FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 191–194

DOI: 10.1002/ffj.976

Composition of the essential oils of Tanacetum spp. from

Turkey†
Nezhun Gören,1 Betül Demirci2 and K. Hüsnü Can Başer2 *
1 Department of Biology, Faculty of Science and Arts, Yildiz Technical University, 80750-Istanbul, Turkey
2 Medicinal and Aromatic Plant and Drug Research Centre (TBAM) Anadolu University, 26470-Eskişehir, Turkey
Received 22 June 2000
Revised 8 November 2000
Accepted 15 November 2000

ABSTRACT: Water-distilled essential oil of leaves and flowers of Tanacetum argyrophyllum (C. Koch) Tvzel. var.
argyrophyllum and leaves of Tanacetum argenteum (Lam.) Willd. subsp. canum (C. Koch) Grierson var. canum,
herbal parts of Tanacetum praeteritum (Horwood) Heywood subsp. praeteritum and Tanacetum praeteritum
(Horwood) Heywood subsp. massicyticum Heywood (Compositae), endemic taxa, were analysed by GC–MS.
Sixty-eight, 51, 50, 47 and 72 compounds, representing 90%, 86%, 72%, 91%, 83% of the oils, respectively, were
identified. ˛-Thujone (52% and 63%) was the major constituent of Tanacetum argyrophyllum var. argyrophyllum
leaf and flower oils, respectively. Caryophyllene oxide (13%) and ˛-thujone (12%) were found as the main
constituents of the oil of Tanacetum argenteum subsp. canum var. canum. Borneol (28%), 1,8-cineole (12%)
and bornyl acetate (10%) were the major constituents of T. praeteritum subsp. praeteritum. In the oil of subsp.
massicyticum, ˛-thujone (51%) and ˇ-thujone (10%) were characterized as the main constituents. Copyright 
2001 John Wiley & Sons, Ltd.
KEY WORDS: Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum; Tanacetum argenteum (Lam.)
Willd. ssp. canum (C. Koch) Grierson var. canum; Tanacetum praeteritum (Horwood) Heywood subsp. prae-
teritum; Tanacetum praeteritum (Horwood) Heywood subsp. massicyticum Heywood; Compositae; essential oil
composition; ˛-thujone; caryophyllene oxide; ˇ-thujone; borneol; 1,8-cineole; bornyl acetate

Introduction argenteum,2 subsp. flabellifolium,3 subsp. canum var.

Members of the genus Tanacetum (Compositae) com-
prise several medicinally important taxa. This genus
is represented in Turkey by 44 species and altogether
59 taxa. Three varieties of T. argyrophyllum (C. Koch)
Tvzel. are known to occur in Turkey, viz. var. argy-
rophyllum, var. polycephalum (Schultz Bip.) Grierson
and var. subvirescens (DC) Grierson. In the flora of
Turkey, T. argenteum (Lam.) Willd. is classified into
three subspecies: argenteum, flabellifolium (Boiss. &
Heldr.) Grierson and canum. T. praeteritum (Horwood)
Heywood comprises two subspecies, both of them being
endemic in Turkey. T. praeteritum (Horwood) Heywood
subsp. praeteritum grows on rocks and limestone slopes
at altitudes of 1200–2000 m and T. praeteritum (Hor-
wood) Heywood subsp. massicyticum Heywood, grows
on limestone slopes at altitudes of 1600–2200 m.1
Sesquiterpene lactones were isolated from the aerial
parts of several subspecies of T. argenteum: subsp.
canum.4,5 Sesquiterpene lactones with antibacterial
activity were isolated from the aerial parts of
T. argyrophyllum var. argyrophyllum.6,7 Sesquiterpene
lactones and sesquiterpene esters,8 – 10 and flavonoids11
were previously isolated from the aerial parts of
T. praeteritum subsp. praeteritum.
This is the first report on the essential oils of
these taxa.
Experimental
Plant Materials
The air-dried plant materials, collection places and dates,
yields of essential oils are given in Table 1. Voucher
specimens have been deposited at the Herbarium of the
Faculty of Pharmacy, Istanbul University in Istanbul
(ISTE) and Herbarium of the Faculty of Pharmacy,
Anadolu University in Eskişehir (ESSE), in Turkey.

Isolation of the Essential Oils

*Correspondence to: K. H. C. Başer, Medicinal and Aromatic Plant
and Drug Research Centre (TBAM) Anadolu University, 26470-
Eskişehir, Turkey.
† Presented at the 28th International Symposium on Essential Oils, 1–3
September 1997, Eskişehir, Turkey.
Air-dried plant parts were subjected to hydrodistillation
for 3 h using a Clevenger-type apparatus to produce the
essential oils.

Copyright  2001 John Wiley & Sons, Ltd.

192 N. GÖREN, B. DEMIRCI AND K. H. C. BAŞER

Table 1. Plant materials used in this study

Tanacetum species
T. praeteritum
T. argyrophyllum T. argenteum
var. argyrophyllum subsp. canum var. canum subsp. praeteritum subsp. massicyticum
Code number A B C D E
Plant material Dried leaves Dried flowers Dried leaves Dried aerial parts Dried aerial parts
Collection year April 1994 July 1992 June 1995 June 1995
Collection place Gümüşhane: Kösedaǧi Adana: Gülektepe Muǧla: Fethiye Antalya: Elmali
Altitude 1550 m 1550 m 1500 m 1825 m
Yield (%) 1.03 0.96 0.04 1.09 0.92
Voucher number ISTE 72710 ISTE 64366 ESSE 11351 ESSE 11322

Identification of the Components
The oils were analysed by GC–MS using a Hewlett-
Packard GCD system. An HP-Innowax FSC column
(60 m ð 0.25 mm i.d., film thickness 0.25 µm) was
used, with helium as carrier gas (1 ml/min). GC oven
temperature was kept at 60 ° C for 10 min and pro-
grammed to 220 ° C at a rate of 4 ° C/min, then kept con-
stant at 220 ° C for 10 min, then programmed to 240 ° C at
a rate of 1 ° C/min. Alkanes were used as reference points
in the calculation of relative retention indices (RRI). The
split ratio was adjusted to 50 : 1. The injector temperature
was 250 ° C. MS were taken at 70 eV. Mass range was
35–425 m/z. A library search was carried out using the
Wiley GC–MS Library and the TBAM Library of Essen-
tial Oil Constituents. Relative percentage amounts were
calculated from TIC by the computer. The compounds
identified in the oil are listed in Table 2.

Table 2. Chemical compositions of Tanacetum species

RRI Compounds A (%) B (%) C (%) D (%) E (%)
947 cis-2-Isopropylhexa-1,4-diene — 0.2 — — 0.9
1014 Tricyclene — — — 0.1 —
1032 ˛-Pinene 1.4 1.4 0.4 1.3 0.4
1035 ˛-Thujene tr — — 0.2 0.1
1043 Santolinatriene 0.2 0.1 — — 0.1
1063 Ethyl 2-methylbutyrate — — — — tr
1076 Camphene 0.5 0.2 — 3.5 —
1093 Hexanal — — — — tr
1118 ˇ-Pinene 0.2 0.1 — 5.7 0.4
1132 Sabinene tr 0.1 — 0.4 4.4
1174 Myrcene — — — — 0.1
1188 ˛-Terpinene 0.1 0.1 — 0.7 0.2
1195 Heptanal — — — — tr
1195 Dehydro-1,8-cineole tr — — 0.1 0.1
1203 Limonene 0.1 — — 0.3 0.1
1212 Isoamylalcohol 0.1 — — — —
1213 1,8-Cineole 11.1 3.7 1.5 12.3 4.0
1218 ˇ-Phellandrene — — — — tr
1232 (E)-2-Hexenal — — — — 0.1
1244 Amyl furan — — — — tr
1255 -Terpinene 0.2 0.1 — 1.9 0.4
1280 p-Cymene 2.5 1.4 0.1 1.7 0.5
1285 Isoamyl isovalerate — 0.1 — — —
1290 Terpinolene — — — 0.3 0.1
1294 1,2,4-Trimethylbenzene 0.1 0.1 — — —
1299 2-Methylbutyl-3-methylbutyrate — tr — — —
1348 6-Methyl-5-hepten-2-one — — — 0.1 0.1
1355 1,2,3-Trimethylbenzene 0.1 — — — —
1358 Artemisia ketone 0.2 1.3 — — —
1400 Nonanal — — 0.1 — —
1403 Yomogi alcohol 0.6 0.9 — — —
1430 a-Thujone 51.8 62.8 11.9 — 51.1
1451 ˇ-Thujone 4.7 4.3 2.7 — 10.0
1474 trans-Sabinene hydrate 0.1 — 0.2 — 0.9
1482 Longipinene — — — — 0.3
1492 Cyclosativene — — — — tr
1497 ˛-Copaene — — 0.2 — —
1499 ˛-Campholenal 0.1 0.1 0.1 — —
1510 Artemisia alcohol 0.1 0.2 — — —

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 191–194
 ESSENTIAL OILS OF TANACETUM SPP. 193

Table 2. (continued)
RRI Compounds A (%) B (%) C (%) D (%) E (%)
1522 Chrysanthenone 0.3 0.3 — — —
1532 Camphor 2.6 2.2 2.5 2.4 0.2
1541 Benzaldehyde tr 0.2 — 0.1 0.2
1553 Linalool — — 1.4 — tr
1556 cis-Sabinenehydrate 0.1 — 0.2 3.1 0.7
1562 Isopinocamphone — — 0.5 — —
1568 1-Methyl-4-acetyl-cyclohex-1-ene — — — 0.2 0.5
1571 trans-p-Menth-2-en-1-ol 0.2 0.1 — 0.7 0.1
1586 Pinocarvone 0.3 0.2 0.3 0.6 0.1
1597 Bornyl acetate — — — 10.0 —
1611 Terpinen-4-ol 0.7 0.6 0.8 7.1 1.3
1612 ˇ-Caryophyllene — — 5.1 0.2 —
1624 trans-Dihydrocarvone 3.0 0.7 — — —
1628 4-Terpinenylacetate — — — 1.0 —
1638 cis-p-Menth-2-en-1-ol 0.2 0.1 — 0.4 —
1639 cis-p-Mentha-2,8-dien-1-ol — — — — 0.1
1641 Thuj-3-en-10-al — — — — 0.3
1643 Dehydro sabina ketone 0.1 — — — —
1645 cis-Isodihydrocarvone 0.4 0.1 — — —


1648 Myrtenal 0.1 0.1 1.2 0.1
1.0
1651 Sabina ketone 0.3 — — —
1658 Sabinylacetate 0.2 0.1 0.8 — 0.1
1658 Umbellulone — — — 0.4 —
1664 trans-Pinocarveol 0.6 0.5 1.6 0.5 0.1
1671 (E)-ˇ-Farnesene — — — — 0.1
1681 (Z)-3-Hexenyltiglate — — — — tr
1682 υ-Terpineol 0.1 — 0.2 0.2 0.1
1683 trans-Verbenol 0.1 0.1 0.8 — 0.1
1687 ˛-Humulene — — 1.3 — —
1689 trans-Piperitol tr — — 0.1 tr
1690 -Selinene — — — 0.1 —
1697 Carvotanacetone tr — — — —
1703 Salicylaldehyde — — — — tr
1706 ˛-Terpineol 0.1 0.1 2.3 1.7 0.3
1719 Borneol 0.7 0.2 — 28.1 —


1720 trans-Sabinol 0.9 0.2 — 1.0
2.6
1725 Verbenone tr — — —
1726 Germacrene-D — — — 0.4 0.6
1732 Neo-dihydrocarveol 0.4 — — — —
1742 ˇ-Selinene 0.1 — — — —
1751 Carvone 0.2 0.1 — — —
1755 Bicyclogermacrene 0.2 — — — 0.4
1758 cis-Piperitol 0.1 — — 0.2 tr
1764 cis-Chrysanthenol — — 0.1 — —
1773 υ-Cadinene — — 0.1 — —
1786 ar-Curcumene — — 0.5 — —
1802 Cumin aldehyde 0.2 0.1 — — 0.1
1804 Myrtenol 0.1 0.1 0.2 1.6 0.1
1811 trans-p-Mentha-1(7),8-dien-2-ol 0.1 — — — —
1815 p-Mentha-1,5-dien-7-ol — — — — 0.2
1823 p-Mentha-1(7),5-dien-2-ol — — — — tr
1845 trans-Carveol 0.2 0.1 — — —
1857 Geraniol — — — — tr
1864 p-Cymen-8-ol 0.1 — — 0.1 tr
1868 (E)-Geranyl acetone — — 0.1 — —
1896 cis-p-Mentha-1(7),8-dien-2-ol 0.1 — — — —
1981 2-Methoxy-4-methylphenol (D 4-Methylguaiacol ) — — — 0.1 —
2000 Isocaryophyllene oxide — — — — tr
2008 Caryophyllene oxide 0.1 — 12.6 0.4 0.6
2041 Pentadecanal — — 0.5 — —
2057 13-Tetradecanolide — — — — tr
2070 Cinnamaldehyde — — — 0.1 —
2071 Humulene epoxide-II — — 1.0 — —
2073 p-Mentha-1,4-dien-7-ol 0.1 — — — 0.1
2074 Caryophylla-2(12),6(13)-dien-5-one tr — 0.8 0.2 —
2113 Cumin alcohol 0.2 0.1 — — tr
2131 Hexahydrofarnesylacetone — tr 0.8 — —
2144 Spathulenol 0.1 0.2 1.2 — 0.3
2186 Eugenol 0.1 — — — 0.1
(continued overleaf )

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 191–194
194 N. GÖREN, B. DEMIRCI AND K. H. C. BAŞER

Table 2. (continued)
RRI Compounds A (%) B (%) C (%) D (%) E (%)
2187 T-Cadinol — — 1.0 — —
2198 Thymol — — 0.1 0.6 —
2209 T-Muurolol — — 1.8 — —
2232 ˛-Bisabolol — — 1.6 — 0.2
2239 Carvacrol 0.2 0.1 0.4 — —
2241 p-Isopropylphenol 0.1 — — — 0.1
2255 ˛-Cadinol — — 1.1 — —
2257 ˇ-Eudesmol 0.6 0.4 — — —
2260 15-Hexadecanolide 0.3 0.5 0.5 0.3 tr
2300 Decanoic acid — 0.2 — — —
2300 Tricosane — 0.3 — — —
2316 Caryophylla-2(12),6(13)-dien-5ˇ-ol (D Caryophylladienol-I) tr — 0.7 0.1 0.1
2324 Caryophylla-2(12),6(13)-dien-5˛-ol (D Caryophylladienol-II) 0.2 — 3.5 0.4 0.2
2365 (Z)-Methyl jasmonate — — — — 0.1
2384 Hexadecanol 0.1 — — 0.1 tr
2392 Caryophylla-2(12),6-dien-5ˇ-ol (D Caryophyllenol-II) — — 2.2 — —
2700 Heptacosane — — 0.2 — —
2900 Nonacosane — — 0.2 — —
2931 Hexadecanoic acid — 0.4 2.8 — —
Monoterpene hydrocarbons 62.5 72.8 15.1 16.1 6.8
Oxygenated monoterpenes 25.1 10.5 16.7 72.4 71.4
Sesquiterpene hydrocarbons 0.3 — 7.2 0.7 1.1
Oxygenated sesquiterpenes 1.0 0.6 27.5 1.1 1.4
Others 0.9 2.0 5.2 1.0 2.5
Total 89.7 85.9 71.7 91.3 83.0

A Tanacetum argyrophyllum var. argyrophyllum-leaf.

B Tanacetum argyrophyllum var. argyrophyllum-flower.
C Tanacetum argenteum subsp. canum var. canum-leaf.
D Tanacetum praeteritum ssp. praeteritum-aerial parts.
E Tanacetum praeteritum ssp. massicyticum-aerial parts.
RRI relative retention indices.
tr, trace <0.1%.

Results and Discussion
The results of analysis of the essential oils obtained
by water distillation are shown in Table 2. In the oils
of the leaves and flowers of Tanacetum argyrophyllum
(C. Koch) Tvzel. var. argyrophyllum, 68 and 51 com-
pounds, representing 90% and 86% of the oils, with
˛-thujone (52% and 63%), were characterized as the
main constituent. Fifty compounds representing 72% of
the oil of T. argenteum subsp. canum var. canum were
characterized with caryophyllene oxide (13%) and ˛-
thujone (12%) as the main constituents.
Thujane and camphane derivatives (particularly thu-
jones and camphor), together with 1,8-cineole, have
been reported as the main components in Tanace-
tum oils.12 Thujone-rich oils were previously reported
from T. argenteum,12 T. boreale,12 T. microphyllum,12
T. densum 13 and T. vulgare.12,14 Except for the oils of
T. argenteum and T. microphyllum, in all the other oils
ˇ-thujone was the main constituent. Our results provide
added proof for the oil of T. argenteum to be character-
ized by the predominance of ˛-thujone.
In the oil of T. praeteritum subsp. praeteritum, 47
compounds, representing 91% of the oil, were identi-
fied, with borneol (28%), 1,8-cineole (12%) and bornyl
acetate (10%) as the main constituents. Seventy-two
compounds, representing 83% of the oil, were charac-
terized in the oil of Tanacetum praeteritum subsp. mas-
sicyticum, with ˛-thujone (51%) and ˇ-thujone (10%) as
the main constituents. This is the first report on the essen-
tial oils of Tanacetum praeteritum. Highly diverse com-
position of the essential oils of the two subspecies may
call for more thorough taxonomical investigation into the
status of Tanacetum praeteritum subsp. massicyticum.
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Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 191–194