Aćimović et al., 2019, Biologica Nyssana 10(1) 10 (1) September 2019: 23-28 DOI: 10.5281/zenodo.3463994 The chemical composition of the essential oil of Dracocephalum moldavica L. from Vojvodina Province (Serbia) Original Article Milica Aćimović Institute of Field and Vegetable Crops Novi Sad, Maksima Gorkog 30, 21000 Novi Sad, Serbia acimovicbabicmilica@gmail.com (corresponding author) Jovana Stanković Institute of Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Serbia jovana_stankovic@hotmail.com Mirjana Cvetković Institute of Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Serbia miracvet13@gmail.com Marina Todosijević University of Belgrade, Faculty of Chemistry, Stu- dentski trg 12-16, 11000 Belgrade, Serbia marinab@chem.bg.ac.rs Milica Rat University of Novi Sad, Faculty of Science, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia milica.rat@dbe.uns.ac.rs Received: Mart 7, 2019 Revised: May 21, 2019 Accepted: August 26, 2019 Abstract: Dracocephalum moldavica L., also called Moldavian balm or Moldavian dragonhead, is native to temperate climate of Asia, but it was naturalized in Eastern and Central Europe, North Africa, China and north-eastern United States. This is an annual plant, with numerous stems (up to 6), 22-45 cm high, and blue flowers arranged in pseudo-whorls growing in leaf axils. Essential oil accumulates in exogenous oil-containing cells at the dor- sal sides of the leaves, and in the inflorescence. Because of this, the entire plant has a citrus-like flavor, resembling that of lemon balm and catnip. This plant is extensively used as a spice and for composition of tea blends, in food aromatization (canned fish, jams, candies, syrups), perfumery, al- cohol industry, soaps and detergents. Dracocephalum moldavica from Vojvodina Province, Serbia contains geranial (29.6%), geranyl acetate (27.2%) and neral (19.4%) as the most abundant compounds. Further inves- tigations will be focused on the influence of weather conditions on essen- tial oil composition, as well as on bioactive potential of this essential oil. Key words: Moldavian balm, Moldavian dragonhead, GC-MS analysis, geranial, geranyl acetate, neral Apstract: Hemijski sastav etarskog ulja Dragocephalum moldavica L. iz Vojvodine (Srbija) Biljka Dracocephalum moldavica L., poznata je kao Moldavska melisa ili Moldavska zmajeglavka. Poreklom je iz umerenog klimata Azije, ali je naturalizovana u Istočnoj i Centralnoj Evropi, Severnoj Africi, Kini i severo-istočnom delu SAD. Iz korena ove jednogodišnje biljke izbija veći broj stabljika (do 6), koje su 22-45 cm visine, sa plavim cvetovima raspoređenim u lažnim pršljenastim cvastima u pazusima listova. Etarsko ulje se akumulira u egzogenim uljanim ćelijama sa donje strane listova i u cvetovima. Zbog etarskog ulja koje ima citrusnu notu ova biljka podseća na matičnjak i macinu travu. Biljka se intenzivno koristi kao začin i kao dodatak čajnim mešavinama, za aromatizaciju hrane (konzervirana riba, džemovi, slatkiši, sirupi), parfimeriji, alkoholnoj industriji, proizvodnji sa- puna i deterdženata. Etarsko ulje D. moldavica iz AP Vojvodine, Srbije sadrži geranial (29,6%), geranil-acetat (27,2%) i neral (19,4%) kao najzas- tupljenije komponente. Dalja istraživanja biće usmerena na uticaj vremen- skih uslova na sastav etarskog ulja, kao i na njegov biološki potencijal. Ključne reči: Moldavska melisa, Moldavska zmajeglavka, GC-MS analiza, geranial, geranil acetat, neral Introduction Dracocephalum moldavica L., also called Molda- vian balm or Moldavian dragonhead, is native to temperate climate of Asia, but it was naturalized in Eastern and Central Europe, North Africa, China and north-eastern United States. This species belongs to the subtribe Nepetinae, tribe Menthae of Lamiaceae family. The genus contains 71 species, widespread across Northern Hemisphere regions (Naderifar et al., 2015; Amirnia et al., 2017). This annual plant is very beautiful, with numer- ous stems (up to 6), 22-45 cm high, and blue flow- ers arranged in pseudo-whorls growing in leaf axils. © 2019 Aćimović et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and build upon your work non-commercially under the same license as the original. 23 Essential oil accumulates in exogenous oil-contain- ing cells at the dorsal sides of the leaves, and in the inflorescence. Because of this, the entire plant has a citrus-like flavor, resembling that of lemon balm (Melissa officinalis L.) and catnip (Nepeta cataria L.). Apart from essential oil, the plant produces nec- tar, due to which it is grown as a honey-bearing plant and cultivated in gardens and parks as an ornamental plant (Aćimović et al., 2019). This plant with its citrus like flavor is extensively used as a spice and for composition of tea blends, because of neral and geranial as major constituents of essential oil. Dracocephalum moldavica is used in food aromatization (canned fish, jams, candies, syrups), perfumery, alcohol industry, soaps and detergents. Apart from this, dried leaves have the potential of being used as a functional additive for extruded crisps with high nutritional value, especial- ly because of the dietary fiber and rosmarinic acid content, strong antioxidant potential and acceptable sensory properties (Wojtowicz et al., 2017). Seed is a good source of fatty oil with spicy taste and aromatic odor, rich in unsaturated fatty acids, principally the linolenic and linoleic acids. This cat- egorizes D. moldavica seed into the group of raw materials suitable for nutraceuticals, food supple- ments, and functional food applications (Aćimović et al., 2019). Moreover, the application of D. mol- davica residues as bagasse waste (oilcake) collected after pressing and added to corn crisps could be an effective way of limiting the oil waste after pressing and increasing the sustainability of waste manage- ment. A new range of nutritionally valuable snacks could be introduced to the market (Oniszczuk et al., 2017). Furthermore, numerous investigations show that this plant possesses good antioxidative (Aprotosoaie et al., 2016; Aslanipour et al., 2017; Weremczuk- Jeżynaet al., 2017; Ehsani et al., 2017; Fallah et al., 2018), antimicrobial (Pak et al., 2016; Ehsani et al., 2017; Keikhaie et al., 2018) and insecticidal activity (Chu et al., 2011; Ding et al., 2015). It is also used as antinociceptive (Maham et al., 2013), sedative (Mar- tínez-Vázquez et al., 2012), neuroprotective (Sun et al., 2014), as well as cardiotonic agent (Najafi et al., 2009; Zeng et al., 2018), and for treating chronic mountain sickness (Maimaitiyiming et al., 2014). This species is not well known in Serbia. It was introduced in Serbia in the collection garden of In- stitute of Field and Vegetable Crops, from Romania (Kišgeci et al., 1982). The aim of this paper is to analyze the essential oil obtained from D. moldavica grown in agroecological conditions of Vojvodina Province, Serbia. Materials and methods Plant material The plant (Fig. 1) grown at Institute of Field and Vegetable Crops Novi Sad, during 2018, were con- firmed by M. Rat and deposited at the Herbarium of Biology and Ecology (BUNS herbarium), Faculty of Natural Sciences, University of Novi Sad, as D. moldavica, Voucher specimens 2-1468. During the flowering stage (June), the aboveground parts were cut, dried and used for essential oil extraction. Essential oil extraction The dried aboveground parts of D. moldavica were subjected to hydro-distillation using an all glass Clevenger-type apparatus to extract essential oils. The samples were ground, homogenized and made into a fine powder. In order to extract the essential oils, 100 g of the powder was placed in 1 l coni- cal flask and connected to the Clevenger apparatus. 500 ml of distilled water was added to the flask and heated to the boiling point. The steam in combina- tion with the essential oils was distilled into a gradu- ated cylinder for 4 h and then separated from aque- ous layer. The yield essential oil was very low, so it is extracted with n-hexane, dried over anhydrous sodium sulfate and evaporated. The obtained oil was kept refrigerated at +4 °C until required for further analysis. 24 BIOLOGICA NYSSANA ● 10 (1) September 2019: 23-28 Aćimović et al. ● The chemical composition of the essential oil of Dracocephalum moldavica L. from Vojvodina Province (Serbia) Fig. 1. Dracocephalum moldavica GC/MS analysis Gas chromatographic-mass spectrometric analysis was performed using an Agilent 6890 gas chromato- graph coupled with an Agilent 5973 Network mass selective detector (MSD) (both Agilent, Santa Clara, USA), in positive ion electron impact (EI) mode. The separation was effected using Agilent 19091S-433 HP-5MS fused silica capillary column with 30 m × 0.25 mm i.d., 0.25 μm film thickness. The GC oven temperature was programmed from 60 °C to 285 °C at a rate of 3 °C/min. Helium was used as carrier gas; inlet pressure was 20.3 kPa; linear velocity was 1 ml/ min at 210 °C. Injector temperature: 250 °C; injec- tion mode: splitless. MS scan conditions: MS source temperature, 230 °C; MS Quad temperature, 150 °C; energy, 70 eV; mass scan range, 40–550 amu. 25 Identification of volatile compounds The identification of components was carried out on the basis of Kovats retention index and by compari- son with reference mass spectra (Wiley and NIST databases). Results and discussion In D. moldavica essential oil 88 compounds were detected, among which geranial (29.6%), geranyl acetate (27.2%) and neral (19.4%) were the most abundant, comprising 76.2%. Other significant com- pounds were: geraniol (5.4%), neryl acetate (3.0%), piperitone (1.8%) and vulgarone B (1.6%). Other compounds were present in the amount less than 1.0%, among which 31 unidentified compounds Table 1. Chemical composition of D. moldavica No Compound RI Rt % No Compound RI Rt % 1 1-Octen-3-ol 982 7.14 0.2 46 trans-α-Farnesene 1514 29.23 tr 2 3-Octanone 990 7.38 0.2 47 Italicene ether 1540 30.28 tr 3 dehydro-1,8-Cineole 997 7.59 tr 48 Spathulenol 1582 32.032 0.2 4 3-Octanol 1000 7.65 0.1 49 Caryophyllene oxide 1587 32.25 0.4 5 Bergamal 1057 9.70 0.1 50 Viridiflorol 1596 32.60 tr 6 cis-Linalool oxide 1076 10.42 tr 51 Salvial-4(14)-en-1-one 1598 32.67 tr 7 trans-Linalool oxide 1093 11.04 tr 52 NI-12 1602 32.88 0.1 8 Linalool 1104 11.47 0.4 53 NI-13 1610 33.17 0.1 9 NI-1 1109 11.65 0.1 54 Humulene epoxide II 1613 33.28 0.1 10 1-Octen-3-yl acetate 1116 11.98 tr 55 1,10-di-epi-Cubenol 1619 33.51 tr 11 NI-2 1142 13.10 0.1 56 NI-14 1630 33.93 0.1 12 exo-Isocitral 1148 13.34 0.1 57 NI-15 1634 34.09 0.1 13 trans-Chrysanthemal 1152 13.54 0.3 58 NI-16 1648 34.63 0.1 14 Nerol oxide 1156 13.76 0.1 59 Vulgarone B 1654 34.87 1.6 15 cis-Isocitral 1166 14.18 0.6 60 NI-17 1659 35.02 0.1 16 NI-3 1175 14.59 0.2 61 cis-Calamenen-10-ol 1663 35.20 0.1 17 Rosefuran epoxide 1177 14.62 0.1 62 NI-18 1668 35.37 0.1 18 trans-Isocitral 1184 14.96 0.9 63 NI-19 1675 35.67 0.2 19 α-Terpineol 1193 15.34 tr 64 Germacra-4(15),5,10(14)-trien-1-α-ol 1690 36.25 0.1 20 NI-4 1196 15.50 0.2 65 Cyclocolorenone 1764 38.92 0.1 21 NI-5 1209 16.01 0.2 66 NI-20 1829 41.28 0.1 22 NI-6 1222 16.57 0.1 67 6,10,14-Trimethyl-2-pentadecanone 1851 42.02 0.3 23 NI-7 1226 16.77 0.1 68 NI-21 1926 44.59 0.1 24 Nerol 1232 17.04 0.4 69 NI-22 2011 47.47 0.1 25 NI-8 1236 17.22 0.2 70 NI-23 2038 48.29 0.1 26 Neral 1248 17.76 19.4 71 Manool 2068 49.18 0.1 27 Piperitone 1258 18.21 1.8 72 NI-24 2082 49.60 0.1 28 Geraniol 1262 18.38 5.4 73 NI-25 1997 50.02 0.1 29 NI-9 1264 18.48 0.2 74 NI-26 2116 50.62 0.1 30 Geranial 1280 19.18 29.6 75 NI-27 2126 50.91 0.3 31 trans-Anethole 1291 19.65 tr 76 NI-28 2156 51.80 0.2 32 Thymol 1298 19.96 tr 77 NI-29 2164 52.05 0.2 33 Carvacrol 1307 20.35 0.7 78 NI-30 2218 53.65 0.1 34 Methyl geranate 1328 21.26 0.2 79 NI-31 2238 54.26 0.1 35 Neryl acetate 1369 23.08 3.0 80 Tricosane 2307 56.54 0.1 36 α-Copaene 1380 23.58 0.1 81 Pentacosane 2503 62.04 0.2 37 Geranyl acetate 1393 24.15 27.2 82 Hexacosane 2603 64.65 tr 38 Decyl acetate 1412 25.07 0.1 83 Heptacosane 2706 67.19 0.3 39 trans-Caryophyllene 1425 25.49 0.2 84 2-methyloctacosane 2780 68.96 tr 40 α-Humulene 1459 26.91 0.1 85 Octacosane 2806 69.60 tr 41 NI-10 1464 27.11 0.1 86 Nonacosane 2906 71.96 0.3 42 NI-11 1469 27.35 0.1 87 Triacontane 3056 74.23 tr 43 Germacrene D 1488 28.10 0.1 88 Untriacontane 3105 76.45 0.1 44 ar-Curcumene 1489 28.15 0.1 TOTAL IDENTIFIED 95.5 45 trans-β-Ionone 1491 28.24 tr TOTAL NI 4.1 RI – retention Index, Rt – Retention time, NI – not identified compounds (mass spectrum of these compounds, m/z (intensity) are shown at figures 2-32), tr – compound presented in traces (less than 0.1%) BIOLOGICA NYSSANA ● 10 (1) September 2019: 23-28 Aćimović et al. ● The chemical composition of the essential oil of Dracocephalum moldavica L. from Vojvodina Province (Serbia) 26 comprising 4.1% (Tab. 1). A GC-FID chromato- gram of D. moldavica essential oil is shown at Fig 2. Chemical composition of D. moldavica essen- tial oil was previously studied in Egypt (Hussein et al., 2006; El-Baky and El-Bsroty, 2008; Aziz et al., 2013; Ahl et al., 2015; Hegazy et al., 2016), Iran (Omidbaigi et al., 2010; Maham et al., 2013, Gol- parvar et al., 2016, Ehsani et al., 2017; Janmoham- madi et al., 2017; Fallah et al., 2018), Turkey (Es- han et al., 2014), Ukraine (Kotyuk and Rakhmetov, 2017) and China (Chu et al., 2011). It is established that chemical composition of essential oil from aer- ial parts of D. moldavica depends on many factors, among which origin, cropping system, fertilization, salt stress, weed management, etc. (Aziz et al., 2013; Janmohammadi et al., 2017; Fallah et al., 2018). The principal compounds in almost all essential oils are neral, geranial, geranyl acetate and geraniol. However, the content of neral in essential oil varied between 10.25 and 43.49%, while geranial ranged between 9.10 and 42.45%. Furthermore, geranyl acetate and geraniol content varied in larger scale, between 0.20%-40.40%, and 0.50 and 28.14%, re- spectively (Aćimović et al., 2019). Investigations show that the geranyl acetate, geranial and geraniol in essential oil reach their max- imum levels during the flowering, while the content of neral, decreases during flowering. These obser- vations indicate that the biosynthesis of geranyl ac- etate is dominant at the beginning of the vegetative period, but is superseded by biosynthesis of geranial and geraniol, from the early stage of flowering. It indicated that the optimal harvest time proved to be during the flowering stage, when the oil content is the highest and thus also the amount of the main ter- penes is the highest (Holm et al., 1988). 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