Chemical Constituents of the Essential Oil of Stachys lavandulifolia Vahl from Iran

Authors

Abstract

The essential oil of Stachys lavandulifolia Vahl (Lamiaceae) was isolated by hydrodistillation of the aerial parts of the plant, with a yield of 0.25%. The chemical composition of volatile oil was analyzed by capillary GC and GC/ MS. The main components were germacrene-D (13.2%), ?-phellandrene (12.7%), ?-pinene (10.2%), myrcene (9.4%), ?-pinene (8.4%) and Z-?-ocimene (5.8%).

Keywords


Chemical Constituents of the Essential Oil of Stachys lavandulifolia Vahl from Iran

Iranian Journal of Pharmaceutical Research (2004) 3: 61-63
Received: October 2003
Accepted: December 2003

Short Communication

Chemical Constituents of the Essential Oil of Stachys lavandulifolia Vahl from Iran

 Katayoun Javidnia*a, Faraz Mojabb, Seyed Ali Mojahedic

 

aDepartment of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. bPharmaceutical Sciences Research Center, Shaheed Beheshti University of Medical Sciences, Tehran, Iran. cIranian Academic Centre for education, culture and research, Shaheed Beheshti University, Tehran, Iran

 

* Corresponding author: javidniak@sums.ac.ir

 

Abstract

 

The essential oil of Stachys lavandulifolia Vahl (Lamiaceae) was isolated by hydrodistillation of the aerial parts of the plant, with a yield of 0.25%. The chemical composition of volatile oil was analyzed by capillary GC and GC/ MS. The main components were germacrene-D (13.2%), β-phellandrene (12.7%), β-pinene (10.2%), myrcene (9.4%), α-pinene (8.4%) and Z-β-ocimene (5.8%).

 

Keywords: Stachys lavandulifolia; Lamiaceae; essential oil; GC-MS.

 

 

? Introduction

 

In the flora of Iranica genus, Stachys is represented by thirthy-one species. Stachys lavandulifolia is grown in many parts of Iran, Iraq and Anatolia (1). The plant is known as Chaye-kuhi in Iran and its? english name is Betony. It is used as the herbal tea in gastrointestinal disorders (2). Hydroalcoholic extract of the aerial parts of S. inflata shows potent anti-inflammatory activity in rat. The methanolic extract of the tuber of S. sieboldii has anti-anoxia action in mice (3, 4). Ramezani et al. reported spathulenol and caryophyllene oxide as the main constituents of S. lavandulifolia (5). In the present study a sample of S. lavandulifolia with different chemical composition has been reported.

 

Experimental

Plant Material and Isolation Procedure

The plant material was collected in May 2002 from the Fasham area near Tehran.? A voucher specimen has been deposited in the Herbarium of the Faculty of Pharmacy, Shaheed Beheshti University of Medical Sciences (herbarium no. 0783). The aerial parts of the plant were air-dried. The oil was obtained by hydrodistillation using a Clevenger-type apparatus for 4 hours. The yield of oil was 0.25%.

 

Identification of the oil components

The analytical Gas Chromatography (GC) method was carried out using a Varian GC 3600 chromatograph with DB-5 (methyl phenyl siloxane 25 m X 0.25 mm, 0.25 μm film thickness), N2 as the carrier gas with a split ratio of 1:20, and a flame ionization detector. Temperature programming was performed from 60?-240?C at 3?/min, with injector and detector temperatures, 240?C and 260?C respectively. GC/ MS was performed on a cross-linked 5% phenyl methyl siloxane (HP-5, 30 m X 0.25 mm, 0.25 μm film thickness) with He as the carrier gas ata split ratio of 1:20 and quadropole mass spectrometer (Helwett- Packard 6890) operating at 70 eV ionization energy. EIMS spectra were obtained in the scan mode at m/e range of 35-400 amu. The chromatographic conditions were as above. Retention indices were determined by using retention times of n-alkanes, which has been injected after the oil, under the same chromatographic conditions. The retention indices for all the components were determined according to the Van Den Dool method using n-alkanes as standard (6). The constituents were identified by comparison of retention indices (RRI, HP-5) with those reported in the literature and by comparison of their mass spectra with those held in Wiley library of mass spectra or with the published mass spectra (7,8).

 

Results and Discussion

 

The yield of the oil obtained from S. lavandulifoila was 0.25%. The yield of the oils extracted from other species were, 0.18% from S. setifera ssp. iranica 0.18% from S. chrysantha, and 0.12% from S.candida (9, 10). The S. lavandulifolia oil was examined by GC and GC-MS. The list of compounds identified in the oil of S. lavandulifolia can be seen in Table 1.? Seventy-nine compounds were identified, representing 98.2% of the essential oil, in which the major components were germacrene-D (13.2%), β-phellandrene (12.7%), β-pinene (10.2%) myrcene (9.4%), α-pinene (8.4%) and Z-β-ocimene (5.8%). In a previous study the main components of the oil were reported to be spathulenol (35.0%) and caryophyllene oxide (25.6%), this finding was completely different from our study, in which only 1.5% spathulenol was present in the oil. The major component of the S. obliqua oil was germacrene-D, which was also the main component of the S. lavandulifolia oil (11). The main components of the oils of S. aegiptica (α-pinene) and S. glutinosa (α-pinene and β-phellandrene) were presented as the major components of the S. lavandulifolia oil (12,13). β-Pinene, one of the main components of S. recta and S. balansae oils, was present at an amount of 8.4% in S. lavandulifolia oil (14).

 

Table 1. Composition of the essential oil of Stachys lavandulifolia.

Peak no.

Compound name

RI

% in oil

1

Hexanal

800

t

2

E-2-Hexenal

850

0.1

3

Heptanal

900

t

4

α-Thujene

928

0.5

5

α-Pinene

937

8.4

6

Camphene

949

0.3

7

Sabinene

974

0.3

8

β-Pinene

982

10.2

9

Myrcene

995

9.4

10

α-Phellandrene

1006

t

11

δ-3-Carene

1011

0.2

12

α-Terpinene

1017

0.5

13

β-Phellandrene

1033

12.7

14

Z-β-Ocimene

1043

5.8

15

E-β-Ocimene

1050

0.9

16

γ-Terpinene

1061

1.4

17

Z-Sabinene-hydrate

1068

0.2

18

Terpinolene

1088

0.3

19

Linalool

1101

0.5

20

Nonanal

1104

0.1

21

p-menth-2-en-1-ol

1120

0.1

22

α-Campholene aldehyde

1125

0.1

23

allo-ocimene

1128

0.2

24

E-Pinocarveol

1137

0.2

25

E-verbenol

1143

0.1

26

pinocarvone

1160

0.1

27

borneol

1165

t

28

terpinen-4-ol

1177

0.3

29

α-Terpineol

1190

0.3

30

methyl salicylate

1192

t

31

32

myrtenal

+ myrtenol

1195

0.2

33

β-cyclocitral

1218

t

34

nerol

1226

t

35

cuminal

1237

0.1

36

geraniol

1254

0.1

37

bornyl acetate

1283

t

38

E-anethole

1285

0.6

39

p-cymen-7-ol

1290

t

40

δ-elemene

1337

0.1

41

α-cubebene

1348

0.1

42

eugenol

1357

0.1

43

cyclosativene

1365

0.2

44

α-copaene

1378

4.4

45

β -bourbonene

1382

0.5

46

β-elemene

1391

1.3

47

Z-jasmone

1394

t

48

α-gurjunene

1406

0.2

49

β-caryophyllene

1415

t

50

E-α-bergamotene

1433

0.7

51

Z-β-Farnesene

1441

0.8

52

α-humulene

1450

0.2

53

E-β-Farnesene

1458

3.4

54

germacrene-D

1480

13.2

55

bicyclogermacrene

1498

4.0

56

β-bisabolene

1508

0.8

57

γ-cadinene

1513

0.5

58

δ-cadinene

1526

3.1

59

cadina-1,4-diene

1531

0.1

60

α-cadinene

1536

0.1

61

β-calacorene

1560

0.1

62

Spathulenol

1577

1.8

63

globulol

1583

0.2

64

T-cadinol

1642

1.0

65

α-muurolol

1647

0.3

66

valeranone

1672

0.5

67

α-bisabolol

1685

0.9

68

heptadecane

1697

0.1

69

benzyl benzoate

1763

0.2

70

methyl hexadecanoate

1924

t

71

palmitic acid

1975

0.3

72

trans-phytol

2116

3.1

73

octadecanoic acid

2178

0.1

74

docosane

2197

0.1

75

tricosane

2298

0.2

76

tetracosane

2399

t

77

hexacosane

2595

0.1

78

heptacosane

2696

t

79

octacosane

2795

0.8

monoterpenes

sesquiterpenes

 

 

54.0%

38.6%

t=trace (<0.05%)

 

?References

 

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