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Chemical composition and antifungal activity of essential oil and fractions extracted from the leaves of Laurus nobilis L. cultivated in Southern Brazil

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Abstract

Laurus nobilis L., popularly known as laurel, is a tree belonging to the Lauraceae family, native to Asia. It has long been used in traditional medicine to treat rheumatic disorders, and as a gastric stimulant. The aim of this study was to characterize the chemical composition of essential oils (EO) and fractions from laurel by column chromatography, and to evaluate their antifungal activity. The EO of L. nobilis leaves was obtained by hydrodistillation, and separated by column chromatography. Thirty-two EO constituents were identified, with 1,8-cineole and linalool comprising 40.14 and 15.69% of the total yield, respectively. The major constituents of the fractions (FR) were: α-terpinyl acetate (FR1: 52.65%), 1,8-cineole (FR2: 76.88%), 1,8-cineole (FR3: 84.24%), linalool (FR4: 67.26%), and linalool (FR5: 90.64%). Antifungal activity of EO and fractions were tested by a broth microdilution method, whereby minimum inhibitory concentration (MIC) was determined against several fungal organisms (Candida albicans, Candida krusei, Candida parapsilosis, Candida tropicalis, Cryptococcus gattii, and Cryptococcus neoformans). EO showed moderate inhibition of C. neoformans (MIC 0.62 mg/mL), and strongly inhibited of C. gattii (MIC 0.31 mg/mL). FR3 moderately inhibited C. neoformans (0.62 mg/mL), and strongly inhibited C. gattii (MIC 0.31 mg/mL). FR5 moderately inhibited strains of C. gattii and C. neoformans (MIC 0.62 mg/mL). Laurel ́s EO and the fractions analyzed in this study were confirmed to have antifungal properties. However, further studies on toxicity of these substances and in vivo experiments are necessary to confirm the results presented herein.
Vol. 10(48), pp. 865-871, 25 December, 2016
DOI: 10.5897/JMPR2016.6291
Article Number: C9CCEE862182
ISSN 1996-0875
Copyright © 2016
Author(s) retain the copyright of this article
http://www.academicjournals.org/JMPR
Journal of Medicinal Plants Research
Full Length Research Paper
Chemical composition and antifungal activity of
essential oil and fractions extracted from the leaves of
Laurus nobilis L. cultivated in Southern Brazil
Carla M. M. Fernandez-Andrade1, Maurício F. da Rosa1, Édela Boufleuer1, Fabiana Borges
Padilha Ferreira2, Camila Cristina Iwanaga2, José E. Gonçalves3, Diógenes A. G. Cortez4,
Cleide Viviane Buzanello Martins1, Giani Andrea Linde5, Márcia R. Simões1, Viviane S. Lobo6
and Zilda C. Gazim5*
1Postgraduate Program in Pharmaceutical Sciences, State University of Western Paraná, Cascavel, Paraná, Brazil.
2Postgraduate Program in Pharmaceutical Sciences, State University of Maringá, Maringá, Paraná, Brazil.
3Postgraduate Programs in Clean Technologies and Health Promotion, Cesumar University, Maringá, Paraná, Brazil.
4Postgraduate Programs in Health Promotion, Cesumar University, Maringá, Paraná, Brazil.
5Postgraduate Program in Biotechnology Applied to Agriculture, Paranaense University, Umuarama, Paraná, Brazil.
6Postgraduate Program in Chemical Technologies and Biochemical Processes, Federal Technological University of
Parana, Brazil.
Received 4 November, 2016; Accepted 14 December, 2016
Laurus nobilis L., popularly known as laurel, is a tree belonging to the Lauraceae family, native to Asia.
It has long been used in traditional medicine to treat rheumatic disorders, and as a gastric stimulant.
The aim of this study was to characterize the chemical composition of essential oils (EO) and fractions
from laurel by column chromatography, and to evaluate their antifungal activity. The EO of L. nobilis
leaves was obtained by hydrodistillation, and separated by column chromatography. Thirty-two EO
constituents were identified, with 1,8-cineole and linalool comprising 40.14 and 15.69% of the total yield,
respectively. The major constituents of the fractions (FR) were: α-terpinyl acetate (FR1: 52.65%), 1,8-
cineole (FR2: 76.88%), 1,8-cineole (FR3: 84.24%), linalool (FR4: 67.26%), and linalool (FR5: 90.64%).
Antifungal activity of EO and fractions were tested by a broth microdilution method, whereby minimum
inhibitory concentration (MIC) was determined against several fungal organisms (Candida albicans,
Candida krusei, Candida parapsilosis, Candida tropicalis, Cryptococcus gattii, and Cryptococcus
neoformans). EO showed moderate inhibition of C. neoformans (MIC 0.62 mg/mL), and strongly
inhibited of C. gattii (MIC 0.31 mg/mL). FR3 moderately inhibited C. neoformans (0.62 mg/mL), and
strongly inhibited C. gattii (MIC 0.31 mg/mL). FR5 moderately inhibited strains of C. gattii and C.
neoformans (MIC 0.62 mg/mL). Laurel´s EO and the fractions analyzed in this study were confirmed to
have antifungal properties. However, further studies on toxicity of these substances and in vivo
experiments are necessary to confirm the results presented herein.
Key words: Laurus nobilis, antifungal, linalool, 1,8-cineole.
INTRODUCTION
Infectious diseases caused by fungi are responsible for
morbidity and mortality in thousands of hospitalized and immune compromised individuals annually (Lemke et al.,
2005; Alangaden, 2011). Therefore, the development of
novel antifungal drugs is of vital importance. Patients with
human immunodeficiency virus infection (HIV infection/
AIDS) comprise a highly susceptible group, and the
number of opportunistic infections reported for this group
has increased dramatically (Omoruyi et al., 2014).
Cryptococcosis, a systemic mycosis caused by yeasts of
the Cryptococcus genus, most commonly Cryptococcus
gattii and Cryptococcus neoformans, is the third most
prevalent disease in people with HIV infection/ AIDS
(Gullo et al, 2013; Maziarz and Perfect, 2016). These
agents are responsible for cryptococcal meningitis, a
disease most commonly diagnosed in sub-Saharan
Africa, where it may kill more people each year than
tuberculosis. Globally, one million new cases of
cryptococcosis are estimated to occur in HIV-positive
individuals annually, resulting in nearly 624,700 deaths,
most due to meningitis (Park et al., 2009).
Additionally, the Candida yeasts are of clinical
importance, causing opportunistic infections. Candidemia
(disseminated hematogenous infection) or deep-seated
infection in normally sterile body sites of
immunosuppressed patients cause high morbidity and
mortality, and also increase medical costs by increasing
the duration of hospitalization (Patterson, 2005;
Alangaden, 2011; Menezes et al., 2012). C. albicans is
one of the major causes of infection of skin and mucosal
surfaces, it can infect any organ and in cases of
infections in the bloodstream can lead to death, if left
untreated (Noble and Johnson., 2007; Duggan et al.,
2015). Another species of great importance is C.
parapsilosis, which has recently emerged as the second
most commonly isolated species in candidemia, infects
groups such as neonates, transplant patients, and
individuals receiving parenteral nutrition. C. parapsilosis
has the ability to form biofilms with high affinity for
intravascular and parenteral nutrition devices, being more
prevalent than C. albicans in patients using such devices
(Trofa et al., 2008; Menezes et al., 2012). C. tropicalis is
increasingly isolated from patients with hematologic
malignancies, and its presence is predictive for infection
causing mucositis and neutropenia. C. krusei is the fifth
most common species in immunocompromised patients,
with high mortality rates because of resistance to
commonly used antifungal drugs such as fluconazole
(Pfaller et al., 2008; Sipsas et al., 2009; Alangaden, 2011).
Microbial resistance develops through naturally
occurring mutations in fungal cells during prolonged
antifungal treatment, resulting in selection of the most
resistant strain (Pfaller, 2012). Resistance to drugs is a
major concern worldwide because of the limited number
of antifungal drug classes, and because the number of
patients requiring antifungal treatment is increasing
Fernandez-Andrade et al. 866
(Maubon et al., 2014). Because of the pressing need for
novel therapies to treat the fungal infections, researchers
have directed their studies toward the discovery of
natural substances with greater efficacy and lower toxicity
(Pina et al., 2012; Santos and Novales, 2012).
Secondary metabolism in plants produces many
compounds that have complex chemical structures, many
of these substances have been reported to have
antimicrobial properties as essential oils (EOs) (Edris,
2007). EOs are important natural products, being
multifunctional, well accepted by consumers, and safer
than synthetic additives. Thus, they have been targeted
for research on natural food preservation, crop protection,
pharmaceutical applications, and cosmetic production
(Bakkali et al., 2008; Okoh et al., 2010).
Laurus nobilis L. is a tree belonging to the Lauraceae
family, native to Asia. The plant is popularly known as
laurel, and is cultivated in south and southeast Brazil
(Marques, 2001; Lorenzi and Matos, 2008). Laurel is an
aromatic spice, commonly used to season recipes owing
to its aroma. Laurel leaf is also used in folk medicine as
infusions or decoctions, being considered a gastric
stimulant as well as a treatment for rheumatic disorders.
It is also used externally for rheumatism, and as an
antiseptic for dandruff and lice (Joly, 1993; Marques,
2001; Lorenzi and Matos, 2008).
Laurel leaves are widely used in the food, cosmetic,
and perfumery industries, and their essential oil (EO) is
highly valued. Large amounts of phytoactive agents are
found in EO among which is terpenes. The EO are widely
studied, and their antibacterial (Angelini et al., 2006),
antifungal (Gumus et al., 2010), antioxidant (Inan et al.,
2012), insecticidal (Sertkaya et al., 2010), antiproliferative
(Abu-Dahab et al., 2014), analgesic, and anti-
inflammatory properties (Sayyah et al., 2003) reported.
This present study was designed to evaluate the
antifungal activity of EO and fractions extracted from the
leaves of L. nobilis cultivated in Southern Brazil.
MATERIALS AND METHODS
Plant material
Fresh leaves of L. nobilis L. were collected in January 2014, in the
city of Pérola, Paraná, Brazil (23º 50’ 56.6” S 53º 41’ 06.2” W, 20
m), identified by Msc. Mayara Lautert and Camila Vanessa Buturi,
as sample number 1615, and were deposited at the Herbarium of
the State University of Western Paraná.
Essential oil extraction
Fresh leaves of L. nobilis L. were subjected to hydrodistillation in a
*Corresponding author. E-mail: cristianigazim@unipar.br. Tel: +554499679382, +554436212837 Fax: +554436212849.
Author(s) agree that this article remain permanently open access under the terms of the Creative Commons Attribution
License 4.0 International License
867 J. Med. Plants Res.
apparatus for 2 h (Fiorini et al., 1997). EO was collected, dried over
sodium sulfate, filtrated, and stored in amber-colored vials at 4°C.
After total evaporation of the solvent, the EO was weighed to
calculate oil yield (%).
Obtaining L. nobilis EO fractions
EO (4.0 g) was submitted to silica gel column chromatography and
eluted sequentially with n-hexane, dichloromethane, ethyl acetate,
methanol, and hexane: dichloromethane (9:1; 8:2; 7:3, and 5:5 v/v),
dichloromethane: ethyl acetate (9:1, 8:2, 7:3, and 5:5 v/v), and ethyl
acetate: methanol (9:1, 8:2 , 7:3, and 5:5 v/v) mixtures. The
fractions were then concentrated under reduced pressure using a
rotary evaporator (Tecnal TE-211) to reduce the volume to about
2.0 mL, transferred to amber vials, dried, and stored at 4ºC for the
duration of the experiment.
GC-MS analysis
Analysis of EO was carried out in a gas chromatograph (Agilent
7890 B) coupled to a mass spectrometer (Agilent 5977 A) equipped
with an Agilent HP-5MS capillary column (30 m × 0.250 mm × 0.25
μm), using the following conditions: injector temperature of 250°C,
injection volume 1 μL at a ratio of 1:30 (split mode), initial column
temperature of 50°C, heated gradually to 260°C at 3°C/min rate.
The carrier gas (helium) flow was set at 1 mL/min. The
temperatures of the transfer line, ion source, and quadrupole were
250, 230 and 150°C, respectively (Derwich et al., 2009; Moghtader
and Salari, 2012). Mass spectra were obtained with a scan range of
40 to 500 m/z and a solvent delay time of 3 min, and compounds
were identified based on comparison of their retention indices (RI),
obtained using various n-alkanes (C8-C25). In addition, their
electron ionization (EI) mass spectra were compared with the NIST
11.0 library spectra according to Adams (2007).
Determination of the minimum inhibitory concentration (MIC)
Minimum inhibitory concentrations (MIC) of EO were determined
against C. albicans ATCC 18804, C. krusei ATCC 20298, C.
parapsilosis ATCC 20019, C. tropicalis ATCC 750, C. gattii L21/01,
and C. neoformans H99. An 80 mg/mL of the EO solution was
prepared, diluted with 2% polysorbate 80 (tween 80) in Muller
Hinton Broth with the addition of 2% glucose for yeasts. The culture
medium (100 μL) was distributed into the wells of a microdilution
plate, and then 200 μL EO solution was added to the second well.
Following homogenization, this was transferred to the third well,
and so on until the tenth. Thus, the final concentrations obtained
were 40.00, 20.00, 10.00, 5.00, 2.50, 1.25, 0.62 and 0.31 mg/mL. A
microbial suspension was prepared in saline with turbidity
equivalent to 0.5 on the McFarland scale (1 × 108 UFC/mL). Next,
the 1:50 yeast suspension was diluted to 1:20 in Mueller Hinton
Broth modified for fungi to yield 1 × 105 UFC/mL inoculums.
Hundred microliters of the suspensions was inoculated in triplicate
into each well containing the various EO concentrations. Well 1 was
used as sterility control. The toxicity control was well 11 with 2%
polysorbate 80 in culture medium. Well 12 was used as the growth
control, where microbial suspension was added to the culture
medium. Microplates were incubated at 35°C for 24 h in aerobic
conditions. MICs were determined by examining the plates. The
lowest concentration of EO causing complete inhibition of growth
(CLSI, 2008) was reported. The same procedure was performed
with fractions of the essential oil, using an initial solution of 20
mg/ml and the fluconazole was used as positive control.
Statistical analysis
The data were subjected to analysis of variance (ANOVA) and
comparisons of means by Tukey’s test at a 5% significance level.
RESULTS AND DISCUSSION
Hydrodistillation of laurel leaves resulted in a 0.66% yield
of EO. The yield obtained is in accordance with that
reported by Lira et al. (2009), who obtained a yield
between 0.3 and 1.2% during their 15-month study.
Thirty-two different constituents were identified (Table
1). The majority were terpenoids (93.50%), followed by
phenylpropanoids (6.04%). The major terpenoid
constituents obtained were monoterpene hydrocarbons
(14.44%), oxygenated monoterpenes (78.15%),
sesquiterpene hydrocarbons (0.69%) and oxygenated
sesquiterpenes (0.21%). Oxygenated monoterpenes form
the majority of the EO, 1,8-cineole being the predominant
component (40.14%), followed by linalool (15.69%), and
α-terpinyl acetate (11.70%). Sellami et al. (2011) also
reported 1,8-cineole (61.17%) to be the major compound
in samples of fresh laurel leaf EO, and Moghtader and
Salari (2012) showed that the EO of dried laurel leaves
contained 25.7% 1,8-cineole.
Silveira et al. (2012) analyzed the EO of laurel
cultivated in Concordia (Santa Catarina - Brazil) by GC-
MS. The authors observed that the oil contained 1,8-
cineole (35.50%) as its major constituent, followed by
linalool (14.10%), α-terpinyl acetate (9.65%), and
sabinene (9.45%). The results of the present work are in
line with those reported by these authors. In Croatia,
Politeo et al. (2006) reported the major compounds in
laurel EO to be 1,8-cineole (34.9%), linalool (13.5%),
methyl eugenol (13.5%), and α-terpinyl acetate (12.2%).
Dadalioglu and Evrendilek (2004) analyzed the EO of
fresh L. nobilis leaves collected in Hatay, Turkey, and
found the major constituents to be 1,8-cineole (60.72%),
α-terpinyl acetate (12.53%), and sabinene (12.12%). The
differences in the chemical composition of EO of laurel
can be attributed to plant origin, time of harvesting, drying
processes, and other factors such as climate, soil,
vegetative stage, and processing (extraction) (Simões
and Spitzer , 2007).
The fractions tested were identified by GC-MS. The
fractions (FR) were characterized as follows: FR1;
dichloromethane: hexane (7:3) fraction composed of α-
terpinyl acetate (52.65%), 1,8-cineole (29.70%), eugenol
(4.28%), and methyl eugenol (9.52%); FR2;
dichloromethane: hexane (8:2) fraction composed of 1,8-
cineole (76.88%), methyl eugenol (21.07%), α-terpinyl
acetate (1.28%), and eugenol (0.77%); FR3;
dichloromethane: hexane (9:1) fraction composed of 1,8-
cineole (84.24%) and linalool (6.78%); FR4;
dichloromethane fraction composed of 67.26% linalool
and 1,8-cineole (19.68%); and FR5; dichloromethane:
ethyl acetate (9:1) fraction composed of 90.64% linalool
Fernandez-Andrade et al. 868
Table 1. Chemical composition of essential oil and fractions obtained from the leaves of Laurus nobilis.
Peak
RI**
% Area
Identification methods
1
931
0.25
a,b
2
937
2.53
a,b
3
952
0.05
a,b
4
978
5.71
a,b
5
981
2.36
a,b
6
997
0.32
a,b
7
1010
0.03
a,b
8
1015
0.14
a,b
9
1021
0.23
a,b
10
1029
0.37
a,b
11
1033
1.57
a,b
12
1035
40.14
a,b
13
1053
0.03
a,b
14
1063
0.61
a,b
15
1071
0.36
a,b
16
1094
0.17
a,b
17
1104
0.34
a,b
18
1106
15.69
a,b
19
1126
0.08
a,b
20
1172
0.36
a,b
21
1182
3.17
a,b
22
1195
6.22
a,b
23
1234
0.13
a,b
24
1263
0.08
a,b
25
1323
0.42
a,b
26
1355
11.70
a,b
27
1363
0.20
a,b
28
1397
0.21
a,b
29
1411
5.84
a,b
30
1424
0.44
a,b
31
1529
0.04
a,b
32
1587
0.21
a,b
Compound groups (%)
Monoterpene hydrocarbons
14.44
Oxygenated monoterpenes
78.15
Sesquiterpene hydrocarbons
0.69
Oxygenated sesquiterpenes
0.21
Phenylpropanoids
6.04
Total of identified compounds
99.54
*Compounds listed in order of elution from HP-5MS column; **RI = Retention index; aIdentification based on RI; bIdentification based on
comparison of mass spectra; n.i. = not identified.
as the major constituents.
The results for MIC tests of EO and fractions are
presented in Table 2. In order to compare the results, the
values found in this study were compared with the
classification values proposed by Aligiannis et al. (2001)
and Duarte et al. (2005) for plant materials, based on
MIC results. This classification system categorizes
materials as strong inhibitors; MIC up to 0.5 mg/mL,
moderate inhibitors; MIC between 0.6 and 1.5 mg/mL,
and weak inhibitors; MIC above 1.6 mg/mL. In the
present study, EO demonstrated low inhibition of Candida
strains, moderate inhibition of C. neoformans (MIC 0.62
mg/mL), and high inhibition of C. gattii (MIC 0.31 mg/mL).
FR1 moderately inhibited C. gattii (MIC 1.25 mg/mL).
FR3 moderately inhibited C. krusei (MIC 1.25 mg/mL)
and C. neoformans (MIC 0.62 mg/mL), and strongly
869 J. Med. Plants Res.
Table 2. Minimum inhibitory concentration (MIC) of essential oil and fractions of L. nobilis (mg/mL).
Microorganisms
Essential oil of laurel
FR 1
FR 2
FR 3
FR 4
FR 5
Candida albicans
5.00b
>10.00a
>10.00a
>10.00a
1.25c
1.25c
Candida krusei
10.00b
>10.00a
>10.00a
1.25d
2.50c
2.50c
Candida parapsilosis
5.00b
>10.00a
>10.00a
>10.00a
5.00b
2.50c
Candida tropicalis
10.00b
>10.00a
>10.00a
>10.00a
1.25c
1.25c
Cryptococcus gattii
0.31d
1.25b
5.00a
0.31d
1.25b
0.62c
Cryptococcus neoformans
0.62d
>10.00a
5.00b
0.62d
1.25c
0.62d
FR1: Dichloromethane:hexane: (7:3) was composed of α-terpinyl acetate (52.65%), 1,8-cineole (29.70%), eugenol (4.28%), and methyl eugenol
(9.52%); FR2: Dichloromethane:hexane (8:2) of 1,8-cineole (76.88%), methyl eugenol (21.07%),α-terpinyl acetate (1.28%), and eugenol (0.77%); FR3:
Dichloromethane:hexane (9:1) of 1,8-cineole (84.24%) and linalool (6.78%); FR4: Dichloromethane of linalool (67.26%) and 1,8-cineole (19.68%);
FR5: Dichloromethane:ethyl acetate (9:1) of 90.64% of linalool as the major constituents. Values are the mean ± standard deviation of the experiment
performed in triplicate. Different letters in the same line are different (p≤0.05) by Tukey’s test.
inhibited C. gattii (MIC 0.31 mg/mL). FR4 moderately
inhibited C. albicans, C. tropicalis, C. gattii and C.
neoformans (MIC 1.25 mg/mL). FR5 moderately inhibited
C. albicans and C. tropicalis (MIC 1.25 mg/mL), C. gattii
and C. neoformans (MIC 0.62 mg/mL). Both FR4 and
FR5 slightly inhibited C. krusei and C. parapsilosis.
Studies carried out by Erturk et al. (2006) showed the
antifungal activity of laurel EO against C. albicans, with
an MIC of 2.4 mg/mL. Peixoto et al. (2017) evaluated the
antifungal activity of EO of laurel collected in Brazil, and
found isoeugenol (53.5%) and myrcene (16.6%) as major
constituents. The EO showed activity against C. albicans
strains (MIC 0.25 mg/mL), C. tropicalis (MIC 0.50 and
0.25 mg/mL), C. krusei and C. glabrata (MIC 0.5 mg/mL).
The EO evaluated in the present study exhibited a higher
MIC (10.00 and 5.00 mg/mL) for Candida strains; the
differences in biological activities between these findings
and the literature may be attributable to the differences in
chemical composition of EO of laurel that directly
influences its antimicrobial activity.
Monoterpenes and sesquiterpenes with aromatic rings
and phenol groups are capable of forming hydrogen
bonds with the active sites of target enzymes, and this is
the main mode of antimicrobial action of EO. Other
compounds such as alcohols, aldehydes, and esters also
contribute to antimicrobial activity (Belletti et al., 2004).
The antifungal activity of the fractions can be attributed to
the presence of terpenes. Linalool, the major constituent
in FR 4 and FR5, was screened for activity against
Candida isolates by Marcos-Arias et al. (2011), who
reported findings against C. albicans (MIC, 0.30-2.50
mg/mL), C. tropicalis (0.60-2.50 mg/mL), C. parapsilosis
(0.30 mg/mL), and C. krusei (0.60 mg/mL). The eugenol
in FR1 and FR2, and terpinen-4-ol present in FR35
were also investigated by Marcos-Arias et al. (2011);
against C. albicans eugenol had an MIC in the range of
0.60-2.50 mg/mL, and terpinen-4-ol in the range of 0.60-
5.00 mg/mL; for C. tropicalis, the eugenol and terpinen-4-
ol MIC range was 0.60-1.20 mg/mL; for C. parapsilosis,
the MIC of both substances was 0.60 mg/mL; and for C.
krusei, both had an MIC of 1.20 mg/mL. In general, the
MIC values reported for the fractions in this study against
Candida species are close to those found by Marcos-
Arias et al. (2011), considering that they evaluated pure
substances, while the fractions in this present study are a
mixture of terpenes, which may or may not have
synergistic effects. Hsu et al. (2013) determined the MIC
against Candida species for linalool, and found it to
be1.23 to 4.93 mg/mL for C. albicans, and 2.47 mg/mL
for C. tropicalis. These values are comparable to those
found in the present study for FR4 and FR5, in which
linalool is the major compound.
1,8-Cineole is present in all fractions, and is the major
compound in FR2 and FR3 (76.88 and 84.24%,
respectively); its antifungal activity was investigated by
Adegoke et al. (2000) against Candida tropicalis yeast. It
was found to have an MIC of 0.16 mg/mL against C.
tropicalis yeast, with an activity superior to the that
recorded for the fractions containing 1,8-cineole in the
present study. However, these authors investigated the
use of pure substances. Hammer et al. (2003)
determined the MIC for 1,8-cineole against isolates of C.
albicans (40.00 mg/mL) and C. parapsilosis (80.00
mg/mL). Pattnaik et al. (1997) analyzed the antifungal
action of oxygenated linalool and 1,8-cineole
monoterpenes, and found linalool to possess activity
against C. albicans (MIC 0.20 mg/mL). C. albicans was
resistant to 1,8-cineole at MIC up 5.00 mg/mL. This
present study documented lower linalool activity in the
fractions containing it as the major compound. Fractions
containing 1.8-cineole had higher antifungal activity
against C. albicans and C. parapsilosis in comparison
with the results of the studies mentioned above; this may
be explained by the fact that fractions are a mixture of
antifungal substances acting in synergy.
To our knowledge, this is the first investigation
documenting antifungal activity of EO and fractions
extracted from fresh leaves of laurel against strains of C.
parapsilosis, C. gattii, and C. neoformans. EO extracted
and analyzed in this study, as well as its fractions,
possess antifungal properties. The presence and
proportion of the EO constituents are related to biological
properties of laurel. However, further studies on toxicity of
these substances and in vivo experiments are necessary
to confirm the results here presented.
Conflicts of Interests
The authors have not declared any conflict of interests.
ACKNOWLEDGEMENTS
The authors acknowledge financial support by the
Coordination for Improvement of Higher Education
Personnel (Coordenação de Aperfeiçoamento de
Pessoal de Nível Superior - CAPES).
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... The EO content (yield) of the laurel fruits varied within a large range, 0.60-4.30% [2][3][4][5][6][7][8][9][10], and the EO content of the leaves also varied widely, from 0.5 to 4.3% [2,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. ...
... The leaf EO was found to be rich in 1,8-cineole (30-70%), linalool (0.9-26.9%), α-terpinyl acetate (4.50-25.7%), α-pinene, β-pinene, sabinene, α-terpineol, terpineol-4, etc. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. The growing interest in natural products, such as EOs, and the inclusion of plant extracts in various cosmetic products is a prerequisite for an in-depth analysis of the chemical composition of laurel genotypes from various regions. ...
... The laurel EOs have demonstrated antimicrobial [14][15][16][17][18]24,26,29,[30][31][32][33], antioxidant [12,15,16,20,21,23,26,32,33], and pharmacological properties [13,33]. Because of its biological activity, laurel leaf EO could be considered a natural supplement or antioxidant in cosmetics [1,34] and medicine [1,8]. ...
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Laurel, Laurus nobilis L. is an evergreen plant belonging to the Lauraceae family, native to Southern Europe and the Mediterranean area. This is the first report on the composition and bioactivity of laurel essential oil (EO) from Bulgaria. The oil yield was 0.78%, 0.80%, and 3.25% in the fruits, twigs, and leaves, respectively. The main constituents in the fruit EO were 1,8-cineole (33.3%), α-terpinyl acetate (10.3%), α-pinene (11.0%), β-elemene (7.5%), sabinene (6.3%), β-phellandrene (5.2%), bornyl acetate (4.4%), and camphene (4.3%); those in the twig EO were 1,8-cineole (48.5%), α-terpinyl acetate (13.1%), methyl eugenol (6.6%), β-linalool (3.8%), β-pinene (3.4%), sabinene (3.3%) and terpinene-4-ol (3.3%); and the ones in the leaf EO were 1,8-cineole (41.0%), α-terpinyl acetate (14.4%), sabinene (8.8%), methyl eugenole (6.0%), β-linalool (4.9%), and α-terpineol (3.1%). The antibacterial and antifungal properties of laurel EOs were examined according to the agar well diffusion method. The leaf EO showed antibacterial and antifungal activities against almost all strains of the microorganisms tested, whereas the twig EO was only able to inhibit Staphylococcus aureus. Pseudomonas aeruginosa АТСС 9027 and Escherichia coli ATCC 8739 were the bacterial strains that showed the highest resistance to the laurel EO. The results can benefit the EO industry and biopesticide development.
... It has been used throughout the years as a food flavoring and in traditional medicine, because it contains a variety of bioactive and flavoring components [24]. However, several studies have proved the effect of LN aromatic oil (AO) as an antimicrobial, wound healing, antioxidant, anticonvulsant, antimutagenic, and immuno-stimulant [24][25][26][27][28][29]. The LNAO could be considered a natural supplement or antioxidant in cosmetics and medicine [30,31]. ...
Article
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Laurus nobilis (LN) has been used throughout the years as a food flavoring and in traditional medicine. The LN leaves have various biological activities, such as antioxidant, wound healing, antibacterial, analgesic, and anti-inflammatory activities. However, oxidative stress, cancer, diabetes, microbial infections, and inflammatory diseases are closely linked. The objective of this research is to characterize Laurus nobilis (LN) aromatic oil (AO) and evaluate its antioxidant, antidiabetic, antiobesity, antimicrobial, and antimutagenic bioactivities. The AO constituents were characterized using gas chromatography–mass spectrometry (GC–MS). The antimicrobial activity was performed using a microdilution assay against six common microbial species. Free radicals, a porcine pancreatic lipase, α-amylase, and α-glucosidase inhibitory assays were conducted utilizing reference biomedical methods. The cytotoxic effect of LNAO was established on a variety of cancer and normal cell lines using the MTS assay. The anti-inflammatory activity of LNAO was evaluated using the Cayman COX activity kit. The results indicate about 99% of the total oil is composed of 36 compounds, the characterized AO metabolites showed content of many oxygenated terpenoids with 1,8-Cineole and Terpinyl acetate as a major component with a percentage of (40.39 and 15.07, respectively. The plant AO showed potent antioxidant activity (IC50 = 2.2 ± 1.38) and has moderate anti-amylase (IC50 = 60.25 ± 1.25), anti-glucosidase (IC50 = 131.82 ± 0.1), and antilipase (IC50 = 83.17 ± 0.06) activities. Moreover, LNAO showed potent antimicrobial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia, Proteus vulgaris (MICs = 1.56 µg/mL), methicillin-resistant Staphylococcus aureus (MRSA) (MIC = 3.125 µg/mL) and Candida albicans (MIC = 0.195 µg/mL). The cytotoxicity results demonstrated that at a concentration of 1 mg/mL, LNAO has potent breast cancer (MCF-7), and hepatocellular carcinoma (Hep 3B) cancer cells inhibitory activities of 98% and 95%, respectively. Importantly, we are the first to show that LNAO significantly hinders hepatocellular carcinoma spheroids’ formation capacity in a 3D model. These results show that LNAO is a promising natural source with powerful antioxidant, antidiabetic, anticancer, and antimicrobial activities that could be exploited in the future to treat a variety of diseases. Graphical Abstract
... L. nobilis leaves are also used externally as an antiseptic for dandruff and lice [43][44][45]. The dried leaves of L. nobilis are used as a spice or flavoring agent in the culinary and food industries [4,46,47]. The essential leaf oil of L. nobilis is also used in the perfume and soap industries [48]. ...
Article
Background Native to the Southern Mediterranean region, Laurus nobilis L. (Family Lauraceae) is an evergreen shrub or tree found in warm climate regions with high rainfall. The leaves and essential oil of this plant have been widely used as condiments, spices, and flavoring agents in the culinary and food industries. The whole plant is also used for the traditional treatment of various diseases, including cough, asthma, hemorrhoids, rheumatic pain, diarrhea, intestinal, and cardiac diseases. Previous phytochemical investigation of this plant demonstrated the presence of a variety of secondary metabolites, especially terpenoids. Aim The present study aims to critically analyze comprehensive literature on the pharmacological activity and mechanisms of action of terpenoids from Laurus nobilis L. Methods The available information on the pharmacological activity of terpenoids from L. nobilis L. was obtained from textbooks, theses, as well as published articles through a variety of libraries and electronic databases. Results The present study demonstrated that L. nobilis is rich in terpenoids, with more than 200 entities identified in reported studies. Terpenoids from L. nobilis have shown a wide range of pharmacological activities, including anti-inflammatory, antidiabetic, antifungal, antibacterial, immunomodulatory, anticonvulsant, antioxidant and cytotoxic activities. The mechanisms of action of most of these terpenoids included the imbalance of the ionic permeability of the cell membrane (anti-inflammatory and antimicrobial activities), modulation of the effects of gamma-aminobutyric acid (GABA)nergic neurotransmission (anticonvulsant activity), and the inhibition of inflammatory responses, prevention of metastasis, and induction of apoptosis (cytotoxic effect), among others. Conclusion Referring to in vitro studies, terpenoids of L. nobilis L. have shown a variety of biological activities. However, more cytotoxic and in vivo studies and detailed mechanisms of action of the bioactive terpenoids are recommended.
... 1,8-CCineole obtained from the leaves exhibited moderate inhibitory activity against C. neoformans with MIC value 0.62 mg/mL and potent inhibitory activity against C. gattii with MIC value 0.31 mg/mL. In addition, linalool obtained from the leaves showed moderate inhibitory effect against C. gattii and C. neoformans with MIC value 0.62 mg/mL (Fernandez-Andrade et al. 2016). ...
Chapter
Laurus nobilis L. is evergreen aromatic shrubs or trees, belongs to Lauraceae family, and is cultivated because of its aromatic leaves and ornamental interest. This chapter first summarized the description and distribution of the plant. Its chemical composition and traditional use were demonstrated in detail. The biological activities of its extracts, fractions, and pure compounds have been highlighted for further studies of the researchers. Besides, its toxicity and allergenicity properties were indicated.Keywords Laurus nobilis Traditional useChemical compositionBiological activities
... Laurus nobilis or sweet bay belongs to the Lauraceae family and is grown as a high-value spice crop and as an ornamental plant in the region including Asia, Europe and America. Phytochemical analyses have revealed the presence of various compounds such as alkaloids, flavonoids, tannins, vitamins and minerals [19,20].Various researchers have found that the leaf extracts of Laurus nobilis contain high antibacterial and antifungal properties [21,22]. The leaf extract was more effective against the growth of Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli [23]. ...
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This is an Open Access Journal / article distributed under the terms of the Creative Commons Attribution License (CC BY-NC-ND 3.0) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. All rights reserved. The growth of food poisoning pathogens as well as food spoilage is usually controlled by the use of chemical preservatives which cause an adverse effect on human health. Because of such apprehension, the requirement to find a safer, potentially effective and natural alternative is increased. Inside these texts, plant-based extracts have been used to estimate their phytoconstituents and antimicrobial activity. Tannins were the principal phytoconstituents which were detected in all the extracts. Antimicrobial activity of three plant extracts was investigated against Escherichia coli (MTCC 10312), Bacillus subtilis (MTCC 9003), Pseudomonas aeruginosa (MTCC 104) and Staphylococcus aureus (MTCC 106) by using agar disc diffusion technique. Hibiscus rosa-sinensis, Laurus nobilis and Psidium guajava plant leaves showed antimicrobial activity (in respect to zone of inhibition) ranged from 8.33 to 13 mm, 8 to 13.16 mm and 7.83 to 15.33 mm respectively. The highly significant Pearson correlation indicated a symbiotic relationship among all the selected bacterial strains.
... Corato et al. [38] found laurel essential oil to be highly effective against Monilinia laxa at 200 μg/mL, B. cinerea at 1000 μg/mL, and partially effective against Penicillium digitatum. Antifungal activity against strains of Candida parapsilosis, C. gattii, and C. neoformans was confirmed [25]. Laurel essential oil had the lowest antimicrobial activities among other oils investigated in Rafiq et al. [42], and a similar result was obtained in our study. ...
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Sustainable plant protection can be applied on apples against fungal pathogens such as Botrytis cinerea (which is responsible for gray mold)-a significant global postharvest disease. This pathogen can affect a wide range of hosts; and fruits may have variable susceptibilities to B. cinerea from different plant hosts. New possibilities to control gray mold in food production are under demand due to the emergence of resistance against antifungal agents in fungal pathogens. Cinnamon, pimento, and laurel extracts were previously assessed for antifungal activities under in vitro conditions and were found to have the potential to be effective against postharvest gray mold. Therefore, this study aimed to investigate the antifungal activity of cinnamon, pimento, and laurel extracts in vitro and against postharvest gray mold on apples to determine the susceptibility of apple fruits to B. cinerea from different plant hosts, and to analyze the chemical composition of the extracts. Apples (cv. "Connell Red") were treated with different concentrations of extracts and inoculated with B. cinerea isolates from apple and strawberry followed by evaluation of in vitro antifungal activity. The results reveal that most of the concentrations of the extracts that were investigated were not efficient enough when assessed in the postharvest assay, despite having demonstrated a high in vitro antifungal effect. Apples were less susceptible to B. cinerea isolated from strawberry. To conclude, cinnamon extract was found to be the most effective against apple gray mold; however, higher concentrations of the extracts are required for the efficient inhibition of B. cinerea in fruits during storage.
... Laurus nobilis L., which is commonly known as Bay (Family Lauraceae), is an ornamental plant native in the Mediterranean region. The plant is used as a traditional spice and have been mentioned for biological activities [23][24][25][26][27][28]. The structure and properties of the synthesized nanoparticles were evaluated by FT-IR and UV-Vis spectroscopy; XRD technique, SEM and TEM electron microscopy, and EDS technique. ...
Article
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A valuable approach in green nanotechnology is the application of biomaterials in the synthesis of nanoparticles. In this project, we synthesized iron oxide nanoparticles in the phase of hematite (α-Fe2O3) by the aqueous extract of Laurus nobilis L. leaves in a simple and eco-friendly method. The nanoparticles were characterized using Ultraviolet–Visible spectroscopy (UV–Visible), Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction analysis (XRD), scanning electron microscopy (SEM), transfer electron microscopy (TEM) and energy-dispersive X-ray spectroscopy (EDS). The results showed that the nanoparticles are crystalline, almost spherical like and partly as a hexagonal shape with an average size of 8.03 ± 8.99 nm. The antimicrobial activity of the synthesized nanoparticles was evaluated against three bacteria and two fungi. The results showed that the nanoparticles are moderately effective on the Gram-positive bacterium of Listeria monocytogenes and the fungi Aspergillus flavus and Penicillium spinulosum. The nanoparticles synthesized by this green method could be potentially useful as antifungal and antibacterial compound and, may be considered as gas sensors, light photo-catalysis and, semiconductor.
Chapter
Lavender (Lavandula sp.), thyme (Thymus sp. and Thymbra sp.), oregano (Origanum sp.), savory (Satureja sp.), mints (Mentha sp.), sage (Salvia officinalis and S. sclarea), rosemary (Rosmarinus officinalis), rose (Rosa sp.), citrus (Citrus sp.), and bay laurel (Laurus nobilis) are species widely used as medicinal and aromatic plants. Their essential oils are a well-known resource of biological activities, applicable in food, cosmetic, and pharmaceutical industries, as well as in agriculture. Due to developments in ecology and sustainability during the past two decades, hydrolates, which were considered waste material for a long time, are viewed as by-products with promising activity and applications. This chapter provides a review of these ten hydrolates, their chemical composition, and potential use.
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This investigation is performed to evaluate the antifungal and anti-ochratoxigenic activities of Salvia officinalis, Lavandula dentata and Laurus nobilis essential oils (EOs), and their major constituent 1,8-cineole. The evaluation of these activities was performed by two assays, contact assay with application of different concentrations of each tested EO as well as 1,8-cineole (0, 0.1, 0.2, 0.3, 0.4 and 0.5%) in Czapek Yeast Agar medium (CYA) and volatile assay by application of one concentration of each EO equal to 0.025% of CYA. The chemical composition of tested EOs was determined through gas chromatographic-mass spectrometry analysis and their antioxidant capacity was assessed by DPPH assay. Obtained results showed that L. nobilis EO exhibited better antioxidant activity (IC50=0.35 ± 0.05mg/mL) than S. officinalis (IC50=11.12 ± 0.09mg/mL) and L. dentate (IC50=14.03 ± 0.16mg/mL) and it possessed the highest phenolic content (15.15 ± 1.64 mg gallic acid equivalent/g EO). Statistical analyses of volatile assay showed that L. nobilis EO inhibited the growth rate much more than L. dentata and S. officinalis with a percentage equal to 47.82, 37.92 and 31.71%, respectively, and reduced the production of OTA with a percentage of 88.87%. While, on contact assay L. nobilis and L. dentata EOs exhibited a higher antifungal and anti-ochratoxigenic activities than S. officinalis, with a minimum inhibitory concentration (MIC) of about 0.3, 0.3 and 0.5%, respectively. The MIC of 1,8-cineole (0.5%) was approximately double to that of L. nobilis and L. dentata EOs. Hence, its powerful biological activities were assured by the synergism between the major component and the other existing ones
Article
This investigation is performed to evaluate the antifungal and anti-ochratoxigenic activities of Salvia officinalis, Lavandula dentata and Laurus nobilis essential oils (EOs), and their major constituent 1,8-cineole. The evaluation of these activities was performed by two assays, contact assay with application of different concentrations of each tested EO as well as 1,8-cineole (0, 0.1, 0.2, 0.3, 0.4 and 0.5%) in Czapek Yeast Agar medium (CYA) and volatile assay by application of one concentration of each EO equal to 0.025% of CYA. The chemical composition of tested EOs was determined through gas chromatographic-mass spectrometry analysis and their antioxidant capacity was assessed by DPPH assay. Obtained results showed that L. nobilis EO exhibited better antioxidant activity (IC50=0.35 ± 0.05mg/mL) than S. officinalis (IC50=11.12 ± 0.09mg/mL) and L. dentate (IC50=14.03 ± 0.16mg/mL) and it possessed the highest phenolic content (15.15 ± 1.64 mg gallic acid equivalent/g EO). Statistical analyses of volatile assay showed that L. nobilis EO inhibited the growth rate much more than L. dentata and S. officinalis with a percentage equal to 47.82, 37.92 and 31.71%, respectively, and reduced the production of OTA with a percentage of 88.87%. While, on contact assay L. nobilis and L. dentata EOs exhibited a higher antifungal and anti-ochratoxigenic activities than S. officinalis, with a minimum inhibitory concentration (MIC) of about 0.3, 0.3 and 0.5%, respectively. The MIC of 1,8-cineole (0.5%) was approximately double to that of L. nobilis and L. dentata EOs. Hence, its powerful biological activities were assured by the synergism between the major component and the other existing ones.
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Five aromatic constituents of essential oils (cineole, citral, geraniol, linalool and menthol) were tested for antimicrobial activity against eighteen bacteria (including Gram-positive cocci and rods, and Gram-negative rods) and twelve fungi (three yeast-like and nine filamentous). In terms of antibacterial activity linalool was the most effective and inhibited seventeen bacteria, followed by cineole, geraniol (each of which inhibited sixteen bacteria), menthol and citral aromatic compounds, which inhibited fifteen and fourteen bacteria, respectively. Against fungi the citral and geraniol oils were the most effective (inhibiting all twelve fungi), followed by linalool (inhibiting ten fungi), cineole and menthol (each of which inhibited seven fungi) compounds.
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The present paper presents a brief review about the economic importance of family Lauraccae, which provided informations on 52 species, belonging to 12 genus, that are used in cooking, paper factoring, timber works, constructions, chemical industries and folk medicine. The genus Aniba, Ocotea and Nectandra presented the greatest number of species with economic importance. Key words: Lauraccae; Economic botany; Folk medicine
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Candida albicans is a major cause of bloodstream infection which may present as sepsis and septic shock - major causes of morbidity and mortality world-wide. After invasion of the pathogen, innate mechanisms govern the early response. Here, we outline the models used to study these mechanisms and summarize our current understanding of innate immune responses during Candida bloodstream infection. This includes protective immunity as well as harmful responses resulting in Candida induced sepsis. Neutrophilic granulocytes are considered principal effector cells conferring protection and recognize C. albicans mainly via complement receptor 3. They possess a range of effector mechanisms, contributing to elimination of the pathogen. Neutrophil activation is closely linked to complement and modulated by activated mononuclear cells. A thorough understanding of these mechanisms will help in creating an individualized approach to patients suffering from systemic candidiasis and aid in optimizing clinical management.
Article
The chemical composition of the essential oils of the leaves and the flowers of Laurus nobilis L. (Lauraceae) from Kerman province, Iran were obtained by hydrodistillation method and analyzed by gas chromatography and gas chromatography mass spectrometry. Thirty-three compounds, accounting for 95.75% of the total oil with 1.8% oil yield were identified in the essential oil of the leaves. The major components were 1,8-cineole (25.7%), Sabinene (8.7%) and α-pinene (5.25%). Twenty-seven compounds, accounting for 87.36% of the total oil with 1.2% oil yield were identified in the essential oil of the flowers. The major components were 1,8-cineole (18.69%), -elemene (8.87%), Sabinene (7.93%), α-pinene (7.38%) and -Caryophyllene (5.35%).