FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2000; 15: 43±44

Composition of the essential oil of Chaerophyllum

aksekiense A. Duran et Duman, a recently
described endemic from Turkey
È zek,1 B. Demirci,1 A. Duran2 and H. Duman2
K. H. C. BasËer,1* N. Tabanca,1 T. O
1Anadolu University, Medicinal and Aromatic Plant and Drug Research Centre (TBAM), 26470 EskisËehir, Turkey
2
Gazi University, Faculty of Science and Letters, Department of Biology, 06500 Ankara, Turkey

Received 26 July 1999

Revised 5 October 1999
Accepted 5 October 1999

ABSTRACT: The water-distilled essential oil from crushed fruits of Chaerophyllum aksekiense were analysed by
GC±MS. Sixty-seven components, representing 82.0% of the oil, were characterized. The major components
were heptacosane (10.1%), humulene epoxide II (7.8%), (E)-b-farnesene (6.2%), caryophyllene oxide (6.0%),
a-humulene (5.5%), terpinolene (5.5%), nonacosane (5.3%) and terpinen-4-ol (4.6%). Copyright # 2000 John
Wiley & Sons, Ltd.

KEY WORDS: Chaerophyllum aksekiense; Umbelliferae; essential oil; heptacosane; humulene epoxide II

Introduction Table 1. Composition of the oil of Chaerophyllum

aksekiense A. Duran et Duman
Chaerophyllum L (Umbelliferae) is represented in the Compound RIa (%)
Flora of Turkey by 15 species, three of them being
Sabinene 1132 2.2
endemic to Turkey.1±3 C. aksekiense A. Duran et Myrcene 1174 0.1
Duman has recently been described from Turkey as a a-Terpinene 1188 tr
new species.3 This is the ®rst report on the chemical Limonene 1203 0.3
(Z)-b-Ocimene 1246 0.7
composition of this species. g-Terpinene 1255 0.6
(E)-b-Ocimene 1266 0.2
p-Cymene 1280 1.1
Terpinolene 1290 5.5
Experimental Octanal 1296 tr
Nonanal 1400 tr
Chaerophyllum aksekiense was collected in Antalya; 1,3,8-p-Menthatriene 1409 tr
a,p-Dimethylstyrene 1444 tr
Akseki, PõnarbasË õ village, CËataloluk at an altitude of trans-Sabinene hydrate 1474 1.0
1450 m on 24 July 1997. The voucher specimens are 4,8-Epoxyterpinolene 1479 1.4
kept at the Herbarium of the Faculty of Pharmacy, (Z)-Epoxyocimene 1497 tr
Decanal 1506 tr
Anadolu University, EskisË ehir, Turkey (ESSE 12420). b-Bourbonene 1535 tr
Crushed fruits were water-distilled for 3 h using a (E)-2-Nonenal 1547 0.1
Clevenger-type apparatus to produce oil in a yield of cis-Sabinene hydrate 1556 0.7
p-Menth-3-en-7-al 1568 0.3
1.1%. trans-p-Menth-2-en-1-ol 1574 0.3
Pinocarvone 1586 0.1
Bornyl acetate 1597 tr
b-Elemen 1600 0.3
GC±MS Analysis Hexadecane 1603 tr
Terpinen-4-ol 1611 4.6
The essential oil was analysed using a Hewlett-Packard b-Caryophyllene 1612 2.5
cis-p-Mentha-2-en-1-ol 1638 0.1
GCD system. Innowax (a polyethylene glycol phase) Thuj-3-en-10-al 1641 0.1
fused silica capillary column (60 m  0.25 mm i.d. with Sabinaketone 1651 0.1
0.25 mm ®lm thickness) was used, with helium as carrier (E)-2-Decanal 1658 0.1
cis-Sabinyl acetate 1660 1.0
* Correspondence to: K. H. C. BasË er, Anadolu University, Medicinal and
Aromatic Plant and Drug Research Centre (TBAM), 26470 EskisË ehir, Turkey. Table continued over page

Copyright # 2000 John Wiley & Sons, Ltd. Flavour Fragr. J. 2000; 15: 43±44
44 K. H. C. BASËER ET AL.

Table 1. Continued gas. GC oven temperature was kept at 608C for 10 min
Compound RIa (%)
and programmed to 2208C at a rate of 48C/min, and
then kept constant at 2208C for 10 min, and
Citronellyl acetate 1671 0.2 programmed to 2408C at a rate of 18C/min. Split ratio
(E)-b-Faresene 1672 6.2
a-Humulene 1684 5.5 was adjusted at 50 : 1. The injector temperature was at
Myrtenyl acetate 1698 0.1 2508C. MS were taken at 70 eV. Mass range was m/z
a-Terpineol 1707 0.3 35±425. A library search was carried out using the
trans-Sabinol 1719 0.2
Germacrene D 1726 1.4 Wiley GC±MS Library and the in-house TBAM
Phellandral 1744 0.2 Library of Essential Oil Constituents. The MS were
cis-Piperitol 1758 0.2 also compared with those of reference compounds and
(E,E)-a-Farnesene 1760 0.1
Geranyl acetate 1765 tr con®rmed with the aid of retention indices from
p-Methyl acetophenone 1797 0.8 published sources. Relative percentage amounts of the
Cuminaldehyde 1802 0.2 separated compounds were calculated from total ion
p-Mentha-1,5-dien-7-ol 1815 0.3
2,6-dimethyl-3(E),5(E),7-octatrien-2-ol 1830 0.2 chromatograms using a computerized integrator.
p-Cymen-8-ol 1864 2.9
(E)-Geranyl acetone 1868 tr
Nonadecane 1900 tr
Tetradecanal 1933 0.1 Results and discussion
Isocaryophyllene oxide 2000 1.5
Caryophyllene oxide 2008 6.0 As shown in Table 1, 69 components were identi®ed,
Humulene epoxide I 2045 0.8
(E)-Nerolidol 2049 0.3 constituting 82.0% of the Chaerophyllum aksekiense
Humulene epoxide II 2071 7.8 oil. Sesquiterpenes (33.8%) predominated over the
Humulene epoxide III 2081 0.4 monoterpenes (26.1%) and paran hydrocarbons
Carvacrol 2240 0.9
Tricosane 2300 0.8 (21.5%) constituted the third important group of
Caryophylladienol II 2324 0.3 compounds, with heptacosane (10.1%) being the main
Caryophyllenol II 2392 0.5 component in the oil.
Pentacosane 2500 2.2
Hexacosane 2600 0.6
Heptacosane 2700 10.1
Octacosane 2800 2.0
Nonacosane 2900 5.3 References
Monoterpene hydrocarbons 10.7 1. P. H. Davis, Flora of Turkey and the East Aegean Islands, Vol. 4,
Oxygenated monoterpenes 15.5 pp. 312±318, University Press, Edinburgh (1972).
Sesquiterpene hydrocarbons 16.1 2. P. H. Davis, R. R. Mill and R. R. Kit Tan (Eds), Flora of
Oxygenated sesquiterpenes 17.7 Turkey and the East Aegean Islands, Vol. 10, p. 146, (Supplement),
Alkanals 0.5 University Press, Edinburgh (1988).
Paran hydrocarbons 21.0 3. A. Duran and H. Duman, Edinb. J. Bot., 56, 47±53 (1999).
Others 0.5
Total 82.0

tr ˆ trace 5 0.1%.
a Retention index on polar column.

Copyright # 2000 John Wiley & Sons, Ltd. Flavour Fragr. J. 2000; 15: 43±44