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Chemical composition of the essential oils for AnthemisMelampodina from North Saudi Arabia

Jehan Al-humaidi

Chemistry Department, College of Science, Princess Nora Bint Abdul Rhman University,  

DOI : http://dx.doi.org/10.13005/ojc/310453

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Article Published : 04 Nov 2015
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ABSTRACT:

The chemical composition of essential oil of Anthemsmelampodinais determined by GC/MS. The oil was obtained by hydro-distillation and SPME extraction methodsIn the SPME method, a total of 41 constituents were identified monoterpene hydrocarbons (88.89%) were the main class of compounds detected in the SPME method with b-pinene(35.29%), trans-ocimene(23.96%) andterpinolene(15.78%) being detected as the main constituents. On the other hand, hydro-distilled oil was rich in oxygenated sesquiterpene(31.22%).

KEYWORDS:

Anthems melampodina; Hydro-distillation; SPME; GC/MSmonoterpene hydrocarbons; oxygenated sesquiterpenes

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Al-humaidi J. Chemical composition of the essential oils for AnthemisMelampodina from North Saudi Arabia. Orient J Chem 2015;31(4).


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Al-humaidi J. Chemical composition of the essential oils for AnthemisMelampodina from North Saudi Arabia. Orient J Chem 2015;31(4). Available from: http://www.orientjchem.org/?p=12185


Introduction

Anthemis(belonging to the Astraceae family)is a genus of 210 species of flowering plants. Anthemis plants are known to growwidely in Europe, south western Asia, northern and north eastern Africa and southern Arabia.The arabic names for this plant include Qahwiyan,Rebyan and Arbiyar[1]. In Saudi Arabia, the genus Anthemis is represented by 17 species distributed in the central, eastern and northern regions[2]. examples include A. pseudocotula,A. bornmuelleri,A. cotula.A. odontostephenaand A. melampodina[3]. In folk medicine Anthemis species are frequently used for the treatment of various ailments such as digestive problems, insomnia and toothache.Moreover,several studies also showed that different Anthemis species exhibited antiflammatory, antioxidant, antibacterial, antiproliferative and antispasmodic properties[4-8]. Most Anthemisspecies are economically important, due to their use in pharmaceutics, cosmetics and food flavoring[9-13]. Furthermore, chemical investigations on Anthemisspecies revealed that the genus is dominated by sesquiterpene lactones, flavonoids and polyacetylenes[14-20].Anethimsmelampodina is anannual, greyish- tomentose, herb with ascending branches from near the base. The flowers are white-yellow in color.This plant is known to grow widely in northern region of Saudi Arabia including Hail[21].

In a continuation of an extensive work aimed at the investigation of the volatile constituents of aromatic plants from Saudi Arabia, the current investigation was designed to investigate the chemical composition of the essential oil A. melampodina obtained by two different extraction methods, the Solid Phase Micro-Extraction and hydro-distillation methods and compare the current findings with those obtained from other locations of the world.

Experimental

Plant Material

Aerial parts of A. melampodina were collected during the full flowering stage March 2012) from Hart Alrha – south Tabuk. The identity of the plant species was confirmed by Dr Jacob Thomas from the Herbarium Division, College of Science, King Saud University, Riyadh, KSA. A voucher specimen Anthps-PNU-013was kept in the Chemistry Department, College of Science, Princess NouraBint Abdel Rhman University, Riyadh, Saudi. The plant material was dried at room temperature until constant weight was obtained.

Hydro-distillation of plant material

Air dried flowering parts (150 g) were coarsely powdered and then hydro-distilled using a Clevenger apparatus for 3 h. The extraction was repeated twice and the obtained oils were pooled separately, dried over anhydrous sodium sulfate (Na2SO4) and stored at 4ºC in amber glass vials until analysis.

Solid Phase Micro Extraction of the volatile oils (SPME)

The Solid Phase Micro Extraction experiments were performed using SPME fiber assembly (Polydimethylsilocane/Divenylbenzene, PDMS/DVB; df 65 mm partially crossed-linked phase, fiber length 1 cm) and assemblies for manual sampling (Supelco, Bellefonte, PA, USA). Before measurements, the fiber was conditioned according to the producer’s recommendations. About 0.1 mg of freshly powdered flowers was introduced into 4.0 mL amber glass vials, tightly capped with PTFE-coated septa, and SPME extraction was performed for 2.0 min at room temperature. Desorption of the analytes was carried out at 240ºC for 60 s. Each sample was repeated twice.

GC-MS and GC-FID analysis

About 1 μl aliquot of each oil sample, diluted to 5 μl in GC grade n-hexane, was subjected to GC/MS analysis. The GC/MS analysis was performed using Varian Chrompack CP-3800 GC/MS/MS-200 (Saturn, Netherlands) equipped with DP-5 (5% diphenyl, 95% dimethyl polysiloxane) GC capillary column (30 m × 0.25 mm i.d., 0.25 μm film thicknesses), with helium as a carrier gas (flow rate 0.9 mL/min). The actual temperature in MS source was 180ºC and the ionization voltage was 70 eV. The column temperature was kept at 60ºC for 1 min (isothermal), and programmed to 246ºC at a rate of 3ºC/min, and kept constant at 246ºC for 3 minutes (isothermal). A hydrocarbon mixture of n-alkanes (C8-C20) was analyzed separately by GC/MS under the same chromatographic conditions using the same DP-5 column.

For the quantitative analysis (% area), a Hewlett-Packard HP-8590 gas chromatograph equipped with a split-splitless injector (split ratio 1:50) and an FID detector was used. The column was an optima-5 (5% diphenyl, 95% dimethyl polysiloxan) fused silica capillary column (30 m × 0.25 mm, 0.25 film thickness). The temperature of the oven was increased at a rate of 10ºC/min from 60ºC to 250ºC and then held constant at 250ºC for 5 min. The temperatures of the injector and detector were maintained at 250ºC and 300ºC, respectively. The relative peak areas of the oil components were measured and then used to calculate the concentration of the detected compounds. Each sample was analyzed twice.

Identification of the components

The components of the essential oils obtained from the SPME and hydro-distilled flowering parts of the plant were identified using the built in libraries (Nist Co and Wiley Co, USA) and by comparing their calculated retention indices relative to (C8-C20) n-alkanes literature values measured with columns of identical polarity (Adams, 2001), or with authentic samples. The compounds, α– and β-pinenes, p-cymene, limonene, linalool (Fluka, Buchs, Switzerland) and sabinene hydrate (Sigma-Aldrich, Buchs, Switzerland) were used as reference substances in GC/MS analysis. GC-grade hexane and analytical reagent grade anhydrous Na2SO4 were purchased from Scharlau (Barcelona, Spain) and UCB (Bruxelles, Belgium).

Results

The GC/MS analysis of the volatile potentials and hydrodistilled oil obtained from flowering parts of A. melampodinaled to the characterization of total of 76 different components(Table 1).In the SPME method, 47 components amounting to 98.25 % of the total oil content were identified. Monoterpene hydrocarbons(88.89%)were the main contributors to the SPME volatiles and were dominated by b-pinene (35.29%), trans-ocinene (23.29%), terpinolene (15.7%), g-terpinene (6.84%) and cis-ocimene (5.23%). Oxygenated monoterpenes accounted for 4.95% of the total oil content with tetrahydrolavanduledetected as a major components (0.94%).Sesquiterpene hydrocarbons were detected at much lower concentrations (2.51%) and the main contributors included b-sesquiphellandrene (1.23%) and guaiene (0.58%). In addition, oxygenated sesquiterpenes and aromatics compounds where detected in very low concentrations as compared to other classes (0.76% &0.74%., respectively).

GC/MS analysis of the hydro-distilled oil obtained from the flowering aerial parts of A. melampodina resulted in the identification of a  total of 45 components which amounted to  97.86 % of the total oil content (Table 1). Careful analysis of the GC/MS spectrum revealed marked qualitative and quantitative differences in the chemical composition between the SPME and the hydro-distilled essential oil (Figures 1&2). The hydro-distilled oil was dominated by oxygenated sesquiterpenes that accounted for 31.22 % of the total oil content. This fraction was dominated by intermedeol (11.69%), methyl-2-epilasmona (4.19%), Z-a-santalol acetate (2.11%) and eudesmo-7(11)-en-4-o (2.11%). Monoterpene hydrocarbon accounted for (29.97%). This fraction was represented bya-pinene (15.33%) followed by myrecen (5.70%) and limonene (3.18). Oxygenated monoterpenesamounted to 20.72%andborneol (7.31%) was detected as the main compound of this fraction. The hydro-distelledoil contained sesquiterpene hydrocarbons(7.28%) with b-selinene(2.06%) ,trans-b-farnesene(1.60%),trans-caryophyllene(1.59%), germacrene D(1.26%)  being detected as the main contributors to this fraction. Diterpene hydrocarbon amounted to 6.39% of the total oil content and were represented bypimaradiene(3.63%),dolabradiene (2.02%).The hydro-distilled oil contained also aliphatic hydrocarbons and their derivative (1.26 %) and aromatic compounds (1.01%). The findings of the current investigation clearly indicated that the chemical composition of A.melampodina varies with the extraction method employed.[22].

Previous studies on the essential oil of A. melampodinacollected in Egypt(1989) revealed to the  isolation of Sesquiterpene lactones ,Sterols,flavonoid[22]. Again in Egypt (2002 ) The essential oil of  the A. melampodina was characterized by the presence of a high percentage of monoterpene hydrocarbons (49.94%) while asesquiterpene hydrocarbons and oxygenated sesquiterpenesreported only the yield (0.03%) 7.41% and 11.43% of the oil while .In addition the essential oil  of A. Melampodina was showed moderate larvacidal activity (LC(50) 139.42 ppm against culexpipens [23]. Hence, the objective of the present study was undertaken to identify the chemical composition oil of Anthemismelampodina. plant collected from Tabouk.

Table 1

No

Lit RI

exp RI

Compound

% SPME

composition

% Distillation

composition

1

915

926

amyl acetate

0.35

2

939

935

a-pinene

15.33

3

954

953

camphene

0.33

4

975

975

sabinene

0.86

5

979

981/987

b-pinene

35.29

2.15

6

991

990

myrecene

5.70

7

1003

1010

a-phellandrene

2.09

8

1009

1015

hexyl acetate

0.03

9

1025

1027

p-cymene

0.56

10

1029

1032/1027

limonene

1.78

3.18

11

1037

1032?

cis-ocimene

5.23

12

1031

1035

1,8-cineol

6.87

13

1050

1045

trans-ocimene

23.96

14

1060

1062

g-terpinene

6.84

15

1070

1074

cis-sabinene hydrate

0.33

16

1082

1082

p-tolualdehyde

0.64

17

1089

1088

terpinolene

15.78

18

1094

a-campholenal

0.32

19

1121

1105?

endo-fenchol

0.15

20

1103

1105

isoamylisovalerate

0.48

21

1121

1118

sabina ketone

0.15

22

1134

1131

1-terpineol

0.05

23

1144

1145

cis-b-terpineol

0.08

24

1145

1151

trans-verbenol

0.10

0.76

25

1162

1162

tetrahydrolavandule

0.94

26

1170

1168

pinocampheol

0.30

27

1175

1173

isopinocamphone

0.22

28

1169

1177

borneol

0.10

7.31

29

1180

1182

isopinocampheol

1.46

30

1189

1190

a-terpineol

0.16

31

1196

1200

myrtenol

0.10

0.50

32

1229

1227

Z-ocimenone

0.07

33

1230

1232

nerol

2.35

34

1245

1237

2Z-hexenyl isovalerate

0.79

35

1239

1238

isoborneolformate

0.42

36

1249

1242

perilla ketone

0.22

37

1253

1251

pipertinoe

0.09

38

1264

1259

2E-deceneal

0.03

39

1272

1284/1286

perilla aldehyde

0.16

0.34

40

1298

1296

geranylformate

1.65

41

1354

1350

2-phenylethyl propanoate

0.11

42

1393

1399

Z-jasmone

0.81

43

1419

1423

trans-caryophyllene

1.59

44

1457

1455

trans-b-farnesene

1.60

45

1432

1447

b-copene

0.06

46

1457

1454

a- patchoulene

0.07

47

1460

1461

all-aromadendrene

0.14

48

1485

1485

germacrene D

1.26

49

1493

1493

guaiene

0.58

50

1490

1492

b-selinene

2.06

51

1500

1500

bicyclogermacrene

0.44

52

1514

1517

g-cadinene

0.33

53

1523

1527

b-sesquiphellandrene

1.23

54

1531

1531

trans-g-bisabolene

0.04

55

1536

1535

sliphiperfol-5-en-3-ol B

0.07

56

1550

1554

elemol

1.05

57

1561

1558

germacrene D

0.31

58

1569

1566

longipinanol

0.42

59

1585

1573

globulol

0.22

60

1567

1578

3Z-hexenyl benzoate

0.45

61

1578

1582

spathulenol

2.51

62

1583

1587

caryophyllene oxide

0.86

63

1601

1591

guaiol

0.06

64

1596

carotol

0.06

65

1637

1634

gossonorol

1.11

66

1632

1638

g-eudesmol

1.79

67

1640

1648

tau-cadinol

3.00

68

1667

1662

intermedeol

11.69

69

1679

1681

methyl-z-epijasmonate

4.19

70

1685

1689

5-neocedranol

0.58

71

1700

1692

eudesm-7(11)-en-4-ol

1.03

72

1779

1175

Z-a-santalol acetate

2.11

73

1807

1818

nootkatone

1.30

74

1906

1909

isopimara-9(11),15-diene

0.74

75

1950

1951

pimaradiene

3.63

76

1696

1958

dolabradiene

2.02

monoterpene hydrocarbons

88.89

29.97

oxygenated monoterpenes

4.94

20.72

sesquiterpene hydrocarbons

2.51

7.28

oxygenated sesquiterpenes

0.76

31.22

diterpene hydrocarbons

0.00

6.39

aromatics

0.74

1.01

aliphatic hydrocarbons and their derivatives

0.40

1.267

total

98.25

97.86

 

Figure 1: Variation in the % composition of the essential oil of A. melampodinafrom Saudi origin obtained by SPME method. Figure 1: Variation in the % composition of the essential oil of A. melampodinafrom Saudi origin obtained by SPME method. 

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 Figure 2: Variation in the % composition of the essential oil of A. melampodinafrom Saudi origin obtained by hydro-distillation extraction method. Figure 2: Variation in the % composition of the essential oil of A. melampodinafrom Saudi origin obtained by hydro-distillation extraction method. 

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