Activities of essential oils from Asarum heterotropoides var. mandshuricum against five phytopathogens

doi:10.1016/j.cropro.2009.12.007

Crop Protection

Volume 29, Issue 3, March 2010, Pages 295-299

https://doi.org/10.1016/j.cropro.2009.12.007 Get rights and content

Abstract

Some secondary metabolites of plants function as antimicrobial products against phytopathogens and constitute an increasingly important class of pesticides. In the present study, the essential oil of Asarum heterotropoides var. mandshuricum was analyzed by GC/MS and its antimicrobial activity was evaluated against five phytopathogenic fungi. Major components of the oil were methyleugenol (59.42%), eucarvone (24.10%), 5-allyl-1,2,3-trimethoxybenzene (5.72%), and 3,7,7-trimethylbicyclo(4.1.0)hept-3-ene (4.93%). The essential oil and the most abundant component, methyleugenol, were separately assayed for inhibition of 5 pathogens: Alternaria humicola, Colletotrichum gloeosporioides, Rhizoctonia solani, Phytophthora cactorum and Fusarium solani. Both the oil and methyleugenol strongly inhibited the growth of the test pathogens (IC₅₀ values <0.42 μg ml⁻¹) except F. solani, with the best activity against P. cactorum (IC₅₀ values = 0.073 and 0.052 μg ml⁻¹, respectively). It is concluded that the essential oil of A. heterotropoides var. mandshuricum has a broad antiphytopathogenic spectrum, and that methyleugenol is largely responsible for the bioactivity of the oil. The mode of action of methyleugenol against P. cactorum is discussed based on changes in the mycelial ultrastructure.

Introduction

In recent decades, plant products have come to be exploited as botanical pesticides because they are more biodegradable than synthetic pesticides (Duke, 1990). In addition, many pathogens have become a serious threat to crops due to their resistance to known chemical control agents including benzimidazoles, demethylation inhibitors, Qo respiration inhibitors and dicarboximides (Ma and Michailides, 2005, Ishii, 2006). This has occasioned a growing effort in the search for new bioactive products (Duke, 1990, Gigante et al., 2002). A great number of plant essential oils exhibit antimycotic properties and are potential antifungal products (Deans et al., 1989, Lee et al., 2008, Chang et al., 2008). One such essential oil is that from Asarum heterotropoides F. Schmidt var. mandshuricum (Maxim.) Kitag (Maximowicz) Kitagawa (Aristolochiaceae) (Liu et al., 2007, Wang et al., 2008).

A. heterotropoides var. mandshuricum, a perennial herb endemic to China, is a traditional Chinese medicine by the name of Xixin (Huang et al., 2003). It can be found in forests, mountain slopes, valleys and moist shady areas. It is occasionally cultivated in the Heilongjiang, Jilin, Liaoning and South China regions (Huang et al., 2003). Its essential oil is used for analgesic, antitussive, and anti-allergic purposes in China (Hashimoto et al., 1994). The components in the essential oil had been investigated (Zeng et al., 2004, Zhang et al., 2004) and a total of 82 components were identified, of which methyleugenol was found to be the most abundant (Kosuge et al., 1978, Zeng et al., 2004).

In previous investigations, this essential oil was found to possess the promising antifungal activity against a variety of plant pathogens (Liu et al., 2007, Wang and Ji, 2007, Wang et al., 2008). However, the antifungal constituents in the oil were not determined. Nevertheless, we could assume that methyleugenol might be the main constituent responsible for the bioactivity of the A. heterotropoides var. mandshuricum essential oil from the following facts: the compound is not only the most abundant component of this oil, but it is also widely distributed in the other aromatic plants which possess a wide spectrum of activities against microorganisms ranging from bacteria to fungi (Kivanç, 1988); its antifungal activity against Botrytis cinerea Pers and Colletotrichum fragariae Brooks had been reported in Artemisia dracunculus L. var. dracunculus by Meepagala et al. (2002). In order to verify our assumption and elucidate the main constituents responsible for the activity of the oil, we analyzed the essential oil of A. heterotropoides var. mandshuricum by GC/MS, evaluated the antifungal activity of the oil and methyleugenol against five representatives of plant pathogens causing great damages in crops, and explored the mode of action of the main active component.

Section snippets

Plant materials

Dried whole plant of A. heterotropoides var. mandshuricum was collected from Xinbin Manchus (N 125.6°, E 41.42°), Liaoning, China. A voucher specimen (No. 262) was deposited in the herbarium of the Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, China.

Preparation of essential oils and chemical reference substance

Dried plant material (600 g) was chopped into small pieces and subjected to hydrodistillation for 8 h, using a Clevenger-type apparatus to yield 6.87 g (1.15%) of a light brown oil. The essential oil was dissolved in

Major chemical components of the essential oil

In total, 32 peaks were detected by GC/MS and only the major constituents are shown in Table 1. Seven compounds were identified by GC/MS and by the retention indexes, including terpenes and phenylpropanes. The oil was dominated by methyleugenol (59.42%), eucarvone (24.10%), 5-allyl-1,2,3-trimethoxybenzene (5.72%) and 3,7,7-trimethylbicyclo(4.1.0)hept-3-ene (4.93%), and also included 2,6,6-trimethylbicyclo(3.1.1)hept-2-ene (0.42%), (1S)-(1)-beta-pinene (0.75%), and 1,3-dimethoxy-5-methylbenzene

Discussion

The main results in the present study was consistent with those previous investigations in which, the essential oil of A. heterotropoides var. mandshuricum exhibited antifungal activities against pathogens such as Gloeosporium sp., Pestalotiopsis sp., Actinonema rosae (Lib.) Fr., Alternaria spp., Fusarium spp., Bipolaris spp., Curvularia lunata (Wakker) Boedijn Ustilago maydis (DC.) Corda with IC₅₀ values <400 μg ml⁻¹ (Liu et al., 2007, Wang and Ji, 2007). However, the activity of the essential

Acknowledgements

This study was supported by the IMPLAD foundation (1391) and the National Key Technology R&D Program (2006BAI09B03). We thank Ms. Chen H. J. in Chinese Forest University for GC/MS analysis, and Mr. Jia W.J. and Ms. Liu M.F. for TEM. Authors are thankful to Prof. Wei X.Y. and Prof. Liu X.Z. for reading the manuscript.

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Activities of essential oils from Asarum heterotropoides var. mandshuricum against five phytopathogens

Abstract

Introduction

Section snippets

Plant materials

Preparation of essential oils and chemical reference substance

Major chemical components of the essential oil

Discussion

Acknowledgements

J. Plant Physiol.

Bioresour. Technol.

Trends Microb.

Crop Prot.

Pestic. Biochem. Phys.

Infectivity to potato, sporangial germination, and resperation of isolates of Phytophthora infestans from metalaxyl-sensitive and metalaxyl-resistant population

Phytopathology

Biocontrol of Phytophthora cactorum in vitro with Enterobacter aerogenes

N.Z. J. Crop Hortic. Sci.

In vitro variability among isolates of eight Phytophthora species in response to metalaxyl

Phytopathology

The essential oils of Peperomia pellucida Kunth and P. circinnata Link var. circinnata

Flavour. Frag. J.

Biological activity of plant volatile oils and their constituents

Planta Med.

Natural pesticides from plants

Structural effects on the bioactivity of dehydroabietic acid derivatives

Planta Med.

Headspace solid phase microextraction for screening for the presence of resins in Egyptian archaeological samples

J. Sep. Sci.

Studies on anti-allergic components in the roots of Asiasarum sieboldi

Planta Med.

Aristolochiaceae

Impact of fungicide resistance in plant pathogens on crop disease control and agricultural environment

Jpn. Agric. Res. Q.

Composition, quality control, and antimicrobial activity of the essential oil of long-time stored dill (Anethum graveolens L.) seeds from Bulgaria

J. Agric. Food Chem.

Antimicrobial activity of “Çörtük” (Echinophora sibthorpiana Guss.) spice, its essential oil and methyl-eugenol

Food/Nahrung