Antimicrobial Evaluation of Ferulic Acid - 2013

Res Chem Intermed
DOI 10.1007/s11164-013-1192-2
Synthesis and antimicrobial evaluation of ferulic acid

derivatives
Anurag Khatkar Arun Nanda Pradeep Kumar
Balasubramanian Narasimhan
Received: 16 February 2013 / Accepted: 6 April 2013

Springer Science+Business Media Dordrecht 2013
Abstract A series of ferulic acid derivatives (138) was synthesized and characterized by physicochemical and spectral means. The synthesized compounds were
evaluated in vitro for their antimicrobial activity against different Gram-positive
and Gram-negative bacterial and fungal strains by the tube dilution method. Results
of antimicrobial screening indicated that compound 1 was the most active antimicrobial agent (pMICam = 1.83 lM/ml).
Keywords
Ferulic acid derivatives Antibacterial Antifungal
Introduction
The rapid rise in bacterial resistance to traditional antibiotics such as penicillins and
tetracyclines has encouraged a continuing search for new classes of compounds with
novel modes of antibacterial activity. The quinolone antibacterials have emerged as
an area of immense interest because of their broad spectrum of in vitro activity and
their in vivo chemotherapeutic efficiency.
The antimicrobial potential of simple organic acids is well established in the
literature, viz. sorbic acid [1], cinnamic acid [2], anacardic acid [3], veratric acid
[4], myristic acid [5], caprylic acid [6], anthranilic acid [7], and dodecanoic acid [8].
Literature reports reveal that ferulic acid and its derivatives possess a wide spectrum
of biological activities, such as antioxidant [9], anticancer [10], antifungal [11], antiinflammatory [12], and antiviral [13] activities.
In light of the above-mentioned facts, and in continuation of our research efforts
in the field of synthesis, antimicrobial evaluation, and QSAR studies [1419] we
here report the synthesis and antimicrobial evaluation of ferulic acid derivatives.
A. Khatkar A. Nanda P. Kumar B. Narasimhan (&)
Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, India
e-mail: naru2000us@yahoo.com
123
A. Khatkar et al.
Results and discussion

Chemistry
Ferulic acid derivatives (138) were synthesized as outlined in Scheme 1. The
physicochemical properties of the synthesized compounds are presented in Table 1.
The structures of all the newly synthesized compounds were confirmed by IR, 1H
NMR, and elemental analysis which were in full agreement with their structures.
Comp. 2
IR (ATR) cm-1: 3,601 (OH str., phenol), 1,710 (C=O str., ester), 3,008 (CH str.,
aromatic), 1,544 (C=C skeletal str., phenyl), 1,637 (C=C str., alkene), 1,452 (ring
str., quinoline), 754 (CH out of plane bending, quinoline), 1,683 (C=N str.,
quinoline), 3,050 (CH str., ArOCH3); 1H (NMR, DMSO, d ppm): 3.52 (s, 3H,
OCH3), 8.00 (d, 1H, CH (C3) of acrylate), 7.46 (d, 1H, CH (C2) of acrylate),
H3CO
COOH
R-OH H3CO
H2SO4
HO
HO
CO
HO
R-OH
H3CO
HO
9, 12, 13
SOCl2
H3CO
COOR
H3CO
COOR
COCl
HO
N
HO
1, 3-8, 10, 11, 14
2
O
H3CO
H3CO
CONHR
HO
NH
HO
33, 35, 36, 38
34
NH
R2
H2N
H3CO
H3CO
COOH
COCl
HN
O
SOCl2
HO
R7
R4
R5
R3
HO
R4
H
CO N
15-32
R5
R7
R6
Scheme 1 Scheme for the synthesis of ferulic acid derivatives
123
N
O
37
R3
R6
H3CO
CO
HO
NH2
HO
H3CO
Synthesis and antimicrobial evaluation

Comp.
Comp.
NH2
Comp.
CH3
.
.
-
10
.
C4H9
13
C3H7
14
11
NO2
C2H5
12
Comp.
R3
R4
R5
R6
R7
15
16
CH3
NO2
17
Cl
NO2
18
Cl
19
Cl
20
CH3
21
OCH3
22
CH3
CH3
23
CH3
CH3
24
CH3
CH3
25
NO2
26
NO2
27
NO2
28
CH3
Cl
CH3
OCH3
29
30
31
32
33
34
35
C3H7
36
C4H9
37
38
Scheme 1 continued
123
A. Khatkar et al.
Table 1 Physicochemical properties of synthesized ferulic acid derivatives (138)
Comp.
Mol. formula
M. Wt.
mp. (C)
Rf Valuea
(%) Yield
C16H15NO2
285
124126
0.72
72
C19H15NO4
321
208210
0.70
64
C16H20O4
276
220222
0.68
82
C14H18O4
250
203205
0.64
70
C13H16O4
236
112114
0.62
78
C17H16O4
284
246248
0.74
84
C16H13NO6
315
8890
0.68
76
C20H28O4
332
252254
0.72
60
C11H12O4
208
268270
0.70
88
10
C15H20O4
264
213215
0.68
66
11
C14H18O4
250
180182
0.70
88
12
C12H14O4
222
223225
0.74
66
13
C13H16O4
236
246248
0.78
70
14
C16H14O4
270
120122
0.72
82
15
C16H15NO3
269
252254
0.72
74
16
C17H16N2O5
328
108110
0.64
62
17
C16H13ClN2O5
348
112114
0.62
76
18
C16H14ClNO3
303
100102
0.70
82
19
C16H14ClNO3
303
195197
0.74
70
20
C17H17NO3
283
148150
0.78
87
21
C17H17NO4
299
268270
0.74
58
22
C18H19NO3
297
213215
0.68
64
23
C18H19NO3
297
124126
0.62
85
24
C18H19NO3
297
208210
0.64
80
25
C16H14N2O5
314
220222
0.68
72
26
C16H14N2O5
314
180182
0.70
76
27
C16H14N2O5
314
223225
0.62
82
28
C17H17NO3
283
228230
0.72
85
29
C16H13ClFNO3
321
117119
0.64
74
30
C17H17NO3
283
120122
0.68
68
31
C17H17NO4
299
148150
0.72
76
32
C16H16FNO3
287
228230
0.70
77
33
C17H17NO3
283
241243
0.67
78
34
C20H17NO3
319
208210
0.71
72
35
C13H17NO3
235
217219
0.69
76
36
C14H19NO3
249
210212
0.73
81
37
C14H17NO4
263
234236
0.82
69
38
C16H14N2O4
298
198200
0.79
79
TLC mobile phase: Benzene: Chloroform (7:3)
123
7.477.98 (m, 9H, ArH); Anal. Calculated for C19H15NO4: C, 71.02; H, 4.71; N,
4.36; Found: C, 71.05; H, 4.70; N, 4.40.
Comp. 6
aromatic), 1,544 (C=C skeletal str., phenyl), 1,656 (C=C str., alkene), 3,077 (CH
str., ArOCH3), 1,335 (NO2 sym. str., ArNO2); 1H (NMR, DMSO, d ppm): 3.37 (s,
3H, OCH3), 8.10 (d, 1H, CH (C3) of acrylate), 6.91 (d, 1H, CH (C2) of acrylate),
6.948.13 (m, 7H, ArH); Anal. Calculated for C16H13NO6: C, 60.95; H, 4.16; N,
4.44; Found: C, 60.98; H, 4.18; N, 4.41.
Comp. 8
aromatic), 1,513 (C=C skeletal str., phenyl), 1,615 (C=C str., alkene), 3,109 (CH
str., ArOCH3); 1H (NMR, DMSO, d ppm): 3.73 (s, 6H, OCH3), 5.93 (d, 1H, CH
(C3) of acrylate), 5.80 (d, 1H, CH (C2) of acrylate), 5.816.93 (m, 3H, ArH); Anal.
Calculated for C11H12NO4: C, 63.45; H, 5.81; Found: C, 53.65; H, 3.10.
Comp. 26
IR (ATR) cm-1: 3556 (OH str., phenol), 1,725 (C=O str., 20 amide), 3,072 (CH
str., aromatic), 1,545 (C=C skeletal str., phenyl), 1,692 (C=C str., alkene); 2,983 (C
H str., ArOCH3); 1H (NMR, DMSO, d ppm): 3.59 (s, 3H, OCH3), 7.57 (d, 1H, CH
(C3) of acrylate), 6.95 (d, 1H, CH (C2) of acrylate), 6.987.55 (m, 7H, ArH), 9.94 (s,
1H, NH of amide); Anal. Calculated for C16H14N2O5: C, 61.14; H, 4.49; N, 8.91;
Found: C, 61.10; H, 4.50; N, 8.95.
Comp. 29
IR (ATR) cm-1: 3,566 (OH str., phenol), 1,692 (C=O str., 20 amide), 3,047 (CH
H str., ArOCH3); 1,042 (CF str., C6H3ClF), 732 (CCl str., C6H3ClF); 1H (NMR,
DMSO, d ppm): 3.35 (s, 3H, OCH3), 7.53 (d, 1H, CH (C3) of acrylate), 7.37 (d, 1H,
CH (C2) of acrylate), 7.468.53 (m, 6H, 2 ArH), 8.63 (s, 1H, NH of amide); Anal.
Calculated for C16H13ClFNO3: C, 59.73; H, 4.07; N, 4.35; Found: C, 59.70; H, 4.05;
N, 4.39.
Comp. 30
H str., ArOCH3), 2,911 (CH str., alkane); 1H (NMR, DMSO, d ppm): 3.56 (s, 3H,
OCH3), 7.54 (d, 1H, CH (C3) of acrylate), 6.47 (d, 1H, CH (C2) of acrylate),
123
A. Khatkar et al.
6.507.54 (m, 7H, ArH), 2.42 (s, 3H, aromatic CH3); Anal. Calculated for
C17H17NO3: C, 72.07; H, 6.05; N, 4.94; Found: C, 72.03; H, 6.00; N, 4.97.
Comp. 33
str., aromatic), 1,552 (C=C skeletal str., phenyl), 1,707 (C=C str., alkene), 3,094 (C
H str., ArOCH3), 2,900 (CH str., alkane); 1H (NMR, DMSO, d ppm): 3.39 (s, 3H,
OCH3), 7.49 (d, 1H, CH (C3) of acrylate), 7.38 (d, 1H, CH (C2) of acrylate), 7.36
7.51 (m, 8H, ArH), 8.55 (s, 1H, NH of amide), 3.99 (d, 2H, CH2 of benzyl); Anal.
Calculated for C13H9NO7: C, 72.07; H, 6.05; N, 4.94; Found: C, 72.09; H, 6.07; N,
4.98.
Comp. 37
str., aromatic), 1,537 (C=C skeletal str., phenyl), 1,747 (C=C str., alkene), 3,090 (C
H str., ArOCH3), 3,584 (NH str., morpholine), 1,088 (COC str., morpholine);
1
H (NMR, DMSO, d ppm): 3.41 (s, 3H, OCH3), 7.04 (d, 1H, CH (C3) of acrylate),
6.88 (d, 1H, CH (C2) of acrylate), 7.187.41 (m, 3H, ArH), 8.55 (s, 1H, NH of
amide), 2.502.83 (t, 8H, CH2 of morpholene); Anal. Calculated for C14H17NO4: C,
63.87; H, 6.51; N, 5.32; Found: 63.91; H, 6.55; N, 5.30.
In vitro antimicrobial activity
The synthesized ferulic acid derivatives were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and
antifungal activity against Candida albicans and Aspergillus niger, by the tube
dilution method. From the recorded pMIC values (Table 2), it was observed that
compound 37 was found to be most active against E. coli, having a pMICec value of
1.93. Compound 1 was found to be most active against S. aureus, C. albicans, and
A. niger, having pMICsa, pMICca, and pMICan values of 2.01, 1.71, and 1.71,
respectively. Compound 2 was found to be most active against B. subtilis having a
pMICbs value of 2.01. Compound 1 with a pMICam value of 1.83 was found to be
the most potent antimicrobial agent. The antimicrobial activity of the synthesized
ferulic acid derivatives may be due to fact that the phenolic acid derivatives may
increase lipid solubility and cross the bacterial lipid layer and interrupt the
cytoplasmic constituents as suggested in Hugo et al. [20].
In general, the results of MBC/MFC studies revealed that the synthesized
compounds were found to be [0.140.24 and hence they were bacteriostatic and
fungistatic in action as their MFC and MBC values were 3-fold higher than their
MIC values (a drug is considered to be bacteriosatic/fungistatic when its MFC and
MBC values are 3-fold higher than its MIC value) [21].
123

Table 2 Antimicrobial activity
Comp.
Minimum inhibitory concentration (lM/ml)

E. coli
S. aureus
B. subtilis
A. niger
C. albicans
0.088
0.011
0.011
0.011
0.011
0.019
0.078
0.039
0.019
0.019
0.045
0.045
0.045
0.091
0.091
0.050
0.050
0.050
0.050
0.050
0.053
0.053
0.053
0.053
0.053
0.044
0.044
0.022
0.044
0.022
0.159
0.079
0.040
0.040
0.040
0.019
0.038
0.038
0.075
0.038
0.060
0.060
0.120
0.120
0.060
10
0.047
0.047
0.047
0.095
0.024
11
0.050
0.050
0.100
0.100
0.050
12
0.056
0.056
0.113
0.113
0.056
13
0.212
0.106
0.106
0.106
0.106
14
0.046
0.046
0.046
0.093
0.046
15
0.093
0.093
0.046
0.093
0.046
16
0.076
0.076
0.038
0.076
0.076
17
0.072
0.072
0.036
0.072
0.036
18
0.083
0.083
0.041
0.083
0.041
19
0.083
0.083
0.041
0.083
0.041
20
0.044
0.088
0.044
0.088
0.044
21
0.042
0.084
0.042
0.084
0.042
22
0.042
0.084
0.042
0.084
0.042
23
0.042
0.084
0.042
0.084
0.084
24
0.042
0.084
0.042
0.084
0.084
25
0.040
0.080
0.080
0.080
0.080
26
0.040
0.080
0.040
0.040
0.080
27
0.040
0.080
0.020
0.040
0.080
28
0.088
0.088
0.044
0.044
0.044
29
0.078
0.078
0.039
0.078
0.078
30
0.044
0.088
0.044
0.022
0.022
31
0.042
0.084
0.042
0.021
0.042
32
0.044
0.087
0.044
0.087
0.044
33
0.044
0.088
0.044
0.177
0.022
34
0.039
0.078
0.039
0.157
0.020
35
0.053
0.106
0.053
0.213
0.027
36
0.013
0.100
0.050
0.201
0.050
37
0.012
0.095
0.048
0.095
0.048
38
0.021
0.084
0.042
0.084
0.042
Std.
0.005a
0.005a
0.005a
0.005b
0.005b
Std. Standard
a
Norfloxacin
Fluconazole
123
A. Khatkar et al.
Structureactivity relationship
From the antimicrobial activity results of the synthesized ferulic acid derivatives,
the following structureactivity relationship can be drawn:
Esters of ferulic acid were more potent antimicrobial agents than amides and
anilides. The high antimicrobial activity of esters is also evidenced by the results
of Mahiwal et al. [7].
In the case of antimicrobial activity of synthesized ferulic acid derivatives against
S. aureus, B. subtilis, C. albicans and A. niger p-amino ester of ferulic acid (1) was
found to be most potent antimicrobial agent, which indicated that esters having
electron-donating substituents on p-position of phenyl nucleus will be more potent
antimicrobial agents against S. aureus, B. subtilis, C. albicans and A. niger.
Results of antibacterial screening of synthesized ferulic acid derivatives against E.
coli indicated that the amide derivative of morpholine (37) was found to be the
most potent antibacterial agent. The morpholine having the ether oxygen draws
electron density from nitrogen and makes it the most potent antibacterial agent
against E. coli. This fact is also in accordance with the study of Sharma et al. [22].
The anilide derivatives of ferulic acid have no effect on the antimicrobial
activity as none of the anilide derivatives shows any significant activity against
the proposed microbial strains.
From the abovementioned antimicrobial activity results, it can be concluded that

different structural requirements are necessary for different ferulic acid derivatives
to become active against different microbial targets. This is in accordance with the
results obtained by Sortino et al. [23].
The abovementioned findings are summarized in Fig. 1.
O
H3CO
C N
Morpholine
Increase antibacterial
activity against E. coli
HO
H3CO
COOH
HO
H3CO
COOR
NH2
Increase antimicrobial activity against

S. aureus, C. albicans and A. niger
HO
R
H3CO
Anilides
CONH
HO
Fig. 1 SAR of antimicrobial activity of synthesized ferulic acid derivatives
123
Do not shows the antimicrobial

activity
Conclusion
A series of ferulic acid derivatives (138) was synthesized and evaluated in vitro for
their antimicrobial activity against different Gram-positive and Gram-negative
bacterial and fungal strains by the tube dilution method. The results of antimicrobial
screening indicated that esters and amides of ferulic acid were more potent than
anilides, and compound 1 was the most active antimicrobial agent (MIC = 0.011
lM/ml). The results of MBC/MFC studies indicated that the synthesized
compounds were bacteriostatic and fungistatic in action.
Experimental
All reagents and solvents used in study were of analytical grade and procured
locally. The progress of the reaction was monitored by TLC and products were
purified through recrystallization and purity of the compounds was checked by thin
layer chromatography (TLC) performed on silica gel G-coated plate. The spectral
studies, IR and 1H NMR, were determined by standard methods. Infrared (IR)
spectra were recorded on a FTIR Bruker ATR instrument in cm-1. The 1HNMR
spectra were recorded in DMSO-d6 on a Bruker DRX-300 FTNMR instrument.
Elemental analysis was performed on a PerkinElmer 2400 C, H, N analyzer.
Procedure for the synthesis of 8-hydroxy quinoline esters of ferulic acid (18,
10, 11, 14)
For preparation of ferulic acid chloride, thionyl chloride (0.3 mol) was added
gradually to ferulic acid (0.25 mol) in a round-bottom flask. After addition of
thionyl chloride, the mixture was stirred for 4 h and heated to 80 C for 30 min in
water bath. The excess of thionyl chloride was removed by distillation.
A solution of 8-hydroxy quinoline (0.05 mol) in ether (50 mL) was added to a
solution of ferulic acid chloride (0.05 mol) in ether (50 mL). The mixture was
heated in a water bath until no further evolution of hydrogen chloride was observed
and completion of reaction was checked by single spot TLC. The mixture was
cooled to room temperature and evaporation of solvent yielded the crude product
which was purified by recrystallization with alcohol.
General procedure for the synthesis of amides/anilides of ferulic acid
The solution of corresponding amine/aniline (0.1 mol) in ether (50 mL) was added
dropwise to a solution of ferulic acid chloride (0.1 mol) in ether (50 mL)
maintained at 010 C temperature (Scheme 1). The solution was stirred for 30 min
and the precipitated amide was separated by filtration. The crude amide was
recrystallized with alcohol. In the case of anilides, the precipitated crude anilide was
treated with 5 % hydrochloric acid, 4 % sodium carbonate, and water to remove
residual aniline and the resultant anilide was recrystallized with alcohol.
123
A. Khatkar et al.
General procedure for the synthesis of esters of ferulic acid (9, 12 and 13)
A mixture of ferulic acid (0.08 mol) and appropriate alcohol (0.74 mol) was heated
under reflux in presence of sulphuric acid (Scheme 1) until the completion of the
reaction which was checked by single spot TLC. Then, the reaction mixture was
poured in 200 mL ice cold water, neutralized with sodium bicarbonate solution,
followed by extraction of ester with ether (50 mL). The ether layer was separated,
which on evaporation yielded the ester derivatives of ferulic acid.
In vitro antimicrobial activity
The antimicrobial activity of the synthesized compounds was tested against Grampositive bacteria: S. aureus MTCC 2901, B. subtilis MTCC 2063; Gram-negative
bacterium: E. coli MTCC 1652; and fungal strains: C. albicans MTCC 227 and A.
niger MTCC 8189 using the tube dilution method [24]. Dilutions of test and
standard compounds were prepared in double-strength nutrient broth-I.P. (bacteria)
or Sabouraud dextrose broth-I.P. (fungi) [25]. The samples were incubated at 37 8C
for 24 h (bacteria), at 25 8C for 7 days (A. niger), and at 37 8C for 48 h (C.
albicans), and the results were recorded in terms of minimum inhibitory
concentration.
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Antimicrobial Evaluation of Ferulic Acid - 2013

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Antimicrobial Evaluation of Ferulic Acid - 2013

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Res Chem Intermed

Synthesis and antimicrobial evaluation of ferulic acid

Received: 16 February 2013 / Accepted: 6 April 2013

Ferulic acid derivatives Antibacterial Antifungal

Results and discussion

1, 3-8, 10, 11, 14

33, 35, 36, 38

Scheme 1 Scheme for the synthesis of ferulic acid derivatives

Synthesis and antimicrobial evaluation

TLC mobile phase: Benzene: Chloroform (7:3)

Synthesis and antimicrobial evaluation

Synthesis and antimicrobial evaluation

Minimum inhibitory concentration (lM/ml)

From the abovementioned antimicrobial activity results, it can be concluded that

Increase antimicrobial activity against

Fig. 1 SAR of antimicrobial activity of synthesized ferulic acid derivatives

Do not shows the antimicrobial

Synthesis and antimicrobial evaluation

Synthesis and antimicrobial evaluation

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