Essential oil composition of Anthemis triumfetti (L.) DC

ESSENTIAL OIL OF ANTHEMIS TRIUMFETTI 297

Copyright © 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 297–299

FLAVOUR AND FRAGRANCE JOURNALFlavour Fragr. J. 2006; 21: 297–299Published online 8 November 2005 in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1592

Essential oil composition of Anthemis triumfetti (L.) DC.

Milica Pavlovi0,1 Nada Kovaçevi0,1* Olga Tzakou2 and Maria Couladis2

1 Department of Pharmacognosy, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade,Serbia and Montenegro

2 Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens,Panepistimiopolis, 157 71 Athens, Greece

Received 13 February 2004; Revised 1 December 2004; Accepted 11 January 2005

ABSTRACT: The essential oil of the aerial parts of Anthemis triumfetti (Asteraceae), obtained by hydrodistillation,

was analysed by GC and GC–MS; 64 compounds were identified, representing 98.3% of the oil. The major constitu-

ents were βββββ-pinene (16.9%), camphor (15.0%), ααααα-pinene (14.4%) and 1,8-cineole (5.8%). Copyright © 2005 John Wiley

& Sons, Ltd.

KEY WORDS: Anthemis triumfetti; Asteraceae; essential oil composition; β-pinene; camphor; α-pinene

* Correspondence to: N. Kovacevib, Department of Pharmacognosy, Faculty

of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade,

Serbia and Montenegro.

E-mail: [email protected]

Contract/grant sponsor: Ministry for Science, Technologies and Develop-

ment, Serbia.

Introduction

The genus Anthemis comprises about 100 species

distributed in Mediterranean region, nine of which

are found in flora of Serbia and Montenegro.1 Anthemis

triumfetti (L.) DC. [syn.: Cota triumfetti (L.) Gay] is a

perennial herb, 30–90 cm high, growing in woods

and rocky places on mountains.2 In previous phyto-

chemical studies sesquiterpene lactones, flavonoids and

acetylenes have been identified as the main constituens

in genus Anthemis.3–7 The essential oil composition

of some Anthemis species have been reported in the

literature.8–13 However, chemical composition of the

essential oil of A. triumfetti has not been the subject of

previous studies.

Material and Methods

Plant Material and Isolation of the Essential Oil

The aerial parts of A. triumfetti were collected at the

mountain Bjelasica in Montenegro, during the flowering

period, in July 2003. Voucher specimens are deposited in

the Institute of Botany and Botanical Garden, Faculty of

Biology, University of Belgrade (Herbarium BEOU; No.

17723). Semi-crushed air-dried plant material (50 g in

500 ml water) was subjected to hydrodistillation for 3 h,

using a modified Clevenger-type apparatus. The oil was

dried over anhydrous sodium sulphate and kept at −4 °C

until it was analysed.

Gas Chromatography

GC analysis was carried out using a SRI 8610C GC-FID

system, equipped with DB-5 capillary column (30 m ×0.32 mm; film thickness 0.25 µm) and connected to

a FID detector. The injector and detector temperature

was 280 °C. The carrier gas was He, at flow rate of

1.2 ml/min. The thermal program was 60 °C to 280 °C at

a rate of 3 °C/min. Two replicates of the sample were

processed in the same way.

Gas Chromatography–Mass Spectrometry

GC–MS analysis was performed on a Hewlett-Packard

6890-5973 GC–MS system operating in the EI mode

at 70 eV, equipped with a split/splitless injector (200 °C).

The transfer line temperature was 250 °C. Helium was

used as carrier gas (1 ml/min) and the capillary column

used was HP 5MS (30 m × 0.25 mm; film thickness

0.25 µm). The temperature programme was the same

with that used for the GC analysis; split ratio, 1:10. The

injected volume was 1.0 µl (10% pentane solution of

the oil).

Identification of Components

The identification of the compounds was based on

comparison of their retention indices (RI), their retention

times (RT) and mass spectra with those obtained from

authentic samples and/or the NIST/NBS, Wiley libraries

298 M. PAVLOVID ET AL.


and literature.14 The linear retention indices (RI) were

determined in relation to a homologous series of n-

alkanes (C9–C23) under the same operating conditions.15

Results and Discussion

The aerial parts of A. triumfetti yielded 0.4% (v/w) of

a yellow oil with a characteristic pleasant odour.

The chemical composition of the oil is summarized

in Table 1; 64 components were identified amounting

to 98.3% of the total oil. The oil was characterized

by high percentage of monoterpene hydrocarbons

(40.3%), followed by oxygenated monoterpenes (35.7%).

Sesquiterpene hydrocarbons and oxygenated sesqui-

terpenes represented 14.3% and 4.5% of the oil, respect-

ively. The main compounds were β-pinene (16.9%),

camphor (15.0%), α-pinene (14.4%) and 1,8-cineole

(5.8%). Irregular monoterpenoids with chrysanthenyl

skeleton were identified in the essential oil: cis-

chrysanthenol (4.6%) and cis-chrysanthenyl acetate

(3.5%). Previous investigations on the essential oils of

A. carpatica and A. montana, originated from southern

Serbia, have found high concentrations of α-thujone

(40.2% and 46.9%, respectively), β-thujone (13.3% and

16.0%, respectively) and the irregular monoterpenes

yomogi alcohol (18.5%) in the oil of A. carpatica

and trans-chrysanthenyl acetate (11.3%) in the oil of

A. montana.8,9 The essential oil from A. melampodina, of

Egyptian origin, was characterized by the presence

of the irregular monoterpene santolinatriene (27.33%),

sabinene (6.09%) and β-pinene (6.44%).10 The irregular

monoterpenes of the chrysanthenyl, artemisyl and santo-

linyl series are genetically related and only reported in

the tribe Anthemideae.16

Esters of angelic acid, metacrylic acid and isobutyric

acid, which are the main constituents of A. nobilis essen-

tial oil, were not found in A. triumfetti oil.11–13

Table 1. Composition of the essential oil of Anthemis triumfetti

No. Components RI % Identification

1. (E)-2-Hexenal — t MS

2. Tricyclene 900 t MS

3. α-Thujene 904 t MS

4. α-Pinene 913 14.4 MS, Co–GC

5. Camphene 928 2.5 MS, Co–GC

6. Benzaldehyde 945 t MS

7. Sabinene 952 t MS

8. β-Pinene 957 16.9 MS, Co–GC

9. 6-Methyl-5-hepten-2-one 965 1.4 MS

10. 2-Pentyl furan 970 2.1 MS

11. n-Octanal 981 t MS

12. α-Terpinene 995 1.7 MS

13. p-Cymene 1003 1.7 MS, Co–GC

14. Limonene 1007 t MS, Co–GC

15. 1,8-Cineole 1009 5.8 MS, Co–GC

16. (Z)-β-Ocimene 1017 t MS

17. (E)-β-Ocimene 1027 0.7 MS

18. γ-Terpinene 1038 2.4 MS, Co–GC

19. cis-Sabinene hydrate 1047 t MS

20. Terpinolene 1067 t MS

21. Linalool 1079 t MS, Co–GC

22. cis-p-Menth-2-en-1-ol 1098 t MS

23. α-Campholenal 1104 t MS

24. trans-Chrysanthenol 1114 t MS

25. cis-Sabinol 1118 t MS

26. Camphor 1125 15.0 MS, Co–GC

27. cis-Chrysanthenol 1144 4.6 MS

28. Borneol 1146 1.8 MS, Co–GC

29. Terpinen-4-ol 1157 3.9 MS, Co–GC

30. α-Terpineol 1170 1.1 MS, Co–GC

31. Safranal 1178 t MS

32. n-Decanal 1185 t MS

33. trans-Piperitol 1186 t MS

34. cis-Chrysanthenyl acetate 1239 3.5 MS

35. Isobornyl acetate 1262 t MS

36. Thymol 1280 t MS

37. 7-epi-Silphiperfol-5-ene 1314 t MS

38. α-Cubebene 1323 t MS

39. α-Ylangene 1349 1.0 MS

40. β-Bourbonene 1358 1.4 MS

41. β-Elemene 1366 t MS

42. α-Gurjunene 1381 t MS

ESSENTIAL OIL OF ANTHEMIS TRIUMFETTI 299


Table 1. (Continued )

No. Components RI % Identification

43. (E)-Caryophyllene 1390 4.2 MS, Co–GC

44. β-Gurjunene 1398 t MS

45. α-Guaiene 1409 t MS

46. Aromadendrene 1414 t MS

47. α-Humulene 1424 1.6 MS

48. γ-Muurolene 1449 t MS

49. Germacrene D 1453 2.0 MS

50. Bicyclogermacrene 1467 1.1 MS

51. α-Muurolene 1472 t MS, Co–GC

52. γ-Cadinene 1484 0.6 MS

53. δ-Cadinene 1493 2.4 MS, Co–GC

54. α-Cadinene 1505 t MS

55. α-Calacorene 1513 t MS

56. Spathulenol 1548 1.3 MS, Co–GC

57. Caryophyllene oxide 1552 2.2 MS, Co–GC

58. Salvial-4(14)-en-1-one 1563 t MS

59. Humulene epoxide II 1577 t MS

60. 1-epi-Cubenol 1596 t MS

61. epi-α-Cadinol 1608 t MS

62. α-Muurolol 1615 t MS

63. α-Cadinol 1624 1.0 MS

64. Oplopanone 1707 t MS

Total 98.3

Grouped components

Monoterpene hydrocarbons 40.3

Oxygenated monoterpenes 35.7

Sesquiterpene hydrocarbons 14.3

Oxygenated sesquiterpenes 4.5

Others 3.5

RI, retention indices relative to C9–C24 n-alkanes on the HP 5MS.15

MS, identification based on comparison of mass spectra.

Co–GC, comparison with authentic compounds.

t, trace (<0.1%).

Acknowledgements—This study is a part of research withinProject No. 1568, financially supported by the Ministry for Science,Technologies and Development of Serbia.

References

1. Gajib M. Anthemis L. In Flora Srbije, Josifovic M (ed.). SANU:Belgrade, 1974; 83.

2. Fernandes R. Anthemis L. In Flora Europaea, vol 4, Tutin TG,Heywood VH, Burges NA et al. (eds). Cambridge UniversityPress: Cambridge, 1976; 145.

3. Wichtl M. Teedrogen und Phytopharmaka, Ein Handbuch für die

Praxis auf wissenschaftlicher Grundlage. WissenschaftlicheVerlagsgesellschaft mbH: Stuttgart, 2002; 127.

4. Bruno M, Rosseli S, Blondi ML, Gedris TE, Herz W. Biochem.

Syst. Ecol. 2002; 30: 891–895.

5. Vajs V, Todorovib N, Bulatovib V et al. Phytochemistry 2000; 54:625–633.

6. Williams CA, Greenham J, Harborne JB. Biochem. Syst. Ecol.2001; 29: 929–945.

7. Christensen LP. Phytochemistry 1992; 31: 7–49.8. Bulatovib V, Menkovib N, Vajs V, Milosavljevib S, Djokovib D.

J. Essent. Oil Res. 1997; 9: 397–400.9. Bulatovib V, Menkovib N, Vajs V, Milosavljevib S, Djokovib D.

J. Essent. Oil Res. 1998; 10: 223–226.10. Grace MH. Phytother. Res. 2002; 16: 183–185.11. Bassols F, Thomas AF. J. Essent. Oil Res. 1991; 3: 309–312.12. Klimes I, Lamparsky D, Scholz E. Helv. Chim. Acta 1981; 64:

2338–2349.13. Thomas AF. Helv. Chim. Acta 1981; 64: 2397–2440.14. Adams RP. Identification of Essential Oil Components by Gas

Chromatography/Quadrupole Mass Spectrometry. Allured: CarolStream, IL, 2001.

15. Van den Dool H, Kratz PD. J. Chromatogr. 1963; 11: 463–471.16. Epstein WW, Poulter CD. Phytochemistry 1973; 12: 737–747.

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Essential oil composition of Anthemis triumfetti (L.) DC