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Composition of the essential oil of Artemisia absinthium L. of different geographical origin/Erinevatest geograafilistest paikadest parit koirohu (Artemisia absinthium L.) eeterliku oli koostis.

INTRODUCTION

Artemisia absinthium L. (wormwood) is a perennial undershrub growing naturally in Europe, North America, and Asia. It is widely used in folk medicine. The volatile oil distilled from dried leaves and flowers is used in fragrance compounding and in some external analgesics [1-3]. The composition of the essential oil from A. absinthium has been the object of several studies [1-12], especially for its contents of such compounds as thujone isomers and chamazulene with pharmacodynamic properties. cis-Epoxyocimene and trans-sabinene hydrate were found in the oil of A. absinthium in high quantities by Chialva et al. [6, 7]. Several chemotypes were detected in these works: cis-epoxyocimene and [alpha]-thujone chemotypes (plants from Italy), chrysantenyl acetate and sabinyl acetate chemotypes (plants from France), and a mixed chemotype (plants from Italy, Siberia, and Romenia).

According to the European Pharmacopoeia [13], the crude drug of wormwood (Absinthii herba) consists of the basal leaves or slightly leaf, flowering tops, or of a mixture of these dried, whole or cut organs of A. absinthium. It contains not less than 2 mL/kg (-0.2%) of essential oil, calculated with reference to the dried drug. The essential oil (content 0.2-1.5%) varies considerably in composition [14].

An overdose of alcoholic preparations or essential oil may cause disturbances of the central nervous system, which can lead to convulsions and ultimately to unconsciousness and death. Thujone isomers are responsible for the hallucinogenic and toxic effect of wormwood oil and absinthe, and therefore thujones rich chemotypes of wormwood are not appreciated. They are neurotoxic, and the side effects include epileptic fits and long-lasting psychiatric disturbances. The use of essential oil and the content of thujone in foods and beverages are either strictly regulated or prohibited [14, 15]. The content of thujones in the essential oils of wormwood is up to 35% [16].

The essential oil of wormwood growing wild in Estonia has not been analysed by capillary gas chromatographic and gas chromatographic-mass spectrometric methods before. In this work a comparative study of the essential oil composition of wormwood samples obtained from retail pharmacies of Estonia and other European countries was carried out and the chemotypes of wormwood oil were determined.

EXPERIMENTAL

Materials

Plant materials (commercial Absinthii herba) were obtained from retail pharmacies of different European countries in 2000 (Estonia, France), 2001 (Hungary, Belgium, Estonia, Russia), 2002 (Estonia, Greece, Ukraine), 2003 (Scotland, Armenia, Moldova, Estonia), and 2004 (Estonia, Latvia, Lithuania, Italy, Spain, and Germany). Taxonomic identification of the plants was carried out in the Institute of Pharmacy of the University of Tartu.

Isolation of essential oil

Essential oil was isolated from dried wormwood herb by the distillation method described in the European Pharmacopoeia (EP) [13] using 50 g of cut drug, a 1000 mL round-bottomed flask, and 500 mL distilled water as the distillation liquid. Xylene (0.5 mL in a graduated tube) was added to take up the essential oil. The distillation time was 3 h at a rate of 2-3 ML/min.

Capillary gas chromatography

The essential oil extracts were analysed using a Chrom-5 chromatograph with FID on two fused silica capillary columns (50 m x 0.20 mm) with two stationary phases: nonpolar poly(dimethylsiloxane) (NB-30, Nordion, Finland) and polar poly(ethylene glycol) (NB-20M, Nordion, Finland). The film thickness of both stationary phases was 0.25 [micro]m. The carrier gas was helium with the split ratio of 1:150, and a flow rate of 20-25 cm/s was applied. The temperature program was from 50 to 250[degrees]C at 2[degrees]C/min, and the injector temperature was 200[degrees]C.

The identification of the oil components was accomplished by comparing their retention indices (RI) on two columns with the RI values of reference standards, our RI data bank, and literature data. The results obtained were confirmed by gas chromatography-mass spectrometry (GC-MS).

The percentage composition of the oils was calculated in peak areas (nonpolar column) applying a normalization method without using correction factors. The relative standard deviation of percentages of oil components of three repeated GC analyses of single oil did not exceed 5%.

GC-MS analysis

The MS analysis was carried out on a Hitachi M-80 B gas chromatograph double focusing mass spectrometer using an AT-5 poly(5%-phenyl-95% dimethylsiloxane) (30 m x 0.32 mm, film thickness 0.30 gm) fused silica capillary column from Alltech. The column temperature was at 70[degrees]C for 2 min and then 70-290[degrees]C at 2[degrees]C/min.

RESULTS AND DISCUSSION

The complex nature of the essential oil from common wormwood (Sample 4 from Estonia) is demonstrated in the chromatogram (Fig. 1). Retention indices (RI) on two columns, concentration range, mean %, standard deviation (SD), and variation coefficients of each component are presented in Table 1. In the wormwood oils studied 107 compounds were identified, representing more than 85% of the total oil. As it is seen from Table 1, considerable qualitative and quantitative differences exist between the wormwood samples from different geographical origins. Variation coefficients ranged from 0.5-0.7 ([alpha]-pinene, [alpha]-thujone, terpinen4-ol, [beta]-caryophyllene, neryl isobutanoate) to 4.4 (thymol, (E)-[alpha]-cadinol).

[FIGURE 1 OMITTED]

The main components, whose content in oils could be over 6%, were sabinene (0.9-30.1%), myrcene (0.1-38.9%), [alpha]-phellandrene (0-7.2%), p-cymene (0.2-9.6%), 1,8-cineole (0.1-18.0%), artemisia ketone (0-14.9%), linalool and [alpha]-thujone (1.1-10.9%), [beta]-thujone (0.1-64.6%), traps-epoxyocimene (0.1-59.7%), traps-verbenol (0-11.7%, carvone (0-18.5%), (E)-anethole (0-7.1%), (E)-sabinyl acetate (0-70.5%), thymol (0-10.2), carvacrol (0-9.7%), curcumene (0-7.0%), neryl butyrate (0.1-13.9%), neryl 2-methylbutanoate and spathylenol (0.1-9.2%), neryl 3-methylbutanoate (0.4-7.3%), [alpha]-bisabolol (0-7.5%), and chamazulene (0-6.6%). Some compounds with curcumene structure (Table 1), not earlier reported, were identified in wormwood samples studied using MS data.

The oil composition of five wormwood samples from Estonia was quite different. Monoterpenes (Fig. 2) predominated in samples 1 and 3. High amounts of sabinene and myrcene (21.2% and 25.6%) were characteristic of these samples (Table 2). Comparatively large contents of sabinene and myrcene (9.2-38.9%) were also found in the oils from wormwood growing in Hungary, Scotland, and Moldova (samples 7, 12, and 14). Sample 5 from Estonia was rich in (E)-sabinyl acetate (70.5%), in sample 2 from Estonia traps-epoxyocimene (59.7%) and (E)-sabinyl acetate (23.6%), and in sample 4 [beta]-thujone (64.6%) and (E)-sabinyl acetate (18.2%) predominated. (E)-Sabinyl acetate rich oil was characteristic of samples from Armenia (34.2%), Latvia (23.6%), Belgium (18.6%), and Lithuania (13.7%) too. In the samples from Greece, Spain, Ukraine, France, and Italy [alpha]- and [beta]-thujones were found as principal components (4.5-38.7%). A high content of epoxyocimenes (22.1%) was found in the sample from Russia.

[FIGURE 2 OMITTED]

Chialva et al. [7] studied 19 samples of A. absinthium from Italy, France, Romania, and Siberia (harvest year 1979-1981). They divided these samples into four chemotypes: sabinyl acetate rich oil, epoxyocimenes rich oil, chrysantenyl acetate rich oil, and thujones rich oil. The content of sabinene and myrcene in these samples was small (0.1-6.3%) (Table 2). The chrysantenyl acetate chemotype of A. absinthium was not found in the present work (harvest year 2000-2004); the content of chrysantenyl acetate in the studied wormwood oils was 0-1.8%. The sabinene and myrcene rich chemotype was detected in five wormwood samples. Comparison of our results with literature data showed that the wormwood samples from other European countries also vary greatly as was observed with the samples from Estonia.

Differently from the other oils, the Italian wormwood oil contained high amounts of carvone (18.5%), thymol (10.8%), and carvacrol (9.7%). The highest content of neryl butanoate (13.9%) and compounds with curcumene structure (11.3%) was identified in the sample from France. The highest 1,8-cineole content (18.0%) was characteristic of the sample from Spain; the highest content of trans-verbenol was found in the samples from Latvia and Lithuania (9.2% and 11.7%, respectively).

A high content of oxygenated sesquiterpenes (11.9-29.8%) characterized the samples from Italy, Latvia, Lithuania, and Germany (Fig. 2). The principal compounds in these groups were curcumene oxygenated compounds (2.2-7.4%). The oil from German wormwood contained 7.5% [alpha]-bisabolol. Only Armenian wormwood oil was rich in chamazulene (6.6%), in the other oils the chamazulene content was 0-2.1%.

The oils were obtained in the yields of 0.1-1.1% (Table 2), which usually corresponds to literature data [14] and mainly corresponded to the EP standard (not less than 0.2%) [13]. Only samples from Armenia and Spain contain essential oil below the EP standard (both 0.1 %). The oil yields were higher (0.8-1.1 %) in samples from Estonia (Nos 1, 4, 5), also the crude drug of wormwood from Scotland was rather rich in essential oil (0.8%).

CONCLUSIONS

Three chemotypes of wormwood oil, mentioned earlier in the literature [7], were found in the studied samples: thujones rich oil, sabinene acetate rich oil, and epoxyocimenes rich oil. In addition, we found a chemotype of A. absinthium in which oil monoterpenes sabinene and myrcene were predominant from Estonia, Scotland, Moldova, and Hungary. This chemotype of wormwood has not been distinguished in the literature earlier. Some mixed chemotypes were also found. Some compounds with curcumene structure, not earlier reported, were identified in wormwood samples studied using MS data. The Absinthii herba grown in Estonia corresponds to the EP standards in the aspect of the essential oil contents.

ACKNOWLEDGEMENT

Financial support for the work reported here was provided by the Estonian Science Foundation (grant No. 4332).

Received 1 November 2005, in revised form 21 November 2005

REFERENCES

[1.] Montedoro, G. & Bertuccioli, M. The flavour of wines, vermouth and fortified wines In Food Flavours, Part B. The Flavour of Beverages (Morton, I.D. & MacLeod, A. J., eds). Elsevier, Amsterdam, 1986, 171-238.

[2.] Gambelunghe, C. & Melai, P. Absinthe: enjoying a new popularity among young people. Forensic Sci. Int., 2002, 130, 183-186.

[3.] Lachenmeier, D. W., Emmert, J., Kuballa, T. & Sartor, G. Thujone--cause of absinthism? Forensic Sci. Int., 2006, 138, 1-8.

[4.] Bertelli, D. J. & Crabtree, J. H. Naturally occurring fulvene hydrocarbons. Tetrahedron, 1968, 24, 2079-2089.

[5.] Gregor, H. A new acetylenic ester from Artemisia absinthium. Phytochemistry, 1978, 17, 806.

[6.] Chialva, F., Gabri, G., Liddle, P. A. P. & Ulian, F. Qualitative evaluation of aromatic herbs by direct headspace GC analysis. J. High Resol. Chromatogr., Chromatogr. Commun., 1982, 5, 181-188.

[7.] Chialva, F., Liddle, P. A. P. & Doglia, G. Chemotaxonomy of wormwood (Artemisia absinthium L.) I. Composition of the essential oil of several chemotypes. Z. Lebensm. Unters. Forsch., 1983, 176, 363-366.

[8.] Beauhaire, J., Fourrey, J.-L. & Guittet, E. Structure of absintholide a new guaianolide dimer of Artemisia absinthium L. Tetrahedron Lett., 1984, 26, 2751-2754.

[9.] Rucker, G., Manus, D. & Wilbert, S. Homoditerpene peroxides from Artemisia absinthium. Phytochemistry, 1991, 31, 340-342.

[10.] Kennedy, A. I., Deans, S. G., Svoboda, K. P., Grey, A. 1. & Waterman, P. G. Volatile oils from normal and transformed root of Artemisia absinthium. Phytochemistry, 1993, 32, 1449-1451.

[11.] Lawrence, B. M. Progress in essential oils. Perf Flav., 1998, 23, 39-50.

[12.] Chiasson, H., Belanger, A., Bostanian, N., Vincent, C. & Poliquin, A. Acaricidal properties of Artemisia absinthium and Tanacetum vulgare (Asteraceae) essential oils obtained by three methods of extraction. J. Econ. Entomol., 2001, 94, 167-171.

[13.] European Pharmacopoeia. 5th ed. Vol. 2. Council of Europe, Strasbourg, 2005, 2710-2711.

[14.] E/S/C/O/P Monographs: The Scientific Foundation for Herbal Medicinal Products. 2nd ed. Thieme, Stuttgart, 2003, 3-7.

[15.] Heinrich, M., Barnes, J., Gibbons, S. & Williamson, E. M. Fundamentals of Pharmacognosy and Phytotherapy. Churchill Livingstone, Edinburg, 2004, 209-210.

[16.] Evans, W. C. Trease and Evans' Pharmacognosy. 15th ed. Saunders, Edinburg, 2000, 256.

Anne Orav (a) *, Ain Raal (b), Elmar Arak (b), Mati Muurisepp (a), and Tiiu Kailas (a)

(a) Institute of Chemistry, Tallinn University of Technology, Ehitajate tee 5, 19086 Tallinn, Estonia

(b) Institute of Pharmacy, University of Tartu, Nooruse 1, 50411 Tartu, Estonia

* Corresponding author, aorav@chemnet.ee
Table 1. Composition of the essential oil from Artemisia
absinthium L. (boldface designates the principal components)

Compound RI RI
 NB-30 NB-20M

Tricyclene 916 1010
[alpha]-Thujene (MS) 920 1017
[alpha]-Pinene (MS) 930 1015
Camphene 943 1055
Sabinene(MS)# 969 1118
[beta]-Pinene (MS) 970 1095
Myrcene (MS)# 986 1152
[alpha]-Phellandrene (MS)# 999 1164
[alpha]-Terpinene (MS) 1011 1169
p-Cymene (MS)# 1015 1263
1,8-Cineole (MS) 1022 1206
Limonene (MS) 1024 1192
(Z)-[beta]-Ocimene 1030 1220
Artemisia ketone# 1040 1344
[gamma]-Terpinene (MS) 1050 1237
(E)-Sabinene hydrate (MS) 1058 1465
(Z)-Linalool oxide 1056 1425
(E)-Linalool oxide 1076 1453
Terpinolene (MS) 1080 1270
[alpha]-Thujone (MS)# 1087 1418
Linalool (MS)# 1089 1554
[beta]-Thyjone (MS)# 1100 1438
cis-Epoxyocimene 1111 1452
trans-Epoxyocimene# 1115 1468
trans-Sabinol (MS) 1126 1557
cis-Sabinol (MS) 1128 1628
cis-Verbenol 1132 1718
trans-Verbenol (MS)# 1152 1740
Bomeol (MS) 1157 1700
Terpinen-4-o1 (MS) 1166 1604
Myrtenal 1171 1635
[alpha]-Terpineol (MS) 1177 1703
Myrtenol 1180 1796
Verbenone 1182 1796
Nerolms 1217 1806
(E)-Crysantenyl acetate 1220 1802
Neral 1220 1645
Carvone (MS)# 1222 1730
[beta]-Citronellol 1222 1800
(Z)-Anethole 1233
Geraniol (MS) 1240 1857
Linalyl acetate 1242 1557
(Z)-Crysantenyl acetate (MS) 1248 1805
Perillaldehyde 1250 1790
Geranial 1258 1730
(E)-Anethole (MS) 1264 1834
(E)-Sabinyl acetate (MS)# 1273 1667
Thymol 1274 2193
(Z)-Sabinyl acetate 1276 1652
Carvacrol 1286 2220
[alpha]-Terpinyl acetate 1333 1693
Neryl acetate (MS) 1345 1724
Decanoic acid 1362 2280
Geranyl acetate (MS) 1371 1754
[alpha]-Copaene 1373 1473
[beta]-Bourbonene 1381 1500
[beta]-Elemene 1388 1608
Terpinyl propionate 1398
[alpha]-Ionone 1405 1840
Neryl propionate (MS) 1408 1758
(E)-[beta]-Caryophyllene (MS) 1417 1584
Aromadendrene 1441
[alpha]-Humulene 1450 1655
Geranyl propionate 1452 1770
[beta]-Ionone 1464 1930
Curcumenems 1470 1682
[gamma]-Muurolene 1472 1685
Germacrene D 1474 1702
Neryl isobutanoate (MS) 1476 1766
Geranyl isobutanoate 1482 1770
[alpha]-Muurolene 1494 1720
Neryl butanoate (MS) 1498 1857
[gamma]-Cadinene 1500 1743
[delta]-Cadinene 1518 1745
Geranyl butanoate (MS) 1523 1877
Curcumene compound (MS) 1546
 m/z: 186, 157, 142, 171
Germacrene B 1550 1830
(E)-Nerolidol 1552 2040
Nery12-methyl- 1562 1874
 butanoate (MS)#
Neryl-3-methyl- 1566 1876
 butanoate (MS)#
Spathylenol 1568 2126
Caryophyllene oxide 1570 1974
Viridiflorol 1581 2080
Geranyl isovaleriate 1585
Geranyl isovaleriate (MS) 1590 1877
Dodecanal * 1600 2100
Ledol * 1604 2100
Cubenol * 1610 2090
Neryl valeriate (MS) 1618 1974
T-Muurolol 1640 2180
Geranyl valeriate (MS) 1642
(E)-[alpha]-Cadinol 1644 2190
(Z)-[alpha]-Cadinol 1647 2224
Farnesol * 1653 2242
[alpha]-Santanol * 1660
[alpha]-Blsabolol# 1670 2193
n-Heptadecane 1700 1700
Chamazulene (MS)# 1710 2380
Dihydrochamazulene * 1732 2350
Curcumene compound (MS) 1830
 m/z: 186, 157, 143, 142,
 141, 171
Valerenic acid 1850 2305
n-Nonadecane 1900 1900
Curcumene compound (MS) 1938 2930
 m/z: 119, 132, 41, 69,
 145, 105, 159, 227
Curcumene compound (MS) 2000
 m/z: 119, 132, 105, 41,
 554, 591, 159, 185, 241
Curcumene compoundMs 2005
 m/z: 119, 132, 105, 145,
 415, 581
n-Heneicosane 2100 2100
n-Tricosane 2300 2300

Yield, % v/dry wt

Compound Range, Mean,
 % %

Tricyclene 0-0.7 0.08
[alpha]-Thujene (MS) 0-1.5 0.29
[alpha]-Pinene (MS) 0-1.5 0.54
Camphene 0-1.0 0.24
Sabinene(MS)# 0-30.1# 7.82#
[beta]-Pinene (MS) 0-1.8 0.27
Myrcene (MS)# 0.1-38.9# 8.38#
[alpha]-Phellandrene (MS)# 0-7.2# 0.90#
[alpha]-Terpinene (MS) 0-0.6 0.20
p-Cymene (MS)# 0.2-9.6# 2.29#
1,8-Cineole (MS) 0.1-18.0# 2.01#
Limonene (MS) 0-0.9 0.22
(Z)-[beta]-Ocimene 0-0.4 0.09
Artemisia ketone# 0-14.9# 1.00#
[gamma]-Terpinene (MS) 0-4.2 0.59
(E)-Sabinene hydrate (MS) 0-0.3 0.10
(Z)-Linalool oxide 0-0.9 0.10
(E)-Linalool oxide 0-0.4 0.06
Terpinolene (MS) 0-0.5 0.09
[alpha]-Thujone (MS)# 1.1-10.9# 4.16#
Linalool (MS)# 1.1-10.9# 4.16#
[beta]-Thyjone (MS)# 0.1-64.6 8.73
cis-Epoxyocimene 0-2.3 0.26
trans-Epoxyocimene# 0.1-59.7# 5.01#
trans-Sabinol (MS) 0-2.7 0.76
cis-Sabinol (MS) 0-3.5 0.61
cis-Verbenol 0-1.0 0.29

trans-Verbenol (MS)# 0-11.7# 2.11#
Bomeol (MS) 0-1.6 0.29
Terpinen-4-o1 (MS) 0-2.5 1.26
Myrtenal 0-2.1 0.23
[alpha]-Terpineol (MS) 0-1.1 0.35
Myrtenol 0-0.8 0.12
Verbenone 0-0.8 0.12
Nerolms 0-4.0 1.08
(E)-Crysantenyl acetate 0-1.8 0.20
Neral 0-1.8 0.20
Carvone (MS)# 0-18.5# 1.43#
[beta]-Citronellol 0-18.5# 1.43#
(Z)-Anethole 0-0.4 0.05
Geraniol (MS) 0-1.3 0.20
Linalyl acetate 0-1.3 0.20
(Z)-Crysantenyl acetate (MS) 0-1.7 0.35
Perillaldehyde 0-0.4 0.04
Geranial 0-0.3 0.03
(E)-Anethole (MS) 0-7.1 1.00
(E)-Sabinyl acetate (MS)# 0-70.5# 11.39#
Thymol 0-10.2 0.54
(Z)-Sabinyl acetate 0-0.6 0.08
Carvacrol 0-9.7 0.56
[alpha]-Terpinyl acetate 0-0.5 0.05
Neryl acetate (MS) 0-0.6 0.21
Decanoic acid 0-0.4 0.05
Geranyl acetate (MS) 0-0.4 0.13
[alpha]-Copaene 0-0.7 0.13
[beta]-Bourbonene 0-0.9 0.09
[beta]-Elemene 0-0.4 0.08
Terpinyl propionate 0-3.4 0.55
[alpha]-Ionone 0-0.4 0.09
Neryl propionate (MS) 0-1.6 0.34
(E)-[beta]-Caryophyllene (MS) 0-2.1 0.89
Aromadendrene 0-0.4 0.04
[alpha]-Humulene 0-0.9 0.14
Geranyl propionate 0-0.9 0.10
[beta]-Ionone 0-0.6 0.05
Curcumenems 0-7.0# 1.59#
[gamma]-Muurolene 0-1.4 0.16
Germacrene D 0-1.4 0.16
Neryl isobutanoate (MS) 0-3.2 0.89
Geranyl isobutanoate 0-1.6 0.59
[alpha]-Muurolene 0-1.1 0.21
Neryl butanoate (MS) 0.1-13.9# 2.48#
[gamma]-Cadinene 0-1.3 0.19
[delta]-Cadinene 0-0.5 0.05
Geranyl butanoate (MS) 0-0.9 0.18
Curcumene compound (MS) 0-1.1 0.09
 m/z: 186, 157, 142, 171
Germacrene B 0-0.3 0.04
(E)-Nerolidol 0-0.8 0.21
Nery12-methyl- 0.1-9.2# 2.88#
 butanoate (MS)#
Neryl-3-methyl- 0.4-7.3# 3.14#
 butanoate (MS)#
Spathylenol
Caryophyllene oxide 0-2.9 0.88
Viridiflorol 0-2.2 0.32
Geranyl isovaleriate 0-2.3 0.49
Geranyl isovaleriate (MS) 0-4.9 0.91
Dodecanal * 0-0.9 0.17
Ledol * 0-0.6 0.17
Cubenol * 0-0.9 0.06
Neryl valeriate (MS) 0-2.8 0.43
T-Muurolol 0-5.0 0.73
Geranyl valeriate (MS) 0-2.5 0.34
(E)-[alpha]-Cadinol 0-3.2 0.17
(Z)-[alpha]-Cadinol 0-1.8 0.45
Farnesol * 0-3.0 0.32
[alpha]-Santanol * 0-1.3 0.11
[alpha]-Blsabolol# 0-7.5# 0.71#
n-Heptadecane 0-0.8 0.15
Chamazulene (MS)# 0-6.6# 0.80#
Dihydrochamazulene * 0-4.9 0.31
Curcumene compound (MS) 0-2.9 0.35
 m/z: 186, 157, 143, 142,
 141, 171
Valerenic acid 0-4.7 0.37
n-Nonadecane 0-0.7 0.11
Curcumene compound (MS) 0-4.3 0.78
 m/z: 119, 132, 41, 69,
 145, 105, 159, 227
Curcumene compound (MS) 0-2.5 0.53
 m/z: 119, 132, 105, 41,
 554, 591, 159, 185, 241
Curcumene compoundMs 0-4.2 1.07
 m/z: 119, 132, 105, 145,
 415, 581
n-Heneicosane 0-0.9 0.14
n-Tricosane 0.11

Yield, % v/dry wt 0.1-0.8 (EP method)

Compound SD Variation
 n = 19 coefficient

Tricyclene 0.17 2.13
[alpha]-Thujene (MS) 0.40 1.39
[alpha]-Pinene (MS) 0.37 0.68
Camphene 0.25 1.04
Sabinene(MS)# 9.14 1.17
[beta]-Pinene (MS) 0.41 1.54
Myrcene (MS)# 11.74 1.40
[alpha]-Phellandrene (MS)# 1.87 2.08
[alpha]-Terpinene (MS) 0.24 1.21
p-Cymene (MS)# 2.59 1.13
1,8-Cineole (MS) 4.12 2.05
Limonene (MS) 0.21 0.95
(Z)-[beta]-Ocimene 0.12 1.29
Artemisia ketone# 3.38 3.39
[gamma]-Terpinene (MS) 0.96 1.64
(E)-Sabinene hydrate (MS) 0.11 1.16
(Z)-Linalool oxide 0.22 2.28
(E)-Linalool oxide 0.12 1.84
Terpinolene (MS) 0.13 1.43
[alpha]-Thujone (MS)# 2.74 0.66
Linalool (MS)# 2.74 0.66
[beta]-Thyjone (MS)# 15.98 1.83
cis-Epoxyocimene 0.57 2.17
trans-Epoxyocimene# 14.13 2.82
trans-Sabinol (MS) 0.93 1.22
cis-Sabinol (MS) 0.85 1.41
cis-Verbenol 0.34 1.17

trans-Verbenol (MS)# 3.47 1.64
Bomeol (MS) 0.54 1.86
Terpinen-4-o1 (MS) 0.67 0.53
Myrtenal 0.48 2.11
[alpha]-Terpineol (MS) 0.31 0.87
Myrtenol 0.22 1.86
Verbenone 0.22 1.86
Nerolms 1.24 1.14
(E)-Crysantenyl acetate 0.43 2.15
Neral 0.43 2.15
Carvone (MS)# 4.21 2.94
[beta]-Citronellol 4.21 2.94
(Z)-Anethole 0.11 2.29
Geraniol (MS) 0.36 1.77
Linalyl acetate 0.36 1.77
(Z)-Crysantenyl acetate (MS) 0.54 1.52
Perillaldehyde 0.10 2.32
Geranial 0.07 2.37
(E)-Anethole (MS) 1.62 1.62
(E)-Sabinyl acetate (MS)# 17.64 1.48
Thymol 2.34 4.36
(Z)-Sabinyl acetate 0.19 2.21
Carvacrol 2.22 3.97
[alpha]-Terpinyl acetate 0.14 3.02
Neryl acetate (MS) 0.21 1.00
Decanoic acid 0.11 2.27
Geranyl acetate (MS) 0.16 1.23
[alpha]-Copaene 0.21 1.64
[beta]-Bourbonene 0.21 2.49
[beta]-Elemene 0.13 1.62
Terpinyl propionate 0.95 1.72
[alpha]-Ionone 0.15 1.62
Neryl propionate (MS) 0.49 1.43
(E)-[beta]-Caryophyllene (MS) 0.60 0.68
Aromadendrene 0.11 2.56
[alpha]-Humulene 0.17 1.25
Geranyl propionate 0.25 2.62
[beta]-Ionone 0.15 2.86
Curcumenems 1.58 0.99
[gamma]-Muurolene 0.41 2.51
Germacrene D 0.41 2.51
Neryl isobutanoate (MS) 1.00 1.13
Geranyl isobutanoate 0.52 0.89
[alpha]-Muurolene 0.33 1.58
Neryl butanoate (MS) 3.08 1.24
[gamma]-Cadinene 0.33 1.75
[delta]-Cadinene 0.13 2.48
Geranyl butanoate (MS) 0.27 1.52
Curcumene compound (MS) 0.29 3.08
 m/z: 186, 157, 142, 171
Germacrene B 0.08 1.99
(E)-Nerolidol 0.24 1.15
Nery12-methyl- 2.63 0.91
 butanoate (MS)#
Neryl-3-methyl- 2.24 0.71
 butanoate (MS)#
Spathylenol
Caryophyllene oxide 0.93 1.06
Viridiflorol 0.58 1.83
Geranyl isovaleriate 0.52 1.04
Geranyl isovaleriate (MS) 1.26 1.39
Dodecanal * 0.30 1.70
Ledol * 0.19 1.14
Cubenol * 0.21 3.39
Neryl valeriate (MS) 0.71 1.64
T-Muurolol 1.36 1.85
Geranyl valeriate (MS) 0.65 1.93
(E)-[alpha]-Cadinol 0.73 4.36
(Z)-[alpha]-Cadinol 0.57 1.26
Farnesol * 0.77 2.43
[alpha]-Santanol * 0.31 2.84
[alpha]-Blsabolol# 1.72 2.41
n-Heptadecane 0.22 1.44
Chamazulene (MS)# 1.51 1.89
Dihydrochamazulene * 1.12 3.67
Curcumene compound (MS) 0.71 2.02
 m/z: 186, 157, 143, 142,
 141, 171
Valerenic acid 1.10 2.98
n-Nonadecane 0.20 1.83
Curcumene compound (MS) 0.98 1.25
 m/z: 119, 132, 41, 69,
 145, 105, 159, 227
Curcumene compound (MS) 0.68 1.29
 m/z: 119, 132, 105, 41,
 554, 591, 159, 185, 241
Curcumene compoundMs 1.30 1.21
 m/z: 119, 132, 105, 145,
 415, 581
n-Heneicosane 0.23 1.65
n-Tricosane 0.29 2.77

Yield, % v/dry wt

(MS)--identification by GC/MS; *--tentatively identified.

Note: Boldface designates the principal components indicated by #.

Table 2. Content of the principal components and essential oil (%)
of the common wormwood (Artemisia absinthium L.) of different
geographical origin

Sample Origin Sabinene Myrcene L8-
No. Cineole

1 Estonia 21.2 25.6 0.6
2 Estonia 1.4 0.2 0.1
3 Estonia 25.3 29.9 0.4
4 Estonia 3.5 0.8 0.4
5 Estonia 1.7 0.2 0.3
6 France 3.6 5.0 0.8
 France [7] 2.7 0.8 n.d.
 France [7] 0.8 0.5 0.2
7 Hungary 18.1 17.7 0.5
8 Belgium 9.3 5.4 3.9
9 Russia 9.3 0.8 0.6
 Siberia I [7] 0.4 2.1 n.d.
 Siberia II [7] 1.4 3.6 0.2
10 Greece 3.0 2.9 0.3
11 Ukraine 5.1 5.9 0.2
12 Scotland 30.1 18.0 0.2
13 Armenia 0.9 2.2 0.4
14 Moldova 9.2 38.9 0.1
15 Latvia 3.4 2.8 4.1
16 Lithuania 2.7 2.5 3.6
17 Italy 0.2 0.1 0.3
 Italy [7] 4.0 3.2 0.2
 Italy [7] 6.3 1.4 0.3
 Italy [7] 2.2 2.1 0.1
18 Spain tr. 0.1 18.0
19 Germany 0.6 0.3 3.4

Sample Origin Linalool+ [beta]- Epoxyocimenes
No. [alpha]- Thujone
 thujone

1 Estonia 1.7 4.1 1.3
2 Estonia 1.1 1.3 59.7
3 Estonia 3.4 0.1 1.4
4 Estonia 2.4 64.6 0.2
5 Estonia 2.5 2.3 0.7
6 France 10.3 2.0 0.4
 France [7] 1.8 0.4 48.9
 France [7] 0.8 0.7 0.1
7 Hungary 4.2 4.5 3.0
8 Belgium 3.8 3.5 0.5
9 Russia 1.9 1.7 22.1
 Siberia I [7] 2.7 0.6 n.d.
 Siberia II [7] 12.7 7.6 1.8
10 Greece 4.5 38.7 0.8
11 Ukraine 5.4 6.3 0.4
12 Scotland 5.0 3.5 0.8
13 Armenia 6.1 3.1 0.4
14 Moldova 3.0 0.4 0.6
15 Latvia 5.8 6.2 0.6
16 Lithuania 4.1 4.6 1.1
17 Italy 1.9 12.3 3.6
 Italy [7] 0.6 n.d. 56.6
 Italy [7] 2.2 40.6 23.1
 Italy [7] 1.1 5.2 33.7
18 Spain 10.9 6.2 1.3
19 Germany 1.1 0.4 1.2

Sample Origin Sabinyl Curcumene Neryly-3-
No. acetate structures butanoate

1 Estonia 0.4 5.5 0.8
2 Estonia 23.6 0.1 0.5
3 Estonia 0.2 2.7 2.5
4 Estonia 18.2 0.1 0.1
5 Estonia 70.5 0.3 1.4
6 France 0.3 11.3 13.9
 France [7] n.d. n.d. 1.0
 France [7] 84.5 0.3 0.2
7 Hungary n.d. 2.6 3.3
8 Belgium 18.6 1.1 2.9
9 Russia tr. 2.9 4.9
 Siberia I [7] 31.5 1.7 7.9
 Siberia II [7] 7.9 1.0 7.0
10 Greece 0.9 3.0 2.5
11 Ukraine 4.9 7.8 3.8
12 Scotland 0.2 2.1 0.5
13 Armenia 34.2 5.7 1.8
14 Moldova 5.7 2.4 2.0
15 Latvia 23.6 9.0 0.6
16 Lithuania 13.7 6.3 0.5
17 Italy 11.4 7.1 2.4
 Italy [7] n.d. 0.4 0.3
 Italy [7] 0.9 n.d. 1.0
 Italy [7] 11.5 0.3 0.9
18 Spain 0.2 1.4 0.1
19 Germany n.d. 8.9 2.7

Sample Origin Neryly-3- Essential
No. methyl oil
 butanoate

1 Estonia 0.4 0.8
2 Estonia 0.9 0.4
3 Estonia 0.9 0.5
4 Estonia 0.5 0.8
5 Estonia 0.4 1.1
6 France 7.3 0.7
 France [7] 1.0 1.6
 France [7] 0.2
7 Hungary 2.0 0.3
8 Belgium 1.5 0.7
9 Russia 5.5 0.3
 Siberia I [7] 9.1 0.3
 Siberia II [7] 6.6 1.2
10 Greece 3.7 0.3
11 Ukraine 7.3 0.4
12 Scotland 1.7 0.8
13 Armenia 3.5 0.1
14 Moldova 3.0 0.2
15 Latvia 4.7 0.4
16 Lithuania 4.1 0.2
17 Italy 2.6 0.2
 Italy [7] 0.3 0.8
 Italy [7] 1.2 0.5
 Italy [7] 0.7 0.5
18 Spain 5.9 0.1
19 Germany 3.8 0.3

tr.--trace (<0.05%); n.d.--not determined.
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Author:Orav, Anne; Raal, Ain; Arak, Elmar; Muurisepp, Mati; Kailas, Tiiu
Publication:Estonian Academy of Sciences: Chemistry
Date:Sep 1, 2006
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