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Download Full Article FARMACIA, 2020, Vol. 68, 1 https://doi.org/10.31925/farmacia.2020.1.24 ORIGINAL ARTICLE A NOVEL METHOD FOR THE EXTRACTION OF THE MAIN COMPOUNDS FROM THE ESSENTIAL OIL OF CLOVE BUDS NIKOLAY N. BOYKO ¹a,b*, ELENA T. ZHILYAKOVA ¹b, DMITRIY I PISAREV ², OLEG O. NOVIKOV ², RITA V. SAHAIDAK-NIKITIUK ³a, VICTORIA YU. KUZNIETSOVA ³b, OLEG S. SHPYCHAK 3c, ALEKSANDR V. TKACHEV 4a, ANATOLIY M. KOVALENKO 4b, NATALIA A. SUSHCHUK 5 ¹Laboratory of Technology of Drugsa, Department of Pharmaceutical Technologyb, Department of General Chemistryc, Belgorod National Research University, 85 Pobedy Street, Belgorod, Russia ²Shared Knowledge Center (Research and Educational Center) “Drugs’ quality control center” Рeoples’ Friendship University of Russia, 8/2 Miklukho-Maklay Street, Moscow, Russia ³Department of Processes and Apparatuses of Chemical and Pharmaceutical Industriesa, Department of Chemistry of Natural Compoundsb, Department of Industrial Pharmacy and Economy Institute for Advanced Training of Pharmacy Specialistsc of National University of Pharmacy, 53 Pushkinska Street, Kharkiv, Ukraine 4Department of General and Private Zootechnicsa, Department of Infectious and Invasive Pathologyb, Belgorod State Agricultural University named after V. Gorin, Federal State Budgetary Educational Institution of Higher Education, 3 Vavilova Street, Belgorod, Russia 5Department of Technology of Drugs, Odessa National Medical University, 2 Valikhovsky Lane, Odessa, Ukraine *corresponding author: [email protected] Manuscript received: July 2019 Abstract The purpose of this work was to test a hypothesis about the possibility of extraction of the main clove buds essential oil substances from with two different types of perfluoro organic solvents, Novec 1230 and Novec 7100. Using simple maceration method, it was found out that the maximum yield of eugenol was observed into n-hexane: 81 ± 4%. The yield of eugenol into perfluoro organic solvent Novec 7100 was 73 ± 4% and into the perfluoro organic solvent Novec 1230 was 6.9 ± 0.4%. Using the extraction circulation method, it was found that the yield of eugenol into perfluoro organic solvent Novec 7100 in 2 h of circulation was 85 ± 4%. Under the same conditions, the yield of eugenol into the perfluoro organic solvent Novec 1230 was 54 ± 3% during 4 h of its circulation. Rezumat Scopul acestei lucrări a fost de a testa ipoteza cu privire la posibilitatea extracției substanțelor principale din uleiul esențial de cuișoare cu două tipuri diferite de solvenți organici, Novec 1230 și Novec 7100. Folosind metoda macerării simple, s-a constatat că randamentul maxim de obținere a eugenolului a fost în n-hexan: 81 ± 4%. Randamentul de obținere a eugenolului în solventul organic perfluoric Novec 7100 a fost de 73 ± 4% și cel în Novec 1230 a fost de 6,9 ± 0,4%. Utilizând metoda extractivă de circulație, s-a constatat că randamentul eugenolului în solventul organic perfluoric Novec 7100, în 2 ore de circulație, a fost de 85 ± 4%. În aceleași condiții, randamentul eugenolului în solventul organic perfluoric Novec 1230 a fost de 54 ± 3% în timpul a 4 ore de circulație. Keywords: eugenol, clove buds, Novec 1230, Novec 7100 Introduction Caryophyllus aromaticus L. tree is a perennial and Biologically active substances (BAS) from clove buds evergreen plant that belongs to Myrtaceae family. have different useful pharmacological activities such Clove buds are plant raw material (PRM) used in as analgesic, anti-ulcerogenic, antiinflammatory, anti- medicinal, perfume, food and liquor industries. microbial, antifungal, antioxidant, antitumor, anti- The main constituents of clove buds are essential oil diabetic, cardioprotective, hepatoprotective, etc. [1, 2, up to 20% (eugenol up to 85%, eugenyl acetate up to 13, 14, 16-18, 20, 24]. Furthermore, some biologically 15%, caryophyllene up to 4%, etc.), galotanins up to active substances exhibit low toxicity [2, 14, 23]. 2%, flavonoids (derivatives of quercetin, eugenitin, Therefore, one of the promising areas of focus for eugenin, biflorin, myricetin, etc.), phytosterols (campesterol, the development of drugs from this type of PRM is stigmasterol), triterpenic saponins (crategolic and oleanolic the development of galenical drugs in the form of a acids), microelements, etc. [12, 13, 17]. tincture or an extract [13, 14]. Another promising area of focus is a step-by-step treatment of PRM and the 170 FARMACIA, 2020, Vol. 68, 1 obtainment of lipophilic and hydrophilic extracts from expensive equipment that can perform under pressure it. The treatment of PRM with liquefied gases and and the use of a refrigerator. liquids in the supercritical state (supercritical fluids) is In the light of the research, we focused our attention considered to be a very promising technology all over on unique physical and chemical properties of some the world [5, 8, 9, 11, 15, 19]. Moreover, extraction freons and perfluoro organic solvents, for example, of essential oil and eugenol from clove buds with perfluorocyclobutane (RC318). Freons and perfluoro supercritical fluids (in general, carbon dioxide) organic solvents have the lowest values for key and and/or liquefied gases have been successfully important physical and chemical parameters, such as studied by different scientists [6, 9, 12, 15, 25]. heat of vaporization, surface tension, the boiling point. The main advantages of these technologies are the They are fire and explosion-proof, as well as low- following: minimal temperature, it can be organized toxic. But the most important thing is that these step-by-step extraction of various types of BAS with solvents are characterized by hydrophobicity of various different polarity, environment-friendly, fire and degree and even lipophobicity [10, 11, 22]. Physico- explosion-proof, they require minimal energy [7, 10, chemical, ecological, and toxicological parameters of 11]. At the same time, these technologies have certain some perfluoro organic solvents and liquefied gases disadvantages: they require the use of special and are presented in Table I [10, 11, 22]. Table I Physicochemical, ecological, and toxicological parameters of some perfluoro organic solvents and liquefied gases Solvent Parameter Novec Novec Vertrel XF Novec 7200 Perfluorohehane R227еа RC318 CO2 1230 7100 (HFC 43-10 mee) Empirical formula С6F12O C4F9OСH3 C4F9OС2H5 C5H2F10 C6F14 C3F7Н cC4F8 СО2 Molecular weight, g/mol 316 250 264 252 338 170 200 44 Pressure 20°С, МPa 0.040 0.027 0.016 0.030 - 0.391 0.272 6.0 Boiling point, °С 49 61 76 55 57 -16.4 -5.8 -78.5 Heat of vaporization, kJ/kg 88 112 119 130 91 133 117 155 Density 20°С, kg/m³ 1,600 1,510 1,430 1,580 1,670 1,407 1,517 930 Global warming potential 1 320 55 1,650 7,400 - 9,300 3,300 10,300 1 (GWP) Ozone depletion potential 0 0 0 0 0 0 0 0 (ODP) Toxicity, ppm 4,000 750 - 200 71 1,000 1,000 5,000 As presented in Table I, among different types of Materials and Methods perfluoro organic solvents, two of them (Novec Plant raw material 1230 and Novec 7100) have promising physicochemical, For the study, we used milled clove buds with the ecological, and toxicological parameters. particle size ranging from 0.1 to 0.5 mm. PRM was These properties are determined by the presence of acquired from “Lechec”, Kharkiv, Ukraine; it is dated a special type intermolecular fluorine bond between 08/2018. perfluoro organic molecules [3]. Chemicals Lipophobic properties in perfluoro organic solvents Novec 1230, Novec 7100 (3M company, USA), described in literature gave us the idea that these and n-hexane (chemically pure grade, Component- solvents may be used in phytotechnology for selective Reactive, Russia) were used as solvents. As a reference extraction of essential oils’ components from the substance, we used eugenol Sigma-Aldrich, Merck, essential oil-bearing PRM [9]. Moreover, their use can content ≥ 99.0%, CAS 97-53-0. be a good alternative for technology using liquid gases Methods of extraction and/or supercritical fluids (presented in Table I). Simple maceration was carried out under the following Thus, studies in the field of perfluoro organic solvents’ conditions: 1.0 g of milled PRM (precisely weighed use for extraction of different lipophilic BAS and amount) was placed into a flask, then we added essential oils, in particular, are rather pressing. 10.0 mL of solvent and weighted for better accuracy, The purpose of this work was to test a hypothesis and then the flask was corked and macerated at 24 ± about the possibility of extraction of main essential 1°С for 24 h. After maceration, the extract was oil substances from clove buds with two different decanted and centrifuged at 3,000 rpm for 10 min. types of perfluoro organic solvents, Novec 1230 and The circulation method of extraction was carried out Novec 7100. under the following conditions: 5.0 g of milled PRM (precisely weighed amount) was placed into the Soxhlet extractor, then 25.0 mL of the solvent were added, 171 FARMACIA, 2020, Vol. 68, 1 and the process of solvent circulation was carried out Ultra with a mass analyser, by Shimadzu, Japan. for a specified period. Column: Zebron ZB-5MS, length 30 m, inside The solvent was evaporated on the water-bath at 65°C, diameter 0.25 mm, film thickness 0.25 μm; liquid and the extract obtained was dissolved in 10.0 mL of phase: 5%-polysilarylene and 95-polydimethyl-siloxane; ethyl acetate weighted for better accuracy and analysed temperature settings: from 70°С to 325/350°С. Gas- for a non-volatile residue of lipophilic substances by carrier: helium with a stable flow of 3.0 mL/min. gravimetry and for eugenol content by reverse phase Detection regimen: total ion current (SCAN) in the high performance liquid chromatography (RP HPLC) range m/z from 30 to 500 Da with scanning velocity analysis. 1,000 and result time 0.5 sec. The injection volume was The content of non-volatile residue of lipophilic 1 µL.
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