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

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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... Extensive research has been conducted on the chemical composition of anise hyssop essential oil. Studies have consistently identified methyl chavicol as the primary constituent, comprising 88-95% of the oil, contributing to its distinct anise-like smell [5][6][7][8][9][10][11]. However, variations in aromatic compounds, such as menthone or pulegone, can alter the scent profile, sometimes imbuing a minty aroma [1,5,12]. ...
... While anise hyssop is cultivated primarily as an ornamental plant, its cultivation for essential oil production is also significant [3,6]. The essential oil has demonstrated antibacterial [6,9], antioxidant [6,[9][10][11]13,14], and other biological properties [6,10,12,15], adding to its appeal in various industries. ...
... [3], 90% [5], 93.45% [7], 0.10-3.00% [10], 83.1% [11]. This difference in quantities could be explained by the conditions described above. ...
Chemical composition and biological activity of essential oil from anise hyssop
Article
Full-text available
  • May 2024
Anise hyssop (Agastache foeniculum (Pursh) Kuntze) is a perennial plant belonging to the Lamiaceae family mainly used in folk medicine to treat various ailments. This study determined the chemical composition of the essential oil and evaluated its antimicrobial and antioxidant activity. The essential oil was obtained from plants cultivated in the experimental field at the Institute of Roses, Essential and Medical Plants, Kazanlak, Bulgaria. The plants were processed by steam distillation, with the essential oil yielding 0.37%, and its main components being methyl chavicol (82.03%) and limonene (9.90%). The most potent antimicrobial action was observed against the gram-positive bacteria Staphylococcus aureus (25.7 mm inhibition zone) and Bacillus cereus (12.3 mm), the yeast Saccharomyces cerevisiae (16.3 mm) and Candida albicans (16.5 mm). The remaining gram-positive bacteria (Staphylococcus epidermidis and Bacillus subtilis), gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Salmonella ebony), and fungi (Aspergillus brasiliensis and Fusarium moniliforme) were resistant to the action of the essential oil. The antioxidant activity of the essential oil was ABTS (32.36 µmol TE/mL), DPPH (21.61 µmol TE/mL), CUPRAC (19.94 µmol TE/mL), and FRAP (29.56 µmol TE/mL) in vitro. Overall, the results from this study revealed the biological potential of anise hyssop as a source in pharmaceutical, food, and cosmetic applications.
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... The aerial parts of Anise hyssop contain an essential oil (1.4 to 2%) rich in methyl chavicol as a phenylpropanoid metabolite. The essential oil has been found to possess antibacterial and antifungal properties and it is also used in the food, pharmaceutical, cosmetics and beverage industries [17][18][19]. Nanocomposite materials are those materials which amplifying part of them has dimension of one to one hundred nanometers. When nanocomposites are used in food packaging, they will have more ability to withstand the stresses caused by the thermal process of food, transportation, and storage [20]. ...
... Methyl chavicol (89.32%), limonene (7.92%), and sabinene (0.75%) were the most important identified components in AHEO ( Table 2). Similar to the results of this study, Omidbeigi and Sefidkon (2011) and Hashemi et al. (2017) [17,19] also reported methyl chavicol and limonene as the dominant components identified in AHEO cultivated in Iran. Figure 1 shows the three-dimensional curve of the effect of AHEO and BONs on the solubility and moisture content of the PS and GA film. The examination of the graphs indicates that with an increase in the amount of the nanoparticle, solubility also increases. ...
... Methyl chavicol (89.32%), limonene (7.92%), and sabinene (0.75%) were the most important identified components in AHEO ( Table 2). Similar to the results of this study, Omidbeigi and Sefidkon (2011) and Hashemi et al. (2017) [17,19] also reported methyl chavicol and limonene as the dominant components identified in AHEO cultivated in Iran. Figure 1 shows the three-dimensional curve of the effect of AHEO and BONs on the solubility and moisture content of the PS and GA film. The examination of the graphs indicates that with an increase in the amount of the nanoparticle, solubility also increases. ...
Nanocomposite Film of Potato Starch and Gum Arabic Containing Boron Oxide Nanoparticles and Anise Hyssop (Agastache foeniculum) Essential Oil: Investigation of Physicochemical and Antimicrobial Properties
Article
Full-text available
  • Nov 2023
The purpose of this research was to prepare a nanocomposite film of potato starch (PS) and gum arabic (GA) containing boron oxide nanoparticles (BONs) and Anise hyssop (Agastache foeniculum) essential oil (AHEO) and investigate its structural and physicochemical characteristics. For this purpose, BONs in three levels (0, 50 and 100 mg) and AHEO in three levels (0, 100 and 200 µL) were evaluated according to the central compound design. After selecting the optimal films; an experiment to evaluate their antioxidant and antimicrobial activity was conducted. The results revealed that the antioxidant capacity and the films’ thickness increased significantly with the AHEO addition (p < 0.05). The highest antioxidant capacity was 47.62%. The results of Fourier-transform infrared (FT-IR) confirmed the formation of new chemical interactions between PS and GA containing BONs and AHEO. The X-ray diffraction (XRD) results showed that the nanocomposite films had a crystalline structure. The results of thermal analysis revealed that the increase in thermal stability of film samples indicates the proper interaction between the components of nanocomposite films. The increase in the elongation at break point of the films, contrary to their tensile strength, decreased with the increase of BONs and AHEO. Also, the results of the antimicrobial activity of the films revealed that the inhibition zone increased with the increase of BONs and AHEO. The highest inhibition zone (22.47 ± 0.96) was for E. coli. In general, the current research showed promising applications of PS and GA nanocomposite film containing BONs and AHEO for the development of active antimicrobial food packaging.
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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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... While T. gummifera EO has been reported as possessing antibacterial activity [98,99] and was confirmed to be rich in both α-Pinene and β-Pinene (Table 3), which has known antifungal activity [99,100], this activity is strongly dependent on the racemic mixture of its enantiomers, which is dependent on plant origin, among other factors [99,100], thus potentially explaining the results obtained. Thymus mastichina and A. foeniculum were also unable to visibly inhibit fungal growth, despite previous reports of antimicrobial activity against both bacteria and fungi [101,102]. ...
Evaluating the Antifungal Activity of Volatilized Essential Oils on Fungi Contaminating Artifacts from a Museum Collection
Article
Full-text available
  • Feb 2025
As is the case for all forms of cultural heritage, museum collections are under a serious threat of biodeterioration, with fungi playing a significant role in this phenomenon, compromising the preservation and dissemination of past knowledge, artifacts and traditions. As part of the ongoing efforts to study the fungal contaminations observed in the artifacts that compose the collection of the Science Museum of the University of Coimbra, non-invasive sampling of four objects present in the archive was conducted and 43 fungal isolates were retrieved. These isolates were subjected to a comprehensive analysis based on molecular and morphological characteristics and were identified as belonging to 15 different species. Of the 15 isolated species, 5 were selected for in vitro antifungal essential oil assays, based on their relative abundance and biodeteriorative potential. For these, essential oils of Cymbopogon citratus, Lavandula angustifolia, Thapsia gummifera, Mentha pulegium, Mentha suaveolens, Thapsia villosa, Thymus mastichina and Agastache foeniculum were obtained via hydrodistillation, in accordance with the European Pharmacopeia. Of the tested oils, most impacted fungal growth, with Cymbopogon citratus and Lavandula angustifolia being able to fully inhibit the growth of most fungi even at the lowest tested concentrations.
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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
  • May 2023
  • FOOD SCI TECHNOL INT
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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Therapeutic Properties and Use for Medicinal Purposes of Agastache Species
Article
Full-text available
  • Dec 2024
Nowadays, it is proven there is an increasing interest in the study of growth and development of different medicinal and aromatic species, due to their therapeutic properties that correlate with the presence of different active compounds. Agastache sp. are known as aromatic plants that belong to the Lamiaceae family, originating from North America and East Asia. The Agastache genus is part of the Lamiaceae family and is native to North America, but one species like Agastache rugosa, is native to East Asia, such as Korea, Taiwan, Japan, and China. Also, the aim of recent studies is to present a summary of the few findings on the phytochemistry and biological effects of several Agastache sp., including both extracts and essential oil properties and characterization. The presented paper has been focused of introduction, description and use of aromatic and medicinal plants, which represent inexhaustible sources of fresh or dry materials for the pharmaceutical industry, cosmetic products and food industries. In the whole process of developing new medicines from herbal raw materials, it is important to study the spectrum of major bioactive compounds and their benefits for human health. Science have proven a significant influence of genetic traits which depends on the subspecies chosen in study, variety, the maturity of the plants, climatic conditions and cultivation features on the accumulation of bioactive compounds in harvested plants material.
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New coating containing chitosan and Hyssopus officinalis essential oil (emulsion and nanoemulsion) to protect shrimp (Litopenaeus vannamei) against chemical, microbial and sensory changes
Article
  • Jul 2023
In this study, the effect of chitosan coating containing emulsion and nanoemulsion of Hyssopus officinalis essential oil (EO) on the chemical, microbiological and sensory characteristics of shrimp (Litopenaeus vannamei) was investigated. The minimum value of TVB-N (Total volatile basic nitrogen), TBARS (Thiobarbituric acid reactive substances), PV (peroxide value), TMA-N (Trimethylamine-nitrogen) and FFA (Free fatty acids) after 12 days were shown in NE + HEO 1% (coating containing chitosan with nanoemulsion of EO) with 20.53 mg N/100 g, 0.5 µg/kg, 0.88 MAQ peroxide/kg, 1.3 mg/100 g and 12.16 mg 100% of oleic acid, respectively. Also, minimum value of pH after 12 days was related to the CE + HEO 1% (coating containing chitosan with emulsion of EO) with 7.60. The minimum value of psychrophilic and mesophilic microbial count after 12 days were shown in NE + HEO 1%, 4.40 ± 0.36 and 4.03 ± 0.06 cfu/g, respectively. The best score of sensory evaluation was observed in the NE-HEO 1% treatment. As a result, the edible coating containing chitosan-based nanoemulsion could be effective to the preservation of shrimp's microbiological, chemical, and sensory characteristics.
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