Investigating the Activity of Antioxidants Activities Content in Apiaceae and to Study Antimicrobial and Insecticidal Activity of Antioxidant by using SPME Fiber Assembly Carboxen/Polydimethylsiloxane (CAR/PDMS)

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

J. Environ. Treat. Tech.

ISSN: 2309-1185

Journal web link: http://www.jett.dormaj.com

Investigating the Activity of Antioxidants

Activities Content in Apiaceae and to Study

Antimicrobial and Insecticidal Activity of

Antioxidant by using SPME Fiber Assembly

Carboxen/Polydimethylsiloxane (CAR/PDMS)

1

1*

2

Seyyed Mojtaba Mousa vi , Seyyed Alireza Hashemi , Hossein Esmaeili , Najmeh parvin ,

4

1

3

,

Fathemeh Mojoudi , MohammadAli Fateh , Hamed Fateh , Aziz babapoor Sargol

1

Mazraedoost , Maryam Zarei

1

Department of Medical Nanotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical

Sciences, Shiraz, Iran

2

Department of Chemical Engineering, Bushehr Branch, Islamic Azad University, Bushehr, Iran

3

Department of Chemical Engineering University of Mohaghegh Ardabili (UMA) Ardabil, Iran

Department of Environment, Faculty of Natural Resources, College of Agriculture & Natural Resources,

University of Tehran, Karaj, Iran

Abstract

In present study, the antioxidant content in Apiaceae was investigated by two new methods such as hydraulic distillation

HD) and HS-SPME, and the composition of final product was recognized using gas chromatography and mass spectroscopy. So,

(

in this research, the anti-oxidation property of the essence was examined. For this purpose, the antioxidant activity of Apiaceae

and its stability was inspected in different concentrations (250, 500, 750 and 1000 ppm) using differential scanning calorimetry

with oleic acid. The results showed the similarity between HD and HS-SPME, but the percentages of the compositions were

different. Besides, the frequency of oxides of essence oils in HS-SPME method was higher than HD method. The experiments

performed on the antioxidants activity of the herb, and the results showed that increasing the essence concentration prevents the

oxidation of the oils.

Keywords: Antioxidants, Gas Chromatography, Mass spectroscopy, Scanning calorimetry, Apiaceae

1

significant herb in traditional medical profession, which has

1

Introduction

been used as a treating medicine in many diseases, and

several laboratorial studies have proved such treating

property. Prangos ferulacea is distributed from Eastern

Europe to Middle East and Central Asia (13). This herb has

been used as carminative, laxative, stomach tonic, neuralgia

relief, anti-inflammatory, antivirus, anti-parasite, antifungal

and antibacterial (14-16). Phyto-chemical investigations

lead to separation of Coumarins, alkaloids, Flavonoids, and

Terpenoides from different species of prangos.

Further researches on aerial essences and seeds of

Prangos ferulacea identified 33 types of oils. In the oil

produced from the fruit, 39 compositions were determined

which were mainly consisted of alpha-pinene.

Monoterpenes, sesquiterpene, and Coumarins were the

other essential compositions of the root. Antioxidants are

the compounds protecting and decelerating the oxidation of

other molecules and reducing oxidation speed with

inhibition of free radicals, peroxide decomposition and

chelating up the metals (17-22). The objective of this study

Herbs were used extensively in conventional medical

profession for several diseases. Scientific studies confirmed

the hopeful treatment ability of herbs for different diseases,

including infectious diseases, cancer, atherosclerosis, scald

and Neurological disease (1-4). Although side effects

cannot be ignored totally for such herbs, fewer negative

effects are conceivable for them in comparison with

synthetic medicines, and in many cases they can reduce the

toxicity of other medicines because of antioxidant

properties. Nowadays, new recognized compositions

between the herbs are applied as medicine and can be used

as a key for cheaper disease diagnosis with fewer side

effects (5-12). Apiaceae (Prangos ferulacea) is

a

Corresponding autor: Seyyed Alireza Hashemi,

Department of Medical Nanotechnology, School of

Advanced Medical Sciences and Technologies, Shiraz

University of Medical Sciences, Shiraz, Iran. E-mail:

kempo.smm@gmail.com.

4

12

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

was to elucidate the antioxidant content in Prangos

ferulacea (Apiaceae) using different extraction techniques,

e.g. hydraulic distillation and HS-SPME.

ability of temperature control during extraction process.

The fiber assembly was kept in a 10 ml glass container and

the fiber holder attached to the container. The glass

container was inside the circulating bath to reach the bath

temperature. Then, the fiber assembly was in contact with

upper section for 5 minutes, and then the fiber was pulled

into the plunger. For heat desorption of pulled components

on the fiber, the injection performed immediately into the

GC-MS instrument.

2

Materials and methods

2

.1 Materials

All chemical materials were purchased from Merck and

Fluka companies with desired purity like anhydrite sodium

sulfate with 97% and normal hexane with 95% purity.

2

.3.3 Measurement of Antibacterial Activity of Apiaceae

2

.2 Instruments

The characterization of used instruments is shown in

essential oil on microorganisms

The recommended medium for disk diffusion method is

Nutrient agar, and we performed the test according to the

guidelines of the Clinical and Laboratory Standards

Institute (25-27). First the medium was prepared based on

the proposed procedure then the mentioned medium was

autoclaved and precisely placed in a 50 to 55°C water bath.

Afterward, it was poured into round plastic petri and let to

cool at room temperature. The stock bacterial culture was

set at 0.5 McFarland standard with an optical density of 600

nm, and a sterile swab was applied to add this prepared

culture to Nutrient agar plates. Then the disk blanks which

had been saturated with the samples were located on the

plates and incubated for hours at 37°C to determine the

susceptibility of the samples. In this study, Ampicillin and

sterile water were regarded as positive and negative control

respectively. In final step, all the plates were assessed for

the presence of inhibition zones. The microdilution broth

assay was utilized to specify the minimum inhibitory

concentrations (MICs) of the samples. Briefly, 2-fold serial

dilutions of the samples and control groups were proposed

with Nutrient broth in 96-well microplates. Then the

bacterial stock (0.5 McFarland Standard) was added to

previous suspension in a way that the first concentration

was 6.25 mg/ml. To determine the minimum bactericidal

concentrations (MBCs) of the samples, the obtained result

of previous test could be useful. In a way, the lowest

concentration of samples, which causes no growth of

bacteria, was regarded (MBC). Components of Apiaceae

After analysis, the components of essence oil of Apiaceae

using HD and SPME-HS methods were determined and

shown in Table 3.

Table 1, and characterizations of the used fiber in the

SPME method are also shown in Table 2. SPME fiber

excluding solid phase and SPME fiber holder were made by

SUPELCO (USA).

2

.3 Experimental procedure

.3.1 Hydro-distillation (HD) method

Hydro distillation is a method of extraction, which is

sometimes used instead of steam distillation. This process

of extraction is one of the most used traditional methods of

extraction. In this work, 100 gram of dried herb was

grinded, and the essence oil was extracted by Clevenger

instrument for 3.5 hours. The oil was dried by anhydrous

sodium-sulphate (Na SO ) and kept in the dark and closed

2

4

container till analysis.

2

.3.2 Headspace Solid Phase Microextraction (HS-

SPME) method

Solid-phase microextraction, or SPME, is a solid phase

extraction sampling technique that involves the use of a

fiber coated with an extracting phase, that can be a liquid

(polymer) or a solid (sorbent), which extracts different

kinds of analytes (including both volatile and non-volatile)

from different kinds of media, that can be in liquid or gas

phase. The quantity of analyte extracted by the fibre is

proportional to its concentration in the sample as long as

equilibrium is reached or, in case of short time, pre-

equilibrium, with the help of convection or agitation (23,

2

4). The method carried out using minimum amount of

herb powder (1 g) without using any solvent. The

circulating bath was used in this experiment, which had the

Table 1: Characterization of used instruments

Apparatus

Applications

Model

2

To identify different substances within a test

sample

GC-MS model HP-6890 supplied by Hewlett-

Packard (USA)

GC-MS

15

3

is a physical characterization method used to study

the thermal behavior of herb

DSC

Electric mill grinder

this mill is needed for SPME method

M20 (IKA-WERKE, Germany)

2

Gas chromatography–mass spectrometry

Differential Scanning Calorimetry

3

4

1ꢀ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

Table 2: Characterizations of the used fiber in the SPME method

Characterization of the used fiber in the SPME method

Type of fiber: (carboxen / poly dimethyl siloxane , CAR / PDMS)

Adsorbent thickness: 75 micrometer

Type of adsorbent connections: powerfully network

Color: Black

-

thujene

I= 930

C H

16

MW= 136

1

0

-

pinene

I= 939

C H

16

MW=136

1

0

-

pinene

I= 979

C H16

MW=136

1

0

Myrcene

I= 991

C H

16

MW=136

1

0

4

1ꢁ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

-

terpinene

I= 1017

C H

16

MW=136

1

0

p-cymene

I= 1025

C H

14

MW=134

1

0

Limonene

I=1029

C H

16

MW=136

1

0

1

,8-cineole

I= 1031

C H O

MW=154

1

0

18

(Z)- -ocimene

I=1037

C H

16

MW=136

1

0

4

1ꢂ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

-

terpinene

I= 1060

C H

MW=136

1

0

16

Artemisia triene

I= 1084

C H

16

MW= 136

1

0

-

terpinolene

I= 1089

C H

16

MW=136

1

0

Gamma-terpinene

I= 1199

C H

16

MW=136

1

0

4

1ꢃ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

Fenchyl acetate

I=1220

C12H20O2

MW=196

Anethole

I= 1253

C10H12O

MW=148

Geranial

I=1267

C H O

MW=152

1

0

16

Bornyl acetate

I=1289

C H O

2

MW=196

1

2

20

4

1ꢄ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

Thrpinen4ol

I= 1291

C10H18O

MW=154

(Z)- -farnesene

I= 1443

C H

24

MW=204

1

5

Isobornyl 3-methylbutanoate

I= 1524

C15H26O2

MW=238

Bornyl angelate

I= 1566

C H O

2

MW=236

1

5

24

Figure 1: The mass spectra of identified compounds of Apiaceae

2

.3.4 Test methods of measuring oxidation stability of

that, nitrogen gas removed, and oxygen flowed into the

device, and heating continued up to 280°C. The oxygen

flow was 50 ml/min, and thermal increase was 10 C/min.

The empty crucible was used as control test. During the

dynamic process, samples heated up from 25°C to 280°C

essence oil using DSC

o

Measuring test by DSC carried out with 8 mg sample in

the crucible without lid. The test completed with one

atmosphere nitrogen pressure and 250°C heating. After

4

4ꢅ

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

and oxidation stability of the samples determined from

maximum temperature deflection curve.

then injected into GC-MS. Eventually, all components are

determined using this apparatus.

The mass spectra of identified compounds of Apiaceae are

showed in Figure 1. In this figure, I, MF and MW are

Quartz Index, Molecular Formula, and Molecular Weight,

respectively.

Table 3: The components of essence oil of Apiaceae using

HD and SPME-HS methods

HS-

SPME

Compound

I

HD (%)

(

%)

3

Results and discussions

°

(60 C)

3

.1 Antioxidant activity of essence oil in Apiaceae

α- Thujene

α Pinene-

Pineneβ-

930

0.66

7.75

0.72

1.62

0.53

13.55

1.35

0.34

-

0.88

8.48

0.87

2.33

0.37

12.91

0.78

-

The antioxidant activity of essence in Apiaceae and its

effect was measured in delaying the oxidation of fatty acid

oleic acid). Different concentrations of mentioned essence

939

(

979

such as 250, 500, 750 and 1000 ppm (diluted with distilled

water) were used in acetone as a solvent, and fatty acid

without antioxidant (oleic acid) added to the mixture. The

solution (1% v/w) injected into the oil container rotating

with 1000 rpm speed. Oleic acid without antioxidants used

as a control test. Figure 2 shows the oxidation stability of

Apiaceae and control test according to dynamic process of

DSC device.

Myrcene

991

α Terpinen-

Para-cymene

Limonen

1017

1025

1029

1031

1037

1060

1084

1089

1169

1199

1220

1253

1267

1289

1291

1299

1381

1443

1524

1566

1

,8-cineole

Ocimene(z-beta)

γ- Terpinene

0.24

20.71

-

2

1

00

80

60

40

20

21.4

0.48

0.45

1.59

0.72

0.33

-

control

Artemisia alcohol

α-terpineolene

Thujene4ol

0.34

-

Apiaceae

γ - Therpineol

Fenchy acetate(endo)

Anethol(z)

-

5.56

0.23

0.31

6.31

0.34

10.24

0.23

0.74

10.2

Geranial

-

Bornyl acetate

γ – Therpinental

Acetanisol(meta)

Geranyl acetate

Franesense(z)beta

Isobornyl-3-methyl

Bornyl angelate

0.6

4.19

-

2

50

500

750

1000

0.54

9.42

Concentration (ppm)

Figure 2: Measuring the oxidation stability of samples containing

essence oil of Apiaceae and control test using a dynamic process of

DSC device.

2

.3.5 Separation and identification of components in

essence oils

As the components present in essence oils are known as

The vertical axis is temperature in °C, and horizontal

axis is the concentration in ppm. The process was done

under one atmosphere of nitrogen gas. Also, the oxygen

flow rate and the heat rate were 50 ml /min and 10°C /min,

respectively. As shown in Fig. 2, thermal stability of

Apiaceae increased with increasing temperature. Also, the

temperatures of oxidation stability of Apiaceae and control

test are showed in Table 4.The effect of anti-oxidation

stability of Apiaceae is depicted in Figure 3. For

determining the effect of anti-oxidation, samples were

analyzed at high temperatures. Calculate phenolic

compounds of the concentration the measuring

concentrations Acid gallic of different absorbance

volatile and semi-volatile oils, therefore GC-MS method

was applied for separation and identification of the

components. In order to confirm the identified components

of standard mass spectrum, Quartz index was applied.

Firstly, the Alkanes of C8-C25 were injected into GC-MS,

and deterrence time for each Alkane was measured using

I=100n when ‘n’ is the number of carbons in related

Alkane. Quartz index of essence oils was calculated using

the following equation (28):

I=100n + 100((t -t )/ (trn+1-trn))

rx rn

n: Carbon number of normal Alcan

t_r_n+1: Retention time of unknown compound

t_r_n: Retention time of normal alkane

After dewatering the produced oil, the oil was diluted using

normal hexane (Merck) with the proportion of 1 to 10 and

4

41

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

Table 5 : Amount of phenol in Apiaceae essential oil

1

200

000

Name plant

Apiaceae

Essence

Mg/ꢇꢑꢆꢅꢊꢇꢒꢏꢄꢄꢅꢆ

Extraction

0.37

8

6

4

2

00

0

3

.2 Antimicrobial effect of Apiaceae essential oil on

microorganisms

Inhibitory effect of ethanolic extract and methanolic

extract of Apiaceae against the eight mentioned bacterial

strains and five different yeasts and fungus were evaluated

through disk diffusion method, and the results are shown in

figure 4. At the tested concentrations, ethanolic and

methanolic extract showed the highest mean diameter of

non-growth halo against E. Coli with the mean diameter of

22.8667 and 16.5067 mm respectively. Also, the lowest

mean diameter of non-growth halo for both ethanolic and

methanolic extract was for Terichophyton verrucosum.

In high concentrations both ethanolic and methanolic

extracts of Apiaceae have significant antibacterial effects

against mentioned microorganisms. It can be stated that, by

increasing the concentration value, antibacterial effects

grow in a concentration-dependent manner. Ethanolic and

methanolic extracts of Apiaceae have the highest average

of inhibitory effects against E.coli with the MIC values of

0.390 and 0.781 mg/ml respectively. These mentioned

samples have more significant antibacterial activity against

gram-negative strains, and MBC values verify the

0

50

100

150

200

250

Concentration (ppm)

Figure 3: The temperature measurement of anti-oxidation stability

of Apiaceae according to dynamic process of DSC device

Table 4: phenolic compounds of the concentration

Microliter Acid gallic

distilled water

0

5

10

-

100

400

500

495

490

calculated using the following equation (1):

ꢁꢂꢃꢄꢅꢆꢇꢆꢃꢈ ꢃꢉꢂꢊꢋꢇꢃꢌꢇꢍꢀꢁꢇꢆꢃꢂꢆꢁꢂꢍꢎꢏꢍꢅꢃꢂ

ꢀ

ꢑꢆꢅꢊꢇꢒꢏꢄꢄꢅꢆ

ꢖꢔꢇꢕꢓ

ꢐꢇ

ꢇꢇꢕꢇꢇꢇ

ꢓꢔꢔꢔ

ꢓ

bacteriostatic

performance

of

these

extracts.

Amount of phenol in Apiaceae essential oil has been

reported in Table 5 :

Ethanolic extract

Methanolic extract

3

2

1

0

5

0

5

0

5

0

Microorganisms

Figure.4: Inhibition zone (mm±SD) of Apiaceae essential oil on microorganisms

4

44

Journal of Environmental Treatment Techniques

2020, Volume 8, Issue 1, Pages: 214-224

Table 6: MICs and MBC/MFC values of compounds against microorganisms

Ethanolic

MIC

Extract (mg/ml)

MBC/MFC

Methanolic

MIC

Ecxtract (mg/ml)

MBC/MFC

Microorganism

Arizona

Salmonella

Morganella

Entrobacter

1.562

0.781

3.125

0.390

3.125

0.781

1.562

3.125

6.125

3.125

1.562

6.25

0.781

3.125

0.781

1.562

0.781

6.25

1.562

6.25

1.562

3.125

1.562

12.5

E.coli

0.781

6.25

Klebsia Pesudomon

Pseudomonas aeruginosa

staphylococcus aureus

Candida albicans

Cryptoccus neoformans

Aspergillus flavous

Terichophyton verrucosum

Epidermophyton

6.25

1.562

6.125

6.25

3.125

6.25

12.5

6.25

1

.562

3.125

1.562

3.125

floccodum

Also, the inhibition performances of both ethanolic and

methanolic extracts of Apiaceae against five different

yeasts and fungus are confirmed by MBC tests (Table 6).

Finally it can be concluded that the antibacterial

performance of ethanolic and methanolic extracts of

Apiaceae is acceptable.

devoid of investigated Apiaceae essential oil. The lowest

concentration, which did not show any growth of tested

organisms after macroscopic evaluation, was determined as

Minimum inhibitory concentration (MIC). The activity was

determined by measuring the diameter of the inhibition

zone (in mm). The antimicrobial activities were expressed

as zone of inhibition and minimum inhibitory concentration

(

MIC). Identification of compounds from a crude extraction

4

Conclusion

of ferulacea essential oil was carried out by GC/MS

technique. Finally, Apiaceae essential oil could serve as a

useful source of new antimicrobial agents.

In this study, the antioxidant effect of Apiaceae essence

oil was investigated using oleic acid and Differential

Scanning Calorimetry. By increasing the concentration of

essence oil, thermal stability of oleic acid increases. The

Differential Scanning calorimetry method is practical in

industry for measuring antioxidant properties of oils and

fats because of simplicity, no toxicity, and high speed. The

required time is short and small amount of the sample is

enough. While there is no need for solvent and chemical

reagents, the applied method is also helpful to qualify the

oil and its oxidation stability .The scanning calorimetry

tests on Apiaceae essence oil reveal that antioxidant

activity depends on several parameters including substrate,

oil type, available fatty acids, presence of other materials

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