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Phytochemical, Antibacterial, Antifungal and Antioxidant Properties of Agastache foeniculum Essential Oil

  • April 2017
Authors:
Mohammad Hashemi at Mashhad University of Medical Sciences
Mohammad Hashemi
Ali Ehsani at Tabriz University of Medical Sciences
Ali Ehsani
Abbas Hassani at Urmia University
Abbas Hassani
Asma Afshari at Mashhad University of Medical Sciences
Asma Afshari
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Phytochemicals are good sources of natural antioxidants and have beneficial effects on human health. Many of phenolic phytochemicals have shown antimicrobial and antifungal activity. Anise hyssop (Agastache foeniculum [Pursh] Kuntze) is a perennial aromatic plant of the Lamiaceae family with antimicrobial and antifungal properties and useful for gastrointestinal problems. In this investigation, the antioxidant activity of extracts, their antimicrobial activity against Staphylococcus aureus, Listeria monocytogenes, Bacillus cereus, B. subtilis, Salmonella thyphimurium, S. enteritidis, Escherichia coli strains and their antifungal activity against Aspergillus niger and A. flavus was evaluated. Seven components were identified, representing 95.4% of the oils including methyl chavicol (83.1%), limonene (3.4%), spathulenol (3.1%) and caryophyllene oxide (3.1%). Agar disk diffusion and broth micro-well dilution assays showed that B. subtilis was the most resistant strain against both of the EOs and E. coli was the most sensitive bacteria. Results of both disc diffusion and MIC showed that the EO was more effective against A. flavus than A. niger. Antioxidant activity of A. foeniculum by DPPH and ABTS assays revealed remarkable antioxidant activities of this EO comparing with BHT. Results of current study indicated that A. foeniculum EOs can be used as a food preservative in having antibacterial, antifungal and antioxidant activity for the control of food deterioration.
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... It was shown that molecules such as estragole, 1,8-cineole, terpineol-4, and g-terpinene have antifungal activity against Trichophyton erinacei, T. menta grophytes; T. rubrum; T. schoenleinii; and T. soudanense [40,48]. Some research has shown EO from Agastache foeniculum as presenting antifungal, antioxidant [18,41], anticancer [35], or insecticide [42] activities. The rosmarinic acid contained in large quantities in these EOs has been shown to have anticancer properties [6]. ...
... The chemical and antifungal properties of the EO essential oil from Agastache foeniculum were also presented by Kutchin et al. (2017) [5]. It was found that the EO of Lophantus anisatus has high antifungal activity [18]. ...
Comparative Study of Useful Compounds Extracted from Lophanthus anisatus by Green Extraction
Article
Full-text available
Essential oils were obtained from different parts of Agastache foeniculum (Lophanthus anisatus) plants by means of extraction: green extraction using hydro-distillation (HD) and bio-solvent distillation, BiAD, discontinuous distillation, and supercritical fluid extraction, in two stages: (1) with CO2, and (2) with CO2 and ethanol co-solvent. The extraction yields were determined. The yield values varied for different parts of the plant, as well as the method of extraction. Thus, they had the values of 0.62 ± 0.020 and 0.92 ± 0.015 g/100 g for the samples from the whole aerial plant, 0.75 ± 0.008 and 1.06 ± 0.005 g/100 g for the samples of leaves, and 1.22 ± 0.011 and 1.60 ± 0.049 g/100 g for the samples of flowers for HD and BiAD, respectively. The yield values for supercritical fluid extraction were of 0.94 ± 0.010 and 0.32 ± 0.007 g/100 g for the samples of whole aerial plant, 0.9 ± 0.010 and 1.14 ± 0.008 g/100 g for the samples of leaves, and 1.94 ± 0.030 and 0.57 ± 0.003 g/100 g for the samples of flowers, in the first and second stages, respectively. The main components of Lophanthus anisatus were identified as: estragon, limonene, eugenol, chavicol, benzaldehyde, and pentanol. The essential oil from Agatache foeniculum has antimicrobial effects against Staphylococcus aureus, the Escherichia coli and Pseudomonas aeruginosa. Acclimatization of Lophantus anisatus in Romania gives it special qualities by concentrating components such as: estragole over 93%, limonene over 8%, especially in flowers; and chavicol over 14%, estragole over 30%, eugenol and derivatives (methoxy eugenol, methyl eugenol, etc.) over 30% and phenyl ether alcohol over 20% in leaves. As a result of the research carried out, it was proven that Lophanthus anisatus can be used as a medicinal plant for many diseases, it can be used as a spice and preservative for various foods, etc.
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... Therefore, the tendency to use natural compounds, such as EOs, to preserve foodstuffs has been increasing in the last decades and is gaining cumulative interest because of their traditional use in pharmaceutics [98,99]. EOs have shown to exhibit biological antifungal, antibacterial, and antioxidant properties, and have already been applied in a wide range of industries, including the pharmaceutical, agricultural, and food ones [101]. Some studies have been performed in order to establish EOs effects on mycotoxigenic fungi and mycotoxin synthesis, and the results indicated that thyme and oregano EOs have been commonly used against fungi producers of aflatoxins, A. flavus and A. Parasiticus [101,102]. ...
... EOs have shown to exhibit biological antifungal, antibacterial, and antioxidant properties, and have already been applied in a wide range of industries, including the pharmaceutical, agricultural, and food ones [101]. Some studies have been performed in order to establish EOs effects on mycotoxigenic fungi and mycotoxin synthesis, and the results indicated that thyme and oregano EOs have been commonly used against fungi producers of aflatoxins, A. flavus and A. Parasiticus [101,102]. Moreover, cinnamon and cinnamaldehyde have been revealed to present antifungal activity against Aspergillus and Fusarium genera, and significant antimycotoxigenic activity against DON, AFB1, ZEA, and OTA. ...
Mycotoxins Contamination in Rice: Analytical Methods, Occurrence and Detoxification Strategies
Article
Full-text available
  • Sep 2022
The prevalence of mycotoxins in the environment is associated with potential crop contamination, which results in an unavoidable increase in human exposure. Rice, being the second most consumed cereal worldwide, constitutes an important source of potential contamination by mycotoxins. Due to the increasing number of notifications reported, and the occurrence of mycotoxins at levels above the legislated limits, this work intends to compile the most relevant studies and review the main methods used in the detection and quantification of these compounds in rice. The aflatoxins and ochratoxin A are the predominant mycotoxins detected in rice grain and these data reveal the importance of adopting safety storage practices that prevent the growth of producing fungi from the Aspergillus genus along all the rice chain. Immunoaffinity columns (IAC) and QuECHERS are the preferred methods for extraction and purification and HPLC-MS/MS is preferred for quantification purposes. Further investigation is still required to establish the real exposition of these contaminants, as well as the consequences and possible synergistic effects due to the co-occurrence of mycotoxins and also for emergent and masked mycotoxins.
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... Twenty μl EO (stock) with specific concentration and 160 μL nutrient broth (Merck, Darmstadt, Germany) were transferred to each well. Then, 20 μl inoculum was added to each well [36]. The final concentration of bacteria in each microwell was 10 5 CFU/ml (estimated using the surface plate counting method).As a positive control, 20 μl inoculum was added to 180 μl nutrient broth lacking EO (0%). ...
... The plates were incubated at 37 ˚C for 24 h. Bacterial growth was visually determined by turbidity in the wells and the growth in each well was compared with that of the growth control EO free well [36,37]. The minimum concentration of EO that reduced 99.9% of the bacterial population after incubation at 35-37 ˚C for 24 h was considered the MBC [38]. ...
Evaluation of Antibacterial and Antioxidant Activities of Essential Oil of Lime (Citrus aurantifolia) Pomace Powder
Article
Full-text available
The aim of this study was to determine the chemical compounds, antioxidant and antimicrobial activities of Essential Oil (EO) derived from lime pomace. Gas chromatography/mass spectrometry (GC-MS) was used to determine the major components of the obtained EO. The antioxidant activities of this EO were determined by radical scavenging activity (DPPH) and Ferric Reducing Antioxidant Power (FRAP) test. For antimicrobial activity, disk diffusion method was used and the Minimum Inhibitory Concentrations (MIC) and the Minimum Bactericidal Concentration (MBC) were studied against common food borne pathogens including; Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Escherichia coli, Salmonella typhimurium and Pseudomonas aeruginosa. Result showed that the Gram-positive bacteria were more susceptible than gram-negative bacteria.. The result shows that lime pomace powder with IC50 83.061 mg/mL has high antioxidant capacity and also, the chemical analysis of the EO showed that the EO contained a complex mixture of several components and the main constituents were D-limonene (28.86%), α-terpinene (15.65%) and γ-terpinene (12.72%) respectively.
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... This procedure continued up to the well 8. Then, 100 μL inoculum was added to each well (Hashemi et al., 2017). The final concentration of bacteria in each microwell was 10 5 CFU mL −1 . ...
Development of stability, antioxidant, and antimicrobial properties of biopolymeric chitosan- modified starch nanocapsules containing essential oil
Article
Lemon essential oil (LEOs) is used as a bioactive compound with unique health properties as a medicine or dietary supplement. Nevertheless, essential oils are chemical compounds sensitive to light, oxidation, and thermal processes. Therefore, encapsulation technique can be a good way to protect them from degradation and evaporation. In current study, biopolymeric nanocapsules containing lemon essential oils (LEOs) were prepared by the emulsion method. The nanocapsules were characterized by their particle size and Encapsulation efficiency (%) ranged from 339.3 to 553.3 nm and 68.09% to 85.43%, respectively. Long-term storage (30 days) under different temperatures (4°C, 25°C, and 40°C) conditions showed that nanocapsules stored at 4°C were more stable than samples stored at higher temperatures. DPPH and ABTS free radical scavenging activity were measured to evaluate the values of antioxidant activity of LEOs and nanocapsules. The free LEO and nanocapsules were investigated for its antibacterial activity against common Gram-positive and Gram-negative pathogenic microorganisms (Staphylococcus aureus and Escherichia coli) using disk diffusion followed by the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). Our results indicated that the encapsulated LEOs had a significant antioxidant and antibacterial activities, as compared to the free LEO. The LEOs nanocapsules in CS and Hicap can be suggested as an important natural alternative with suitable stability, antioxidant, and antibacterial properties to overcome the challenges associated with the direct application of these bioactive compounds in food.
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... This perspective also increases when recent studies are taken into account, showing that long-term bone administration of 100 mg/kg estragole had no toxic effects in mice, probably because at low exposures they are preferentially detoxicated by biotransformation of ring substituents [53,56]. Anise hyssop EO showed a strong antioxidant capacity and also antimicrobial activity against Staphylococcus aureus, Curtobacterium flaccumfaciens, Listeria monocytogenes, Bacillus subtilis, Salmonella species., Escherichia coli, and Pneumonia vulicans [21]. The EO from A. foeniculum, rich in methyl chavicol, 1,8-cineole, 1-octen-3-ol, 3-octanone, and germacrene D, showed toxicity against two important coleopteran pests (Oryzaephilus surinamensis L. and Lasioderma serricorne F.) of stored-food products [58]. ...
Bridging the Chemical Profile and Biological Activities of a New Variety of Agastache foeniculum (Pursh) Kuntze Extracts and Essential Oil
Article
Full-text available
This study investigated the phytochemical content of alcoholic extracts and essential oil of a new variety of medicinal plants, Agastache foeniculum (Pursh), which Kuntze adapted for cultivation in Romania, namely “Aromat de Buzău”. The essential oil was investigated by GC-MS, while the identification and quantification of various compounds from alcoholic extracts were performed by HPLC-DAD. The total phenol and flavonoid contents of the extracts were evaluated by using standard phytochemical methods. The antioxidant activities of ethanol, methanol extracts, and essential oil of the plant were also assessed against 2,2′-diphenyl-1-picrylhydrazyl (DPPH•), 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS•+), and by ferric reducing power (FRAP) using spectroscopic methods. Cyclic voltammetry was used to evaluate the antioxidant capacity of the essential oil. The concentrations of phenolic compounds were higher in methanolic extract compared to ethanolic extract. A significant correlation was found between total phenol and total flavonoid contents (r = 0.9087). Significant high correlations were also found between the total phenolic compounds and the antioxidant activities of the extracts (r ≥ 0.8600, p < 0.05). In addition, the extracts and essential oil showed good antioxidant and xanthine oxidase inhibitory activities. Estragole was detected as the major constituent of the essential oil (94.89%). The cytotoxic activity of the essential oil was evaluated by the MTT assay. At lower concentrations (1 µg/mL) high cytotoxicity against MCF-7 breast cancer cells was observed but not on the non-tumoral dermal fibroblasts (HDF) which indicated selectivity for cancer cells and suggests the presence of biologically active components that contribute to the observed high cytotoxic effect. Findings from the present study offer new perspectives on the use of A. foeniculum as a potential source of bioactive compounds and a good candidate for pharmaceutical plant-based products.
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... There are apparently five different chemotypes of A. foeniculum based on essential oil chemical profiles: (1) methyl chavicol, (2) spathulenol/bornyl acetate, (3) γcadinene/α-cadinol, (4) limonene, and (5) isomenthone [33,34]. Most A. foeniculum essential oils belong to the methyl chavicol chemotype, however [33,[35][36][37][38][39][40][41][42]. ...
The Volatile Phytochemistry of Seven Native American Aromatic Medicinal Plants
Article
Full-text available
  • May 2021
As part of our evaluation of essential oils derived from Native American medicinal plants, we have obtained the essential oils of Agastache foeniculum (Pursch) Kuntze (Lamiaceae), Gaultheria procumbens L. (Ericaceae), Heliopsis helianthoides (L.) Sweet (Asteraceae), Liatris spicata (L.) Willd. (Asteraceae), Pycnanthemum incanum (L.) Michx. (Lamiaceae), Smallanthus uvedalia (L.) Mack. ex Mack. (Asteraceae), and Verbena hastata L. (Verbenaceae) by hydrodistillation. The essential oils were analyzed by gas chromatographic techniques. The essential oil of A. foeniculum was dominated by estragole (88–93%), while methyl salicylate (91%) dominated the G. procumbens essential oil. Germacrene D was the major component in H. helianthoides (42%) and L. spicata (24%). 1,8-Cineole (31%) and α-terpineol (17%) were the main compounds in P. incanum essential oil. The essential oil of S. uvedalia showed α-pinene (24%), perillene (15%), and β-caryophyllene (17%) as major components. Verbena hastata essential oil was rich in 1-octen-3-ol (up to 29%) and palmitic acid (up to 22%). Four of these essential oils, H. helianthoides, L. spicata, P. incanum, and V. hastata, are reported for the first time. Additionally, the enantiomeric distributions of several terpenoid components have been determined.
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Anti-oxidative and anti-hyperglycemic properties of Agastache foeniculum essential oil and oily fraction in hyperglycemia-stimulated and lipopolysaccharide-stimulated macrophage cells: In vitro and in silico studies
Article
Ethnopharmacological relevance Hyperglycemia (HG) and lipopolysaccharide (LPS) often promote superoxide accumulation, which may increase oxidative stress. Reducing superoxide production in hyperglycemia and the inflammatory condition is an emerging way to reduce protein and lipid oxidation and diabetes complication. Aim of study To examine the effect of Agastache foeniculum essential oil (AFEO) and oil fraction (AFoil) on HG- and LPS-stimulated oxidative stress, the pathogenicity of AFEO and AFoil on oxidative stress was assessed. Methods The stimulatory effects of AFEO and AFoil on the activity and expression of NADH oxide (NOX), catalase (CAT), superoxide dismutase (SOD), and the expression of nuclear respiratory factor 2 (NRF2) and nuclear factor-kappa B (NF-kB) in the stimulated macrophage cell line, J774.A1, was studied. The interaction patterns of AFEO and AFoil components with NOX, SOD, CAT, NRF2, and NF-kB proteins were also deduced using molecular docking. Results Estragole was the main ingredient in AFEO (97%). Linolenic acid (32.10%), estragole (16.22%), palmitic acid (12.62%), linoleic acid (12.04%), and oleic acid (8.73%) were the major chemical components of the AFoil. NOX activation was stimulated in macrophage cells by HG and LPS. At 20 μg/mL, AFEO and AFoil decreased NOX activity while increased SOD and CAT activities in stimulated macrophages. AFoil with estragole and omega-3 fatty acids was better than AFEO with estragole in anti-hyperglycemic and anti-oxidative activity. According to molecular docking research, estragole, linoleic acid, and linolenic acid bind to different hydrophobic pockets of NOX, SOD, CAT, NFR2, and NF-kB using hydrogen bonds, van der Waals bonds, pi-alkyl, and pi-anion interactions, with different binding energies. Conclusion AFEO and AFoil showed antioxidant and anti-diabetic activity. The mechanisms in lowering oxidative stress markers depended on down-regulating superoxide-producing enzymes and up-regulating superoxide-removing enzymes at gene and protein levels. The AFoil emulsion can be used to reduce the detrimental impacts of hyperglycemia and oxidative stress.
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Phytochemical Profiles And Antifitoviral Activities Of Some Medicinal Plant Essential Oils
Conference Paper
Full-text available
  • Jun 2021
Essential oils are fragrant and oily mixtures, mostly consisting of monoterpenoids or sesquiterpenoids, used in medicine, cosmetics and pharmaceutical industry for bactericidal, virucidal, fungicidal, antiparasitic, insecticidal, medicinal ve cosmetic purposes. In addition, they provide aroma and preservation in the food industry. Essential oil composition in plants varies depending on plant organ, environmental factors such as the harvest time, extraction method, ecotype, climate, edaphic factors, altitude and topography, genetic factor and their interaction. Essential oils obtained from plants have many important activities according to their active ingredients. The phenolic components contained in essential oils take an active role in the realization of various reactions in both the plant development process and human metabolism or it acts as a trigger for these reactions to take place. In peppermint essential oil the main components are menthol, menthon, isomentone, 1,8-sineol, 1-5% limonene, while in thyme essential oil are carvacrol, linalol, p-cymene, thymol and ß-caryophylde. Linalool, linalyl acetate, terpinen-4-ol, borneol are dominant in lavender essential oil. The constituents of laurel essential oil are 1,8-sineol, α-terpinyl acetate sabin, α-pinene, β-pinene, terpinen-4-ol, α-terpineol, and medicinal sage components are α- and β- tuion, camphor, sineol and borneol. Essential oil components have been observed to exhibit antiviral activity in humans against a wide variety of viruses such as Hepatitis-A virus, Herpes Simplex Virus type-1 (HSV-1), Herpes Simplex Virus type-2 (HSV-2), influenza A (H1N1), enveloped mumps viruses (MV), immunodeficiency virüs (HIV), rotavirus (RV), yellow fever virus and avian influenza. It has been revealed that studies have been conducted on the antiviral effects of essential oils on plants, mostly against tobacco mosaic virus, cucumber mosaic virus, and vesicular stomatitis viruses. The studies conducted are on the mechanisms of action of essential oils and the treatment of viral infections, and there is no up-to-date and comprehensive information on the interaction between essential oil components and antiviral effects. Therefore, further studies are required on the antiphytoviral activity of essential oils and their constituents, and the essential oil concentrations that should be used.
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