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Journal of Drug Delivery and Therapeutics

Open Access to Pharmaceutical and Medical Research

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Open Access   Full Text Article                                                                                                                                                Research Article 

Phytochemical Screening, GCMS, FTIR profile of Bioactive Natural Products in the methanolic extracts of Cuminum cyminum seeds and oil

Ramya S. ¹, Loganathan T. ², Chandran M. ³, Priyanka R.³, Kavipriya D.⁴, Grace Lydial Pushpalatha G.⁵,        Aruna Devaraj⁶, Ramanathan L.⁷ and Jayakumararaj R.⁷*, Saluja Vikrant⁸

¹ PG Department of Zoology, Yadava College (Men), Thiruppalai - 625014, Madurai, TamilNadu, India

² Department of Plant Biology & Plant Biotechnology, LN Government College (A), Ponneri, TN, India

³ Department of Zoology, Thiruvalluvar University, Serkadu, Vellore-632 115, TamilNadu, India

⁴ Department of Zoology, Arignar Anna Government Arts College (W), Walajapet-632 513, TN, India

⁵ PG Department of Botany, Sri Meenakshi Government Arts College, Madurai-625002, TN, India

⁶ Rajendra Herbal Research Training Centre, Periyakulam Theni, TamilNadu, India

⁷ Department of Botany, Government Arts College, Melur – 625106, Madurai, TamilNadu, India

⁸ Faculty of Pharmaceutical Sciences, PCTE Group of Institutes, Ludhiana, Punjab, India

 

 

INTRODUCTION 

Drug development is a complicate, risky, and time-consuming process that can be divided into several stages, including disease-related genomics, target identification/ validation, lead discovery/ optimization, preclinical/ clinical trials¹. During early stages of drug discovery, activities and specificities of candidate drug lead molecule is assessed at an early stage pharmacokinetics and late stage toxicity². Practically, most of the time, withdrawal of a proven candidate drug lead in the final stage is ascribed to some undesirable efficacy/ safety in absorption, distribution, metabolism, excretion and toxicity (ADMET)^2,3. 

Cook et al.⁴ comprehensively reviewed the results of AstraZeneca's small-molecule drug projects from 2005 to 2010 based on a longitudinal study and pointed out that unacceptable safety and toxicity were the most important reasons for the failure of more than half of all projects. As with the development of drug discovery, it was realized that it is important to filter and optimize the ADMET properties for drugs at an early stage, which has been accepted and widely used to reduce the attrition rate in drug research and development. A Fail-Early-Fail-Cheap strategy is employed by many of the pharmaceutical companies⁵. 

Pharmacokinetics and toxicity assessments of preclinical drugs are of significant value in reducing failure rate of new chemical entities in clinical trials^6-8. In recent years, in vitro and in vivo ADMET prediction methods have been widely used, but it is impractical to perform complex and expensive ADMET experiments on a large number of compounds^9,10. Thus, in silico strategy to predict ADMET properties has become very attractive as a Cost-Saving-High-Throughput alternative to conventional experimental methods^11-17.

Since prehistoric times, humans have used natural products, such as plants, animals, microorganisms, and marine organisms, in medicines to alleviate and treat diseases¹⁸. Natural products, which have evolved over millions of years, have a unique chemical diversity, which results in diversity in their biological activities and drug-like properties¹⁹. Those products have become one of the most important resources for developing new lead compounds and scaffolds^20,21. 

World Health Organization (WHO) estimates that 4 billion people, 80 percent of the world population, presently use herbal medicine for some aspect of primary health care. Plant exhibit a wide range of pharmacological activities including antimicrobial, antioxidant, anticancer, hypolipidemic, cardiovascular, central nervous system, respiratory, immunological, anti-inflammatory, analgesic, antipyretic and many other pharmacological effects. In traditional medicine, cumin was used to treat hoarseness, jaundice, dyspepsia and diarrhoea. Seeds were used for stomachic, diuretic, carminative, stimulant, astringent and abortifacient properties^20-23. 

Cumin (Cuminum cyminum L.) is an annual and herbaceous plant (Family: Apiaceae). It is a multipurpose plant species cultivated in the Middle East, India, China, and several Mediterranean countries, including Tunisia. Its fruit, known as cumin seed, is most widely used for culinary and medicinal purposes²⁴. It is generally used as a food additive, popular spice, and flavouring agent in many cuisines. Cumin has also been widely used in traditional medicine to treat a variety of diseases. Pharmacological studies have proven that C. cyminum exerts antimicrobial, insecticidal, anti-inflammatory, analgesic, antioxidant, anticancer, antidiabetic, antiplatelet aggregation, hypotensive, bronchodilatory, immunological, contraceptive, anti-amyloidogenic, anti-osteoporotic, aldose reductase, α-glucosidase and tyrosinase inhibitory effects²³. The medicinal parts were Cumin oil extracted from the ripe fruit and the ripe, dried fruit²⁵. Phytochemical analysis of C. cyminum revealed that it contains alkaloid, coumarin, anthraquinone, flavonoid, glycoside, protein, resin, saponin, tannin and steroid²³. 

Physicochemical characteristics

Moisture content: 8%, PH: 7.3, total ash: 7.5, acid insoluble ash: 18%, alcohol soluble extractive: 6.58%, water soluble extractive: 138% and ether soluble extractive: 11.44 ± 0.20 and 12.36 ± 0.23% in the wet and dry fruits. Crude protein 18.40 ± 0.16 and 19.88 ± 0.20%, crude fibres 21.82 ± 0.13 and 23.57 ± 0.13%, total carbohydrate 55.58 and 60.05% in the wet and dry fruits respectively²³. Physical properties of the essential oil of cumin seeds: extraction percentage: 2.3-5.7 %, color: colourless or pale yellow, refractive index (20 ºC): 1.47-1.50, density (20 ºC): 0.90-0.94, alcohol solubility (80% v/v): 1:1.3-1:2, aldehyde percentage (Cuminaldehyde): 35-63%, acidity (Cuminic acid): 0.36-1.8, alcohol percentage (Cuminol): 3.5, carbonyl index: 9.32 and steric index: 19.24²³. 

Chemical constituents

Phytochemical analysis showed that C. cyminum contained: alkaloid, anthraquinone, coumarin, flavonoid, glycoside, protein, resin, saponin, tannin and steroid. Nutrient contents of cumin (seeds) were included: calories 7.50, calories from fat 4.00, calories from saturated fat 0.28, protein (g) 0.36, carbohydrates (g) 0.88, dietary fibre (g) 0.22, total fat (g) 0.44, saturated fat (g) 0.04, monounsaturated fat (g) 0.28, polyunsaturated fat (g) 0.06, water (g) 0.16, Ash (g) 0.16, vitamin A (IU) 25.40, vitamin A (RE) 2.54, α-carotenoid (RE) 2.54, beta carotene (μg) 15.24, thiamin – B1 (mg) 0.02, niacin – B3 (mg) 0.10, niacin 0.10, vitamin C 0.16, vitamin E α 0.02, vitamin E (IU) 0.04, vitamin E (mg) 0.02, folate (μg) 0.20, vitamin K (μg) 0.11, calcium (mg) 18.62, copper (mg) 0.02, iron (mg) 1.32, magnesium (mg) 7.32, manganese (mg) 0.06, phosphorus (mg) 9.98, potassium (mg) 35.76, selenium (μg) 0.10, sodium (mg) 3.36, zinc (mg) 0.10, palmitic acid (g) 0.02, oleic (g) 0.28, linoleic acid (g) 0.06 and omega 6 fatty acids (g) 0.06 (79). Organic acids (aspartic, citric, malic, tartaric, propionic, ascorbic, oxalic, maleic and fumaric acids) were isolated from seeds of Cuminum cyminum²⁶. Cumin fruits contained 2.5 to 4.5% volatile oil and 10% fixed oil (Table 1). 

Major compounds in Turkish cumin (Cuminum cyminum) seed oil were cuminaldehyde (19.25-27.02%), p-mentha-1,3-dien-7-al (4.29-12.26%), p-mentha-1,4-dien-7-al (24.48-44.91%), γ-terpinene (7.06-14.10%), p-cymene (4.61-12.01%) and β-pinene (2.98-8.90%) . Cuminaldehyde, γ-terpinene, o-cymene, limonene and β-pinene were determined to be the major constituents of Syrian C. cyminum. The major compounds in cumin essential oil of Egyptian cultivars were cumin aldehyde (35.25%), tetradecene (12.25%), γ-terpenene (12%), β-ocimene (9.72%), p-mentha-2-en-ol (9%), α-terpinyl acetate (5.32%), α-terpinolene (3%), lmonine (0.5%), myrcene (0.2%), β-pinene (0.9%) and α-pinene (0.19%). Tunisian variety of C. cyminum contained cuminlaldehyde (39.48%), gamma-terpinene (15.21%), O-cymene (11.82%), beta-pinene (11.13%), 2-caren-10-al (7.93%), trans-carveol (4.49%) and myrtenal (3.5%) as major components²⁷. However, it must be pointed out that in recent times, computational approaches in preclinical studies on drug discovery and development.

MATERIALS AND METHODS

Kingdom - Plantae; Sub kingdom - Viridiplantae; Infra kingdom - Streptophyta; Super division - Embryophyta; Division - Tracheophyta; Sub division - Spermatophytina; Class - Magnoliopsida; Super order - Asteranae; Order - Apiales; Family - Apiaceae; Genus - Cuminum; Species - Cuminum cyminum. Common names - Jiiraa (Jeera), Zeera (zira, ziira), safed ziiraa (Safed zira), Safed jiiraa (Safaid jeera)

Botanical Description of the plant - Cuminum cyminum

Plants – Herbs – usually 10–30(–50) cm tall; Leaf: Basal petioles 1–2 cm; sheaths lanceolate, margins white and membranous; blade 3–8 × 2–7 cm; ultimate divisions long-filiform, 15–60 × 0.4–0.7 mm. Inflorescence: Umbels many, 2–3 cm across; peduncles 3–10 cm; Bracts 2–6 (–8), linear or linear-lanceolate, 10–50 × 0.5–1.2 mm, unequal, entire or apex 2–3-fid, usually longer than the rays, margins membranous; rays (1–)3–6, 3–20 mm, rather stout, very unequal; Bracteoles 3–5, similar to bracts, 4–10 × 0.3–0.6 mm, very unequal, sometimes reflexed; umbellules 3–8-flowered; Flowers: pedicels 3–6 mm, stout, very unequal. Calyx: teeth 0.5–2 mm, longer than the styles. Petals ca. 1.4 × 1 mm. Fruit 5–7 × 1.6–2.8 mm; primary ribs short setulose, secondary ribs densely stellate setulose; Fl. and Fr. Feb–Jun–Sep. 

Phytochemical Screening 

The cumin seeds were purchased from the local market in Madurai. The methanolic extracts were subjected to chemical tests for the detection of different phytoconstituents using standard procedures³³. 

Test for Phenols (FeCl₃ Test)

To 1 ml of the extract, 3 ml of distilled water followed by few drops of 10% aqueous Ferric chloride solution was added. Formation of blue or green colour indicates the presence of phenols. 

Test for Flavonoids (Shinoda Test)

To 2 ml of the extract, 1 ml of 1% ammonia solution was added. Appearance of yellow colour indicates the presence of flavonoids. 

Test for Tannins (FeCl₃ Test)

To 1 ml of the extract, 1 ml of 0.008 M Potassium ferricyanide was added and then add 1ml of 0.02 M Ferric chloride containing 0.1 N HCl. Appearance of blue-black colour indicates the presence of Tannins. 

Test for Alkaloids (Wagner’s Reagent Test)

Approximately, 1 ml of crude extract was mixed with 2 ml of Wagner’s reagent. Reddish brown colour precipitate indicates the presence of alkaloids. 

Test for Carbohydrates (Fehling’s test, Benedict’s test)

Fehling’s test 

Equal volume of Fehling A and Fehling B reagents were mixed together and then add 2ml of crude extract in it and gently boiled. A brick red precipitate appeared at the bottom of the test-tube indicates the presence of reducing sugars. 

Benedict’s test

1 ml of crude extract was mixed with 2ml of Benedict’s reagent and boiled. A reddish brown precipitate was formed which indicates the presence of the carbohydrates. 

Test for Proteins (Millon’s Test, Ninhydrin Test)

Millon’s test

1 ml of crude extract was mixed with 2ml of Millon’s reagent; white precipitate appeared which turned red upon gentle heating that confirmed the presence of protein. 

Ninhydrin test

1 ml of crude extract was mixed with 2ml of 0.2% solution of Ninhydrin and boiled. A violet colour precipitate was appeared suggesting the presence of amino acids and proteins. 

Test for Cardiac glycosides (Keller-Kiliani test) 

5 ml of extract was treated with 2 ml of glacial acetic acid containing one drop of ferric chloride solution. This was underlayed with 1 ml of concentrated sulphuric acid. A browning of the interface indicates a deoxy-sugar characteristic of carotenoids. A violet ring may appear below the brown ring, while in the acetic acid layer, a greenish ring may form just gradually throughout thin layer.

Test for Saponins (Foam Test)

2 ml of crude extract was mixed with 5 ml of distilled water in a test tube and it was shaken vigorously. Add some drops of olive oil. The formation of stable foam was taken as an indication for the presence of saponins. 

Test for Coumarin (Sodium hydroxide Test)

10 % Sodium hydroxide was added to the extract and chloroform was added. Formation of yellow color shows the presence of Coumarin. 

Test for Terpenoids (Salkowski test) 

5 ml of extract was mixed with 2 ml of chloroform and 3 ml of concentrated sulphuric acid was carefully added to form a layer. A reddish brown coloration of the inter face was formed which indicates the presence of terpenoids. 

 

 

Test for Steroids (Salkowski Test)

2 ml of acetic anhydride was added to 0.5 ml of crude extract containing 2 ml of sulphuric acid. The colour changed from violet to blue or green in samples indicates the presence of steroids. 

Test for Quinones (Sodium hydroxide Test)

Diluted sodium hydroxide was added to the 1 ml of crude extract. Blue green or red coloration indicates the presence of quinones. 

Test for Anthraquinones (Borntragers test) 

0.5 g of extract was boiled with 10% hydrochloric acid for few minutes in water bath. It was filtered and allowed to cool. Equal volume of CHCl₃ was added to the filtrate. Few drops of 10% ammonia was added to the mixture and heated. Formation of rose – pink color indicates of n-hexane, chloroform, ethyl acetate and methanol of the presence of the anthroquinones.

Sample preparation and characterization

For phytochemical screening, 25 g of pulverized seeds were extracted with 125 mL of three solvents namely; methanol, distilled water and methanol/water (1:1) for 72 h. The plant extracts were filtered and concentrated using rotary evaporator under reduced pressure. Preliminary phytochemical analysis was carried out to test for the presence of tannins, saponins, flavonoids, alkaloids, anthocyanins, betacyanins, quinones, glycosides, cardiac glycosides, terpenoids, triterpenoids, phenols, coumarins, steroids and acids in all the three extracts following the standard test methods. Also, 10 g of each powdered plant material was extracted with methanol, distilled water and methanol/distilled water (1:1), respectively, for 72 h. The extracts were filtered and concentrated to 1 mL using BUCHI rotary evaporator under reduced pressure. Then, 1 mL of crude methanolic, water and methanol/ water extracts were taken for FTIR analysis, while 1 mL methanolic extracts were taken in amber GC vials for GC–MS analysis.

GC-MS Analysis 

Phyto-components were identified using GCMS detection system as previously with minor modification, whereby portion of the extract was analyzed directly by headspace sampling. GCMS analysis was accomplished using an Agilent 7890A GC system set up with 5975C VL MSD (Agilent Technologies, CA, and USA). Capillary column used was DB5MS (30 m × 0.25 mm, film thickness of 0.25 μm; J&W Scientific, CA, USA). Temperature program was set as follows: initial temperature 50°C held for 1 min, 5°C per min to 100°C, 9°C per min to 200°C held for 7.89 min, and the total run time was 30 min. The flow rate of helium as a carrier gas was 0.811851 mL/min. MS system was performed in electron ionization (EI) mode with Selected Ion Monitoring (SIM). The ion source temperature and quadruple temperature were set at 230°C and 150°C, respectively. The identification of components was based on retention time on the capillary column and matching the GC-MS with the National Institute of Standards and Technology (NIST) library³⁴.

Fourier Transform Infrared Spectroscopy (FTIR) Analysis

The extracts were analyzed using Agilent Cary 630 FTIR spectrometer equipped with Micro-lab PC software with ATR sampling unit with a resolution of 8 cm^-1 and scan range of 4000 cm^-1 to 650 cm^-1.

RESULTS 

Phytochemical Screening 

In the present study, screening for Alkaloids (Wagner’s reagent Test) exhibited + result; Anthraquinones (Borntragers Test) showed + result; Carbohydrates (Fehling’s test, Benedict’s test) indicated ++ result; Coumarins (Sodium hydroxide Test) showed + result; Flavonoids (Shinoda Test) showed ++ result; Glycosides (Keller-Kiliani Test) showed + result; Phenol (FeCl3 Test) showed - result; Proteins (Millon’s Test, Ninhydrin Test) indicated ++ result; Quinones (Sodium hydroxide Test) revealed + result; Saponins (Foam Test) showed + result; Steroids (Salkowski Test) presented + result; Tannins FeCl3 Test) showed ++ result; Terpenoids (Salkowski Test) exhibited ++ result (Table 2).

A total of 21 compounds were detected in the GCMS analysis, at RT interval of 4.363 α-Terpinene (C₁₀H₁₆) was detected with a MW of 136 in the seeds and oil samples with a percentage peak area of 9.74, 0.0; at RT interval of 4.716 α-Thujene (C₁₀H₁₆) was detected with a MW of 136  in seeds and oil samples with a percentage peak area of 0.0, 0.29; while at RT interval of 4.842 α-Pinene (C₁₀H₁₆) was detected with a MW of 136 in both the seeds and oil samples with a percentage peak area of 0.12, 0.92; similarly, at RT interval of 5.574 β-Pinene (C₁₀H₁₆) was detected with a MW of 136 in the seeds and oil samples with a percentage peak area of 2.1, 0.0; while at RT interval of 5.668 Santolina triene (C₁₀H₁₆) was detected with a MW of 136 in both the seeds as well the oil samples with a percentage peak area of -, 11.52; at RT interval of 5.747 α-Myrcene (C₁₀H₁₆) was detected with a MW of 136 in the seeds as well as in the oil samples with an average peak area of 0.3, 0.71.

Likewise, at an interval of 6.344 RT ρ-Menthatriene (C₁₀H₁₄) was detected with a MW of 134 in the seeds and oil samples with a percentage peak area of 18.77, 24.63; at RT interval of 6.968 Terpinolene (C₁₀H₁₆) was detected with a MW of 136 in the seeds and oil samples with a percentage peak area of 15.95, 16.51; at RT interval of 8.614 Limonene (C₁₀H₁₆) was detected with a MW of 136 in the seeds and oil samples with a percentage peak area of 0.19, 0.0; at RT interval of 8.752 4-Terpineol (C₁₀H₁₈O) was detected with a MW of 154 in the seeds and oil samples with a percentage peak area of -, 0.3; at RT interval of 8.761 1,8-cineole (C₁₀H₁₈O) was detected with a MW of 154 in the seeds and oil samples with a percentage peak area of 0.46, 0.14.

At an interval of 9.431 (RT) Benzaldehyde ρ-isopropyl (C₁₀H₁₂O) was detected with a MW of 148 in the seeds and oil samples with a percentage peak area of 1.27, 0.0; while at RT interval of 9.96 Cuminaldehyde (C₁₀H₁₂O) was detected with a MW of 148 in the seeds and oil samples with a percentage peak area of 32.59, 31.65; at RT interval of 10.577 Myrtenal (C₁₀H₁₄O) was detected with a MW of 150 in the seeds and oil samples with a percentage peak area of 8.74, 1.78; at RT interval of 10.248 cis-Ocimene (C₁₀H₁₄O) was detected with a MW of 150 in the seeds and oil samples with a percentage peak area of 10.26, 4.14; at RT interval of 15.881 α-Terpinen-7-al  (C₁₀H₁₄O) was detected with a MW of 150 in both the seeds and oil samples with a percentage peak area of 3.98, 4.59; 

At and interval of 15.965 (RT) o-Cymen-7-ol was detected with a MW of 150 (C₁₀H₁₄O) in the seeds and oil samples with a percentage peak area of 0.0, 1.11; at RT interval of 16.072 γ-Terpinen-7-al was detected with a MW of 150 (C₁₀H₁₄O) in the seeds and oil samples with a percentage peak area of 1.95, -0.0; at RT interval of 16.186 Thymol was detected with a MW of 150 (C₁₀H₁₄O) in the seeds and oil samples with a percentage peak area of 0.0, 0.35; at RT interval of 16.797 4-Hydroxy-cryptone was detected with a MW of 154 (C₁₀H₁₄O) in the seeds and oil samples with a percentage peak area of 1.68, 0.38; at RT interval of 20.047 4-(1-methylethyl)-benzoic acid was detected with a MW of 164 (C₁₀H₁₄O₂) in the seeds and oil samples with a percentage peak area of 0.97, 1.43 respectively (Table 3).

FTIR analysis showed the  presence of a strong peak value (cm^-1) of 700.998 in the reference range of 610-700 with functional group -C=C-H ;C-H bend indicate the presence of Alkynes in the compound; while a peak at 3543.56 with in the reference range of 3500-3700 with O-H (H-bonded), usually broad indicates the presence of Alcohols & Phenols in the compound; similarly, peak at 2873.42 with in the range of 2850-3000 with CH₃, CH₂ & CH bonds shows that alkanes are present in the compound; while a peak at 2856.06 in the range of 2850-3000 with CH₃, CH₂ & CH₂ or 3 bands indicates the presence of alkanes in the compound; however, peak at 2141.56 in the range of 2100-2260 with C-C triple bond indicates alkynes in the compound; a peak at 1716.34 in the range of 1706-1720 with C=O stretching, indicates the presence of a dimer Carboxylic acid in the compound; while peak at 1646.91 in the range of 1640-1690 with a C=N stretching depicts the presence of Imine/ Oxime in the compound; a peak at 1530.24 (range 1500-1550) with N-O stretching depicts the occurrence of a Nitro-compound; while a peak at 1454.06 (range 1400-1500) with C-C Stretch indicates presence of aromatic compound; 

At a peak value of 1436.71(cm^-1), in the reference range of 1395-1440 a O-H bend was recorded indicating the presence of carboxylic acid in the compound; similarly, at a peak value of 1408.75 within the reference range of 1380-1410 a S=O stretching was recorded indicating the presence of sulfonyl chloride in the compound; while at a peak value of 1070.3 within the reference range of 1030-1070 a S=O was recorded indicating the presence of sulfoxide in the compound; similarly, 897.701; 675-900; a C-H “loop” indicates the presence of aromatic group in the compound; 2991.05; 2850-3000; a N-H stretching shows the presence of alkanes in the compound; while, a medium Peak Value (cm^-1) of 2770.24 with in the range of 2695-2830 with C-H (aldehyde C-H) indicates the presence of Aldehydes/ Ketones in the compound. 

On the other hand occurrence of a medium peak at 1322.93 within the reference range of 1210-1390 with O-H bending indicates the presence of phenol group in the compound; while occurrence of a medium peak at 1246.75 within the reference range of 1020-1250 with C-N stretching indicates the presence of alkyl aryl ether group in the compound; however a medium peak at 939.163 within the reference range of 910-959 with a O-H bend indicates the presence of carboxylic acids in the compound; while occurrence of a medium peak at 828.882 within the reference range of 550-850 with C-Cl stretch indicates the presence of alkyl halides in the compound; whereas a medium peak at 590.111 within the reference range of 515-690 with a C-Br stretching indicates the presence of Alkyl halides in the compound (Table 4; Fig. 1).

DISCUSSION 

Ethnobotanical studies and phytochemical screening remains the mainstay in the hunt of bioactive secondary metabolites from natural sources. But computational approaches in preclinical studies on drug discovery and development play a major role^35-46. Therefore, simultaneous progress in both the fields has become the rule of the day. In a study, Romeilah et al.⁴⁷, isolated 20 compounds from the C. cyminum (seeds) oil including: α-pinene 2.14, sabinene 1.01, β-pinene 4.89, β-myrcene 1.45, α-terpinene 0.84, p-cymene 1.77, limonene 0.24, α-terpinene 1.07, α-terpinolene 0.08, Camphor 0.12, Terpinen-4-ol 0.04, α-terpineol 2.47, geraniol 0.07, geranyl acetate 4.11, β-caryophyllene 3.44, α-phellandrene 1.09, cuminaldehyde 60.01, thymol 2.04, β-farnesene 3.01 and caryophyllene oxide 6.12. 

However, Gachkar et al.⁴⁸, isolated 32 compounds from C. cyminum oil including: isobutyl isobutyrate 0.8, a-thujene 0.3, a-pinene 29.1, sabinene 0.6 , myrcene 0.2 , d-3-carene 0.2, p-cymene 0.3, limonene 21.5, 1,8-cineole 17.9, (E)-ocimene 0.1, g -terpinene 0.6, terpinolene 0.3, linalool 10.4, a-campholenal 0.03, trans-pinocarveole 0.07 , d-terpineole 0.09, terpinene-4-ol 0.5, a-terpineole 3.17, trans-carveole 0.4, cis-carveole 0.07, geraniol 1.1, linalyl acetate 4.8, methyl geranate 0.2, a-terpinyl acetate 1.3, neryl acetate 0.09, methyl eugenol 1.6, b-caryophyllene 0.2, a-humulene 0.2, spathulenol 0.07, caryophylleneb epoxide 0.1, humulene epoxide II 0.08 and acetocyclohexane dione-2 0.4. 

Chaudhary et al.,⁴⁹ identified as much as 49 components in the essential oil constituents of the C. cyminum fruit that represented 99.78% of total detected constituents. The essential oil was characterized by the presence of monoterpene (79.61%), sesquiterpene (2.66%), aromatic (16.55%) and aliphatic compounds (0.66%). Among 34 monoterpenes detected, there were 14 hydrocarbons (41.28%), 12 alcohols (5.76%), 06 keto compounds (31.92%), 01 aldehyde (0.54%) and 02 esters (0.11%). 

However, predominant monoterpene hydrocarbon was γ-terpinene (23.22%) followed by α-phellandrene (12.01%), α-pinene (1.78%) and α-terpinene (1.24%). Among 12 monoterpenic alcohols, p-menth-2-en-7-ol (3.48%) was the major alcoholic constituent and trans-dihydrocarvone (31.11%) was the prominent monoterpenic ketone in the essential oil⁵⁰. Sesquiterpenes identified in the oil were teresantalol (2.62%) and karvaknol (0.04%)⁴⁹. Aromatic compounds detected were p-cymene (15.87%), 8a-methyl octahydro-2 (1H)- naphthalenone, 2-isopropyl-5-methyl phenol, p-cymen-7-ol, o-cymen-5-ol, p-cymen-3-ol, 6-allyl-4,5-dimethoxy-1,3-benzodioxole and 2,a,8,8-tetramethyl decahydrocyclopropanal [d] naphthalene. The aliphatic compounds included 1- (1, 2, 3-trimethyl-2- cyclopenten-1-yl) ethanone, 3-isopropyl phenol, 2-methyl-4-isopropyliden-cyclopentan-1-al, 1-methyl-4-iso propyl-3-cyclohexen-1-ol, 2-isopropenyl-5-methyl-hex-4-enal, 4-isopropyl cyclohex-1,3-dien-1-yl) methanol, 4-isopropyl-1-cyclohexen-1-carbaldehyde, hexadecylene oxide and (3,4-dimethyl-2-oxo-cyclopenten-1-yl) acetic acid. 

Similarly, that analysis of the methanolic extract of the fruits of C. cyminum led to the isolation of five terpenic and steroidal constituents, they were characterized as 1,4,5,8-tetrahydroxynaphthyl geranilan-10ʹ-al 1ʹ-oate, lanost-5,20 (22)-dien-3α-olyl ndocosanoate, labdan-6α,16,20-triol-16- (10ʹ,11ʹ- dihydroxy anthraquinone-2ʹ-oate), stigmast-5-en- 3β-O-D-arabinopyranosyl-2ʹ-benzoate and lanost-5,24-dien-3β-ol 3β-O-D- arabinopyronosyl-2ʹ- noctadec- 9ʹʹ, 12ʹʹ-dienoate. The characteristic odour of cumin was attributed to the presence of sminaldehyde, 1, 3-p-menthadien-7al, 1-4-p-menthadien-7-al. 14 free amino acids were also isolated from the seeds. While, flavonoid glycosides isolated from the plant were included apigenin-7-glucoside, luteolin-7-glucoside, luteolin-7-glcuronosyl glucoside, luteolin and apigenin. Total polypheols in cumin were 4.98± 0.31. (mg GAE/g DW). Phenols (salicylic acid, gallic acid, cinnamic acid, hydroquinone, resorcinol, P-hydroxybenzoic acid, rutin, coumarine, quercetin) were isolated from seeds of C. cyminum⁵¹.

Free radical scavenging and antioxidant activity of silver nanoparticles synthesized from Cuminum cyminum (Cumin) seed extract could be used as an effective antioxidant⁵². However, C. cyminum roots, stems and leaves, and flowers were investigated for their total phenolic, flavonoids, and tannins contents. In all C. cyminum organs, total phenolic content ranged from 11.8 to 19.2 mg of gallic acid equivalents per gram of dry weight (mg of GAE/g of DW). Among the polyphenols studied, 13 were identified in roots, 17 in stem and leaves, and 15 in flowers. The major phenolic compound in the roots was quercetin (26%), whereas in the stems and leaves, p-coumaric, rosmarinic, trans-2-dihydrocinnamic acids and resorcinol were predominant. In the flowers, vanillic acid was the main compound (51%)⁵³. A total of 19 phenolic compounds were successfully identified during the ripening of cumin seeds. Rosmarinic acid was the major phenolic acid for the unripe seeds, while, half ripe and full ripe seeds were dominated by p-coumaric acid. 

CONCLUSION 

Phytochemical screening of bioactive natural products from Cuminum cyminum, GCMS analysis revealed the presence of 21 compounds, FTIR profile with the manifestation of strong and medium peak corresponding to the presence different functional groups in the compounds detected. The unique range of natural products in GCMS/ FTIR profile C. cyminum if ADMET prospected could be exploited for a wide range of biomedical applications.    

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Table 1: Nutritional value per 100 g of Cuminum cyminum

Energy	1,567 kJ (375 kcal)
CHEMICAL CONSTITUENT	QUANTITY
Carbohydrates	44.24 g
Sugars	2.25 g
Dietary fibre	10.5 g
Fat	22.27 g
Saturated	1.535 g
Monounsaturated	14.04 g
Polyunsaturated	3.279 g
Protein	17.81 g
VITAMINS	QUANTITY % (DV)
Vitamin A equiv.	8% (64 μg)
beta-Carotene	7% (762 μg)
Vitamin A	1270 IU
Thiamine (B1)	55% (0.628 mg)
Riboflavin (B2)	27% (0.327 mg)
Niacin (B3)	31% (4.579 mg)
Vitamin B6	33% (0.435 mg)
Folate (B9)	3% (10 μg)
Vitamin B12	0% (0 μg)
Choline	5% (24.7 mg)
Vitamin C	9% (7.7 mg)
Vitamin D	0% (0 μg)
Vitamin D	0% (0 IU)
Vitamin E	22% (3.33 mg)
Vitamin K	5% (5.4 μg_)
MINERALS	QUANTITY %DV†
Calcium	93% (931 mg)
Iron	510% (66.36 mg)
Magnesium	262% (931 mg)
Manganese	159% (3.333 mg)
Phosphorus	71% (499 mg)
Potassium	38% (1788 mg)
Sodium	11% (168 mg)
Zinc	51% (4.8 mg)
OTHER CONSTITUENTS	QUANTITY
Water	8.06 g

 

 

 

 

 

 

 

 

 

Table 2 Phytochemical analysis of phytocompounds from Cuminum cyminum

PHYTOCONSTITUENTS	TEST	PRESENT/ ABSENT
Alkaloids	Wagner’s reagent Test	+
Anthraquinones	Borntragers Test	+
Carbohydrates	Fehling’s test, Benedict’s test	++
Coumarins	Sodium hydroxide Test	+
Flavonoids	Shinoda Test	++
Glycosides	Keller-Kiliani Test	+
Phenol	FeCl3 Test	-
Proteins	Millon’s Test, Ninhydrin Test	++
Quinones	Sodium hydroxide Test	+
Saponins	Foam Test	+
Steroids	Salkowski Test	+
Tannins	FeCl3 Test	++
Terpenoids	Salkowski Test	++

+++ = Abundantly present; ++ = moderately present; + = slightly present; - = absent
 

Table 3: GCMS analysis of phytocompounds from fruits of Cuminum cyminum

SNO	COMPOUND NAME	RT	MW	MF	% AREA
					SEEDS	OIL
	α-Terpinene	4.363	136	C10H16	9.74	-
	α-Thujene	4.716	136	C10H16	-	0.29
	α-Pinene	4.842	136	C10H16	0.12	0.92
	β-Pinene	5.574	136	C10H16	2.1	-
	Santolina triene	5.668	136	C10H16	-	11.52
	α-Myrcene	5.747	136	C10H16	0.3	0.71
	ρ-Menthatriene	6.344	134	C10H14	18.77	24.63
	Terpinolene	6.968	136	C10H16	15.95	16.51
	Limonene	8.614	136	C10H16	0.19	-
	4-Terpineol	8.752	154	C10H18O	-	0.3
	1,8-cineole	8.761	154	C10H18O	0.46	0.14
	Benzaldehyde ρ-isopropyl	9.431	148	C10H12O	1.27	-
	Cuminaldehyde	9.96	148	C10H12O	32.59	31.65
	Myrtenal	10.577	150	C10H14O	8.74	1.78
	cis-Ocimene	10.248	150	C10H14O	10.26	4.14
	α-Terpinen-7-al	15.881	150	C10H14O	3.98	4.59
	o-Cymen-7-ol	15.965	150	C10H14O	--	1.11
	γ-Terpinen-7-al	16.072	150	C10H14O	1.95	--
	Thymol	16.186	150	C10H14O	--	0.35
	4-Hydroxy-cryptone	16.797	154	C10H14O	1.68	0.38
	4-(1-methylethyl)-benzoic acid	20.047	164	C10H14O2	0.97	1.43

 

Table 4: IR spectral frequencies of functional groups in methanolic fruit extract of C. cyminum 

 

 

Figure 1: FTIR spectrum of methanolic fruit extract of C. cyminum