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Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities of essential oil of Campomanesia adamantium (Cambess.) O. Berg (Guavira)

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The essential oils from Campomanesia adamantium (Cambess.) O. Berg leaves, collected in the reproductive (flowering and fruit-bearing) and vegetative stages, were characterized by GC-MS (Gas Chromatography-Mass Spectrometry). A total of 95 compounds of the essential oils were identified. In the reproductive stage (flowering) the major constituents were monoterpenes (limonene, α-pinene and β-pinene) while during the vegetative stage the major constituents were the sesquiterpenes (bicyclogermacrene and globulol). The essential oil of the reproductive stage shows high antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans, and all show moderate activity against Escherichia coli. The essential oils were also evaluated for their radical-scavenging activity by DPPH. The chemogeographical variations of the oil composition from the four distinct localities studied all contained α-pinene, β-pinene, limonene, linalool, β-caryophyllene, germacrene D and bicyclogermacrene, however the samples from Jardim city contained neither limonene nor linalool.
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*Correspondence: R. G. Coelho. Departamento de Química, Universidade
Federal de Mato Grosso do Sul UFMS, Caixa Postal 549, 79070-900 - Campo
Grande - MS, Brazil. E-mail: robertacoelho@yahoo.com.br
Article
Brazilian Journal of
Pharmaceutical Sciences
vol. 45, n. 4, oct./dec., 2009
Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation
of antioxidant and antimicrobial activities of essential oil of
Campomanesia adamantium (Cambess.) O. Berg (Guavira)
Isabel Duarte Coutinho
1
, Claúdia Andréa Lima Cardoso
1,2
, Nilva Ré-Poppi
1
, Adriana Mestriner
Melo
3
, Maria do Carmo Vieira
4
, Neli Kika Honda
1
, Roberta Gomes Coelho
1,
*
1
Department of Chemistry, Federal University of Mato Grosso do Sul,
2
Course of Chemistry, State University of Mato Grosso
do Sul,
3
Department of Biology Science and Health, University Center of Grande Dourados,
4
Department of Agronomy,
Federal University of Grande Dourados
The essential oils from Campomanesia adamantium (Cambess.) O. Berg leaves, collected in the
reproductive (owering and fruit-bearing) and vegetative stages, were characterized by GC-MS (Gas
Chromatography-Mass Spectrometry). A total of 95 compounds of the essential oils were identied.
In the reproductive stage (owering) the major constituents were monoterpenes (limonene, α-pinene
and β-pinene) while during the vegetative stage the major constituents were the sesquiterpenes
(bicyclogermacrene and globulol). The essential oil of the reproductive stage shows high antimicrobial
activity against Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans, and all show
moderate activity against Escherichia coli. The essential oils were also evaluated for their radical-
scavenging activity by DPPH. The chemogeographical variations of the oil composition from the
four distinct localities studied all contained α-pinene, β-pinene, limonene, linalool, β-caryophyllene,
germacrene D and bicyclogermacrene, however the samples from Jardim city contained neither limonene
nor linalool.
Uniterms: Campomanesia adamantium/antioxidant activity. Campomanesia adamantium/antimicrobial
activity. Guavira. Essential oil/caracterization.
Os óleos essenciais obtidos das folhas de Campomanesia adamantium foram caracterizados através da
combinação de CG-EM e índice de retenção, sendo identicado um total de 95 compostos. Na oração
as substâncias majoritárias foram monoterpenos (limoneno, α-pineno e β-pineno) e durante o estágio
vegetativo as substâncias majoritárias foram sesquiterpenos (biciclogermacreno e globulol). Os óleos
essenciais obtidos da oração e fruticação mostraram alta atividade contra Staphylococcus aureus,
Pseudomonas aeruginosa e Candida albicans e moderada contra Escherichia coli em todos os estágios.
Foi avaliada a atividade antioxidante dos óleos essenciais usando o método do DPPH. O óleo essencial
das 4 cidades mostrou a presença de α-pineno, β-pineno, limoneno, linalol, β-carioleno, germacreno D
e biciclogermacreno, mas a amostra da cidade de Jardim não apresentou limoneno e linalol.
Unitermos: Campomanesia adamantium/atividade antioxidante. Campomanesia adamantium/atividade
antimicrobiana. Guavira. Óleo essencial/caracterização.
INTRODUCTION
Essential oils are complex mixtures of isomers such
as monoterpenes, sesquiterpenes, aromatic compounds
and aliphatic compounds (Zhao et al., 2005). Plants rich
in aromatic compounds can have ecological functions,
besides those that are used as alternative remedies for the
treatment of many infectious diseases or the preservation
of food from the toxic effects of oxidants (Tepe et al.,
2004).
Quantitative and qualitative differences in the ter-
pene compositions of some plants might be inuenced by
I. D. Coutinho, C. A. L. Cardoso, N. Ré-Poppi, A. M. Melo, M. C. Vieira, N. K. Honda, R. G. Coelho
768
different phenological stages as well as environmental
factors, as shown in the studies of Thymus vulgaris (Hu-
daib et al., 2002). For example, variations in the chemical
composition at different phenological stages have been
associated with the alteration of the chemical composition
in antimicrobial activities, e.g., studies of the essential oils
of Salvia sahendica (Salehi et al., 2007).
Nowadays, studies of the variability of compounds
in plants associated with the evaluation of antioxidant and
antimicrobial activities are important. The prevention of
cancer and cardiovascular diseases has been associated
with the ingestion of fresh fruit, vegetables or teas rich in
natural antioxidants (Ramalho, Jorge, 2006). Substances
with antimicrobial activities are used in the treatment of
infectious diseases, as well as antifungal agents in plants
that assist in the treatment of opportunistic systemic my-
coses (Rahalison et al., 1994).
Campomanesia adamantium (Cambess.) O. Berg
(Myrtaceae) is a small tree with edible fruit, commonly
known as guavira or guabiroba. A species native to the
Brazilian Cerrado bioma (Lorenzi et al., 2006), the fruit
is widely used to make liqueurs, juices and sweets. There
are few studies published about the chemical composition
of leaves of this genus.
The essential oils of the C. guazumifolia, C. rhombea
and C. xanthocarpa leaves are the most studied species
(Limberger et al., 2001), while only the essential oil from
the C. adamantium (Vallilo et al., 2004) fruit has been
studied. Studies reported the isolation of three yellow pig-
ments of the C. lineatifolia seeds, named champanones.
Terpenes were identied in volatile extracts of pulp, peel,
leaves and seeds in the same species (Bonilla et al., 2005;
Osorio et al., 2006). Chemical studies of Campomanesia
genus have identied quercetin, myricetin and rutin by
HPLC (Schmeda-Hirschmann, 1994).
This paper describes the identication of essential
oil constituents obtained at the three different phenological
stages associated with the evaluation of the antioxidant
and antimicrobial activities and variability of the chemi-
cal composition of four samples collected from different
geographical regions.
MATERIAL AND METHODS
Chemical analysis
The solvents employed in CG-MS (Gas Chromato-
graphy-Mass Spectrometry) analysis were nanopure grade
purchased from Merck (Darmstadt, Germany), whereas
n-Alkane (C
10
to C
21
) solvents were obtained from Sigma
Chemical Company (St Louis, MO, USA). The solvents
employed in other analyses were of analytic grade. DPPH
was purchased from the Sigma Chemical Co., USA, while
quercetin was obtained from Sigma-Aldrich.
Antimicrobial analysis
The materials used for antimicrobial activity were
obtained from Mueller-Hinton Agar (Oxoid
®
/Brazil). The
microorganisms (Staphylococcus aureus (ATCC 25923),
Pseudomonas aeruginosa (ATCC 27853), Escherichia
coli (ATCC 25922) and Candida albicans (ATCC 10231)
were obtained from the American Type Culture Collection
(ATCC, Reston, VA acquired from Newprov
®
/Brazil) and
antibiotic (Nitrofurantoín, Imipenen, Tetraciclin, Fluco-
nazol ) discs were acquired from Cecon®/Brazil, namely,
nitrofurantoín (300 μg) for S. aureus, imipenen (10 μg) for
P. aeruginosa, tetraciclin (30 µg) for E.coli and ucona-
zole (50 μg) for C. albicans.
Plant Material
The leaves of the C. adamantium were colleted in the
state of Mato Grosso do Sul, Brazil, in the cities of Doura-
dos (Ddos; latitude 22º 11’ 813’ S and longitude 054º 55’
801 W) during the reproductive and vegetative stages,
Bela Vista (BV; latitude 2 06’ 35.8 S and longitude
056º 33’ 00.8’ W), Bonito (BO; latitude 21° 07’ 50.0’ S
and longitude 056° 24’ 68.0’ W) and Jardim (Jd; latitude
21° 25’ 02.0’ S and longitude 056° 13’ 77.0’ W) in 2005
during the only fruit-bearing stage. The species were iden-
tied by Marcos Sobral (UFMG) and voucher specimens
5196 (Dourados), 5198 (Bela Vista), 5197(Bonito) and
5195 (Jardim)) have been deposited in the Mato Grosso do
Sul Herbarium-HMS, Campo Grande, MS, Brazil.
Essential Oil Isolation
The oils were isolated from a 400 g quantity of fresh
Campomanesia adamantium leaves collected during the
owering, fruit-bearing and vegetative stages and were
subjected to hydrodistillation in a Clevenger-type appara-
tus for 4 hours. The oil percentages were expressed as w/w
in relation to fresh weight of the initial material.
Identification of Essential Oil Constituents
Oil samples of C. adamantium were diluted in hexa-
ne and analyzed. Retention indices were calculated accor-
ding to Zhao et al. (2005) and Isidorov et al. (1998) using
a quasi-linear equation at linear temperature programmed
GC operating conditions and a mixture of normal parafn
Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities
769
(C
8
-C
21
) as external references. The identication of oil
components was performed by comparing the spectra with
those of Nist 2.0 and Saturn Libraries as well as compa-
rison of their temperature-programmed retention indices
and mass spectra with those described by Adams (1995).
Apparatus
The GC/MS system consisted of a gas chromato-
graph (GC 3900) equipped with an ion-trap mass spec-
trometer detector (Varian Saturn 2100), using a ZB-5 (5%
of phenyl-dimethylpolysiloxane), fused-silica capillary
column (30 m x 0.25 mm i.d., 0.25 μm lm thickness),
under the following conditions: carrier gas helium; 1μL
injection volume, split at a ratio of (1:20), with initial oven
temperature of 50 º C with heating from 50 ºC to 250 ºC at
3 ºC min
-1
. The injector and ion trap detector temperatures
were 240 ºC and 200 ºC, respectively, and manifold at
70 ºC with line transfer at 240 ºC. The MS scan parameters
included an electron impact ionization voltage of 70 eV,
a mass range of 40-380 m.z
-1
and a scan interval of 0.5 s.
The antioxidant assay activity was recorded in methanol,
employing a 700 S Femto UV Spectrophotometer at a
wavelength of 517 nm.
Determination of DPPH (2,2’-diphenyl-1-
picrylhydrazyl) Radical-Scavengers of Essential
Oil Samples
The free radical scavenging activity of essential oils
and quercetin standard solutions were determined based
on their ability to react with the stable DPPH free radical.
Two milliliters of DPPH (0.004% in methanol) was added
to the essential oil solution in methanol at a concentration
of 2270 μg.mL
-1
(owering), 2320 μg.mL
-1
(vegetative)
and 2390 μg.mL
-1
(fruit-bearing). After incubation at
25
o
C for 30 minutes, the absorbance of each solution
was determined at 517 nm. The antioxidant activity (%)
of radical-scavengers was calculated as (A
o
-A
s
/A
o
) x 100,
where A
s
and A
o
are the absorbance of the sample and
control, respectively, at 517 nm.
Determination of Antimicrobial activity
The essential oils from Campomanesia adamantium
leaves, collected during the owering, fruit-bearing and
vegetative stages, were individually tested against a micro-
organism panel, including Staphylococcus aureus (ATCC
25923), Pseudomonas aeruginosa (ATCC 27853), Esche-
richia coli (ATCC 25922) and Candida albicans (ATCC
10231) in accordance with the Agar diffusion disc method
(Brasileiro et al., 2006). Briefly, the filter paper discs
Whatman No. 1 (6 mm in diameter) were impregnated
with 20 μL of the essential oil ethanolic solution at 2000
μg.mL
-1
. In vitro antimicrobial activity was determined
using eller Hinton Agar and then after Agar to solidify,
the plates were inoculated with a suspension of the tested
microorganism (0.1 mL of 1 x 10
8
UFC/mL) (turbidity
based McFarland - Probac
®
- barium sulfate standard 0.5)
and uniformly spread with a sterile swab. The discs were
then applied and plates incubated at 37 ºC for 24 hours.
The negative control assay was performed using only
organisms and not the plant extract. The positive control
used antibiotic discs (Cecon®) for each strain assay, with
the nitrofurantoín (300 μg) for Staphylococcus aureus,
imipenen (10 μg) for Pseudomonas aeruginosa, tetraciclin
(30 µg) for Escherichia coli and uconazole (50 μg) for
Candida albicans. The diameters of the inhibition zones
were measured in millimeters. All the assays were perfor-
med in triplicate.
RESULTS AND DISCUSSION
Characterization of the essential oils
Gas chromatography-mass spectrometry (GC-MS)
has been used in the separation, identication and quanti-
cation of complex mixtures, such as essential oils. As a
general rule, the identication of these compounds is not
precise, because the mass spectra of these compounds are
very similar and determination with the standard MS libra-
ry is very difcult. For this reason the retention index –IR
was used as a parameter for the GC qualitative analysis of
the complex mixtures of isomers.
The C. adamantium leaves were collected in Dou-
rados, Mato Grosso do Sul State during the reproductive
and vegetative stages of the plant and submitted to hydro-
distillation. The yields were 0.32% (owering), 0.39%
(fruit-bearing) and 0.19% (vegetative). These oil samples
were then analyzed by GC-MS using a temperature pro-
gram with a DB-5 capillary column.
A total of 95 compounds from the different stages of
C. adamantium were identied, including the presence of
terpenic hydrocarbons, ether, alcohol, aldehydes, ketones,
esters, phenols and epoxides. Alcohol and hydrocarbons
were the predominant class. Due to the complexity of the
results the components were listed in order of elution on
a DB-5 column, and their retention index and percentage
composition are described in Table I.
All the samples of essential oil predominantly de-
monstrated compounds of the cyclic series. The principal
pathway of observed cyclization from the monoterpenic
I. D. Coutinho, C. A. L. Cardoso, N. Ré-Poppi, A. M. Melo, M. C. Vieira, N. K. Honda, R. G. Coelho
770
TABLE I - Volatile compounds identied in the essential oil of Campomanesia adamantium leaves at different phenological stages
Compounds
a
RI
b
RI
c
Flowering Fruit bearing Vegetative
Relative area (%)
α-thujene 925 926 0.61 tr -
α-pinene 939 934 13.23 7.45 0.07
α-fenchene 944 951 0.50 - 0.02
β-pinene 976 977 8.99 6.69 0.06
myrcene 990 991 0.88 0.21 -
mesitylene 993 994 tr - -
α-phellandrene 1004 1005 0.32 - -
δ-3-carene 1010 1011 0.19 - -
α-terpinene 1016 1018 0.24 - -
o-cymene
1024 1022 1.49 0.15 0.09
limonene 1031 1031 22.24 0.99 0.66
1,8-cineole 1030 1033 0.87 0.44 -
(Z)-β-ocimene 1037 1040 0.03 - -
(E)-β-ocimene 1047 1050 0.28 - -
γ-terpinene 1058 1062 0.83 0.14 0.03
terpinolene 1087 1088 - 0.41 -
p-mentha-2,4(8)-diene
1088 1086 1.75 - 0.10
linalool 1100 1098 - 4.97 0.53
α-fenchol 1113 1112 0.34 tr 0.27
cis-p-menth-2-en-1-ol
1121 1121 0.06 - 0.09
α-camphonelal 1125 1125 tr - 0.11
cis-limonene oxide
1132 1134 tr - -
trans-sabinol
1138 1140 0.06 - 0.03
camphor 1143 1143 - - 0.02
camphene hydrate 1146 1148 0.11 - 0.02
isoborneol 1155 1156 0.01 - 0.01
borneol 1164 1165 0.45 0.24 0.37
3-thujy’alcohol 1167 1166 tr - -
terpin-4-ol 1176 1177 0.57 0.26 0.04
p-cymen-8-ol
1184 1183 0.09 - -
(Z)-3-hexenyl butyrate 1186 1186 0.01 - -
α-terpineol 1190 1189 1.40 0.58 0.37
myrtenol 1195 1194 0.07 - 0.04
trans-piperitol
1206 1205 tr - -
trans-carveol
1217 1217 0.03 - 0.03
nerol 1227 1228 0.02 - -
cis-carveol
1229 1229 0.01 - -
cumin aldehyde 1238 1339 tr - -
carvone 1242 1242 0.01 - -
geraniol 1254 1255 0.01 - 0.02
perilla aldehyde 1272 1271 0.09 - -
α-terpinen-7-al 1282 1282 0.02 - -
p-cymen-7-ol
1286 1287 - - 0.01
trans-sabinyl acetate
1290 1291 tr - -
carvacrol 1300 1298 - - 0.02
neo-dihydro carveol acetate
1303 1303 tr - -
methyl geranate 1323 1323 0.02 - -
δ-elemene 1337 1339 0.26 0.29 0.63
α-cubebene 1349 1351 0.04 - 0.06
cyclosativene 1371 1368 0.07 - 0.14
α-ylangene 1372 1372 0.05 0.17 0.10
α-copaene 1375 1376 0.37 - 1.40
isoledene 1376 1373 - 1.57 -
Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities
771
Compounds
a
RI
b
RI
c
Flowering Fruit bearing Vegetative
Relative area (%)
β-elemene 1391 1391 0.60 0.50 1.21
α-gurjunene 1409 1409 0.15 0.26 0.24
β-caryophyllene 1419 1418 3.23 8.97 6.12
β-gurjunene 1428 1432 0.21 0.36 0.35
aromadendrene 1438 1439 0.79 1.38 2.48
α-humullene 1453 1454 1.12 4.67 2.60
seychellene 1460 1460 0.43 1.01 -
cis-muurola-4(14)-5-diene
1462 1460 0.05 - 1.28
drima-7,9(11)-diene 1469 1469 tr - -
γ-gurjunene 1472 1473 - - 0.09
γ-muurolene 1476 1477 0.68 1.00 1.15
germacrene D 1481 1480 2.66 11.82 5.87
β-selinene 1485 1485 0.34 0.22 0.47
cis-β-guaiene
1491 1490 0.21 - 0.23
bicyclogermacrene 1496 1494 4.48 18.95 16.17
trans-β-guaiene
1500 1500 - - 0.52
α-bulnesene 1504 1505 0.14 - 0.18
germacrene A 1505 1503 - 0.42 -
γ-cadinene 1513 1513 0.47 0.60 0.97
δ-cadinene 1523 1524 1.67 3.63 2.82
cadina-1,4-diene 1532 1532 0.04 - 0.08
α-cadinene 1537 1538 0.13 - 0.18
selina-3,7(11)-diene 1541 1542 0.06 - -
α-calacorene 1542 1542 0.04 - -
germacrene B 1556 1556 0.36 0.27 0.30
epi-longipinanol
1559 1561 - 0.42 -
(E)-nerolidol 1564 1564 1.07 - 0.15
ledol 1566 1565 - 1.06 -
spathulenol 1577 1576 2.08 1.62 7.34
globulol 1584 1583 3.91 4.64 11.05
viridiorol 1591 1590 - 2.54 -
guaiol 1593 1595 0.19 1.10 -
humulene epoxide II 1608 1606 0.24 tr 1.64
epi-1,10-di-cubenol
1614 1614 0.26 tr 0.29
epi-1-cubenol
1627 1627 0.64 - 1.33
γ-eudesmol 1631 1630 0.40 0.21 0.86
epi-α-cadinol
1640 1640 1.00 1.99 1.17
α-muurolol 1645 1645 0.50 0.56 0.85
a-cadinol
1654 1653 2.63 2.18 2.98
cadalene 1675 1674 - - 0.19
juniper camphor 1693 1691 0.07 - -
a
Constituents listed in order of elution in DB-5 column.
b
RI= Retention index calculation using a temperature program according
to n-alkanes.
c
RI= Retention index described by Adams17. tr = traces (%< 0.01)
TABLE I - Volatile compounds identied in the essential oil of Campomanesia adamantium leaves at different phenological stages (cont.)
compounds were mentane and pinane, best represented by
limonene and α-pinene. The principal pathway cyclization
from the sesquiterpenic compounds was germacrane,
represented by the main compounds bicyclogermacrene,
germacrene D and globulol.
A total of 82 compounds were identified in the
essential oil from the owering stage, where there were
48.78% of both monoterpenes and sesquiterpenes. The
main compounds identified in this essential oil were
limonene (22.24%), α-pinene (13.23%) and β-pinene
(8.99%). During the fruit-bearing stage there were 44
compounds identied , consisting of 31.82% monoter-
penes and 68.19% sesquiterpenes, the main compounds
of which were bicyclogermacrene (18.95%), germacrene
I. D. Coutinho, C. A. L. Cardoso, N. Ré-Poppi, A. M. Melo, M. C. Vieira, N. K. Honda, R. G. Coelho
772
D (11.82%), β-caryophyllene (8.97%), α-pinene (7.45%)
and β-pinene (6.69%). In the essential oil composition
collected from the vegetative stage of the same plant, 60
compounds were identified. This consisted of 38.33%
monoterpenes and 61.67% sesquiterpenes, with the main
compounds being bicyclogermacrene (16.17%), globulol
(11.05%), β-caryophyllene (6.12%) and germacrene D
(5.87%).
The chemical composition of the essential oils from
different reproductive and vegetative stages was similar in
relation to major components, however the composition
percentage of these was very different. This is because the
samples from the vegetative stage showed a higher amount
of sesquiterpenes (relative area), while the owering stage
samples showed the opposite, in which the major com-
pounds were monoterpenes.
Studies reporting on C. xanthocarpa (Limberger et
al., 2004) and C. phaea (Adati, Ferro, 2006) leaves, both
collected in the vegetative stage, showed predominance
in the sesquiterpenes, while in the C. lineatifolia (Osorio
et al., 2006) leaves studied during the fruit-bearing stage
the major compounds were 1,8-cineol, α-pinene and β-
caryophyllene.
The production and types of the terpenes can be
linked to external factors, such as differences in light,
temperature and water levels (Lima et al., 2003). During
the owering stage, the plant was exposed to rain and high
temperatures in the spring, while during the vegetative sta-
ge the plant was exposed to dryness and low temperatures
in the fall. At the fruit-bearing stages the relative area is
very well divided between monoterpenes and sesquiter-
penes, with high temperatures and less rain during the
summer. The chemical variability can also be related to an
adaptation of pollination from different species of insects,
due to the reproductive strategy of the plant (Stefanello
et al., 2006).
In addition to the aforementioned factors contri-
buting to differences in the chemical composition of the
essential oils, the differing altitudes and soil types between
our sample collection areas may also be a factor. Due to
these factors, the C. adamantium leaves were collected
in the cities of Dourados, Bonito, Jardim and Bela Vista
during the fruit-bearing stage and were submitted to hydro-
distillation where the essential oils yielded 0.39; 0.20; 0.10
and 0.13%, respectively.
Table 2 shows the difference in the chemical com-
position of the samples collected from different regions,
while Figure 1 shows the variation in relative areas of
the major compounds identified in the four cities. The
samples from Dourados and Jardim are characterized
by sesquiterpene bicyclogermacrene, germacrene D and
β- caryophyllene amounts, while the samples from Bela
Vista and Bonito are similar, mainly in the monoterpene
amounts of α-pinene, β-pinene, limonene and linalool.
TABLE II - Compounds identied in the essential oil of Campomanesia adamantium leaves in different localities of Mato Grosso
do Sul State, Brazil, during the fruit-bearing stage
Compounds
a
IR
lit
b
IR
cal
c
BV BO Jd Ddos
Relative area (%)
α-thujene 931 925 - Tr - tr
α-pinene 939 931 11.29 12.58 5.02 7.45
α-fenchene 951 946 Tr 0.44 - -
n-heptanol
969 965 - 0.04 - -
pentyl propanoate
972 968 - tr - -
β-pinene 976 975 5.54 9.81 3.36 6.69
myrcene 991 990 0.56 0.88 Tr -
α-phellandrene 1005 1004 Tr 0.45 0.93 -
δ-3-carene 1011 1010 tr 0.22 - -
α-terpinene 1018 1016 0.25 0.39 - -
o-cymene
1022 1023 0.41 0.97 5.45 0.15
limonene 1031 1027 11.06 24.00 Tr 0.99
1.8-cineole 1033 1031 3.65 1.41 - 0.44
(Z)-β-ocimene 1040 1037 - tr 0.55 -
(E)-β-ocimene 1050 1047 0.31 0.32 0.81 -
γ-terpinene 1062 1058 0.61 1.25 - 0.14
terpinolene 1088 1088 0.91 2.49 0.94 0.41
linalool 1098 1100 7.40 3.60 4.97
α-fenchol 1112 1113 0.30 0.19 - tr
borneol 1165 1164 0.53 0.39 - 0.24
terpin-4-ol 1177 1176 - 0.53 - 0.26
Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities
773
Compounds
a
IR
lit
b
IR
cal
c
BV BO Jd Ddos
Relative area (%)
α-terpineol 1189 1189 2.38 0.17 - 0.58
Myrtenol 1194 1195 - tr - -
(E)-2-decenal 1261 1261 - tr - -
perilla aldehyde 1271 1273 - tr - -
perillol 1295 1297 1.24 tr - -
δ-elemene 1339 1337 0.31 0.37 Tr 0.29
α-cubebene 1351 1350 - tr - -
α-ilangene 1372 1372 - - - 0.17
α-copaene 1376 1376 0.20 0.27 1.42 1.57
β-elemene 1391 1392 0.81 0.27 0.93 0.50
α-gurjunene 1409 1409 0.41 tr - 0.26
β-caryophyllene 1418 1419 3.12 3.15 8.14 8.97
β-gurjunene 1432 1429 - 0.13 Tr 0.36
aromadendrene 1439 1439 1.32 0.54 0.50 1.38
Z-β-farnesene 1443 - 0.04 - -
α- caryophyllene 1454 1453 1.01 0.93 2.07 4.67
Seichellene 1460 1460 0.55 0.30 0.70 1.01
γ-muurolene 1477 1477 0.76 0.57 1.64 1.00
germacreno D 1480 1481 4.86 2.97 10.65 11.82
β-selinene 1485 1486 - 0.17 0.77 0.22
valencene 1491 1491 - 0.24 0.81 -
biciclogermacrene 1494 1496 9.13 5.97 20.05 18.95
α-bulnesene 1505 1505 0.31 - - -
germacrene A 1503 1505 - 0.15 - 0.42
γ-cadinene 1513 1514 0.49 0.39 0.82 0.60
δ-cadinene 1524 1524 1.25 1.25 4.18 3.63
cadina-1,4-diene 1532 1532 - tr - -
α-cadinene 1538 1538 - tr - -
selina-3,7(11)-diene 1542 1542 - tr - -
elemol 1549 1552 - tr - -
germacrene B 1556 1557 - 0.16 0.64 0.27
epi-longipinanol
1561 1560 - 0.12 - 0.42
(E)-nerolidol 1564 1564 5.50 0.82 Tr -
ledol 1565 1565 - 0.13 1.93 1.06
spathulenol 1576 1576 2.64 1.15 1.15 1.62
globulol 1583 1583 6.46 3.63 5.82 4.64
viridiorol 1590 1590 1.85 1.16 2.38 2.54
cis-β-elemonene
1594 1593 - - 1.18
guaiol 1595 1595 - 0.70 - 1.10
humullene epoxide II 1606 1609 0.33 0.19 Tr tr
epi-1,10-di-cubenol
1614 1615 - 0.18 Tr tr
epi-10-δ-eudesmol
1619 1619 - 0.23 Tr -
epi-1-cubenol
1627 1627 0.44 0.56 0.40 -
γ-eudesmol 1630 1630 - tr 0.25 0.21
epi-α-cadinol
1641 1641 1.70 1.92 - 1.99
α-muurolol 1645 1646 0.36 0.23 3.00 0.56
α-cadinol 1653 1654 1.89 2.35 0.84 2.18
a
Constituents listed in order of elution in DB-5 column.
b
RI= Retention index calculation using a temperature program according
to n-alkanes.
c
RI= Retention index described by Adams17. tr = traces (%< 0.01).
TABLE II - Compounds identied in the essential oil of Campomanesia adamantium leaves in different localities of Mato Grosso
do Sul State, Brazil, during the fruit-bearing stage (cont.)
From these results it can be concluded that the chemi-
cal composition of the essential oil from the leaves of the C.
adamantium is inuenced during different stages (including
the fruit-bearing stage) as well as by different regions.
I. D. Coutinho, C. A. L. Cardoso, N. Ré-Poppi, A. M. Melo, M. C. Vieira, N. K. Honda, R. G. Coelho
774
Determination of DPPH Radical-Scavengers
The essential oils were screened for antioxidant ac-
tivity. The use of 1,1-diphenyl-2-picryl-hydrazyl (DPPH)
as a reagent for screening the antioxidant activity of small
molecules has been reported (Tepe et al., 2005).
The inhibition percentage of the radical-scavengers
activity in the essential oil was 9.91% (2270 μg.mL
-1
) at the
owering stage, 7.47% (2390 μg.mL
-1
) at the fruit-bearing
stage, and 6.89% (2320 μg.mL
-1
) at the vegetative stage.
The reference compound quercetin showed a scavenging
effect of 90% (20 μg.mL
-1
), 91% (40 μg.mL
-1
), 93% (80
μg.mL
-1
), 94% (160 μg.mL
-1
) and 97% (320 μg.mL
-1
).
In this test, the scavenging of the DPPH radical is
followed by monitoring of the decrease in absorbance at
517 nm, which occurs due to the antioxidant reduction, and
has been used to assess the ability of phenolic compounds
to transfer labile H atoms to radicals (Djeridane et al.,
2006). The lower antioxidant activity has been attributed
to the absence and/or lower amount of the donor groups of
the electron in ortho position in relation to phenolic hydro-
xyl, and the presence of larger amounts of hydrocarbons
terpenes. This result is in agreement with other studies of
essential oils with similar patterns (Sacchetti et al., 2005).
Assay of antimicrobial activity
Results from the assessment of antimicrobial activity
using the Agar diffusion disc method are summarized in
Table 3. The essential oil at all stages exhibited moderate
to high activity against the tested microorganism. The es-
sential oil in the owering and fruit-bearing stages exhibi-
ted an even better effect than that provided by the reference
antibiotics against Staphylococcus aureus and Candida
albicans, and moderate effect in relation to Pseudomonas
aeruginosa and Escherichia coli. Meanwhile, the samples
TABLE III - Antimicrobial activity of the essential oil from Campomanesia adamantium leaves
Microorganism EOFl* EOFr* EOV* Antibiotics
Staphylococcus aureus
20.00±0.40 20.00±0.60 16.00±0.20 22.00±0,60
a
Pseudomonas aeruginosa
10.00±0,20 10.00±0,00 6.00±0,00 17.40±0.60
b
Escherichia coli
2.00±0,00 2.00±0,00 2.00 ±0,00 4.00±0.00
c
Candida albicans
26.00±0,60 26.00±0,40 16.00±0.20 22.00±0.40
d
*EOFl: essential oil owering stage; EOFr: essential oil fruit-bearing stage; EOV: essential oil vegetative stage. All analyses used
40 µg of the essential oil samples.
a
nitrofurantoin (300 µg);
b
Impenen (10 µg);
c
tetracicilin (30 µg);
d
uconazole (50 µg).
FIGURE 1 - Major compounds identied in the Campomanesia adamantium leaves collected in different localities of Mato Grosso
of the Sul State, Brazil during the fruit-bearing stage.
Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities
775
of essential oil during the vegetative stage showed very
weak activity against all tested microorganisms.
The different antimicrobial activity offered by
essential oils, can be linked to their different chemical
compositions, therefore the essential oils isolated from the
owering and fruit-bearing stages have larger amounts of
monoterpene hydrocarbons with allylic groups and ether,
alcohol, aldehydes, ketones, esters and phenols than the
essential oil isolated from the vegetative stage. The biolo-
gical activity of the terpenes can be seen in relation to the
chemical structure, functional groups and stereochemistry
of identied compounds (Henriques et al., 2006).
ACKNOWLEDGEMENT
The authors thank FUNDECT, CNPq and CAPES
for nancial support and grants, respectively, and Dr. Mar-
cos Sobral for identifying the botanical material.
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Received for publication on 02
nd
October 2008.
Accepted for publication on 25
th
June 2009.
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