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Chromatographic Separation and Identification of Some Volatile Oils, Organic Acids and Phenols from the Seeds of Cuminum Cyminum Growing in Iraq

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Chromatographic Separation and Identification of Some Volatile Oils, Organic Acids and Phenols from the Seeds of Cuminum Cyminum Growing in Iraq IJRRAS 19 (1) ● April 2014 www.arpapress.com/Volumes/Vol19Issue1/IJRRAS_19_1_05.pdf CHROMATOGRAPHIC SEPARATION AND IDENTIFICATION OF SOME VOLATILE OILS, ORGANIC ACIDS AND PHENOLS FROM THE SEEDS OF CUMINUM CYMINUM GROWING IN IRAQ Fanar Hashum Yousif Al-Hashemi Department of Horticulture & Landscape Design College of Agriculture and Forestry, University of Mosul, Iraq E-mail: [email protected] ABSTRACT The current study was carried out for separation and identification of some active constituents from Cuminum cyminum fruit (often called seeds) were collected in unripe, fully ripe stage and investigated of these essential oils (Octanol, Limonene, Thymol, Anisyl alcohol, Cuminaldehyde, Anethole, Vanillin and also Benzoic acid), organic acids (Aspartic, Citric, Malic, Tartaric, Propionic, Ascorbic, Oxalic, Maleic and Fumaric acids) and phenols (Salicylic acid, Gallic acid, Cinnamic acid, Hydroquinone, Resorcinol, P-hydroxybenzoic acid, Rutin, Coumarine, Quercetin). The essential oils were investigated by Gas Liquid Chromatography (GLC), while quantitative identification of individual target organic acids and phenolic compounds were achieved by high-performance liquid chromatography (HPLC). Moreover the high percentage oil (10.97%) and the major components were presented as Cuminaldehyde (14.27%), Vanillin (2.76%) and Anethole (1.93%) in the fully ripe stage of seeds. Also the essential oil was studied for its physical properties. Many organic acids were identified in fully ripe seeds in eight compounds comparative with unripe seeds. Salicylic and gallic acids were showed with a highest amounts in both stage of harvest seeds. Key words: Cuminum cyminum, volatile oils, organic acid, phenols, GLC, HPLC. 1. INTRODUCTION Cuminum cyminum L. is an annual plant of the family apiaceae, native from the east Mediterranean to east India, The word cumin in English is derived from the Latin cuminum, which it self was derived from Greek "Kyminon" (Nitin et al., 2012). It is widely cultivated in Pakistan, Egypt, Iraq, Turkey, Syria, Sudan (Jalali et al., 2007). Seeds of Cuminum cyminum are carminative, aromatic, stomachic, stimulant, astringent and cooling in effect, cumin seed oil is used as multifunctional luminescent paints or in topical clothing ointment, cumin oil effects on carcinogen- metabolizing enzymes and acid sol sulpfhyd ryls in liver it is also synergistic (Hanif et al., 2012). The cumin seeds is contained volatile oil (2-5%) and the yellow coloured fresh oil contains Cuminaldehyde as its chief components (El- Kani et al., 2007). To achieve a better separation of the main organic acids (citric, lactic, formic, acetic, propionic and butyric) from dairy products various HPLC methods have been reported by (Pelin and Cevdet, 2010). A number of phenolic compounds were isolated from Cuminum cyminum including phenolic acids, flavonoids, phenolic diterpenes, in this plant are closely associated with their antioxidant activity, they are also known to play an important role in stabilizing lipid peroxidation and to inhibit various types of oxidizing enzymes (Gallo et al., 2010). When cumin seeds are harvested at different times, their physical and chemistry properties may change considerably. The aim of this study is investigated the composition of cumin oil at different periods times using GLC analysis and to identify of many organic acids and phenolic compounds using HPLC method. 2. MATERIAL AND METHODS PLANT MATERIAL: C. cyminum seeds were obtained from a local market in mosul and cultured in pots about (15 cm in diameter) in plastic house of the Department of Horticulture and Landscape Design/ College of Agriculture and Forestry – University of Mosul/ Iraq. The seeds were cultured in 15 November 2012 and collected in two periods time (unripe and fully ripe) at 3 week intervals during the harvest season in 2012. The dried seeds in lab temperature were stored in a dark place until use. CLASSIFICATION OF C. CYMINUM: The plant was classified by Mr. Tallal Taha that he is the director of medicinal plant project – Mosul dam, show the classification according to APG system III, 2009 in (Figure 1). 80 IJRRAS 19 (1) ● April 2014 Al-Hashemi ● Chromatographic Separation & Identification of Volatile Oils Kingdom : Plantae Division : Magnoliophyta Class : Magnoliopsida Order : Apiales Family : Apiaceae Genus : Cuminum Species : Cuminum cyminum L. Figure (1): Classification of Cuminum cyminum according to APG system III, 2009. EXTRACTION OF ESSENTIAL OIL Essential oil was extracted by steam distillation using any apparatus of Clevenger type. The extraction took 3hrs. for mixing 25g of seeds in each stage in 500ml of distilled water, according to the procedure as described in the British pharmacopeia (1980). After distillation the aqueous phase was extracted with diethyl ether (3x20ml). the organic phase was extracted with sodium sulphate, and eliminated by pressure distillation reduced in rotary evaporator at 35°C and pure oil was stored at 4°C in obscurity until the beginning of analysis. The physical characteristics of the cumin oil were studied i.e., percentage ratio of oil, Density, specific gravity, refractive index and colour (Guenther, 1972). Chemical composition of essential oil of Cuminum cyminum L. was analyzed by Gas liquid chromatography (Satish Kumar, 2010) using analytical conditions in Table (1), Fig. 2(A). The individual standard was also run under the same conditions. Table (1): The analytical conditions of volatile oils for GLC analysis Properties Analytical conditions Primary temp. of column 100°C Final temp. of column 300°C Average height of temp. 10°C/min Detector temperature 325°C Flow rate of He 20 ml/min Column (Length × Internal dimeter) 3% SE-30 Liquid phase 3m×1/8" Solid phase Teflon (Mesh 100-120) Attenuation 1mV Detector type (FID) Flame ionization detector SOXHLET EXTRACTION: Soxhlet extraction was carried out with standard apparatus for 8hrs. by using 25g of seeds with 200ml of hexane (El- Kani et al., 2007) to achieve defatted depending upon to method (Harborne, 1973). EXTRACTION OF ORGANIC ACIDS: The seeds of C. cyminum L. (25g) were re-extracted with 200ml of absolute ethanol by using magnetic stirrer for 72 hrs. at 60°C. The mixture is filtered and completed to 10ml in a volumetric flask with ethanol (Grand et al., 1988). The samples was prepared by using acid hydrolysis with 1N HCL for 1hr in bath water at 100°C and then the mixture was separation by using ethyl acetate when was added to solution, two layer was shown, the ethyl acetate layer was kept for other analysis. The compounds Fig. 2 (B) that containing in ethyl acetate were identified by HPLC – technique (Harborne, 1973). INSTRUMENTATION AND ANALYTICAL CONDITIONS: HPLC analysis was using a liquid chromatography (Shimadzu, LC 2010 A/Japan), the column was C18 (4.6×150)mm, at a flow-rate 1ml/min, injection volume was 20 μl, the mobile phase consisting of 40 mM Na2SO4 and the PH was adjusted at 2.68, the column temperature was 30°C, UV absorbance at 210 nm (Dionex, 2004). EXTRACTION OF PHENOLIC COMPOUNDS: After the extraction by hexane, the seeds of C. cyminum (25g) were re-extracted with 200ml of absolute ethanol by using soxhlet apparatus for 72hrs. at 78°C. The extract was filtered and evaporated under vacuum in a rotary evaporator at 65°C until 20ml. The crude extract after evaporated was carried out for acid hydrolysis (Harborne, 81 IJRRAS 19 (1) ● April 2014 Al-Hashemi ● Chromatographic Separation & Identification of Volatile Oils 1973). While the phenolic compounds were extracted with (2×25ml) ethyl acetate. The compounds were confirmed by using HPLC-technique Fig. 2 (C). INSTRUMENTATION AND ANALYTICAL CONDITIONS: HPLC analysis was performed by using a liquid chromatography (Shimadzu, LC 2010 A/Japan), the column was C18 (4.6×240)mm, at a flow-rate 1.3ml min-1, injection volume was 50 μl, the mobile phase consisting of acetonitrile:water (80:20) vlv, the column temperature was 40°C, UV absorbance at 280 nm (Al-Tkay, 2012). STOCK AND STANDARD SOLUTIONS: The volatile oils, organic acids and phenols, 0.1g were accurately weighed into volumetric flask, dissolved in diethyl ether for volatile oils and in ethanol for organic acids and phenols. CHO CHO CH CH CH3 CH3 CH2OH OH OCH3 H C Ch OH OCH3 3 2 OCH3 Cuminaldehyde Thymol Vanillin Anethole Limonene Anisyl alcohol A: Chemical structures of volatile oils OH O OH OH OH C C OH HO O O O OH O Oxalic acid O OH Malic acid OH Tartaric acid CH2OH O O H C C O HO C OH OH O OH OH Ascorbic acid Fumaric acid B: Chemical structures of organic acids COOH OH CH=CHCOOH OH COOH HO OH HO O OH OH OH HO OH OH OH H ydroquinon OH O Resorcinole Cinnamic acid Quercetin Salicylic acid Gallic acid C: Chemical structures of phenolic compounds Figure (2): The chemical structure of active constituents in Cuminum cyminum. RESULTS AND DISCUSSION PHYSICAL PROPERTIES OF CUMIN OIL: The greatest oil present was 10.97% of cumin seeds, Density and specific gravity reached 0.9023g/cm3 and 0.8329 respectively in the harvesting stage (fully ripe) while the refractive index was 1.3720 comparative with the unripe seeds Table (2). 82 IJRRAS 19 (1) ● April 2014 Al-Hashemi ● Chromatographic Separation & Identification of Volatile Oils Table (2): physical properties of C. cyminum oil Harvesting Density Specific Refractive Oil % Colour stage g/cm3 gravity index Unripe 6.64 0.8892 0.8100 1.3210 Light brownish yellow Fullyripe 10.97 0.9023 0.8329 1.3720 The physical properties of C. cyminum oil have been studied in the seeds in the recently review (Hanif et al., 2012). ESSENTIAL OIL CONSTITUENTS: Many standards of volatile oil was injected by GLC technique Fig. (3). The major components in the samples were identified as Cuminaldehyde (14.27%) followed by vanillin (2.76%) and Anethole (1.93%) in the oil of fully ripe seeds Table (3) and Fig. 4 (A).
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