The essential oil composition of Bubonium graveolens (Forssk.) Maire from the Algerian Sahara

Abstract

The chemical compositions of the essential oils from the leaves and flowers of the endemic medicinal plant
Bubonium graveolens, collected from south-western Algeria, were established by GC–MS analysis. A total of 43 compounds were identified, representing, for leaves and flowers respectively, 97% and 97.6% of the total oil composition. 1,8-Cineole (21.5% in leaves, 16.5% in flowers), δ -cadinol (19.1% in leaves, 13.9% in flowers) were the major compounds identified.
The flower oil was characterized by a high percentage of 2,6-dimethyl-1,6-heptadien-4-yl acetate (19.4%) and transchrysanthenyl acetate (18.7%). δ -Cadinene (12.4%) was detected exclusively in the leaf oil. This is the first report on the chemical compounds of the oil of the B. graveolens. Copyright © 2007 John Wiley & Sons, Ltd.

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286 A. CHERITI ET AL.
Copyright © 2007 John Wiley & Sons, Ltd. Flavour Fragr. J. 2007; 22: 286– 288
DOI: 10.1002/ffj
FLAVOUR AND FRAGRANCE JOURNAL
Flavour Fragr. J. 2007; 22: 286–288
Published online 3 April 2007 in Wiley InterScience
(www.interscience.wiley.com) DOI: 10.1002/ffj.1794
The essential oil composition of Bubonium graveolens
(Forssk.) Maire from the Algerian Sahara
Abdelkrim Cheriti,1* Amel Saad,1 Nasser Belboukhari1 and Said Ghezali2
1Phytochemistry and Organic Synthesis Laboratory, University of Bechar, BP 114, 08000 Bechar, Algeria
2Department of Industrial Chemistry, IAP, 35 000 Boumerdes, Algeria
Received 21 July 2005; Revised 16 January 2007; Accepted 22 January 2007
ABSTRACT: The chemical compositions of the essential oils from the leaves and flowers of the endemic medicinal plant
Bubonium graveolens, collected from south-western Algeria, were established by GC–MS analysis. A total of 43 compounds
were identified, representing, for leaves and flowers respectively, 97% and 97.6% of the total oil composition. 1,8-Cineole
(21.5% in leaves, 16.5% in flowers),
δδ
δδ
δ
-cadinol (19.1% in leaves, 13.9% in flowers) were the major compounds identified.
The flower oil was characterized by a high percentage of 2,6-dimethyl-1,6-heptadien-4-yl acetate (19.4%) and trans-
chrysanthenyl acetate (18.7%).
δδ
δδ
δ
-Cadinene (12.4%) was detected exclusively in the leaf oil. This is the first report on the
chemical compounds of the oil of the B. graveolens. Copyright © 2007 John Wiley & Sons, Ltd.
KEY WORDS: Bubonium graveolens; Asteraceae;
δ
-cadinol; 1,8-cineole; trans-chrysanthenyl acetate; 2,6-dimethyl-1,6-
heptadien-4-yl acetate; essential oil composition
* Correspondence to: A. Cheriti, Phytochemistry and Organic Synthesis
Laboratory, University of Bechar, 08000 Bechar, Algeria.
E-mail: karimcheriti@yahoo.com
Introduction
Bubonium graveolens (Forssk.) Maire [syn. Asteriscus
graveolens subsp. stenophyllus, Buphthalmum steno-
phyllum (Link), Nauplius graveolens subsp. stenophyllus
(Link), and Bubonium odorum (Schoub.)],1 belonging to
the family Asteraceae, is an endemic herbaceous medici-
nal aromatic plant mainly distributed in south-western
Algeria and south-eastern Morocco.2,3 It is locally known
as ‘tafss’ and has been used in Sahara folk medicine as
a stomachic, for treating fever, gastrointestinal tract
complaints, cephalic pains, bronchitis and as an anti-
inflammatory.4–6 The WHO estimated that 80% of people
living in developing countries are almost completely
dependent on traditional medical practices for their
primary health care needs, and plants are known to be the
main source of drug therapy in traditional medicine.7,8
Southern Algeria, with its rich floral resources and
ethnobotanical history, is an ideal place to screen plants
for biological activity.9
To the best of our knowledge, there are no previous
reports on the oil content and chemical composition of B.
graveolens. Thus, in the continuation of our ethnophar-
macological, phytochemical and antimicrobial studies
of the Algerian Sahara medicinal plants,10–14 we report
here the results of our studies on the composition of B.
graveolens oil from the Algerian Sahara.
Materials and Methods
Plant Material
Aerial parts of B. graveolens were collected during
flowering in south-western Algeria (March–May 2003),
and identified by the National Agency of Nature Protec-
tion (ANN), Bechar, Algeria.2,3 A voucher specimen was
deposited at the Herbarium of POSL Laboratory, Faculty
of Sciences (University of Bechar, Algeria) under Acces-
sion No. CA 00/14.
Isolation of the Essential Oils
Samples of flowers and leaves were air-dried and care-
fully crumbled. Both flowers and leaves were hydro-
distilled separately for 6 h in an all-glass Clevenger
apparatus, in accordance with the 3rd Edition of the
European Pharmacopoeia, cited by Bruneton.15 The oil
was dried over anhydrous sodium sulphate and stored at
4°C until analysis.
GC and GC–MS Analyses
Analytical gas chromatography was carried out using a
Shimadzu GC-17A gas chromatograph equipped with a
flame ionization detector and a Supelco CBP-5 capillary
column (30 m × 0.25 mm, film thickness 0.25 µm). The
oven temperature was programmed as follows: 60 °C for

ESSENTIAL OIL OF BUBONIUM GRAVEOLENS 287
Copyright © 2007 John Wiley & Sons, Ltd. Flavour Fragr. J. 2007; 22: 286– 288
DOI: 10.1002/ffj
2min, then rising to 240 °C at 3 °C/min, then to 300 °C
for 10 °C/min, ending with 10 min at 300 °C; carrier gas,
He at a flow rate of 1.0 ml/min); injector and detector
temperature, 240 °C; samples were injected by splitting,
split ratio 1:5.
GC–MS analysis was performed on a Shimadzu
GC-17A gas chromatograph interfaced with Shimadzu
QP5000 mass spectrometer, operating in electron impact
mode at 70 eV with an ion source temperature of 250 °C,
scan mass range m/z 40–400, at a sampling rate of 0.5
scans/s. The operating conditions were analogous to those
reported in the GC analysis.
The oil components were identified by computer using
NIST21 and NIST107 libraries of mass spectral data, by
comparison of their retention indices (Determined relative
to the retention times of a n-alkanes homologous series)
and visual inspection of the mass spectra from literature
for confirmation.16– 21 The relative amounts of the indi-
vidual components found in the oil are based on the peak
areas obtained, without FID response factor corrections.
Table 1. Chemical composition of the essential oils from B. graveolens
Compounds RI* Percentage
Leaves Flowers
Heptanal 882 0.1 0.2
(E)-2,5-Dimethyl-1,6-octadiene 911 1.0 0.1
α
-Pinene 936 0.2 4.6
Camphene 950 tr 0.2
β
-Pinene 978 0.9 0.8
6-Methyl-5-hepten-2-one 985 1.2 0.5
β
-Myrcene 987 1.9 4.8
α
-Phellandrene 1002 tr 0.4
(1S,3R,6R)-3-Carene 1010 tr 0.1
β
-Phellandrene 1020 0.3 0.1
1,8-Cineole 1024 21.5 16.5
Limonene 1025 0.5 0.6
Ocimene 1029 tr 0.1
Terpinolene 1082 0.2 0.1
4-Methyl-4-vinyl-1,4-butanolide 1090 0.9 tr
Bicyclo-5.1.0-octane,8-(1-methylethylidene) 1099 0.9 tr
(E)-Dodecene-6-ene 1106 0.2 tr
Terpinen-4-ol 1141 0.2 0.1
exo-2-Hydroxycineole 1196 4.7 4.2
α
-Limonene diepoxide 1232 2.4 0.2
trans-Chrysanthenyl acetate 1236 2.8 18.7
Linalyl formate 1239 0.4 0.6
2,6-Dimethyl-1,6-heptadien-4-yl acetate 1264 2.4 19.4
Bornyl acetate 1270 tr 0.1
Copaene 1379 0.4 1.8
cis-Geranyl acetate 1380 3.0 0.4
trans-Geranyl acetate 1384 0.2 0.1
(E)-2,7-Octadien-1-yl acetate 1388 3.5 0.3
α
-Bergamotene 1411 0.5 0.2
α
-Caryophyllene 1414 2.1 1.9
β
-Caryophyllene 1421 0.8 0.7
α
-Farnesene 1491 tr 0.1
α
-Amorphene 1492 0.1 tr
δ
-Cadinene 1520 12.4 1.0
(E)-Nerolidol 1522 0.9 0.7
Germacrene B 1552 0.2 0.3
(Z)-Nerolidol 1553 1.4 0.4
Humulene epoxide II 1603 6.2 0.2
δ
-Cadinol 1633 19.1 13.9
Bicyclo-2.2.1-heptane-2,3-dione,6- (acetyloxy) 1684 2.6 0.2
trans, trans-Dibenzylienacetone 1960 0.6 0.4
Decanoic acid decyl ester 2084 0.3 2.6
Di-n-octyl phthalate 2431 tr tr
Total 97.0 97.6
Monoterpene hydrocarbons 7.1 12.4
Oxygenated monoterpenes 37.6 60.3
Sesquiterpenes hydrocarbons 16.5 6.0
Oxygenated sesquiterpenes 27.6 15.2
Others 8.2 3.7
tr, trace, <0.01.
* Retention indices on CBP-5 column.

288 A. CHERITI ET AL.
Copyright © 2007 John Wiley & Sons, Ltd. Flavour Fragr. J. 2007; 22: 286– 288
DOI: 10.1002/ffj
Results and Discussion
Greenish-yellow oils with yields of 0.25% and 0.35%
were obtained from the leaves and flowers, respectively,
of B. graveolens, with a characteristic pleasant-smelling,
strong odour. The chemical composition of the oil is
presented in Table 1; 43 compounds were identified in
both leaves and flowers, representing 97% and 97.6%,
respectively, of the total oil.
The essential oil of B. graveolens contained mainly
oxygenated monoterpenes (37.6%, 60.3%) in leaves
and flowers, respectively, with 1,8-cineole (21.5%) as
the main constituent in the leaves and 2,6-dimethyl-
1,6-heptadien-4-yl acetate (19.4%), trans-chrysanthenyl
acetate (18.7%) and 1,8-cineole (16.5%) as the main
constituents in the flowers.
Oxygenated sesquiterpenes were also the dominant
class of compounds in both leaves and flowers (27.6%
and 15.2%, respectively), with
δ
-cadinol (19.1%, 13.9%)
as the main constituent. The qualitative composition of
the two essential oils was similar, but marked quantitative
differences were observed in the following compounds:
1,8-cineole (21.5% in leaves, 16.5% in flowers),
δ
-
cadinol (19.1% in leaves, 13.9% in flowers),
β
-myrcene
(1.9% in leaves, 4.8% in flowers). trans-Chrysanthenyl
acetate (18.7%) and 2,6-dimethyl-1,6-heptadien-4-yl
acetate (19.4%) were found in higher concentrations in
the flowers.
δ
-Cadinene (12.4%) and humulene epoxide II
(6.2%) dominated in the leaves.
A significant amount of 1,8-cineole (up to 15.0%)
has also been found in the oils of some species of
Asteraceae: Osmitopsis asteriscoides (59.9%),22 Artemisia
asiatica nakai (39.7%),23 Achillea taygetea (26.6%)24 and
Matricaria decipiens (10.5%).25
Many studies have shown the influence of plant parts
on the chemical composition of essential oils. In fact, in
the oil obtained from Inula graveolens, the flowers were
richer in monoterpene hydrocarbons (7.2% vs. 2.3% for
leaves and stems, respectively), in contrast to oxygenated
sesquiterpenes, which account for 20.6% for leaves and
stems and 15.9% for flowers.26 Another study showed
the high concentration of trans-chrysanthenyl acetate in
flowers (3.2%) compared with the leaves (1.2%) in the
oil of Conyza bonariensis.27
The quantitative variability of oil components in the
leaves and flowers of B. graveolens may be attributed to
the growth phase of the plant, and a study of this might
be interesting from a biochemical point of view.28 Further
experiments are planned to establish the influence of the
components of these oils on antimicrobial activity.
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