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Composition and In Vitro antifungal activity of essential oils of Erigeron canadensis and Myrtus communis from FRANCE

DOI:10.1023/A:1024818015122
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Massimo Curini at Università degli Studi di Perugia
Massimo Curini
A. Bianchi
A. Bianchi
A. Bianchi
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F. Epifano
F. Epifano
F. Epifano
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Renato Bruni at Università di Parma
Renato Bruni
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Abstract and Figures

Essential oils of Erigeron canadensis L. and Myrtus communis L. were tested in vitro as growth inhibitors against phytopathogenic fungi Rhizoctonia solani Kuhn, Fusarium solani (Mart.) Sacc. and Colletotrichum lindemuthianum (Sacc. & Magn.) Briosi & Cav. Both showed weak fungicidal acitivity, except the essential oil of M. communis that exerted a 60% growth inhibition against R. Solani at a dose of 1600 ppm. Microscopic observation revealed that the essential oil of M. Communis caused morphological alterations of hyphae of all fungi at 1600 ppm, while, at the same dose, only the hyphal morphology of C. Lindemuthianum was affected by the essential oil of Er. Canadensis.
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1)Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Via del Liceo I – 06123 Perugia,
Italy; e-mail: curmax@unipg.it; fax: +390755855116; 3) Dipartimento di Biologia Evolutiva e Funzionale, Area delle Scienze
11/A, Università degli Studi, 43100 Parma, Italy; 3) Dipartimento SENFIMIZO, Settore Fitopatologia, Università degli Studi,
Palermo, Italy; 4) Dipartimento di Protezione e Valorizzazione Agroalimentare, Unviersità degli Studi, Bologna, Italy.
Published from Khimiya Prirodnykh Soedinenii, No. 2, pp. 144-146, March-April, 2003. Original article submitted March 26,
2003.
0009-3130/03/3902-0191$25.00 ©2003 Plenum Publishing Corporation 191
Chemistry of Natural Compounds, Vol. 39, No. 2, 2003
COMPOSITION AND IN VITRO ANTIFUNGAL ACTIVITY
OF ESSENTIAL OILS OF Erigeron canadensis
AND Myrtus communis FROM FRANCE
M. Curini,1 A. Bianchi,2 F. Epifano,1 R. Bruni,2 UDC 547.913
L. Torta,3 and A. Zambonelli4
Essential oils of Erigeron canadensis L. and Myrtus communis L. were tested in vitro as growth inhibitors
against phytopathogenic fungi Rhizoctonia solani Kuhn, Fusarium solani (Mart.) Sacc. and Colletotrichum
lindemuthianum (Sacc. & Magn.) Briosi & Cav. Both showed weak fungicidal acitivity, except the essential
oil of M. communis that exerted a 60% growth inhibition against R. solani at a dose of 1600 ppm.
Microscopic observation revealed that the essential oil of M. communis caused morphological alterations
of hyphae of all fungi at 1600 ppm, while, at the same dose, only the hyphal morphology of C.
lindemuthianum was affected by the essential oil of Er. canadensis.
Key words: Erigeron canadensis, Myrtus communis, mycelial inhibition, phytopathogenic fungi.
During the last years there has been growing interest in testing natural compounds of different origins as defense for
cultivated plants against phytopathogenic fungi [1]. In particular, essential oils were seen to exert good antifungal activities
both in vitro and in vivo [2–9]. Although pharmacological activities of many essential oils have been described in the literature
[10], their activity against phytopathogenic fungi has been less investigated. In the present work we wish to report the chemical
composition and in vitro growth inhibition activity against three phytopathogenic fungi Rhizoctonia solani Kuhn, Fusarium
solani (Mart.) Sacc. and Colletotrichum lindemuthianum (Sacc. & Magn.) Briosi & Cav. of essential oils of Erigeron canadensis
L. and Myrtus communis L. collected in France.
The chemical composition of essential oils of Er. canadensis and M. communis are reported in Tables 1 and 2
respectively. The essential oil of Er. canadensis contained 18 compounds, limonene being the main one (76.03%). The essential
oil of M. communis contained 14 compounds,
α
-pinene and 1,8-cineol (eucalyptol) together representing around 86%.
Data reported in Tables 3 and 4 revealed that R. solani growth is slightly inhibited only at the highest dose (1600 ppm)
using the essential oil of Er. canadensis, while growth inhibition of this fungus reached 28% at a dose of 800 ppm using the
essential oil of M. communis and became doubled (60%) by doubling the dose of the oil. F. solani growth was very little
inhibited (4.50%) using the essential oil of Er. canadensis at a dose of 400 ppm, but increasing the dose up to 1600 ppm
increased the percentage of inhibition slightly (12.71%). The same pattern was recorded for F. solani using the essential oil
of M. communis, the highest percentage of growth inhibition being 15.59% at 1600 ppm. C. lindemuthianum growth inhibition
was 18.75% at a 400 ppm dose of the essential oil of Er. canadensis and increased up to 29.27% at 1600 ppm. Treatment with
the essential oil of M. communis resulted in little growth inhibition (21.41%) at 1600 ppm, while lower doses favored the growth
of C. lindemuthianum cultures, although in a very low percentage (2.56%); a similar effect was already observed using other
essential oils [4]. At lower doses, both essential oils did not modify the morphological features of fungi cultures, as seen by
microscopic observations. At higher doses (1600 ppm) the morphology of hyphae changed: in particular, using the essential oil
192
TABLE 1. Retention Indices (Ri) and Percentage Chemical Composition of Essential Oil
of E. canadensis
Compounds Ri%*
α
-Pinene
β
-Pinene
β
-Myrcene
Cosmene
Limonene
∆
3-Carene
Thujone
Camphor
Isoborneol
Menthol
Isobornyl acetate
β
-Caryophyllene
Epi-bicyclosesquiphellandrene
α
-Santalene
Germacrene D
α
-Cariophyllene
β
-Sesquiphellandrene
Germacrene B
942
978
988
1001
1025
1027
1100
1126
1149
1168
1279
1428
1431
1435
1468
1469
1472
1477
Tr.
1.57±0.06
3.62±0.04
0.32±0.04
76.03±0.07
3.87±0.03
1.70±0.04
0.39±0.06
Tr.
0.23±0.05
0.17±0.05
2.13±0.05
0.34±0.06
5.84±0.04
0.16±0.04
1.50±0.05
0.35±0.02
1.78±0.07
______
*Values expressed as mean of 3 measurements ± S.D.
TABLE 2. Retention Indices (Ri) and Percentage Chemical Composition of Essential Oil
of M. communis
Compounds Ri%*
α
-Pinene
β
-Pinene
Iso-butyl iso-butyrate
1,8-Cineol
4-Carene
Linalool
Terpinen-4-ol
α
-Terpineol
Linalyl butyrate
α
-Terpineol acetate
Geranyl acetate
β
-Cariophyllene
Germacrene D
α
-Cariophyllene
942
978
989
1017
1043
1097
1129
1178
1325
1333
1363
1428
1468
1469
52.90±0.07
0.66±0.05
0.64±0.07
32.92±0.04
0.79±0.02
4.21±0.03
0.42±0.03
2.46±0.06
0.52±0.06
0.64±0.05
1.64±0.04
1.33±0.04
0.33±0.05
0.54±0.02
______
*Values expressed as mean of 3 measurements ± S.D.
of Er. canadensis resulted in alterations of hyphae of C. lindemuthianum, which appeared dichotomously branched in the apical
portion. Treatment with the essential oil of M. communis resulted in structural damages of hyphae of R. solani, although the
diameter of treated hyphae did not change when compared to that of control ones (7.16 mm and 7.15 mm respectively); hyphae
of F. solani appeared more thick and corrugated than untreated ones, which appeared to grow linearly; hyphae of F. solani and
of C. lindemuthianum appeared more branched and irregularly shaped than untreated ones.
193
TABLE 3. Percentage of Growth Inhibition of the Tested Phytopathogenic Fungi Treated with Different
Concentrations of Essential Oil of Er. canadensis
Dose (ppm) % growth inhibition*
R. solani F. solani C. lindemuthianum
100
400
800
1600
n.d.
n.d.
n.d.
22.35±3.63
n.d.
4.50±2.03
8.53±1.79
12.71±1.28
n.d.
18.75±7.37
22.10±3.60
29.27±1.22
______
*Values expressed as mean of 8 measurements ± S.D.
n.d. = Not detected.
TABLE 4. Percentage of Growth Inhibition of Phytopathogenic Fungi Treated with Different Concentrations
of Essential Oil of M. communis
Dose (ppm) % growth inhibition*
R. solani F. solani C. lindemuthianum
100
400
800
1600
n.d.
n.d.
28.09±2.47
60.00±2.84
1.76±0.59
1.18±1.57
2.55±0.90
15.59±0.42
-2.56±3.45
4.43±1.16
13.12±3.17
21.41±1.04
______
*Values expressed as mean of 8 measurements ± S.D.
n.d. = Not detected.
The essential oils of Er. canadensis and M. communis were shown to exert growth inhibition activity against three
phytopathogenic fungi, R. solani Kuhn, F. solani (Mart.) Sacc. and C. lindemuthianum (Sacc. & Magn.) Briosi & Cav., although
the observed activities were less than those reported for the essential oils of thyme and mint against the same fungi [8]. C.
lindemuthianum was shown to be more susceptible towards the essential oil of Er. canadensis: in this case growth inhibition
was accompanied by deep modification of hyphae morphology. R. solani was the more susceptible strain towards the essential
oil of M. communis, revealing a good percentage (60%) of growth inhibition at higher doses. Moreover, also in this case, marked
modifications in hyphae morphology were detected: they appeared, collapsed probably due to dehydration induced by the oil
components. Similar morphological modifications were reported for the same fungus using the essential oil of thyme. The
fungicidal activity of essential oils of Er. canadensis and M. communis may be due to their main components, limonene,
α
-pinene, and 1,8-cineol, respectively. In fact, the antifungal properties of these monoterpenes have been well documented in
the literature [3, 7]. Studies of the in vivo properties of the essential oils from Er. canadensis and M. communis against
phytopathogenic fungi are now in progress in our laboratories.
EXPERIMENTAL
The chemical composition of each oil was determined by GC-MS analysis using a Hewlett Packard 6890 gas
chromatography equipped with a 12.5 m × 0.25 mm MetSil column coupled to HP ChemStation Software. The carrier gas was
helium at a pressure of 3.5 kg/cm2 and the column temperature was programmed from 50°C to 270°C at 4°C/min. The
chromatogram was obtained using a reporting integrator and the composition recorded as percent area. Mass spectra were
obtained from a GC-MS system, operating in the EI mode at 70 eV, equipped with a 12.5 m × 0.25 mm MetSil column and an
194
HP 5973 Mass Selective Detector, using the same chromatographic conditions reported above. The column was connected to
the mass spectrometer ion source via an open split interface heated at 250°C. Identification of chemical constituents was based
on a comparison of their retention indices (Ri) [11] and mass spectra obtained from commercially available samples and from
the Nist98 Mass Spectral Database. Rhizoctonia solani Kuhn strains were obtained from thyme seedlings, Fusarium solani
(Mart.) Sacc. strains were obtained from the CBS culture collection (Utrecht, The Netherlands) no. 231.31, and Colletotrichum
lindemuthianum (Sacc. & Magn.) Briosi & Cav. strains were isolated from bean plants. All fungi were cultivated in agar-potato
culture medium (PDA, Difco). Antifungal activity was assayed in 8.5 cm diameter Petri dishes containing a PDA culture
medium. The essential oil of Er. canadensis was used as 50% v/v solution in absolute ethanol; the essential oil of M. communis
was used as 12.5% v/v solution in 80% ethanol [12]. Each solution was added to the PDA culture medium at 40–45°C then put
in Petri dishes. Essential oils were assayed at doses of 100, 400, 800, and 1600 ppm and 5 Petri dishes were treated twice with
each dose level. PDA culture mediums containing only ethanol were used as controls. Fungi were collected from the external
border of active growing cultures and inoculated in the form of a 5 mm diameter disc in each dish. Petri dishes were incubated
at 22 ± 1°C. Fungal growth was detected 2, 5, 7, and 10 days after inoculation by measuring the diameters of colonies. The
antifungal activity of essential oils was measured at the highest mycelar growth stage of cultures in control dishes and calculated
as percentage of mycelar growth inhibition as reported by Pandey and coworkers [5]. Morphological variations of cultures were
detected 7 days after inoculation by microscopic observation (Leitz Laborlux 12 optical microscope), and images were taken
by a JVC camera connected to a personal computer. The diameters of the hyphae were calculated by an Axio.Vision 2.05 (Zeiss)
computer program.
Antifungal activity of each oil is reported in Tables 3 and 4.
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5. D. K. Pandey, N. N. Tripathi, R. D. Tripathi, and S. N. Dixit, Z. PflKrankh PflSchutz, 89, 344 (1982).
6. L. Rovesti, S. Di Marco, and D. Pancaldi, Z. PflKrankh PflSchutz, 99, 293 (1992).
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İnsan endotelyal hücre spesifik molekül (ESM-1) olarak bilinen Endokan ilk kez 1996 yılında insan endotelyal hücrelerinden klonlanmıştır (1). 5. kromozomun uzun kolunda 3 ekson ve araya giren 2 introndan oluşan tek gen tarafından kodlanmaktadır. Primatlar ve memelilerde yüksek derecede korunmuş bir gene sahiptir. İlerleyen çalışmalar molekülün proteoglikan ailesinin üyesi olduğunu göstermiştir. Protein yapıdaki merkez kısım 165 amino asit içermektedir. 137. pozisyondaki serin amino asitine translasyon sonrası modifikasyon ile bağlı tek dermatan sülfat bulunmaktadır. N-terminal sisteinden zengin 110 amino asit içeren kısım ve C-terminal sisteinden fakir kısım olmak üzere iki temel bölümden meydan gelir (2). Endokan proteoglikan ailesinin diğer üyelerinden bazı özellikleri nedeni ile farklıdır. Fazla sayıda glikozaminoglikan içeren büyük moleküllü proteoglikanların aksine 20 kDa ağırlığında tek zincire sahiptir (1). Bunu yanı sıra, hücre dışı yatağın diğer elemanları gibi hücrelere yapısal destek olmanın ötesinde Endokan, temelde sekretuvar bir moleküldür (3).
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Effect of neem kernel extract on some phytopathogenic fungi under greenhouse conditions.
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  • Jan 1992
The effect of an aqueous neem kernel extract on some important diseases of different herbaceous crops was assessed in vivo, under greenhouse conditions, in comparison with some chemical fungicides. The protection provided by the extract against powdery' mildews (Sphaerotheca fuliginea, Erysiphe graminis f. sp. tritici and hordei) was comparable to that given by sulphur, when used both prophylactically and curatively. Although not as effective as the fungicide mancozeb, the neem extract also gave a significant control of Puccinia recondita, f. sp. tritici, while it was ineffective against Phytophthora infestans, Cercospora beticola and Septoria apiicola.
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Rapid Evaluation of Plant Extracts and Essential Oils for Antifungal Activity Against Botrytis cinerea
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A rapid assay to determine antifungal activity in plant extracts and essential oils is described. Wells in microtiter plates were loaded with Botrytis cinerea spores and plant extracts or essential oils. Subsequent changes in optical density following spore germination in the wells was measured after 24 h using an automatic microtiter plate reader driven by a software program developed for this purpose. Extracts from 345 plants and 49 essential oils were evaluated for their antifungal activity against B. cinerea. Among 345 plant extracts analyzed, 13 showed high levels of antifungal activity, with species of Allium and Capsicum predominating. Among the 49 essential oils tested, palmarosa (Cymbopogon martini), red thyme (Thymus zygis), cinnamon leaf (Cinnamomum zeylanicum), and clove buds (Eugenia caryophyllata) demonstrated the most antifungal activity against B. cinerea. The most frequently occurring constituents in essential oils showing high antifungal activity were: D-limonene, cineole; beta-myrcene; alpha-pinene, beta-pinene; and camphor.
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