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Essential Oil of Nigella Damascena L.

(Ranunculaceae) Seeds
ARTICLE in JOURNAL OF ESSENTIAL OIL RESEARCH JANUARY 2003
Impact Factor: 0.79 DOI: 10.1080/10412905.2003.9712267

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et al.
J. Essent. Oil Res., Flamini
15, 56-57 (January/February
2003)

Essential Oil of Nigella damascena L.

(Ranunculaceae) Seeds

Gelsomina Fico, Ammar Bader, Guido Flamini,* Pier Luigi Cioni and Ivano Morelli
Dipartimento di Chimica Bioorganica e Biofarmacia, Universit di Pisa, via Bonanno 33, 56126 Pisa, Italy

Abstract
The chemical composition of the essential oil of Nigella damascena L. seeds, collected from fruiting plants in their
natural habitat, was examined in comparison with commercial seeds. Twenty-eight compounds were identified in
wild seeds by GC/MS: 10 sesquiterpene hydrocarbons (93.8%), two alkaloids (0.3%) and three monoterpenes in trace
amounts.
Twenty-six compounds were identified in commercial seeds by GC/MS: 15 sesquiterpene hydrocarbons (90.4%),
two alkaloids (3.3%) and nine monoterpenes in trace amounts. The alkaloids were damascenine and methyl 2-amino3-methoxy benzoate, the latter being detected for the first time in this species.

Key Words Index

Nigella damascena, Ranunculaceae, essential oil composition, -elemene, germacrene A, alkaloids.

Introduction
Nigella damascena L. is an herbaceous annual plant growing in grasslands, in temperate zones in Europe (1). The seeds
of this plant, similar to those of N. sativa L., are black and
minute and, because of their characteristic strawberry flavor,
they are used in gastronomy in Asian cultures.
The literature reports the diuretic effect of N. damascena
seeds (2), and the popular medicine suggests the decoction to
regularize and give rise to menstruation (3). A previous paper
about the composition of seed oil described only the presence
of the alkaloid damascenine and suggested the presence of
sesquiterpenes (4). From the hexane extract of the grounded
seeds, Tillequin et al. (5) purified and identified the sesquiterpene hydrocarbons -elemene and -selinene. The characteristic odor and taste of N. damascena seeds stimulated our
interest in studying their oil, and here we report the oil
composition of natural and commercial seeds.

Experimental
Plant material: N. damascena seeds were collected in
the first week of August 1999, in Arnaccio (Pisa, Italy) at 20 m
above the sea level. A voucher specimen was deposited in the
Dipartimento di Chimica Bioorganica e Biofarmacia, University of Pisa. The commercial seeds were purchased from
Ingegnoli, Milano (Italy).

Oil isolation: The natural and commercial seeds (respectively 50 g and 100 g) were powdered and then submitted to
hydrodistillation in a Clevenger-type apparatus for 3 h.
GC/MS: GC/EIMS analyses were performed with a Varian
CP-3800 gas chromatograph equipped with a DB-5 capillary
column (30 m x 0.25 mm, coating thickness 0.25 m) and a
Varian Saturn 2000 ion trap mass detector. Analytical conditions: injector and transfer line temperatures 220C and
240C, respectively; oven temperature programmed from
60-240C at 3C/min; carrier gas helium at 1 L/min; injection of 0.2 l (10% hexane solution); split ratio 1:30. Identification of the constituents was based on comparison of the
retention times with those of authentic samples and on computer matching against commercial (Nist 98 and ADAMS)
and home-made library mass spectra built up from pure
substances and components of known oils and MS literature
data (6-9). Moreover, all the molecular weights of the identified substances were confirmed by GC/CIMS using MeOH as
CI reagent gas, operating in the same conditions described for
GC/EIMS analyses.

Results and Discussion

The results presented in Table I show that both the
samples contained mainly sesquiterpenes, while monoterpenes were scarcely represented, often in trace amounts. The
main constituents of wild plants were germacrene A and Received: November 2000

*Address for correspondence

Revised: January 2001

1041-2905/03/0056-0057$6.00/0 2003 Allured Publishing Corp.
56/Journal of Essential Oil Research

Accepted: February 2001

Vol. 15, January/February 2003

Nigella damascena

elemene (52.7% and 38.4%, respectively) followed by caryophyllene (1.4%). A further seven sesquiterpenes were
detected, but in very low amounts (less than 1%). The monoterpenes were -pinene and limonene.
The commercial seed oil also contained germacrene A and
-elemene as main constituents, but in this case the latter was
the main component (23.6% and 49.6%, respectively). Other
important compounds were viridiflorene (9.5%), 7-epi-selinene (3.5%), and (Z)-9-octadecen-1-ol (2.1%). Monoterpenes in trace amounts were -pinene, -pinene, myrcene,
p-cymene, limonene, 1,8-cineole, -terpinene, camphor and
pulegone. Both the oils contained the alkaloids damascenine
and methyl 2-amino-3-methoxy benzoate. Commercial seeds
contained a higher concentration of damascenine (3.2%) than
those from wild plants (0.1%). The compound methyl 2amino-3-methoxy benzoate has been never previously identified in this species. It is known (10) that methinionine methylate
mostly the nitrogen atom than the oxygen or the carboxylic
group of anthranilic acid. Consequently the latter alkaloid
should be a metabolic product of damascenine.

References
1.

T.G. Tutin, V.H. Heywood, N.A. Burges, D.H. Valentine, S.M. Walters
and D.A. Webb, Flora Europea, p 209, Cambridge University Press:
Cambridge, (1964).

2.

H. Bekemeier, G. Leuschner and W. Shmollack, Antipyretische,

antioedematose und analgetische wirkung von damascenin im vergleich
mit acetylsalicylsaure und phenylbutazon. Arch. Int. Pharmacodyn.,
168, 199-211 (1967).

3.

M. Ballero and I. Fresu, Le piante di uso officinale nella Barbagia di Seui

(Sardegna Centrale) Fitoterapia, 64, 141-150 (1993).

4.

M. Paris, G. Clair and J. Unger, Recherche de principes odorants des

graines de Nigelle de Damas. Rivista Italiana E.P.P.O.S., 61, 225-227
(1979).

5.

F. Tillequin, C. Lecompte and M. Paris, Carbures sesquiterpeniques des

graines de Nigella damascena. Planta Med., 30, 59-61 (1976).

6.

E. Stenhagen, S. Abrahamsson and F.W. McLafferty, Registry of Mass

spectral data. J. Wiley & Sons, New York (1974).

7.

Y. Massada, Analysis of Essential Oils by Gas Chromatography and

Mass Spectrometry. J. Wiley & Sons, New York (1976).

8.

W. Jennings and T. Shibamoto, Qualitative Analysis of Flavor and

Fragrance Volatiles by Glass Capillary Chromatography. Academic
Press, New York (1980).

Vol. 15, January/February 2003

Table I. Composition of the essential oils of Nigella

damascena seeds

Compound
-pinene
-pinene
myrcene
2-pentylfuran
p-cymene
limonene
1,8-cineole
-terpinene
camphor
pulegone
-copaene
-bourbonene
-elemene
-caryophyllene
-gurjunene
-cadinene
-gurjunene
germacrene D
-selinene
valencene
-selinene
viridiflorene
germacrene A
7-epi--selinene
methyl 2-amino-3methoxyl benzoate
damascenine
spathulenol
(Z)-9-octadecen-1-ol
yield%

Wild plants

Commercial
plants

941
984
992
993
1030
1035
1039
1064
1154
1243
1377
1384
1390
1420
1430
1462
1476
1481
1489
1493
1495
1496
1506
1520

ta
t
t
0.1
38.4
1.4
0.3
0.1
0.6
0.6
0.3
52.8
0.1

t
t
t
t
0.1
0.1
t
t
t
0.1
1.0
49.6
0.7
0.1
0.4
0.6
0.4
0.4
0.4
9.5
23.6
3.5

1549
1569
1578
1805

0.2
0.1
-

0.1
3.2
0.1
2.1

0.27

0.13

RI

at = trace (<0.1%)

9.

N.W. Davies, Gas Chromatographic retention indexes of monoterpenes

and sesquiterpenes on methyl silicone and Carbowax 20M phases. J.
Chromatogr., 503, 1-24 (1990).

10. D. Grger, Alkaloids derived from tryptophan and anthranilic acid. In:
Secondary Plant Products. Edits. E.A. Bell and B.V. Charlwood. p. 145146, Springer-Verlag, Berlin (1980).

Journal of Essential Oil Research/57