International Journal of Engineering Trends and Applications (IJETA) – Volume 5 Issue 5, Sep-Oct 2018

RESEARCH ARTICLE OPEN ACCESS

Synthesis, Characterization and Biological Activity of a Schiff Base

Derived From Curcumin and 2-Aminophenol and Its Transition
Metal Complexes
Saritha.T.J [1], P.Metilda [2]
Research Scholar in chemistry, Assistant Professor
Nesamony Memorial Christian College Marthandam
Kanyakumari District, Tamil Nadu, India.

ABSTRACT
Schiff bases are important intermediates for the synthesis of various bioactive compounds. However, various studies have shown that
schiff bases derived from biologically active ingredients present in medicinal plants are more effective in biological and medicinal
activity than in its pure form. In this paper Zn(II), Cu(II), Ni(II), Co(II) and Mn(II) complexes were synthesized from schiff bases
derived from curcumin (a yellow bioactive component extracted from curcuma longa) and 2-Aminophenol. The ligand and their
complexes were characterized by powder XRD, SEM-EDAX, and Antioxidant studies. Also the synthesized ligand and metal
complexes have been screened for their antimicrobial activity against E.coli, S.aureus, B.subtilis, P.aeruginosa, K.pneumoniae and
against various fungi like C.albicans and A.niger. Results revealed that the complexes showed enhanced activity than their
corresponding ligand.
Keywords :- Curcumin, 2-Aminophenol, Transition metal complexes, Antioxidant activity, antimicrobial activity.

I. INTRODUCTION
The chemistry of co-ordination compounds with
heterocyclic ligands containing oxygen and nitrogen as donor
atoms has attracted the attention of chemists in recent years[1].
Schiff bases derived from an amino and carbonyl groups are an
important class of compounds that contains azo-methine
nitrogen ie; > C = N linkage which is essential for biological
activity[2]. Several azomethines were reported to posess
remarkable antibacterial[3]-[5], antifungal[6]-[7], anticancer[8]
and diuretic activities[9]. According to scientific research,
Curcumin or 1, 7-bis (4-hydroxy-3 methoxyphenyl)-1, 6-
heptadiene-3, 5-dione or Feruloyl methane, the main bioactive
component of turmeric (Curcuma longa) has been known to
have the medicinal activity, since ancient times and this
molecule has been the object of several investigations in the
field of biological medicine such as antioxygenation, antibiosis,
anti-tumour, anti-inflammatory, anti-carcinogenic[10],
herbicidal activities and Alzheimer’s prevention[11]. Curcumin
has a highly conjugated β-diketone moiety and can be a
powerful natural chelating agent. Complexition of curcumin
with metals has attracted much interest over the past years as it
is one of the useful requirements for the treatment of
alzheimer’s diseases and in-vitro antioxidant activity[12].
Transition metal complexes of 2-Aminophenol based Schiff
bases have been the subject of extensive investigation because
of their wide use in various fields like antidepressants,
antimicrobial, antitumour, nematocide, antiphlogogistic etc[13].
The present investigation deals with the synthesis of metal
complexes of Zn(II), Cu(II), Ni(II), Co(II), and Mn(II) with the
schiff base derived from Curcumin and 2-Aminophenol. The
synthesized ligand and their metal complexes were
characterized by SEM-EDAX and powder XRD. The
synthesized compounds were studied for their antioxidant
activity by DPPH method. Also the ligand and their metal
complexes have been screened for their antimicrobial activities
against the selected bacteria and fungi using the well diffusion
method.
II. EXPERIMENTAL
2.1 Materials and Methods
All the chemicals and solvents used in the preparation
of ligands and their metal complexes were of A.R grade.
Curcumin and 2-Aminophenol were purchased from Sigma-
Aldrich. Metal salts like Zn(II), Cu(II), Ni(II), Co(II) and Mn(II)
chlorides and the solvents were purchased from Merck.
2.2 Synthesis of Schiff base ligand [4,4’-
(1E,3Z,5Z,6E)-3-hydroxy-5-(2-hydroxyphenyl)imino)hepta-
1,3,6-triene-1,7-diyl) bis (2-(methyl peroxy) phenol)]
Curcumin (0.005 mol, 1.8445g) was dissolved in 20 ml
methanol and stirred well at room temperature. Then methanolic
solution of 2-Aminophenol (0.005 mol, 0.5456g) was added to
the prepared curcumin solution. The obtained orange coloured
mixture was stirred and refluxed at 600C in presence of catalytic
amount of glacial acetic acid (1-2 drops) for about 6 hrs. After
cooling, the resulting orange fine precipitate was filtered and
washed well with distilled ethanol repeatedly to remove any
unreacted chemicals. The obtained orange crystals were then
dried at room temperature.
2.3 Synthesis of Schiff base metal complexes.

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 International Journal of Engineering Trends and Applications (IJETA) – Volume 5 Issue 5, Sep-Oct 2018
To the hot solution of schiff base ligand (0.005 mol) in
methanol (20ml) was added a hot methanolic solution (10ml) of
respective metal chlorides (0.005 mol) drop by drop in 1:1
(ligand: metal) molar ratio. PH of the solution was maintained
just below the value of hydrolysis of the metal ion using
alcoholic ammonia. The reaction mixture was magnetically
stirred and refluxed for 4 hrs at 600C. The coloured precipitate
was filtered and washed by cold ethanol to remove the residue
reactants. Finally the obtained powder was dried to get the
complex.
2.4 Determination of antimicrobial Activity
2.4.1. Test organisms:
The in-vitro biological activity of the schiff base and its
metal complexes in DMSO were tested against the bacterial
species such as Escherichia coli, Staphylococcus aureus,
Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacillus
subtilis and fungal species like Candida albicans and
Aspergillus niger by Muller Hinton well diffusion method using
nutrient agar as medium.
2.4.2. Experimental methods:
The agar well diffusion method was used to screen the
antimicrobial activity. Muller Hinton agar medium (20ml) was
poured into each petri plates. The plates were allowed to solidify
for 5min and 100μl inoculum suspension was swabbed
uniformly and allowed to dry for 15 min. Using sterile cork
borer of 8mm diameter, wells were bored into the seeded agar
plates and these were located with a 100μl solution of each
compound in DMSO and all the plates were incubated at 370C
and the diameter of inhibition zone around each disc was
measured after 24hr for bacterial and fungal species. The
inhibition zone was developed at which the concentration was
noted and the results were recorded. From the results, the
activity index was calculated using the formulae.
2.5 Antioxidant assay (DPPH scavenging activity)
The antioxidant activity of the synthesized curcumin
derivatives was evaluated using the DPPH (1,1-Diphenyl-2-
picryl-hydrazyl) free radical scavenging assay[14]. DPPH
scavenging is considered as a good in-vitro model and is widely
used to assess antioxidant efficacy[15]. 100μg/ml of the test
sample solution was added to 4ml of 100M methanolic DPPH at
various concentrations (20, 40, 60, 80 μg). After stirring, the
mixture was incubated for 20 min at room temperature and the
absorbance at 517 nm was measured. Ascorbic acid (100 μg/ml)
was used as the standard. A blank was prepared without adding
standard or test compound (95% methanol). Lower the
absorbance of the reaction indicates higher the free radical
scavenging activity. The capability to scavenge the DPPH
radical were calculated using the equation,
% of inhibition = x 100
ISSN: 2393-9516 www.ijetajournal.org
where Acontrol is the absorbance of the control reaction and
Asample is the absorbance in the presence of test
compounds[16].
III. RESULTS AND DISCUSSIONS
The condensation of curcumin with 2-aminophenol
give the schiff base 4,4’-(1E, 3Z, 5Z, 6E) -3- hydroxy-5-{(2-
hydroxyphenyl)imino) hepta-1, 3, 6-triene-1,7-diyl) bis (2-
methyl peroxy) phenol}. The ligand L2 which coordinated with
Zn2+, Cu2+, Ni2+, Co2+ and Mn2+ ions separately to give coloured
complexes N1, N2, N3, N4 and N5 respectively. The schiff base
ligand L2 and its metal complexes are stable at room
temperature and soluble in almost all organic solvents like
DMSO and DMF.
3.1. X-Ray Diffraction analysis
X-ray diffraction studies of curcumin were investigated
from the angle of 100 to 800. The powder XRD patterns of
ligand (L2) and Cu complex (N2) are recorded in the range 2 =
0-80 A0 were shown in fig: 1.
The average crystalline size dXRD of the complexes was
calculated using Scherrer’s formula[17],
d = 0.89/cos ),
where ‘d’ is the average crystalline size of the phase under
investigation. ‘’ is the wavelength of X-ray beam used. ‘’ is
the full width at half maximum of diffraction and ‘’ is the
Bragg’s angle. From the observed XRD patterns, the average
crystalline size for the ligand L2 and N2 are found to be 71.1nm
and 59.9nm respectively. After complexetion, the particle size
decreases. This suggests that the ligand and the complexes are
nanocrystalline in nature.
3.2 SEM – EDAX Analysis
Morphology of synthesized ligand and complexes were
characterized by SEM analysis. SEM images of ligand (L2) and
Cu complex (N2) were shown in fig:2. SEM picture of the metal
complexes shows that the particles are agglomerated with
controlled morphological structure and the presence of small
grains in non-uniform size. After agglomeration, SEM image of
compounds shows irregular shaped grains with elongated
morphology and increased particle size. The SEM-EDAX
images of L2 and N2 were shown in Fig: 3. The results of
Energy Dispersive X-ray analysis (EDAX) data reveals the
purity of the complex which indicates that there is no elemental
contamination present in the complex. The % content of
elements in the complex is C (71.80), O (24.60), Cl(2.70) and
Cu (1.53) respectively.
3.3 Antioxidant activity
Antioxidant activity evaluation of ligand and its
complexes was measured in terms of decreases in absorbance at
517 nm of DPPH methanolic solution (0.1 mmol) produced by
the effect of each compound as a result of their ability to donate
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 International Journal of Engineering Trends and Applications (IJETA) – Volume 5 Issue 5, Sep-Oct 2018

a hydrogen giving to the reduced form of DPPH radical. The
reducing abilities of the synthesized compounds were
determined by their interaction with the free radical DPPH at
20μg concentrations for 15 min. This investigation indicates that
there is a greatest possibility of finding potent antioxidants. The
antioxidant activity of ligand and metal complexes are given in
Also Co complex (N4) and Mn complex (N5) showed
moderate antifungal activity against Candida albicans but no
activity against Aspergillus niger. Ni complex (N3) shows
moderate activity against A.niger but no activity against
C.albicans when compared L2 with standard nistatin.
5000

table 1. The ligand (L2) and its Cu complex (N2) have exhibited
very good free radical scavenging activity. N3, N4 and N5

2th=8.911 °,d=9.91518
4000

complexes were shown moderate activity. N1 showed less

activity compared to standard. This study determined the
antagonistic activity of the complexes when compared to ligand.

2th=17.303 °,d=5.12094
3000

Lin (Counts)
The bar graph representation of percentage of free radical

2th=21.153 °,d=4.19668

2th=25.673 °,d=3.46716
scavenging activity is shown in fig: 4. 2000

2th=29.296 °,d=3.04609
2th=23.820 °,d=3.73258
2th=7.929 °,d=11.14151

2th=14.570 °,d=6.07471

2th=17.902 °,d=4.95089

2th=24.694 °,d=3.60240

2th=44.618 °,d=2.02921
2th=12.308 °,d=7.18562

2th=19.471 °,d=4.55528
2th=15.922 °,d=5.56176
3.4 Antimicrobial activity

2th=34.920 °,d=2.56734
2th=13.961 °,d=6.33841
1000

The in-vitro biological screening effects of the

investigated compounds were tested against various bacterial
0

species like E.coli, S.aureus, K.pneumoniae, P. aeruginosa, 4 10 20 30 40 50 60 70 80

B.subtilis and fungal species like C.albicans and A.niger.
Amikacin is used as +ve standard for antibacterial and Nistatin
for antifungal studies. The presence of clear zones noted that the
N2- Scale
2-Theta
File: SAIFXR180111B-01(L2).raw - Step: 0.020 ° - Ste
1) Obs. Max: 44.623 ° - FWHM: 0.244 ° - Raw Area
8)
9)
Obs. Max: 19.472 ° - FWHM: 0.227 ° - Raw Area
Obs. Max: 17.888 ° - FWHM: 0.229 ° - Raw Area
16) Obs. Max: 7.943 ° - FWHM: 0.255 ° - Raw Area:
Operations: Smooth 0.210 | Background 0.000,1.000 |
2) Obs. Max: 34.925 ° - FWHM: 0.323 ° - Raw Area 10) Obs. Max: 17.294 ° - FWHM: 0.254 ° - Raw Area
1000
3) Obs. Max: 29.293 ° - FWHM: 0.268 ° - Raw Area
4) Obs. Max: 25.660 ° - FWHM: 0.249 ° - Raw Area
11)
12)
Obs. Max: 15.918 ° - FWHM: 0.238 ° - Raw Area
Obs. Max: 14.566 ° - FWHM: 0.236 ° - Raw Area
5) Obs. Max: 24.686 ° - FWHM: 0.242 ° - Raw Area 13) Obs. Max: 13.966 ° - FWHM: 0.241 ° - Raw Area
6) Obs. Max: 23.832 ° - FWHM: 0.248 ° - Raw Area
7) Obs. Max: 21.159 ° - FWHM: 0.258 ° - Raw Area
14)
15)
Obs. Max: 12.310 ° - FWHM: 0.243 ° - Raw Area
Obs. Max: 8.905 ° - FWHM: 0.268 ° - Raw Area:
900

compounds were active.

800

The antimicrobial activities of ligand and its metal

700

complexes are shown in fig.5-6. Antimicrobial results showed

2th=16.147 °,d=5.48464
that all the synthesized compounds possess biological 600
Lin (Counts)

activity[18].The increased activity of metal complexes may be 500

2th=7.681 °,d=11.50007

2th=33.487 °,d=2.67383
2th=22.375 °,d=3.97024
2th=22.898 °,d=3.88074
considered due to chelation of metal ions with schiff base which 400
2th=16.610 °,d=5.33281

2th=32.646 °,d=2.74074
enhanced lipophilicity due to delocalization of pi-electrons over

2th=45.569 °,d=1.98905
2th=28.695 °,d=3.10851
2th=27.929 °,d=3.19200
300

the whole chelate ring[19]. These increased lipophilicity

enhances the penetration of complexes into the lipid membranes 200

and blocks the meta binding sites in enzymes of 100

microorganisms. These complexes also disturb the respiration 0

Fig.1
process of the cell and thus block the synthesis of proteins, 3 10 20 30 40

2-Theta - Scale
50 60 70 80

which restricts the growth of organisms. This data revealed that
the activity of the ligand enhanced on complexetion but less
File: SAIFXR180111B-02(N2).raw - Step: 0.020 ° - Step time: 59.7 s - WL1: 1.5406 -
1) Obs. Max: 45.564 ° - FWHM: 0.271 ° - Raw Area: 0.582 Cps x deg.
8) Obs. Max: 16.611 ° - FWHM: 0.217 ° - Raw Area: 0.580 Cps x deg.
9) Obs. Max: 16.158 ° - FWHM: 0.246 ° - Raw Area: 1.643 Cps x deg.
2) Obs. Max: 33.483 ° - FWHM: 0.253 ° - Raw Area: 1.186 Cps x deg. Operations: Smooth 0.210 | Background 0.000,1.000 | Import
Powder XRD pattern of ligand of L2 and N2 complex
3) Obs. Max: 32.652 ° - FWHM: 0.274 ° - Raw Area: 0.746 Cps x deg.
4) Obs. Max: 28.689 ° - FWHM: 0.301 ° - Raw Area: 0.436 Cps x deg.

than the standard used [20]. Comparative study of ligand and its 5) Obs. Max: 27.942 ° - FWHM: 0.264 ° - Raw Area: 0.321 Cps x deg.
6) Obs. Max: 22.900 ° - FWHM: 0.320 ° - Raw Area: 1.721 Cps x deg.
7) Obs. Max: 22.372 ° - FWHM: 0.249 ° - Raw Area: 1.127 Cps x deg.

metal complexes showed moderate to their better antibacterial

activty. Mn complex (N5) showed 22mm zone of inhibition
against Staphylococcus aureus, 20mm zone of inhibition against
E.coli and 20mm zone of inhibition against K.pneumoniae. Cu
complex( N2) showed good activity against S.aureus but no
activity against P.aeruginosa. All other complexes show
moderate activity against all other bacterial species. Overall
comparison of the observed data reveals that Mn complex, N5
shows excellent antibacterial activity and can be tested for
further in-vivo studies and can be used as drug. The orders of
activity of synthesized compounds are as follows.
Mn(II) > Cu(II) > Co(II) > Ni(II) > Zn(II).

Fig.2 SEM images of L2 and N2 complex

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 International Journal of Engineering Trends and Applications (IJETA) – Volume 5 Issue 5, Sep-Oct 2018

Fig.4 Bar diagram representation of antioxidant

activity

Fig.3 EDAX specrum of L2 and their metal complex

% of
S.No. Compounds Inhibition
(mg/ml)
Control - 100
1 L2 91
2 N1 14.7
3 N2 91.4 Fig.5 Inhibition zone against screened bacteria and fungi
4 N3 74.2 by the ligand and complexes

5 N4 50.0
6 N5 64.7

Table. 1 DPPH assay of L2 and its complexes

Fig.6 Antimicrobial activities of L2 and their metal complexes

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 International Journal of Engineering Trends and Applications (IJETA) – Volume 5 Issue 5, Sep-Oct 2018

SEM analysis explains the nanocrystalline nature of the

A.niger
Antifungal activity compounds. EDAX studies gives information about metal purity

10

10

17
-
-

-
-
and elemental composition. Antioxidant studies reveal that most
of the synthesized compounds have potential antioxidant
activity. Antimicrobial study showed that all the complexes
albicans
were moderately active against the tested organisms.

10
10

15
C.

-
-
-
-
Comparatively Mn complex (N5) shows higher antibacterial
activity than all other complex which is due to its higher lipid
solubility and can be used as drugs after invivo studies.
P.aeuroginos

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Table 2: antimicrobial activity of L2 and their metal complexes
IV. CONCLUSION
In this study, a schiff base ligand (Curcumin and 2-
Aminophenol) was synthesized. They formed stable complexes
(1:1) with transition metal ions such as Zn(II), Cu(II), Ni(II),
Co(II) and Mn(II). The ligand and its complexes were stable at
room temperature and are completely soluble in almost all
organic solvents. The synthesized compounds were
characterized by XRD and SEM-EDAX analysis. They are also
tested for antioxidant and antimicrobial activities. The XRD and
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