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Constituents and biological activity of Citrus aurantium amara L. essential oil

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América Quintero at Universidad Nacional Experimental del Táchira
América Quintero
C.N. De Gónzalez
C.N. De Gónzalez
C.N. De Gónzalez
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F. Sánchez
F. Sánchez
F. Sánchez
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Usubillaga Alfredo at University of the Andes
Usubillaga Alfredo
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Abstract

Citrus aurantium amara L. belongs to the order Geraniales and family Rutaceae. It is native to South East Asia, and it is a wild crop in Venezuela. It is a tree 6 to 8 m high bearing fruits with a thick, rugged and easily detachable cortex. The essential oil obtained from the cortex of C. aurantium amara has been used to add aroma to beverages and liquors and as an ingredient to give fragrance to soaps, detergents, cosmetics and perfumes. The fruits were collected in several sites of Tachira State, Venezuela. The oil was extracted from the cortex by cold pressing. Its components were analyzed by gas chromatography with flame ionization detector and gas chromatography-mass spectrometry. The main constituents found were the following: monoterpenes (limonene, 77.90%; β-pinene, 3.40%; myrcene, 1.81%; and trans-ocimene, 1.16%), sesquiterpenes (valencene, 0.52%), aldehydes (decanal, 3.51%; dodecanal, 0.36% and geranial, 0.29%), alcohols (β-nerolidol, 0.85% and linalool, 0.89%), and nootkatone as the only ketone. The extraction procedure can be considered as adequate since the oil obtained does not contain p-cimene, which is an indicator of oxidation of monoterpenes in citrus essential oils. Terpinene-4-ol, a product of limonene degradation, was found in traces and thus no unpleasant odor was present. The biological activity of C. aurantium amara essential oil against Escherichia coli, Stapylococcus aureus and Pseudomonas was determined using filter paper disks impregnated with 20 ul of essential oil placed on agar plates inoculated with these bacteria (107 UFC). The biological activity was evaluated after 48 hours, being inactive against E. coli and Pseudomonas and moderately active (17 mm) against S. aureus. The results obtained confirmed the traditional properties of the essential oil studied as savoring, odor, and a perfume base, as well as a natural antiseptic to inhibit S. aureus growth.
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115
Constituents and Biological Activity of Citrus aurantium amara L.
Essential Oil
A. Quintero, C.N. Gónzalez de and F. Sánchez
Universidad Nacional Experimental del
Táchira (UNET)
Decanato de Investigación. San Cristóbal,
Venezuela.
A. Usubillaga and L. Rojas
Universidad de los Andes (ULA)
Instituto de Investigaciones
Facultad de Farmacia, Mérida Venezuela.
Keywords: essential oil, hydrodistillation, CG-MS, Citrus aurantium amara,
antimicrobial activity.
Abstract
Citrus aurantium amara L. belongs to the order Geraniales and family
Rutaceae. It is native to South East Asia, and it is a wild crop in Venezuela . It is a
tree 6 to 8 m high bearing fruits with a thick, rugged and easily detachable cortex.
The essential oil obtained from the cortex of C. aurantium amara has been used to
add aroma to beverages and liquors and as an ingredient to give fragrance to soaps,
detergents, cosmetics and perfumes. The fruits were collected in several sites of
Táchira State, Venezuela. The oil was extracted from the cortex by cold pressing. Its
components were analyzed by gas chromatography with flame ionization detector
and gas chromatography-mass spectrometry. The main constituents found were the
following: monoterpenes (limonene, 77.90%; β-pinene, 3.40%; myrcene, 1.81%; and
trans-ocimene, 1.16%), sesquiterpenes (valencene, 0.52%), aldehydes (decanal,
3.51%; dodecanal, 0.36% and geranial, 0.29%), alcohols (β-nerolidol, 0.85% and
linalool, 0.89%), and nootkatone as the only ketone. The extraction procedure can
be considered as adequate since the oil obtained does not contain p-cimene, which is
an indicator of oxidation of monoterpenes in citrus essential oils. Terpinene-4-ol, a
product of limonene degradation, was found in traces and thus no unpleasant odor
was present. The biological activity of C. aurantium amara essential oil against
Escherichia coli, Stapylococcus aureus and Pseudomonas was determined using filter
paper disks impregnated with 20 µl of essential oil placed on agar plates inoculated
with these bacteria (107 UFC). The biological activity was evaluated after 48 hours,
being inactive against E. coli and Pseudomonas and moderately active (17 mm)
against S. aureus. The results obtained confirmed the traditional properties of the
essential oil studied as savoring, odor, and a perfume base, as well as a natural
antiseptic to inhibit S. aureus growth.
INTRODUCTION
Citrus aurantium amara L (Rutaceae) is a tree 6 to 8 meters high which has fruits
with a thick outer coat. This rind is wrinkled, full of points, and peels off easily. The pulp
is acid and very bitter. The flowers are white and are located, alone or in groups, at the
axillas of the leaves. It is native to Southeast Asia and it has been introduced into all
tropical countries. The essential oil of its rind is used to aromatize liquors, beverages,
soaps, and detergents, and as an ingredient of cosmetics and perfumes.
Venezuela is one of the main citrus producing countries in South America and it
has a well developed industry of juices and citrus concentrates but it imports every kind
of citrus byproduct, including essential oils. In Táchira State a great variety of citrus is
cultivated and Citrus aurantium grows quite well.
The aim of the present work is to identify the components of the essential oil from
the rind of Citrus aurantium growing in Táchira State and to assess its biological activity.
MATERIALS AND METHODS
The essential oils were obtained by cold pressing the fruits (Mondelo et al, 1995).
GC-FID analysis was performed on two capillary columns of different polarity: dimethyl-
Proc. Int. Conf. on MAP
Eds. J. Bernáth et al.
Acta Hort. 597, ISHS 2003
116
polysiloxane and 20M-polyethylenglycol (Carbowax). Both columns were 60 m long with
0.25 mm diameter and 0.25 µm film. The oven temperature was programmed from 60o C
(5 min) to 200o C at 4o C/min and the final temperature kept for 20 min. Injector and
detector temperatures were 200o C and 220o C, respectively. The Kovats retention indices
were determined relative to the retention times of n-paraffin hydrocarbons with a
logarithmic scale.
GC-MS analysis was carried out on a model 5973 Hewlett Packard system fitted
with a 5% diphenyl-dimethyl-polysiloxane column 30 m x 0.25 mm x 0.25µm film. The
oven temperature was programmed from 60o C (3min) to 200o C (4 min) at 4o C/min. The
injector and transference line temperatures were kept at 200o C and 280o C respectively.
The ionization voltage used was 70 ev. Identification of oil components was established
using a Wiley MS Data Library and retention indices.
Biological activity of Citrus aurantium amara oil against Escherichia coli,
Staphylococcus aureus, and Pseudomonas sp, was determined by means of triplicate
assays performed according to Janssen et al. (1987). Filter paper discs impregnated with
20 µL of the oil were located on agar plates inoculated with the above mentioned
microorganisms (107 UFC). After 48 hours the activity was evaluated by measuring the
inhibition halos (mm).
RESULTS AND DISCUSSION
Table 1 presents the constituents of the essential oil of Citrus aurantium amara
distributed according to functional class. A total of 23 compounds were identified which
represent 94.8% of the oil. Monoterpene hydrocarbons represent the main oil fraction
(85.4%) and limonene (77.9%) is the most abundant constituent. All monoterpene
hydrocarbons found have been reported for the oil of Citrus aurantium amara and similar
species (Pino et al. 1999), and their relative concentrations agree with previous studies
(Njoroge et al. 1995; Dugo et al 1993; Lawrence 1994). Carvone, which is indicative of
decomposition, was not detected. This means that extraction and storage were oxidation
free (Ojeda et al. 1998).
The essential oil of C. aurantium amara was inactive against Escherichia coli and
Pseudomonas sp and moderately active (17 mm) against Staphylococcus aureus. These
results agree with those reported by Mazzanti et al (1998) who found that limonene
inhibits S. aureus.
ACKNOWLEDGEMENTS
The authors wish to thank to Mr Jorge Oliveros for his technical assistance. The
research was supported by the Decanato de Investigación de la UNET.
Literature Cited
Dugo, G., Verzera, A., d’Alcontres, I., Controneo, A. and Ficarra, R. 1993. On the
Genuine of Citrus Essential Oils. Part. LXI. Italian Bitter Orange Essential Oil:
Composition and Detection of Contamination and Additions of Oils and Terpenes of
Sweet Orange and of Lemon. Flav. Frag. J. 8:25-33.
Janssen, A.M., Scheffer, J.J.C. and Svendsen, A.B. 1987. Antimicrobial Activity of
Essential Oil: A 1976-1986 Literature Review. Planta Médica 53:395-398.
Lawrence, B.M. 1994. Progress in Essential Oils. Perfumer and Flavorist 19:33-40.
Mazzanti, G., Betinelli, L. and Salvatore, G. 1998. Antimicrobial Properties of the
Linalool-Rich Essential Oil. Flav. Frag. J. 13:289-294.
Mondello, L., Dugo, P. and Bartle, K. 1995. Automated HPLC-HRGC: A Powerful
Method for Essential Oils Analysis. Part. V. Identification of Terpene Hydrocarbons
of Bergamot, Lemon, Mandarin, Sweet Orange, Grapefruit, Clementime and Mexican
Lime Oils by Coupled HPLC-HRGC-MS (ITD). Flav. Frag. J. 10:33-42.
Njoroge, S., Ukeda, H., Kusunose, H. and Sawamura, M. 1995. Japanese Sour Citrus
Fruits. Part. III. Volatile Constituens of Sudachi and Mochiyuzu oils. Flav. Frag. J.
10:341-347.
117
Ojeda, de R,G., Morales, de G,V. and González, de C,N. 1998. Composition of
Venezuelan Lemon Essential Oil Citrus lemon, Ciencia 15:343-349.
Pino, J.A., Acevedo, A.; Rabelo, J., González, C. and Escandon, J. 1999. Chemical
Composition of Distilled Grapefruit Oil. J. Essent. Oil Res. 11:75-76.
Tables
Table 1. Constituents of the essential oil from Citrus aurantium amara L.
Compound Percenta
g
e Compound Percenta
g
e
Monoterpene
Hydrocarbons
85,42
Alcohols
2,09
α-Pinene 0,48 Linalool 0,89
Sabinene 0,62 Terpinen-4-ol 0,11
β-Pinene 3,40 Nerol 0,24
Myrcene 1,81 β-Nerolidol 0,85
Limonene 77,90
Trans-Ocimene 1,16 Esters 4,92
γ-Terpinene
0,05 Octyl Acetate
Linalyl Acetate 0,27
4,01
Sesquiterpene
Hidrocarbons
0,70 Neryl Acetate 0,22
β-Copaene 0,18 Geranyl Acetate 0,42
Valencene 0,52
Aldehydes
1,23
Ketone
Nootkatone 0,41
0,41
Citronellal 0,02
Decanal 0,51
Neral 0,05
Geranial
Dodecanal 0,29
0,36
... As seen on Table 3, Ammar et al. [27], Hsouna et al. [7] and Salma et al. [6] reported that the C. aurantium EO can be characterized by the dominance of limonene (27.5-77.90%), while no significant quantity was detected in the Venezuelan essential oil [28] and hydrodistillated Iran essential oil [29]. Conversely, Linalool, the main component of the Cyprus C. aurantium EO (15.72%), has been found in very low quantites comparing with the Iranian oil (40.65%) and French oil (40%) reported by Rahimi et al. [29] and Jeannot et al. [17], respectively. ...
... Referring to the literature, the antimicrobial potential of the studied EO and active extracts can be attributed to the presence of major (quinic acid, benzoic acid, pentadecanoic acid, myristic acid [31], dotriacontane, tetrapentacontane [12], b-pinene, linalool, a-terpineol [26], b-myrcene, d-limonene, b-ocimene, nerol, nerolidol, farnesol [3,27,32], linalyl acetat, hotrienol, trans-caryophyllene [10,28] and minor (hexadecanoic acid ester, benzoic acid methyl ester [31], phytol, squalene [28], spathulenol, b-stigmasterol, retinol, caryophyllene oxide [10,28] compounds, which are known to have effective antimicrobial properties. The synergistic effects of the diversity of major and minor compounds present in the EOs and ethanol extract should be taken into consideration to account for the bioactivity. ...
... Referring to the literature, the antimicrobial potential of the studied EO and active extracts can be attributed to the presence of major (quinic acid, benzoic acid, pentadecanoic acid, myristic acid [31], dotriacontane, tetrapentacontane [12], b-pinene, linalool, a-terpineol [26], b-myrcene, d-limonene, b-ocimene, nerol, nerolidol, farnesol [3,27,32], linalyl acetat, hotrienol, trans-caryophyllene [10,28] and minor (hexadecanoic acid ester, benzoic acid methyl ester [31], phytol, squalene [28], spathulenol, b-stigmasterol, retinol, caryophyllene oxide [10,28] compounds, which are known to have effective antimicrobial properties. The synergistic effects of the diversity of major and minor compounds present in the EOs and ethanol extract should be taken into consideration to account for the bioactivity. ...
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... The monoterpenes are the main secondary metabolites found in C. aurantium essential oil [30]. They process several functions in plant physiology and cell membranes and are attributed to biological and medical benefits, including antioxidant, antibacterial, anticancer, antidiabetic, anti-obesity, and anxiolytic effects. ...
... Limonene was the major constituent and representative of 93.79% of the total oil and concentration of the 3.3 mg/mL sample. Our findings are in accordance with previous studies indicating that C. aurantium essential oil extracted from peel contains amounts of limonene ranging from 49-94% [19,20,22,30]. Limonene is the major component in Citrus spp. ...
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... Citrus aurantium (bitter orange) is a plant belonging to the family Rutaceae. The citrus plant is a native to Southeast Asia but it is also found in all tropical, subtropical country and as a wild crop in Venezuela (Quintero et al., 2003). C. aurantium is also known as seville orange, sour orange or bitter orange, because it tastes bitter and is orange. ...
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Antimicrobial Properties of the Linalool-Rich Essential Oil
  • Jan 1998
  • 289-294
  • G Mazzanti
  • L Betinelli
  • G Salvatore
Mazzanti, G., Betinelli, L. and Salvatore, G. 1998. Antimicrobial Properties of the Linalool-Rich Essential Oil. Flav. Frag. J. 13:289-294.