Antifungal, antioxidant and anti-inflammatory activities of Oenanthe crocata L. essential oil

doi:10.1016/j.fct.2013.08.083

Food and Chemical Toxicology

Volume 62, December 2013, Pages 349-354

https://doi.org/10.1016/j.fct.2013.08.083 Get rights and content

Highlights

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Oenanthe crocata essential oil: chemical composition, antifungal, antioxidant and anti-inflammatory properties.
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The oil was particularly active against dermatophytes and Cryptococcus neoformans.
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Both the oil and sabinene demonstrated anti-inflammatory activity at concentrations safe to macrophages and keratinocytes.
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These results support the use of the oil and sabinene for the management of dermatophytosis and/or inflammatory diseases.

Abstract

The present study reports the chemical composition, antifungal, antioxidant and anti-inflammatory properties as well as the cytotoxicity of Oenanthe crocata essential oil and one of its main compounds.

The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analysed by GC and GC/MS. The oil was predominantly composed of monoterpene hydrocarbons (85.8%), being the main compounds trans-β-ocimene (31.3%), sabinene (29.0%) and cis-β-ocimene (12.3%). For the antifungal activity, the minimal inhibitory and minimal lethal concentrations (MICs and MLCs) were determined. The oil was particularly active against dermatophytes and Cryptococcus neoformans, with MIC values ranging from 0.08 to 0.16 μL/mL. Regarding the anti-inflammatory activity, both the oil and sabinene demonstrated strong anti-inflammatory activity through nitric oxide (NO) production inhibition in lipopolysaccharide (LPS) plus interferon gamma (IFN-γ)-triggered macrophages. Furthermore, the essential oil showed a potent NO scavenging effect and inhibited inducible NO synthase expression. Interestingly, and although we detected a cytotoxic effect in macrophages and keratinocytes for the highest concentrations tested of the oil and sabinene, we also disclosed bioactive and safe concentrations to be further explored for therapeutic proposes. Taking together, these results support the use of the oil and sabinene for the management of dermatophytosis and/or inflammatory-related diseases.

Introduction

The incidence and severity of microbial infections have increased over the last years, particularly in patients with impaired immunity derived from the use of cytotoxic drugs, immunosuppressive therapy, intensive care units and following treatment with broad-spectrum antimicrobials (Pina-Vaz et al., 2004). The small number of available antifungals and the increase of fungi resistance justify the search for effective alternatives.

Natural products have played an important role worldwide in the treatment and prevention of fungal infections and pathologies with a strong inflammatory component, with several studies referring the therapeutic properties of these metabolites (Adorjan and Buchbauer, 2010, Chin et al., 2006, Edris, 2007, Miguel, 2010).

Aromatic plants, such as those from Lamiaceae and Apiaceae families produce a large number of secondary metabolites, namely monoterpenes, sesquiterpenes and phenylpropanoids (Moreno-Dourado et al., 2000), which have demonstrated several therapeutic properties, mainly antioxidant, antifungal and anti-inflammatory ones (e.g. Figueiredo et al., 2008, Tavares et al., 2010, Zuzarte et al., 2012). However, for many species, only few studies elucidate their mechanisms of action and safety, justifying further investigations for the development of phytopharmaceuticals.

Within the Apiaceae family some species are recognized for their high toxicity while others are widely used as traditional remedies. The genera Oenanthe (Apiaceae) comprises ten species, being some of them widely used by local communities. For example, the essential oils of Oenanthe javanica leaves are used in traditional Chinese medicine for the treatment of inflammatory conditions. Also Han et al. (2008) showed the anti-hepatitis B virus activity of total phenolics from this species.

Oenanthe crocata L. is a perennial species very frequent throughout the Mediterranean region. This species is known for its high root toxicity (Kite et al., 2006). However, the flowers and leaves of these plants have been used for a long time in traditional medicine for brain-related disorders and dermatological affections. Concerning the essential oils of this species only two studies have been performed before. Bonsignore et al. (2004) reported the antiviral and antimicrobial activities of the essential oils from seeds and Bicchi et al. (2009) evaluated the HIV-1- inhibiting activity of the oils from the aerial parts of the plant.

In order to investigate the potential therapeutic use of the aerial parts of O. crocata, this study reports the cytotoxicity, antioxidant, and antifungal properties of its essential oil. Furthermore, the anti-inflammatory activity of the oil was evaluated by measuring the production of NO and iNOS expression on LPS-stimulated macrophages. As far as is known the antioxidant and anti-inflammatory potential of this species has not been evaluated before.

Section snippets

Plant material

Aerial parts of the plants were collected at the flowering stage, in June 2011 in Eiras (Coimbra, Portugal). The plants were identified by a taxonomist (Dr. Jorge Paiva, University of Coimbra), and a voucher specimen (No. 24011) was deposited at the Herbarium of the Faculty of Pharmacy of the University of Coimbra.

Reference and pure compounds

Authentic samples of sabinene (Fluka, ⩾90% purity) and ocimene (SAFC, ⩾90% purity) were used. Fluconazole was kindly provided by Pfizer (pure powder) and amphotericin B by Sigma

Essential oil analysis

O. crocata essential oil was obtained with a yield of 0.3% (v/w). The qualitative and quantitative compositions of the oil are presented in Table 1, where compounds are listed in order of their elution on a polydimethylsiloxane column. Monoterpene hydrocarbons were the most abundant (85.8%), being the main constituents trans-β-ocimene (31.3%), sabinene (29.0%) and cis-β-ocimene (12.3%). The essential oil composition is similar to that reported for the aerial parts of O. crocata from Sardinia (

Conclusions

O. crocata is recognized as a very poisonous plant with several studies pointing out the presence of toxic compounds and lethal intoxications. However, the essential oil of the aerial parts of the plant, flowers without seeds, do not present toxic compounds and showed very relevant therapeutic properties.

Our results show that O. crocata oil and one of its main compounds, sabinene, may be a source of antifungal, antioxidant and anti-inflammatory drugs for the food, cosmetic and pharmaceutical

Conflict of Interest

The authors declare that there are no conflicts of interest.

Acknowledgements

This work was funded through national funds from FCT – Fundação para a Ciência e a Tecnologia under the project PEst-OE/SAU/UI0177/2011 and by a Ph. D. fellowship to Mónica Zuzarte (SFRH/BD/40218/2007).

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View full text

Antifungal, antioxidant and anti-inflammatory activities of Oenanthe crocata L. essential oil

Highlights

Abstract

Introduction

Section snippets

Plant material

Reference and pure compounds

Essential oil analysis

Conclusions

Conflict of Interest

Acknowledgements

J. Chromatogr. A.

Anal. Biochem.

J. Cromatogr. B.

J. Immunol. Methods

J. Ethnopharmacol.

Food Chem.

Identification of essential oil components by gas chromatography/mass spectroscopy

Biological properties of essential oils: an updated review

Flavour Frag. J.

HIV-1-inhibiting activity of the essential Oil of Ridolfia segetum and Oenanthe crocata

Planta Med.

Analysis of the essential oil of Oenanthe crocata L. and its biological activity

J. Essent. Oil Res.

Drug discovery from natural sources

AAPS J.