Journal of Essential Oil Bearing Plants

ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/teop20

Chemical Characterization of Essential Oils

of Senecio glaucus ssp. Coronopifolius (Maire)
Alexander and Ridolfia segetum (L.) Moris Growing
in Morocco

Khadija Basaid , Bouchra Chebli , Rachid Bouharroud , James Nicholas

Furze , Alessandra Lopes de Oliveira & El Hassan Mayad

To cite this article: Khadija Basaid , Bouchra Chebli , Rachid Bouharroud , James Nicholas
Furze , Alessandra Lopes de Oliveira & El Hassan Mayad (2020) Chemical Characterization of
Essential Oils of Senecio�glaucus ssp. Coronopifolius (Maire) Alexander and Ridolfia�segetum
(L.) Moris Growing in Morocco, Journal of Essential Oil Bearing Plants, 23:5, 918-930, DOI:
10.1080/0972060X.2020.1818634

To link to this article: https://doi.org/10.1080/0972060X.2020.1818634

Published online: 07 Dec 2020.

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 TEOP 23 (5) 2020 pp 918 - 930 918
ISSN Print: 0972-060X
ISSN Online: 0976-5026

Chemical Characterization of Essential Oils of Senecio glaucus ssp. coronopifolius

(Maire) Alexander and Ridolfia segetum (L.) Moris Growing in Morocco

Khadija Basaid 1, Bouchra Chebli 1*, Rachid Bouharroud 2, James Nicholas

Furze 3,5,6, Alessandra Lopes de Oliveira 4, El Hassan Mayad 1,3

1
Laboratory of Mechanic Process Energy and Environment, Biotechnology and environment
engineering team, National School of Applied Sciences, Ibn Zohr University, Agadir, Morocco
2
Research Unit of Integrated Crop Production, Centre Regional de la Recherche
Agronomique d’ Agadir (INRA), Morocco
3
Laboratory of Biotechnology and Valorization of Natural Resources, Faculty of
Sciences- Agadir, Ibn Zohr University, BP 8106, 80000 Agadir, Morocco
4
Laboratory of High-Pressure Technology and Natural Products, Department of
Food Engineering, University of São Paulo (USP), Av. Duque de Caxias
Norte, 225, Pirassununga, SP 13635-900, Brazil
5
Control and Systems Engineering Department, University of Technology, Baghdad,
Alsinaah Street, P.O. Box: 19006, Postal Code: 10066, Baghdad, Iraq
6
Royal Geographical Society (with the Institute of British Geographers),
1 Kensington Gore, SW7 2AR, London, UK
Received 02 April 2020; accepted in revised form 29 August 2020

Abstract: Chemical profiles of essential oils hydrodistilled from whole plants of Senecio glaucus ssp.
coronopifolius (Maire) Alexander and aerial parts of Ridolfia segetum (L.) Moris growing in Morocco were
determined using gas chromatography/mass spectrometry (GC/MS). The analysis identified 84 compounds in
the oil isolated from S. glaucus ssp. coronopifolius and 61 constituents in R. segetum oil. Both oils had a
predominance of monoterpene hydrocarbons. α-Pinene (26.2 %) was the main compound of S. glaucus ssp.
coronopifolius oil, followed by myrcene (11.4 %) and p-cymene (9.9 %). Novelly (Z)-β-ocimene (19.7 %) dominated
R. segetum oil, followed by β-phellandrene (9.6 %) and β-pinene (8.6 %). This is the first report of (Z)-β-
ocimene-rich essential oil from R. segetum and α-pinene-rich essential oil from S. glaucus ssp. coronopifolius,
revealing new chemical profiles for both species. The oils have potential in agroecological and pharmaceutical
formulations, serving both economic and medicinal applications.

Key words: essential oil, Senecio glaucus ssp. coronopifolius, Ridolfia segetum, Morocco,
agroecological.

Introduction glaucus L. is an annual herb that belongs to this

Senecio L. (Senecioneae Cass.) is the largest genus. It has two subspecies: Senecio glaucus
genus of the Asteraceae family. It includes over ssp. glaucus and Senecio glaucus ssp. corono-
1500 species distributed worldwide. Amongst pifolius (Maire) Alexander. The latter has a wide
these, 22 species are found in Morocco 1. Senecio distribution, ranging accross the Canary Islands,

*Corresponding author (Bouchra Chebli)

E-mail: < b.chebli@uiz.ac.ma > © 2020, Har Krishan Bhalla & Sons
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930
through North Africa in Southern Morocco, Tunisia
and Egypt to South-West Asia 2. Although there
are no formal reports on the traditional uses of
ssp. Coronopifolius, Senecio sp. have found use
in folk medicine as anti-inflammatory, antiemetic,
vasodilatator 3, hypoglycemic drug 4 and for treat-
ment of coughs, fever, colds and hepatic disorders
5
, eczema, wounds, bronchitis and asthma 6.
Biological functions of Senecio sp. include its
antioxidant 7, anti-inflammatory 7, antibacterial 8,
antifungal 9, insect-repellent 5, antitubercular,
molluscicidal 10 and cytotoxic 7 activities. Chemical
composition of S. glaucus ssp. coronopifolius
essential oil (EO) indigenous to Egypt, predomi-
nantly has myrcene (24.0 %) and dehydrofukinone
(21.0 %) compounds 11. However, chemical
studies have not been carried out on the species
collected from other geographic locations which
cover its wider distribution.
Ridolfia segetum (L.) Moris belongs to the
Apiaceae family, and is the only species of the
monotypic genus Ridolfia Moris 12. It is a steno-
Mediterranean species, distributed in Morocco 13,
Tunisia 14, Sardinia 15, Portugal 12, Spain 16 and the
Canaries 17. R. segetum is used in traditional medi-
cine to prevent coughing, constipation, respiratory
tract infections and for treatment of gastric acidity
12
. It has carminative, antispasmodic, antihaemo-
rrhoidal and emmenagogue properties. Additio-
nally, dried fruits of the plant are used as a eupep-
tic digestive in atony and digestive difficulty 18.
The frequent use of the species in traditional
medicine resulted in the identification of several
biological properties, such as antioxidant 12,14, anti-
bacterial 14,19,20, anti-inflammatory 12, anticancer
21
and HIV-1-inhibition 22. Previous studies have
reported the chemical profile of R. segetum EO
from different geographic locations, allowing the
distinction of two types of oils. The first type is
dominated by monoterpene hydrocarbons, usually
α-phellandrene, terpinolene, and p-cymene. EO
of R. segetum from Portugal was found to include
α-phellandrene (53-63.3 %) and terpinolene (8.6-
11.9 %) 12, and α-phellandrene (63.3 %) and
terpinolene (11.9 %) 21; whilst that of Italy con-
tained α-phellandrene (24.7 %) and terpinolene
(19.9 %) 15, and α-phellandrene (53.3 %) and
terpinolene (20.4 %) 22; whilst that of the EO of
the species in Spain was profiled and contained
919
α-phellandrene (39.4-69.5 %) and terpinolene (6-
27.6 %) 16, and p-cymene (8.8-83.6 %), α-phellan-
drene (32.0-33.8 %) and terpinolene (18.0-21.4
%) 23. Further, the Tunisian chemotype of the EO
contained α-phellandrene (34.7-47.8 %) and
terpinolene (9-23.7 %) 19. The second type of EO
of the species contains phenylpropanoids as major
compounds, usually myristicin and dillapiol. This
type was found to contain in Morocco α-
phellandrene (55 %) and myristicin (33 %) 13; in
Tunisia dillapiole (29.5-85.4 %) and myristicin
(13.1-31.5 %) 20; in Italy myristicin (70.8 %) 15, in
Spain dillapiol (0.1-45.7 %) and α-phellandrene
(5.2-56.9 %) 16 and dillapiole (5.1-39.6 %) and β-
pinene (10.3-20.9 %) 23.
Chemical composition of R. segetum EO varies
according to its origin in flowers, stems, leaves or
roots 15,16,23, extraction method 15,22, and geo-
graphical origin 16,19,20,23. The latter indicates the
presence of a chemical polymorphism within
different populations of the species. We
investigated the chemical composition of EOs
obtained from S. glaucus ssp. coronopifolius and
R. segetum (L.) Moris occurring in Morocco. This
study represents the first characterisation of R.
segetum aerial parts EO and reports EO
composition of S. glaucus ssp. coronopifolius
from a previously unstudied site.
Materials and methods
Plant materials
One kg of S. glaucus ssp. coronopifolius (stems,
leaves, flowers and roots) and one kg of aerial
parts of R. segetum (flowers, stems, fruits) were
collected during flowering and ripening stages,
from the Massa locality in the south-west of
Morocco (30° 0' 13.6" N 9° 38' 19.6" W), during
April, May and June of 2017. Identification of plant
material was verified by Dr. James N. Furze
(Royal Geographical Society, London, UK).
Voucher specimens of S. glaucus ssp. corono-
pifolius: no. SG-17 and R. segetum no. RS-17)
were deposited in the herbarium of the Laboratory
of Biotechnology, National School of Applied
Sciences, Ibn Zohr University, Agadir, Morocco.
Essential oil extraction
Plant matter was air dried in the shade. To obtain
the EOs, 250 g of each plants material was soaked
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930
in 1 L of distilled water in 2 L flasks. Each volume
was subjected to hydrodistillation using a
Clevenger-type apparatus, in a thermo regulated
heating mantle for 4 h at 50°C. Hydrodistillation
was repeated four times for each plant sample
and the average yield was calculated. The mixture
of distillated oils and water was collected, the upper
partition of EOs were separated from the lower
water phase, weighed and stored in tightly closed
dark vials at 4°C for further analysis.
Chemical composition of essential oils
The chemical composition of EOs was identified
and quantified by gas chromatography coupled
with mass spectrometry (GC/MS) 24. The GC was
carried out using a QP 2010 Plus gas chromato-
graphy apparatus (Shimadzu, Tokyo, JP) equipped
with an automatic injector (AOC-5000, Belle-
fonte, USA), and an RTX-5MS capillary column
(30 m × 0.25 mm ID × df 0.25 μm, 5 % diphenyl/
95 % dimethyl polysiloxane) (Restek, Belle-fonte,
USA). Helium was used as a carrier gas at a
pressure of 100, 2 KPa and a linear velocity of
46.3 cm/s. Fragmentation was effected by elec-
tronic impact. 1 μL of EO diluted in dichloro-
methane (Merck, Darm-stadt, GE) at a concen-
tration of 1 % (10 mg/ml) was injected using 1:10
split ratio. The injector temperature was 250°C
and the temperature at the interface between the
column and the ion source was set to 250°C. The
oven temperature was regulated to obtain a linear
ramp from 60 to 246°C (3°C/min). The acquisition
mass range was 50 to 470 m/z, at a speed of 909
u/s, using electron ionization (EI) with electron
energy of 70 eV.
The EOs components were identified by
matching their mass spectra value to NIST11 and
NIST11s database libraries, using the GC-MS
Solutions V2.5 software. The Van der Dool and
Kratz Index was calculated as an additional tool
for compounds identification 25. Quantification of
the oils components was performed by calculation
of their retention indices (RI exp) using a mixture
of hydrocarbons (C 10 H 22-C 40 H 82 ) (Fluka, St.
Louis, USA) as standard. Components were
further confirmed by comparison of their retention
indices with those reported in the literature (RI
lit) 26.
920
Results and discussion
The oil yield was expressed as a percentage
(g/100 g of dried plant material). The average
yields of EOs extracted from S. glaucus ssp.
coronopifolius and R. segetum were found to
be 0.2 g and 0.125 g from 250 g of each plant,
and the percentage of EO yields were 0.08 and
0.05 % respectively. De Pooter et al.11 reported
a slightly higher yield of 0.25 % for Egyptian S.
glaucus ssp. coronopifolius oil obtained by steam
distillation. Whereas, Ramadan et al.7 reported
yields of 0.5 and 0.25 % for capetula and shoots
oils of Egyptian S. glaucus L. For R. segetum,
Cabral et al.12 reported higher yields of 1.6 and
1.9 % in flowering and ripening stages respectively
of the species growing in Portugal, by hydro-
distillation. Conversely, yields of 0.4 and 0.94 %
were obtained using steam distillation and super-
critical CO2 respectively on R. segetum of Italy
15,22
. Variation in yield appears to be related to the
extraction method and parameters. The influence
of the duration of distillation on EO yield has been
reported 20, in addition to the vegetative stage of
plants 27, the season of harvest 28, geographic loca-
tion 29, and growth conditions of the plants 30.
GC/MS analysis of S. glaucus ssp. corono-
pifolius oil enabled the identification of eighty-
four compounds corresponding to 94.3 % of the
total constituents. 86.3 % of the total identified
compounds were terpenic, monoterpene hydro-
carbons were the most prominent (59.4 %),
followed by oxygenated sesquiterpenes (11.1 %),
sesquiterpene hydrocarbons (8.9 %), and oxy-
genated monoterpenes (6.9%) (Table 1). The
predominance of monoterpene hydrocarbons has
been reported for EOs of several species of the
genus Senecio 7. Alternatively, few species of this
genus were dominated by oxygenated compounds,
as was found in S. chrysanthemoides, S. verna-
lis and S. aegyptius var. discoideus 31, 32, 33.
α-Pinene was identified as the main compound
in ssp. coronopifolius EO at 26.2 %, followed
by myrcene (11.4 %) p-cymene (9.9 %), β-pinene
(7.7 %), γ-muurolene (4.0 %), deoxynivalenol (3.1
%) and α-phellandrene (2.7 %) (Table 1). Analysis
of oil extracted from aerial parts of S. glaucus
ssp. coronopifolius material collected in Egypt
11
showed myrcene (24.0 %), dehydrofukinone
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 921
Table 1. Chemical composition of the essential oil isolated
from Senecio glaucus ssp. coronopifolius

No. Compound RIexp RI lit Relative

content (%)

1 1-Isopropyl-4-methylenebicyclo [3.1.0]hex-2-ene 879 - 0.2

2 Cyclopropane, 1-methyl-2-pentyl- 880 - 1.0
3 α-Thujene 922 924 0.1
4 α-Pinene 930 932 26.2
5 Camphene 943 946 0.1
6 β-Pinene 973 974 7.7
7 Myrcene 985 988 11.4
8 Decane 1000 1000 0.1
9 α-Phellandrene 1001 1002 2.7
10 α-Terpinene 1011 1014 0.2
11 p-Cymene 1022 1020 9.9
12 γ-Terpinene 1050 1054 0.5
13 Ethanol, 1-(1-cyclohexenyl)- 1053 - 0.1
14 Terpinolene 1082 1086 0.3
15 Perillene 1101 1102 0.5
16 1-Octen-3-yl-acetate 1109 - 1.0
17 α-Campholenal 1120 1122 0.8
18 cis-Verbenol 1136 1137 0.4
19 2-Caren-10-al 1136 - 0.1
20 Pinocarvone 1157 1160 0.2
21 Naphthalene, 1,2,3,4,4a,5,8,8a-octahydro- 1157 - 0.6
4a-methyl-, trans-
22 Terpinen-4-ol 1173 1174 1.3
23 Phellandral 1175 - 0.3
24 Isopinocarveol 1180 - 0.4
25 α-Terpineol 1183 1186 0.4
26 p-Mentha-1(7),8-dien-2-ol 1188 1187 0.1
27 (1R)-(-)-Myrtenal 1194 1195 0.5
28 1-Methylverbenol 1209 - 0.1
29 4(10)-Thujen-3-ol, acetate 1224 - 0.1
30 p-Mentha-6,8-dien-2-ol, cis- 1226 1227 0.2
31 Cumaldehyde 1230 - 0.3
32 Isoaromadendrene epoxide 1281 - 0.5
33 p-Cymen-7-ol 1284 1289 0.1
34 2-Undecanone, 6,10-dimethyl- 1291 1293 0.1
35 Ledene oxide-(II) 1293 - 1.3
36 Carvacrol 1295 1298 0.4
37 2-(1,4,4-Trimethyl-cyclohex-2-enyl)-ethanol 1313 - 0.2
38 3a-Methyl-3a,4,5,6,7,8-hexahydro-2(3H)-azulenone 1357 - 0.1
39 (-)-β-Bourbonene 1386 1387 0.2
40 Alloaromadendrene 1386 - 0.2
41 (-)-cis-β-Elemene 1387 1389 0.4
42 (+)-Sativene 1390 1390 0.1
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 922
table 1. (continued).

No. Compound RIexp RI lit Relative

content (%)

43 Caryophyllene 1404 1408 0.6

44 α-Guaiene 1434 1437 0.4
45 Aromadendrene oxide-(2) 1435 1439 0.6
46 Di-epi-α-Cedrene 1438 1440 0.1
47 Seychellene 1441 1444 0.1
48 α-Humulene 1450 1452 0.1
49 Cycloisolongifolene, 8,9-dehydro-9-formyl- 1457 - 0.1
50 Aromadendrene oxide-(1) 1457 1458 0.1
51 Cadina-3,9-diene 1458 1461 0.5
52 Cyclohexene, 3-acetoxy-4-(1-hydroxy- 1471 - 0.8
1-methylethyl)-1-methyl-
53 Bicyclo[10.1.0]tridec-1- 1472 - 0.1
54 γ-Muurolene 1477 1478 4.0
55 4,5-di-epi-Aristolochene 1488 1487 0.3
56 β-Vatirenene 1489 - 0.3
57 2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a, 1502 - 0.5
5,6,7-octahydronaphthalene
58 Curcumene 1512 1514 0.9
59 Cubenol 1515 1514 0.2
60 Eremophila-1(10),11-diene 1557 1558 1.8
61 Spathulenol 1576 1577 1.0
62 Caryophyllene oxide 1580 1582 0.5
63 Tricyclo[5.2.2.0(1,6)]undecan-3-ol, 2- 1599 - 1.2
methylene-6,8,8-trimethyl-
64 Longipinocarveol, trans- 1599 - 0.1
65 Tau-muurolol 1641 1644 0.2
66 Guaia-1(10),11-diene 1674 1676 0.1
67 6-Isopropenyl-4,8a-dimethyl-1,2,3,5, 1690 - 0.1
6,7,8,8a-octahydronaphthalen-2-ol
68 2-(4a,8-Dimethyl-1,2,3,4,4a,5,6,7-octahydro 1745 - 0.2
-naphthalen-2-yl)-prop-2-en-1-ol
69 Hexahydrofarnesyl acetone 1754 - 0.7
70 Eudesma-5,11(13)-dien-8,12-olide 1801 - 0.2
71 6.β.Bicyclo[4.3.0]nonane, 5.β.-iodomethyl-
1.β.-isopropenyl-4α,5α-dimethyl- 1831 - 0.1
72 Podocarp-13-en-12-ol 1861 - 0.1
73 Anthracene, 1,2,3,4,5,6,7,8-octahydro-9,10-dimethyl- 1879 - 1.4
74 β-Springene 1922 - 0.1
75 Phytol 1940 1942 0.2
76 Phytol, acetate 1941 1942 0.1
77 Geranyl linalool 2026 2026 0.2
78 2-Butenoic acid, 2-methyl-, 1a,2,4,4a,5,9- 2109 - 0.9
hexahydro-4,4a,6-trimethyl-3H-oxireno[8,8a]
naphtho[2,3-b]furan-5-yl ester
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 923
table 1. (continued).

No. Compound RIexp RI lit Relative

content (%)

79 2-Butenoic acid, 2-methyl-, 4,4a,5,6,7,9- 2219 - 0.1

hexahydro-3,4a,5-trimethylnaphtho[2,3-b]
furan-4-yl ester, [4S-[4.α.(Z),4a.α.,5.α.]]-
80 Kauran-18-al, 17-(acetyloxy)-, (4.β.)- 2338 - 0.1
81 Deoxynivalenol 2385 - 3.1
82 Heneicosane 2395 2400 0.2
83 4-Piperidyl cyclopentylphenylglycolate 2498 - 0.2
84 β-d-Mannofuranoside, farnesyl 3014 - 0.3
Monoterpene hydrocarbons [No. 1, 3-12, 14] 59.4
Oxygenated monoterpenes [No. 15-20, 22-28, 31, 33, 36] 6.9
Sesquiterpene hydrocarbons [No. 39-44, 46-48, 51, 54-58, 66, 71] 8.9
Oxygenated sesquiterpenes [No. 32, 35, 45, 50, 59-65, 67, 68, 70, 81] 11.1
Others [No. 2, 13, 21, 29, 30, 34, 37, 38, 49, 52, 53, 69, 72-80, 82-84] 8.0
Total 94.3

RIexp = Retention indices determined on a 30 m Rtx-5 capillary column using a mixture of hydrocarbons
(C10H22-C40H82).; RIlit = Retention indices reported in the literature 26

(21.0 %) and p-cymene (9.9 %) to be the major
compounds of the oil. Myrcene and p-cymene
were found as major compounds of S. glaucus
ssp. coronopifolius oil in the current study at 11.4
and 9.9 % respectively, whereas dehydrofukinone
wasn’t detected. Comparatively, α-pinene, the
main compound detected in oil of the current study,
though was found in Egyptian oil in lower
proportions (2.6 % vs 26.2 %). Moreover, the
current study enabled the identification of a higher
number of compounds in the oil (84 compounds),
whereas, in Egyptian oil, De Pooter et al. 11
identified 31 compounds. Thus, a new chemical
profile of S. glaucus ssp. coronopifolius EO is
reported herein. Variability in chemical composition
of the species EO may be related to the difference
in plant parts used for extraction of the oil. In
experimentation of De Pooter et al.11, the EO was
extracted from aerial parts, whereas in the current
case, oil was extracted from whole plants, including
aerial parts and roots. A more recent study by
Ramadan et al.7 supported that variation in oil
composition is in accordance with the plant organ.
It reported the composition of capetula and shoots
EOs of S. glaucus L. from Egypt, and indicated
qualitative and quantitative variations between the
oils of different origin. The major compounds of
capetula oil were m-mentha-1(7),8-diene (31.4
%), cis-m-mentha-2,8-diene (22.9 %), dehydro-
fukinone (17.2 %) and α-terpinolene (3.9 %).
Whereas, the shoots oil contained m-mentha-
1(7),8-diene (25.6 %), cis-m-mentha-2,8-diene
(8.2 %), dehydrofukinone (19.9 %), α-fenchene
(5.6 %), 1,3,8-p-menthatriene (5.3 %) and β-
ocimene (3.4 %) as the main constituents. Plant
part plays a crucial role in the accumulation pattern
and chemical composition of EOs 34. Production
of plant terpenes is mainly controlled by trans-
criptional regulation of terpene synthase genes,
which have organ-specific expression patterns.
The spatial regulation of terpene synthase gene
expression qualitatively contributes to terpene
composition 35. Thus, the occurrence of certain
molecules in higher amounts such as α-pinene
could be attributed to their presence in roots oil.
Other factors potentially responsible for the chemi-
cal profile obtained of S. glaucus ssp. corono-
pifolius oil are a complex of genetic and/or
environmental interactions 36.
There is a similarity between S. glaucus ssp.
coronopifolius and other Senecio species in
terms of the main constituents of EOs. α-pinene
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930
(26.2 %) and p-cymene (9.9 %), which are major
compounds of the oil have been reported as the
main constituents in other species at different
amounts. S. farfarifolius Boiss. Et Kotschy EO
from Turkey was reported to contain á-pinene at
a higher percentage (48.3 %) 37, and EO of S.
ambavilla (Bory) Pers. from France contained
α-pinene at a lesser amount (14 %) 38, while p-
cymene was found in EO of S. nutans Sch. Bip,
grown in the Luara region of Peru, Southern
America at 8.8 % 39.
Analysis of R. segetum oil led to identification
of sixty-one components, accounting for 84.7 %
of the total constituents. 74.4 % of the total identi-
fied compounds were terpenic. Of the terpenes,
monoterpene hydrocarbons were the main class
(40.1 %), which comes in agreement with previous
studies 12,15,16,19,21,22,23, followed by sesquiterpene
hydrocarbons (17.1 %), oxygenated sesqui-
terpenes (14.7 %) and oxygenated monoterpenes
(2.5 %). (Z)-β-ocimene (19.7 %) was the main
constituent of the oil followed by β-phellandrene
(9.6 %), β-pinene (8.6 %), tricyclo [5.1.0.0(3,5)]
octane-2,6-dione, 1,3,4,5,7,8-hexamethyl-(7.0 %),
di-epi-α-cedrene (5.4 %), cubenol (2.9 %) and
alloaromadendrene (2.5 %) (Table 2).
Reports on EO derived from aerial parts of R.
segetum show α-phellandrene, terpinolene, β-
phellandrene, p-cymene, β-pinene and (Z)-β-
ocimene to be characteristic constituents of leaves,
flowers and stem oils. In concordance, the present
study identified (Z)-β-ocimene, β-phellandrene
and β-pinene as the most abundant constituents,
whilst α-phellandrene and terpinolene were
detected at trace (0.1 %) levels, presence at such
a level indicates they serve an activator function
amongst the compound family. Further, consti-
tuents found in fruit oil (phenylpropanoids
myristicin, dillapiole, and piperitenone oxide)
13,15,16,23,40
were not detected in R. segetum oil of
the present study, indicating a region specific
chemotype. α-Phellandrene was reported as the
main constituent of aerial parts of R. segetum oil
in Italy, Portugal, Spain and Tunisia at 53.3 %,
63.3 %, (39.4-69.5 %) and (34.7-47.8 %) respecti-
vely 12,16,19,22. The present study seminally identi-
fies and reports (Z)-β-ocimene as the number one
compound in R. segetum oil derived from aerial
924
parts. The profile of the current work indicates a
distinct chemotype of R. segetum, which may be
specific to Moroccan ecotypes.
Variation in chemical composition of R. segetum
EO according to geographical origin reveals
differences among countries, and also between
different collection sites within each country. In
Tunisia, flower oil of the species collected from
the region of Kroussia contained α-phellandrene
(34.7 %) and terpinolene (23.7 %) as the main
constituents 19 , whereas the EO of flowers
collected from the region of Ouled Alouène was
reported to be dominated by dillapiole (29.5-85.4
%) and myristicin (13.1-31.5 %) 20. In Spain, EO
of leaves collected from Andalucia province was
dominated by α-phellandrene (61.8-69.5 %) 16,
whereas the oil of leaves collected from Castilla
la Mancha province was dominated by p-cymene
(8.8-83.6 %) 23. Stem oil from Andalucia province
contained mainly α-phellandrene (39.4-62.0 %)
16
, whilst stem oil of the species from Castilla la
Mancha province was seen to be dominated by
p-cymene (15.1-79.5 %) 23. Analysis of Moroccan
R. segetum fruit EO showed myristicin (70.2 %)
and γ-terpinene (8.2 %) to be major compounds
40
. Although, fruits were used in the current study
for extraction of EO, γ-terpinene was detected
only in traces (0.1 %) whereas myristicin was
not detected, probably owing to a difference in
regions of plant collection. El Karkouri et al. 40
documented R. segetum from the north-west of
Morocco, whereas the present study was carried
out on plant material from the south-west. A
gradient from a cooler, humid climate to hotter,
drier climes exists from northern to southern
regions. Consequently, local ecological factors act
on the biochemical pathways of terpene production
41
, contributing to the appearance of different
chemical profiles 42.
The choice of organ used for extraction also
influences composition of R. segetum oil. In Spain,
the oil extracted from leaves and stems was
characterized by the compounds p-cymene (8.8-
83.6 %) and (Z)-β-ocimene (traces-38.5 %). The
flowers oil was dominated by α-phellandrene
(32.0-33.8 %) and terpinolene (18.0-21.4 %), and
the fruits oil contained mainly dillapiole (5.1-39.6
%) and β-pinene (10.3-20.9 %) 23. Likewise,
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 925
Table 2. Chemical composition of the essential oil isolated
from the aerial parts of Ridolfia segetum (L.) Moris

No. Compound RIexp RI lit Relative

content (%)

1 α-Thujene 922 924 0.3

2 Camphene 943 946 0.5
3 Carane, 4,5-epoxy-, trans 948 - 0.1
4 β-Pinene 973 974 8.6
5 α-Phellandrene 1000 1002 0.1
6 o-Cymene 1019 1022 1.0
7 β-Phellandrene 1023 1025 9.6
8 (Z)-β-Ocimene 1031 1032 19.7
9 (Z)-β-Ocimene 1038 1032 0.1
10 γ-Terpinene 1050 1054 0.1
11 Terpinolene 1082 1086 0.1
12 Camphenone, 6- 1094 1095 0.1
13 α-Campholenal 1125 1122 0.3
14 Pinocarveol 1131 1135 0.3
15 cis-Verbenol 1136 1137 0.4
16 Pinocarvone 1157 1160 0.1
17 Ethanone, 1-(1,4-dimethyl-3-cyclohexen-1-yl)- 1161 - 0.1
18 Terpinen-4-ol 1173 1174 0.5
19 Naphthalene, 1,2,3,4,4a,5,8,8a-octahydro- 1177 1178 0.5
4a-methyl-, trans-
20 α-Terpineol 1183 1186 0.2
21 (-)-Myrtenol 1191 1194 0.3
22 cis-Carveol 1226 1226 0.1
23 Isoaromadendrene epoxide 1281 - 0.3
24 Ledene oxide-(II) 1293 - 0.1
25 1H-Indene, 2,3,3a,4,7,7a-hexahydro-2,2,4, 1367 - 0.1
4,7,7-hexamethyl-, trans-
26 Copaene 1371 1374 0.3
27 trans-2-Dodecen-1-ol, pentafluoropropionate 1383 - 0.1
28 Longipinene 1400 1400 1.2
29 (+)-Calarene 1403 - 1.0
30 Di-epi-α-Cedrene 1407 1410 5.4
31 Cadala-1(10),3,8-triene 1423 - 0.5
32 α-Guaiene 1436 1437 0.6
33 2-Butanone, 4-(2,6,6-trimethyl-2- 1445 - 0.1
cyclohexen-1-ylidene)-
34 Geranyl acetone 1451 1453 0.2
35 Bicyclo[5.3.0]decane, 2-methylene-5- 1456 - 0.5
(1-methylvinyl)-8-methyl-
36 Alloaromadendrene 1456 1458 2.5
37 cis-(-)-2,4a,5,6,9a-Hexahydro-3,5,5,9- 1471 - 1.1
tetramethyl (1H)benzocycloheptene
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 926
table 1. (continued).

No. Compound RIexp RI lit Relative

content (%)

38 Cycloheptane, 4-methylene-1-methyl-2- 1475 - 0.1

(2-methyl-1-propen-1-yl)-1-vinyl-
39 γ-Muurolene 1475 1478 0.6
40 3-Methyl-2-butenoic acid, 2-adamantyl ester 1492 - 0.4
41 2-(3-Isopropyl-4-methyl-pent-3-en-1-ynyl)- 1496 - 1.4
2-methyl-cyclobutanone
42 β-Himachalene 1500 1500 0.1
43 Chamigrene 1503 1503 2.0
44 α-Farnesene 1504 1505 0.4
45 Farnesene epoxide, E- 1507 1505 0.9
46 γ-Cadinene 1511 1513 0.7
47 Cubenol 1514 1514 2.9
48 Tricyclo[5.1.0.0(3,5)]octane-2,6-dione, 1522 - 7.0
1,3,4,5,7,8-hexamethyl-
49 Cyclohexanemethanol, 4-ethenyl-α, α, 4-trimethyl 1522 - 1.7
-3-(1-methylethenyl)-, [1R-(1α, 3α, 4 β)]-
50 Hedycaryol 1545 1546 0.8
51 Spathulenol 1576 1577 0.2
52 Carotol 1593 1594 0.8
53 Rosifoliol 1598 1600 0.8
54 γ-Eudesmol 1626 1630 2.1
55 Alloaromadendrene oxide-(1) 1635 1639 0.5
56 α-Bisabolol 1685 1685 1.9
57 6-Isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8, 1690 - 0.7
8a-octahydro-naphthalen-2-ol
58 5(1H)-Azulenone, 2,4,6,7,8,8a-hexahydro- 1694 - 0.6
3,8-dimethyl-4-(1-methylethylidene)-, (8S-cis)-
59 Geranyl-α-terpinene 1962 - 0.7
60 3-Ethyl-3-hydroxyandrostan-17-one 2251 - 0.1
61 Hexacosa-2,25-dione 2878 - 0.2
Monoterpene hydrocarbons [No. 1, 2, 4-11] 40.1
Oxygenated monoterpenes [No. 3, 12-18, 20-22] 2.5
Sesquiterpene hydrocarbons [No. 25, 26, 28-32, 35-39, 42-44, 46] 17.1
Oxygenated sesquiterpenes [No. 23, 24, 40, 45, 47, 49-58] 14.7
Others [No. 19, 27, 33, 34, 41, 48, 59-61] 10.3
Total 84.7

RIE = Retention indices determined on a 30m Rtx-5capillary column using a mixture of hydrocarbons (C10H22-
C40H82); RIlit = Retention indices reported in the literature 26.
Marongiu et al.15 showed that flowers and stems differences may be attributed to changes in
oils were dominated by α-phellandrene (12.9-19.4 metabolism of EO production in different plant
%) and terpinolene (11.6-20.5 %), whereas, fruits organs 43.
oil was found rich in myristicin (70.8 %). These Extraction method further influences the
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930
composition of R. segetum oil. Slight differences
in percentages of the main constituents were
noted between oils obtained with hydrodistillation,
steam distillation and supercritical CO2 extraction
15,22
. These differences can be related to the
mechanisms used in each extraction method. As
EO compounds are not fully soluble in water,
hydrodistillation causes compounds to migrate
from the inside of plant leaves up to their surface,
followed by their subsequent evaporation. Hence,
the vegetable matrix releases only low molecular
weight compounds. Whereas, supercritical CO2
enables extraction of high molecular weight com-
pounds from the plant particles 15. Duration/time-
periods of extraction affect chemical composition.
Extraction of lighter compounds such as mono-
terpene hydrocarbons contrasts with oxygenated
sesquiterpenes and heavier hydrocarbons in
extraction time 15. Major compounds of R. sege-
tum flower oil from Tunisia vary according to the
time / length of the hydrodistillation 20. Similarily,
prolonged steam distillation of Italian R. segetum
gave a chemically more diverse EO profile 44.
Chemical profiles obtained of S. glaucus ssp.
coronopifolius and R. segetum EOs may also
be an outcome of the analysis method. Variation
in the choice of the analytic method or in experi-
mental parameters of the method (such as the
type of column employed) results in dissimilarities
of the molecules detected. This comes in
agreement with findings of Fan et al.45, who
reported a difference in the coverage of EO com-
position using different columns.
Characterizing the composition of plant species
metabolites will enable decision making on
domestication and breeding programs ultimately
according to the desired essential oil profile.
Essential oils display different levels of biological
activities according to their chemical composition
42
. Chemical profiles of S. glaucus ssp. corono-
pifolius and R. segetum EOs obtained herein were
characterized by the presence of many bioactive
compounds, which might have several applications
in crop protection. Bioactivity of major compounds
of the oils α-pinene, myrcene, p-cymene, β-pinene
and (Z)-β-ocimene against phytopathogens has
been identified in several studies 46, 47, 48. Moreover,
both oils contained a high number of minor com-
927
pounds present in small quantities, which can be
decisive in inducing biological activity of the oils;
as the latter is related to the synergetic and/or
antagonistic interactions between major and minor
constituents 49. Hence, exploring these species for
their bioactivity against phytopathogens or for
production of active compounds is required as a
continuum of this study.
Conclusions
The present study investigated the chemical
composition of EOs extracted from S. glaucus
ssp. coronopifolius and R. segetum growing in
Morocco. Essential oil of S. glaucus ssp. corono-
pifolius was seen to be rich in monoterpene
hydrocarbons, with á-pinene being the major
constituent. R. segetum oil was also rich in mono-
terpene hydrocarbons, though (Z)-β-ocimene was
the main constituent of the EO. Qualitative and
quantitative differences in composition were
noticed in comparison with oils of the same species
from different countries, suggesting the existence
of chemical diversity within both species. Further
analysis such as cluster analysis and dendogram
structures are suggested to confirm that the
populations of S. glaucus ssp. coronopifolius and
R. segetum growing in Morocco are indeed new
chemotypes. Comparisons of chemical dissimilari-
ties and homologues, as well as calculations of
the matrices of genetic background of S. glaucus
ssp. coronopifolius and R. segetum enable
further investigations which facilitate under-
standing of species inter-relations and functions
50
. Comprehensive knowledge of the chemical
composition of EOs provides crucial background
to further investigations, regarding the outcome
of the oils with pathogenic life forms of fungi,
nematodes, insects and bacteria.
Conflict of interests
No potential conflict of interest was reported
by the authors.
Acknowledgments
We are grateful to the staff of the laboratory of
High-Pressure Technology and Natural Products,
São Paulo University for their assistance in provi-
ding the gas chromatography analysis.
 Khadija Basaid et al., / TEOP 23 (5) 2020 918 - 930 928
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