Acta agriculturae Slovenica, 117/2, 1–11, Ljubljana 2021 doi:10.14720/aas.2021.117.2.1335 Original research article / izvirni znanstveni članek Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cuminum cyminum L. populations Amir SOLTANBEIGI 1, 2 , Harun DIRAMAN 3 and Mohammad Bagher HASSANPOURAGHDAM 4 Received November 16, 2019; accepted March 18, 2021. Delo je prispelo 16. novembra 2019, sprejeto 18. marca 2021. 1 PhD., Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Afyonkarahisar Health Sciences University, Afyonkarahisar, Turkey. 2 Corresponding author: amir.soltanbeigi@afsu.edu.tr / https://orcid.org/0000-0002-8791-0482 3 Ph.D., Afyon Kocatepe University, Faculty of Engineering, Food Engineering Department, Afyonkarahisar, Turkey. https://orcid.org/0000-0002-7431-7524 4 Ph.D., University of Maragheh, Faculty of Agriculture, Department of Horticulture Science, Iran. https://orcid.org/0000-0001-7130-2426 Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cumi- num cyminum L. populations Abstract:Volatile oil and fatty acids components of six various populations of wild Bunium persicum Boiss. (Bam and Zirkuh/Iran) and cultivated Cuminum cyminum L. (Rayen/ Iran; Cukurcak, Taskopru and Asagialicomak/Turkey) species were investigated. The volatile oil content of Bam and Zirkuh populations were 3.9 and 4.7 %, respectively. The analysis of volatile oils by the GC/FID-MSD showed that γ-terpinene (33.62-39.62 %), cuminal (17.9-19.3 %), o-cymene (5.3-11.1 %), benzenemethanol, α-methyl- (7.4-9.5 %), 1-phenyl-1-bu- tanol (6.4-8.4 %) and limonene (6.4-8.6 %) were the major components of B. persicum populations. Rayen, Cukurcak, Tas- kopru and Asagialicomak populations of C. cyminum had 2.6, 2.2, 2.0 and 2.5 % of volatile oil, respectively. Cuminal (22.8- 37.6 %), benzenemethanol, α-methyl- (5.3-22.6 %), γ-terpinene (16.7-19.4 %), β-pinene (11.2-11.9 %) and 1-phenyl-1-butanol (5.4-12.5 %) were identified as the main components of C. cyminum. Fatty acids were detected by the GC/FID. In total, 15 fatty acids were characterised in B. persicum populations from Iran. Petroselinic acid (26.3-52.6 %), lauric acid (16.2-37.0 %) and linoleic acid (18.3-33.0 %) were the predominant fatty ac- ids identified in Iranian populations. C. cyminum populations were rich in the same fatty acids but, the order was: petroselinic acid (47.5-55.5 %), linoleic acid (22.5-25.4 %) and lauric acid (13.4-24.2 %). Monounsaturated fatty acids (27.4-56.2 %) were the major subgroup. Overall, B. persicum populations from Iran and C. cyminum from Turkey were almost similar in fatty acids profile although they had wide diversity in the volatile oils com- positional profile. Key words: Bunium persicum; Cuminum cyminum; essen- tial oil; fatty acid; GC Kemijska sestava hlapnih olj in maščobnih kislin samoniklih populacij črne gomoljaste kumine (Bunium persicum (Boiss.) B. Fedtsch.) in gojenih populacij rimske kumine (Cuminum cyminum L.) Izvleček: Preučena je bila sestava hlapnih olj in maščobnih kislin dveh samoniklih populacij črne gomoljaste kumine (Bu- nium persicum Boiss.) (Bam and Zirkuh/Iran) in štirih popu- lacij gojene rimske kumine (Cuminum cyminum L.); (Rayen/ Iran; Cukurcak, Taskopru and Asagialicomak/Turčija). Vseb- nost hlapnih olj je v populacijah Bam in Zirkuh znašala 3,9 in 4,7 %. Analiza hlapnih olj z GC/FID-MSD je pokazala, da so bile v populacijah črne gomoljaste kumine njihove glavne sestavine γ-terpinen (33,62-39,62 %), kuminal (17,9-19,3 %), o-cimen (5,3-11,1 %), benzenmetanol, α-metil- (7,4-9,5 %), 1-fenil-1-butanol (6,4-8,4 %) in limonen (6,4-8,6 %). Popu- lacije rimske kumine iz rastišč Rayen, Cukurcak, Taskopru in Asagialicomak so vsebovale 2,6; 2,2; 2,0 in 2,5 % hlapnih olj. Kuminal (22,8-37,6 %), benzenmetanol, α-methyl- (5,3-22,6 %), γ-terpinen (16,7-19,4 %), β-pinen (11,2-11,9 %) in 1-fenil- 1-butanol (5,4-12,5 %) so bile glavne sestavine hlapnih olj v rimski kumini. Maščobne kisline so bile analizirane z GC/FID. Celokupno je bilo v populacijah črne gomoljaste kumine iz Ira- na določenih 15 maščobnih kislin, pri čemer so imele največji delež petršilova (26,3-52,6 %), lovorjeva (16,2-37,0 %) in lin- olenska kislina (18,3-33,0 %). Populacije rimske kumine so vsebovale enake maščobne kisline, a njihov delež je bil sledeč: petršilova (47,5-55,5 %), linolenska (22,5-25,4 %) in lovorjeva kislina (13,4-24,2 %). Enkrat nenasičene maščobne kisline so bile glavna podskupina (27,4-56,2 %). Nasplošno so imele pop- ulacije črne gomoljaste kumine iz Irana in rimske kumine iz Turčije podobno sestavo maščobnih kislin a veliko različnost v sestavi hlapnih olj Ključne besede: Bunium persicum; Cuminum cyminum; eterična polja; maščobne kisline; plinska kromatografija (GC) Acta agriculturae Slovenica, 117/2 – 2021 2 A. SOLTANBEIGI et al. 1 INTRODUCTION Bunium persicum (Boiss.) B. Fedtsch. [syn: Elwen- dia persica (Boiss.) Pimenov & Kljuykov] as a member of the Apiaceae family is a perennial and herbaceous plant that grows in a limited area of Central to West Asia. The fruits (seeds) of B. persicum have been widely used as medicinal, aromatic and spice plants in food and cos- metic industries (Azizi et al., 2009; Omidbeigi, 2013). The active ingredients of this plant are volatile oils ex- tracted from the ripe fruits (Kan et al., 2007). Based on numerous studies, B. persicum has biological and phar- macological properties including antimicrobial (Rustaie et al., 2016), antioxidant (Sharafati Chaleshtori, 2018), antifungal (Takayuki et al., 2007; Khaledi and Hassani, 2018), antibacterial (Demirci et al., 2008; Oroojalian et al., 2010), hypoglycaemic and anti-inflammatory activi- ties (Hajhashemi, 2011). The B. persicum fruit samples from different locations of Kerman province/Iran con- tained 3.5, 4, 7 and 8.5 % of volatile oil (Omidbaigi and Arvin, 2009). ρ-cuminaldehyde (23.50 %), α-methyl- benzenemethanol (14.59 %), γ-terpinene (13.10 %) and β-cymene (8.48 %), sabinene (5.82 %) and α-pinene (4.03 %) were reported as major constituents of B. persicum es- sential oil (Sanei Dehkordi et al., 2016). Cuminum cyminum L. is a valuable medicinal and aromatic plant that originated from Egypt, Central Asia and Eastern Mediterranean regions (Omidbeigi, 2013). The fruits of C. cyminum are applied as a popular spice in the kitchen and food industries (Hajlaoui et al., 2010). This plant possesses anti-inflammatory, diuretic, carmi- native and antispasmodic characteristics. It is also used to treat toothache, epilepsy, dyspepsia, jaundice, diarrhea, flatulence, and indigestion (Evanse et al., 1996; Dhanda- pani et al., 2002; Rebey et al., 2012). Also, C. cyminum has high antioxidant and antibacterial activities (Guo et al., 2018). The volatile oil content of this plant has been reported from 1 to 5 % (Lee, 2005; Ladan Moghadam, 2016). The main components of the volatile oil are mono- terpenes and sesquiterpene derivatives such as cuminal (36.31 %), cuminic alcohol (16.92 %), γ-terpinene (11.14 %), safranal (10.87 %), p-cymene (9.85 %) and β-pinene (7.75 %) (Li and Jiang, 2004). Another valuable by-product of the Apiaceae family is their fatty oil which is widely used in various industries (Kooti et al., 2015). Petroselinic acid is the major compo- nent of C. cyminum fatty oil (Dubey et al., 2018). Also, petroselinic acid, oleic acid, linoleic acid, lauric acid and palmitic acid were introduced as the main components of B. persicum fatty oil (Khalid et al., 2009). Although comprehensive information on cumin oil is available in the literatures, there are a few available scientific records about B. persicum. The production and accumulation of secondary metabolites and their qualities are affected by various biotic and abiotic factors such as genetic char- acteristics, climatic conditions (light, temperature, rain- fall, irrigation, soil, height, location, etc.), environment organisms, applied agro-techniques and post-production processing (Soltanbeigi & Sakartepe, 2020). The aim of this investigation was the comparison of volatile oil content and the volatile and fatty oils chemi- cal component and its diversity in various populations of B. persicum and C. cyminum from different locations of Iran and Turkey. 2 MATERIALS AND METHODS 2.1 PLANT MATERIALS The fruits of two populations of wild Bunium per- sicum were collected from the mountains of Bam (Ker- man Province/Iran) and Zirkuh (Khorasan Province/ Iran). Also, four cultivated Cuminum cyminum fruits samples were obtained from Rayen county (Kerman Province/Iran), Cukurcak (Çukurcak/Sultandağı), Taskopru (Taşköprü/Sultandağı) and Asagialicomak (Aşağıaliçomak/Emirdağ) villages (Afyonkarahisar/Tur- key). The geographical and climatic conditions of the sampling regions are outlined in Table 1. The plants were taxonomically identified by a senior expert from the Ag- ricultural Research, Education and Extension Organiza- tion of West Azerbaijan Province of Iran and Afyonkara- hisar Directorate of Provincial Agriculture and Forestry, Republic of Turkey. 2.2 ISOLATION OF VOLATILE OILS 50 g of powdered dried fruits of plant samples were subjected to hydro-distillation by using a Clevenger type apparatus for 3 hours and volatile oil content of the sam- ples was calculated as: Oil content (v/M) = observed volume of oil (ml)/ mass of sample (g) × 100 The volatile oil samples were dried over anhydrous sodium sulfate and were stored at 4 °C in ambered vials till GC-MS analysis. 2.3 DETERMINATION OF VOLATILE OIL COM- PONENTS A gas chromatography (GC) system (Agilent Technologies, 7890B) equipped with a flame ioniza- tion detector (FID) and coupled to a mass spectrom- Acta agriculturae Slovenica, 117/2 – 2021 3 Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cuminum cyminum L. populations etry detector (MSD) (Agilent Technologies, 5977A) was used. An HP-Innowax column (Agilent 19091N- 116: 60 m × 0.320 mm internal diameter and 0.25 μm film thickness) was used for the separation of the components. Samples were analyzed with the column held initially at 70 ºC with 5 min hold time. Then, the temperature increased to 160 ºC with 3 ºC min-1 heat- ing ramp. Finally, the temperature was raised to 250 ºC with 6 ºC min-1 heating ramp with 5 min hold time. Helium (99.999 % purity) was the carrier gas at 1.3 ml min-1 flow rate. The injection volume was 1μl (20 μl of volatile oil was dissolved in 1 ml of n-hexane). The solvent delay time was 8.20 min. The injection was in split mode (40 : 1). Detector, injector and ion source temperatures were 270 °C, 250 °C and 230 °C, respec- tively. MS scan range was (m z-1): 50-550 atomic mass units (AMU) under electron impact (EI) ionization of 70 eV . Retention indices were determined by the co-in- jection of C7-C30 n-alkanes (Sigma-Aldrich) to (GC/ FID) system (Agilent Technologies, 7890B) under the same conditions mentioned above. The volatile oils constituents were identified by the comparison of their retention indices and mass spectra by the com- puter library search database of US National Institute of Standards and Technology (NIST), Wiley libraries, other published mass spectra data (Adams, 2007) and the available data from our database. 2.4 LIPID EXTRACTION 50 g of grinded fruit samples were dissolved in 150 ml n-hexane at laboratory temperature for 12 h. n- hexane was removed with a rotary evaporator (40 °C) and the residue was stored at -10 °C until the fraction of the fatty acids could be determined. During the li- pid extraction, evaporation and storage steps, the sam- ples were kept away from light (Özgul Yücel, 2005). 2.5 ESTERIFICATION OF FATTY ACIDS Methyl esters of samples were prepared by a cold transmethylation using 2 ml KOH in methanol and n- -hexane with minor modifications (IUPAC, 1987). The extracted oil (0.5 g) was dissolved in 10 ml n-hexane fol- lowed by the addition of 1 ml of 2 ml methanolic KOH. The tubes were vortexed for 2 min. Finally, 1 ml of n- -hexane layer was taken for GC analysis. 2.6 DETERMINATION OF FATTY ACIDS Gas Chromatography analyses were carried out on a GC-2025 (Shimadzu Co., Kyoto, Japan) equipped with a flame ionization detector (FID). A capillary column DB-23 (60 m, 0.25 mm ID and 0.25 µm film thickness, J & W Scientific, Folsom, USA) was used. The oven temperature was scheduled as follows: 180 °C for 5 min, increased to 200 °C with 10 ºC min -1 heating ramp with 18 min hold time. Further, raised to 240 °C at the rate of 10 ºC min-1 for 20 min. Helium (99.999 %) was used as the carrier gas at 40 ml min-1 flow rate. The injection was performed in split mode (100 : 1). Detector and injector temperatures were 250 °C. Fatty acids standards had linear calibration curves (R 2 = 0.99). The GC method used was validated for fatty acids determination of cumin seed oil samples with 95 % confidence limits. Mean analytical recover- ies from the individual fatty acids in the oil samples were changed from 99.7 % to 100 %. The results were calculated as percentage peak area. The identification of FAMEs of samples was performed using a stand- ard FAMEs mixture (Sigma-Aldrich Chemicals 189- Table 1: The geographical and some climatic data of the plants sampling locations Bam 1 Zirkuh 1 Rayen 1 Cukurcak 2 Taskopru 2 Asagialicomak 2 Coordinates 29°04′N 33°36′N 29°35′N 38°42′N 38°34′N 38°58′N 58°21′E 59°59′E 57°26′E 31°22′E 31°18′E 31°42′E Elevation (m) 1050 1330 2201 1309 953 980 Climate Type Hot and dry climate Normal tropical climate Moderate mountainous/ dry Continental climate Continental climate Continental climate Rainfall (mm/ year) 68 150 93.8 501 501 421 1: Iran Meteorological Organization, 2: Turkish State Meteorological Service Acta agriculturae Slovenica, 117/2 – 2021 4 A. SOLTANBEIGI et al. 19). In addition, some parameters including the sum of saturated fatty acids (SFA), monounsaturated fatty acids (MUFA) and polyunsaturated fatty acids (PUFA) as well as petroselinic acid : linoleic acid ratio (PS : L), linoleic acid : linolenic acid (L : LN) ratio, iodine values (IV), oxidative susceptibility (OS) and theoreti- cal oxidative stability (TOSI) were determined. Iodine values were calculated from the fatty acid percentages by using the formula given by Maestri et al. (1998): IV = palmitoleic % × 1.001) + (oleic % × 0.899) + (linoleic % × 1.814) + (linolenic % × 2.73) Oxidative susceptibility (OS) was estimated from fatty acid values by using the formula given by Cert et al. (1996): Oxidative Susceptibility (OS) = MUFA + (45 × li- noleic) + (100 × linolenic) Theoretical oxidative stability (TOSI) was calcu- lated from fatty acids data by using the formula given by Chu and Kung, (1998): TOSI(h) = 7.5125 + palmitic % × (0.2733) + stear- ic % × (0.0797) + petroselinic % × (0.0159) + linoleic % × (-0.1141) + linolenic % × (-0.3962) 3 RESULTS AND DISCUSSION 3.1 VOLATILE OIL COMPONENTS The volatile oils from wild B. persicum and C. cyminum were pale yellow to brown and pale yellow, re- spectively. As shown in Tables 1 and 2, location and cli- mate significantly influenced the quantity and quality of volatile oils. The volatile oil content of Bam and Zirkuh B. persicum populations were 3.9 and 4.73 %, respective- ly. Volatile oil content for cultivated Rayen, Cukurcak, Taskopru and Asagialicomak populations of C. cyminum were 2.65, 2.2, 2 and 2.5 % (Table 2). According to the results, the volatile oil content of B. persicum populations was higher than that of C. cyminum populations. Various studies have reported similar results. Mazidi et al. (2012) reported that the volatile oil content of B. persicum was about 4.18 % and yellow. Another study on wild B. persi- cum, reported that the volatile oil content of plants col- lected from seven locations of Khorasan Province/Iran were about 3.1, 6.4, 6.7, 7.1, 7.5, 7.7 and 7.9 % (Talebi et al., 2018). Overall, the chemical differences between spe- cies are inevitable, and the yield and chemical constitu- ents of medicinal and aromatic plants (like other types of plants) are responsive to the genetic, geographical, cli- matic and seasonal conditions, agronomic practices, and harvest time (Y anive and Palevitch, 1982; Omidbaigi and Arvin, 2009). Elevation and temperature are the most important of these factors (Talebi et al., 2018). The essen- tial oil is made gradually from the beginning of the fruit, but its amount is low. The highest amount of essential oil is at a stage when the fruits are not yet fully mature. At the full maturity stage, a small amount of essential oil is reduced (Hornok, 1978). Monoterpenes were found as the main chemical group components in both species (Table 3). The levels of monoterpene hydrocarbons in B. persicum (57.17-64.53 %) were significantly higher than C. cyminum (39.37-39.5 %). Maximum monoterpene hydrocarbons in B. persi- cum and C. cyminum were recorded in Bam and Cuku- rcak populations, respectively. The amounts of oxygen- ated monoterpenes in C. cyminum (36.11-46.16 %) were richer than B. persicum (27.24-31.81 %). Sesquiterpenes levels were lower than monoterpenes. Biosynthesis of sesquiterpene hydrocarbon components in C. cyminum species was more than twice that of B. persicum. Even ox- ygenated sesquiterpenes components were not observed in B. persicum populations. Except for Cukurcak popula- tion in C. cyminum, other populations of this species had considerably high content of alcohol components than B. persicum. Esters and ethers were obtained in very minor amounts (Table 3). The results of chemical analysis (GC- MS/FID) of populations showed that C. cyminum species had a relatively higher compositional diversity. Bam and Zirkuh populations of B. persicum contained 31 and 30 components, respectively. Rayen and Cukurcak popula- tions of C. cyminum had 38 constituents. Taskopru (43) and Asagialicomak (44) contained a higher number of components (Table 2). From the oil constituents, 21 com- ponents were exclusive of C. cyminum populations. In contrast, nine components were specific to B. persicum populations. γ-terpinene (39.62 %),  cuminal (17.95 %), o-cy- mene (11.12 %), benzenemethanol, α-methyl- (7.49 %), 1-phenyl-1-butanol (6.41 %), limonene (6.41 %), β-pinene (2.29 %), α-pinene (1.90 %), isopulegone (1.09 %) and sabinene (1.01 %) were identified as the major constituents of Bam population. The major components of Zirkuh were γ-terpinene (33.62 %), cuminal (19.34 %), benzenemethanol, α-methyl- (9.52 %), limonene (8.66 %), 1-phenyl-1-butanol (8.41 %), o-cymene (5.37 %), α-pinene (2.12 %), terpinolene (1.38 %), isopulegone (1.27 %) and cuminol (1.05 %) (Table 2). Previous studies on B. persicum, support our findings on the major con- stituents of volatile oil (Foroumadi et al., 2002; Ehsani et al., 2016; Rustaie et al., 2016; Sanei Dehkordi et al., 2016; Khaledi and Hassani, 2018). Talebi et al. (2018), in their study with seven populations of wild B. persicum Boiss. from Northeast of Iran noted that γ-terpinene (29.2-40.1 %), cumin alcohol (16.4-28.4 %), cumin aldehyde (9-18.9 %), ρ-cymene (9.4-15.6 %), safranal (3.4-7.9%), limonene (3.7-6.4 %), β-pinene (0.8-2.3 %), α-pinene (0.3-1.7 %), Acta agriculturae Slovenica, 117/2 – 2021 5 Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cuminum cyminum L. populations and sabinene (0.8-1.2 %) were the main constituents of the volatile oils; very similar to the findings of our study. The results demonstrated that cuminal (22.80 %), benzenemethanol, α-methyl- (22.65 %), γ-terpinene (19.41 %), β-pinene (11.22 %), 1-phenyl-1-butanol (10.32 %), o-cymene (4.90 %) and isopulegone (1.49 %) were the dominant constituents in Rayen population of C. cymi- num. The main constituents of essential oils from Cukur- cak were cuminal (37.64 %), γ-terpinene (16.79 %), o-cy- mene (12.67 %), β-pinene (11.92 %), 1-phenyl-1-butanol (5.45 %), benzenemethanol, α-methyl- (5.3 %), isopu- legone (1.36 %), α-phellandrene (1.02 %) and α-pinene (1.01 %). The predominant components of Taskopru sample volatile oil were cuminal (26.75 %), γ-terpinene (16.76 %), benzenemethanol, α-methyl- (15.25 %), 1-phenyl-1-butanol (12.59 %), β-pinene (11.64 %), o- cymene (6.5 %) and isopulegone (1.54 %). Furthermore, in Asagialicomak population essential oil cuminal (24.18 %), γ-terpinene (18.26 %), benzenemethanol, α-methyl- (17.48 %), β-pinene (11.35 %), 1-phenyl-1-butanol (9.76 %), o-cymene (6.41 %), α-phellandrene (2.36 %), isopu- legone (1.23 %) and α-pinene (1.02 %) were found as the main components (Table 2). Moghaddama and Ghasemi Pirbalouti, (2017), compared 20 C. cyminum accessions and determined γ-terpinene (26.53-37.81 %), ρ-cymene (12.84-21.22 %), cumin aldehyde (9.45-20.66 %), cumin alcohol (1.63-15.22 %), β-pinene (8.32-13.84 %) and safranal (2.3-6.37 %) as the major constituents. in anoth- er study, propanal (26.19 %), benzenemethanol (25.4 %), 1-phenyl-1-butanol (16.49 %), γ-terpinene (13.04 %), β-pinene (7.28 %), cymene (4.24 %) and pulegone (2.58 %) were identified as the main components of this plant (Haghiroalsadat et al., 2011). In another study, the oil constituents of fruit samples from Emirdag (T urkey) were cumin aldehyde (19.25-24.80 %), p-mentha-l,3-dien-7-al (7.54-9.30 %), p-mentha-l,4-dien-7-al (36.51-44.91 %), γ-terpinene (8.61-9.72 %), ρ-cymene (5.94-6.45 %) and β-pinene (4.99-5.60 %) (Baser et al., 1992). The results of our study are in line with the findings of various stud- ies on the chemical components of cumin (Rihawy et al., 2014; Esmaeili, 2015; Moghaddama et al., 2015; Tahir et al., 2016). Among the major components identified in all populations, γ-terpinene (39.62 %) was the highest in Zirkuh and cuminal (37.64 %) in Cukurcak. 3.2 FATTY ACID COMPONENTS In total, 15 fatty acids were identified from the fat- ty oil of B. persicum populations of Iranian origin (Table 4). Based on the results, palmitic acid, petroselinic acid, linoleic acid, linolenic acid and behenic acid were the major components of Bam and Zirkuh populations of B. persicum. Lauric acid (37.08 %) and linoleic acid (33.60 %) were determined as the major fatty oil components of Bam and Zirkuh populations of B. persicum, respectively. Besides, capric acid and gadoleic acid from Bam and ste- aric acid from Zirkuh were the other major constituents. Except for lignoceric acid, which was not present in C. cyminum population oils, the other components were common in both species. Petroselinic acid (47.53-55.51 %), linoleic acid (22.58-26.32 %), lauric acid (13.46 %) and palmitic acid (2.68-3.03 %) were identified as the major components of C. cyminum populations. Petrose- linic acid content in C. cyminum was significantly higher than in B. persicum. Comparisons between B. persicum populations from two different countries showed no do- minant differences in terms of fatty acid components. The monounsaturated fatty acids especially petrose- linic acid have great importance because of their high nu- tritional value and the contribution to the oxidative sta- bility of oils (Bettaib et al., 2012; Rebey et al., 2012; Rebey et al., 2013). The oils from C. cyminum populations fruits were characterized by the presence of a high proporti- on of monounsaturated and polyunsaturated fatty acids. Our findings are similar to the previous studies (Bettaib et al., 2012; Rebey et al., 2012; Rebey et al., 2013; Keskin and Baydar, 2016; Milica et al., 2016; Hajib et al., 2018). Oil samples from two species were rich in petroselenic acid (29-55 %). This fatty acid is the iconic characteristic of the seeds oil from Apiaceae species. These oils have potential industrial significance, especially in the paint industry (Bettaib et al., 2012; Rebey et al., 2013). Linoleic acid as a predominant polyunsaturated fat- ty acid was also present in both species at appreciable le- vels. Considering linoleic acid and other polyunsaturated fatty acids profiles, our finding is similar to Milica et al. (2016) and Hajib et al. (2018). Nevertheless, some other studies reported lower values than our research (Bettaib et al., 2012; Rebey et al., 2012; Rebey et al., 2013). The saturated fatty acids (lauric and palmitic acids acids) ex- hibited a vast variability (15.13-37.08 %). The minimum recommended value for PUFA : SFA ratio is 0.5 g (HMSO, 1994), which is significantly lower than our findings (0.79-1.41) except for Bam population of B. persicum (0.39). There is no scientific information for the PUFA : SFA ratio in previous studies on C. cymi- num and B. persicum (Table 4). The changes for petroselinic acid : linoleic acid ratio, which is important for the estimation of oxidative stabili- ty, were 0.78-1.59 for B. persicum populations and 2-2.18 for C. cyminum samples. Overall, it can be pointed out that the oxidative stability of C. cyminum populations appears to be relatively higher than B. persicum popula- tions. The present results are in agreement with Bettaieb et al. (2013). The above-mentioned components have in- Acta agriculturae Slovenica, 117/2 – 2021 6 A. SOLTANBEIGI et al. RT a RI b Components (%) B. persicum C. cyminum ID Bam Zirkuh Rayen Cukurcak Taskopru Asagialicomak 8.813 1032 α-pinene 1.903 2.12 0.855 1.01 0.962 1.029 1 9.838 1079 camphene - 0.338 - - - - 1 10.936 1120 β-pinene 2.292 2.61 11.225 11.928 11.649 11.352 1 11.256 1131 sabinene 1.015 0.981 0.688 0.695 0.684 0.724 1 12.103 1158 δ-3-carene 0.074 - 0.04 0.043 0.043 0.04 1 12.418 1168 β-myrcene 0.789 0.759 0.704 0.617 0.691 0.746 1 12.635 1175 α-phellandrene - - 0.603 1.024 0.985 2.362 1 13.121 1190 α-terpinene 0.318 0.429 0.172 0.118 0.153 0.166 1 13.791 1210 limonene 6.415 8.665 0.333 0.39 0.318 0.39 1 14.146 1219 1,8-cineole - 0.343 - - - - 1 14.163 1220 β-phellandrene 0.462 0.355 0.396 0.466 0.458 0.569 1 14.919 1240 cis-ocimene - 0.18 - - - - 1 15.547 1256 γ-terpinene 39.627 33.62 19.418 16.795 16.762 18.264 1 16.503 1281 o-cymene 11.122 5.377 4.904 12.676 6.505 6.413 1 16.932 1293 terpinolene 0.357 1.386 0.044 0.055 0.05 0.056 1 24.125 1469 trans-sabinene hydrate 0.046 - 0.036 0.041 - 0.046 1 25.418 1501 α-copaene - - 0.252 0.318 0.326 0.334 2 27.186 1546 β-gurjunene - - 0.046 0.039 0.07 0.08 1 27.369 1550 linalool - - 0.03 - 0.03 - 1 27.506 1554 cis-sabinene hydrate - - 0.092 - 0.067 0.058 1 28.119 1569 trans-2-menthenol - - - 0.084 0.047 0.081 1 28.582 1581 isopulegone 1.096 1.272 1.49 1.363 1.547 1.233 1 28.948 1590 bornyl acetate 0.053 0.554 0.035 0.041 0.035 0.071 1 29.046 1592 trans-α-bergamotene - - 0.063 0.089 0.09 0.106 1 29.67 1608 caryophyllene - 0.261 0.135 0.334 0.255 0.433 1 29.721 1610 terpinene-4-ol 0.471 0.528 - - - - 1 30.625 1633 cis-2-menthenol - - - 0.061 0.036 0.058 1 31.781 1664 trans -pinocarveol - - 0.055 0.059 0.073 0.067 1 32.05 1671 trans-β-farnesene - - 0.264 0.285 0.358 0.395 1 32.181 1674 (-)-isoledene - - - - 0.043 0.048 3 32.433 1681 α-humulene - - - - 0.033 0.07 1 32.908 1693 β-farnesene 0.046 - 0.034 - - - 1 33.177 1701 (-)-β-acoradiene - - 0.156 0.325 0.185 0.335 1 33.251 1702 γ-muurolene 0.114 0.146 0.188 - - - 1 33.303 1704 γ-curcumene - - - - 0.231 0.239 1 33.898 1720 germacrene D 0.15 0.172 - - - - 1 34.167 1727 zingiberene 0.137 - - - 0.028 - 1 34.396 1733 phellandral 0.18 0.215 - 0.182 0.207 0.167 1 34.745 1742 β-selinene - - 0.042 0.071 0.07 0.073 1 34.831 1745 (-)-carvone 0.215 0.201 0.138 - - - 1 Table 2: Volatile oil components of B. persicum and C. cyminum populations from Iran and Turkey Acta agriculturae Slovenica, 117/2 – 2021 7 Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cuminum cyminum L. populations Grouped chemical components(%) B. persicum C. cyminum Bam Zirkuh Rayen Cukurcak Taskopru Asagialicomak Monoterpene hydrocarbons 64.531 57.175 39.501 45.867 39.378 42.232 Oxygenated monoterpenes 27.245 31.814 36.11 46.166 42.676 36.986 Sesquiterpene hydrocarbons 0.532 0.579 1.18 1.461 1.689 2.258 Oxygenated sesquiterpenes - - 0.34 1.082 0.902 0.889 Alcohols 7.493 9.525 22.654 5.3 15.25 17.487 Esters 0.098 0.739 0.035 0.041 0.035 0.071 Ethers 0.101 0.092 - - - - Others - - 0.032 0.082 0.07 0.074 Total (%) 100 99.924 99.852 99.999 100 99.997 Table 3: Grouped chemical components of B. persicum and C. cyminum populations essential oil from Iran and Turkey RT a RI b Components (%) B. persicum C. cyminum ID Bam Zirkuh Rayen Cukurcak Taskopru Asagialicomak 35.025 1750 cis-piperitol - - - 0.045 - 0.052 1 36.038 1777 β-sesquiphellandrene 0.085 - - - - 0.145 1 36.974 1802 cuminal (cumin aldehyde) 17.95 19.345 22.809 37.642 26.758 24.181 1 37.125 1805 1-phenyl-1-butanol 6.417 8.412 10.32 5.45 12.59 9.765 1 37.480 1813 benzenemethano, α-methyl- 7.493 9.525 22.654 5.3 15.25 17.487 1 38.447 1835 anethole - - - 0.134 0.04 0.073 1 40.289 1877 isoterpinolene 0.157 0.355 0.119 0.05 0.118 0.121 3 44.072 1977 cuminyl acetate 0.045 0.185 - - - - 1 45.138 2008 caryophyllene oxide - - 0.058 0.133 0.097 0.081 1 45.743 2029 carotol - - 0.282 0.949 0.702 0.758 1 46.435 2054 α,α’-dihydroxy-m- diisopropylbenzene - - 0.032 0.082 0.07 0.074 3 46.982 2073 p-mentha-1,4-dien-7-ol 0.172 0.37 0.403 0.279 0.365 0.368 1 47.551 2093 viridiflorol - - - - 0.103 0.05 1 47.922 2107 cuminol (cumin alcohol) 0.644 1.051 0.686 0.638 0.832 0.75 1 49.874 2190 thymol 0.054 0.077 - - - - 1 50.52 2220 carvacrol - - 0.051 0.188 0.084 0.087 1 53.644 2384 dill apiole 0.101 0.092 - - - - 1 Volatile oil content (%) 3.9 4.73 2.65 2.2 2.0 2.5 RT: Retention time; RI: Retention indices calculated against n-alkanes (C7-C30) on HP-Innowax column; ID: Identification method 1: RI-MS; 2: RI-Rf; 3: MS dustrial applications especially in the manufacturing of oil based paints (Bettaib et al., 2012; Rebey et al., 2013). The ratio of linoleic acid : linolenic acid is a pro- minent indicator for comparing the relative nutritional value of oils from different plant sources (Rebey et al., 2013). This value varied widely among the populations of both species tested. C. cyminum had significantly higher values than B. persicum (Table 4). The iodine values were calculated according to the fatty acid components. The saturated fatty acids, mono- Acta agriculturae Slovenica, 117/2 – 2021 8 A. SOLTANBEIGI et al. Fatty Acid (%) B. persicum C. cyminum Bam Zirkuh Rayen Asagialicomak Cukurcak Taskopru Capric acid C 10 : 0 3.09 0.71 0.24 0.82 0.65 0.68 Lauric acid C 12 : 0 37.08 22.92 16.21 15.13 24.22 13.46 Myristic acid C 14 : 0 0.86 0.34 0.1 0.23 0.75 0.21 Palmitic acid C 16 : 0 4.53 6.24 3.03 2.89 2.68 2.99 Palmitoleic acid C 16 : 1 0.43 0.25 0.35 0.39 0.34 0.35 Margaric acid C 17 : 0 0.21 0.51 0.03 0.02 0.03 0 Margoleic acid C 17 : 1 0.59 0.26 0.04 0.03 0.06 0.07 Stearic acid C 18 : 0 0.97 1.99 0.60 0.67 0.56 0.72 Petroselinic acid C 18 : 1 (n-6) 29.12 26.36 52.64 53.51 47.53 55.51 Linoleic acid C 18 : 2 (n-6) 18.34 33.60 26.32 25.76 22.58 25.49 Linolenic acid C 18 : 3 (n-3) 1.01 4.82 0.24 0.27 0.30 0.17 Arachidic acid C 20 : 0 0.12 0.14 0.05 0.04 0.06 0.04 Gadoleic acid C 20 : 1 1.18 0.55 0.13 0.20 0.14 0.27 Behenic acid C 22 : 0 2.05 1.04 0.03 0.61 0.10 0.06 Lignoceric acid C 24 : 0 0.33 0.28 ND ND ND ND Saturated fatty acids (SFA %) 49.24 34.17 20.05 20.41 29.05 18.16 Monounsaturated fatty acids (MUFA %) 31.32 27.42 53.16 54.13 48.07 56.20 Polyunsaturated fatty acids (PUFA %) 19.35 38.42 26.56 26.03 22.88 25.66 PUFA : SFA 0.39 1.12 1.32 1.28 0.79 1.41 MUFA : PUFA 1.62 0.71 2 2.08 2.1 2.19 Petroselinic acid : Linoleic acid 1.59 0.78 2 2.08 2.1 2.18 Linoleic acid : Linolenic acid 18.16 6.97 109.67 95.41 75.15 149.94 Iodine value 62.64 98.09 96.08 95.96 84.85 96.96 Oxidative susceptibility 957.62 2021.42 1261.56 1240.33 1094.17 1220.25 Theoretical oxidative stability index (TOSI) hours 6.79 4.04 6.12 6.15 6.34 6.29 Table 4: Fatty acid components and some parameters related with fatty oil quality of B. persicum and C. cyminum populations from Iran and Turkey unsaturated fatty acids and polyunsaturated fatty acids levels of samples influenced the iodine values (Maestri et al., 1998). Oxidative susceptibility was estimated based on the fatty acids profile. According to Table 4, no signi- ficant variation was observed in the oxidative susceptibi- lity of C. cyminum populations. However, this value for Zirkuh population was twice more than that of B. persi- cum (Bam population). The variations for Iodine values, oxidative suscepti- bility and theoretical oxidative stability index for all the samples were almost similar due to the homogenous un- saturated fatty acids profiles. All these values represent the theoretical stability of the oil (Chu and Kung, 1998). Generally, the oxidative susceptibility and theoreti- cal oxidative stability index values of samples were cor- respondingly increased with high linoleic acid content more than monounsaturated fatty acids (especially pe- troselinic acid). Linoleic acid is much more susceptible to oxidation than monounsaturated fatty acids (Chu and Kung, 1998). However, there is no available data on iodi- ne values, oxidative susceptibility and theoretical oxidati- ve stability index on C. cyminum and B. persicum. The differences in fatty acids profiles of C. cyminum and B. persicum populations from various localities of Iran and Turkey are seemingly dependent on the gene- tic factors (Bettaib et al., 2012; Rebey et al., 2013), en- vironmental and edaphic characteristics and agricultural practices (Bettaib et al., 2012; Rebey et al., 2013; Keskin and Baydar, 2016) as well as they depend upon the large geographical variations (Keskin and Baydar, 2016; Hajib et al., 2018). Acta agriculturae Slovenica, 117/2 – 2021 9 Chemical components of volatile oil and fatty acids of wild Bunium persicum (Boiss.) B. Fedtsch. and cultivated Cuminum cyminum L. populations 4 CONCLUSIONS Our findings showed significant differences in the volatile oil content, volatile oil and fatty oil constituents’ profile of B. persicum and C. cyminum populations from Iran and Turkey. It can be inferred that genetic charac- teristics, location (region) and climatic conditions have sensible effects on the oil contents and its ingredients. As known, the production of primary and secondary meta- bolites in plants is directly and continuously associated with multiple biotic and abiotic factors. The identificati- on and characterization of secondary metabolites profi- le in medicinal plants and especially in native plants are crucial to assign a specific characteristic for those pre- cious species and, to make them new candidates for the multidisciplinary use with several industries. Besides, the identification of compositional profile of native neglected plant species labels the plants a recognizable criterion for the commercial cultivation and exploitation. Moreover, by the characterized secondary metabolites profile; natu- ral habitats will be safer and intact since, the agricultural systems try to concentrate on a defined species producti- on and, the miss and over-harvesting of the related spe- cies will be limited in favor of natural habitats diversity. Inline, identifying the major components and the possible chemotypes and the characterization of bioac- tive substances with the potential pharmaceutical ap- plication from medicinal and aromatic plants provide a broaden way and horizon in front of the producers, en- trepreneurs and policy makers for the efficient utilization of natural habitats and cultivated plants. 5 REFERENCES Adams, R. P. (2007). Identification of essential oil components by Gas Chromatography/Mass Spectrometry. 4 th Ed. 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