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ORIGINAL ARTICLE
Chemical composition and antifungal properties of
the essential oil and various extracts of Mikania
scandens (L.) Willd
Shah Alam Siddiqui
a
, Rafiquel Islam
a
, Rezuanul Islam
b
, A.H.M. Jamal
b
,
Tanzima Parvin
a
, Atiqur Rahman
a,
*
a
Department of Applied Chemistry and Chemical Technology, Islamic University, Kushtia 7003, Bangladesh
b
Department of Biotechnology and Genetic Engineering, Islamic University, Kushtia 7003, Bangladesh
Received 28 April 2012; accepted 25 July 2013
KEYWORDS
Mikania scandens (L.);
Essential oil;
GC–MS;
Different extracts;
MIC;
Antifungal activity
Abstract This study was undertaken to assess the antifungal potential of the essential oil and var-
ious extracts of Mikania scandens (L.) Willd. The hydrodistilled leaf essential oil of M. scandens was
analysed by GC–MS. Twenty-four compounds representing 97.45% of the total leaves oil were
identified, of which b-caryophyllene (16.98%), d-cadinene (12.22%), a-cubebene (11.33%), 1,2-ben-
zenedicarboxylic acid (10.17%), caryophyllene oxide (7.74%), b-himachalene (4.68%), T-cadinol
(3.98%), tetratetracontane (3.83%), 1H-cyclopropa[a]naphthalene (3.56%), b-farnesene (3.08%)
etc. were the major compounds. The essential oil and extracts (chloroform, ethyl acetate and meth-
anol) of M. scandens were tested for antifungal activity, which was determined by disc diffusion and
minimum inhibitory concentration (MIC) determination methods. The essential oil and various
extracts displayed a great potential of antifungal activity as a mycelial growth inhibition against
the tested phytopathogenic fungi such as Rhizoctonia solani AG-1 (IB) KACC 40111, R. solani
AG-2-2 (IV) KACC 40132, Pythium graminicola KACC 40155, Tricoderma harzianum KACC
40791 and Fusarium oxysporum KACC 40052, in the range of 40.0–75.4% and the minimum inhib-
itory concentration ranging from 125 to 500 lg/ml. The present results demonstrated that M. scan-
dens mediated oil and extracts could be potential sources of natural fungicides to protect crops from
fungal diseases.
ª2013 Production and hosting by Elsevier B.V. on behalf of King Saud University.
1. Introduction
Mikania scandens (L.), a medicinal plant is popularly used as a
herbal remedy for various ailments in Bangladesh. The genus
Mikania is a member of the family Asteraceae (Compositae).
Within that family, Mikania is a member of the tribe Eupator-
ieae of the subfamily Asteroideae. Some species of Mikania are
*Corresponding author. Tel.: +88-071-74910-20x2252/2266; fax:
+88-071-74905.
E-mail addresses: marahman12@yahoo.com,atiq@acct.iu.ac.bd
(A. Rahman).
Peer review under responsibility of King Saud University.
Production and hosting by Elsevier
Arabian Journal of Chemistry (2013) xxx, xxx–xxx
King Saud University
Arabian Journal of Chemistry
www.ksu.edu.sa
www.sciencedirect.com
1878-5352 ª2013 Production and hosting by Elsevier B.V. on behalf of King Saud University.
http://dx.doi.org/10.1016/j.arabjc.2013.07.050
Please cite this article in press as: Siddiqui, S.A. et al., Chemical composition and antifungal properties of the essential oil and various
extracts of Mikania scandens (L.) Willd. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.07.050
M. scandens,Mikania cordifolia (L. f.) Willd, Mikania cordata
(Burm. f.) B. L. Robins. In Bangladesh, M. scandens is known
as ‘‘Jarmany lota’’ (Moon et al., 1993). Besides, this vining spe-
cies can be found in the southeast corner of Missouri. The
plant is very easy to identify in the field because of its vining
habit, opposite, sagittate leaves, and umbels of whitish flower
heads. This is a weedy species which can grow very long very
quickly. It is probably not the best choice to plant around a
water garden. The plant is, however, frequently visited by
many different types of flying insects. The genus Mikania is
a large cosmopolitan genus confined mostly to the tropics.
Fungi have long been recognized as causal agents of plant
diseases such as root rot symptom (Rhizoctonia solani), pyth-
ium root rot (Pythium Graminicola), soil green mould (Trico-
derma harzianum), and vascular wilt (Fusarium oxysporum)
(Hakuno et al., 2002;Waterhouse and Waterston, 1964;
Harman et al., 2004; Agrios, 1988). Chemical fungicides are
made up of many different volatile compounds and have been
shown to possess fungicidal properties (Ahmet et al., 2005).
Essential oils and plant extracts are gaining increasing interest
because of their relatively safe status, their wide acceptance by
consumers and their exploitation for potential multi-purpose
functional uses. So, essential oils and plant extracts are one
of the most promising groups of natural compounds for the
development of safer anti-fungal agents. M. scandens leaf is
used as its analgesic and antioxidant properties (Hasan et al.,
2009). However, there is no report available in the literature
on the detailed analyses of the essential oil of M. scandens
and its antifungal property. Therefore, we undertook investi-
gations of the chemical composition of the essential oil by
GC–MS and the antifungal properties of the essential oil and
extracts from M. scandens occurring in Bangladesh and the
results are reported in this communication.
2. Materials and methods
2.1. Plant materials
The leaves of M. scandens (L.) were collected from the local
area of Muksudpur, Gopalganj, Bangladesh, in June and July
2010. The taxonomic identification of the plant was confirmed
by Dr. Oliur Rahman, Professor, Department of Botany, Uni-
versity of Dhaka, and a voucher specimen (DACB 37894) has
been deposited at the Bangladesh National Herbarium.
2.2. Isolation of the essential oils
The air-dried leaves (250 g) of M. scandens were subjected to
hydro distillation for 3 h using a Clevenger type apparatus.
The oil was dried over anhydrous sodium sulphate and pre-
served in a sealed vial at 4 C until further analysis.
2.3. Preparation of organic extracts
The air-dried leaves M. scandens were first pulverized into a
powdered form. The dried powder (50 g) was then extracted
with chloroform, ethyl acetate and methanol separately at
room temperature for 7 days and the solvents were evaporated
by a vacuum rotary evaporator at a temperature of 50 C. The
extraction process yielded chloroform (6.2 g), ethyl acetate
(7.4 g) and methanol (6.5 g) extracts, respectively. Solvents
(analytical grade) for extraction were obtained from commer-
cial sources (Sigma–Aldrich, St. Louis, MO, USA).
2.4. GC–MS/MS analysis
The GC–MS was carried out using a total ion monitoring
mode on Varian 3800 gas chromatograph interfaced to a Var-
ian Saturn ion trap 2200 GC–MS spectrometer. The tempera-
tures of transfer line and ion source were 280 and 275 C,
respectively. Ions were obtained by the electron ionization
mode. The ZB-1 capillary column (30 m length, 0.25 mm
I.D. and 0.25 lm film thickness) was used. A 20% split injec-
tion mode was selected with a solvent delay time of 3 min with
an injection volume of 0.2 ll. The initial column temperature
was started at 50 C for 1 min, programmed at 8 C/min–
200 C and heated until 280 Cat10C/min. The injection
port was set at 250 C. Helium was used as the carrier gas at
a constant flow rate of 1.0 ml/min. Molecular ions (mass
range: 40–500 m/z) were monitored for identification. The rel-
ative percentage of the oil constituents was expressed as per-
centage by peak area normalization. The identification of
components of the essential oil was based on their retention
indices, relative to a homologous series of n-alkane (C
8
–C
20
)
on the ZB-1 capillary column under the same operating condi-
tions and computer matching with the GC–MS spectra from
the Wiley 6.0 MS data and literature data (Adams, 2007).
2.5. Microorganisms
The plant pathogenic fungi used in the experiment were
R. solani AG-1 (IB) KACC 40111, R. solani AG-2-2 (IV)
KACC 40132, P. graminicola KACC 40155, T. harzianum
KACC 40791 and F. oxysporum KACC 40052. The fungal
pathogens were kindly provided by Prof. Yong Se Lee,
Department of Bioresource Technology, College of Agricul-
ture and Environmental Science, Daegu University, Korea.
Cultures of each fungal species were maintained on potato-
dextrose agar (PDA) slants and stored at 4 C.
2.6. Preparation of spore suspension and test samples
The spore suspension of R. solani AG-1, R. solani AG-2-2,
P. graminicola,T. harzianum and F. oxysporum was obtained
from their respective 5–10 day old cultures, mixed with sterile
distilled water to obtain a homogenous spore suspension of
10
5
spore/ml. Essential oil, chloroform, ethyl acetate and
methanol extract of M. scandens were dissolved in methanol
separately to prepare the stock solution with their respective
known weights, which were further diluted to prepare test
samples.
2.6.1. Determination of antifungal activity of essential oil and
crude extracts
Petri dishes (9 cm diameter) containing 20 ml of PDA medium
were used for antifungal activity assay, performed in solid
media by the disc diffusion method (Duru et al., 2003). Sterile
Whatman paper discs of 6 mm diameter were pierced in the
agar plates, equidistant and near the border, where the essen-
tial oil 10 ll (1000 lg/disc) and all extract samples 15 ll
2 S.A. Siddiqui et al.
Please cite this article in press as: Siddiqui, S.A. et al., Chemical composition and antifungal properties of the essential oil and various
extracts of Mikania scandens (L.) Willd. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.07.050
(1500 lg/disc) were used separately. A disc of fungal inocu-
lums 6 mm in diameter was removed from pre-grown cultures
of all the fungal strains tested and placed upside down in the
centre of the Petri dishes. The plates were incubated at
28 ± 2 C for 7 days, until the growth in control slates reached
the edges of the plates. Growth inhibition of each of the fungal
strains was calculated as the percentage of inhibition of radial
growth relative to the control along with antifungal effect on
fungal mycelium. The plates were used in triplicates for each
treatment. Growth inhibition of treatment against control
was calculated by percentage, using the following formula:
Inhibition ratio (%) = {1mycelium growth of treatment
(mm)/mycelium growth of control (mm)} ·100
2.6.2. Minimum inhibitory concentration (MIC)
The minimum inhibitory concentration of essential oil and
crude extract was determined by the twofold dilution method
(Murray et al., 1995). Samples were dissolved in methanol
according to their respective known weights. The solutions
were serially diluted with methanol and were added to PDB
to final concentrations of 125, 250, 500, and 1000 lg/ml,
respectively. A 10 ll spore suspension of each test strain was
inoculated in the test tubes in PDB medium and incubated
for 5–7 days at 28 ± 2 C. The control tubes containing
PDB medium were inoculated only with fungal suspension.
The minimum concentration at which no visible growth was
observed was defined as the MIC, which was expressed in
lg/ml.
2.7. Statistical analysis
The essential oil and different organic extracts were assayed
for antifungal activity. Each experiment was run in triplicate,
and mean values were calculated. The statistical analysis was
carried out employing a one way ANOVA (p< 0.05). A statis-
tical package (SPSS version 11.0) was used for the data
analysis.
3. Results
3.1. Chemical composition of essential oil
GC–MS analyses of the oil of M. scandens (L.) led to the iden-
tification of twenty-four different compounds, representing
97.45% of the total leaf oil. The identified compounds are
listed in Table 1 according to their elution order on a ZB-1
capillary column. The oil contains a complex mixture consist-
ing of mainly oxygenated monoterpene and sesquiterpene
hydrocarbons. The major compounds detected in the essential
oil were b-caryophyllene (16.98%), d-cadinene (12.22%),
a-cubebene (11.33%), 1,2-benzenedicarboxylic acid (10.17%),
caryophyllene oxide (7.74%), b-himachalene (4.68%), T-cadi-
nol (3.98%), tetratetracontane (3.83%), 1H-cycloprop-
a[a]naphthalene (3.56%) and b-farnesene (3.08%).
3.2. Antifungal activity of essential oil and crude extracts
The oil of M. scandens exhibited a moderate to high antifungal
activity against all the tested fungi except R. solani (AG-1). A
low inhibition effect was observed against R. solani (AG1-1).
At the concentration of 10 ll (1000 lg/ml), the essential oil
showed a potent inhibitory effect on the growth of R. solani
(AG1-1 (62.8–63.4%), R. solani (AG-2-2) (53.2–54.6%),
P. graminicola (70.3–71.3%), T. harzianum (54.8–56.0%) and
F. oxysporum (74.9–75.9%) as shown in Table 2. Also, the
crude chloroform, ethyl acetate and methanol extract
(1500 lg/ml) showed mycelium growth inhibition against some
of the phyto-pathogens but not for all. According to the results
reported in Table 2, the ethyl acetate extract showed a lower
antifungal effect than essential oil against R. solani (AG-1)
(53.1–54.7%), P. graminicola (56.4–57.4%) and F. oxysporum
(53.2–54.6%). The crude methanol, chloroform and ethyl
acetate extract did not show any inhibitory effect against
R. solani (AG-2-2). Besides, the chloroform extract showed
moderate antifungal activity against some of the fungi tested.
Also, the chloroform extract showed relatively better anti-
fungal effect against F. oxysporum (54.7–56.1%) as compared
to ethyl acetate extract.
3.3. Minimum inhibitory concentration
According to the results given in Table 3, MIC of essential oil
was found more effective against P. graminicola and F. oxyspo-
rum (125 lg/ml) as compared to those of R. solani (AG-1) and
T. harzianum (250 lg/ml). The ethyl acetate extract displayed
potent antifungal activity against F. oxysporum,P. graminicola
and R. solani AG-1 with MIC values of 250–500 lg/ml,
whereas the F. oxysporum and P. graminicola were 250 lg/
ml. Besides, the MIC values of chloroform and methanol ex-
tract against F. oxysporum,P. graminicola and R. solani AG-
1 were found within the range of 250–500 lg/ml.
4. Discussion
The increasing social and economic implications caused by
fungi means there is a constant striving to produce safer food
crops and to develop new antifungal agents. In general,
plant-derived essential oil is considered as non-phytotoxic
compounds and potentially effective against plant pathogenic
fungi. In recent years, interests have been generated in the
development of safer antifungal agents such as plant-based
essential oils and extracts to control phytopathogens in agri-
culture (Costa et al., 2000). Several publications have docu-
mented the antifungal activities of essential oil and plant
extracts (Rahman et al., 2010, 2011). Thus essential oil is a
promising natural antifungal agent with potential applications
in agro-industries to control plant pathogenic fungi causing
severe destruction in crops. The hydro distillation of the
M. scandens (L.) gave dark yellowish oil with the major com-
ponents having oxygenated monoterpenes and sesquiterpenes,
and their respective hydrocarbons. In recent years, several
researchers have reported that monoterpene and sesquiterpene
hydrocarbons and their oxygenated derivatives are the major
components of essential oil of plant origin, which have enor-
mous potential to strongly inhibit microbial pathogens (Cakir
et al., 2004). The essential oil of M. scandens showed a remark-
able antifungal effect against all the fungi which could be
attributed to the presence of phenolic compounds and oxygen-
ated monoterpenes and sesquiterpene hydrocarbons (Guillen
and Manzanos, 1998). In our opinion, major components of
M. scandens essential oil such as b-caryophyllene (16.98%),
d-cadinene (12.22%), a-cubebene (11.33%), 1,2-benzenedi-
Chemical composition and antifungal properties of the essential oil and various extracts of Mikania 3
Please cite this article in press as: Siddiqui, S.A. et al., Chemical composition and antifungal properties of the essential oil and various
extracts of Mikania scandens (L.) Willd. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.07.050
Table 3 Minimum inhibition concentration of the essential oil and various leaf extracts of Mikania scandens (L.).
Fungal strains Minimum inhibition concentration (MIC)
a
Essential oil
b
Leaf extracts
c
CHCl
3
MeOH EtOAc
Rhizoctonia solani AG-1 (IB) KACC 40111 250 500 500 500
Rhizoctonia solani AG-2-2 (IV) KACC 40132 nd nd nd nd
Pythium graminicola KACC 40155 125 500 250 250
Tricoderma harzianum KACC 40791 250 nd nd nd
Fusarium oxysporum KACC 40052 125 250 500 250
nd: not detected.
a
Minimum inhibitory concentration (MIC).
b
MIC of essential oil (values in lg/ml).
c
MIC of various leaf extracts of CHCl
3
(chloroform), MeOH (methanol), EtOAc (ethyl acetate) (values in lg/ml).
Table 1 Chemical composition of the essential oil of the leaves of Mikania scandens (L.).
Sl. No. Compound RI
a
%RA
b
Identification
c
1. O-Decylhydroxylamine 1100 1.95 RI, MS
2. Myrtenol 1201 1.40 RI, MS
3. Dodecamethyl cyclohexasiloxane 1321 tr RI, MS
4. a-Cubebene 1351 11.33 RI, MS
5. Naphthalene, 1,2,3,4-tetrahydro-1,6-dime 1353 tr RI, MS
6. a-Copaene 1379 1.82 RI, MS
7. b-Caryophyllene 1414 16.98 RI, MS
8. 1H-cyclopropa[a]naphthalene 1417 3.56 RI, MS
9. cis-b-Farnesene 1448 0.70 RI, MS
10. c-Muurolene 1460 1.24 RI, MS
11. d-Cadinene 1524 12.22 RI, MS
12. Caryophyllene oxide 1578 7.74 RI, MS
13. 2-Pentadecanone, 6,10,14-trimethyl 1601 1.04 RI, MS
14. 1,2-Benzenedicarboxylic acid 1603 10.17 RI, MS
15. Humulene epoxide-II 1607 1.67 RI, MS
16. b-himachalene 1614 4.68 RI, MS
17. T-Cadinol 1634 3.98 RI, MS
18. T-Muurolol 1641 2.47 RI, MS
19. b-Farnesene 1672 3.08 RI, MS
20. Tonalide 1850 1.34 RI, MS
21. Nonadecane 1900 2.64 RI, MS
22. Phthalic acid, butyl hexyl ester 1970 1.19 RI, MS
23. (-)-Spathulenol 2464 1.92 RI, MS
24. Tetratetracontane 4395 3.83 RI, MS
Total identified 97.45%
a
Retention index relative to n-alkanes on ZB-1 capillary column, tr: trace amount (<0.30%).
b
Relative area (peak area relative to the total peak area).
c
Identification: MS, comparison of mass spectra with MS libraries; RI, comparison of retention index with bibliography.
Table 2 Antifungal activity of the leaves essential oil and various extracts of Mikania scandens (L.).
Fungal strains Radial growth inhibition
Essential oil CHCl
3
MeOH EtOAc
Percent
a
Percent
a
Percent
a
Percent
a
Rhizoctonia solani AG-1 (IB) KACC 40111 63.1 ± 0.7
b
40.0 ± 0.6
b
nd 53.9 ± 0.8
b
Rhizoctonia solani AG-2-2 (IV) KACC 40132 53.9 ± 0.7
b
nd nd nd
Pythium graminicola KACC 40155 70.8 ± 0.5
b
52.3 ± 0.6
b
nd 56.9 ± 0.5
b
Tricoderma harzianum KACC 40791 55.4 ± 0.6
b
nd nd nd
Fusarium oxysporum KACC 40052 75.4 ± 0.5
b
55.4 ± 0.7
b
nd 53.9 ± 0.7
b
nd: not detected of antifungal activity. Solvents (Chloroform, Methanol, and Ethyl acetate).
a
Percentage of radial growth inhibition.
b
Values are given as mean ± S.D. (n= 3), and considered to be significantly different at P< 0.05.
4 S.A. Siddiqui et al.
Please cite this article in press as: Siddiqui, S.A. et al., Chemical composition and antifungal properties of the essential oil and various
extracts of Mikania scandens (L.) Willd. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.07.050
carboxylic acid (10.17%) and caryophyllene oxide (7.74%)
have the key roles for their antifungal activities (Cheng
et al., 2004; Gazim et al., 2008; Tolouee et al., 2010; Ogunlesi
et al., 2009; Abi-Ayad et al., 2011). Also, the components such
as b-himachalene (4.68%), T-cadinol (3.98%), tetratetracon-
tane (3.83%), 1H-cyclopropa[a]naphthalene (3.56%) and
b-farnesene (3.08%) contributed to the antifungal activity of
the oil (Daoubi et al., 2005; Cheng et al., 2006; EL Mehalawy,
2004; Guo et al., 2008).
5. Conclusion
Therefore, it would also be interesting to study the effects of
essential oil and different extracts of M. scandens (L.) against
other important fungi for developing new antifungal agents
to control serious fungal diseases in plant, animal and human
beings. Thus, M. scandens could become an alternative to syn-
thetic fungicides for use in agro-industries and also to screen
and develop such novel types of selective and natural fungi-
cides in the treatment of many microbial plant pathogens caus-
ing severe destruction to crop, vegetable and ornamental
plants.
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Chemical composition and antifungal properties of the essential oil and various extracts of Mikania 5
Please cite this article in press as: Siddiqui, S.A. et al., Chemical composition and antifungal properties of the essential oil and various
extracts of Mikania scandens (L.) Willd. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.07.050