UDC 575.630 DOI: 10.2298/GENSR1603101G Original scientific paper

DIVERSITY IN CHEMICAL COMPOSITION AND YIELD OF ESSENTIAL OIL FROM TWO MENTHA SPECIES

Ahmad Reza GOLPARVAR1*, Amin HADIPANAH2

1Department of Agronomy and Plant Breeding, (Khorasgan) Branch, Islamic Azad University, Isfahan, 2Department of Horticultural, Science and Research Branch, Islamic Azad University, Tehran, Iran

Golparvar R. A. and A. Hadipanah (2016): Diversity in chemical composition and yield of essential oil from two Mentha species.- Genetika, Vol 48, No.3, 1101 - 1110. The genus Mentha, which belongs to the mint family (Lamiaceae). Essential oil yield and chemical components of two Mentha species including Mentha longifolia (L.) Huds. and (Mentha spicata L.) collected from three ecotypes in Iran were investigated. The essential oils of samples were obtained by hydro-distillation, and analyzed using gas chromatography–mass spectrometry (GC–MS). A significant difference (p < 0.05) in oil yields was obtained from the aerial parts of two Mentha species. The essential oil yields were obtained from the aerial of M. longifolia, 0.62, 0.85 and 1.24 ml / 100 g dry matter identified in , Saman and Kuhrang province, respectively and the aerial of M. spicata, 0.49, 1.02 and 1.54 ml / 100 g dry matter identified in Ardestan, Saman and Kuhrang province, respectively. Results indicated significant differences (p < 0.01) among the aerial for the main constituents in the essential oil from two Mentha species. The major constituents of the essential oil from the aerial of M. longifolia collected from Ardestan province were pulegone (31.21%), 1,8-cineole (23.01%), sabinene (6.76%), the aerial of M. longifolia collected from Saman province were pulegone (31.06%), 1,8-cineole (24.34%), sabinene (7.45%) and the aerial of M. longifolia collected from Kuhrang province were pulegone (36.42%) and 1,8-cineole (29.49%). The major constituents of the essential oil from the aerial of M. spicata collected from Ardestan province were 1,8-cineole (35.28%), carvone (30.71%), the aerial of M. spicata collected from Saman province were carvone (35.37%), 1,8-cineole (24.35%), pulegone (18.67%) and the aerial of M. spicata collected from Kuhrang province were

______Corresponding author: Ahmad Reza Golparvar, Department of Agronomy and Plant Breeding, Isfahan (Khorasgan) Branch, Islamic Azad University, P.O.Box:81595-158, Isfahan, Iran, e-mail:[email protected]

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carvone (41.51%), 1,8-cineole (25.95%). Generally, a comparison of our results with the previous reports suggests differences in the essential oil compositions and oil yield of the plant material could be attributed to genetic diversity in two Menthe species. Keywords: chemical constitutes, genetic diversity, Mentha longifolia L., Mentha spicata L. INTRODUCTION The genus Mentha, which belongs to the mint family (Lamiaceae), subfamily Nepetoideae (BREMER et al. 1998). The genus Mentha includes 25 to 30 species that grow in the temperate regions of Eurasia, Australia and South Africa (DORMAN et al. 2003). The species of section Mentha typically have chromosome number 2n=2x=12, but the other species vary widely, with (M. spicata) and (M. longifolia) have 2n=2x=48 and 2n=2x=24, respectively. The spearmint, M. spicata, is a hybrid of M. longifolia and M. rotundifolia, morphological, cytological and biochemical data have shown that the tetraploid species of M. spicata (2n=48) (LAWRENCE, 2007) originated by chromosomal doubling of hybrids between the two closely related and inter-fertile diploids, M. longifolia and M. suaveolens (HARLEY & BRIGHTEN, 1977). The essential oils of some Mentha species are potential candidates for exhibiting antimicrobial, antioxidant, antispasmodic, carminative, radical-scavenging and cytotoxic activities (GULLUCE et al. 2007). The essential oil from the areial parts of mentha consists of a wide and varying array of chemical constituents, depending on variations in chemotypes, leaf and flower, aroma, and origin of the plants (ZNINI et al. 2011; GOLPARVAR et al. 2015; ABEDI et al. 2015) In studies (JAYMAND & REZAEI, 2002) indicated the major constituents obtained from of Mentha longifolia (L.) Huds. var. asiatica (Boriss.) Rech. f. of the leaf oil were; piperitone (67.6%), isomenthone (6.6%) and cis-piperitol (4.2%), while the flower oil contained piperitone (55.7%), carvone (16.2%) and pulegone (4.1%). An earlier report by (JAMZAD et al. 2013) indicated the major components aerial parts of Mentha longifolia (L.) Hudson var. chlorodictya Rech. f. collected from two different locations in (Gilan and Mazandaran Provinces) Iran were Cis-piperitone oxide (36.4 and 40.5%), piperitenone oxide (22.5 and 37.3%) and caryophyllene oxide (13.65 and 7.43%). CHAUHAN et al. (2008) reported that the Mentha spicata L. (spearmint) collected from different sub-tropical and temperate zones of North-West Himalayan region of India were carvone between 49.62–76.65%, second major component was limonene between 9.57–22.31%, 1,8-cineole varied between 1.32–2.62%, whereas trans-carveol varied between 0.3- 1.52%. Various researchers reported that essential oil yield and its components in medicinal and aromatic plants in general is primarily related to their genetic (SHAFIE et al. 2009), climate, edaphic, elevation and topography (LOZIENE & VENSKUTONIS, 2005; GHASEMI PIRBALOUTI & MOHAMMADI, 2013). The main goal of this study was determine the variation of chemical composition and yield of the essential oils from the aerial parts of Mentha longifolia (L.) Huds. and (Mentha spicata L.) in Iran.

MATERIALS AND METHODS Plant material The aerial parts of two Mentha species including Mentha longifolia (L.) Huds. and (Mentha spicata L.) were collected from three ecotypes, Ardestan (Isfahan) province in center Iran (33° 22' N and 52° 22' E) about 1562 m above sea level, Saman (Chaharmahal va Bakhtiari) A.R. GOLPARVAR et al.: CHEMICAL COMPOSITION AND YIELD OF ESSENTIAL OIL OF MENTHA 1103 province (32° 27' N and 50° 54' E) about 1871 m above sea level, and Kuhrang (Chaharmahal va Bakhtiari) province in the Southwest of Iran (32° 28' N and 50° 07' E) about 2021 m above sea level during 2014. Plant identities were confirmed by Herbarium of Research Center of Isfahan (Khorasgan) Branch.

Essential oil extraction Harvested fresh aerial parts of two Mentha species were dried at room temperature (25 ± 5 °C). Dried plant material was powered (100 gm, and subjected to hydro–distillation (1000 ml distillated water) for 3 hrs using a Clevenger-type apparatus according to the method recommended in BP (BRITISH PHARMACOPOEIA, 1988). Samples were dried with anhydrous sodium sulfate and kept in amber glass vials at 4◦C ± 1◦C until use.

Identification of the oil components Compositions of the essential oils were determined by GC–MS. The GC/MS analysis was carried out with an Agilent 5975 GC-MSD system. HP-5MS column (30 m x 0.25 mm, 0.25 μm film thickness) was used with helium as carrier gas with flow rate of 1.0 mL/min. The oven temperature was kept 20°C at 50°C for 4 min and programmed to 280°C at a rate of 5°C /min, and kept 20°C constant at 280 °C for 5 min, at split mode. The injector temperature was at 20°C at 280°C. Transfer 20 line temperatures 280°C. MS were taken at 70 eV. Mass range was from m/z 35 to 450. Identification of the essential oil components was accomplished based on comparison of retention times with those of authentic standards and by comparison of their mass spectral fragmentation patterns (WILLEY/ChemStation data system) (ADAMS, 2007).

Statistical analyses The data was statistically analyzed using SPSS (19.0) software based on the model of completely randomized design (CRD). Means of the ecotypes (for main constituents of the essential oils) were compared by Duncan’s multiple range test at p ≤ 0.05 level.

RESULTS AND DISCUSSION Essential oil yield The essential oils extracted from the aerial parts of two Mentha species produced a clear, yellow liquid. A significant difference (p < 0.05) in oil yields was obtained from the aerial parts of two Mentha species. The essential oil yields were obtained from the aerial of M. longifolia, 0.62, 0.85 and 1.24 ml / 100 g dry matter identified in Ardestan, Saman and Kuhrang province, respectively (Table. 1). The essential oil yields were obtained from the aerial of M. spicata, 0.49, 1.02 and 1.54 ml / 100 g dry matter identified in Ardestan, Saman and Kuhrang province, respectively (Table. 2).

Chemical composition Results indicated significant differences (p < 0.01) among the aerial for the main constituents in the essential oil from two Mentha species (Table 1, 2). The chemical constituents identified by GC-MS, are presented in Table 1. GC–MS analyses resulted in M. longifolia essential oil, 32, 29 and 33 compounds were identified in Ardestan, Saman and Kuhrang province, respectively. The oil of Ardestan components 1104 GENETIKA, Vol. 48, No3, 1101-1110, 2016 corresponding to 99.97% and consisted mainly of oxygenated monoterpenes (80.11%) with a small amount of monoterpene hydrocarbons (18.81%) and sesquiterpene hydrocarbons (1.05%). The major constituents of the oil Ardestan were pulegone (31.21%), 1,8-cineole (23.01%), sabinene (6.76±0.6%) and γ-terpinene (5.43±1.3%) (Fig 1).

Table 1 Chemical compositions of essential oils of three ecotypes Mentha longifolia L. % GC peak area Row Compounds RI Ardestan Saman Kuhrang ANOVA 1 α-Thujene 926 0.23 - - 2 α-Pinene 935 2.03 ±0.2a 1.87 ±0.1a 0.41 ±0.1b p < 0.01 3 Camphene 950 2.51±0.4a 0.48±0.1b 0.32±0.1b p < 0.01 4 Sabinene 975 6.76±0.6a 7.45±1.1a 3.61±0.4b p < 0.01 5 β-Myrcene 994 0.21 0.82 0.18 6 1,8-Cineole 1035 23.01 24.34 29.49 7 (Z)-β-Ocimene 1045 0.16 0.21 - 8 γ-Terpinene 1063 5.43±1.3a 3.54±0.5ab 2.12±0.2b p < 0.01 9 Terpinolene 1087 1.48 0.75 0.19 10 Linalool 1103 0.56 0.56 0.23 11 3-Octanol, acetate 1113 - 0.26 - 12 2-Octanol, acetate 1127 0.21 0.34 0.21 13 cis-Allo-ocimene 1130 0.19 - 0.24 14 1,3-Benzenediol, 4-ethyl 1138 1.08 1.59 0.37 15 trans-Pinocarveol 1144 4.37±0.6a 5.12±1.2a 0.49±0.1b p < 0.01 16 Menthone 1155 3.89 2.31 - 17 (-)-Pinocarvone 1160 0.01 - 0.05 18 Mnthofuran 1168 3.82 3.83 3.21 19 Borneol 1170 - 0.19±0.1b 2.61±0.1a p < 0.01 20 Isopulegone 1185 0.21±0.1b 0.21±0.2b 4.43±0.5a p < 0.01 21 Myrtanol 1192 1.71 1.12 0.93 22 α-Terpineol 1195 2.87±0.3b 4.94±0.5a 1.76±0.3b p < 0.01 23 trans-Carveol 1219 0.21 - 0.67 24 cis-Carveol 1230 0.69±0.1b 0.23±0.2b 5.41±1.1a p < 0.01 25 Pulegone 1235 31.21 31.06 36.42 26 Carvone 1244 - - 0.01 27 Piperitone 1254 0.54 0.56 0.41 28 Isobornyl acetate 1273 0.21 0.21 0.49 29 Naphthalene, 1-isocyano- 1294 0.36 0.39 0.25 30 Pulespenone 1345 0.16 - 0.46 31 α-Terpinolene 1349 2.48±0.3a 0.21±0.2b 1.69±0.2ab p < 0.01 32 Piperitenone oxide 1363 2.32±0.5ab 5.39±1.1a 0.35±0.1b p < 0.01 33 β-Bourbonene 1415 0.21 - 1.15 34 β-Caryophyllene 1425 0.31 0.34 0.35 35 α-Humulene 1458 0.53 1.34 0.65 36 Germacrene-D 1575 - - 0.57 37 Caryophyllene oxide 1583 - 0.26 0.29 Monoterpene hydrocarbons 18.81 15.12 6.83 Oxygenated monoterpenes 80.11 82.86 88.68 Sesquiterpene hydrocarbons 1.05 1.68 2.72 Oxygenated sesquiterpenes - 0.26 0.29 Total 99.97 99.92 98.52 Essential oil yield (%) 0.62±0.3b 0.85±0.1ab 1.24±0.5a p < 0.05 RI: Retention indices determined on HP-5MS capillary column.

A.R. GOLPARVAR et al.: CHEMICAL COMPOSITION AND YIELD OF ESSENTIAL OIL OF MENTHA 1105

Table 2 Chemical compositions of essential oils of three ecotypes Mentha spicata L. % GC peak area Row Compounds RI Ardestan Saman Kuhrang ANOVA 1 α-Pinene 935 4.92±0.6a 0.19±0.1b 0.87±0.1b p < 0.01 2 Camphene 950 - 0.02 0.01 3 Sabinene 975 8.85±1.2a 0.64±0.1b 2.19±0.5ab p < 0.01 4 β-Myrcene 994 2.86±0.4a 0.29±0.1b 0.42±0.1b p < 0.01 5 1,8-Cineole 1035 35.28±2.2a 24.35±2.1b 25.95±2.2b p < 0.01 6 (Z)-β-Ocimene 1045 0.24 - - 7 γ-Terpinene 1063 - 0.47 0.45 8 Terpinolene 1087 0.53 - - 9 Linalool 1103 0.46 - 0.25 10 3-Octanol, acetate 1113 0.43 - - 11 1,3-Benzenediol, 4-ethyl 1138 1.39 0.28 0.63 12 trans-Pinocarveol 1144 0.39 - - 13 Menthone 1155 0.28 1.23 0.92 14 (-)-Pinocarvone 1160 - 1.59 0.82 15 Mnthofuran 1168 0.24 - - 16 Borneol 1170 1.61±0.2b 3.85±0.5a 3.71±0.4a p < 0.01 17 Isopulegone 1185 0.59±0.2b 3.24±1.3a 2.08±1.1ab p < 0.01 18 α-Terpineol 1195 - 0.37 0.36 19 Trans dihydrocarvone 0.46 0.77 0.52 20 trans-Carveol 1219 - 0.48 0.45 21 cis-Carveol 1230 - 2.45 2.21 22 Pulegone 1235 1.99±0.6b 18.67±2.3a 11.92±1.1ab p < 0.01 23 Carvone 1244 30.71±1.3b 35.37±1.2ab 41.51±2.4a p < 0.01 24 Piperitone 1254 - 0.21 0.52 25 Isobornyl acetate 1273 0.37 - 26 Naphthalene, 1-isocyano- 1294 - 1.11 - 27 Pulespenone 1345 0.69 - - 28 α-Terpinolene 1349 0.19 - 0.32 29 Piperitenone oxide 1363 0.38 0.27 - 30 β-Bourbonene 1415 1.21 0.34 0.84 31 β-Caryophyllene 1425 5.52±1.1a 1.04±0.5b 2.35±1.1ab p < 0.01 32 β-copaene 1434 0.41 0.53 - 33 α-Humulene 1458 0.40 0.01 - 34 Germacrene-D 1575 0.19 - - 35 Caryophyllene oxide 1583 - 0.36 0.24 Monoterpene 17.4 1.61 3.94 hydrocarbons Oxygenated monoterpenes 74.79 94.61 92.17 Sesquiterpene 7.73 1.91 3.19 hydrocarbons Oxygenated - 0.36 0.24 sesquiterpenes Total 99.92 98.49 99.54 Essential oil yield (%) 0.49±0.2b 1.02±0.4ab 1.54±0.6a p < 0.05 RI: Retention indices determined on HP-5MS capillary column.

The oil of Saman components corresponding to 99.92% and consisted mainly of oxygenated monoterpenes (82.86%) with a small amount of monoterpene hydrocarbons 1106 GENETIKA, Vol. 48, No3, 1101-1110, 2016

(15.12%) and sesquiterpene hydrocarbons (1.68%). The major constituents of the oil Saman were pulegone (31.06%), 1,8-cineole (24.34%) and sabinene (7.45±1.1%) (Fig 2). The oil of Kuhrang components corresponding to 98.52% and consisted mainly of oxygenated monoterpenes (88.68%) with a small amount of monoterpene hydrocarbons (6.83%) and sesquiterpene hydrocarbons (2.72%). The major constituents of the oil Kuhrang were pulegone (36.42%) and 1,8-cineole (29.49%) (Fig 3). An earlier report by (GOLPARVAR et al. 2015) indicated the major components aerial parts of Mentha longifolia (L.) Hudson collected from four different locations in (, Chadegan, Isfahan and Provinces) Iran were 1,8-cineole (13.8 to 29.7%) and pulegone (7.8 to 44.75%). In studies of SAEIDI et al. (2012) the major compounds Mentha longifolia (L.) Hudson grown wild in Iran were piperitenone oxide (7.41 to 59.67%), pulegone (3.61 to 49.43%), 1,8– cineole (7.25 to 24.66%), α-terpineol (2 to 6%) and β-pinene (1.32 to 4.19%). In studies (RALUCA ANDRO et al. 2011) the major compounds M. longifolia were piperitone-oxide (36.74%), limonene (17.61%), β-cubebene (8.05%), β-mircene (7.38%), trans-β-ocimene (5.64%) and β- cariophyllene (3.20%). In studies (GOLPARVAR et al. 2013a) indicated the major components aerial parts of Mentha longifolia (L.) collected from two different locations in (Isfahan and Lorestan Provinces) Iran were Piperitone oxide (6.7 and 15.05%) and Pulegone (6.6 and 9.58%). A comparison of our results with the previous report by (SAEIDI et al. 2012; GOLPARVAR et al. 2013a; GOLPARVAR et al. 2015) suggests few differences in the volatile composition of the plant material could be attributed to the growth and cultivation conditions of the plant, to the methods of extraction and to the harvesting time. The chemical constituents identified by GC-MS, are presented in Table 2. GC–MS analyses resulted in M. spicata essential oil, 25, 26 and 23 compounds were identified in Ardestan, Saman and Kuhrang province, respectively. The oil of Ardestan components corresponding to 99.92% and consisted mainly of oxygenated monoterpenes (74.79%) with a small amount of monoterpene hydrocarbons (17.4%) and sesquiterpene hydrocarbons (7.73%). The major constituents of the oil Ardestan were 1,8-cineole (35.28%), carvone (30.71%), sabinene (8.85%) and β-caryophyllene (5.52%) (Fig 4). In studies (GOLPARVAR et al. 2013b) the chemical composition of three ecotypes of spearmint (Mentha spicata L.) in were carvone, 1,8-cineole, limonene and piperitenone oxide. In studies (PADALIA et al. 2013) carvone (51.3-65.1%), limonene (15.1- 25.2%), β-pinene (1.3-3.2%) and 1,8-cineole (≤0.1-3.6%) were the major constituents in the essential oils from five cultivars of M. spicata, while in one cultivar (Ganga) of M. spicata the major constituents were piperitenone oxide (76.7%), α- terpineol (4.9%), and limonene (4.7%). Recent findings indicated that some of the medicinal plant characteristics can be affected by genetic and ecological factors, including precipitation, temperature and plant competition. Since essential oils are the product of a predominantly biological process further studies are needed to evaluate if the reported characteristics of each population are maintained at the level of individual plants and along the breeding and selection program when grown under climatic conditions (GHASEMI PIRBALOUTI & MOHAMMADI, 2013). Results (KOKKINI & VOKO 1989) indicated the major compounds of Mentha spicata (L.) grown wild in Greece, were linalool, piperitenone oxide, carvone-dihydrocarvone and pulegone- menthone-isomenthone. The compounds essential oil from aerial parts of Mentha spicata L. collected from “Tazouka” (Errachidia-Morocco) were carvone (29.00%) and trans carveol (14.00%) (ZNINI et al. 2011). MUSTAFA & BADER (2005) reported that the difference among species could be related to the variants in the alleles numbers between Mentha species, and it A.R. GOLPARVAR et al.: CHEMICAL COMPOSITION AND YIELD OF ESSENTIAL OIL OF MENTHA 1107 may be more obvious in the asexual plants M. longifolia. The genetic variability, found among the species, could be due to out-breeding and the wide dispersal of seeds and pollen grains. Divergence between M. longifolia and M. spicata could be a reflection of the impact of environmental variation among the samples of Mentha species. TALEBI KOUYOKHI et al. (2008) reported that phytochemical variations were not only found among samples of different regions but also among samples of the same region with different altitude reflecting the effect of environment on essential oil components.

Fig 1. The chromatograms found in essential oils Fig 2. The chromatograms found in essential oils of M. longifolia collected from Ardestan province of M. longifolia collected from Saman province.

Fig 3. The chromatograms found in essential oils of Fig 4. The chromatograms found in essential oils of M. longifolia collected from Kuhrang province. M. spicata collected from Ardestan province.

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Fig 5. The chromatograms found in essential oils Fig 6. The chromatograms found in essential oils of M. spicata collected from Saman province. of M. spicata collected from Kuhrang province.

CONCLUSIONS In conclusion, the results of this study provide data on variation of phytochemical characteristics of the essential oils from three ecotypes of Mentha longifolia (L.) Huds. and Mentha spicata L. The present study indicates the essential oil components of two Mentha species vary with genotype and chemotypes. Results of current study indicate that 1,8-cineole, pulegone and sabinene M. longifolia and carvone, 1,8-cineole and pulegone for M. spicata are the main constituents of the essential oils. The composition of the essential oil three ecotypes of (M. longifolia L.) and (M. spicata L.) depends on many factors of genetic, environmental and their interaction effects, such as plant part, harvest-time, extraction-method, ecotype and geographic origin (climate, edaphic, elevation and topography. Received October 09th, 2015 Accepted June 18th, 2016

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DIVERZITET HEMIJSKE KOMPOZICIJE I PRINOSA ESECIJALNOG ULJA IZ DVE VRSTE MENTE

Ahmad Reza GOLPARVAR1* i Amin HADIPANAH2

1Odeljenje agronomije i oplemenjivanja biljaka, Isfahan (Khorasgan) Branch, Islamic Azad Univerzitet, Isfahan, Iran 2 Odeljenje za horitkulturu, nauku i istraživanje, Islamic Azad Univerzitet, Tehran, Iran

Izvod Rod Mente pripada familiji nana (Lamiaceae). Prinos esencijalnih ulja iemiske komponente dve vrste Mente, Mentha longifolia (L.) Huds. i (Mentha spicata L.) skupljeni od tri ekotipa u Iranu su ispitane. Esencijalna ulja su dobijena hidro-destilacijom i analizirana gas hromatogrqafijom masenim spektrofotometrom (GC–MS). Značajne razlike (p < 0.05) u prinosu ulja su dobijene iz različitih oblasti dve vrste Mente. Prinos ulja za oblasti kod M. longifolia je bio 0.62, 0.85 i 1.24 ml / 100 g suve mase a kod M. spicata, 0.49, 1.02 i 1.54 ml / 100 g suve mase u Ardestan, Saman i Kuhrang provinciji. Rezultati ukazuju na značajne razlike (p < 0.01) za glavne komponente esencijalnog ulja iz dve vrste mente. Glavne komponente ulja M. Longifolia sakupljene iz Ardestan su pulegon (31.21%), 1,8-cineol (23.01%), sabinen (6.76%), iz Samana pulegon (31.06%), 1,8-cineol (24.34%), sabinen (7.45%) i iz Kuhranga pulegon (36.42%) i 1,8- cineol (29.49%). Glavne komponente ulja M. spicata sakupljene u provinciji Ardestan su 1,8- cineol (35.28%), karvon (30.71%), iz Saman karvon (35.37%), 1,8-cineol (24.35%), pulegon (18.67%) i Kuhrang karvon (41.51%), 1,8-cineol (25.95%). Generalno dobijeni rezultati u poređenju sa ranijim istraživanjima ukazuju na razlike u kompoziciji esecijalnih ulja i prinosu ulja što može biti povezano sa genetičkim diverzitetom dve vrste mente. Primljeno 09. X. 2015. Odobreno 18. VI. 2016.