Synthesis, characterization and biological activities of turmeric

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1 International Journal of Chemical and Natural Sciences Vol. 2, No. 5 (2014): 157-163 Research Article Open Access ISSN: 2347-6672 Synthesis, characterization and biological activities of turmeric curcumin schiff base complex Jayandran. M1, Muhamed haneefa. M1* and Balasubramanian. V2 1 Mahendra Engineering College, Faculty of Chemistry, Namakkal, India. 2 AMET University, Dean & HOD, Faculty of Chemistry, Chennai, India. * Corresponding author: Muhamed haneefa. M; email: [email protected] Received: 16 September 2014 Accepted: 01 October 2014 Online: 10 October 2014 ABSTRACT Schiff bases are an important class of compounds in medicinal and biological fields. However, various studies have shown that schiff bases derived from bioactive ingredients presence in medicinal plants are more effective in biological and medicinal activities than in its pure form. In this paper we have extracted curcumin from turmeric and the resultant curcumin was used to prepare the schiff base complexes by the reaction of curcumin with amino compounds.The curcumin and its schiff base complex were characterized by UV- visible, IR spectroscopy, elemental analytical techniques and biological activities are investigated. Keywords: Curcumin, Curcuma longa L, Curcuminaniline, Solvent extraction, Soxhlet method INTRODUCTION Turmeric is a significant medicinal spice that comes contains azomethine nitrogen, i.e., C=N linkage [12-13]. from the root Curcuma longa L. Its bright yellow Schiff bases have wide applications in food industry, pigment is used as a food coloring agent. Tumeric has dye industry, analytical industry, catalysis, fungicidal, been used for over 2500 years in India as a spice a food agrochemical and biological activities [14]. Several preservative and a dye. After a long period the azomethines were reported to possess remarkable medicinal properties of this spice have been found out antibacterial [15-16], antifungal [17-18], antitumor [1-8]. The turmeric rhizome contains a variety of [19-20], antiviral [21-22], anti-HIV [23], anti pigments among which curcumin is a major pigment. proliferative [24], herbicidal [25] and diuretic The curcuminoids are polyphenols and are responsible activities [26]. In general the most common method for for the yellow color of turmeric and which has been preparing schiff bases is the reacion of aldehydes and shown to have a wide range of therapeutic effects. ketones with primary amines. The reaction is generally Curcumin incorporates several functional groups. The carried out by refluxing the carbonyl compounds and aromatic ring systems, which are phenols, are amines in organic solvents by separating the water as connected by two ,-unsaturated carbonyl groups. formed with an azeotroping agent or by anhydrous The diketones form stable enols and are readily Na2SO4 and MgSO4 [27-32]. deprotonated to form enolates; the ,-unsaturated carbonyl group is a good Michael acceptor and Nowadays, the research field dealing with schiff base undergoes nucleophilic addition. The structure was coordination chemistry has expanded enormously. The first identified in 1910 by J. Miobdzka, Stanisaw importance of schiff base complexes for bioinorganic Kostanecki and Wiktor Lampe.Curcumin is a chemistry, biomedical applications, supramolecular liposoluble compound and can be easily dissolved into chemisty, catalysis and material sciences, marine organic solvent such as methanol, ethanol, and acetone applications, separation and encapsulation processes [10-11]. and formation of compounds with unusual properties and structures has been well recognized and reviewed Schiff bases derived from an amino and carbonyl [33-36]. A considerable number of schiff base compound are an important class of ligands which complexes have potential biological interest, being used 157

2 Jayandran et al. / Int J Chem Natur Sci. 2014, 2(5): 157-163 as more or less successful models of biological Ltd. Pure curcumin powder was obtained from HPLC, compounds. Not only have they played a seminal role in India to prepare standard solution. All reagents were of the development of modern coordination chemistry, analytical grade and used as received. but also they can also be found at key points in the development of inorganic biochemistry, catalysis and Synthesis of curcumin from turmeric optical materials [37-38]. The main component of turmeric, curcumin is quantitatively extracted from turmeric in soxhlet In recent years natural medicinal plants are used very apparatus by using 95% ethanol as a solvent and the much in the various fields of chemistry to enhance the curcumin content was estimated as per the method of biological and medicinal activities of the material. Manjunath et al. [40]. The process is described as Based upon this we were focused on the curcumin due follows briefly. 5.0 g of turmeric dried powder weighed to its significant medicinal purposes to prepare and taken in soxhlet apparatus with 250 ml of ethanol. bioactive schiff base complexes. Recently, we reported The extraction process carried out for 2 1/2 hrs and the the synthesis of curcumin from selected commercial final curcumin extract absorbance was measured at turmeric plants to find out the curcumin rich turmeric 425 nm against alcohol blank. Using the absorbance variety [39]. In continuation with our research work in value the curcumin percentage was calculated. The the present protocol we used the curcumin rich above ethanolic residual extract was evaporated and turmeric to synthesize curcumin for better result dried then recrystalized by 95% ethanol. The standard followed by schiff base ligands effectively. Curcumin curcumin was also processed as the same above and have been extracted first from turmeric by using this standard solution (containing 0.0025g/1ml) was soxhlet extraction technique with 95% ethanol as a read at 425 nm against alcohol blank in solvent then the synthesized curcumin was reacted spectrophotometer and the curcumin content obtained with aniline under certain conditions to prepare by this method is determined and expressed as percent. bioactive schiff base curcuminaniline. The quantification of curcumin in turmeric is normally Synthesis of curcumin schiff base complex based on spectrophotometric measurement. We found Double distilled water has been used throughout the that the synthesized curcumin and curcuminaniline synthesis process. The synthesized pure curcumin (10 were shown better yield and significant biological mmol) was dissolved in ethanol and stirred well at activities. room temperature. Then aniline (10 mmol) solution was added to the prepared curcumin solution. The MATERIALS AND METHODS obtained orange coloured mixture was stirred and The experiment is carried out by the method of soxhlet refluxed at 50 C for 6 hrs in mild acidic condition. After solvent extraction technique to extract the curcumin cooling the resulting orange fine precipitate of from turmeric. The turmeric sample with rich curcmin curcuminaniline schiff base was filtered and washed (BSR-01) has been collected from Agricultural College well with double distilled water repeatedly to remove and Research Institute, Madurai. The purification was any unreacted chemicals then dried in vacuum oven at carried out by the boiling process of this turmeric with 100 C for 1 hr. The obtained orange powdered water and finally dried and powdered. The solvent curcuminaniline was kept in a desiccator over silica gel used for extraction process 95% ethanol and the main for further analyses. The synthesis process was chemical aniline were purchased from E.Merck (India) followed according to the scheme presented in figure 1. O O H2N 500C + HO -H2O O OH O CH3 H3C Curcumin (C21H20O6) O N HO O OH O CH3 H3C Curcuminaniline (C27H25O5N) Fig 1. Representation of Schiff base formation 158

3 Jayandran et al. / Int J Chem Natur Sci. 2014, 2(5): 157-163 Characterization suspension was swabbed uniformly and allowed to dry All samples were stored in a desiccator containing silica for 5 minutes. The concentration of sample at 40 gel for atleast 48 hr at room temperature to ensure mg/disc was loaded on 6 mm sterile disc. The loaded minimal moisture content before spectroscopic disc was placed on the surface of medium and the analysis. The UV-Visible absorption spectra of the extract was allowed to diffuse for 5 minutes and the curcumin and its schiff base complex were measured plates were kept for incubation at 37oC for 24 hrs. At on a Shimadzu UV-Vis V-530A spectrophotometer in the end of incubation, inhibition zones formed around the range of 300 to 600 nm. Elemental analyses were the disc were measured with transparent ruler in carried out with ElementarVario EL III series used to millimeter. collect the micro analytical data (C, H and N) and compared with the calculated theoretical values. Antifungal activity test The fungal strains were inoculated separately in The unmodified and chemically modified curcumin and Sabourauds dextrose broth for 6 h and the suspensions schiff base complex were examined for FT-IR spectra were checked to provide approximately 10 5 CFU/ml. analysis and recorded on a jasco FT-IR/4100 The agar well diffusion method (Perez, 1993) was spectrophotometer with 4cm-1 resolution in the range modified. Sabourauds dextrose agar (SDA) was used of 4000 to 400 cm-1. for fungal cultures. The culture medium was inoculated with the fungal strains separately suspended in Biological assay Sabourauds dextrose broth. A total of 8 mm diameter The antibacterial and antifungal activity of the wells were punched into the agar and filled with the synthesized Curcumin and Curcuminaniline were sample and solvent blanks (hydro alcohol, and hexane). tested against two gram positive bacteria Standard antibiotic (Fluconazole, concentration 1 (Staphylococcus aureus and Bacillus subtilis), two gram mg/ml) was used as positive control and fungal plates negative bacteria (Escherichia coli and Staphylococcus were incubated at 37oC for 72 h. The diameters of zone bacillus) and four fungal species (Candida albicans, of inhibition observed were measured. Curvularia lunata, Aspergillus niger and Trichophyton simii). A comparative study of the growth inhibition RESULTS AND DISCUSSION zone values for curcumin and its schiff base were UV-Vis spectra studies evolved. Curcumin was quantitatively extracted by refluxing the material in alcohol and was estimated Antibacterial activity test spectrophotometrically. The UV-Vis spectra of The disc diffusion method (Bauer et al., 1966) was used curcumin and curcuminaniline are given in figure 2(a- to screen the antimicrobial activity [41]. Stock cultures b) respectively. Curcumin exhibits absorption maxima were maintained at 4oC on slopes of nutrient agar. at around 425 nm can be due either to an n- * Active cultures of experiment were prepared by transition or to a combination of - * and n- * transferring a loopful of cells from the stock cultures to transitions (Figure 2a). The UV-Vis absorption of free test tube of Muller-Hinton broth (MHB) for bacteria curcuminaniline under investigation display mainly that were incubated without agitation for 24 hrs at two bands observed in ethanol within the range 250- 37oC and 25oC respectively. The cultures were diluted 500 nm. The first band showed absorption bands at the with fresh Muller-Hinton broth to achieve optical range 255-295 nm which could be assigned to - * densities corresponding to 2.0106 colony forming and n - * transitions in the aromatic ring or units (CFU/ml) for bacteria. The Muller Hinton Agar azomethine (C=N) while the second band 440-460 nm (MHA) plates were prepared by pouring 15 ml of was assigned to curcumin moiety (Figure 2b). molten media into sterile petriplates. The plates were allowed to solidify for 5 minutes and 0.1% inoculum 2.4 2 Abs 1 -0.1 300 400 500 600 Wavelength [nm] Fig 2a. UV-vis spectrum of CR Fig 2b. UV-vis spectrum of CA 159

4 Jayandran et al. / Int J Chem Natur Sci. 2014, 2(5): 157-163 The extracted curcumin have been quantitatively estimated Elemental Analysis spectrophotometrically and it was converted into percentage The analytical data of curcumin and its schiff base complex of curcumin. The amount of curcumin obtained from this are summarized in table 1. The complexes prepared are method was around 9.24%. This is the higher curcumin stable at room temperature and non-hygroscopic. percentage obtained from turmeric by the Soxhlet extraction technique. Table 1. Elemental analysis data of Curcumin (CR) and Curcuminaniline(CA). Sample code Experimental value Theoretical value C H N C H N CR 69.43 5.20 - 68.47 5.47 - CA 70.16 6.12 4.71 73.12 5.68 3.16 FT-IR Spectra Studies Fig 3. FT-IR spectra of Curcumin (Bottom); Curcuminaniline (Top) IR spectra provide the valuable information about the nature group by the conjugation present the curcumin system. The of the binding mode and functional group present in the strong peak for (C=C) unsaturation remains outside the ring complexes. IR spectrographs of curcumin and was confirmed by the observed peak in the region 1600 cm-1. curcuminaniline were taken by the Shimadzu FTIR 8700 The (C-O) band presence was assigned by the peak found at instrument. From the data obtained, phenolic OH showed its 1000-1250 cm-1. The peak due to the carboxyl group (C=O) weak broad band in the range of 3500-3200 cm-1 which were was observed in both curcumin and its schiff base at around assigned to phenolic OH group of curcumin moiety in both 1625 cm-1. This band in curcuminaniline is shifted to lower the formulations. The weak and broadness of these peaks frequency 1584 cm-1 suggesting the bond breaking of oxygen could be observed mainly due to intra-molecular hydrogen with carbon and formation of azomethine C=N stretching bonding between the enolic OH group with azomethine vibration. Three characteristic peaks in the range of 1520 nitrogen atom. Existence of this enolic OH group in all the 1350 cm-1 conforms the aromatic unsaturation (C=C) as in ligands could be possible only due to stabilization of OH table 2. Table 2. IR spectra bands of curcumin and curcuminaniline Compounds Functional groups (cm-1) (Ph-OH) (C=O) (C=C) (Ar C=C) (C-O) (C=N) Curcumin (CR) 3502 1625 1601 1505 1272 - 1427(3peaks) 1024 1358 Curcuminaniline (CA) 3215 1625 1600 1509 1239 1584 1437(3peaks) 1027 1414 Table 3. Effect of curcumin and curcuminaniline on antibacterial activity Bacterial Species Zone of inhibition diameter (mm sample-1) Standard drug (C) Curcumin(CR) Curcuminaniline(CA) S. aureus 21 12 18 B.subtilis 19 10 14 E. coli 20 17 15 S.bacillus 19 11 17 160

5 Jayandran et al. / Int J Chem Natur Sci. 2014, 2(5): 157-163 Antibacterial activity activity exhibited by the curcumin and its schiff base ligand The antibacterial activities of curcumin and its schiff base were significantly appreciable. The results compared with against two gram-positive (Staphylococcus aureus and standard drug have been indicated that the synthesized Bacillus subtilis) and two gram-negative bacteria (Escherichia compounds were active but activity was lower than the coli and Staphylococcus bacillus) were evaluated and their standard drug and also showed nearly similar activity to the activity was compared to a well-known commercial antibiotic standard drug. Results of antibacterial evaluation is Chloramphenicol. The results are reported in table 3. summarized in figure 4 a. From these results, curcumin and curcuminaniline both were Antifungal activity found to be more active against all the bacteria tested. The Curcumin and its schiff base ligand were determined for their schiff base curcuminaniline has a greater effect against antifungal activity against four fungal strains Candida S.aureus, S.Bacillus and B.subtilis than the curcumin. albicans, Curvularia lunata, Aspergillus niger and Trichophyton Moreover, the zone of inhibition observed for those simii and their activity was compared with standard synthesized products (CR & CA) against E.coli showed the antifungal drug fluconazole. The results were shown in table moderate antibacterial action when compared to the results 4. obtained against other bacterial species. Therefore the Table 4. Effect of Curcumin and its schiff base on antifungal activity Fungal Species Zone of inhibition diameter (mm sample-1) Standard drug (C) Curcumin(CR) Curcuminaniline(CA) C.albicans 19 16 19 C.lunata 19 17 18 A.niger 20 15 16 T.simii 21 16 13 B.subtilis S.aureus 20 22 d emo de mo demo d emo demo d emo de mo dem o demo d emo 18 20 18 d emo de mo dem o demo d emo 16 d emo de mo demo d emo demo Zone of inhibition (mm) 16 14 Zone of inhibition (mm) d emo de mo demo d emo demo d emo de mo dem o demo d emo 14 12 12 d emo de mo demo d emo demo d emo de mo dem o demo d emo 10 10 8 d emo de mo demo d emo demo d emo de mo dem o demo d emo 8 6 6 d emo de mo demo d emo demo d emo de mo dem o demo d emo 4 4 2 d emo de mo dem o demo d emo 2 d emo de mo demo d emo demo 0 0 CA CR Drug CA CR Drug Compounds Compounds E.coli 20 d emo demo demo demo d emo S.Bacillus 18 18 d emo demo demo demo d emo de m o d em o de mo de mo d em o 16 16 Zone of inhibition (mm) 14 d emo demo demo demo d emo 14 de m o d em o de mo de mo d em o Zone of inhibition (mm) 12 12 de m o d em o de mo de mo d em o d emo demo demo demo d emo 10 10 de m o d em o de mo de mo d em o 8 d emo demo demo demo d emo 8 de m o d em o de mo de mo d em o 6 d emo demo demo demo d emo 6 4 de m o d em o de mo de mo d em o 4 2 d emo demo demo demo d emo 2 de m o d em o de mo de mo d em o 0 0 CA CR Drug CA CR Drug Compounds Compounds Figure 4a. Antibacterial activity data of complexes 161

6 Jayandran et al. / Int J Chem Natur Sci. 2014, 2(5): 157-163 C.albicans C.lunata 20 20 de mo d e mo de mo d e mo de mo demo demo demo demo demo 18 18 16 de mo d e mo de mo d e mo de mo 16 demo demo demo demo demo Zone of inhibition (mm) Zone of inhibition (mm) 14 14 de mo d e mo de mo d e mo de mo demo demo demo demo demo 12 12 de mo d e mo de mo d e mo de mo demo demo demo demo demo 10 10 8 de mo d e mo de mo d e mo de mo 8 demo demo demo demo demo 6 6 de mo d e mo de mo d e mo de mo demo demo demo demo demo 4 4 2 de mo d e mo de mo d e mo de mo 2 demo demo demo demo demo 0 0 CA CR Drug CA CR Drug Compounds Compounds A.niger T.simii 22 20 d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo 20 18 d e mo d e mo d e mo d e mo d e mo 18 d e mo d e mo d e mo d e mo d e mo 16 16 Zone of inhibition (mm) Zone of inhibition (mm) 14 d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo 14 12 d e mo d e mo d e mo d e mo d e mo 12 d e mo d e mo d e mo d e mo d e mo 10 10 8 d e mo d e mo d e mo d e mo d e mo 8 d e mo d e mo d e mo d e mo d e mo 6 6 d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo d e mo 4 4 2 d e mo d e mo d e mo d e mo d e mo 2 d e mo d e mo d e mo d e mo d e mo 0 0 CA CR Drug CA CR Drug Compounds Compounds Figure 4 b. Antifungal activity data of complexes From the results, it can be concluded that the activity of the find its use in a wide variety of biological applications schiff base ligand curcuminaniline were showed better due to its significant bioactivities. inhibition compared to curcumin when tested against C.albicans, C.lunata and A.niger fungal species. However the activity of curcuminaniline was almost similar to the Acknowledgements standard antibiotic (Fluconazole) but interestingly, it showed We gratefully acknowledge Department of Chemistry, more activity than curcumin. Results of antifungal evaluation V.O.Chidambaram College, Tuticorin, India for providing UV are summarized in figure 4 b. and IR spectral analysis facility and also SAIF, Cochin, India for elemental analysis facility. We thank AMET University, India and Mahendra Engineering College, India for their CONCLUSION support to do this work. In summary, the bioactive curcumin and its schiff base ligand curcuminaniline synthesized from natural REFERENCES medicinal turmeric extract which showed over all 1. Nadkarni KM, Nadkarni AK (1976). In: Indian MateriaMedica, significant antibacterial and antifungal activities. 3rd Edn., Popular Prakashan Ltd., Bombay. Moreover the schiff base ligand was more active 2. Srinivasan K (2005). Role of spices beyond food flavouring: against C.albicans, C.lunata and A.niger species which Nutraceuticals with multiple health effects. Food Rev. Int. 21: 167-188. was almost similar to standard antibiotic drug and also 3. Jasim Hilo Naama, Ali A. Al-Temimi and Ahmed A. Hussain Al- observed appreciable inhibition activity against Amiery,Study the anticancer activities of ethanoliccurcumin S.aureus and S.bacillus. From this work we could found extract, African Journal of Pure and Applied Chemistry Vol. the biologically more active turmeric (curcumin) 4(5), pp. 68-73, May 2010. 4. Eigner D, Scholz D (1999). Ferula asaofoetida and curcumin variety (BSR-01) and its schiff base complex longa in traditional medical treatment and idet in Nepal. J. curcuminaniline. The synthesized curcuminaniline may Ethnopharmacol. 67: 1-6. 162

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