibacterials, Antifungal, Quantitative structure activity relationship

Downloads

Download data is not yet available.

Author Biography

Manoj Kumari More, Shri G. S. Institute of Technology and Science, 23 Sir M. Visvesvaraya Marg, Indore, MP, 452003
Shri G. S. Institute of Technology and Science, 23 Sir M. Visvesvaraya Marg, Indore, MP, 452003

References

1. Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T. Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei). Chemical and Pharmaceutical Bulletin 2002; 50(10):1416-7. https://doi.org/10.1248/cpb.50.1416 PMid:12372879
2. Hillenbrand M, Zapp J, Becker H. Depsides from the petals of Papaver rhoeas. Planta Medica 2004;70(04):380-2. https://doi.org/10.1055/s-2004-818956 PMid:15095160
3. Vartia KO. Antibiotics in lichens. In The lichens 1973 Jan 1 (pp. 547-561). Academic Press. https://doi.org/10.1016/B978-0-12-044950-7.50022-2
4. Armstrong RA, Bradwell T. Growth of foliose lichens: a review. Symbiosis 2011;53:1-6. https://doi.org/10.1007/s13199-011-0108-4
5. Ingolfsdottir K, Bloomfield SF, Hylands PJ. In vitro evaluation of the antimicrobial activity of lichen metabolites as potential preservatives. Antimicrobial Agents and Chemotherapy 1985;28(2):289-92. https://doi.org/10.1128/AAC.28.2.289 PMid:3834834 PMCid:PMC180233
6. Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Iitaka Y, Endo A, Kitahara N. Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase. Prostaglandins 1982;24(1):21-34. https://doi.org/10.1016/0090-6980(82)90174-5 PMid:6812170
7. Proksa B, Adamcova J, Sturdikova M, Fuska J. Metabolites of Pseudevernia furfuracea (L.) Zopf. and their inhibition potential of proteolytic enzymes. Die Pharmazie 1994;49(4):282-3.
8. Yanmamoto Y, Miura Y, Kinoshita Y, Higuchi M, Yamada Y, Murakami A, Ohigashi H, Koshimuzi K. Screening of tissue cultures and thalli and some of their active constituents for inhibition of tumor promoter-induced Epstein-Barr virus activation. Chem Pharm Bull 1995;43:1388-90. https://doi.org/10.1248/cpb.43.1388 PMid:7553984
9. Kumar KC S, Müller K. Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth. Journal of Natural Products 1999;62(6):821-3. https://doi.org/10.1021/np980378z PMid:10395495
10. Nielsen J, Nielsen PH, Frisvad JC. Fungal depside, guisinol, from a marine derived strain of Emericella unguis. Phytochemistry 1999;50(2):263-5. https://doi.org/10.1016/S0031-9422(98)00517-2
11. Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y. Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. Journal of Medicinal Chemistry 1997;40(6):942-51. https://doi.org/10.1021/jm960759e PMid:9083483
12. KC SK, Müller K. Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid. European Journal of Medicinal Chemistry 2000;35(4):405-11. https://doi.org/10.1016/S0223-5234(00)00132-X PMid:10858601
13. Beutler JA, McKee TC. Novel marine and microbial natural product inhibitors of vacuolar ATPase. Current Medicinal Chemistry. 2003;10(9):787-96. https://doi.org/10.2174/0929867033457827 PMid:12678782
14. Boyd MR, Farina C, Belfiore P, Gagliardi S, Kim JW, Hayakawa Y, Beutler JA, McKee TC, Bowman BJ, Bowman EJ. Discovery of a novel antitumor benzolactone enamide class that selectively inhibits mammalian vacuolar-type (H+)-atpases. Journal of Pharmacology and Experimental Therapeutics 2001;297(1):114-20.
15. Mirrington RN, Ritchie E, Shoppee CW, Taylor WC, Sternhell S. The constitution of radicicol. Tetrahedron Letters 1964;5(7):365-70. https://doi.org/10.1016/0040-4039(64)80029-0
16. Roe SM, Prodromou C, O'Brien R, Ladbury JE, Piper PW, Pearl LH. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. Journal of Medicinal Chemistry 1999;42(2):260-6. https://doi.org/10.1021/jm980403y PMid:9925731
17. Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ. Bioactive Depsides and Anthocyanins from Jaboticaba (Myrciaria c auliflora). Journal of Natural Products 2006;69(8):1228-30. https://doi.org/10.1021/np0600999 PMid:16933884
18. Solladie G, Ziani-Cherif C. Total synthesis of natural gingerols, the three active principles of ginger. The Journal of Organic Chemistry 1993;58(8):2181-5. https://doi.org/10.1021/jo00060a038
19. Tranchimand S, Tron T, Gaudin C, Iacazio G. First chemical synthesis of three natural depsides involved in flavonol catabolism and related to quercetinase catalysis. Synthetic Communications 2006;36(5):587-97. https://doi.org/10.1080/00397910500406534
20. Xiao ZP, Fang RQ, Li HQ, Xue JY, Zheng Y, Zhu HL. Enamines as novel antibacterials and their structure-activity relationships. European Journal of Medicinal Chemistry 2008;43(9):1828-36. https://doi.org/10.1016/j.ejmech.2007.11.026 PMid:18192085
21. Xiao ZP, Fang RQ, Shi L, Ding H, Xu C, Zhu HL. Synthesis, crystal structure, and growth inhibition of human hepatoma cell (HepG2) of polyphenolic compounds based on gallates. Canadian Journal of Chemistry 2007;85(11):951-7.https://doi.org/10.1139/v07-107
22. Fujita F, Moriyama T, Higashi T, Shima A, Tominaga M. Methyl p‐hydroxybenzoate causes pain sensation through activation of TRPA1 channels. British Journal of Pharmacology 2007;151(1):134-41. https://doi.org/10.1038/sj.bjp.0707219 PMid:17351650 PMCid:PMC2012982
23. Sheldrick 33. SHELXL-97. Program for crystal structure refinement. 1997.
24. Meletiadis J, Meis JF, Mouton JW, Donnelly JP, Verweij PE. Comparison of NCCLS and 3-(4, 5-dimethyl-2-thiazyl)-2, 5-diphenyl-2H-tetrazolium bromide (MTT) methods of in vitro susceptibility testing of filamentous fungi and development of a new simplified method. Journal of Clinical Microbiology 2000;38(8):2949-54. https://doi.org/10.1128/JCM.38.8.2949-2954.2000 PMid:10921957 PMCid:PMC87156
25. Skagerberg B, Cruciani G, Ebert C. Sweden zyxwvutsrqponmlkjih. Quant Struct-Act Relat 1989;8:32-8 https://doi.org/10.1002/qsar.19890080105
26. Scano P, Thomson C. Comparison of semiempirical MO methods applied to large molecules. Journal of Computational Chemistry 1991;12(2):172-4. https://doi.org/10.1002/jcc.540120205
27. Stewart JJ. Plain text manual pages for MOPAC 6. J Am Chem Soc.1985; 107:3902. https://doi.org/10.1021/ja00299a024
28. Software CHEM 3D-6.0, Cambridge Soft Corporation, 100 Cambridge Park, MA 02140-2317, USA.
29. Valstat software developed at the Department of Pharmacy, SGSITS, 23, Park Road, Indore, India
Crossmark
Statistics
57 Views | 5 Downloads
How to Cite
1.
More MK. Design, Synthesis, Characterization and Biological Evaluation of Novel Depsides as Potential Antibacterials. JDDT [Internet]. 15Mar.2024 [cited 19Apr.2024];14(3):100-5. Available from: https://jddtonline.info/index.php/jddt/article/view/6474