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Chemical Constituents of Algerian Mandarin (Citrus Reticulata) Essential Oil by GC-MS and FT-IR Analysis

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Chemical Constituents of Algerian Mandarin (Citrus Reticulata) Essential Oil by GC-MS and FT-IR Analysis DOI: 10.2478/cipms-2020-0032 Curr. Issues Pharm. Med. Sci., Vol. 33, No. 4, Pages 197-201 Current Issues in Pharmacy and Medical Sciences Formerly ANNALES UNIVERSITATIS MARIAE CURIE-SKLODOWSKA, SECTIO DDD, PHARMACIA journal homepage: http://www.curipms.umlub.pl/ Chemical constituents of Algerian mandarin (Citrus reticulata) essential oil by GC-MS and FT-IR analysis Hicham Boughendjioua1* , Nour El Houda Mezedjeri2, Ilhem Idjouadiene2 1 Department of Natural Sciences, Higher School of Professors for Technological Education, Skikda, Algeria 2 Department of Biology, University of Skikda, Algeria ARTICLE INFO ABSTRACT Received 20 March 2020 Medicinal plants are potential sources of natural compounds with biological activities and Accepted 04 August 2020 therefore attract the attention of researchers worldwide. Citrus oils are a complex mixture Keywords: of more than a hundred components of differing chemical natures. Qualitative and mandarin, quantitative analysis by gas chromatography coupled with mass spectrometry (GCMS) Citrus reticulata, of the Citrus reticulata essential oil collected from El Hadaïk, Skikda City (Algeria), essential oil, gas chromatography-mass identified 28 compounds representing a total of 99.41%. The essential oil is constituted spectrometry analysis (GCMS), mainly of: D-Limonene (85.10%), Sabinene (2.49%), Linalyl acetate (2.00%), Copaene Fourier-Transform Infrared (1.80%) et α-Pinene (1.75%) totaling approximately 93.14%. The essential oil was also Spectroscopy (FTIR). analyzed by Fourier transform infrared spectroscopy analysis (FTIR). FTIR spectroscopy allowed us to identify 10 volatile compounds and indicated that the functional groups of the essential oils are C-H (Alkene), C-H (aromatic) and C=C. The obtained results have shown that the essential oil can be fully utilized for pharmacy, cosmetology and industry. INTRODUCTION The genus Citrus (Rutaceae) is one of the ancient, most composition of Citrus oils due to differences in origin, traded and most popular crops. The earliest records of its genetic background, season, climate, age, ripening stage, cultivation date back to 2100 BC [1]. The origin of Citrus is method of extraction, etc. [6-10]. Roughly 700 to 800 kg of still controversial; however, it is believed to have come from mandarin fruit is needed to produce one kilo of essential oil. Southeast Asia Mandarins that have their origin in China There are three kinds of essential oil; green, yellow and and are native to the countries of South East Asia and the red, all derived from the same fruit, but at different stages Philippines. The fruit spread through Asia, and, eventually in of maturity. Green mandarin oil is generally sharper and the 19th century, to the Western world. Today, it is cultivated with more of a “peel” note compared to red mandarin. in Mediterranean or subtropical climates around the globe. The volatile components are presented in Figure 1. Sweet There are several varieties of this fruit, including tangerines, orange, bitter orange, mandarin and grapefruit essential oils a deep orange-red hybrid species originating from Tangier are rich in monoterpenes, with the major component being and the clementine from Algeria [2]. Interestingly, essential d-limonene (65.3-95.9%) [5]. oil is the most vital by-product of Citrus processing. Citrus essential oils are broadly used as natural food additives in several food and beverage products [3] because they have been classified as generally recognized as safe (GRAS) [4]. Furthermore, Citrus essential oils are used as natural preser- vatives due to their broad spectrum of biological activities, including antimicrobial and antioxidant effects [5]. Because of their high economic importance, numerous studies have investigated the chemical composition of the peel, leaf, and flower essential oils of different Citrus species. It is worth noting that there is a great variation in the chemical * Corresponding author e-mail: [email protected] Figure 1. Chemical structures of volatile components in Citrus essential oils [11] © 2020 Author(s). This is an open access article distributed under the Creative Commons Attribution-NonComercial-No Derivs licence (http://creativecommons.org/licenses/by-nc-nd/3.0/) 197 Hicham Boughendjioua, Nour El Houda Mezedjeri, Ilhem Idjouadiene Chemical constituents of Algerian mandarin (Citrus reticulata) essential oil by GC-MS and FT-IR analysis Infrared (IR) spectrometry offers researchers and breeders ‘gasoline’, because it does not undergo any chemical modifi- an alternative approach that is robust and rapid for assessing cation [15,17]. The obtained essential oil was stocked at 4°C, essential oil content. The majority of the carbon-based mol- in the presence of anhydrous sodium sulfate, until further ecules in plants are highly active in the IR. At its simplest, analyses. mid-IR spectroscopy is a useful analytical approach in its Gas chromatography-mass spectrometry analysis own right that provides structural information on samples (GCMS) of pure compounds [12]. Spectroscopy is based on the study of the interactions The experiment was performed by using a Perkin Elmer between matter and electromagnetic radiation. This radia- Clarus 500 gas chromatographer equipped with an Elite-5 ms tion consists of a particle beam having an undulating capillary column (30 nm X 0.25 mm X 0.25 μm), as well motion. Together, all electromagnetic radiation forms the as a mass detector ‘Turbo Mass Gold’ (PerkinElmer, USA) electromagnetic spectrum. In the spectrum, four regions operating in EI mode. The column temperature was set are discernible: X-rays, ultraviolet (UV), visible and infra- at 60°C initially (maintained for 3 min), which was then red (IR). The emphasis will be on infrared (IR) spectros- increased to 160°C at a rate of 4°C/min and finally to 280°C copy because spectrum analysis in this region allows us at a rate of 10°C/min (maintained for 5 min). Injector, to follow a reaction process, determine the dosage of a interface and ion-source were kept at 270, 250 and 200°C, compound, check the purity of a product and identify an respectively. The carrier gas was helium with a constant unknown. Moreover, it is an inexpensive and easy to use flow rate of 1.0 mL/min. To the experimental conditions of process. Hence, IR spectroscopy is the most widely used the mass spectrometer, electron impact (EI+) mass spectra spectral method used by chemists. The principle is based on were recorded at 70 eV. Splitting ratio was 10:1. Scan was molecular vibrations. The energy emitted as photons can be set at 0.2 scan/s from m/z 35 to 500 amu. The samples were absorbed by the material causing vibration in the molecules. diluted in n-hexane prior to injection to obtain the appropri- This vibration changes the angle and the distance between ate peak intensity. Injection volume of the sample was 0.2 µl. the atoms. When the molecule returns to its original form, The analysis of the chemical composition of essential oil energy will be released as heat. The absorption and release by GCMS was made at the Regional Police Scientific of energy by the molecule will be recorded by the apparatus Laboratory (Constantine, Algeria). Retention indices for and translated into a band spectrum. The analysis of this all compounds were determined according to the Van den spectrum makes it possible to obtain the necessary informa- Dool approach [18], using n-alkanes (C9-C24) as standards. tion of the material analyzed [13]. Identification of the components was based on comparison The study of the physiologically active components of of their MS with those of the Wiley library and those Citrus and their contribution to human health is a growing described in the literature [19]. research field. The main objective of the present study is to Fourier-transform infrared spectroscopy analysis analyze the various phytochemical constituents of Algerian (FTIR) Mandarin (Citrus reticulata) essential oil by using GCMS and FTIR analysis, and to show the advantages of FTIR for FTIR was performed with a PERKIN ELMER (universal direct and rapid test methods. This methodology can also be ATR Sampling Accessory) apparatus, the operating con- applied to identify metabolomic indicators, and, based on ditions were as follows: technique: ATR, analysis range: their specificities, to establish a faster traceability and quality 4000-600 cm-1. The results are directly compared with those control for discrimination of Citrus reticulata essential oil. of the internal bibliography of the apparatus; 01. Euclidean, 02. PSU/peak, 03. MIX PSU, 04. Peak Match, 05. PEAK/psu, MATERIALS AND METHODS 06. MIX PEAK. The comparison was made between crude essential oil and the Limonene (standard of the Euclidean Plant material internal library). The FTIR analysis was performed at the 1488.4 g of the tested sample was obtained from a private Regional Police Scientific Laboratory (Constantine, Algeria). farm located in the region in El Hadaïk (Skikda city, North- East of Algeria). Plant harvesting was carried in October RESULTS AND DISCUSSION and December 2018. The upper part of the pericarp was harvested from fresh fruit, this choice was justified by the Chemical constituents of essential oil using GCMS richness of zest in essential oils compared to other parts We observed that minimum essential oil yield (0.1%) was of the fruit [14]. The plant was taxonomically identified at obtained when fruits were immature (during October). As the Department of Natural Sciences, High School Professors fruit samples matured, the oil yield increased. In December, Technological Education, Skikda (Algeria) by Dr. Hicham the essential oil yield rose to 0.2%. The chromatographic Boughendjioua. Specie name was according to International analyse resulted in the identification of 28 compounds repre- Plant Name Index (IPNI). senting a total of 99.41%. The essential oil of Citrus reticu- lata consists mainly of: D-Limonene (85.10%), Sabinene Isolation of the essential oil (2.49%), Linalyl acetate (2.00%), Copaene (1.80%) et The essential oils was obtained by cold expression α.-Pinene (1.75%) totaling approximately 93.14% (Table 1 (physical process).
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