Skip to main content
Download PDF

Phytochemical profile and antifungal activity of essential oils obtained from different Mentha longifolia L. accessions growing wild in Iran and Iraq

BMC Plant Biology volume 24, Article number: 461 (2024) Cite this article

A Correction to this article was published on 13 June 2024

This article has been updated

Abstract

Background

Mentha longifolia L. is a perennial plant belonging to the Lamiaceae family that has a wide distribution in the world. M. longifolia has many applications in the food and pharmaceutical industries due to its terpenoid and phenolic compounds. The phytochemical profile and biological activity of plants are affected by their genetics and habitat conditions. In the present study, the content, constituents and antifungal activity of the essential oil extracted from 20 accessions of M. longifolia collected from different regions of Iran and Iraq countries were evaluated.

Results

The essential oil content of the accessions varied between 1.54 ± 0.09% (in the Divandarreh accession) to 5.49 ± 0.12% (in the Khabat accession). Twenty-seven compounds were identified in the essential oils of the studied accessions, which accounted for 85.5-99.61% of the essential oil. The type and amount of dominant compounds in the essential oil were different depending on the accession. Cluster analysis of accessions based on essential oil compounds grouped them into three clusters. The first cluster included Baziyan, Boukan, Sarouchavah, Taghtagh, Darbandikhan, Isiveh and Harir. The second cluster included Khabat, Kounamasi, Soni and Mahabad, and other accessions were included in the third cluster. Significant correlations were observed between the essential oil content and components with the climatic and soil conditions of the habitats. The M. longifolia essential oil indicated antifungal activity against Fusarium solani in both methods used. In all studied accessions, the fumigation method compared to the contact method was more able to control mycelia growth. In both methods, the inhibition percentage of essential oil on mycelia growth increased with an increase in essential oil concentration. Significant correlations were found between the essential oil components and the inhibition percentage of mycelium growth.

Conclusion

The studied M. longifolia accessions showed significant differences in terms of the essential oil content and components. Differences in phytochemical profile of accessions can be due to their genetic or habitat conditions. The distance of the accessions in the cluster was not in accordance with their geographical distance, which indicates the more important role of genetic factors compared to habitat conditions in separating accessions. The antifungal activity of essential oils was strongly influenced by the essential oil quality and concentration, as well as the application method. Determining and introducing the elite accession in this study can be different depending on the breeder’s aims, such as essential oil content, desired chemical composition, or antifungal activity.

Peer Review reports

Introduction

Mentha longifolia L. (horsemint) is a perennial plant belonging to the Lamiaceae family which is distributed in temperate and semi-tropical regions of Europe, west and south of Asia, and north and south of Africa [1]. In the food industry, M. longifolia is used in the form of raw or processed as a spice or preservative [2]. In traditional medicine, this plant is used to treat various diseases such as common cold, cough, sore throat, fever, nausea, nasal congestion, diarrhea, gut spasm, sinusitis, bronchitis, indigestion, intestinal colic, liver disorders and general weakness. Also, this plant is known as a sedative, appetizer, anti-pruritic and insect repellent [3,4,5,6,7,8,9]. Anti-inflammatory [10], antioxidant [11], anti-mutation [12], anti-cancer [13], antibacterial [14], antifungal [11], and antiviral [15] properties of M. longifolia have been proven in previous studies. Phenolic acids, flavonoids and terpenes are the most important effective substances of M. longifolia [8]. Many studies have been conducted on M. longifolia essential oil, the results of which indicate a remarkable diversity in its content and constituents [16,17,18,19,20,21,22,23]. Pathogenic fungi are one of the most destructive microorganisms that cause major damage to agricultural crops before or after harvest [24]. One of the most well-known pathogenic fungi is Fusarium solani. This fungus species has more than 100 hosts among agricultural crops and typically causes crown and root rot in host plants. The infected plants show wilting, stunting, chlorosis, and stem lesions [25]. There are various agricultural, chemical and biological methods to control fungal diseases, but chemical poisons are usually used. The use of chemical poisons to control pathogenic fungi should be limited due to their harmful effects on humans and the environment [26]. The effective compounds of plants, such as essential oils, are a suitable choice to replace chemical poisons due to their high antifungal potential [27]. The antifungal potential of M. longifolia essential oil has been proven in many studies [28,29,30,31,32,33]. The antifungal activity of plant essential oils can vary depending on the type and amount of essential oil constituents [34]. The phytochemical profile of plants is influenced by the genetics and ecological conditions of their habitat. Different accessions belonging to a plant species, due to their different genetics and ecological conditions, have different phytochemical profiles and biological activities. This study aimed to evaluate the phytochemical profile and antifungal activity of essential oils obtained from different M. longifolia accessions collected from Iran and Iraq to identify the superior accession as well as the optimal ecological conditions for the production of essential oil with the desired quantity and quality.

Materials and methods

Identification of M. longifolia habitats, and plant and soil sampling

First, with the help of reliable sources [35] and the information of local people, the habitats of M. longifolia were identified in the northwest and west of Iran, and the east of Iraq (Fig. 1). Then, at the full flowering stage (early July 2021), the habitats were visited, and ten M. longifolia samples were collected from each habitat. The collected plant samples were dried in the shade and prepared for essential oil extraction. A voucher specimen of M. longifolia (HKM2361) identified by Dr. Azad Rastegar has been deposited in the HKS herbarium of Agriculture and Natural Resources Research Center, Sanandaj, Iran. Simultaneously with the plant sampling, one soil sample was prepared from each habitat for physicochemical analysis. The results of soil analysis are shown in Table 1. The geographical coordinates of habitats were obtained by GPS device and Google Earth software. Average monthly temperature and average monthly rainfall of habitats were obtained from the closest weather station to each habitat (Table 1).

Fig. 1
figure 1

Geographical location of the studied M. longifolia accessions

Full size image

Essential oil extraction

The essential oils from plant samples were extracted by Clevenger apparatus based on the hydro distillation method. The essential oil extraction was performed for three hours with three repetitions for each accession. After the essential oil extraction, the volume of the collected essential oil was measured, and its v/w % was calculated. Then, the essential oil was separated from the Clevenger and poured into a glass vial. The obtained essential oils were dehydrated with anhydrous sodium sulfate and kept in the refrigerator at 4 °C until analysis.

Essential oil analysis

GC-MS and GC-FID were used for essential oil analysis. The device’s specifications and their working conditions are given below.

GC-MS: Agilent 7890B/5977A GC/MSD with HP-5 capillary column (30 m length, 0.25 mm inner diameter, 0.25 μm film thickness) was used to identify compounds. The injection chamber temperature was set at 280 °C. The initial temperature of the column was 50 °C for 1 min, and then raised to 260 °C at a rate of 10 °C/min. Helium was used as a carrier gas at a flow rate of 1 mL/min; ionization source temperature, 230 °C; ionization energy, 70 eV; and acquisition mass range, 50–550 m/z. The essential oil components were identified by comparing their calculated Kovats index (KI) with those available in the NIST and Wily databases.

GC-FID: The GC analysis was performed with an Agilent 7890B coupled with a flame ionization detector (FID). The column specifications as well as the thermal program of the column were similar to GC-MS. The injector and detector temperatures were set at 280 and 290 °C, respectively. Similar to GC-MS, helium with a flow rate of 1 mL/min was used as a carrier gas. The quantity of essential oil components was calculated from the GC peak areas using the normalization method.

Table 1 Geographical, climatic and soil characteristics of the studied M. longifolia accessions
Full size table

Antifungal activity

Fungal strain

Fusarium solani (GenBank Acc. No. ON623894) used in the present study was obtained from the University of Kurdistan (Iran) (Fig. 2). Pure culture was transferred into petri dishes (diameter 90 mm) with potato dextrose agar (PDA) and incubated at 24 ± 2 °C for seven days and stored at 4 °C for long-term use.

Fig. 2
figure 2

Morphology of F. solani fungus. a The upper surface of the fungus in the food medium of potato dextrose agar. b the bottom surface of the fungus in the food medium of potato dextrose agar. c Sporodocium on the leaf of clove plant. d and e false head. f conidial cell (monophyalid). g macroconidium. h and i microconidium. j chlamydospore

Full size image

Determination of the fumigation and contact activities of essential oils on mycelia growth

The antifungal activity of essential oils against F. solani was investigated in laboratory conditions using contact and fumigation methods in PDA. In the contact method, different concentrations of essential oils (100, 250, 500, 750 and 1000 ppm) were dissolved in PDA medium containing Tween 80 (0.5% v/v). 15 ml of the obtained solutions were pipetted into plates (9 cm diameter), and the plates were allowed to solidify. A five-day-old disc plug mycelium (5 mm diameter) of F. solani was placed in the center of each plate. PDA without essential oil was used as a control. The plates were incubated at a temperature of 24 ± 2 °C. After ten days, the diameter of F. solani colonies was measured, and the inhibition percentage (I) was calculated using the following formula:

Inhibition (%) = [(dc -dt)]/dc×100.

In the above formula, dc is the radial growth of the pathogen in control; dt is the radial growth of the pathogen in the treatments. In the fumigation method, sterile filter paper discs (diameter 5 mm, Whatman No. 1) were placed for 60 s in different concentrations of essential oils and in the inverted lid of the plates. A mycelium disc plug of the pathogen (5 mm diameter) was taken from the periphery of a 5-day-old culture and placed in the center of the PDA culture medium. Then, the plates were tightly sealed with parafilm to prevent loss of volatile compounds. Plates containing filter paper discs immersed in sterile water were used as controls [36]. Each treatment consisted of four replications in both fumigation and contact methods. All the plates were incubated at 24 ± 2 °C and in dark condition. After 10 days, the diameter of F. solani colonies was measured in different plates, and the percentage of growth inhibition was evaluated. All experiments were performed twice with four replications.

Morphological changes of mycelia in the presence of essential oil

Mycelia of F. solani were treated with M. longifolia essential oil at a concentration of 1000 ppm, based on contact and fumigation methods for seven days. Then, the mycelia were freeze-dried. Morphological changes of mycelia were observed using a scanning electron microscope (SEM) (Zeiss, Germany) at Kermanshah University of Medical Sciences, Kermanshah, Iran.

Statistical analysis

The mean comparison of data (based on Duncan test at probability level 5%) was done using SPSS (ver. 21), two-way cluster analysis of accessions based on essential oil components was carried out using PAST (ver. 4), and heat map correlation between essential oil content and components with climatic and edaphic characteristics, and also essential oil components with inhibition percentage of mycelia growth was obtained using GraphPad Prism (ver. 8).

Results and discussion

Essential oil content and components

A considerable diversity was observed in the viewpoint of essential oil content among the studied M. longifolia accessions. The highest essential oil content (5.49 ± 0.12%) belonged to Khabat accession, followed by Isiveh (5.09 ± 0.3%), and the lowest essential oil content (1.54 ± 0.09%) was obtained from the Divandarreh accession, however, it was not significantly different from the Shaghlavah (1.6 ± 0.13%), Boukan (1.68 ± 0.28%), and Kermanshah (2.05 ± 0.32%) (Fig. 3). In total, 27 compounds were identified in the essential oil of the studied accessions, which accounted for 85.5-99.61% of the essential oil components, depending on the accession. The number of identified compounds was different in the studied accessions. The highest number of identified compounds (25) belonged to Shaghlavah and the lowest of them was obtained for Divandarreh and Taghtagh accessions (17). In all accessions, oxygenated monoterpenes were the dominant class of compounds in the essential oil, and the highest (94.08%) and lowest (58.15%) of these compounds were found in Broujerd and Shaghlavah accessions, respectively. The highest amount of monoterpene hydrocarbons (32.06%), sesquiterpene hydrocarbons (9.2%), and oxygenated sesquiterpenes (0.41%) were obtained from the essential oil of Shaghlavah, Shaghlavah, and Soni accessions, respectively. Oxygenated sesquiterpenes were not found in the essential oil of Harir, Darbandikhan, Taghtagh, Khorramabad, Divandarreh, and Mahabad accessions. The dominant constituents in the essential oils were different, depending on the accession. 1,8-cineole and isopulegyl acetate in Isiveh, Harir, and Darbandikhan; pulegone and isopulegyl acetate in Soni and Mahabad; 1,8-cineole, pulegone, and isopulegyl acetate in Sarouchavah and Khorramabad; pulegone and 1,8-cineole in Kounamasi and Boukan; neo-dihydro carveol acetate, limonene, and α-terpineol in Shaghlavah; pulegone and menthone in Khabat; 1,8-cineole, pulegone, and menthone in Baziyan; pulegone, 1,8-cineole, isopulegyl acetate, and menthone in Taghtagh; pulegone, piperitenone oxide, isopulegyl acetate, and piperitenone in Marivan; piperitenone and piperitenone oxide in Sanandaj; piperitenone oxide, pulegone, and piperitenone in Broujerd; bornyl acetate, piperitenone oxide, and p-menth-3-en-8-ol in Kermanshah; pulegone and piperitenone in Kamyaran; isopulegyl acetate, pulegone, piperitenone oxide, and bornyl acetate in Divandarreh; and pulegone, limonene, and isopulegyl acetate in Saqqez, were the dominant constituents of the essential oil (Table 2).

The essential oil content of M. longifolia in previous studies has been obtained between 1 and 2% [1], 0.87–1.83% [16], 1-2.25% [17], 0.38–4.33% [18], 0.86–2.46% [19], 0.59–1.46% [20], and 1.17–5.5% [21].

Similar to our results, in previous studies, oxygenated monoterpenes have been identified as the main class of compounds in the M. longifolia essential oil, and their amount has varied between 52.28 and 52.7% [18], 52.4-52.85% [1], 56.5-56.89% [20], and 85.76–92.03% [21]. In previous reports, thymol, carvacrol, carvacrol acetate and p-cymene [1], β-ocimene [18], 1,8-cineole [1, 18, 21, 23], menthone [18, 21, 22], menthol [18, 19], pulegone [18, 21,22,23], piperitenone [18, 23], piperitenone oxide [18,19,20,21,22,23], piperitone oxide [18,19,20, 22], trans-dihydrocarvone [19], menthofuran [20], and citronellyl acetate and aromandrene [23] have been reported as the dominant components of M. longifolia essential oil. The variation in the essential oil content and composition of different accessions belonging to a specific plant species can be due to their genetic background or habitat conditions [37]. The production of secondary metabolites in plants is influenced by two factors: the genetic potential of the plant (constitutive production) and external biotic and abiotic stresses (induced production) [38]. Based on the above references, the observed diversity in the phytochemical profile of the studied M. longifolia accessions might be due to the difference in their genetic properties or habitat conditions.

Fig. 3
figure 3

Essential oil content of the studied M. longifolia accessions

Full size image
Table 2 Chemical composition of essential oil in the studied M. longifolia accessions
Full size table

Cluster analysis of M. longifolia accessions based on total essential oil compounds grouped them into three clusters. The first cluster included Baziyan, Boukan, Sarouchavah, Taghtagh, Darbandikhan, Isiveh and Harir. The second cluster included Khabat, Kounamasi, Soni and Mahabad, and other accessions were included in the third cluster. The grouping of accessions in different clusters was not in accordance with their geographical distance, and this result indicates the greater importance of genetic factors compared to habitat conditions in the separation of accessions (Fig. 4).

Fig. 4
figure 4

Two-way cluster analysis of M. longifolia accessions based on their essential oil components

Full size image

Correlation of essential oil content and components with climatic and edaphic characteristics

The essential oil content showed a significant positive correlation with the mean monthly temperature (r = 0.617) and a significant negative correlation with the altitude of the habitat (r= -0.657). Essential oil content had no significant correlation with soil characteristics. Among the essential oil components, α-pinene, β-myrcene, 1,8-cineole, and menthone had significant negative correlations with altitude (r= -0.638, r= -0.447, r= -0.622, and r= -0.487, respectively), while piperitenone oxide, germacrene D, and bicyclogermacrene showed significant positive correlations with altitude (r = 0.598, r = 0.471, and r = 0.487, respectively). Also, α-pinene showed a notable positive correlation with the mean monthly temperature of the habitat (r = 0.535) (Fig. 5).

The other significant correlations were included the positive correlations of p-menth-2-en-1-ol and bornyl acetate with electrical conductivity (r = 0.657 and r = 0.571, respectively), menthone with silt (r = 0.472), α-terpinene and p-cymene with sand (r = 0.453 and r = 0.476, respectively), piperitenone and piperitenone oxide with phosphorus (r = 0.450 and r = 0.544, respectively) and potassium (r = 0.492 and r = 0.630, respectively), and also the negative correlations of caryophyllene oxide with pH (r= -0.446), β-myrcene, α-terpinene, and p-cymene with silt (r= -0.510, r= -0.548, and r= -0.488, respectively), and oxygenated sesquiterpenes with pH (r= -0.446) (Fig. 5).

The optimum temperature for essential oil production in M. longifolia has been reported between 18 and 20 °C [39]. The increase in essential oil production at relatively high temperatures may be due to the increase in photosynthesis and the activity of enzymes responsible for essential oil biosynthesis [40]. Essential oils have a high heat capacity and can prevent damage to the plant in heat stress conditions by storing heat [41]. Negative correlations between altitude and essential oil content have been reported in previous studies conducted on M. longifolia [16, 18, 19], Thymus migricus [42], Thymus kotschyanus [43], and Achillea millefolium L. subsp. millefolium [44]. It seems that the decrease in essential oil production at higher altitudes is due to the decrease in temperature. Low temperatures cause a decrease in nutrient uptake, photosynthesis and carbohydrate production, and subsequently lead to a decrease in secondary metabolites production [45, 46].

The correlation of M. longifolia essential oil components with habitat conditions has been less studied. Afkar et al. [23]. found significant positive correlations between pulegone with annual precipitation and mean annual temperature; piperitenone with soil pH, α-pinene with soil sand content; and significant negative correlations between1,8-cineole with altitude; menthone and α-terpineol with soil clay content.

Fig. 5
figure 5

Heat map correlation between essential oil content and components of the studied M. longifolia accessions with climatic and edaphic characteristics of their habitats

Full size image

Antifungal activity

Scanning electron microscopy analysis

The mycelia morphology of F. solani treated with M. longifolia essential oil at a concentration of 1000 µl/l was observed by SEM. In the control sample, the mycelia were regular, uniform and complete with smooth surfaces, but the mycelia in the samples treated with essential oil showed many morphological changes, including irregular growth, formation of verrucous surface, shrinkage, collapse and hollowing of hyphae (Fig. 6).

Fig. 6
figure 6

Morphological changes of F. solani hyphae. a Control sample. b Treated with essential oil via contact method. c Treated with essential oil via fumigation method

Full size image

Inhibition activity of essential oils on mycelia growth

The results indicated that M. longifolia essential oil inhibited the growth of the fungus mycelia in both contact and fumigation methods (Table 3). In all accessions, the fumigation method compared to the contact method was more able to control mycelia growth. The effect of essential oils on fungus growth is strongly influenced by the method used [47]. Different studies have reported that fumigation method is more effective in controlling the fungus than the contact method [48,49,50]. Monoterpenes are the main class of compounds in M. longifolia essential oil, which have high volatility, and in the fumigation method, they easily convert from liquid to vapor phase, absorbed by the fungus mycelia and finally prevent its growth. But in the contact method, since the essential oil is dissolved in the liquid phase, monoterpenes vaporization and absorption by the fungus mycelia are difficult, and as a result, the fungus continues to grow [51]. In both methods, the inhibition percentage of essential oil on mycelia growth increased with an increase in essential oil concentration. The essential oil concentration is one of the important factors in its effectiveness [52].

The highest inhibition percentage in the fumigation method (100%) belonged to the essential oil of Mahabad, Divandarreh and Kermanshah accessions, while the lowest was seen for Taghtagh, Boukan and Harir (45.28, 48.34 and 48.61%, respectively). In the contact method, the highest inhibition percentage was observed in Broujerd, Kermanshah and Saqez accessions (77.78, 75.84 and 74.17%, respectively), and the lowest was for Darbandikhan and Divandarreh accessions (11.11 and 13.89%, respectively) (Table 3).

Table 3 Inhibition activity (%) of essential oils of M. longifolia accessions on mycelia growth of F. solani after 10 days using two contact and fumigation methods
Full size table

The essential oils of the studied accessions were different in terms of the number, type and amount of their components, which can affect their fungicidal potential. Significant correlations were found between the essential oil components and the inhibition percentage of mycelium growth. In the contact method, a notable negative correlation was obtained between the inhibition percentage with β-myrcene (r= -0.184), α-terpinene (r= -0.203), 1,8-cineole (r= -0.176) and p-menth-2-en-1-ol (r= -0.106). In contrast, the inhibition percentage showed a significant positive correlation with limonene (r = 0.096), p-menth-3-en-8-ol (r = 0.102) and piperitenone oxide (r = 0.167). In the fumigation method, a significant negative correlation was observed between the inhibition percentage with α-pinene (r= -0.091), 1,8-cineole (r= -0.187), γ-terpinene (r= -0.094), menthone (r= -0.100) and caryophyllene oxide (r= -0.126). Also, a significant positive correlation was found between the inhibition percentage with p-menth-2-en-1-ol (r = 0.098), p-menth-3-en-8-ol (r = 0.161), bornyl acetate (r = 0.221), piperitenone oxide (r = 0.149), germacrene D (r = 0.137) and bicyclogermacrene (r = 0.172) (Fig. 7).

Fig. 7
figure 7

Heat map correlation between the inhibition percentage of mycelium growth with essential oil components

Full size image

The effectiveness of essential oils strongly depends on their phytochemical profile [53]. It has been reported that there is a close relationship between the chemical structure of essential oil compounds and the fungicidal activity of essential oil [54]. The most antifungal activity of essential oil components is related to phenolic compounds, followed by aldehydes, ketones, alcohols, ethers, and hydrocarbons [52]. It has been reported that the antifungal activity of M. longifolia essential oil is closely related to the amount of oxygenated monoterpenes [55]. Among the essential oil components that showed significant correlations with the inhibition percentage of mycelium growth, α-pinene, β-myrcene, α-terpinene, limonene, γ-terpinene, germacrene D, and bicyclogermacrene are hydrocarbon compounds; 1,8-cineole and caryophyllene oxide belong to ethereal compounds; p-menth-2-en-1-ol and p-menth-3-en-8-ol are grouped in alcoholic compounds; menthone, bornyl acetate and piperitenone oxide are ketone compounds. It should be noted that the antifungal activity of essential oil is not always dependent on a specific component, and sometimes the synergistic effects of components determine the level of its antifungal activity [56]. Essential oils inhibit the growth of pathogenic fungi by inhibiting the function of fungal mitochondria, preventing cell wall formation, inhibiting efflux pumps, and destroying the cell membrane [57].

The antifungal activity of some essential oil components has been proven in previous studies [58,59,60,61,62,63,64,65,66,67], although the mechanism of their action is not well understood. Bornyl acetate impacts the growth of fungus by affecting enzyme activity, as well as penetrating the lipids of the mitochondrial and cytoplasmic membranes, and as a result, disrupting their structure [58]. Moreover, bornyl acetate affects gene expression and protein activity in different cell types [59]. The antifungal activity of Mentha suaveolens essential oil has been attributed to the high amount of piperitenone oxide [60]. An increase in permeability and damage to the cell membrane, the failure of ion transfer and ATP generation, the disruption of intracellular ion homeostasis, the leakage of intracellular proteins, and the change in cell morphology are some of the limonene effects on pathogenic fungi [61]. The fungicidal potential of germacrene and caryophyllene oxide has also been proven, but the mechanism of their action is not exactly known [62, 63]. In contrast to our results, α-pinene has been shown to have strong antifungal activity [64,65,66,67]. Alpha-pinene damages the cell membrane and affects its conductivity and ion leakage [64]. The antifungal activity of α-pinene may be related to ergosterol binding in the fungal cytoplasmic membrane [65]. It has been proven that α-pinene inhibits the growth of fungal structures such as pseudo-hyphae and blastoconidia [66]. The strong antifungal activity of α-pinene can be related to its inhibitory effect on the activity of phospholipase and esterase enzymes [67]. The inconsistency of our results with previous studies may be due to the synergistic effects of α-pinene and other essential oil compounds of M. longifolia, the type of application method, and the type of fungus studied. Essential oils are a mixture of several compounds, so to determine which component is responsible for the antifungal activity, it is necessary to purify the components and study their effects separately.

Conclusions

The studied M. longifolia accessions showed significant differences in terms of the essential oil content and components. The dominant components of essential oil were different depending on the accessions. The phytochemical profile of accessions was more influenced by genetic than habitat conditions. Significant correlations were found between the essential oil content and components with climate and soil properties of habitat, which can be used for domestication and cultivation of this plant species. M. longifolia essential oil was able to prevent the growth of F. solani fungus, which indicates its strong antifungal activity. The fumigation method was found to be a better method to control the F. solani compared to the contact method. Significant correlations were observed between essential oil components and antifungal activity, which can be useful for producing biological toxins with the desired quality. Determining and introducing the elite accession can be different depending on the aim. If the aim is more essential oil content, Khabat and Isiveh were superior accessions, but if essential oil quality based on some specific compounds is the main goal, the superior accession can be different. The superior accession in the viewpoint of antifungal activity differed depending on the application method and concentration of the essential oil.

Data availability

The datasets used and/or analyzed during the current study are available from the corresponding author on reasonable request.

Change history

References

  1. Patony K, Szalontai H, Radács P, Zámboriné-Németh É. Chemotypes and their stability in Mentha longifolia (L.) L.-A comprehensive study of five accessions. Plants. 2021;10:2478.

    Article  Google Scholar 

  2. Patony K, Zámboriné-Németh É. Horsemint as a potential raw material for the food industry: survey on the chemistry of a less studied mint species. Phytochemistry Rev. 2021;20:631–52.

    Article  Google Scholar 

  3. Naghibi F, Mosaddegh M, Mohammadi Motamed S, Ghorbani A. Labiatae family in folk medicine in Iran: from ethnobotany to pharmacology. Iran J Pharmaceut Res. 2009;4(2):63–79.

    Google Scholar 

  4. Kozan E, Kupeli E, Yesilada E. Evaluation of some plants used in Turkish folk medicine against parasitic infections for their in vivo anthelmintic activity. J Ethnopharmacol. 2006;108(2):211–6.

    Article  PubMed  Google Scholar 

  5. Darwish RM, Aburjai TA. Effect of ethnomedicinal plants used in folklore medicine in Jordan as antibiotic resistant inhibitors on Escherichia coli. BMC Compl Altern Med. 2010;10:9.

    Article  Google Scholar 

  6. Al-Bayati FA. Isolation and identification of antimicrobial compound from Mentha longifolia L. leaves grown wild in Iraq. Annal Clin Microb Antimicrob. 2009;8:20.

    Article  Google Scholar 

  7. Eissa TAF, Palomino OM, Carretero ME, Gómez-Serranillo S. Ethnopharmacological study of medicinal plants used in the treatment of CNS disorders in Sinai Peninsula, Egypt. J Ethnopharmacol. 2014;151(1):317–32.

    Article  CAS  PubMed  Google Scholar 

  8. Farzaei MH, Bahramsoltani R, Ghobadi A, Farzaei F, Najafi F. Pharmacological activity of Mentha longifolia and its phytoconstituents. J Tradit Chin Med. 2017;37(5):710–20.

    Article  Google Scholar 

  9. Khani A, Asghari J. Insecticide activity of essential oils of Mentha longifolia, Pulicaria gnaphalodes and Achillea wilhelmsii against two stored product pests, the flour beetle, Tribolium castaneum, and the cowpea weevil, Callosobruchus maculatus. J Insect Sci. 2012;12(73):1–10.

    Article  Google Scholar 

  10. Karimian P, Kavoosi GR, Amirghofran Z. Anti-inflammatory effect of Mentha longifolia in lipopolysaccharide stimulated macrophages: reduction of nitric oxide production through inhibition of inducible nitric oxide synthase. J Immunot. 2013;10(4):393–400.

    Article  CAS  Google Scholar 

  11. Gulluce M, Sahin F, Sokmen M, Ozer H, Daferera D, Sokmen A, Polissiou M, Adiguzel A, Ozkan H. Antimicrobial and antioxidant properties of the essential oils and methanol extract from Mentha longifolia L. ssp. Longifolia. Food Chem. 2007;103(4):1449–56.

    Article  CAS  Google Scholar 

  12. Orhan F, Gulluce M, Ozkan H, Alpsoy L. Determination of the antigenotoxic potencies of some luteolin derivatives by using a eukaryotic cell system, Saccharomyces cerevisiae. Food Chem. 2012;141(1):366–72.

    Article  Google Scholar 

  13. Patti F, Palmioli A, Vitalini S, Bertazza L, Redaelli M, Zorzan M, Rubin B, Mian C, Bertolini C, Iacobone M, Armanini D, Barollo S, Airoldi C, Iriti M, Pezzani R. Anticancer effects of wild mountain Mentha longifolia extract in adrenocortical tumor cell models. Front Pharmacol. 2020;10:1647.

    Article  PubMed  PubMed Central  Google Scholar 

  14. Elansary HO, Szopa A, Kubica P, Ekiert H, Klimek-Szczykutowicz M, El-Ansary DO, Mahmoud EA. Polyphenol profile and antimicrobial and cytotoxic activities of natural Mentha×piperita and Mentha longifolia populations in northern Saudi Arabia. Process. 2020;8:479.

  15. Amzazi S, Ghoulami S, Bakri Y, Il Idrissi A, Fkih-Tétouani S, Benjouad A. Human immunodeficiency virus type 1 inhibitory activity of Mentha longifolia. Therapie. 2003;58(6):531–4.

    Article  PubMed  Google Scholar 

  16. Hosseini Z, Feizi H, Vatandoost Jertoodeh S, Alipanah M. Evaluation of ecological and morphological traits and essential oil productivity of Mentha longifolia L. in Fars and Khorasan Razavi provinces. J Agroecol. 2019;11(1):335–47.

    Google Scholar 

  17. Noroozi V, Yousefzadeh S, Asilan KS, Mansourifar S. Investigating the variation of essential oil content, chlorophyll, carotenoid, anthocyanin and flavonoid of Mentha longifolia (L.) Hods. subsp. longifolia in several habitats of Marand. Eco-phytochem J Med Plant. 2017;5(1):52–66.

    Google Scholar 

  18. Moshrefi Araghi A, Nemati H, Azizi M, Moshtaghi N, Shoor M, Hadian J. Assessment of phytochemical and agro-morphological variability among different wild accessions of Mentha longifolia L. cultivated in field condition. Ind Crop Prod. 2019;140:111698.

    Article  CAS  Google Scholar 

  19. Aksit H, Demirtas I, Telci I, Tarimcilar G. Chemical diversity in essential oil composition of Mentha longifolia (L.) Hudson subsp. typhoides (Briq.) Harley var. typhoides from Turkey. J Essent Oil Res. 2013;25(5):430–7.

    Article  CAS  Google Scholar 

  20. Viljoen AM, Petkar S, van Vuuren SF, Cristina Figueiredo A, Pedro LG, Barroso JG. The chemo-geographical variation in essential oil composition and the antimicrobial properties of wild mint Mentha longifolia subsp. polyadena (Lamiaceae) in Southern Africa. J Essent Oil Res. 2006;18(1):60–5.

    Article  CAS  Google Scholar 

  21. Azarkish P, Moghaddam M, Vaezi J, Ghasemi Pirbalouti A, Davarinejad G. Chemical composition essential oil of hors mint (Mentha longifolia) as a rich source of pulegone from five wild habitats of Fars province. Plant Prod. 2017;39(4):87–100.

    Google Scholar 

  22. Segev D, Nitzan N, Chaimovitsh D, Eshel A, Dudai N. Chemical and morphological diversity in wild populations of Mentha longifolia in Israel. Chem Biodiver. 2012;9(3):577–88.

    Article  CAS  Google Scholar 

  23. Afkar S, Azadpour M, Mahdavi B, Rashidipour M. Evaluation of essential oil composition and antibacterial effect of Mentha longifolia collected from different region of Lorestan Province. Iran J Hort Sci. 2021;51(4):823–35.

    Google Scholar 

  24. Peng Y, Li SJ, Yan J, Tang Y, Cheng JP, Gao AJ, Yao X, Ruan JJ, Xu BL. Research progress on phytopathogenic fungi and their role as biocontrol agents. Front Microbiol. 2021;12:670135.

    Article  PubMed  PubMed Central  Google Scholar 

  25. Homa M, Galgóczy L, Manikandan P, Narendran V, Sinka R, Csernetics Á, Vágvölgyi C, Kredics L, Papp T. South Indian isolates of the Fusarium solani species complex from clinical and environmental samples: identification, antifungal susceptibilities, and virulence. Front Microbiol. 2018;23(9):1052.

    Article  Google Scholar 

  26. Sofalian O, Rahimi Y, Hasanian S, Zare N, Davari M, Jamshidi M. Studying antifungal effect of pennyroyal against plant pathogenic fungi. J Med Plant Biotechnol. 2018;4(1):70–9.

    Google Scholar 

  27. Plotto A, Roberts RG, Roberts DD. Evaluation of plant essential oils as natural postharvest disease control of tomato (Lycopersicun Esculentum). Acta Hort. 2003;628:737–45.

    Article  CAS  Google Scholar 

  28. Movaghari Pour A, Sheikh Fathollahi M, Poor Zamani M, Abedian S, Jamali Z. Comparison of anti-fungal effect of Origanum vulgare extract versus nystatin on Candida albicans; an in vitro study. J Mashhad Dent School. 2018;42(3):271–7.

    Google Scholar 

  29. Asghari Marjanlo A, Mostofi Y, Heydari M, Javan Nik Khah M, Shoeibi S. Antifungal effects of four plant essential oils on Botrytis Cinerea in laboratory conditions. J Med Plant. 2011;10(39):14–24.

    Google Scholar 

  30. Ali HM, Elgat WAAA, El-Hefny M, Salem MZM, Taha AS, Al Farraj DA, Elshikh MS, Hatamleh AA, Abdel-Salam EM. New approach for using of Mentha longifolia L. and Citrus reticulata L. essential oils as wood-biofungicides: GC-MS, SEM, and MNDO quantum chemical studies. Material. 2021;14:1361.

    Article  CAS  Google Scholar 

  31. Dehghanpour-Farashah S, Taheri P. Antifungal and antiaflatoxigenic effects of Mentha longifolia essential oil against aspergillus flavus. Int J New Technol Res. 2016;2(9):30–9.

    Google Scholar 

  32. Behnamian M, Najafi Z, Davari M, Dezhsetan S. Antifungal activity of medicinal plant essential oils against mycogone perniciosa, causal agent of wet bubble and their effects on button mushroom. Biol Control Pest Plant Disease. 2017;6(1):111–9.

    Google Scholar 

  33. Desam NR, Al-Rajab AJ, Sharma M, Mylabathula MM, Gowkanapalli RR, Mohammed A. Chemical composition, antibacterial and antifungal activities of Saudi Arabian Mentha longifolia L. essential oil. J Coastal Life Med. 2017;5(10):441–6.

    Article  CAS  Google Scholar 

  34. Fernández-Sestelo M, Carillo JM. Environmental effects on yield and composition of essential oil in wild populations of spike lavender (Lavandula latifolia Medik). Agriculture. 2020;10(12):626–43.

    Article  Google Scholar 

  35. Rechinger KH. Flora Iranica. Graz: Akademische Druck; 2005.

    Google Scholar 

  36. Thomidis T, Filotheou A. Evaluation of five essential oils as bio-fungicides on the control of Pilidiella granati rot in pomegranate. Crop Protect. 2016;89:66–71.

    Article  CAS  Google Scholar 

  37. Khorshidi J, Morshedloo MR, Moradi S. Essential oil composition of three Iranian Hypericum species collected from different habitat conditions. Biocatal Agr Biotechnol. 2020;28:101755.

    Article  Google Scholar 

  38. Ghassemi-Golezani K, Farhadi N. Physiology of medicinal plants. Tabriz: University of Tabriz; 2019.

    Google Scholar 

  39. Omidbaigi R. Production and processing of medicinal plants. Mashhad: Behnashr; 2013.

    Google Scholar 

  40. Eisapoor M, Hemmati Kh, Hemmati N. Study of the effect of habitat on morphological and phytochemical traits of horsemint (Mentha longifolia L). J Hort Sci. 2020;33(4):698–710.

    Google Scholar 

  41. Fasina OO, Colley Z. Viscosity and specific heat of vegetable oils as a function of temperature: 35°c to 180°c. Int J Food Proper. 2008;11:738–46.

    Article  Google Scholar 

  42. Yavari AR, Nazeri V, Sefidkon F, Hassani ME. Evaluation of some ecological factors, morphological traits and essential oil productivity of Thymus migricus Klokov & Desj. Shost. Iran J Med Arom Plant Res. 2010;26:227–38.

    Google Scholar 

  43. Habibi H, Mazaheri D, Majnoon Hosseini N, Chaeechi MR, Fakhr-Tabatabaee M, Bigdeli M. Effect of altitude on essential oil and components in wild thyme (Thymus kotschyanus Boiss) Taleghan region. Pajouhesh Sazandegi. 2006;73:2–10.

    Google Scholar 

  44. Azarnivand H, Ghavam Arabani M, Sefidkon F, Tavili A. The effect of ecological characteristics on quality and quantity of the essential oils of Achillea millefolium L. subsp. millefolium. Iran J Med Arom Plant Res. 2010;25(4):556–71.

    Google Scholar 

  45. Shirzadi N, Nasr Esfahani M, Hajihashemi S. The identification of physiological and biochemical changes in leave and shoot of stevia under low temperature. J Plant Res. 2021;34(2):327–40.

    Google Scholar 

  46. Khorshidi J, Shokrpour M, Nazeri V. Influence of some climatic and soil conditions on essential oil quantity and quality of different Thymus daenensis Celak subsp. daenensis ecotypes. Iran J Hort Sci. 2019;50(1):13–23.

    Google Scholar 

  47. Anthony S, Abeywickrama K, Dayananda R, Wijeratnam SW, Arambewela L. Fungal pathogens associated with banana fruit in Sri Lanka and their treatment with essential oils. Mycopathologia. 2004;157:91–7.

    Article  PubMed  Google Scholar 

  48. Feng W, Chen J, Zheng X, Liu Q. Thyme oil to control Alternaria alternata in vitro and in vivo as fumigant and contact treatments. Food Contr. 2011;22(1):78–81.

    Article  CAS  Google Scholar 

  49. Sukcharoen O, Sirirote P, Thanaboripat D. Control of aflatoxigenic strains by Cinnamomum Porrectum essential oil. J Food Sci Tech. 2017;54(9):2929–35.

    Article  CAS  Google Scholar 

  50. Wang D, Zhang J, Jia X, Xin L, Zhai H. Antifungal effects and potential mechanism of essential oils on Collelotrichum gloeosporioides in vitro and in vivo. Molecule. 2019;24(18):3386.

    Article  CAS  Google Scholar 

  51. Inouye S, Abe S, Yamaguchi H, Asakura M. Comparative study of antimicrobial and cytotoxic effects of selected essential oils by gaseous and solution contacts. Int J Aromather. 2003;13:33–41.

    Article  Google Scholar 

  52. Kalemba D, Kunicka A. Antibacterial and antifungal properties of essential oils. Curr Med Chem. 2003;10:813–29.

    Article  CAS  PubMed  Google Scholar 

  53. Vesaltalab Z, Gholami M. The effect of clove buds and rosemary extracts and essences on control of Botrytis Cinerea growth. Plant Prod Technol. 2012;3(2):1–11.

    Google Scholar 

  54. Ozcan M, Boyraz N. Antifungal properties of some herb decoctions. Eur Food Res Technol. 2000;212:86–8.

    Article  CAS  Google Scholar 

  55. Mimica Dukić N, Bozin B, Soković M, Mihailović B, Matavulj M. Antimicrobial and antioxidant activities of three Mentha species essential oils. Planta Med. 2003;69(5):413–9.

    Article  PubMed  Google Scholar 

  56. Adegoke GO, Iwahashi H, Komatsu Y, Obuchi K, Iwahashi Y. Inhibition of food spoilage yeasts and aflatoxigenic moulds by monoterpenes of the spice Aframomum danielli. Flavour Fragr J. 2000;15:147–50.

    Article  CAS  Google Scholar 

  57. Nazzaro F, Fratianni F, Coppola R, Feo V. Essential oils and antifungal activity. Pharmaceutical. 2017;10(4):86.

    Google Scholar 

  58. Jaradat N. Phytochemical profile and in vitro antioxidant, antimicrobial, vital physiological enzymes inhibitory and cytotoxic effects of Artemisia Jordanica leaves essential oil from Palestine. Molecule. 2021;26:2831.

    Article  CAS  Google Scholar 

  59. Yang H, Zhao R, Chen H, Jia P, Bao L, Tang H. Bornyl acetate has an anti-inflammatory effect in human chondrocytes via induction of IL-11. IUBMB Life. 2014;66(12):854–9.

    Article  CAS  PubMed  Google Scholar 

  60. Oumzil H, Ghoulami S, Rhajaoui M, Ilidrissi A, Fkih-Tetouani S, Faid M, Benjouad A. Antibacterial and antifungal activity of essential oils of Mentha suaveolens. Phytother Res. 2002;16:727–31.

    Article  CAS  PubMed  Google Scholar 

  61. Cai R, Hu M, Zhang Y, Niu C, Yue T, Yuan Y, Wang Z. Antifungal activity and mechanism of citral, limonene and eugenol against Zygosaccharomyces rouxii. LWT. 2019;106:50–6.

    Article  CAS  Google Scholar 

  62. Badalamenti N, Bruno M, Formisano C, Rigano D. Effect of germacrene-rich essential oil of Parentucellia latifolia (L.) caruel collected in central Sicily on the growth of microorganisms inhabiting historical textiles. Nat Prod Commun. 2022;17(4):1–6.

    Google Scholar 

  63. Yang D, Michel L, Chaumont JP, Millet-Clerc J. Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis. Mycopathologia. 1999;148(2):79–82.

    Article  CAS  PubMed  Google Scholar 

  64. Lüleci HB, Ergüden B. Investigation of antifungal activity mechanisms of alphapinene, eugenol, and limonene. J Adv VetBio Sci Tech. 2022;7(3):385–90.

    Article  Google Scholar 

  65. de Bomfim D, de Oliveira E, Lima L, Alves da Silva L, Cavalcante Fonseca M, Ferreira RC, Diniz Neto H, da Nóbrega Alves D, da Silva Rocha WP, Scotti L, de Oliveira Lima E, Vieira Sobral M, Cançado Castellano LR, Moura-Mendes J. Queiroga Sarmento Guerra F, Da Silva MV. α-Pinene: Docking study, cytotoxicity, mechanism of action, and anti-biofilm effect against Candida albicans. Antibiotic. 2023;12(3):480.

    Article  Google Scholar 

  66. Nóbrega JR, Silva DF, Andrade Júnior FP, Sousa PMS, Figueiredo PTR, Cordeiro LV, Lima EO. Antifungal action of α-pinene against Candida spp. isolated from patients with otomycosis and effects of its association with boric acid. Nat Prod Res. 2021;35(24):6190–93.

    Article  PubMed  Google Scholar 

  67. Rivas da Silva AC, Lopes PM, Barros de Azevedo MM, Costa DC, Alviano CS, Alviano DS. Biological activities of α-pinene and β-pinene enantiomers. Molecule. 2012;17(6):6305–16.

    Article  Google Scholar 

Download references

Funding

Not applicable.

Author information

Authors and Affiliations

  1. Department of Horticultural Science and Engineering, Faculty of Agriculture, University of Kurdistan, Sanandaj, 66177-15175, Iran

    Kosrat Hama Mustafa, Jalal Khorshidi & Yavar Vafaee

  2. Department of Horticulture, College of Agricultural Engineering Sciences, University of Raparin, Ranya, Iraq

    Kosrat Hama Mustafa

  3. Research Center of Medicinal Plants Breeding and Development, University of Kurdistan, Sanandaj, Iran

    Jalal Khorshidi & Yavar Vafaee

  4. Forests and Rangelands Research Department, Kurdistan Agricultural and Natural Resources Research and Education Center, Sanandaj, Iran

    Azad Rastegar

  5. Department of Horticultural Science and Engineering, Faculty of Agriculture, University of Maragheh, Maragheh, Iran

    Mohammad Reza Morshedloo

  6. Department of Plant Protection, Faculty of Agriculture, University of Kurdistan, Sanandaj, 66177-15175, Iran

    Somaieh Hossaini

Authors
  1. Kosrat Hama Mustafa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jalal Khorshidi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yavar Vafaee
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Azad Rastegar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mohammad Reza Morshedloo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Somaieh Hossaini
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

KHM and SH performed the experiments; JK and YV designed and supervised the research, analyzed data and wrote the original draft; AR and MRM were project advisors. The all authors read and approved the final manuscript.

Corresponding authors

Correspondence to Jalal Khorshidi or Yavar Vafaee.

Ethics declarations

Ethics approval and consent to participate

We state that the methods used throughout the experiment were conducted in accordance with relevant guidelines and regulations.

Consent for publication

Not applicable.

Competing interests

The authors declare no competing interests.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

The original online version of this article was revised: the authors identified errors in Table 2.

Rights and permissions

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mustafa, K.H., Khorshidi, J., Vafaee, Y. et al. Phytochemical profile and antifungal activity of essential oils obtained from different Mentha longifolia L. accessions growing wild in Iran and Iraq. BMC Plant Biol 24, 461 (2024). https://doi.org/10.1186/s12870-024-05135-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1186/s12870-024-05135-z

Keywords

BMC Plant Biology

ISSN: 1471-2229

Contact us