Volatile Constituents of Matricaria chamomilla

Document Type: Research Paper

Authors

1 Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

2 Department of Pharmacognosy, Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran

Abstract

      The volatile oil obtained by hydrodistillation of the aerial parts of Matricaria chamomilla L. (Asteraceae) growing in Botanical Garden, Isfahan University of Medical Sciences, Iran, was investigated by gas chromatography (GC) and GC/ mass spectrometery (MS). Sixty-three components were characterized, representing 86.21% of the total oil components detected. α-Bisabolol oxide A (25.01%) and a-bisabolol oxide B (9.43%) were the major constituents of the oil.  

Keywords


1. Introduction

 

     Chamomile, Matricaria chamomilla L. Asteraceae family, is a well-known and important medicinal plant in Iran that traditionally have been used for the treatment of various diseases, and it is cultivated all over the world [1, 2]. The medicinal and phar-macological effects of chamomile are mainly connected with its essential oil for its antispasmodic, antimicrobial and disinfective properties [2-4]. Chamomile essential oil is widely used in food, cosmetics and pharmaceutical industries. The largest group of medically important compounds forming the essential oil are α-bisabolol, bisabolol oxides, chamazulene and en-yn-dicycloethers. Flavonoids, coumarins, hydroxycinnamic acids, mucilages and some other primary metabolites also have pharmacological effects [2-5].

 

     Different essential oil isolation techniques and analysis methods have been applied for studying the volatile constituents of chamomile by several groups [2, 3, 5, 6]. The purpose of this work was to determine the composition of volatile essential oil from a chamomile sample cultivated in Botanical Garden of School of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran, to identify and compare the composition of this oil with those of foreign origins.

 

2. Materials and methods

 

2.1. Plant material

     Flowers of cultivated M. chamomilla were collected from Botanical Garden of faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran in June 2000. The plant identity as Matricaria chamomilla L. was confirmed by the Herbarium Department of School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. A voucher specimen of the plant was deposited in the herbarium. The air-dried flowers of the plant were powdered and the volatile fraction was isolated by hydrodistillation for 3 h according to the method recommended in British Pharmacopoeia [7]. The oil was dried over anhydrous sodium sulfate and stored in a refrigeratore (4 °C).

 

 

 

Table 1: Composition of essential oil of Matricaria chamomilla L. flowers.

 

 

 

 

Compounds

Percentage

Retention Index

Propyl butyrate

0.10

927

α-Pinene

0.03

952

Camphene

0.02

958

Butyl butyrate

0.10

993

Yomogi alcohol

0.20

1001

para-Cymene

0.18

1020

Artemisia ketone

0.40

1047

n-Octanol

0.08

1053

Artemisia alcohol

0.16

1062

Linalool

0.04

1072

n-Nonanal

0.08

1075

Camphor

0.04

1099

cis-Chrysanthenol

0.06

1114

Borneol

0.28

1117

n-Nonanol

0.07

1112

4-Terpineol

0.05

1113

para-Cymene-8-ol

0.11

1133

3-Decanol

0.16

1138

Ethyl octanoate

0.21

1143

n-Decanal

0.06

1148

n-Hexyl 2-methyl butyrate

0.02

1167

Hexyl 3-methyl butanoate

0.32

1170

Nonanoic acid

0.22

1201

trans-Anethol

0.38

1207

Azulene

0.12

1218

trans, trans-2,4-Decadienal

0.11

1227

Methyl decanoate

0.11

1233

δ-Elemene

0.07

1240

Daucene

0.09

1251

3-Dodecanone

0.03

1259

β-Elemene

0.13

1268

trans-β-Damascone

0.22

1275

β-Caryophyllene

0.26

1279

γ-Elemene

0.61

1282

cis-β-farnesene

0.31

1321

trans-β-farnesene

4.68

1331

α-Terpinyl isobutyrate

0.24

1337

Germacrene-D

0.48

1344

β-Selinene

0.37

1347

α-Muurolene

0.50

1355

cis-α-Bisabolene

0.18

1360

β-Bisabolene

0.15

1364

γ-Cadinene

0.29

1366

δ-Cadinene

0.15

1372

trans-γ-Bisabolene

0.16

1376

α-Cadinene

0.14

1386

Spathulenol

8.49

1419

Caryophyllene oxide

0.40

1429

n-Hexadecane

0.52

1435

γ-Eudesmol

1.98

1462

α-Bisabolol oxide B

9.43

1476

β-Bisabolol

0.62

1482

α-Bisabolene oxide A

7.17

1493

α-Bisabolol

6.01

1499

Chamazulene

3.28

1524

α -Bisabolol oxide A

25.01

1557

β-Bisabolenal

0.28

1578

α -Bisabolol acetate

0.48

1602

n-Octadecane

0.38

1611

cis-en-yn-Dicycloether

7.42

1659

trans-en-yn-Dicycloether

1.82

1674

Ethyl hexadecanoate

0.12

1757

7-hydroxy-4-methyl Coumarin

0.03

1782

Identification (%)

 

86.21

Grouped components

 

 

Monoterpene hydrocarbons

 

0.35

Oxygen-containing monoterpenes

 

1.72

Sesquiterpene hydrocarbons

 

11.85

Oxygen-containing sesquiterpenes

 

60.33

Others

 

11.96

 




















































2.2. Analysis

 

      The oil was analyzed by gas chromatography (GC) and GC/ mass spectrometery (MS). GC analysis was carried out on a Perkin-Elmer gas chromatograph Model 8500, equipped with a FID detector and a BP-1 capillary column (30 m×0.25 mm, film thickness 0.25 mm). The operating conditions were as follows: carrier gas, helium with a flow rate of 2 ml/min.; column temperature, 60-275 ºC at 4 ºC/min.; injector and detector temperatures, 275 and 280 ºC, respectively; volume injected, 0.1 ml of the oil; split ratio, 1:25.

 

      GC/MS analysis was performed on 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 mm) and operating under the same conditions as described above. The MS operating parameters were as follows: ionization potential, 70 eV; ionization current, 1 A; ion source temperature, 200ºC; resolution, 1000.

 

     Identification of components in the oil was based on GC 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 [8-10]. The relative percentage of the oil constituents was calculated from the GC peaks.

 

3. Results and discussion

 

      Flowers of M. chamomilla yielded a blue essential oil with a fresh pleasant odour. Sixty-three components were characterized, representing 86.21% of the total oil components detected. These are listed in Table 1 with their percentage composition. The oil was rich in sesquiterpenoids. Many of the unidentified compounds were present in trace amounts. The major constituents of the oil were α-bisabolol oxide A (25.01%), α-bisabolol oxide B (9.43%), spathulenol (8.49%), cis-en-yn-dicycloether (7.42%) and α-bisabolene oxide A (7.17%). Other components were present in amounts less than 7%. M. chamomilla produces a volatile oil which is different from those known chamomile oils [2-6, 11]. This oil is a valuable source of α-bisabolol oxides A and B.

 

Acknowledgments

 

      We are grateful to Mrs. A. Jamshidi (Department of Pharmacognosy, Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran) for her technical assistance in the course of practical works.

 

 

[1]      Mozaffarian V. A dictionary of Iranian plant names. Tehran: Farhang Mo’aser, 1996; p. 340.

 

[2]      Omidbaigi R. Production and processing of medicinal plants. Vol. 1. Mashad: Astane Ghodse Razavi Publications, 2000; pp. 249-65.

 

[3]      Newall CA, Anderson LA, Phillipson JD. Herbal medicines: a guide for health-care professionals.

 London: The Pharmaceutical Press, 1996; pp. 69-71.

 

[4]      Duke JA. CRC  handbook  of  medicinal  herbs. Boca Raton: CRC Press, 1989; pp. 297-8.

 

[5]       Papazoglou V, Anastassaki T, Demetzos C, Loukis A. Composition of the essential oils of wild

Chamomilla  recutita  (L.)  Rausch.  grown  in Greece. J Essenl Oil Res 1998; 10: 635-6.

 

[6]      Carle R, Dolle B, Reinhard E. A new approach to the production of chamomile extracts. Planta Med 1989; 55: 540-3.

 

[7]      British Pharmacopoeia. Vol. 2. London: HMSO, 1998; A137-8.

[8]      Mclafferty FW, Stauffer DB. The important peak index of the registry of mass spectral data. Vol. 1. New York: John Wiley & Sons, 1991.

 

[9]      Sandra P, Bicchi C. Capillary gas chromatography in essential oil analysis. Heidelberg: Dr. A.

Huethig, 1987; pp. 259-74, 287-328.

 

[10]  Swigar AA, Silverstein RM. Monoterpenes: infrared, mass, proton-NMR, carbon-NMR spectra and kovats indices. Wisconsin: Aldrich Chemical Company Inc., 1981; 3-121.

 

[11]  Maday E, Szoke E, Muskath Z, Lemberkovics E. A study of the production of essential oils in chamomile hairy root cultures. Eur J Drug Metabol Pharmacokin 1999; 24: 301-8.