Fitoterapia 78 (2007) 319–322www.elsevier.com/locate/fitote

Short report

Composition and antifungal activity of the essential oil of Seseliannuum wild-growing in Serbia

Slobodan Milosavljević a,⁎, Vele Tešević a, Ivan Vučković b, Milka Jadranin b,Vlatka Vajs b, Marina Soković c, Peđa Janaćković d, Anka Jovanović e

a Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbiab Institute for Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Serbia

c Department of Plant Physiology, Mycological Laboratory, Institute for Biological Research, Bulevar Despota Stefana 142,11 000 Belgrade, Serbia

d Faculty of Biology, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbiae Institute of Public Health, Bulevar Despota Stefana 54a, 11000 Belgrade, Serbia

Received 20 January 2006; accepted 6 March 2007Available online 12 April 2007

Abstract

The essential oil from the aerial parts of Seseli annuum, wild-growing in Serbia, was obtained by hydrodistillation and analyzedusing GC and GC/MS. A total of 43 components were identified representing 96.5% of S. annuum oil. The most abundantcompounds were germacrene D (29.8%), sabinene (10.3%), β-ocimene Z (9.8%) and limonene (8.6%). The essential oil showedantifungal activity against fifteen fungi with MICs between 12.5 to 50 μl/ml.© 2007 Elsevier B.V. All rights reserved.

Keywords: Seseli annuum; Essential oil; Germacrene D; Antifungal activity

1. Plant

Seseli annuum aerial part (Apiaceae) was collected in Deliblatska Peščara (Deliblato Sand) in South Banat(Vojvodina), in July 2005. A voucher specimen (SA072005) was deposited in the Herbarium of the Botanic Garden“Jevremovac”, Faculty of Biology, University of Belgrade.

2. Uses in traditional medicine

Seseli comprises 55 species distributed mainly in Europe. Ten of them could be found in Serbia [1]. Seseli containsnumerous species that have been used in folk medicine since ancient times [2].

⁎ Corresponding author. Tel.: +381 11 630 474; fax: +381 11 636 061.E-mail address: smilo@chem.bg.ac.yu (S. Milosavljević).

0367-326X/$ - see front matter © 2007 Elsevier B.V. All rights reserved.doi:10.1016/j.fitote.2007.03.014

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3. Previously isolated classes of constituents

Seseli spp. are a well-known source of the linear or angular pyranocoumarins that possess antiproliferative [3],antiviral [4] or antibacterial [5] activities. Previous studies on the S. annuum reported the isolation of sesquiterpenequinones [6] and coumarin derivatives [7].

Table 1Composition of the essential oil of S. annuum

Peak no. Compounds RI a Content (%)

1 α-Thujene 931 t2 α-Pinene 939 5.13 Camphene 953 0.64 Sabinene 976 10.35 β-Pinene 980 1.96 β-Myrcene 991 5.07 n-Octanal 1001 t8 α-Terpinene 1018 t9 p-Cymene 1026 t10 Limonene 1031 8.611 β-Ocimene E 1040 2.212 β-Ocimene Z 1050 9.813 γ-Terpinene 1062 0.314 iso-Piperiton 1095 t15 allo-Ocimene 1129 t16 Limonene oxide 1139 0.217 4-Terpineol 1177 0.618 Geranial 1270 t19 Bornyl acetate 1285 t20 α-Copaene 1376 1.621 Bourbonene 1384 0.422 β-Cubebene 1390 1.323 β-Elemene 1391 0.824 β-Cedrene 1418 t25 β-Caryophyllne 1418 4.426 β-Gurjunene 1425 0.327 β-Farnesene Z 1443 0.628 β-Farnesene E 1458 1.029 Germacrene D 1486 29.830 α-Farnesene E,E 1500 1.831 δ-Cadinene 1522 1.632 Elemicin 1554 0.833 Nerolidol 1564 0.534 Spathulenol 1576 0.835 Caryophyllene oxide 1584 1.636 allo-Aromadendrene epoxide 1595 0.637 α-Cadinol 1653 0.938 Oxo-β-ionone 1665 0.739 Khusinol 1674 0.640 Nootkatone 1800 0.441 Methyl palmitate 1927 t42 Palmitic acid 1968 0.843 Phytol 2100 0.6Total identified 96.5

t = trace (less than 0.1%).a Obtained using retention times of n-alkanes under the same GC conditions (DB-5 column).

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4. Tested material

Essential oil was obtained by hydrodistillation of the aerial parts in a Clevenger type glass apparatus (yield: 0.14%,ρ=0.96 mg/ml). A library search and MS deconvolution and extraction were performed using NIST AMDIS(Automated Mass Spectral Deconvolution and Identification System) software version 2.4. The search was performedagainst our own Library, containing 4951 spectra.

5. Studied activity

Antifungal activity of the oil was determined using the modified mycelial growth test [8].

6. Used microorganisms

The organisms used were obtained from Mycotheca of the Mycological Laboratory, Department of PlantPhysiology, Institute for Biological Research, Belgrade. Among tested species were dermatomycetes (Trichophytonmentagrophytes, T. rubrum, T. tonsurans, Epidermophyton floccosum, Microsporum canis, M. gypseum), obtaineddirectly from the patients at the Centre for Preventive Medicine, MMA, Belgrade.

7. Results

Chemical composition of essential oil is reported in Table 1. The results of antifungal activity are given in Table 2.

8. Conclusions

A total of 43 components were identified representing 96.5% of S. annuum oil (Table 1). Two major groups ofidentified compounds were monoterpene and sesquiterpene hydrocarbons (43.8% and 43.6%, respectively). The majormonoterpene components were sabinene (10.3%), β-ocimene Z (9.8%) and limonene (8.6%). The most abundantcompound in the oil was sesquiterpene germacrene D (29.8%). In the previous investigations, the oils obtained fromsome Seseli spp. were rich in monoterpene hydrocarbons, especially α-pinene [9–11]. Two subspecies of S.gummiferum showed high content of sesquiterpene germacrene B and spathulenol [12]. The results obtained from themodified mycelial growth test showed that the essential oil was highly effective in inhibiting the growth of fifteen fungi.The oil possessed antifungal activity with minimal inhibitory concentration (MIC) in the range of 12.5–50.0 μl/ml,while the commercial preparation of fungicidal agent, containing 1% (w/v) of bifonazole in EtOH, showed higherMICs,

Table 2MICs of S. annuum essential oil on fungi

Fungi Essential oil (μl/ml) Bifonazole (μl/ml) a

Alternaria alternata 12.5 50.0Aspergillus niger 25.0 50.0A. ochraceus 25.0 50.0A. versicolor 25.0 50.0A. flavus 50.0 50.0A. terreus 25.0 50.0Cladosporium cladosporioides 12.5 25.0Fusarium tricinctum 12.5 25.0Penicillium ochrochloron 50.0 100.0P. funiculosum 50.0 100.0Phomopsis helianthi 12.5 25.0Trichoderma viride 50.0 100.0Trichophyton mentagrophytes 25.0 25.0Microsporum canis 12.5 25.0Epidermophyton floccosum 12.5 25.0

a Commercial preparation containing 1% (w/v) of bifonazole in EtOH (“Srbolek”, Belgrade, Serbia).

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i.e. 25.0–100.0 μl/ml (Table 2). The essential oil showed high antifungal properties against all the fungal species testedwhich may be useful for practical purposes.

Acknowledgment

The authors are grateful to the Ministry of Science, Technologies and Development of Serbia for the financialsupport, Grant No. 142053.

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