South African Journal of Botany 99 (2015) 103–106

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South African Journal of Botany

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Chemical composition and antibacterial activity of Ruta graveolens L.

(Rutaceae) volatile oils, from São Luís, Maranhão, Brazil
J.F. França Orlanda a,⁎, A.R. Nascimento b
a
Maranhão State University (UEMA), Campus of Imperatriz, Chemistry and Biology Department, Laboratory of Environmental Biotechnology LABITEC,
Godofredo Viana Street, 1300 Center, 65901-480 Imperatriz, MA, Brazil
b
Maranhão State University (UFMA), Campus of Bacanga, Technology Center, Chemical Technology Department, Technology Pavilion, Portugueses Avenue, s/n,
Bacanga 65040-080 São Luís, MA, Brazil

a r t i c l e i n f o a b s t r a c t

Article history: This study investigated the chemical composition and antibacterial activities of volatile oil isolated from the fresh
Received 6 November 2014 leaves of Ruta graveolens L., Rutaceae, from São Luís, Maranhão, Brazil. The essential oil was isolated
Received in revised form 21 March 2015 using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC–MS. Seven
Accepted 25 March 2015
compounds representing 100% of the oil were identified. The main compounds were 2-nonanone (39.17%) and
Available online xxxx
2-undecanone (47.21%). Antibacterial activity against Gram-positive and Gram-negative bacteria with inhibition
Edited by I Vermaak zones of 8.30–25.60 mm to MIC values of 0.75–1.40 μg·mL−1, the most susceptible bacterium was Bacillus cereus
and Staphylococcus aureus. It is concluded from the present study that besides its traditional use, Ruta graveolens
Keywords: L. could be used as a natural source for antibacterial compounds and possible applications in the pharmaceutical
Ruta graveolens L industry.
Volatile oil © 2015 SAAB. Published by Elsevier B.V.
Antibacterial activity

1. Introduction de-smell strong, rue and rue-home-of-gardens (Lorenzi and Matos,

In recent years there has been a great scientific advance regarding
chemical and pharmacological studies of medicinal plants aimed at
obtaining new compounds with biological properties (Hossain et al.,
2012). Among the countless species of medicinal interest, there are
plants belonging to the Rutaceae family, which has species of economic,
ecological and therapeutic importance (Januário et al., 2009).
The Rutaceae family, also named as Rutaceae, belongs to the order
of Sapindales with about 150 genders and over 1600 species. They are
hugely distributed throughout the tropical and temperate regions of
the globe, being more abundant in tropical America, South Africa and
Australia (Albarici et al., 2010).
In Brazil, 33 genders and approximately 192 species are described
(Pirani and Groppo, 2010). This family is known for presenting a huge
variety secondary metabolites of strongly aromatic due to the presence
of essential oils, which has attracted the attention of several research
groups regarding its chemical and biological importance of many of
these metabolites (De La Cruz, 2008; Bizzo et al., 2009; Costa et al.,
2010; Elaissi et al., 2011).
Among the representatives of this essential oil family producers,
stand out Ruta graveolens L., popularly known as rue, rue-smelly, ruta-
⁎ Corresponding author.
E-mail addresses: fabiorlanda@yahoo.com.br (J.F. França Orlanda),
pcqaufma@yahoo.com.br (A.R. Nascimento).
2002; Anonymous, 2003), hugely used as a medicinal resource by
local people throughout Brazil (Al-Qurainy et al., 2011; Souza et al.,
2007).
In folk medicine, there are several therapeutic properties described
from R. graveolens L., which include the use of this plant in menstrual
disorders, skin inflammations, cramps, earache and headache (Mejri
et al., 2010; Ratheesh et al., 2011).
Pharmacological trials have their as anthelmintic, abortion, antipar-
asitic, healing, anti-inflammatory, anti-diarrheic, anti-rheumatic, anti-
febrile, antiulcer, vermicide repellent, anti-diabetics, anti-rheumatism
and antimicrobial properties (Yamashita et al., 2009; Ahmad et al.,
2010; Mejri et al., 2010).
In recent years, there has been a growing interest in researches
looking for possible uses of plant products as antimicrobial instead
of several synthetic antibacterial which can cause several side ef-
fects. Historically, natural products and their derivatives have been
an invaluable source of therapeutic agents. When in vitro, antimicro-
bial assays have effectively served as reliable methods to detect sev-
eral classes of secondary metabolites with high antimicrobial activity
(Silver and Bostian, 1990; Koehn and Carter, 2005; Freiesleben and
Jäger, 2014).
Antimicrobials from plant sources may exert their activity through
different mechanisms from those currently used as synthetic drugs.
Thus, they can significantly help in the treatment of resistant microbial
strains (Gardete and Tomasz, 2014).

http://dx.doi.org/10.1016/j.sajb.2015.03.198
0254-6299/© 2015 SAAB. Published by Elsevier B.V.
104 J.F. França Orlanda, A.R. Nascimento / South African Journal of Botany 99 (2015) 103–106
This paper deals with the possibility of contributing to the pharma-
cological study of this species in Brazil. Therefore, in this paper we re-
port the chemical composition and the antibacterial activities of the
essential oil from the leaves of rue, against standard strains of bacteria.
2. Materials and methods
2.1. Plant material
Aerial parts of R. graveolens L. were collected during the flowering
stage of plant, around the Maiobão region, from Paço of Lumiar,
Maranhão, Northeast of Brazil, in July 2011. The plant was identified
in the Laboratory of Botany, Chemistry and Biology Department,
Maranhão State University, Brazil. A voucher specimen (no. 107) was
deposited at the Laboratory's Herbarium.
2.2. Extraction of essential oil
The essential oil was extracted according to the method described by
Viuda-Martos et al. (2011) with few modifications. Briefly, from the
fresh plant material was ground and hydrodistilled for 4 h housing a
Clevenger-type apparatus. The oily layer obtained on top of the aqueous
distillate was separated and dried with a hydrous sodium sulfate. The oil
obtained was stored in a tight closed dark vials and covered with alumi-
num foil at 4 °C until further analysis. Essential oil was obtained with a
light green transparent liquid and had specific aroma with a 1.29 ±
0.02% (v/w) yield.
2.3. GC-FID analysis
The essential oil was analyzed using Shimadzu QP-5000 GC
equipped with flame ionization detector (FID) and HP-5MS capillary
column (30 m × 0.25 mm × 0.25 μm) in stationary phase, containing
5% of diphenyl and 95% of dimethyl polysiloxane, whose injector and
detector temperatures were maintained at 280 °C. The oven tempera-
ture was programmed from 40 °C for 5 min, raised to 240 °C at a rate
of 4 °C/min, and isotherm at 240 °C for 7.5 min. Helium was the carrier
gas, at a flow rate of 1 mL/min. A sample of 0.3 μL essential oil was
injected manually (in split mode 1:10).
2.4. GC–MS analysis
The analysis of essential oil was performed using a Shimadzu QP-5000
GC, equipped with a HP-5MS capillary column (30 m × 0.25 mm ×
0.25 μm) in stationary phase containing 5% of diphenyl and 95% of di-
methyl polysiloxane. The mass selective detector was operated in
electron-impact ionization (EI) mode with a mass scan range at 70 eV.
GC conditions were the same as described above. The retention indices
were calculated, for all volatile contents using a homologous series of n-
alkanes C8–C22. The essential oil contents were identified by comparing
their GC retention indices, mass spectra with publish data (Adams,
2007) and National Institute of Standards and Technology mass spectra
library data, provided by the software of GC–MS system. Essential oil
components are reported as a relative percentage of the total oil by
peak area.
2.5. Antibacterial activity
2.5.1. Microbial strains
The microorganisms used for antibacterial activity evaluation were
obtained from the American type culture collection (ATCC) as well as
the culture collection of the Microbiology Laboratory from Technology
Pavilion, Maranhão Federal University, Brazil. The Gram-positive bacte-
ria Staphylococcus aureus (ATCC 25923), Micrococcus flavus (ATCC
25923), Micrococcus luteus (ATCC 9341), Bacillus cereus (ATCC 11778);
Gram-negative bacteria Escherichia coli (ATCC 25922), Pseudomonas
aeruginosa (ATCC 10145), Enterobacter aerogenes (ATCC 13048) and
Salmonella typhi (ATCC 19430) were used in the antimicrobial assays.
Strains were preserved at 4 °C and grew on Luria–Bertani agar 24 h
prior to any assay. Mueller–Hinton (MH) was used for the antibiotic
susceptibility tests.
2.5.2. Antimicrobial activity assay
The essential oil was tested for the antimicrobial activity by the disk
diffusion method according to the Clinical and Laboratory Standards
Institute (CLSI, 2009), using 100 μL of suspension of tested microorgan-
isms, containing 2 × 108 CFU/mL for bacteria. Mueller–Hinton agar was
sterilized in a flask and cooled to 45–50 °C and was distributed into ster-
ilized Petri dishes with a diameter of 9 cm (15 mL). The paper-filter
disks (6 mm in diameter) were individually impregnated with 10 μL
of the oil dissolved in 0.5% at concentration (75 μg.mL− 1), and then
placed onto the agar plates which had previously been inoculated
with the tested microorganisms.
The Petri dishes were kept at 4 °C for 2 h. The plates were incubated
at 37 °C, for 24 h. The diameters of the inhibition zones (mm) were mea-
sured including the diameter of the disks. All tests were performed in
triplicate. Gentamycin (30 μg/disk), for Gram-positive bacteria, and
mikacin (30 μg/disk) – for Gram-negative – served as positive controls.
2.5.3. Determination of minimal inhibitory and minimal bactericidal
concentrations
The minimal inhibitory concentration (MIC) was determined using
the macro dilution broth method as previously described (Clinical and
Laboratory Standards Institute — CLSI, 2009). All tests were performed
in MHB. The investigated oils were dissolved in 1% of dimethyl sulfoxide
(DMSO) and then diluted until the highest concentration.
Serial doubling dilutions of oils were prepared in a 96-well micropi-
pette over the range of (0.001–75.0 μg·mL−1). Overnight broth cultures
of each strain were prepared and the final concentration in each was ad-
justed to 5 × 105 CFU/mL for bacteria. The bacteria were incubated for
24 h, at 37 and at 30 °C, respectively. The MIC is defined through the
lowest concentration of the essential oil until the microorganism does
not demonstrate visible growth. Microorganism growth was indicated
by turbidity.
2.6. Statistical analysis
In disk sensitivity, zones of inhibition were measured in millimeters
with a centimeter ruler. All the experiments were conducted in tripli-
cate and statistical analysis of data was performed by analysis of vari-
ance (ANOVA), using SPSS 21 software. All data are presented with
mean values ± standard deviation (SD). In order to satisfy ANOVA, as-
sumptions data were transformed, followed by multiple comparisons
tests.
3. Results and discussion
3.1. Chemical composition of volatile oil
The essential oil was obtained by hydrodistillation of fresh leaf sam-
ple of R. graveolens L., and produced a green color with a yield of 1.29%
(v/w). The chemical compositions of essential oil were analyzed by GC
and GC–MS and the result was presented in Table 1. In total, seven com-
ponents were identified, representing 100% of the total amount. 2-
Undecanone (47.21%), an aliphatic ketone was found as the main com-
ponent. 2-Nonanone (39.17%) was the second major aliphatic ketone de-
tected in rue oil, followed by octyl acetate (7.31%), 2-decanone (2,.03%),
diethyl phthalate (1.73%), 2-dodecanone (1.53%), pentadecanolide ace-
tate (1.02%), and others were found to be the minor components in the
essential oil.
The profile obtained in the present study was very similar to the pre-
vious results reported by Gina et al. (2008), who identified 83.4% of
 J.F. França Orlanda, A.R. Nascimento / South African Journal of Botany 99 (2015) 103–106 105

Table 1 addition, M. flavus, E. coli, M. luteus, E. aerogenes and S. typhi showed

Chemical composition of the essential oil of Ruta graveolens L. moderate antibacterial activity (p ≤ 0.01). The lowest antibacterial ac-
No. Component RI (minutes)a Percentageb Molecular formula tivity was observed against P. aeruginosa with 8.30 ± 0.05 mm zone of
1 2-Nonanone 18.15 39.17 C9H18O
inhibition (p ≤ 0.01). Results of the present study indicated the increase
2 2-Decanone 21.89 2.03 C10H20O in concentration of the essential oil which caused the increase in the
3 Octyl acetate 23.48 7.31 C10H20O2 zones of growth inhibition of each bacterium.
4 2-Undecanone 25.45 47.21 C11H22O Observing Table 2, it can be seen that the oil under study is presented
5 2-Dodecanone 27.79 1.53 C12H24O
as a potential antimicrobial agent, since the microorganisms corre-
6 Pentadecanolide acetate 29.97 1.02 C17H32O2
7 Diethyl phthalate 34.83 1.73 C12H14O4 sponding to each MIC are low ranging from 0.75 to 1.0 μg·mL−1, except
Total 100.0 for the standard strain P. aeruginosa which required 75.0 μg·mL−1 to
Bold represents the identification of chemical compounds present in the essential oil.
become sensitive to oil.
a
Retention indices (RI) relative to C5–C24 n-alkanes on HP-5MS capillary column. According to Aligiannis et al. (2001) a classification for this activity is
b
% GC peak. suggested, defining how strong MIC essential oils can hold up to
500.0 μg.mL−1, moderate for MIC 600.0–1500.0 μg.mL−1 and low for
compounds as aliphatic compounds, especially ketones, predominantly MIC above 1500 μg.mL−1. Although the essential oil presents a higher
2-undecanone (43.0%), 2-nonanone (33.5%) and lower for geijereno, MIC for P. aeruginosa 75.0 μg·mL−1, for all analyzed bacteria classified
pregeijereno, trans-anetol and isomaturnine. The major constituents as essential oil showed strong activity.
of essential oil from two samples collected from Mérida and Miranda The lower antibacterial activity against P. aeruginosa could be due to
states, Venezuela by Rojas et al. (2011), were 2-undecanone, 2- the higher resistance of Gram-negative microorganisms to those com-
nonanonae and pregeijerene. pounds. Several studies, which investigate the action of essential oil
De Feo et al. (2002) and Rustaiyan et al. (2002) reported that rue oil against pathogenic microorganisms, agree that essential oils are more
extracted growing in Venezuelan Andes (Merida), presented as the effective against Gram-positive bacteria than against Gram-negative
major compounds 2-undecanone (43.0%) and 2-nonanone (33.5%). (Kivrak et al., 2009; Oyedeji et al., 2009) as well.
Venezuelan oil showed no terpene compounds, but only the presence Regarding antimicrobial activity, rue essential oil was more effective
of aliphatic compounds (83.4%), mainly ketone (all series 2-one from against Gram-positive bacteria than Gram-negative, with the most sim-
C-8 to C-13) along with small amounts of alcohols, aldehydes, esters, ilar investigation on antimicrobial potential of volatiles (Angienda et al,
unsaturated hydrocarbons: geijereno and pregeijereno (6.2%) and 2010; Gilles et al, 2010).
aromatics: trans-anetol and isomaturnina (4.8%). The hydrophobicity of these molecules enables partitioning in the
cell membranes of microorganisms, changing their functions and turn-
3.2. Antimicrobial activity ing them more permeable. Thus, the effect as the cytoplasmic mem-
brane disruption, disruption of the flow of electrons changes in the
The antibacterial activities of R. graveolens L. oil essential against transport of molecules across the membrane, inhibiting the activity of
Gram-negative and Gram-positive bacteria are shown in Table 2. This certain enzymes and clotting cytoplasmic contents are some mecha-
method is based on the measurement of the clear zone caused by nisms involved with the promotion of antimicrobial power in essential
growth inhibition, produced by a film disk containing the antimicrobial oils described in the literature (Di Pasqua et al., 2006). Although in
agent when put in direct contact with a bacterial culture (Weerakkody most cases literature reports that phenolic compounds such as thymol,
et al., 2010). carvacrol, eugenol, anethole, and others (Burt, 2004; Bakkali et al, 2008)
The results which are indicated in Table 2 represent the zones of in- are most effective activity against microorganisms; in order to essential
hibition, and include the diameter (6 mm) of the paper disk. A broad oil of rue, which is not rich in these compounds. Methyl ketone com-
variation in the antibacterial properties of essential oil against various pounds (2-nonanone and 2-undecanone) and minority compounds
bacteria was observed. The essential oil showed strong antibacterial ac- present in chemical composition are the greatest and responsible for bi-
tivity (inhibition zone N20 mm), moderate activity (inhibition zone ological activities. The activity is due to the possibility of many forms of
b12–20 mm) and no inhibition (zone b12 mm). According to the synergistic and antagonistic interactions of many chemical compounds.
width of the inhibition zone diameter, essential oil had the highest an- This may explain its antimicrobial activity against organisms whose
tibacterial activity against B. cereus and S. aureus, with 25.60 ± 0.03 defense mechanisms are different.
and 22.00 ± 0.06 mm zone of inhibition (p ≤ 0.01), respectively. In In relation to antibacterial activity, the R. graveolens L. essential oil
obtained in Maranhão (Brazil) was more effective against Gram-
positive and Gram-negative than in the Venezuelan cities of Merida
Table 2 and Miranda (Rojas et al., 2011). This difference in antimicrobial activity
Zones of growth inhibition (mm) and MIC, showing antibacterial activity of Ruta
may be related to the presence or absence of a particular chemical com-
graveolens L. essential oil.
pound and variability of their components, especially those with alco-
Microbial strains Zone inhibition (mm)a ± MIC (μg/mL)a holic functions, aldehydic and ketonic (Belletti et al., 2004).
standard deviation From the results obtained, it can be inferred that essential oil in
Essential oil RAb Essential oil leaves of R. graveolens L. has pharmacological potential against patho-
Gram-positive genic bacteria and can be exploited to obtain bioactive compounds
Staphylococcus aureus 22.00 ± 0.06 18.20 ± 0.02 1.0 ± 0.04 and contribution for the expansion of information about this plant,
Bacillus cereus 25.60 ± 0.03 22.00 ± 0.06 1.0 ± 0,08 hugely used by the population.
Micrococcus flavus 19.00 ± 0.02 23.85 ± 0.09 0.75 ± 0.07
Micrococcus luteus 17.00 ± 0.05 21.78 ± 0.08 0.89 ± 0.08

Gram-negative 4. Conclusion
Escherichia coli 17.70 ± 0.04 19.84 ± 0.09 1.0 ± 0.04
P. aeruginosa 8.30 ± 0.05 11.51 ± 0.04 75.0 ± 0.09
S. typhi 12.40 ± 0.03 23.00 ± 0.06 1.0 ± 0.05 The volatile oil obtained from the leaves of R. graveolens L. showed
Enterobacter aerogenes 12.54 ± 0.03 16.88 ± 0.07 1.40 ± 0.14 antibacterial activity against all bacteria tested, with MIC ranging from
a
Values represent means ± standard deviations for triplicate experiments (p b 0.05).
0.75 to 1.40 μg·mL−1, except for the standard strain P. aeruginosa
b
RA, reference of antibiotics gentamicin for Gram-positive bacteria and mikacin for which required 75.0 μg·mL−1 to become sensitive to oil. Activity dem-
Gram-negative bacteria used was 30 μg/disk. onstrated here requires further investigation and points that natural
106 J.F. França Orlanda, A.R. Nascimento / South African Journal of Botany 99 (2015) 103–106
substances are present in the oil prospects for obtaining natural
antibiotics.
Acknowledgments
The authors thank Maranhão State University and Paraíba Federal
University for the laboratory support.
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