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Antimicrobial Activity of different Solvent Extracts of Carthamus tinctorius
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DOI: 10.5958/0974-360X.2020.01055.0

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 Research J. Pharm. and Tech. 13(12): December 2020

ISSN 0974-3618 (Print) www.rjptonline.org

0974-360X (Online)

RESEARCH ARTICLE

Chemical Composition and Antimicrobial Activity of different Solvent

Extracts of Carthamus tinctorius Flowers
Sura L. Alkhafaji*1, Abbass M. Kashamar2, Ibrahim H. Alkhafaji1
1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kerbala University, Karbala - 56001, Iraq.
2
Department of Agricultural Crops, Faculty of Agriculture, Kerbala University, Karbala- 56001, Iraq.
*Corresponding Author E-mail: sura.l@uokerbala.edu.iq
ABSTRACT:
Carthamus tinctorius is an annual plant belonging to the Asteraceae family. It is known as safflower. It is
cultivated in Southern Asia, North and South America. It contains many bioactive compounds for which it has
the biological activities, involving antidiabetic, anticancer, antioxidant, anti-ageing, anticoagulant,
hepatoprotective and anti-inflammatory, analgesic and antibacterial activities. The goal of this work is to identify
the chemical constituents of safflower petals and to reveal their antimicrobial activities. The dried petals were
extracted using three solvents, hexane, ethyl acetate and methanol. Safflower was studied by gas
chromatography-mass spectrometry (GC-MS). A total of 78 compounds from the three extracts were defined,
and it was indicated that the highest percentage in ethyl acetate extract go to 4’, 6- Dimethoxyisoflavonne-7-O-β-
D-glucopyranoside (15.6%) and 7, 4’ – dimethoxy-3-hydroxy flavone (8.17%). In methanol extract, the high
percentage belongs to Ascorbic acid, per methyl- (25.16%), Papaverine (8.16%), Tetratricontane (5.99%). In
contrast, Morin (14.06%) and Isolongiflol (22.67%) showed the highest concentration in hexane extract. The
antibacterial activities of Carthamus tinctorius petals were evaluated against Staphylococcus aureus,
Staphylococcus heamolyticus, Escherichia coli, and Pseudomonas aeruginosa by the disc diffusion method and
the minimum inhibitory concentration (MIC). The results show that C. tinctorius has antimicrobial activity
against all the tested bacteria with diverse degrees. The highest antibacterial activity was achieved by ethyl
acetate extract against all gram-positive and gram-negative bacteria involved.

KEYWORDS: Carthamus tinctorius, Safflower, GC-MS, Antimicrobial activity, Plant extract.

INTRODUCTION:
Safflower (Carthamus tinctorius) is an annual, thistle,
semi-spinal plant that belongs to the Asteraceae family
and it grows in a warm climate. Its flowers are yellow,
orange or red (Figure 1). Initially, it is found in Southern
Asia, (especially in China, India, Iran and Egypt),
southern Europe, North and South America 1. The other
producing regions are Turkey, Argentina, Australia, Iraq,
and Russia.
Figure 1: The Flowers of Safflower

The petals, leaves and seeds oil of safflower have many

applications in cosmetic, textile industry, currently as a
food colorant2 and in herbal and traditional medicine.
Safflower was indicated to treat several diseases such as
Received on 24.11.2019 Modified on 07.02.2020 dysmenorrhea, amenorrhea3, cardiovascular4,5,6,7,
Accepted on 28.03.2020 © RJPT All right reserved 8
cerebrovascular , the pain of joint and abdominal pain.
Research J. Pharm. and Tech. 2020; 13(12):6055-6060. Safflower seeds and extracts have been used to stimulate
DOI: 10.5958/0974-360X.2020.01055.0
bone formation and preclude the osteoporosis
occurrence. Seeds possess major antinflammotry9 and

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 Research J. Pharm. and Tech. 13(12): December 2020

antioxidant10,11,12,13, analgesic14, and antimicrobial Extraction Methods:

proerties15. Three hundred grams of the dried flowers were
pulverized in a mechanical grinder then extracted by the
Safflower bioactivities are attributed to the presence of graduated method as the following:
chemical compounds like flavonoids, phenylethanoid,
glycosides, coumarins, steroids, fatty acids and A hundred gram of the dried powder of safflower petals
polysaccharides16 were soaked in 600ml of n –HE for six days then the
extracted product was filtered through a filter paper
Seeds oils contain a considerable amount of (Whatman no. 41), the filtrate was evaporated under a
polyunsaturated fatty acids (i.e., 70% linoleic acids), reduced pressure using a rotatory evaporator at a
10% oleic acid (mainly, monosaturated fatty acid) and temperature of 40˚C to get the HE crude extract.
straightforward amount of stearic acid, palmitic acid,
margaric acid, etc.17,18. Also, the seeds are rich in The flower residues were re-extracted by 600ml of EA
vitamins (Cu, Zn, Mg and Fe), minerals (B carotene, solvent and macerated for another six days then filtered.
Thiamine), alpha, beta, gamma types of tocopherols. The The clear filtrate was again dried under a reduced
petals produce red/yellow pigment which consists of pressure by rotatory evaporator at a temperature of 40˚C
saffiomin A and safflor yellow B)2,19 to yield the extract of EA.

According to medicinal effects and pharmacotherapeutic The flower remains from the second extraction were re-
uses of C. tinctorius, further chemical determination is extracted using ME solvent 600 ml. After maceration for
required to examine the chemical components of this six days, it was filtered. The filtrate was dried using a
plant, for that reason, this present work was aimed to rotatory evaporator at a temperature of 40˚C to get ME
extract the safflower petals of C. tinctorius using three extract. All the extracts were stored for GC-MS analysis.
different solvents (ethyl acetate, methanol and hexane),
then the chemical constituents were identified by GC- GC–MS analysis for identification of C. tinctorius
MS technique. GC–MS is one of the most well-known chemical composition:
analytical techniques in many scientific fields due to its The three extracts were examined by a GC (Agilent
high sensitivity, low detection limit, rapid identificationTechnologies 7890A) interfaced with a mass- selective
and its ability to analyse a number of ingredients in detector (MSD, Agilent 7000) furnished with a polar
analytes concurrently. Also, it is aimed to examine the in Agilent HP-5ms (5% phenyl methyl polysiloxane)
vitro antibacterial activity of the active agents against capillary column (30x0.25mm i. d. and 0.25μm film
Staphylococcus aureus, Staphylococcus heamolyticus, thickness). The carrier gas was Helium with a linear flow
Escherichia coli and Pseudomonas aeruginosa. of 1ml/min, and the volume of injection was 1µl of the
sample. The injector temperature was 200˚C. The
The antibacterial activity of safflower extracts against ionisation potential of 70 eV, interface temperature of
tested bacteria is attributed to phenolic derivatives that 250˚C, and acquisition mass range 50-800 were the MS
are available in the form of ester or rarely in glycosides operating parameters.
form, flavonoids (in the form of glycosides), alkaloids,
terpenoids and other bioactive compounds. The identification of compounds was based on
comparison of their mass spectra and retention indices
MATERIAL AND METHODS: (RIs) with those documented in the Wiley and NIST
Plant sample preparation: mass spectral databases, and authentic samples
Safflower applied in this work was acquired from the (compound available in our laboratories), additional
local market. The orange flowers were washed, then they library data of the GC– MS system or from literature
were dried in the Pharmacognosy Department, College data.
of Pharmacy, Kerbala University, Iraq.
Determination of antibacterial activity:
Solvents and Chemicals: Tested Bacterial strains and culture media
Ethyl acetate EA, methanol ME, and hexane HE were preparation:
used as the extraction solvents in this study. These three The antibacterial activity of the EA, ME and HE extract
analytical grade solvents were purchased from Sigma of safflower was examined against two gram-positive
Aldrich. bacterial strains (Staphylococcus aureus and
Staphylococcus and two gram-negative bacterial strains
which are Escherichia coli and Pseudomonas aeruginosa.
These bacterial strains were isolated and acquired from
the medical laboratory unit, Al-Kafeel Hospital, Karbala.
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 Research J. Pharm. and Tech. 13(12): December 2020

All Bactria were cultured in sterilised nutrient broth and HE extract consist of 40, 35 and 27 identified
(NB) at 37°C for 16-18 h. Nutrient broth (NB, 25g/L), compounds, respectively. These compounds are ranging
Muller-Hinton (MH, 38g/L), was dissolved in distilled from flavonoids and its glucopyranoside, terpenes,
water. The tools that have been used; the glasses coumarins, esters, alkanes, phenols, essential oils,
(pipettes, tubes, Z- rode and beakers), filter paper disc (5 alkaloids, vitamins and others.
mm in diameter) and the solution of NB and MH were
sterilised using autoclave at 15Ibs at 121˚C for fifteen The major components were 4’, 6-
minutes. The concentration of tested bacteria, cultures Dimethoxyisoflavonne-7-O-β- D-glucopyranoside, 7, 4’
were prepared by comparing with 5% McFarnald –dimethoxy-3-hydroxy flavone, Ascaridole, Hexa-
solution (0.05ml BaCl2 solution in broth, and 9.95ml of hydro- farnesol, 9- cis Retinoic acid, 4-hydroxy-7-
H2SO4 solution in 1% in broth) that adjusted to 150x10 6 methoxy-3-(4-methoxyphenyl) coumarin, Gossypetin,
colony-forming unit CFU/ml. 1800µg/mL of each crude Citronellyl tiglate, Papaverine, Tetratricontane,
extract was prepared by dissolving 1.8mg in 1.0ml of Gardenin, Octacosane, Phytanic acid, Morin and
Dimethyl sulfoxide (DMSO). Isolongiflol.

Antibacterial assay: For EA extract, the GC-MS analysis revealed 40

Disc Diffusion Method: compounds. The dominant compounds were 4’, 6-
The antibacterial activity was determined by disc Dimethoxyisoflavonne-7-O-β- D-glucopyranoside
diffusion method and minimum inhibitory concentration (15.6%) and 7, 4’ – dimethoxy-3-hydroxy flavone
(MIC) as mentioned in literature20 With minor (8.17%). Other minor compounds were 6,4’-dimethoxy-
modification. The Petri dishes used (90×15mm) were 7-hydroxyisoflavone (5.92%), isolongifolol (3.66%),
spread with sterilized MH (20ml) solutions, after that ledol (3.55%), phytol (1.03%), 2’-hydroxy-2,3,4’,6’-tetra
200μl of bacteria stock (150×106 CFU/ml); each was methoxy chalcone (3.01%), syringic acid (2.82%) and
spread on the Muller- Hinton agar (MH) medium using Ascaridole (2.82%), as listed in Table 1.
Z-glass rod, after that the two paper discs individually
saturated with 20μl of extract (1800μg/mL) were applied Table 1: Compositions of Carthamus tinctorius petals for EA
extractor solvent
over each of the culture plates previously planted with
No RT/min Name Area%
150×106 CFU/ml cultures of bacteria. Two blank discs 1 7.81 2'-Hydroxy-2,3,4',6'- 3.01
(with DMSO only), standard disc of Gentamycin tetramethoxychalcone
(10μg/disc) that was used as control for comparison, was 2 9.125 Syringic acid 2.82
placed and arranged on MH petri dish. All bacterial 3 9.769 Phytol 1.03
cultures were incubated at 37˚C for 24 h. After 4 9.864 Himbaccol 2.34
5 10.345 2'-Hydroxy-2,4,4',5,6'- 1.69
incubation the zone of inhibition around each paper disc pentamethoxychalcone
was measured, and the antibacterial action was verified. 6 10.489 Longiborneol 1.41
The inhibition zone is outlined as the area with no 7 10.823 7,8-Dihydro-α-ionone 2.49
growth of the tested infectious agent. 8 10.935 Farnesol 1.74
9 11.287 Caryophyllene 1.43
10 11.503 Ascaridole 2.82
Determination of Minimum Inhibitory Concentration 11 11.624 Squalene 1.53
(MIC): 12 11.831 Dihydrophytol 1.55
The minimum inhibitory concentration MIC of each 13 12.066 (S)-(-)-Citronellic acid 1.51
extract was determined for each tested bacteria in 14 12.345 Hexa-hydro-farnesol 2.82
duplicates. The concentration of stock solution 15 12.579 Isophytol 0.81
16 12.854 Phytol 3.57
(1800μg/mL) that prepared by dissolving of 1.8Zmg in 17 13.016 9-cis-Retinoic acid 2.75
1.0ml of DMSO, was diluted twofold to get a 18 13.137 p-Menth-8-en-2-one 2.73
concentration range of (14.07-1800μg/mL) for each 19 13.268 Nerolidol 1.35
sample, and then 100μl of microorganism was added to 20 13.579 Isolongifolol 1.64
96- wells and were enclosed for incubation overnight at 21 13.732 4',6-Dimethoxyisoflavone-7-O-β-D- 15.6
glucopyranoside
37˚C.
22 13.858 cis-Z-α-Bisabolene epoxide 1.01
23 13.934 Ethyl linalool 1.83
RESULTS AND DISCUSSION: 24 14.308 Apigenin 8-C-glucoside 1.89
For identifying the components of safflower petals, GC- 25 14.425 Sesquicineole 1.55
MS analysis was accomplished, and the peaks, numbers 26 14.547 β-Santalol 1.18
27 14.624 trans-Geranylgeraniol 0.87
and types of its compounds were determined. The results 28 14.745 Isolongifolol 3.66
were recorded in Table 1, 2, and 3 show that Safflower 29 14.777 Ledol 3.55
constituents of petals are very diverse, complex and have 30 14.943 6,4'-Dimethoxy-7-hydroxyisoflavone 5.92
a significant difference in percentage. Hence, EA, ME 31 15.182 α-Cadinol 0.98

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 Research J. Pharm. and Tech. 13(12): December 2020

32 15.596 3-Hydroxy-6,2',4'-trimethoxyflavone 0.86 HE extracts. Other important compounds were identified

33 15.848 1,8-Diazabicyclo [5.4.0] undec-7-ene 1.3 such as 4', 6-Dimethoxyisoflavone-7-O-β-D-
34 16.227 1-Hexacosanol 2.62
35 16.447 7,4'-Dimethoxy-3-hydroxyflavone 8.17
glucopyranoside (3.07%), 6,7-Dihydroxy-4-
36 18.595 Quercetin 3,5,7,3',4'-pentamethyl 2.35 phenylcoumarin (2.84%), 6,7-Diallyloxy-4-
ether methylcoumarin (1.4%), 5,7,3',4',5'-
37 19.19 Elemol 1.24 Pentahydroxyflavone (0.56%), 7-Methoxy-4-
38 21.554 4-Hydroxy-7-methoxy-3-(4- 1.64 methylcoumarin (0.34%), 3'-Benzyloxy-5,6,7,4'-
methoxyphenyl) coumarin
39 22.635 7,3',4',5'-Tetramethoxyflavanone 1.64
tetramethoxyflavone (0.34%).
40 22.928 Cedrol 1.13
Table 3: Compositions of Carthamus tinctorius petals for HE
extractor solvent
While in ME extract, the predominant compounds were No RT/min Name Area%
aliphatic acids (31.21%) and alkanes (20.69%). The high 1 4.018 2-Methylthiolane 0.3
percentage belongs to Ascorbic acid, per methyl- 2 5.783 Methimazole 0.31
(25.16%), Octacosane (10.24), Papaverine (8.16%), and 3 7.999 Resorcinol 0.26
4 8.4 7-Methoxy-4-methylcoumarin 0.34
Tetratricontane (5.99%).and 1- naphthalenol (3.74%),
5 9.728 3,4,5-Trimethoxycinnamic acid 0.35
caryophyllene oxide (0.62%) as listed in Table 2. 6 10.07 Cyclizine 0.29
7 10.273 Caryophyllene 0.23
Table 2: Compositions of Carthamus tinctorius petals for ME 8 10.345 p-Cresol, 2,6-di-tert-butyl- 0.28
solvent extractor 9 10.466 Resorcinol, 5-pentyl- 0.29
No RT/min Name Area% 10 10.606 Camphor 0.26
1 3.194 β-Citronellol 0.7 11 10.759 Phenol, 2,3,5,6-tetramethyl- 0.29
2 3.811 1H-Pyrazole, 1,5-dimethyl- 0.35 12 11.07 6,7-Dihydroxy-4-phenylcoumarin 2.84
3 5.428 Resorcinol 0.93 13 11.444 3'-Benzyloxy-5,6,7,4'- 0.34
4 6.252 6-Methoxyluteolin 0.7 tetramethoxyflavone
5 6.855 Thiazolidine-2-carboxylic acid 1.62 14 11.903 L-Pinocarveol 0.31
15 12.52 Citronellyl tiglate 3.65
6 7.342 1-Naphthalenol 3.74
16 12.641 6,7-Diallyloxy-4-methylcoumarin 1.4
7 7.859 2'-Methoxy-α-naphthoflavone 0.74 17 12.903 Caffeine 2.09
8 8.4 3,2'-Dimethoxyflavone 0.97 18 13.065 Isomenthol 1.16
9 8.467 5,7,3',4',5'-Pentahydroxyflavone 0.88 19 13.186 Pinane 0.88
10 12.318 Gossypetin 2.33 20 13.384 5,7,3',4',5'-Pentahydroxyflavone 0.56
11 12.484 Ascaridole 0.49 21 13.515 2'-Hydroxy-2,4',5-trimethoxychalcone 0.32
12 12.588 Caryophyllene oxide 0.62 22 13.862 4',6-Dimethoxyisoflavone-7-O-β-D- 3.07
13 12.876 Citronellyl tiglate 1.11 glucopyranoside
23 14.231 Morin 14.06
14 13.011 5β,7βH,10α-Eudesm-11-en-1α-ol 0.41
24 14.506 Thunbergol 0.86
15 13.155 Pinane 0.77
25 14.925 Patchoulane 2.61
16 13.38 5,7-Dimethoxyflavone 0.5 26 15.438 Isolongifolol 22.67
17 13.565 Isopulegol 0.84 27 15.564 Genkwanin 1.46
18 13.678 7,4'-Dimethoxy-3-hydroxyflavone 2.77
19 14.443 9-cis-Retinoic acid 0.8 This difference in the percentage and number of
20 14.731 Phytol 1.95
components that were extracted by the three extract
21 14.758 Isolongifolol 2.65
solvents can be attributed to the polarity difference of
22 14.911 Papaverine 8.16
solvent extractors.
23 15.105 Gardenin 3.08
24 15.92 Tetratriacontane 5.99
25 16.393 Although the results showed different components and
3-Hydroxy-3',4',5'-trimethoxyflavone 0.61
26 17.348 which were extracted by different solvents, some of the
3-(3,4-Dimethoxyphenyl)-7-methyl-4- 0.47
phenylcoumarin compounds precisely, Isolongiflol; was common in three
27 19.865 Vitamin E extracts with different percentage. Meanwhile, it was
0.82
28 20.532 Ascorbic acid, per methyl- 25.16
detected some of compounds presented in two samples
29 20.649 Squalane and not in others. Hence, 7, 4’ – dimethoxy-3-hydroxy
3.69
30 20.73 Octacosane 10.24
flavone, Phytol, Squalane, ascaridole, 9- cis- retinoic
31 21.383 Vitexin 1.01
acid were found in both EA, and ME extracts. While, 4’,
32 22.081 N-Ethyl-4-piperidine carboxamide 9.01
6- Dimethoxyisoflavonne-7-O-β- D-glucopyranoside,
33 22.473 Longiborneol 0.5
caryophyllene were common in ET and HE extracts. 5,
34 22.775 Phytanic acid 3.63
7,3’,4’,5’-pentahydroxyflavone, and Resorcinol
35 22.905 Geranyl isovalerate 1.75
compounds were founded in both HE, and ME extracts.
The antibacterial activity of the three extracts of dried
As shown in Table 3, Morin (14.06%) and Isolongiflol
petals of C. tinctorius against selected gram-positive and
(22.67%) compounds were the dominant compounds in
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 Research J. Pharm. and Tech. 13(12): December 2020

gram-negative bacteria was determined by a disc increased up to 225µg/ml. However, non-polar solvent
diffusion method and minimum inhibitory concentration HE extracts had a MIC value range between 225 and 900
(MIC). A significant effect of solvent polarity was µg/ml against all bacterial species.
predicted. So, as shown in Table 4, and at 1800 mg/ml,
EA and ME extracts of safflower had an inhibition on all Table 5: MIC of EA, ME and HE extracts of C. tinctorius petals
test organisms. EA manifested the main inhibitory Tested organism Extract MIC value Mg/ml
Escherichia coli EA 28.12
results and ME extracts. EA solvent extract inhibited in ME 112.5
some extent S. haemolyticus and P. aeruginosa, and ME HE 900
extract on P. aeruginosa and S. aureus for which the Pseudomonas aeruginosa EA 28.12
inhibition zone (DIZ) were 12 mm and 8 mm, and 7, 5 ME 112.5
HE 450
mm, respectively. While the inhibition activity of HE Staphylococcus aureus EA 28.12
extracts was the lowest against all type of selected ME 225
bacteria. HE 225
Staphylococcus heamolyticus EA 28.12
Table 4: Antibacterial activity of different extracts of C. tinctorius ME 112.5
petals by disc diffusion method HE 900
Tested organism Type of Extract Inhibition zone
(DIZ) mm Regarding MIC data, the bacterial inhibition activity of
Escherichia coli EA 5 the three extracts against all tested organisms was in
ME 5
HE 5 decreasing order as following: EA extract > ME extract
Pseudomonas EA 8 > HE extracts. The highest antibacterial activity was
aeruginosa ME 7 achieved by EA extract against all gram-positive and
HE 5 gram-negative bacteria. Overall, the high MIC values of
Staphylococcus aureus EA 5
ME 5
the tested bacteria in this study suggest an organism
HE 5 resistance to antibiotics or the plant extract is less active
Staphylococcus EA 12 against pathogens, while the low MIC values for bacteria
heamolyticus ME 7 indicate the efficiency of plant extract.
HE 5

CONCLUSION:
Among gram-positive bacteria, maximum antibacterial
The findings of this study revealed that the safflower
action was obtained against S. haemolyticus followed by
plant consists of several chemical compounds. Seventy-
S. aureus. While, amongst gram-negative strains,
eight chemicals in petals part of C. tinctorius could be
maximum activity was realized against P. aeruginosa
recognised by GC-MS analysis. The chemicals of EA,
followed by E. coli. Contrarily, HE extract showed low
ME and HE extracts from safflower have moderate to
activity against both gram-positive and gram-negative
worthy antibacterial activity against tested pathogens.
organism because it could be inclined by the fact that the
Therefore, it is suggested that these extracts may help to
inhibition zone depends on how the antimicrobial
open the door to discover new antibiotic agents to treat
compound can diffuse equally through the bacterial wall.
many infectious diseases. Further research is needed to
Therefore, for obtaining quantitative results, it was
isolate and identify other secondary metabolites from the
decided to apply MIC procedure to determine the
extracts employed for testing the antibacterial activity
antibacterial activity.
and understanding the principal mechanisms.
The minimum inhibitory concentration (MIC) test was
carried out against S. aureus, S. heamolyticus, E. coli and ACKNOWLEDGEMENT:
P.aeruginosa. MIC results were reported in Table 5. The The authors are grateful to the authorities of Kerbala
results revealed MIC values ranging from 28.12- 900 College of Pharmacy for providing all the necessary
µg/ml. The selected extracts showed the different level facilities to complete this work. the authors are thankful
of the antibacterial effect depends on the tested bacterial to medical laboratory unit, Al-Kafeel Hospital, Karbala
strains. Knowing that very low concentration of extract for providing the bacterial strains.
is required to suppress the growth of bacteria.
CONFLICT OF INTEREST:
According to MIC data, the results indicated that EA The authors declare no conflict of interest.
extract had the same bioactivity against all types of
pathogens in a concentration of 28.12µg/ml. Also, ME REFERENCES:
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