Quantity and Composition of the SDE Prepared Essential Oil of Nepeta macrosiphon Boiss

Authors

Abstract

The essential oil from flowering aerial parts of Nepeta macrosiphon Boiss. growing wild in Kermanshah Province, Iran, was analyzed by GC/MS. This essential oil was prepared by a modified Likens-Nickerson’s simultaneous distillation-extraction (SDE) method. Forty-five compounds consisting 95.1% of the total components were identified from the oil obtained with a yield of 0.1%w/w. Among them, spathulenol (14.1%), germacrene D (9.2%) and caryophyllene oxide (8.1%) were the major components of the oil.

Keywords


Compositional analysis of the essential oil of Lallemantia royleana (Benth

Iranian Journal of Pharmaceutical Research (2003) 103-105
Received:  September 2002
Accepted: May 2003

 

Original Article

Quantity and Composition of the SDE Prepared Essential Oil of Nepeta macrosiphon Boiss

Alireza Ghannadi*a, Fatemeh Aghazaria, Mitra Mehrabania, Abdolali Mohagheghzadeh b, Iraj Mehreganb.

aDepartment of Pharmacognosy, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences and Health services, Isfahan, Iran. bDepartment of Pharmacognosy, School of Pharmacy, Shiraz University of Medical Sciences and Health services, Shiraz , Iran.

* Corresponding authorE-mail: ghannadi@pharm.mui.ac.ir

Abstract

The essential oil from flowering aerial parts of Nepeta macrosiphon Boiss. growing wild in Kermanshah Province, Iran, was analyzed by GC/MS. This essential oil was prepared by a modified Likens-Nickerson?s simultaneous distillation-extraction (SDE) method. Forty-five compounds consisting 95.1% of the total components were identified from the oil obtained with a yield of 0.1%w/w. Among them, spathulenol (14.1%), germacrene D (9.2%) and caryophyllene oxide (8.1%) were the major components of the oil.

Keywords: Nepeta macrosiphon; Lamiaceae; Essential oil composition; GC/MS; Spathulenol; Germacrene D; Caryophyllene oxide.

Introduction

The genus Nepeta, also called Glecho ma and Cataria, is named after the ancient Italian city of Nepi (1). This genus which belongs to Stachyoideae-Nepeteae tribe, Lamiaceae family, consists of about 250 species distributed in the central and southern parts of Europe, Asia and Middle East (2, 3). Many reports on phytochemical analysis of this genus, including essential oil analysis, are found in the literature (4-27). Most oils of Nepeta species contain nepetalactones as the main components, but some differences in the essential oil composition were detected in several Nepeta oils (15-27). Antibacterial, fungicidal, antiviral and opioid analgesic activities have been attributed to nepetalactones (19, 21). Nepeta species are still used in the traditional medicine of many countries as diuretic, diaphoretic, vulnerary, antitussive, antispasmodic, anti-asthmatic, tonic, febrifuge, emmenagogue and sedative agents (22, 27, 28). Some of Iranian Nepeta species has been of great interest to Iranian folk and traditional medicines and used in the treatment of various disorders, such as some nervous, respiratory and gastrointestinal diseases (27, 29).

The Iranian flora comprises 67 species of Nepeta and one of them is Nepeta macrosiphon Boiss (2, 30). This herb distributed in different rocky western areas of Iran (2). The Persian names of the plant are "punesaye sisakhti" and "punesaye lulehboland" (30). Our literature surveys revealed that the essential oil of the aerial parts of N. macrosiphon has not been chemically studied to date, therefore this article deals with the detailed quantity and composition of the SDE oil prepared by GC/MS.

Experimental

Plant Material

The aerial parts of wild-growing N. macrosiphon were collected during the flowering period from northern slopes of Dalakhani mountain, Songhur (Kermanshah Province, Iran) at an altitude of ca. 2300 m in June 2001. The plant identity as N. macrosiphon was confirmed by the Herbarium Department of the Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. A voucher specimen of the plant was deposited in the Herbarium of the Department of Pharmacognosy, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran.

Table 1. Components present within the oil obtained from the aerial parts of Nepeta macrosiphon.

No.

Compound

%

RI

1

trans-2-hexenal

trace

850

2

alpha-pinene

0.3

936

3

camphene

0.1

951

4

beta-pinene

0.1

978

5

1,8-cineole

0.2

1030

6

trans-beta-ocimene

0.3

1048

7

gamma-terpinene

1.0

1058

8

cis-sabinene hydrate

0.1

1065

9

linalool oxide B

0.1

1071

10

linalool oxide A

0.4

1086

11

alpha-pinene oxide

0.3

1094

12

linalool

4.1

1097

13

trans-pinocarveol

0.4

1137

14

trans-verbenol

1.0

1142

15

borneol

0.2

1165

16

terpinene-4-ol

0.5

1176

17

myrtenol

2.0

1194

18

verbenone

4.4

1204

19

geraniol

0.5

1253

20

bornyl acetate

1.1

1283

21

citronellyl acetate

3.8

1350

22

alpha-copaene

0.4

1375

23

beta-bourbonene

1.3

1384

24

longifolene

1.0

1401

25

aromadendrene

4.8

1438

26

germacrene D

9.2

1481

27

bicyclogermacrene

5.7

1495

28

alpha-muurolene

6.0

1497

29

germacrene A

2.4

1501

30

gamma-cadinene

1.0

1512

31

delta-cadinene

2.3

1523

32

alpha-cadinene

3.0

1538

33

spathulenol

14.1

1580

34

caryophyllene oxide

8.1

1581

35

gamma-eudesmol

3.9

1633

36

torreyol

2.0

1642

37

alpha-cadinol

4.9

1657

38

cadalene

0.4

1679

39

caryophyllene acetate

0.4

1705

40

khusimol

0.2

1740

41

gamma-eudesmol acetate

1.0

1782

42

n-octadecane

0.5

1804

43

pentadecanoic acid

0.3

1869

44

`n-nonadecane

0.2

1907

45

methyl octadecanoate

1.1

2139

The air-dried aerial parts of the plant were powdered and the volatile fraction was prepared by a modified Likens-Nickerson?s simultaneous distillation and extraction (SDE) method (31, 32). A microscale simultaneous distillation extraction apparatus (Ashke Shishe, Tehran, Iran) was used. Dried powdered plant was homogenized with distilled water and the homogenate subjected to SDE apparatus for 3 h using pentane (chromatography grade reagent, Merck) as solvent and then extract was concentrated with nitrogen.

GC/MS Analysis

The oil was analyzed by GC/MS using a Hewlett Packard 6890 mass selective detector coupled with a Hewlett Packard 6890 gas chromatograph, equipped with a cross-linked 5% PH ME siloxane HP-5MS capillary column (30 m ? 0.25 mm, film thickness 0.25 μm). Operating conditions were as follows: carrier gas, helium with a flow rate of 2 ml/min; column temperature, 60-275?C at 4?C/min; injector and detector temperatures, 280?C; volume injected, 0.1 μl of the oil; split ratio, 1:50.

The MS operating parameters were as follows: ionization potential, 70 ev; ionization current, 2 A; ion source temperature, 200?C; resolution, 1000.

Identification of components in the oil was based on retention indices relative to n-alkanes and computer matching with the WILEY 275.L library, as well as by comparison of the fragmentation patterns of the mass spectra with those reported in the literature (33-36).

Results and Discussion

Aerial parts of N. macrosiphon yielded 0.1% (w/w vs dried material) of a pale yellowish oil with a strong pleasant aroma. Forty-five components were characterized, representing 95.1% of the total oil compounds detected. These are listed in Table 1 with their percentage composition. The major constituents of the sesquiterpene-rich oil of N. macrosiphon were spathulenol (14.1%), germacrene D (9.2%), caryophyllene oxide (8.1%), alpha-muurolene (6.0%) and bicyclogermacrene (5.7%). Other components were present in amounts less than 5%. Many of the unidentified compounds were present in trace amounts.

Although the presence of nepetalactones in several Nepeta species in relatively high concentrations has been reported (15-27), no nepetalactones were found in this oil. The predominance of spathulenol and caryophyllene oxide has been found in essential oils of two Turkish Nepeta species (9, 12). These compounds and germacrene D are typical in most Nepeta species (4-27).

Acknowledgments

This work was supported by Research Council of the Isfahan University of Medical Sciences, Isfahan, Iran (Research project No. 80256). We are grateful to Dr. Javad Asili (Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan , Iran) for his assistance in preparing the plant essential oil.

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