Epoxide and hydroperoxide derived from naturally cinnamaldehyde and its Schiff base derivatives

Article abstract of DOI:10.14233/ajchem.2014.16616

Thermal and photo epoxidation, photooxygenation reactions of cinnamaldehyde may be useful tool for the design of drugs to act as potent chemopreventation and anticancer agents. trans-Cinnamaldehyde was isolated from essential oil of cinnamon ( Cinnamonum verum). It was subjected to oxidation reactions either photochemically with hydrogen peroxide or thermally with 3-chloro-peroxybenzoic acid. Schiff base derivative was synthesized through condensation reaction with aniline. It subjected to photooxidation reaction in the presence of tetraphenylporphin as singlet oxygen sensitizer. photochemically oxidation reaction gave the corresponding epoxy derivative together with cis-isomerisation. Whereas, thermally oxidation reaction resulted the corresponding epoxy derivative together with cinnamic acid. In addition, photooxidation reaction of Schiff base derivative led to 1-phenyl-3-phenyliminopropen-1-yl hydroperoxide through endoperoxide derivative. The primary tested of hydroperoxide derivative showed a moderate degree of DNA degradation. trans-Cinnamaldehyde and its derivatives can act as antioxidants. They were trapped the reactive oxygen species (ROS) to give the intermediated epoxides and hydroperoxide derivatives, which could be alkylated or damage DNA, proteins and other biological species

Full text of DOI:10.14233/ajchem.2014.16616

Asian Journal of Chemistry; Vol. 27, No. 8 (2015), 3023-3027
A
SIAN
J
OURNAL OF HEMISTRY
C
http://dx.doi.org/10.14233/ajchem.2015.18813
Photochemical and Antimicrobial Studies of Cinnamaldehyde and its Bioactive Derivatives
1
,2,*
3
SUZAN A. KHAYYAT
and AMNA A. SADDIQ
1
2
3
Faculty of Science and Arts in Rabigh, King Abdulaziz University, Jeddah, Saudi Arabia
Chemistry Department, Faculty of Science for Girls, King Abdulaziz University, Jeddah, Saudi Arabia
Microbiology Department, Faculty of Science for Girls, King Abdulaziz University, Jeddah, Saudi Arabia
*
Corresponding author: E-mail: suzan.khayyat@yahoo.com
Received: 17 October 2014; Accepted: 24 December 2014;
Published online: 27 April 2015;
AJC-17184
trans-Cinnamaldehyde [3-phenyl-2-propanal] was isolated from essential oil of cinnamon (Cinnamonum verum). Schiff base and chalcone
derivatives were synthesized through condensation reaction with acetone, acetophenone and aniline. Chalcone also subjected to
photooxidation reaction in the presence of tetraphenylporphin (TTP) as singlet oxygen sensitizer leading to formation of endoperoxide
through [2+4] cyclo addition. The endoperoxide undergo further breaking to form six diketone derivative. Antifungal and antibacterial
studies were carried out on cinnamaldehyde and its derivatives i.e., chalcone, Schiff base and its dimer. Studies on the antifungal especially
Rhizoctonia solani and Penicillium italicum and antibacterial activity against Klebsiella pneumoniae and methicillin resistant Staphylococcus
aureus (MRSA) were showed that cinnamaldehyde and its derivatives have good antimicrobial.
Keywords: Photooxygenation, trans-Cinnamaldehyde, Chalcon, Tetraphenylporphin, R. solani, P. italicum, S. aureus.
endoperoxides and hydroperoxide derivatives, which could
be alkylated or damage DNA, proteins and other biological
INTRODUCTION
9-11
Plant extracts have been used for centuries for various
species
.
purposes (traditional medicine, industrial applications, food
preservatives) because of their antimicrobial properties and
most of them are categorized under GRAS (generally recognized
EXPERIMENTAL
trans-Cinnamaldehyde: [3-Phenyl-propenal] (1) is the
major component of essential oil of cinnamon which was
extracted from Cinnamomum verum. IR spectra were performed
on a Perkin-Elmer 16 FPC FT-IR spectrophotometer as thin
1
as safe) for human consumption . Many naturally occurring
alkenylbenzene derivatives, usually relatively simple allyl- or
propenylbenzene have been identified as components of various
2
plants or their essential oils . Propenyl benzenes are often used
1
13
films. H NMR and C NMR spectra were obtained in CDCl
3
as starting materials in the chemical synthesis of aroma com-
pounds and fine chemicals. In the chemical industry, these are
widely used as starting materials for synthesizing various
products with applications as food preservatives and flavours.
Although propenyl benzenes are usually toxic for most microbes,
it has been reported recently they can be transformed into high-
solution on a Brucker AVANCE D.P.X. 400 MHz apparatus.
GCMS were determined by Joel JMS 600H, GC Hewlett
Packerd, HP 6890 Series, with capillary column (30 m × 0.32
mm × 0.25 µm) HP-5 cross linked 5 % dimethyl polysiloxane.
A sodium lamp (Phillips G/5812 SON) was used for photo-
irradiation reactions. Thin layer chromatography (TLC) and
preparative layer chromatography (PLC): Polygram SIL G/W
3
valued flavours by certain microorganisms . α,β-Unsaturated
aldehydes are important starting materials invarious synthetic
254, Mecherey-Nagel.A rotatory evaporator (at 20 °C/15 torr)
4
applications . trans-Cinnamaldehyde [3-phenyl-2-propanal
was used to remove the solvents.
(
1a)] is an aromaticaldehyde and main component of bark
5
Test organisms
extract of cinnamon (Cinnamonum verum) . It is present in
essential oils of many plants and are proved to be active against
Fungi pathogenic: Rhizoctonia solani and Penicillium
italicum were obtained by the compilation of the Center for
microbes (Mircen), Faculty of Agriculture, Ain Shams
University-Arab Republic of Egypt. It was cultured on sabaroud
dextrous agar media (Oxioid CM 41) at 25 °C.
6,7
6
8
many pathogenic bacteria , fungi and viruses . Taking into
account important activities of plant phenylpropenoides and
their derivatives. Furthermore, phenylpropenoides were trapped
the activated oxygen species in vivo to give the intermediated

3
024 Khayyat et al.
Asian J. Chem.
+
+
Rhizoctonia solani: It is the most important pathogen
159(20) (C
6
H6) [M -COC
6
H
5
], 131 (20) [M -C
2
O
2
C
6
H ], 97
5
12
involved in cotton seedling disease also rhizoctonia root and
crown rot (RRCR) of sugar beet is caused by the soil borne
fungus Rhizoctonia solan and it can affect potato plants from
planting to harvest. It colonizes belowground potato plant
(70) (C ).
H
6 5
Biological activity of cinnamaldehyde: Cinnamaldehyde
and its derivatives were tested against the fungal species
Rhizoctonia solani and Penicillium italicum, the bacterial species
methicillin resistant Staphylococcus aureus and Klebsiella
pneumonia.
Antifungal activities: Diffusion method was used to
evaluate the antifungal activities of the tested compounds as
follows: 1.0 and 0.5 mL of the tested compounds dissolved in
13
surfaces in response to root and shoot exudates .
Penicillium italicum: It is wound invading pathogens that
causes decay on stored citrus fruits damaged by insects, animals,
early splits, mechanical harvesting, chilling and environmental
stresses. Green and blue mould caused by Penicillium digitutum
and P. italicum, respectively, are the most important postharvest
-1
chloroform (CHCl ) (100.0 µg mL ) were added to 50 mL of
3
14
disease of fruits worldwide .
sabaroud dextrous agar media, then poured into sterile Petri
dishes (9 cm in diameter) and left to solidify. Mycelia discs
measuring 6 mm diameter were taken from the growing
margins of cultures of R. solani and P. italicum (on SDA) and
transferred on the surface in the middle of Petri dishes then
incubated in 25 °C for 6 days in dark. The diameters of the
Bacteria pathogenic: Klebsiella pneumonia and methicillin
resistant Staphylococcus aureus (MRSA) from Laboratory of
Jeddah King Fahad Hospital in SaudiArabia. It were cultured
on Mueller Hinton media (Oxioid CM 41) at 37 °C.
Methicillin resistant Staphylococcus aureus (MRSA) is
one of the dangerous pathogenic bacteria that lived mainly in
nasal membranes and skins of human or animals causing
inflammations, blisters, sources as well as complication of
acute wounds and burns resulting in inflammation of urinary
1
7
fungal growth were measured after 2, 4 and 6 days (Tables 1
and 2).
Antibacterial activities
15
(a) 1 mL and 0.5 mL of the tested compounds dissolved
tract, ear, eye and blood sepsis .
-1
in chloroform (CHCl ) (100.0 µg mL ) were added into nutrient
3
Klebsiella pneumonia is an opportunistic pathogen that
causes a significant proportion of hospital-acquired urinary
tract infections, pneumonia, septicemias and soft tissue
broth media (Oxioid): The nutrient broth contained then 1 mL
from suspension of methicillin resistant Staphylococcus aureus
and Klebsiella pneumonia (10 CFU/µL) at 37 °C for 24 h
was added to it. The growth rate was measured monitoring
change in optical density at 650 nm using a spectrophotometer
after 24 h (Table-3).
b) The agar disc diffusion method was employed for the
determination of antibacterial activities 1a, 2, 3, 4, 5 and 6 .
6
16
infections .
General photo-oxygenation of aromatic compounds
4): A solution of 4 (10 mmol) in different solvents according
(
18
to the type of sensitizers was irradiated externally by means
of sodium lamp at -5 ºC. During the irradiation a continuous
stream of dry oxygen gas was allowed to pass through the
reaction mixtures at a slow rate to avoid evaporation of solvent.
The solvent was evaporated at 20 ºC/15 Torr. The crude products
were purified by column chromatography on silica gel adsor-
bent by eluting with a mixture of petroleum ether 60-80 ºC
(
19
6
Suspension of the tested microorganisms (10 CFU/µL) was
spread on Mueller Hinton Agar (Oxioid) for bacteria, filter
paper discs (6 mm in diameter) were soaked with 20 µL of the
stock solutions and placed on the inoculated plates. After
keeping at 2 °C for 2 h, they were incubated at 37 °C for 24 h.
The diameter of the inhibition zones were measured in milli-
meters (Table-4).
2
and ether (9:2) .
1
,5-Diphenyl-penta-2,4-dien-1-one (4): Yield (90%)
needle yellow crystal, m.p. 100 °C, C17 14O (M 234.282). IR
H
-
1
Data analysis:Analysis of data was carried out by student’s
t-test for comparing the means of experimental and control
spectrum, νmax, cm : 3030, 2754, 1783, 1589, 1450,1258 1005.
1
H NMR spectrum, δ (ppm): 7.035 t (1H, 4- H, J = 4.7 Hz)
20
groups .
7
7
8
4
.10 d (1H, 5-H, J = 15 Hz), 7.34 d (1H-2-H, J = 7 Hz), 7.37-
\
\
.52 comp. pat. (5H, phenyl protons), 7.58 t (2 H, 3 , 5 -H, J =
RESULTS AND DISCUSSION
\
.12 Hz), 7.6 t (1H, 4 -H, J = 4.7 Hz), 7.63 dd (1H, 3-H, J =
Cinnamaldehyde derivativesi.e., phenyl-(3-phenyl-allylidene)-
amine (Schiff base) (2), 1,9-diphenyl-nona-1,3,6,8-tetraen-5-
one (3) and 1,5-diphenyl-penta-2,4-diene-1-one (chalcone) (4)
were prepared by means of condensation of the respective
carbonyl component in trans-cinnamaldehyde with aniline ,
acetone and acetophenone respectively (Scheme-I).
Interestingly, the photo induced oxygenation of compounds
in the presence of tetraphenylporphin (TPP) as singlet oxygen
sensitizer led to the formation of 1,5-diphenylpent-3-ene-1,2,5-
trione (5) as a sole photo-products.
The structure of compound 5 was established by spectral
measurements. IR spectrum contained an absorption band at
\
\
13
.7Hz), 7.98 d (2H, 2 , 6 -H, J = 7 Hz). C NMR spectrum, δ
4
2\,6
2
4\\
(
ppm): 125 (C ), 127 (C ), 127.5 (C ), 128.2 (C ), 128.4
3
\,5\
5
3\\,5\\
2\\,6\\
4\
(C
), 129 (C ), 129.2(C ), 132.5 (C ), 136 (C ), 138
1\
1\\
3
1
(
2
C ), 142 (C ),145 (C ), 190 (C ). Mass spectrum; m/z ( Irel %):
35 (10) [M ], 234 (100) [M ].
,5-Diphenyl-penta-3-ene-1,2,5-trione (5): Yield (30 %)
O (M 264.282). IR spectrum, νmax, cm :
918, 1686, 1450, 1244, 1037. H NMR spectrum, δ (ppm):
.85 d (1H, 3- H, J = 4 Hz) 7.33 d (1H, 4-H, J = 4Hz)), 7.46 t
3H, (3 ,4 ,5 )-H, J = 18.15 Hz) H), 7.53 t (3H, (3 , 4 5 )-H, J
7.15 Hz), 7.83 d (2H, 2 , 6 -H, J = 7 Hz), 8.01 d (2H, 2 , 6 -
H, J = 7 Hz). C NMR spectrum, δ (ppm): 190 (C=O), 148
C ), 145 (C ), 139 (C phenyl), 137 (C phenyl), 130
21
+1
+
22
1
-
1
Colourless oil, C17
H
12
3
4
1
2
6
(
=
\
\
\
\\
\\, \\
\
\
\\
\\
13
-1
-1
1
686 cm for carbonyl group, which is shifted from 1783 cm
in the starting material. H NMR spectrum of 5 showed doublet
at δ 6.85 ppm and δ 7.33 ppm from protons on C and C
respectively, as triplet at δ 7.46 and at δ 7.53 ppm for protons
4
3
1\\
1\
(
(
1
2
\,6\,2\\,6\\\
3\,5\,3\\,5\\
C
), 124 (C
). GC-Mass data; retention time 21.52
min, m/z (Irel %): 264, 282 (5) [M ], 234 (100) [M -O ],
3
4
+1
+2
2

Vol. 27, No. 8 (2015)
Photochemical and Antimicrobial Studies of Cinnamaldehyde and its Bioactive Derivatives 3025
TABLE-1
EFFECT OF DIFFERENT CONCENTRATIONS OF 1a, 2, 3, 4, 5 AND 6 ON THE RADIAL GROWTH AND
INHIBITION OF Penicillium italicum GROWN ON SOLID MEDIA (mm/disc; MEAN OF REPLICATES ± SE)
Incubation (days)
Concentration
Treatment
Control
2
4
6
%
(ppm)
Radial growth
3.533 ± 1.584
Inhibition (%)
0.00
Radial growth
6.117 ± 1.82
Inhibition (%)
0.00
Radial growth
8.532 ± 2.012
Inhibition (%)
0.00
0.0
**
**
**
0
1
0
1
0
1
0
1
0
1
0
.5
.0
.5
.0
.5
.0
.5
.0
.5
.0
.5
.0
2.433 ± 1.548
1.633 ± 0.733
1.617 ± 0.726
0.667 ± 0.333
2.667 ± 1.194
2.633 ± 0.733
0.533 ± 0.120
1.633 ± 0.924
0.967 ± 0.433
0.467 ± 0.211
1.239 ± 342
31.135
53.778
54.231
81.120
24.511
56.956
84.913
53.778
72.629
86.781
64.930
75.035
3.617 ± 1.619
2.217 ± 1.000
3.167 ± 1.424
2.233 ± 0.567
3.583 ± 1.603
1.450 ± 0.752
3.517 ± 1.577
3.017 ± 1.349
2.088 ± 1.300
1.767 ± 0.819
2.890 ± 0.009
1.567 ± 2.061
40.869
63.756
48.226
63.495
41.425
58.958
42.504
50.678
65.865
71.113
52.754
74.382
4.150 ± 1.857
2.833 ± 1.070
51.359
66.795
25.773
45.300
58.192
69.725
19.327
36.908
64.838
76.676
57.337
76.558
1a
*
*
*
*
*
6.333 ± 1.49
2
*
**
*
4.667 ± 0.760
3.567 ± 1.596
2.583 ± 1.156
6.883 ± 1.871
5.383 ± 1.517
3.000 ± 1.165
1.990 ± 0.651
3.640 ± 0.432
2.000 ± 0.213
3
4
5
6
**
**
**
**
**
1
**
0.882 ± 411
*
(ns)
Significant at P ≤ 0.05; Significant at P ≤ 0.01; Non-significant at P ≤ 0.05
TABLE-2
EFFECT OF DIFFERENT CONCENTRATIONS OF 1a, 2, 3, 4, 5 AND 6 ON THE RADIAL GROWTH AND
INHIBITION OF Rhizoctonia solani GROWN ON SOLID MEDIA (mm/disc; MEAN OF REPLICATES ± SE)
Incubation (days)
Concentration
Treatment
Control
2
4
6
%
(ppm)
Radial growth
6.667 ± 0.105
4.833 ± 0.173
Inhibition (%)
0.00
Radial growth
7.667 ± 0.214
Inhibition (%)
0.00
Radial growth
9.000 ± 000
Inhibition (%)
0.00
0.0
*
0
1
0
1
0
.5
.0
.5
.0
.5
27.508
52.497
46.002
79.496
10.499
51.504
34.333
46.497
70.196
86.620
61.586
80.050
6.467 ± 0.165
15.651
46.524
44.789
76.092
17.399
48.258
23.425
48.037
54.923
79.640
43.876
71.005
7.133 ± 0.042
20.740
53.333
36.660
42.966
23.333
64.300
17.300
30.766
55.455
77.755
38.311
76.300
1a
**
**
**
3.167 ± 0.105
3.600 ± 0.132
1.367 ± 0.184
5.967 ± 0.184
3.233 ± 0.092
4.378 ± 0.006
3.567 ± 0.124
1.987 ± 0.098
0.892 ± 0.032
2.561 ± 0.008
1.330 ± 0.012
4.100 ± 0.037
4.233 ± 0.092
1.833 ± 0.069
6.333 ± 0.152
3.967 ± 0.021
4.200 ± 0.036
5.700 ± 0.079
5.133 ± 0.042
6.900 ± 0.037
3.213 ± 0.542
7.443 ± 0.321
6.231 ± 0.008
4.009 ± 3.206
2.002 ± 0.014
5.552 ± 0.986
2.133 ± 0.042
*
*
**
2
*
*
*
**
*
3
4
5
6
*
1
.0
.5
.0
.5
.0
.5
.0
0
1
0
1
0
5.871 ± 0.0567
3.984 ± 1.543
3.456 ± 0.054
1.561 ± 0.761
4.303 ± 0.002
2.223 ± 1.125
1
**
*
(ns)
Significant at P ≤ 0.05; Significant at P ≤ 0.01; Non-significant at P ≤ 0.05
O
O
H
NH
2
CH
3
1a
O
O
N
H C
CH
3
3
4
2
O
3
Scheme-I

3
026 Khayyat et al.
Asian J. Chem.
3
\, 4\, 5\
3\\, 4\\,5\\
on C
8
and C
, respectively. Doublet at δ 7.83 and at δ
endoperoxide undergo further breaking to form diketone (5),
the endoperoxide intermediate could not be isolated.
Dimeric cinnamaldehyde (4,6-diphenyl-1,2-dioxane3,5-
dircarboxaldehyde) (6) has been photosynthesis. It was strongly
2\,6\
2\\,6\\
.01 ppm for protons on C and C
respectively.
13
1\
C NMR spectrum of compound 5, the C phenyl and
C phenyl signals were located at δ 137 and 139 ppm respec-
1\\
C
3
4
23
tively. C appeared at δ
C
145 ppm whereas C at δ
C
148 ppm.
124 ppm
inhibited Candida albicans growth more than its monomer .
3
\, 5\, 3\\, 5\\
2\, 6\, 2\\, 6\\
The C
and δ
for three carbonyl groups.
and C
were located at δ
C
CHO
C
130 ppm resonated respectively. Signals at δ 189 ppm
C
Scheme-II illustrates a probable mechanism of the
photosensitized oxygenation of 1,5-diphenyl-penta-2,4-diene-
1
-one (4) in the presence of tetraphenylporphin leading to
O
formation of endoperoxide through [2+4] cyclo addition. The
O
CHO
O
(6)
O
+
Fungal and bacterial diseases are among the most common
infections. The treatment is limited, for many reasons and new
drugs are necessary. In this work, the antimicrobial activity
against Penicillium italicum, Rhizoctonia solani, Staphylococcus
aureus (MRSA) and Klebsiella pneumoniae were also studied,
and the results obtained showed the important antimicrobial
activity of cinnamaldehyde and its derivatives (Tables 1-4).
The antifungal result (Tables 1 and 2) showed that the growth
of P. italicum and R. solani on the solid media were reduced
in the presence of cinnamaldehyde and its derivatives on fungi.
The data in (Table-3) revealed that there were a significant
decrease in the growth of S. aureus and K. pneumoniae on
liquid media, when they were treated by cinnamaldehyde and
its derivatives. The same result has been explained in the
diffusion method which showed inhibition zones around the
filter paper discs (Fig. 1). If the inhibition zone measures 2
and 3 mm, then the complex has a good antibacterial action.
If the inhibition zone measures more than 3 mm across, then
it is considered very effective but if there is no inhibition zone
then the complex has no activity on the bacterial growth and
H
H C
2
1
a
O
C
O
H
C
H
H
H+
OH
O
H
C
H
C
H
24
will not be retained for treatment . It is clear from Table-4,
the emergence of the inhibition of the growth rate of pathogenic
bacteria S. aureus and K. pneumonia as a result of various
transactions, with 2,4,5,7, 7-1 and dimar. It was found that
when the transaction intended to 7-1 report inhibition zone
formed around the filter papers saturated with about 18.22 ±
-
H O
2
H
O
O
0
.00 and 12.02 ±. 014 mm respectively, while appearance lesser
extent of the inhibition zone of bacteria of the dimer reaching
.21 ± 40.0 and 5.42 ± 221 mm for each of the S. aureus and
K. pneumonia.
O
3
4
1O2
+4 cyclo add.
2
O
O
O
O
H
H
-H2
O
O
(a)
(b)
5
Fig. 1. Effect of 1,5-diphenyl-penta-3-ene-1,2,5-trione (5) on radial growth
of fungi grown on the solid media (a) Penicillium italicum (b) control
Scheme-II

Vol. 27, No. 8 (2015)
Photochemical and Antimicrobial Studies of Cinnamaldehyde and its Bioactive Derivatives 3027
TABLE-3
EFFECT OF VARIOUS CONCENTRATIONS OF 1a, 2, 3, 4, 5 AND 6 ON THE DRY WEIGHT OF
Staphylococcus aureus AND Klebseilla pneumoni AFTER 24 h (MEAN OF REPLICATES ± SE)
Concentration
Staphylococcus aureus
Klebsiella pneumoniae
Treatment
Control
(
ppm)
Growth rate
Inhibition (%)
0.0
Growth rate
Inhibition (%)
0.0
0.0
85.000 ± 1.826
30.333 ± 0.211
22.533 ± 0.201
64.733 ± 0.015
41.667 ± 0.201
70.000 ± 0.121
35.000 ± 0.004
77.000 ± 0.001
57.331 ± 0.242
23.124 ± 0.002
16.223 ± 0.110
76.013 ± 0.540
65.200 ± 0.081
90.000 ± 0.966
45.020 ± 0.365
24.867 ± 0.128
56.022 ± 1.142
43.100 ± 0.030
61.303 ± 0.008
40.700 ± 0.212
68.051 ± 0.112
53.114 ± 0.271
25.561 ± 0.200
14.942 ± 0.001
65.020 ± 0.401
58.223 ± 0.400
*
*
*
*
0.5
1.0
0.5
1.0
0.5
1.0
0.5
1.0
0.5
1.0
0.5
1.0
64.70
74.11
23.84
51.23
17.64
58.82
9.41
32.55
72.79
80.91
10.57
23.29
49.97
72.37
37.75
52.11
31.88
54.77
46.61
40.98
71.59
83.39
27.75
35.30
1
a
*
**
*
2
**
**
*
3
4
5
6
*
*
*
*
*
*
**
(ns)
Significant at P ≤ 0.05; Significant at P ≤ 0.01; Non-significant at P ≤ 0.05
3
4
.
.
P. Xu, D. Hua and C. Ma, Trends Biotechnol., 25, 571 (2007).
N. Nordqvist, C. Björkelid, M. Andaloussi, A. Jansson, S. Mowbray,
A. Karlén and M. Larhed, J. Org. Chem., 76, 8986 (2011).
S. Ali, A.A. Khan, I. Ahmed, M. Musaddiq, K.S. Ahmed, H. Polasa,
L.V. Rao, C.M. Habibullah, L.A. Sechi and N. Ahmed, Ann. Clin.
Microbiol. Antimicrob., 4, 20 (2005).
N.S. Shashidar, Ph.D. Thesis, Studies on Bioactive Natural Compounds
for Their Antimicrobial and Antioxidant Properties, Department of
Microbiology, Osmania University, Hyderabad, India (2002).
It has been concluded that trans-cinnamaldehyde and its
derivatives can act as antioxidants. They were trapped the reac-
tive oxygen species (ROS) to give the intermediated epoxides
and hydroperoxide derivatives, which could be alkylated or
damage DNA, proteins and other biological species.
From the above result cinnamaldehyde and its derivatives
show high activity against the growth of bacteria and fungi,
but the inhibition was in bacteria more than of fungi, this may
be explained on the basis bacteria is prokaryotic but fungi are
eukaryotic and the sensitivity of prokaryotic is different than
that of eukaryotic because the changes in the cell wall and
plasma membrane and also the nuclear substances moreover.
Cinnamaldehyde and its derivatives can act as fungicidal and
bactericidal agents. The results revealed that the inhibitory
effect of 5 on rate growth of P. italicum was more effect than
R. solani.
5
6
.
.
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9
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1
1
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5
against showed more inhibitory effect on S. aureus than
K. pneumoniae.
Conclusion
1
Studies on the antifungal especially Rhizoctonia solani
and Penicillium italicum and antibacterial activity against the
Klebsiella pneumoniae and methicillin resistant Staphylococcus
aureus (MRSA) were showed that cinnamaldehyde and its
derivatives have a good antimicrobial activity.
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