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Isiaka A. Ogunwande,
Abstract
The chemical composition of essential oils hydrodistilled from the leaves of Citrus aurantifolia
Swingle and Citrus reticulata Blanco from Nigeria were being reported. The main compounds of C.
aurantifolia from Ijanikin was characterized by large amounts of caryophyllene oxide (32.2%),
caryophylla-3(15),7(14)-dien-6-ol (30.0%), -pinene (7.9%) and 2,6-dimethyl-1,5,7-octatrien-3-ol
(7.3%) while the Ikotun sample was rich in limonene (44.7%) and geranial (38.2%). The oils of C.
reticulata from Ijanikin had its main compounds as pinocarvone (22.7%), trans-pinocarveol acetate
(20.0%), -thujone (12.8%) while citronellal (38.1%), (Z)--ocimene (25.9%), linalool (14.5%) and
limonene (12.2%) were the major constituents identified in Ikotun sample. The present oil samples may
represent new chemical forms of the respective plant.
Abdullatif O. Giwa-Ajeniya,
Correspondence:
Oladipupo A. Lawal
Department of Chemistry, Faculty of
Science Lagos State University, PMB 0001,
Lasu Post Office Ojo, Lagos, Nigeria.
Email: jumobi.lawal@lasu.edu.ng
1. Introduction
In continuation of our research into the volatile compositions of Nigerian flora [1], we report
the chemical compounds identified in the leaf oils of Citrus aurantifolia Swingle and Citrus
reticulata Blanco collected from two different locations within Lagos State, Nigeria. The
Key lime, C. aurantiifolia, is a species with a globose fruit; 2.55 cm in diameter that is
yellow when ripe but usually picked green commercially. It is smaller and seedier, with a
higher acidity, a stronger aroma, and a thinner rind. Extracts of the plant are known to
possess antioxidant [2, 3], anti-cholinesterase [3], anti-tuberculosis [4], antibacterial [5] and
cytotoxic [6] activities. Some of its phytochemical constituents were 5-geranyloxypsoralen, 5geranyloxy-7-methoxycoumarin, palmitic acid, 5,7-dimethoxycoumarin, 5-methoxypsoralen,
5,8-dimethoxypsoralen, 5,7-dimethoxycoumarin, 3-methyl-1,2-cyclopentanedione, 1methoxy-cyclohexene, corylone and umbelliferone [4]. Others were apigenin, rutin, quercetin,
kaempferol and nobiletin [3]. Furthermore, the limonoids identified are limonexic acid,
isolimonexic acid, and limonin [7].
Citrus reticulata, mandarin is an evergreen tree growing up to 4.5 m by 3 m. The flowers are
hermaphrodite (have both male and female organs) and are pollinated by Apomictic, insects.
The plant is self-fertile. Citrus reticulata exhibited inhibitory effects on pulmonary fibrosis
[8]
, modulate blood cholesterol profile and increase bone density of ovariectomized rats [9],
possess antioxidant effect [10, 11] and antimicrobial [11]. It is a source of natural compounds
such as citruscridone [12], citriolide-A [13], isolimonexic acid methyl ether, in addition to the
previously isolated limonin, deacetylnomilin, obacunone and ichangin [14]. The marginal
antimalarial activity of isolimonexic acid methyl ether is reported [14]. It has phenolic [11] and
flavonoids among its components [15].
Literature information on the chemical constituents of their essential oils revealed a great
variability which may have been due to several factors, among them the particular varieties
studied, the geographical location, season and environmental factors, such as soil type and
climate, genetic factors processing and extraction method and the part of the plant used to
extract the oil.
~8~
RIa
(E,E)-2,4-Hexadienal
-Thujene
-Pinene
Sabinene
-Pinene
Myrcene
-Phellandrene
Limonene
(Z)--Ocimene
2,6-dimethyl-1,5,7-Octatrien-3-ol
(E)--Ocimene
-Terpinene
Terpinolene
Linalool
-Thujone
trans-Sabinol
trans-Pinocarveol
Isoborneol
Citronellal
p-Mentha-1,5-dien-8-ol
Pinocarvone
trans--Bergamotol
Terpinen-4-ol
Geranial
Guaniol
Citronellyl formate
Bornyl acetate
trans-Pinocarveol acetate
Citronellyl acetate
Eugenol
923
929
941
976
979
986
1020
1028
1042
1045
1048
1072
1089
1101
1123
1140
1147
1156
1159
1161
1164
1171
1176
1251
1257
1276
1285
1305
1358
1365
~9~
C. aIj
5.7
7.9
1.1
0.1
7.3
2.1
0.4
1.0
0.2
0.4
2.3
-
Percentage composition
C. aIk
C. rIj
0.3
0.6
3.1
0.2
0.2
0.8
1.6
3.8
44.7
1.3
4.2
4.5
1.2
1.0
1.3
4.2
12.8
2.6
5.9
5.0
4.0
0.8
22.7
38.2
1.2
1.5
20.0
0.8
C. rIk
12.2
25.9
0.9
14.5
38.1
1.5
1.2
1.4
-
Neryl acetate
trans--Bergamotene
cis--Bisabolene
Caryophyllene oxide
-Cadinol
Caryophylla-3(15),7(14)-dien-6-ol
Guaiyl acetate
6,10,14-Trimethyl-2-pentadecanone
Total
Monoterpene hydrocarbons
Oxygenated monoterpenes
Sesquiterpene hydrocarbons
Oxygenated sesquiterpenes
Non-terpene
a Retention
1369
1419
1504
1582
1667
1670
1724
1832
1.0
1.7
32.2
30.0
2.0
96.5
12.6
0.6
2.7
67.6
13.0
4.7
96.7
46.7
50.2
-
0.3
0.6
96.2
19.8
75.5
0.9
-
92.7
39.0
56.7
-
indices to C9-C24 n-alkanes on the DB-5 column; C. aIj - C. aurantifolia from Ijanikin ; C. aIk - C. aurantifolia from Ikotun; C. rIj Citrus reticulata from Ijanikin; C. rIk - Citrus reticulata from Ikotun
Table 2: Summary of major constituents of Citrus aurantifolia and Citrus reticulata in literature
Parts
Citrus aurantifolia
Leaf
Fruit
Fruit
Peel
Peel
Leaf
Citrus reticulata
Chemical Forms I
Fruit
Peel
Peel
Peel
Peel
Peel
Peel
Peel
Peel
Origin
Major constituents
References
Nigeria
Nigeria
Cuba
India
Malaysia
Malaysia
18
19
21
22
20
20
Spain
Nigeria
Burundi
Uganda
Uganda
Uruguay
Thailand
Cuba
Tunisia
Tunisia
23
24
25
26
28
30
32
33
34
35
~10~
Peel
Peel
Peel
Chemical form II
Leaf
Chemical form III
Leaf
Chemical form IV
Leaf
Chemical form V
Leaf
Chemical form VI
Unopen flower
Half-open flower
Opened flower
Chemical form VII
Young leaf
Chemical form VIII
Mature leaf
Chemical form IX
Fruit
Chemical form X
Leaf
Flower
-
India
India
China
36
36
41
China
24
China
27
Italy
29
Turkey
31
China
China
China
37
37
37
China
38
China
38
India
39
Iran
Iran
40
40
4. Conclusions
It could be seen that there was a variation within the chemical
compositions of the studied oil samples which may attributable
to the different ecological and climatic conditions as well the
nature of the plants in the different parts of the world.
5. References
1. Lawal OA, Ogunwande IA, Bullem CA, Taiwo OT,
Opoku AR. Essential oil composition and in vitro
biological activities of three Szyzgium species from
Nigeria In: New Developments in Terpene Research
(Jinnan, H. ed.), Nova Science Publisher Inc, New York,
2014; 93-112.
2. Boshtam M, Moshtaghian J, Naderi G, Asgary S, Nayeri
H. Antioxidant effects of Citrus aurantifolia (Christm)
juice and peel extract on LDL oxidation. Journal of
Research in Medical Science 2011; 16(7):951-955.
3. Loizzo MR, Tundis R, Bonesi M, Menichini F, De Luca
D, Colica C et al. Evaluation of Citrus aurantifolia peel
and leaves extracts for their chemical composition,
antioxidant and anti-cholinesterase activities. Journal of
Science of Food and Agriculture 2012; 92(15):2960-2967.
4. Sandoval-Montemayor NE, Abraham G, ElizondoTrevio E, Garza-Gonzlez E, Laura A, Mara del RC.
Chemical composition of hexane extract of Citrus
aurantifolia and anti-Mycobacterium tuberculosis activity
of some of its constituents. Molecules 2012; 17(9):1117311184.
5. Taiwo SS, Oyekanmi BA, Adesiji YO, Opaleye OO,
Adeyeba OA. In vitro antibacterial activity of crude
extracts of Citrus aurantifolia Linn and Tithonia
diversifolia Poaceae on clinical isolates. International
Journal of Tropical Medicine 2007; 2(4):113-117.
6. Asnaashari S, Abbas D, Bohlol H, Roghayeh V, Lutfun N,
Sanaz H et al. Essential oil from Citrus aurantifolia
7.
8.
9.
10.
11.
12.
13.
14.
~11~
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
~12~