STUDIES ON THE GROWTH, CHARACTERIZATION, PHYSICOCHEMICAL PROPERTIES AND ANTI-BACTERIAL ACTIVITY OF FERULIC ACID CRYSTALS
Objective: The main objective of this research is to study the chosen Ferulic acid for pharmaceutical application through crystal growth technique. The interest of growing crystals helps in studying the physical and chemical properties of the title compound. The computational method provides a detailed interpretation of the compound under study.
Methods: Crystallization from solution is a very crucial process in the manufacture of active pharmaceutical ingredients (APIs). Ferulic acid (FA) corresponds to monohydroxylatedcinnamic acid. The biological efficiency of this kind of phenolic systems is expected to be dose-and structure-dependent, which renders the studies for the understanding of their multi-functional biological action. In the present work, ferulic acid crystals were grown using slow evaporation technique. The crystalline nature was revealed from the powder x-ray diffraction technique. The functional groups were determined using FTIR and FT-RAMAN spectra and compared with the theoretical data obtained using computational DFT method. Thermal and physicochemical stability of the grown crystal was examined by Thermogravimetric analysis (TGA) and Differential thermal analysis (DTA) studies. The charge transfer within the molecule was studied with the help of Natural Bond Orbital (NBO) analysis. The anti-bacterial activity was carried out for the title compound using disc diffusion method. The test compounds were screened in vitro for their antibacterial activity against two Gram-positive species (B. cereus and B. substilis) and three Gram-negative species (E. coli, P. vulgaris and S. typhi) of bacterial strains by the disc diffusion method.
Results: The grown crystal was pure and crystalline in nature. The functional groups were confirmed by FTIR and FT-Raman analysis. The melting point of the sample was found to be 172 Â°C. The HOMO-LUMO energy gap was calculated as 3.87eV. The first hyper polarizability was found to be 10.612 x 10-30 esu. The molecular geometry revealed the Cs symmetry of the molecule. NBO analysis confirmed the intramolecular charge transfer from lone pair oxygen atom to Ï€*(C1-C6) and Ïƒ*(C17-O19). The compound is dominant for the B. substilis organism which is revealed from the zone of inhibition.
Conclusion: The grown Ferulic acid crystals confirmed to have good anti-bacterial activity and the theoretical study proves the biological activity of the compound.
2. Wargovich M, J Jimenez A, Mc Kee K, Steele VE, Velasco M, Woods J, Price R, et al. Efficacy of potential chemopreventive agents on rat colon aberrant crypt formation and progression G. J Carcinogenesis 2000;21:1149-55.
3. Mori H, Kawabata K, Yoshimi N, Tanaka T, Murakami T, Okada T, et al. Chemopreventive effects of ferulic acid on oral and rice germ on large bowel carcinogenesis. Anticancer Res 1999;19:3775-8.
4. Aruoma OI. Nutrition and health aspects of free radicals and antioxidants. Food Chem Toxicol 1994;32:671-83.
5. Ou S, Kwok KC. Ferulic acid: pharmaceutical functions, preparation, and applications in foods. J Sci Food Agric 2004;84:1261-9.
6. Kayahara H, Miao Z, Fujiwara. Synthesis and biological activities of ferulic acid derivatives G. Anticancer Res 1999;19:3763-8.
7. Akihisa T, Yasukawa K, Yamaura M, Ukiya M, Kimura Y, Shimizu N, Arai K. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. J Agric Food Chem 2000;48:2313-9.
8. Xu LN, Xu DC, Zhang Z. Investigation on the mechanism of sodium ferulate in lowering blood platelet aggregation: effect of sodium ferulate on the equilibrium of TXA 2 and PGI 2. Acta Pharm Sin B 1984;6:414-7.
9. Panizzi L, Catalano S, Miarelli C, Cioni PL, Campeol. In vitro antimicrobial activity of extracts and isolated constituents of geumrivale E. Phytother Res 2000;14:561-63.
10. Jeong. YC, Jae HM, Keun HP. Isolation and identification of 3-methoxy-4-hydroxybenzoic acid and 3-methoxy-4-hydroxy-cinnamic acid from hot water extracts of Hoveniadulcis Thunb and confirmation of their antioxidative and antimicrobial activity. Korean J Food Sci Technol 2000;32:1403â€“8.
11. Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBOVersion3.1 TCI, University of Wisconsin, Madison; 1998.
12. Weinhold F, Landis CR. Valency and bonding: a natural bond orbital donorâ€“acceptor perspective. Cambridge University Press: Cambridge, New York, Melbourne; 2005. p. 215â€“74.
13. Choudhary N, Bee S, Gupta A, Tandon P. Comparative vibrational spectroscopic studies, HOMOâ€“LUMO and NBO analysis of N-(phenyl)-2,2-dichloroacetamide, N-(2-chloro phenyl)-2,2 dichloroacetamide and N-(4-chloro phenyl)-2,2-dichloroacetamidebased on density functional theory. Comput Theor Chem 2013;1016:8â€“21.
14. Pearson RG. Absolute electronegativity and hardness correlated with molecular orbital theory. Proc Natl Acad Sci USA 1986;83:8440â€“1.
15. Jug K, Chiodo S, Calaminici P, Avramopoulos A, Papadopoulos MG. Electronic and vibrational polarizabilities and hyperpolarizabilities of azoles: a comparative study of the structure-polarization relationship. J Phys Chem A 2003;107:4172-83.