FLAVOUR AND FRAGRANCE JOURNAL SEED ESSENTIAL OIL OF PETROSELINUM CRISPUM 143

Flavour Fragr. J. 2006; 21: 143147

Published online 15 June 2005 in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1548

Essential oil composition of the parsley seed of cultivars

marketed in Poland
Anna Kurowska* and Ilona Ga8zka
Institute of General Food Chemistry, Technical University, 90924 7d9, Stefanowskiego 4/10, Poland
Received 4 February 2004; Revised 29 July 2004; Accepted 9 August 2004

ABSTRACT: The chemical compositions of parsley seeds essential oils from 11 cultivars (three of leaf parsley and eight
of root parsley) obtained from different commercial sources, marketed in Poland, were compared. The constituents of
essential oils were investigated by GC, GCMS and 1H-NMR spectroscopy. Eighteen components (representing approxi-
mately 99.9% of the total oil composition) were identied in the cultivar festival. There were signicant differences
between quantities of the oil components. The content of phenylpropene derivatives in the seed essential oils permits
convar. crispum (leaf parsley), main constituent myristicin, and convar. radicosum (root parsley), main constituent apiole,
to be distinguished. Copyright 2005 John Wiley & Sons, Ltd.

KEY WORDS: Petroselinum crispum (Mill.) Nym.; Apiaceae; parsley seed; cultivar; essential oil

Introduction Jork recognized four races of parsley, depending on

Parsley Petroselinum crispum (Mill.) Nym. syn. P.
sativum Hoffm., family Apiaceae, a medicinal and food
plant, is known for its aromatic leaves and roots. The
essential oil is present in all parts of the plant. Leaf oil of
the nest quality has a avour that resembles the fresh
herb and can only be obtained in low yield. Usually com-
mercial essential oil is derived from mature seeds (fruits)
and has a distinctly different avour. It is used as a
avouring agent in food products or fragrance in per-
fumery and cosmetics, as stated in many patents. Anti-
microbial, diuretic and weak antioxidant activities of
parsley essential oil have been reported.1 4 Myristicin
from parsley oil is a potential cancer chemoprotective
agent.512
Volatiles have been also obtained by different methods
(solvent extraction,13 extraction distillation,14 SFE21).
The yield and characterization of volatiles of parsley
seeds have previously been reported.4,5,1320 Many parsley
cultivars from different countries (Mongolia,20 France,13,19
Korea,14 Italy, Pakistan, Tashkent13) have been analysed.
Obvious and signicant differences between essential oil
components were observed, but generally parsley seeds
are rich in monoterpenes (in particular - and -pinene)
and oxygenated phenylpropenes, which constitute the
greater part of the oil. It was found that the leaf parsley
seed essential oil was rich in myristicin, while in root
parsley seed oil apiol was a predominant compound.13
The composition of the oil is inuenced by genotype,
environmental conditions and cultural systems. Stahl and
* Correspondence to: A. Kurowska, Institute of General Food Chemistry,
Technical University, 90924 Ldz, Stefanowskiego 4/10, Poland.
E-mail: ankur@snack.p.lodz.pl
which compounds predominated in the seed essential oil
(apiole, myristicin, 1-allyl-2,3,4,5-tetrametoxybenzene and
a middle chemotype).17
The cultivars cultivated and/or marketed in Poland
have not been previously investigated. The aim of this
study was to compare the chemical composition of 21
parsley seed essential oils of 11 cultivars marketed in
Poland.
Experimental
Plant Material and Oil Isolation
Eleven parsley seed cultivars (three of leaf parsley
and eight of root parsley) were investigated. The plant
material was derived from six different commercial
sources. The seeds were pulverized and hydrodistilled in
a glass apparatus for 5 h, with the yield of essential oil
amounting to 0.62.3% (Table 1).
Separation and Identification of the Oil
Components
The essential oil of leaf cultivar festival (16.2 g) was
distilled in a 20 cm Vigreux column under reduced pres-
sure to give the following fractions, containing the main
constituents:
1. 35 49 C/15 Torr (5.6 g); -pinene (56.9%), -pinene
(35.6%).
2. 4654 C/15 Torr (0.8 g); -pinene (45.9%), -
phellandrene (39.2%).

Copyright 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 143147
144 A. KUROWSKA AND I. GALZKA

Table 1. Yield of parsley seed essential oils GCMS

Cultivar Yield (cm3/100 g)
Fisons MD 800 coupled with GC 8000, 70 eV; carrier
Root parsley ka^ka 0.7 gas, He at 0.8 cm3/min. Temperature and other para-
alba 0.8 meters as in GC1 and GC2.
omega 0.8
goplana 0.9 1
lenka 0.81.0 H-NMR
berliska 0.6 0.9
vistula 0.6 0.7
cukrowa 0.8 0.9
Bruker AM
250, 250 MHz, in CDCl3.
Leaf parsley karnaval 1.5
paramount 1.6 1.7
festival 1.8 2.2
Results and Discussion

3. 109119 C/18 Torr (6.3 g) myristicin (59.8%), apiole
(7.7%).
4. Residue (3.4 g); apiole (51.6%), 1-allyl-2,3,4,5-
tetrametoxybenzene (31.3%), myristicin (15.8%),
elemicin (1.3%).
The residue was separated by repeated ash chromatog-
raphy (FC) on Silica gel 60, 230400 mesh ASTM
(Merck) with pentane (monoterpenes) or hexane and in-
creasing amounts of diethyl ether, with monitoring by
TLC and GC, and oxygenated phenylpropenes of 77
100% purity were isolated.
Identication of the components of the obtained frac-
tions and of other essential oils (without separation) was
done by GC and GCMS on two columns of different
polarity by comparison of retention indices (RI) and MS
spectra with our in-house library of reference substances,
computer database (NIST) and/or literature data.22 Reten-
tion indices (RI) were calculated by comparing the reten-
tion times of the eluting peaks with those of C7 C26
alkanes. Additionally, phenylpropanoids were identied
by comparing of 1H-NMR spectra with literature
data.12,23,24
Apparatus
GC 1
Carlo Erba VEGA GC 6000, equipped with a capillary
column, 30 m 0.25 mm i.d., lm thickness 0.25 m,
coated with CP Sil 5CB, FID, injector SSL. Temperature
programme: 60 C (4 min) rising to 300 C at 5 C/min;
carrier gas, N2 at 1 cm3/min.
GC 2
Carlo Erba Instruments type HRGC-5300, equipped with
a capillary column, 30 m 0.32 mm i.d., lm thickness
0.50 m, coated with CP-Wax 52CB. Other parameters
as in GC 1.
The yield of the essential oil from root parsley seeds was
generally lower (0.61.0%) than that obtained from leaf
parsley seeds (1.52.2%) (Table 1). This nding is con-
rmed by other studies.13,17
Parsley seed volatiles can be also obtained with greater
yield (up to 7%) by solvent extraction, likewise at earlier
investigations.13,19,20
The leaf cultivar festival was found to be the
richest in essential oil (up to 2.2%); 18 compounds
(constituting 99.9% of the oil) were identied (Table 2).
In this cultivar monoterpene hydrocarbons (57%),
mainly -pinene (32%) and -pinene (19%) were found
as the predominant compounds, accompanied by the
phenylpropene derivatives myristicin (18%), apiole
(10%) and 1-allyl-2,3,4,5,-tetramethoxybenzene (13%)
(Table 2). Monoterpenes hydrocarbons and oxygenated
phenylpropenes were the main groups of compounds in
all parsley specimens which were investigated.
The chemical composition of all the essential oils ana-
lysed was similar but there were differences in the quanti-
tative proportions of compounds. The content of - and
-pinene was 45.967.8% in the leaf parsley cultivars and
16.062.5% in the root parsley cultivars (Tables 3, 4).
Among phenylpropene derivatives, apiole (16.674.9%)
was the main constituent in the root parsley cultivars and
myristicin (12.442.2%) in the leaf parsley cultivars.
The commercial essential oil of parsley seeds (with
predominant compound apiole or myristicin) can be de-
termined quite easily, because its chemical composition
depends entirely on the convar (either root or leaf) of
cultivar from which it is obtained. This observation con-
rms those made in earlier studies.13 Additionally, it has
been noticed that the quantities of 1-allyl-2,3,4,5,-
tetramethoxybenzene is the characteristic difference be-
tween the leaf and the root parsley seed essential oils.
The content of this compound was higher in leaf parsley
seed oils (up to 13%) than in seeds of root parsley
cultivars (max. 0.4%).
In all investigated essential oils only few oxygenated
monoterpenes and sesquiterpenes were found. It was pre-
viously reported that limonene13 and terpinolene14 were
found in some of the essential oils investigated, but these
were not found in our samples. p-Cymene (RI 1016) was

Copyright 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 143147
 SEED ESSENTIAL OIL OF PETROSELINUM CRISPUM 145

Table 2. Chemical composition of seed essential oil of leaf parsley cultivar festival

No. RI* Compound Content in essential Identification

oil (%)

1 924 -Thujene 0.2 RI
MS

2 933 -Pinene 32.0 RI
MS
3 943 Camphene 0.2 RI
MS
4 966 Sabinene 0.7 RI
MS
5 971 -Pinene 19.0 RI
MS
6 982 Myrcene 0.1 RI
MS
7 997 -Phellandrene 0.2 RI
MS
8 1020 -Phellandrene 4.9 RI
MS
9 1049 -Terpinene 0.1 RI
MS
10 1171 Myrtenal 0.2 RI
MS
11 1415 -Caryophyllene 0.1 RI
MS
12 1446 trans--Bergamotene Tr RI
MS
13 1463 (Z )- -Farnesene 0.1 RI
MS
14 1494 Myristicin 18.3 RI
MS 1H-NMR
15 1520 Elemicin 0.6 RI
MS
16 1568 1-Allyl-2,3,4,5-tetramethoxybenzene 12.8 RI
MS 1H-NMR
17 1587 Carotol 0.3 RI
MS
18 1651 Apiole 10.1 RI
MS 1H-NMR
Total 99.9
Monoterpene hydrocarbons 57.4
Monoterpene oxygenate hydrocarbons 0.2
Sesquiterpene hydrocarbons 0.2
Sesquiterpene oxygenate hydrocarbons 0.3
Phenylpropene derivatives 41.8

*
Compounds are listed according to their elution on CP Sil 5CB capillary column. Tr, traces < 0.05%.

Table 4. Comparison of chemical composition of seed essential oils of leaf parsley cultivars

Compound Leaf parsley cultivars/no. of commercial sources of parsley seeds

festival/1 festival/5 festival/6 karnaval/3 paramount/6 paramount/3

(%)

-Thujene 0.3 0.2 0.2 0.2 0.2 0.2

-Pinene 40.6 32.0 31.0 26.7 26.0 30.8
Camphene 0.3 0.2 0.2 0.3 0.2 0.6
Sabinene nf 0.7 nf 0.9 nf 0.4
-Pinene 27.2 19.0 20.0 19.7 19.9 18.6
Myrcene Tr 0.1 0.2 0.2 0.5 nf
-Phellandrene 0.3 0.2 0.2 0.2 0.2 0.3
-Phellandrene 8.8 4.9 6.5 4.5 4.4 4.9
-Terpinene nf 0.1 0.1 nf 0.2 nf
Myrtenal 0.5 0.2 0.3 0.5 Tr nf
Myristicin 12.4 18.3 17.8 31.0 42.2 41.1
Elemicin Tr 0.6 0.2 0.9 2.7 nf
1-Allyl-2,3,4,5- 5.6 12.8 12.7 5.7 2.3 2.0
tetramethoxybenzene
Carotol 0.1 0.3 0.2 0.3 Tr 0.4
Apiole 3.7 10.1 10.2 8.8 Tr 0.5
Total 99.8 99.7 99.8 99.9 98.8 99.8

nf, not found; Tr, traces < 0.05%.

found only in some root parsley seed essential oils (up to
0.5%) (Table 4) and -phellandrene only in leaf cultivars
(0.20.3%) (Table 3). Carotol and myrtenal, previously
identied only in the leaves or whole plants of parsley,6,25
in our investigations were identied in some parsley seed
essential oils (up to 0.4% and 1.6%, respectively).
Two samples under investigation (berliska/3 and
berliska/6) can be classied among the apiol chem-
ical race, according to Stahl and Jork17 (apiol 5880%;
myristicin 928%; 1-allyl-2,3,4,5-tetrametoxybenzene
traces 6%). The other cultivars do not really comply with
the chemical race denitions proposed by these authors.
The same cultivars provided by different commercial
sources contain the same chemical constituents in the
essential oils, but not in the same quantities (Tables 3,
4). These differences in the quantitative chemical

Copyright 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 143147
 146

Table 3. Comparison of the chemical composition of seed essential oils of root parsley cultivars

Copyright 2005 John Wiley & Sons, Ltd.

A. KUROWSKA AND I. GALZKA

Compound Root parsley cultivars/no. of commercial sources of parsley seeds

kaska/ alba/ goplana/ omega/ cukrowa/ cukrowa/ vistula/ vistula/ berlinska/ berlinska/ berlinska/ berlinska/ lenka/ lenka/ lenka/
5 3 5 4 5 2 3 2 3 1 6 5 6 1 5
(%)

-Thujene 0.1 0.1 0.1 0.2 0.1 Tr 0.1 0.3 Tr 0.2 nf 0.3 0.2 0.1 0.3
-Pinene 10.7 10.0 20.1 19.3 17.9 34.1 17.0 38.1 8.8 34.1 10.8 29.8 26.5 35.3 36.3
Camphene 0.1 0.1 0.1 0.2 0.1 0.2 0.3 0.3 0.1 0.2 0.1 0.2 0.2 0.2 0.2
Sabinene 0.5 0.4 0.7 0.8 0.7 nf 0.5 nf 0.2 nf nf nf 0.7 0.4 1.2
-Pinene 9.1 10.4 14.9 16.2 13.8 24.8 14.6 28.7 7.2 26.1 9.4 21.6 19.0 25.8 26.5
Myrcene 0.1 nf 0.1 Tr 0.1 nf nf nf nf 0.1 nf 0.2 0.1 nf nf
p-Cymene 0.3 nf 0.1 0.2 0.4 nf 0.2 Tr 0.5 0.3 nf 0.5 0.5 nf 0.2
-Phellandrene 0.7 0.6 0.9 1.2 1.2 nf 1.5 1.7 nf 1.5 nf 1.3 1.4 nf 1.4
-Terpinene 1.5 0.3 0.9 0.7 1.9 nf 1.0 0.9 0.7 2.2 nf 2.1 1.7 nf 1.6
Myrtenal 0.9 1.0 0.7 1.7 0.6 0.1 nf 1.1 0.2 1.3 nf 1.6 1.1 nf 1.3
Myristicin 23.1 1.9 16.8 4.8 26.4 23.7 12.1 6.9 22.0 11.1 13.0 13.8 11.2 5.7 14.1
Elemicin 0.3 Tr 0.1 0.2 0.2 nf 0.2 Tr 0.3 0.1 1.4 0.3 Tr Tr 0.1
1-Allyl-2,3,4,5- 0.1 Tr 0.1 0.3 Tr 0.1 0.4 0.2 nf 0.1 nf 0.3 0.2 nf nf
tetramethoxybenzene
Carotol 0.2 0.1 0.1 0.1 0.1 nf nf 0.1 Tr 0.1 nf 0.1 0.2 nf 0.1
Apiole 34.3 74.9 44.1 53.4 33.6 16.9 51.8 21.2 59.4 22.4 65.1 27.5 36.4 32.4 16.6
Total 82.0 99.8 99.8 99.3 97.1 99.9 99.7 99.5 99.4 99.9 99.8 99.6 99.4 99.9 99.9

nf, not found; Tr, traces < 0.05%.

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 SEED ESSENTIAL OIL OF PETROSELINUM CRISPUM 147

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Copyright 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 143147