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Content and composition of essential oils in some Asteraceae species/ Eeterliku oli sisaldus ja koostis monedes Asteraceae sugukonna taimeliikides.

INTRODUCTION

The Asteraceae family contains several species known as popular medicinal plants. The concept that plants can be classified also on the basis of their chemical constituents is not new [1,2]. According to an earlier study [3], the most popular medicinal plant in Estonia during the 20th century was Chamomilla recutita (L.) Rauschert (= Matricaria recutita L.), which was also very widely used in the Soviet Union, Russia, Germany, etc. In several publications (an overview in [3]) it is observed that the chemical composition of the essential oil of Chamomilla recutita is rather similar to that of Chamomilla suaveolens (Pursh) Rydb. (= Matricaria suaveolens (Pursh) Buch.; M. discoidea DC.; M. matricarioides (Less.) Porter). The chamomile inflorescence is anti-inflammatory and spasmolytic [4].

As many taxonomically related plants may contain structurally similar compounds [5], it could be useful to investigate also the composition of essential oils of other species of the Asteraceae family, morphologically and chemotaxonomically similar to the genus Chamomilla, such as Anthemis tinctoria L., Matricaria perforata Merat (= M. inodora L.; Tripleurospermum inodorum (L.) Sch. Bip.), and Leucanthemum vulgare Lam. (Chrysanthemum leucanthemum L.).

These three species are not yet known as medicinal plants of allopatic medicine. The antibacterial and bactericidal activity of extracts and their fractions of aerial parts of Anthemis tinctoria against Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis was determined [6]. Mogosan et al. [7] mentioned that the tincture of A. tinctoria promotes potassium retention, the saponins of the same species increase urinary excretion of uric acid. According to the Patent No. RU 2311194, the extract of Leucanthemum vulgare is a constituent of a homeopathic agent possessing an antiviral effect [8].

The composition of the essential oils of two well-known species of the genus Chamomilla, especially of Chamomilla recutita, has been rather well investigated within the last 25 years [9-23]. At the same time, the composition of the essential oil of Chamomilla suaveolens has been the subject of rather limited phytochemical investigations [9, 24-33], realized basically in the former USSR (Russia, Estonia, and Lithuania). The main biologically active compounds in the oils of Chamomilla recutita and C. suaveolens were found to be (E)-farnesene, (Z)- and (E)-en-yne-dicycloether, and farnesole [3].

However, drastically little is known about the composition of the essential oil of other Asteraceae species mentioned above [34-38]. The main constituents of the essential oil of Anthemis tinctoria from Creece have been found to be spathulenol, caryophyllene oxide, and T-cadinol [37], but 1,8-cineole (8%), [beta]-pinene (7%), decanoic acid (5%), and [alpha]-pinene (4%) in a sample from Slovakia [35,38].

The essential oil of Matricaria perforata from Germany is dominated by 2Z,8Z-matricaria ester (75%), accompanied by several other characteristic polyines, such as 8Z-2,3-dihydro-matricaria ester, 2E- and 2Z-lachnophyllum ester, 2E-dehydro-matricaria ester, and 5E,9Z-matricaria lactone [34]. The major constituents of the oil of Leucanthemum vulgare from Georgia include nerolidol, [alpha]-bisabolol, farnesol, and farnesene [36].

The current paper presents the content and the results of GC-FID and GC-MS analyses of the essential oils of inflorescences of Chamomilla recutita, Chamomilla suaveolens, Anthemis tinctoria, Matricaria perforata, and Leucanthemum vulgare growing in Estonia.

EXPERIMENTAL

Plant material

The plant material--samples of herbs of wild-growing Anthemis tinctoria, Matricaria perforata, Leucanthemum vulgare, and Chamomilla suaveolens--was collected in July 2007 from North Estonia (Harjumaa, Virla). The sample of Chamomilla recutita was from a cultivated plant and it was collected in June 2007 in the experimental garden of the University of Tartu. All collected fresh samples were dried at room temperature in a well-ventilated room. The dried drug samples were preserved in tightly closed bumper bags at room temperature in the absence of light. Voucher specimens and drug samples are deposited at the Department of Pharmacy, University of Tartu, Estonia.

Isolation of essential oil

The essential oils were isolated from dried samples of Asteraceae species by the distillation method described in the European Pharmacopoeia [39] for Matricariae flos by using the Clevenger-type apparatus. A 1000 mL round-bottomed flask, 30 g of plant material, and 300 mL of water as the distillation liquid were used. Cyclohexane (1 mL in a graduated tube) was added to take up the essential oil. The distillation time was 4 h at a rate of 3-4 mL/min. The oils were stored prior to analysis in ampoules and were analysed within a week.

Gas chromatography with FID

The essential oils were analysed using a Chrom-5 chromatograph with FID on two fused silica capillary columns with two stationary phases: poly(5% diphenyl-95% polydimethyl siloxane) ([SPB.sup.TM]-5, 30 m x 0.25 mm, Supelco, Switzerland) and polar polyethylene glycol (SW-10, 30 m x 0.25 mm, Supelco, Switzerland). Film thickness of both stationary phases was 0.25 [micro]m. Helium with the split ratio 1 : 150 and the flow rate 30-35 cm/s was applied as the carrier gas. The temperature program was from 50 to 250[degrees]C at 2[degrees]C/min, the injector temperature was 250[degrees]C. A Spectra-Physics SP4100 integrator was used for data processing.

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 with literature data [40-43].

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

Gas chromatography-mass spectrometry

GC/MS analysis was carried out using GCMS-QP2010 (Shimadzu, Japan) on a fused silica capillary column (30 m x 0.32 mm) with a bonded stationary phase: poly(5% diphenyl-95% dimethyl siloxane) (ZB-5, Zebron). The film thickness of the stationary phase was 0.25 nm. The carrier gas was helium with the split ratio of 1 : 8 and flow rate 44.4 cm/s. The temperature program was 1 min at 60[degrees]C and then from 60 to 300[degrees]C at 8[degrees]C/min. The injector temperature was 280[degrees]C. The MS source temperature was 200[degrees]C. The MS detector was operated in the EI mode 70 eV at a scan rate 2 scans/s with an acquisition mass range of 40-500 u.

RESULTS AND DISCUSSION

Content of essential oils

The content of essential oils in the investigated plants of Asteraceae species ranged from traces up to 0.2% based on dry weight (Table 1). The highest oil content was found in Matricaria perforate (0.2%) and the lowest in Anthemis tinctoria (only in traces). As it was shown in [38], the content of essential oil in the individual floral parts of A. tinctoria from Slovakia ranges from 0.02% to 2.78%. The highest content of essential oil was found in the tongue-shaped flowers in the second development stage.

A very low yield of essential oil (0.03%) was found also in the sample of Leucanthemum vulgare of Estonian origin. The essential oil of L. vulgare from Georgia made up 0.4-0.5% of the air-dried mass [36].

The extremely low concentrations of essential oil in A. tinctoria and L. vulgare can probably be explained by the origin of the investigated samples. Our earlier experience shows that there may exist a significant difference between the minimum and maximum yield of essential oil in other plants: 10-fold difference in Chamomilla recutita [23], 11-fold in Achillea millefolium [44] and Salvia officinalis [45], 16-fold in Levisticum officinale [46], 14-fold in Thymus serpyllum [47], 5-fold in Pimpinella anisum [48], and 6-fold in Valeriana officinalis [49] collected or obtained as commercial samples from different retail pharmacies of various countries.

The Chamomilla species--C. recutita and C. suaveolens--contained 0.15% and 0.12% essential oil, respectively. According to the standards of the 10th edition of the U.S.S.R Pharmacopoeia [50], the inflorescences of C. recutita and C. suaveolens should contain at least 0.3% and 0.2% essential oil. Consequently, the oil yield in the investigated Asteraceae species was rather low although the distillation method corresponded to the monograph of Matricariae flos (inflorescences of C. recutita) in the European Pharmacopoeia [39] and the distillation time (4 h) was quite long.

Composition of essential oils

Essential oil components of five Asteraceae species and their percentages and mode of identification are reported in Table 1. A total of 115 compounds were identified in the studied samples, which accounted for 49.1-98.5% of the total amount of oil. The largest number of compounds were identified in the oil of Matricaria perforata (84). In other oils 52-62 compounds were identified. From the essential oil of the flower heads of M. perforata growing in Germany about 50 compounds were found [34]. The amount of polyacetylenes in the oil of M. perforata from Estonia (88.6%) was practically equal to their concentration found in Germany (88.8%) [34].

In the oil of Leucanthemum vulgare we succeeded in identifying only 49.1% of the total oil. The mass spectra of 23 incompletely identified peaks are presented in Table 2. The oil of L. vulgare contained much more aliphatic acids and esters than the oils of the other investigated Asteraceae species [9-36] but had a very low concentration of polyacetylenes (Table 1).

The main constituents found in the essential oils of the studied Asteraceae species were bisabolol oxide A, bisabolone oxide A, (Z)-en-yne-dicycloether, bisabolol oxide B, [alpha]-bisabolol, and chamazulene in the essential oil of Chamomilla recutita; (Z)-en-yne-dicycloether, geranyl isovalerate, and (E)-[beta]-farnesene in C. suaveolens; (Z,Z)-matricaria ester, (E)-[beta]-farnesene , matricaria ester isomer, and matricaria lactone in Matricaria perforata; [alpha]-eudesmol, [gamma]-cadinol, and [gamma]-cadinene in Anthemis tinctoria; and (E)-[beta]-farnesene in Leucanthemum vulgare (Table 1).

Chamazulene is the typical constituent of the essential oil of C. recutita. It has been found in the range from 0.7% to 15.3% in samples of C. recutita [19,23] and from 0% to 42% in Achillea millefolium growing wild and/or cultivated in different countries [44], but was not found in the oil of C. suaveolens [33]. The presence of chamazulene in the essential oil of C. suaveolens may depend on its chemotypes or growing places.

As shown in Table 1, the oil composition of the studied species was quite different. Only 14 compounds were found in all plant oils studied: decanoic acid, (E)-[beta]-farnesene , germacrene D, caryophyllene oxide, geranyl isovalerate, [gamma]-eudesmol, bisabolol oxide A, hexahydrofarnesyl acetone, (Z)-en-yne-dicycloether, n-nonadecane, e-eikosane, [gamma]-palmitolactone, n-tricosane, and n-pentacosane.

CONCLUSION

In this study the content and composition of inflorescences of five Asteraceae species were investigated. The oil yield in the investigated Asteraceae species was rather low. The composition of the essential oils of these five species was compared. Only 14 compounds were found in all analysed oils. The composition of the oils of Chamomilla recutita, C. suaveolens, and Matricaria perforata was relatively similar; however, the oil of Leucanthemum vulgare was quite different from the other oils studied.

doi: 10.3176/proc.2011.1.06

Received 17 November 2009, revised 2 February 2010, accepted 9 February 2010

REFERENCES

[1.] Evans, W. C. Trase and Evans Pharmacognosy. 15th edn. Saunders, Edinburgh, 2000.

[2.] Soukand, R. and Raal, A. How the name Arnica was borrowed into Estonian. Trames, 2008, 12, 29-39.

[3.] Raal, A. and Arak, E. Eesti etnofarmakognoosia elujoust kummelite naitel [About the vitality of Estonian ethnopharmacognosy with the example of camomile]. Maetagused, 2006, 34, 149-184 (in Estonian).

[4.] Murav'eva, D. A., Samylina, I. A., and Yakovlev, G. P. Farmakognoziya. 4th edn. Meditsina, Moscow, 2002 (in Russian).

[5.] Heinrich, M., Barnes, J., Gibbons, S., and William son, E. M. Fundamentals of Pharmacognosy and Phytotherapy. Churchill Livingstone, Edinburgh, 2004.

[6.] Akgul, C. and Saglikoglu, G. Antibacterial activity of crude methanolic extract and its fractions of aerial parts of Anthemis tinctoria. Indian J. Biochem. Biol., 2005, 6, 395-397.

[7.] Mogosan, C., Hanganu, D., Aciu, M., and Muresan, L. Evaluation of diuretic, saluretic and uricosuric actions of the tinctures and saponins from Anthemis tinctoria L. (Asteraceae) and Pulmonaria officinalis L. (Boraginaceae). Farmacia, 2005, 50, 28-34 (in Romanian).

[8.] Buryakova, I. V., Kurilova, A. I., Badytchik, L. I., and Zamarenov, N. A. Homeopathic agent Anaviarin-Homeoantigrippin possessing antiviral effect. Patent No RU 2311194, application No RU 2006-130539, 2007.

[9.] Arak, E. H., Raal, A. E., and Tammeorg, J. K. Aerial parts of Matricaria matricarioides: a substitute for Matricaria recutita flowers. Farmatsiya, 1986, 35, 19-22 (in Russian).

[10.] Vuorela, H., Holm, Y., Hiltunen, R., Tarvela, T., and Laitinen, A. Extraction of the volatile oil in chamomile flowerheads using supercritical carbon dioxide. Flavour Fragr. J., 1990, 5, 81-84.

[11.] Zekovic, Z., Pekic, B., Lepojevic, Z., and Petrovic, L. Chromatography in our investigations of chamomile (Matricaria chamomilla L.). Chromatographia, 1990, 39, 587-590.

[12.] Marjanovic, N., Pekic, B., Petrovic, L., Lepojevic, Z., and Zekovic, Z. Determination of different components of chamomile essential oil (Aetheroleum chamomillae) using GC + MS. Zbor. Rad., 1992, 23, 189-195.

[13.] Pekic, B., Zekovic, Z., Marjanovic, N., and Petrovic, L. Chamomile flowers (Chamomillae flos) extraction by supercritical carbon dioxide. In Congress of Pharmacists of Yugoslavia. Belgrad, 1994, 354-355.

[14.] Pekic, B., Zekovic, Z., Petrovic, L., and Adamovic, D. Chemical investigation of tubular and ligulate chamomile flowers (Matricaria chamomilla L.). In Congress of Pharmacists of Yugoslavia. Belgrad, 1994, 352-353.

[15.] Reverchon, E. and Senatore, F. Supercritical carbon dioxide extraction of chamomile essential oil and its analysis by gas chromatography-mass spectrometry. J. Agric. Food Chem., 1994, 42, 154-158.

[16.] Grgesina, D., Mandic, M. L., Karuza, L., Klapec, T., and Bockinac, D. Chemical composition of different parts of Matricaria chamomilla. Prehrambeno-tehnoloska i biotehnoloska revija, 1995, 33, 111-113.

[17.] Orav, A., Kailas, T., and Ivask, K. Volatile constituents of Matricaria recutita L. from Estonia. Proc. Estonian Acad. Sci. Chem., 2001, 50, 39-41.

[18.] Pino, J. A., Bayat, F., Marbot, R., and Aguero, J. Essential oil of chamomile Chamomilla recutita (L.) Rausch from Iran. J. Essent. Oil. Res., 2002, 14, 407-408.

[19.] Raal, A., Arak, E., Orav, A., and Ivask, K. Comparison of the essential oil from Matricaria recutita L. of different origins. Ars Pharmaceutica, 2003, 44, 159-165.

[20.] Sashidhara, K. V., Verma, R. S., and Ram, P. Essential oil composition of Matricaria recutita L. from the lower region of the Himalayas. Flav. Fragr. J., 2006, 21, 274-276.

[21.] Gosztola, B., Nemeth, E., Kozak, A., and Sarosi, S. Comparative evaluation of Hungarian chamomile (Matricaria recutita L.) populations. Acta Horticult., 2007, 749, 157-162.

[22.] Bucko, A., Daniel, S., and Salamon, I. The essential oil quality of chamomile, Matricaria recutita L., after its large-scale distillation. Acta Horticult., 2007, 749, 269-273.

[23.] Orav, A., Raal, A., and Arak, E. Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries. Nat. Prod. Res., 2010, 24, 48-55.

[24.] Prosovskii, M. A., Oleshko, G. I., Syuzeva, Z. F., Mel'ni kova, O. A., and Evtikheeva, O. V. Utilization of Matricaria matricarioides (Less.) Porter. Farmatsiya, 1984, 33, 28-30 (in Russian).

[25.] Prosovskii, M. A., Rybalko, K. S., Sheichenko, V. I., Shchablinskii, A. N., and Oleshko, G. I. Chemical composition of Matricaria matricarioides. Khim. Farm. Zh+, 1985, 19, 981-984 (in Russian).

[26.] Oleshko, G. I. and Prosovskii, M. A. Dynamics of the contents of essential oil and its main components in Matricaria discoidea DC. Rast. Res., 1986, 22, 377-382 (in Russian).

[27.] Arak, E. H. and Raal, A. E. The possibility of utilization of aerial parts of Matricaria dioscoidea DC. as herbal substance. Rast. Res., 1987, 23, 584-590 (in Russian).

[28.] Arak, E. H., Raal, A. E., Pehk, T. I., and Maeorg, U. J. Geranylisovalerianate, trans-beta-farnesene and herniarin as components of Matricaria discoidea. Khim. Prir. Soedin., 1988, 6, 804-806 (in Russian).

[29.] Orav, A., Kailas, T., and Kann, J. Volatile constituents of Matricaria matricarioides (Less.) Port. J. Essent. Oil. Res., 1999, 11, 243-245.

[30.] Pervyshina, G. G., Efremov, A. A., Gordienko, G. P., and Agafonova, E. A. Content of biologically active substances of Chamomilla recutita and Chamomilla suaveolens growing in Russia. Khim. Rast. Syr'ya, 2002, 3, 21-24 (in Russian).

[31.] Lopes, D. and Kolodziejczyk, P. P. Essential oil composition of pineapple-weed (Matricaria discoidea DC.) grown in Canada. J. Essent. Oil Bear. PL, 2005, 8, 178-182.

[32.] Ma, C.-M., Winsor, L., and Daneshtalab, M. Quantification of spiroether isomers and herniarin of different parts of Matricaria matricarioides and flowers of Chamaemelum nobile. Phytochem. Anal., 2006, 18, 42-49.

[33.] Orav, A., Sepp, J., Kailas, T., Muurisepp, M., Arak, E., and Raal, A. Composition of essential oil of aerial parts of Chamomilla suaveolens from Estonia. Nat. Prod. Commun., 2010, 5, 133-136.

[34.] Bar, B. and Schultze, W. Composition of the essential oil of the flower heads of Matricaria perforate. Planta Med., 1996, 62, 332-335.

[35.] Holla, M., Svajdlenka, E., Vaverkova, S., Zibrunova, B., Jozef, T., and Harvranek, E. Composition of the oil from the flowerheads of Anthemis tinctoria L. cultivated in Slovak Republic. J. Essent. Oil Res., 2000, 12, 714-716.

[36.] Sagareishvili, T. G. Essential oil of Leucanthemum vulgare. Chem. Nat. Compd., 2002, 38, 295-296.

[37.] Saroglou, V., Dorizas, N., Kypriotakis, Z., and Skaltsa, H. D. Analysis of the essential oil composition of eight Anthemis species from Greece. J. Chromatogr., 2006, 1104, 313-322.

[38.] Vaverkova, S., Holla, M., Mikolasova, M., Haban, M., Otepka, P., and Vozar, I. Qualitative properties and content of essential oil in the flowerheads of Anthemis tinctoria L. Acta Hort. (ISHS), 2007, 749, 283-287.

[39.] European Pharmacopeia. 5th edn. Council of Europe, Strasbourg, 2005.

[40.] Davies, N. W. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J. Chromatogr., 1990, 503, 1-25.

[41.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC-MS identification. Mono- and sesquiterpenes. Rastitel. Res., 1996, 32, 48-58.

[42.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC-MS identification. Oxygen containing derivatives of mono- and sesquiterpenes hydrocarbons. Rastitel. Res., 1997, 33, 16-28.

[43.] Zenkevich, I. G. Analytical parameters of components of essential oils for their GC and GC-MS identification. Acetates of terpenic alcohols. Rastitel. Res., 1999, 35, 30-37.

[44.] Orav, A., Arak, E., and Raal, A. Phytochemical analysis of the essential oil of Achillea millefolium L. from various European countries. Nat. Prod. Res., 2006, 20, 1082-1088.

[45.] Raal, A., Orav, A., and Arak, E. Composition of the essential oil of Salvia officinalis L. from various European countries. Nat. Prod. Res., 2007, 21, 406-411.

[46.] Raal, A., Arak, E., Orav, A., Kailas, T., and Muuri sepp, M. Composition of the essential oil of Levisticum officinale W.D.J. Koch from some European countries. J. Essent. Oil Res., 2008, 20, 318-322.

[47.] Paaver, U., Orav, A., Arak, E., Maeorg, U., and Raal, A. Phytochemical analysis of the essential oil of Thymus serpyllum L. growing wild in Estonia. Nat. Prod. Res., 2008, 22, 108-115.

[48.] Orav, A., Raal, A., and Arak, E. Essential oil composition of Pimpinella anisum L. fruits from various European countries. Nat. Prod. Res., 2008, 22, 227-232.

[49.] Raal, A., Arak, E., Orav, A., Kailas, T., and Muuri sepp, M. Variation in the composition of the essential oil of commercial Valeriana officinalis L. roots from different countries. J. Essent. Oil Res., 2008, 20, 524-529.

[50.] U.S.S.R. Pharmacopoeia. 10th edn. Meditsina, Moscow, 1968 (in Russian).

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

(a) Department of Pharmacy, University of Tartu, Nooruse 1, 50411 Tartu, Estonia

(b) Institute of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia

* Corresponding author, ain.raal@ut.ee
Table 1. Composition of the essential oils from some species of
Asteraceae. The main components are indicated in bold. Identification
methods: 1--RI(SPB-5), 2--RI(SW-10), 3--mass spectra

Compound                                    RI

                                       SPB-5   SW-10

[alpha]-Pinene                          927    1025
Sabinene                                966    1120
[beta]-Pinene#                          969    1116
6-Methyl-5-hepten-2-one                 984    1344
Myrcene#                                988    1168
2-Pentylfuran                           990    1236
n-Octanal                              1002    1278
[alpha]-Terpinene                      1012    1181
p-Cymene                               1018    1272
Limonene                               1023    1202
1,8-Cineol#                            1026    1208
(E)-[beta]-Ocimene                     1044    1254
[gamma]-Terpinene                      1054    1246
Artemisia ketone                       1058    1353
cis-Limonene hydrate                   1065    1257
Terpinolene                            1084    1283
Perillene                              1100    1507
2-Methylbutyl 2-methylbutyrate         1100    1300
n-Nonanal                              1103    1400
Isoamyl isovalerate                    1110    1309
1-Octenyl acetate                      1113    1386
n-Pentyl isovalerate                   1129    1382
Pinocarvone                            1162    1565
Octanoic acid                          1172    2093
Terpinen-4-ol                          1172    1606
p-Cymen-8-ol                           1178    1846
[alpha]-Terpineol                      1187    1704
cis-3-Hexenyl isovalerate              1234    1454
Nonanoic acid                          1290    2190
n-Undecanal                            1304    1600
(E)-Carvyl acetate                     1330    1756
[delta]-Elemene                        1334    1462
2H-2,4a-Ethanonaphthalene,             1334    1493
  1,3,4,5,6,7-hexa-hydro-
  2,5,5-trimethyl-
(E,E)-2,4-Decadienal                   1334    1816
[alpha]-Cubebene                       1343    1454
[alpha]-Copaene                        1367    1485
Isoeugenol                             1367    2213
Geranyl acetate                        1380    1764
(Z)-Jasmone                            1390    1935
Decanoic acid#                         1398    2292
(E)-[beta]-Caryophyllene               1408    1588
Aromadendrene                          1440    1590
[beta]-Gurjunene                       1442    1600
[alpha]-Humulene                       1449    1626
Geranyl acetone                        1450    1876
(E)-[beta]-Farnesene#                  1455    1668
8-Methylcoumarin                       1461    2308
Alloaromadendrene                      1464    1632
Germacrene D                           1470    1696
[alpha]-Amorphene                      1479    1744
[alpha]-Muurolene                      1485    1725
Geranyl isobutanoate                   1488    1882
Isopentyl phenyl acetate               1488
Bicyclogermacrene                      1490    1720
[C.sub.15][H.sub.24] (1)               1490    1742
n-Undecanoic acid                      1492    2350
n-Tridecanal                           1500    1795
Z-Lachnohyllum methyl ester#           1500    2250
Isofaurinone                           1503    1900
[delta]-Cadinene#                      1510    1750
[C.sub.15][H.sub.26]O (2)#             1510    1935
Matricaria ester *#                    1511    2256
(ZZ)-Matricaria ester#                 1516    2321
[gamma]-Cadinene#                      1523    1752
E-Lachnohyllum methyl ester            1528    2248
[C.sub.15][H.sub.24]O (3), hotrienol   1528    1938
  structure
Cadina-1,4-diene                       1530    1798
Elemol                                 1543    2100
NI (4), hotrienol structure,           1554    2035
  acetate?
NI (5), farnesene epoxide?             1554
NI (6), isocaryophyllene oxide?        1563
Dehydromatricaria ester *              1563    2412
(E)-Nerolidol                          1563    2032
Dendrolasin                            1563    2044
Lauric acid                            1568    2495
Spatulenol#                            1568    2120
Geranyl butanoate                      1570    1883
Caryophyllene oxide#                   1572    1965
Matricaria lactone *                   1578    2584
Dihydronerolidol                       1580    2108
Humulene-1,2-epoxide                   1580
trans-a-Bisabolene epoxide             1582    2108
NI (7), benzenemethanol,               1595    2324
  [alpha]-1-octenyl-?
Viridiflorol                           1595    2044
NI (8)                                 1600    2051
NI (9), sesquiterpene acetate          1600    2057
Geranyl isovalerate#                   1608    1924
Cubenol                                1619    2100
(Z)-[alpha]-Bergamotol                 1619    2236
NI (10)                                1620    2108
NI (11), dendrolasin isomer *          1622    2100
[C.sub.15][H.sub.24]O (12),            1625    2127
  nerolidol structure
[gamma]-Eudesmol#                      1627    2157
[gamma]-Cadinol#                       1635    2182
T-Muurolol#                            1641    2200
NI (13)                                1642    2108
[C.sub.15][H.sub.24]O (14),            1642    2200
  chamomillol
Bisabolol oxide B#                     1644    2125
[alpha]-Eudesmol#                      1646    2218
Alloaromadendrene epoxide              1657    2226
Hexadecahydrocyclobuta[1,2:3,4]        1673    1900
  di-cyclooctene
Bisabolone oxide A#                    1675    2163
[alpha]-Bisabolol#                     1688    2215
cis-[alpha]-Bisabolene epoxide#        1688    2212
(Z)-Lancelol ([beta]-                  1690
  bisabolen-12-ol)
Dimethylpentadecane                    1700    1700
Aromadendrene oxide 2                  1700    2421
Geranyl tiglate                        1700    2184
n-Pentadecanal                         1711    2024
Chamazulene#                           1713    2370
Citronellyl hexanoate                  1715    2321
Bisabolol oxide A#                     1748    2421
Benzyl benzoate                        1750    2630
Myristic acid                          1773    2713
NI (15) MW236                          1775
NI (16) MW234                          1786
n-Octadecane                           1800    1800
NI (17) MW232, benzenemethanol,        1800
  [alpha]-1-decenyl-
NI (18)                                1807    2421
NI (19), indene structure              1826
Farnesyl acetate                       1828    2265
Hexahydrofarnesyl acetone              1842    2160
NI (20), [C.sub.17][H.sub.16]          1849    2265
  [O.sub.2], ester
(Z)-En-yne-dicydoether#, MW200         1866
NI (21)#, indene structure?            1870    2412
(E)-En-yne-dicycloether, MW200         1882
n-Nonadecane                           1900    1900
NI (22)                                1914    2432
(Z)-En-yne-dicycloether, MW214         1933
Palmitic acid                          1975    2920
n-Eicosane                             2000    2000
13-Hexyloxacyclotridec-10-ene-2-one,   2045    2432
  MW280
[C.sub.15][H.sub.14][O.sub.2] (23),    2063    2435
  benzhydryl acetate?
[gamma]-Palmitolactone                 2100
cis-Linoleic acid                      2120
9,12-octadecadien-1-ol, (Z,Z)-         2123
n-Tricosane                            2300    2300
n-Pentacosane                          2500    2500

GROUPS OF COMPONENTS
Monoterpenes
Oxygenated monoterpenes
Sesquiterpenes
Oxygenated sesquiterpenes
Polyacetylenes
Aliphatic acid and esters
Other compounds
Not identified
  Total
  Oil volume, %

Compound                               Percentage composition

                                       Chamomilla   Chamomilla
                                        recutita    suaveolens

[alpha]-Pinene                             tr           tr
Sabinene                                   --           --
[beta]-Pinene#                            0.2          0.2
6-Methyl-5-hepten-2-one                   0.1           tr
Myrcene#                                  0.1          2.9#
2-Pentylfuran                              --           tr
n-Octanal                                 0.2           tr
[alpha]-Terpinene                          tr           tr
p-Cymene                                  0.2           tr
Limonene                                   tr          0.5
1,8-Cineol#                               0.2           tr
(E)-[beta]-Ocimene                        0.2           tr
[gamma]-Terpinene                         0.2           --
Artemisia ketone                          0.8           --
cis-Limonene hydrate                       --           --
Terpinolene                                --           --
Perillene                                  --          0.1
2-Methylbutyl 2-methylbutyrate            0.2           --
n-Nonanal                                 0.2          0.1
Isoamyl isovalerate                        --           tr
1-Octenyl acetate                          --           --
n-Pentyl isovalerate                       --           tr
Pinocarvone                                --           --
Octanoic acid                              --           --
Terpinen-4-ol                             0.1           tr
p-Cymen-8-ol                               --           tr
[alpha]-Terpineol                         0.1           tr
cis-3-Hexenyl isovalerate                  tr           --
Nonanoic acid                              --           --
n-Undecanal                                --           tr
(E)-Carvyl acetate                         --           --
[delta]-Elemene                            --           --
2H-2,4a-Ethanonaphthalene,                 --           --
  1,3,4,5,6,7-hexa-hydro-
  2,5,5-trimethyl-
(E,E)-2,4-Decadienal                       --           --
[alpha]-Cubebene                           --           --
[alpha]-Copaene                            tr           --
Isoeugenol                                 --           --
Geranyl acetate                            --           tr
(Z)-Jasmone                                --           --
Decanoic acid#                            0.2          0.8
(E)-[beta]-Caryophyllene                  0.1           --
Aromadendrene                              --           --
[beta]-Gurjunene                           --           --
[alpha]-Humulene                           --           --
Geranyl acetone                            --           --
(E)-[beta]-Farnesene#                     2.3#        15.6#
8-Methylcoumarin                           --           --
Alloaromadendrene                         0.1          0.1
Germacrene D                              0.2          0.5
[alpha]-Amorphene                          --           tr
[alpha]-Muurolene                         0.2           --
Geranyl isobutanoate                       --          0.1
Isopentyl phenyl acetate                   --           --
Bicyclogermacrene                          tr           --
[C.sub.15][H.sub.24] (1)                   --           --
n-Undecanoic acid                         0.2           tr
n-Tridecanal                               tr           --
Z-Lachnohyllum methyl ester#               --           --
Isofaurinone                              0.2          1.4
[delta]-Cadinene#                         0.1          0.4
[C.sub.15][H.sub.26]O (2)#                 --           --
Matricaria ester *#                        --           --
(ZZ)-Matricaria ester#                     --           --
[gamma]-Cadinene#                         0.1          0.2
E-Lachnohyllum methyl ester                --           --
[C.sub.15][H.sub.24]O (3), hotrienol       --          1.0
  structure
Cadina-1,4-diene                           --           --
Elemol                                     --           tr
NI (4), hotrienol structure,               tr          0.4
  acetate?
NI (5), farnesene epoxide?                 --           --
NI (6), isocaryophyllene oxide?            --           --
Dehydromatricaria ester *                  --           --
(E)-Nerolidol                             0.3          0.7
Dendrolasin                                tr          0.7
Lauric acid                                --           --
Spatulenol#                               2.4#         1.4
Geranyl butanoate                          --          0.2
Caryophyllene oxide#                      0.1          1.2
Matricaria lactone *                       --           --
Dihydronerolidol                          0.2          0.3
Humulene-1,2-epoxide                       --           --
trans-a-Bisabolene epoxide                 --           --
NI (7), benzenemethanol,                   --           --
  [alpha]-1-octenyl-?
Viridiflorol                               tr           tr
NI (8)                                    0.1          0.7
NI (9), sesquiterpene acetate              --           --
Geranyl isovalerate#                      0.3         22.9#
Cubenol                                   0.1           --
(Z)-[alpha]-Bergamotol                     --           --
NI (10)                                    --           --
NI (11), dendrolasin isomer *              --          1.7
[C.sub.15][H.sub.24]O (12),                --          0.3
  nerolidol structure
[gamma]-Eudesmol#                         0.3          0.2
[gamma]-Cadinol#                          0.2           --
T-Muurolol#                                --          0.5
NI (13)                                    --           --
[C.sub.15][H.sub.24]O (14),                --           --
  chamomillol
Bisabolol oxide B#                        9.9#         0.2
[alpha]-Eudesmol#                         0.2           --
Alloaromadendrene epoxide                  tr           tr
Hexadecahydrocyclobuta[1,2:3,4]            --          0.2
  di-cyclooctene
Bisabolone oxide A#                      13.9#         0.6
[alpha]-Bisabolol#                        5.6#         0.1
cis-[alpha]-Bisabolene epoxide#            --           --
(Z)-Lancelol ([beta]-                      --           --
  bisabolen-12-ol)
Dimethylpentadecane                        --           --
Aromadendrene oxide 2                      --          1.2
Geranyl tiglate                           0.5           --
n-Pentadecanal                             --           --
Chamazulene#                              4.7#         0.5
Citronellyl hexanoate                      --           --
Bisabolol oxide A#                       39.4#         0.1
Benzyl benzoate                            --           --
Myristic acid                              --           --
NI (15) MW236                              --           tr
NI (16) MW234                              --          0.5
n-Octadecane                              0.2           --
NI (17) MW232, benzenemethanol,            --          0.6
  [alpha]-1-decenyl-
NI (18)                                    --           --
NI (19), indene structure                  --           --
Farnesyl acetate                           --          0.2
Hexahydrofarnesyl acetone                 0.1          0.5
NI (20), [C.sub.17][H.sub.16]              --           --
  [O.sub.2], ester
(Z)-En-yne-dicydoether#, MW200           11.5#        37.2#
NI (21)#, indene structure?                --           --
(E)-En-yne-dicycloether, MW200            0.4          0.8
n-Nonadecane                              0.2          0.4
NI (22)                                    --           --
(Z)-En-yne-dicycloether, MW214            0.4          0.3
Palmitic acid                              tr           tr
n-Eicosane                                0.1          0.2
13-Hexyloxacyclotridec-10-ene-2-one,       --           tr
  MW280
[C.sub.15][H.sub.14][O.sub.2] (23),        --           --
  benzhydryl acetate?
[gamma]-Palmitolactone                    0.1          0.3
cis-Linoleic acid                         0.1           --
9,12-octadecadien-1-ol, (Z,Z)-             --           --
n-Tricosane                               0.1          0.2
n-Pentacosane                             0.7           tr

GROUPS OF COMPONENTS
Monoterpenes                              0.9          3.6
Oxygenated monoterpenes                   1.5          23.2
Sesquiterpenes                            3.1          16.8
Oxygenated sesquiterpenes                73.4#         12.7
Polyacetylenes                            12.3        38.3#
Aliphatic acid and esters                 0.7          0.8
Other compounds                           6.6          2.0
Not identified                            0.1          1.8
  Total                                   98.6         99.2
  Oil volume, %                           0.15         0.12

Compound                               Percentage composition

                                       Anthemis    Matricaria
                                       tinctoria   perforata

[alpha]-Pinene                            0.1          --
Sabinene                                  0.9          --
[beta]-Pinene#                           1.8#          --
6-Methyl-5-hepten-2-one                   tr           tr
Myrcene#                                  0.2          --
2-Pentylfuran                             0.2          tr
n-Octanal                                 0.1          --
[alpha]-Terpinene                         0.2          --
p-Cymene                                  0.3          --
Limonene                                  0.4          --
1,8-Cineol#                              3.6#          --
(E)-[beta]-Ocimene                        --           tr
[gamma]-Terpinene                         0.5          --
Artemisia ketone                          --           tr
cis-Limonene hydrate                      0.1          --
Terpinolene                               0.1          --
Perillene                                 --           --
2-Methylbutyl 2-methylbutyrate            0.3          tr
n-Nonanal                                 0.4          --
Isoamyl isovalerate                       0.1          tr
1-Octenyl acetate                         --           --
n-Pentyl isovalerate                      0.2          tr
Pinocarvone                               0.1          tr
Octanoic acid                             tr           --
Terpinen-4-ol                             0.5          --
p-Cymen-8-ol                              0.2          --
[alpha]-Terpineol                         1.8          --
cis-3-Hexenyl isovalerate                 tr           tr
Nonanoic acid                             1.1          --
n-Undecanal                               0.5          --
(E)-Carvyl acetate                        0.1          --
[delta]-Elemene                           0.2          --
2H-2,4a-Ethanonaphthalene,                --          0.1
  1,3,4,5,6,7-hexa-hydro-
  2,5,5-trimethyl-
(E,E)-2,4-Decadienal                      tr           --
[alpha]-Cubebene                          0.2          --
[alpha]-Copaene                           1.3          --
Isoeugenol                                --          0.1
Geranyl acetate                           --           --
(Z)-Jasmone                               tr           --
Decanoic acid#                           3.6#         0.3
(E)-[beta]-Caryophyllene                  0.6         0.2
Aromadendrene                             0.1         0.1
[beta]-Gurjunene                          tr           --
[alpha]-Humulene                          0.4          tr
Geranyl acetone                           0.1          --
(E)-[beta]-Farnesene#                    3.3#         3.5#
8-Methylcoumarin                          --          0.9
Alloaromadendrene                         tr           --
Germacrene D                              0.5         0.1
[alpha]-Amorphene                         0.4          tr
[alpha]-Muurolene                         1.2          --
Geranyl isobutanoate                      --           tr
Isopentyl phenyl acetate                  2.1          --
Bicyclogermacrene                         0.2          tr
[C.sub.15][H.sub.24] (1)                  --           --
n-Undecanoic acid                         1.0          --
n-Tridecanal                              0.3          --
Z-Lachnohyllum methyl ester#              --          2.9#
Isofaurinone                              0.4          --
[delta]-Cadinene#                        2.2#          --
[C.sub.15][H.sub.26]O (2)#               3.2#          --
Matricaria ester *#                       --          3.5#
(ZZ)-Matricaria ester#                    --         77.9#
[gamma]-Cadinene#                        4.0#          --
E-Lachnohyllum methyl ester               --          0.1
[C.sub.15][H.sub.24]O (3), hotrienol      --           --
  structure
Cadina-1,4-diene                          0.2          --
Elemol                                    0.2          --
NI (4), hotrienol structure,              0.1          --
  acetate?
NI (5), farnesene epoxide?                --          0.3
NI (6), isocaryophyllene oxide?           --           --
Dehydromatricaria ester *                 --          1.1
(E)-Nerolidol                             0.9          --
Dendrolasin                               --           --
Lauric acid                               tr           --
Spatulenol#                              2.3#         0.5
Geranyl butanoate                         --           --
Caryophyllene oxide#                      1.3         0.4
Matricaria lactone *                      --          3.0#
Dihydronerolidol                          --           --
Humulene-1,2-epoxide                      --           --
trans-a-Bisabolene epoxide                0.3         0.1
NI (7), benzenemethanol,                  --           --
  [alpha]-1-octenyl-?
Viridiflorol                              0.5         0.1
NI (8)                                    --          0.3
NI (9), sesquiterpene acetate            4.6#          --
Geranyl isovalerate#                      0.1         0.1
Cubenol                                   1.0          --
(Z)-[alpha]-Bergamotol                    --          0.1
NI (10)                                   --          0.7
NI (11), dendrolasin isomer *             --           --
[C.sub.15][H.sub.24]O (12),               --           --
  nerolidol structure
[gamma]-Eudesmol#                         1.4         0.2
[gamma]-Cadinol#                         8.7#         0.2
T-Muurolol#                              4.0#          --
NI (13)                                   --           --
[C.sub.15][H.sub.24]O (14),               --          0.4
  chamomillol
Bisabolol oxide B#                        --          0.1
[alpha]-Eudesmol#                        10.2#         --
Alloaromadendrene epoxide                 1.2         0.1
Hexadecahydrocyclobuta[1,2:3,4]           tr           --
  di-cyclooctene
Bisabolone oxide A#                       --           tr
[alpha]-Bisabolol#                        0.3          --
cis-[alpha]-Bisabolene epoxide#          2.6#          --
(Z)-Lancelol ([beta]-                     --          0.1
  bisabolen-12-ol)
Dimethylpentadecane                       --           --
Aromadendrene oxide 2                     2.4         0.7
Geranyl tiglate                           --           --
n-Pentadecanal                            0.2          --
Chamazulene#                              --           --
Citronellyl hexanoate                     2.0          --
Bisabolol oxide A#                        0.1          tr
Benzyl benzoate                           tr          0.1
Myristic acid                             0.4          --
NI (15) MW236                             0.3          --
NI (16) MW234                             tr           tr
n-Octadecane                              --          0.3
NI (17) MW232, benzenemethanol,           0.5          --
  [alpha]-1-decenyl-
NI (18)                                  4.2#          --
NI (19), indene structure                 --           --
Farnesyl acetate                          tr           tr
Hexahydrofarnesyl acetone                 0.4         0.1
NI (20), [C.sub.17][H.sub.16]             --           --
  [O.sub.2], ester
(Z)-En-yne-dicydoether#, MW200            0.1         0.1
NI (21)#, indene structure?               --           --
(E)-En-yne-dicycloether, MW200            --           --
n-Nonadecane                              0.4         0.2
NI (22)                                   --           --
(Z)-En-yne-dicycloether, MW214            --           --
Palmitic acid                             1.5          --
n-Eicosane                                0.2         0.1
13-Hexyloxacyclotridec-10-ene-2-one,      --           --
  MW280
[C.sub.15][H.sub.14][O.sub.2] (23),       --           --
  benzhydryl acetate?
[gamma]-Palmitolactone                    0.2         0.1
cis-Linoleic acid                         0.1         0.1
9,12-octadecadien-1-ol, (Z,Z)-            0.2          --
n-Tricosane                               1.2         0.1
n-Pentacosane                             1.4          tr

GROUPS OF COMPONENTS
Monoterpenes                              4.5          tr
Oxygenated monoterpenes                   8.6         0.2
Sesquiterpenes                           14.8         4.0
Oxygenated sesquiterpenes                46.1         3.0
Polyacetylenes                            0.1        88.6#
Aliphatic acid and esters                 8.3         0.4
Other compounds                           7.4         1.8
Not identified                            5.0         1.4
  Total                                  94.8         99.4
  Oil volume, %                           tr          0.2

                                        Percentage
Compound                               composition

                                       Leucanthemum   Indentification
                                         vulgare          method

[alpha]-Pinene                              --             1,2,3
Sabinene                                    tr             1,2,3
[beta]-Pinene#                              --             1,2,3
6-Methyl-5-hepten-2-one                     --             1,2,3
Myrcene#                                   0.2             1,2,3
2-Pentylfuran                               --             1,2,3
n-Octanal                                   tr             1,2,3
[alpha]-Terpinene                           --             1,2,3
p-Cymene                                   0.1             1,2,3
Limonene                                    tr             1,2,3
1,8-Cineol#                                0.4             1,2,3
(E)-[beta]-Ocimene                          tr             1,2,3
[gamma]-Terpinene                           --             1,2,3
Artemisia ketone                            --              1,2
cis-Limonene hydrate                        --             1,2,3
Terpinolene                                 --             1,2,3
Perillene                                   --             1,2,3
2-Methylbutyl 2-methylbutyrate             0.1             1,2,3
n-Nonanal                                  0.2             1,2,3
Isoamyl isovalerate                        0.2             1,2,3
1-Octenyl acetate                          1.1             1,2,3
n-Pentyl isovalerate                       0.4             1,2,3
Pinocarvone                                 --             1,2,3
Octanoic acid                              0.2             1,2,3
Terpinen-4-ol                               tr             1,2,3
p-Cymen-8-ol                                --              1,2
[alpha]-Terpineol                           tr             1,2,3
cis-3-Hexenyl isovalerate                   --             1,2,3
Nonanoic acid                              0.1             1,2.3
n-Undecanal                                 tr             1,2,3
(E)-Carvyl acetate                          --             1,2,3
[delta]-Elemene                             --              1,2
2H-2,4a-Ethanonaphthalene,                  --             1,2,3
  1,3,4,5,6,7-hexa-hydro-
  2,5,5-trimethyl-
(E,E)-2,4-Decadienal                       0.1             1,2,3
[alpha]-Cubebene                           0.1             1,2,3
[alpha]-Copaene                             tr             1,2,3
Isoeugenol                                  --             1,2,3
Geranyl acetate                            0.8             1,2,3
(Z)-Jasmone                                 --             1,2,3
Decanoic acid#                             4.9#            1,2,3
(E)-[beta]-Caryophyllene                   1.3             1,2,3
Aromadendrene                               tr             1,2,3
[beta]-Gurjunene                            --             1,2,3
[alpha]-Humulene                           0.1             1,2,3
Geranyl acetone                             --             1,2,3
(E)-[beta]-Farnesene#                      7.3#            1,2,3
8-Methylcoumarin                            --             1,2,3
Alloaromadendrene                           --             1,2,3
Germacrene D                               0.1             1,2,3
[alpha]-Amorphene                           tr             1,2,3
[alpha]-Muurolene                           tr             1,2,3
Geranyl isobutanoate                        tr             1,2,3
Isopentyl phenyl acetate                    --              1,3
Bicyclogermacrene                           --              1,2
[C.sub.15][H.sub.24] (1)                   0.2             1,2,3
n-Undecanoic acid                          0.8              1,2
n-Tridecanal                               1.2             1,2,3
Z-Lachnohyllum methyl ester#                --             1,2,3
Isofaurinone                               0.5              1,2
[delta]-Cadinene#                          0.1             1,2,3
[C.sub.15][H.sub.26]O (2)#                  --             1,2,3
Matricaria ester *#                         --             1,2,3
(ZZ)-Matricaria ester#                      --             1,2,3
[gamma]-Cadinene#                           tr             1,2,3
E-Lachnohyllum methyl ester                 --              1,3
[C.sub.15][H.sub.24]O (3), hotrienol        --             1,2,3
  structure
Cadina-1,4-diene                            --             1,2,3
Elemol                                     0.2             1,2,3
NI (4), hotrienol structure,                --             1,2,3
  acetate?
NI (5), farnesene epoxide?                  --              1,3
NI (6), isocaryophyllene oxide?            0.5              1,3
Dehydromatricaria ester *                   --             1,2,3
(E)-Nerolidol                               --             1,2,3
Dendrolasin                                 --              1,3
Lauric acid                                2.0             1,2,3
Spatulenol#                                 --             1,2,3
Geranyl butanoate                           --             1,2,3
Caryophyllene oxide#                       5.0#            1,2,3
Matricaria lactone *                        --             1,2,3
Dihydronerolidol                            --             1,2,3
Humulene-1,2-epoxide                       0.5              1,3
trans-a-Bisabolene epoxide                  --             1,2,3
NI (7), benzenemethanol,                  18.4#            1,2,3
  [alpha]-1-octenyl-?
Viridiflorol                                --             1,2,3
NI (8)                                      --             1,2,3
NI (9), sesquiterpene acetate               --             1,2,3
Geranyl isovalerate#                       1.1             1,2,3
Cubenol                                     --             1,2,3
(Z)-[alpha]-Bergamotol                      --             1,2,3
NI (10)                                    5.7#            1,2,3
NI (11), dendrolasin isomer *               --             1,2,3
[C.sub.15][H.sub.24]O (12),                 --             1,2,3
  nerolidol structure
[gamma]-Eudesmol#                          4.5#            1,2,3
[gamma]-Cadinol#                            tr             1,2,3
T-Muurolol#                                 --             1,2,3
NI (13)                                    2.9#            1,2,3
[C.sub.15][H.sub.24]O (14),                 --             1,2,3
  chamomillol
Bisabolol oxide B#                          --             1,2,3
[alpha]-Eudesmol#                           --             1,2,3
Alloaromadendrene epoxide                   --             1,2,3
Hexadecahydrocyclobuta[1,2:3,4]            5.3#            1,2,3
  di-cyclooctene
Bisabolone oxide A#                         --             1,2,3
[alpha]-Bisabolol#                          --              1,2
cis-[alpha]-Bisabolene epoxide#             --             1,2,3
(Z)-Lancelol ([beta]-                      0.5              1,3
  bisabolen-12-ol)
Dimethylpentadecane                        2.2             1,2,3
Aromadendrene oxide 2                       --              1,3
Geranyl tiglate                             --             1,2,3
n-Pentadecanal                             0.2             1,2,3
Chamazulene#                                tr              1,2
Citronellyl hexanoate                       --             1,2,3
Bisabolol oxide A#                         0.4             1,2,3
Benzyl benzoate                             --             1,2,3
Myristic acid                              0.1             1,2,3
NI (15) MW236                               --              1,3
NI (16) MW234                               --              1,3
n-Octadecane                                --              1,2
NI (17) MW232, benzenemethanol,            0.8              1,3
  [alpha]-1-decenyl-
NI (18)                                     --             1,2,3
NI (19), indene structure                  1.3              1,3
Farnesyl acetate                            --             1,2,3
Hexahydrofarnesyl acetone                  0.2             1,2,3
NI (20), [C.sub.17][H.sub.16]              9.8#            1,2,3
  [O.sub.2], ester
(Z)-En-yne-dicydoether#, MW200             0.5              1,3
NI (21)#, indene structure?                3.9#            1,2,3
(E)-En-yne-dicycloether, MW200              --              1,3
n-Nonadecane                               0.5             1,2,3
NI (22)                                    1.1             1,2,3
(Z)-En-yne-dicycloether, MW214              --              1,3
Palmitic acid                              1.7             1,2,3
n-Eicosane                                 0.1             1,2,3
13-Hexyloxacyclotridec-10-ene-2-one,       0.6             1,2,3
  MW280
[C.sub.15][H.sub.14][O.sub.2] (23),        0.5             1,2,3
  benzhydryl acetate?
[gamma]-Palmitolactone                     0.2              1,3
cis-Linoleic acid                          0.4              1,3
9,12-octadecadien-1-ol, (Z,Z)-              --              1,3
n-Tricosane                                0.2             1,2,3
n-Pentacosane                              1.7             1,2,3

GROUPS OF COMPONENTS
Monoterpenes                               0.3
Oxygenated monoterpenes                    2.3
Sesquiterpenes                             9.2
Oxygenated sesquiterpenes                  12.3
Polyacetylenes                             0.5
Aliphatic acid and esters                 12.0#
Other compounds                            12.5
Not identified                            44.4#
  Total                                    93.5
  Oil volume, %                            0.03

NI, not identified; * isomer not identified; tr, traces
(< 0.05%),--not found.

Note: The main components are indicated in bold is indicated with #.

Table 2. Mass spectral data of unidentified compounds

No.   [RI.sub.SPB-5]   MW    m/z (relative intensity)

1     1490             204   43(100), 118(60), 89(50), 136(25),
                             63(22), 90(20)

2     1516             222   43(100), 105(80), 41(60), 207(57),
                             161(55), 119(45), 91(40), 93(40),
                             79(38), 81(38), 55(35)

3     1529             220   71(100), 82(40), 43(35), 41(30), 107(20)

4     1552                   43(100), 41(80), 71(80), 69(50), 79(45),
                             55(35), 93(35)

5     1554                   43(100), 93(75), 120(48), 41(40),
                             79(40), 81(40)

6     1563                   41(100), 96(98), 79(95), 83(78), 82(72),
                             67(62), 69(60), 109(60)

7     1595                   43(100), 115(75), 128(58), 130(55),
                             147(53), 77(35), 129(35), 91(30)

8     1600             220   123(100), 81(70), 41(45), 69(30), 93(20)

9     1600             220   43(100), 177(50), 41(35), 91(30),
                             79(25), 107(25), 93(20)

10    1619                   172(100), 101(88), 87(80), 86(45),
                             63(43), 144(40), 141(38), 115(36),
                             113(30)

11    1622                   69(100), 41(70), 81(23), 67(17), 55(15)

12    1628             220   71(100), 69(65), 107(58), 43(55),
                             41(50), 94(30)

13    1641                   43(100), 117(28), 115(25), 145(20)

14    1641             220   54(100), 82(40), 41(25), 67(25), 55(25)

15    1775             236   81(100), 41(90), 43(70), 55(55), 69(52),
                             95(45), 105(40), 123(30), 147(30)

16    1787             234   117(100), 57(60), 41(58), 91(52),
                             149(50), 77(35)

17    1800             232   115(100), 130(90), 57(82), 128(68),
                             129(65), 41(55), 147(50), 77(45)

18    1807             220   41(100), 55(85), 81(82), 79(70), 93(68),
                             110(57), 95(55), 43(45), 67(42),
                             197(42), 91(40)

19    1826                   81(100), 41(50), 55(47), 147(45),
                             93(43), 123(37), 69(35)

20    1849             252   84(100), 95(95), 138(85), 94(60),
                             41(52), 55(45), 67(42), 109(42)

21    1870                   128(100), 115(60), 129(52), 41(45),
                             141(40), 143(40), 91(35), 77(30)

22    1914                   115(100), 41(65), 141(35), 167(30)

23    2063             226   165(100), 43(98), 166(50), 183(35),
                             152(25)

MW--molecular weight.
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Title Annotation:CHEMISTRY
Author:Raal, Ain; Kaur, Helen; Orav, Anne; Arak, Elmar; Kailas, Tiiu; Muurisepp, Mati
Publication:Proceedings of the Estonian Academy of Sciences
Article Type:Report
Geographic Code:4EXES
Date:Mar 1, 2011
Words:6589
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