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Journal of Drug Delivery and Therapeutics

Open Access to Pharmaceutical and Medical Research

Copyright  © 2022 The  Author(s): This is an open-access article distributed under the terms of the CC BY-NC 4.0 which permits unrestricted use, distribution, and reproduction in any medium for non-commercial use provided the original author and source are credited

Open Access   Full Text Article                                                                                                                                                                                              Research Article 

Phytochemical Screening, GCMS and FTIR Profile of Bioactive Compounds in Solanum lycopersicum Wild Fruits collected from Palani Hill Ranges of the Western Ghats 

Ramya S.¹, Chandran M.², King Immanuel J.³, Jayakumararaj R.⁴*, Loganathan T.⁵, Pandiarajan G.⁶, Kaliraj P.⁷, Grace Lydial Pushpalatha G⁸, Abraham GC.⁹, Vijaya V.¹⁰, Aruna Devaraj¹¹, Sutha S.¹², Ram Chand Dhakar¹³

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

² Department of Zoology, Thiruvalluvar University, Serkadu, Vellore-632115, TN, India

³ Department of Zoology, Government Arts College, Melur – 625106, Madurai District, TN, India

⁴ Department of Botany, Government Arts College, Melur – 625106, Madurai District, TN, India

⁵ Department of Plant Biology & Plant Biotechnology, LN Government College (A), Ponneri, TN, India

⁶ Department of Botany, Sri S Ramasamy Naidu Memorial College (A), Sattur - 626203 TN, India

⁷ Department of Zoology, Sri S Ramasamy Naidu Memorial College (A), Sattur - 626203 TN, India

⁸ PG Department of Botany, Sri Meenakshi Government Arts College, Madurai – 625002, TN, India

⁹ PG & Research Department of Botany, The American College, Madurai – 625002, TamilNadu, India

¹⁰ Department of Botany, EMG Yadava College (Women), Thiruppalai - 625014, Madurai, TN, India

¹¹ Director, Rajendra Herbal Research Centre, NRMC, Periyakulam Theni District, TamilNadu, India

¹² Department of Medicinal Botany, Govt. Siddha Medical College, Palayamkottai, Tamil Nadu, India

¹³ Hospital Pharmacy, SRG Hospital & Medical College Jhalawar-326001, Rajasthan, India

INTRODUCTION

                  Tomatoes (Solanum lycopersicum L.; Family: Solanaceae), are frequently included in Mediterranean diet and are widely consumed as vegetables, play an important role in nutrition attributed to well-established health benefits¹. Tomatoes are commonly used in processed food products². Nutrients in tomatoes include vitamins, minerals, fiber, protein, amino acids, fatty acids, carotenoids and phytosterols^3-8. These nutrients drive physiological, metabolic and biochemical processes associated with constipation high blood pressure, blood circulation, lipid profile, body fluids, detoxification and bone structure⁹. Tomatoes are excellent source of bioactive compounds involved in prevention of human chronic diseases - cardiovascular disease (CVD), cancer, and neurodegenerative diseases^10-11. 

High concentrations of natural antioxidant, such as carotenoids (β-carotenoids and lycopene), ascorbic acid (vitamin C), tocopherol (vitamin E) and bioactive phenolic compounds (quercetin, kaempferol, naringenin and lutein, caffeic, ferulic and chlorogenic acids), tomatoes ameliorate chronic several diseases^12,14. Antioxidants inhibit reactive oxygen species (ROS) by scavenging free radicals, inhibiting cellular proliferation and damage, inhibit apoptosis, metal chelation, modulate enzymatic activity, cytokine expression and signal transduction^12-15. Pharmacological activities of lycopene and other phenolic compounds include anticancer, anti-inflammatory, antidiabetic, anti-allergenic, anti-atherogenic, antithrombotic, antimicrobial, antioxidant, vasodilator and cardioprotection^12-18. Polyphenolic compounds and carotenoids trigger sensory activities including maintaining good aroma, taste¹⁹. Tomato is a dietary source of soluble and insoluble dietary fibers - cellulose, hemicelluloses and pectin²⁰ reported to ameliorate bowel disorders, cancer, diabetes, CVDs, and obesity²¹. Proximate composition of tomatoes includes pH, energy, acidity and reducing sugars²². Combination of all - vitamins, minerals, amino acids, fatty acids makes tomato a balanced diet^23-25.

                  Nutritional composition of tomato is based on cultivar (genetic), soil conditions, extraction procedures, analytic methods and environmental/ climatic conditions. During processing of tomato products, up to 30% of original weight are turned into waste, which may be nutritive ²⁶. Peel and seeds are the main waste product of tomato, both are rich in protein, dietary fibers, bioactive compounds and lycopene²⁷. By-products of SL are used as additives in meat processing industries. Further, by-products of SL contain multiple bioactive compounds that could serve as a renewable source for obtaining natural antioxidants and colorants (carotenoids)²⁸. Although by products of SL is a rich source of nutrients, comprehensive research should be carried out before marketed for human consumption²⁹. In spite of significant health benefits, tomatoes demonstrate few undesired effects when consumed in large amounts. Adverse effects of tomato excess-intake are associated with renal problems, allergies, arthritis, heartburn, and migraine³⁰. With this background information the aim of this paper is to screen for bioactive secondary metabolites followed by GCMS and FTIR analysis of bioactive compounds in Solanum lycopersicum wild fruits. 

MATERIALS AND METHODS

Phytochemical Screening 

                  Fruits were collected from the wild in the Palani Hills region of the Western Ghats, TamilNadu, India. Type specimen was identified and authenticated by Prof. Dr. S. Sutha at Department of Medicinal Botany, Government Siddha Medical College, Palayamkottai, Tirunelveli District, Tamil Nadu, India. The methanolic extracts were subjected to chemical tests for the detection of different phytoconstituents using standard procedures^31-35. 

Sample preparation

Using direct method of extraction, approximately 100 g of dried fruit powder was extracted with 500 ml of different solvents such as petroleum ether, chloroform and methanol to determine the profile of bioactive compounds in the test samples. The extract was transferred in to glass vials. The process was repeated 3 times with fresh solvent. The solvent was removed by Rotavapor® R-300 (BÜCHI-GmbH, Germany). The extracted residue was re-dissolved in the respective solvent to yield a final volume of 10mg/ml and the content was stored in cold (at 4°C) until further use. The extracts were subjected to chemical tests for the detection of phytoconstituents using standard procedures as described previously^31-40. 

TEST FOR ALKALOIDS 

Mayer's test: Few drops of Mayer's reagent was added to 1 mL of plant extract, appearance of a deep yellow or white precipitate indicated the presence of alkaloids in the solution. (Mayer’s reagent was freshly prepared by dissolving mercuric chloride (1.36 g) and potassium iodide (5.00 g) in 100 ml water). 

Dragendorff's test: To 2 mL of the extract added 1 mL of Dragendorff's reagent along the side of the test tube. Formation of orange or orange reddish brown precipitate indicated the presence of alkaloids. Dragendorff's reagent was prepared by Sol A: 0.85g bismuth subnitrate, 40mL water, and 10mL glacial acetic acid and Sol B: 8g potassium iodide and 20mL water. 5mL each of Sol A & B with 20mL of glacial acetic acid and 70-100 mL of water is mixed to prepare Dragendorff's reagent. 

Hager's test: Hager's test was done by adding a few drops of Hager's reagent to plant extracts and appearance of a yellow-color precipitate indicated the presence of alkaloids in the solution. Hager's reagent is saturated solution of picric acid. 

Wagner’s 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. Wagner's Reagent was prepared by mixing 2.5 gm iodine in 12.5 gm of potassium iodide (KI 2); add 250 ml of water to produce solution. 

TEST FOR GLYCOSIDES 

Test For Anthraquinones Glycosides 

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. 

Baljet test: Part of plant containing cardiac glycoside is dipped in sodium picrate solution; formation of a yellow to orange colour indicates the presence of aglycones or glycosides in the plant tissues.

Legal's Test: To the concentrated ethanolic extract few drops of 10% NaOH were added, to make it alkaline. Then freshly prepared sodium nitroprusside was added to the solution. Presence of blue coloration indicated the presence of glycosides in the extract. 

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 CARBOHYDRATES

Molisch’s test: Small portion of the plant extract was put in a test tube; 10 ml of distilled water was added and shaken vigorously and gently. The mixture was then filters and divided into two portions. To the first portion, two drops of Molish’s reagent was added followed by few drops of concentrated sulphuric acid by the wall of the test tube. Formation of brown or purple ring at the interphase indicated the presence of carbohydrates. 

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 PHYTOSTEROLS

Libermann Burchard’s Test: Dissolve one or two crystals of cholesterol in dry chloroform in a dry test tube. Add few drops of acetic anhydride and then 2 drops of concentrated H2SO4 and mix well. The formation of a green or green-blue colour after a few minutes indicates the presence of phytosterols. After the reaction, concentration of cholesterol can be measured spectrophotometry. 

Salkowski's Test: On adding a few drops of conc. Sulphuric acid to the plant extract and allow the solution to stand for some time, formation of brown ring indicated the presence of phytosterols in the plant extract. 

TEST FOR FLAVONOIDS 

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 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. 

Shinod’s Test: In this test, four pieces of magnesium fillings (ribbon) are added to the ethanolic extract followed by a few drops of concentrated hydrochloric acid. A reddish colour indicates the presence of flavonoid.

TEST FOR FIXED OILS AND FATS

Spot test: Take the sample to be tested, press a little in the folds of the filter paper. On folding, if there is the appearance of greasy spot indicates the presence of oils or fats. The spot grows larger on heating and drying the filter paper.

Saponification: Take approximately 100 mg of oil or fat in a test tube. Add 3 mL of alcoholic-KOH and mix well. Place the tube in a boiling water bath for 15-20 min. Saponification value represents mg of potassium hydroxide required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample as triglycerides.

TEST FOR FREE AMINO ACIDS

Millon’s reagent test: Millon's test is specific to phenol containing structures (tyrosine is the only common phenolic amino acid). Millon's reagent is concentrated HNO3, in which mercury is dissolved. As a result of the reaction a red precipitate or a red solution is considered as positive test.

Ninhydrin reagent test: A 2% solution of ninhydrin is prepared by dissolving 0.2 grams of ninhydrin in 10ml of either ethanol or acetone. 1% solution of the amino acid (analyte) in distilled water is prepared, few drops of 2% ninhydrin solution is added to this solution. Test tube is kept in a warm water bath for 5 min; development of a deep blue/violet colour indicates presence of amino acids.

TESTS FOR FIXED OILS AND FATS 

Spot test Take the sample and place it between the folds of filter paper and rub it lightly. Presence of translucent spots on the filter paper confirms the presence of fats in in the plant material. 

Saponification Take a sample a test tube, add strong alkali NaOH, boil the solution in a water bath for 5 min, add ethanol. Observe for the appearance of froth, formation of forth in the test tube indicates the presence of fat in the sample. 

TEST FOR FREE AMINO ACID 

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 TANNINS 

5% Ferric chloride test: 5 mg of extract was taken and 0.5 ml of 5% ferric chloride was added. The development of dark bluish black color indicates the presence of tannins. 

10% Lead acetate test: 10 mg of extract was taken and 0.5 ml of 1% lead acetate solution was added and the formation of precipitate indicates the presence of tannins and phenolic compounds.

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.

GUMS & MUCILAGE 

Ruthenium red test: 50 mg of dried mucilage powder was dissolved in 2 mL of distilled water, mixed with a few drops of Ruthenium red solution. Observed for pink color indicates the presence of gums and mucilage.

GC-MS Analysis: 

Phyto-components were identified using GC–MS detection system as described previously, however with modification, whereby portion of the extract was analysed directly by headspace sampling. GC–MS analysis was accomplished using an Agilent 7890A GC system set up with 5975C VL MSD (Agilent Technologies, CA, and USA). Capillary column used was DB-5MS (30 m × 0.25 mm, film thickness of 0.25 μm; J&W Scientific, CA, USA). Temperature program was set as: 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. Identification of phyto-components was performed by comparison of their retention times and mass with those of authentic standards spectra using computer searches in NIST 08.L and Wiley 7n.l libraries^40,41

FTIR Analysis

Some of the sample fractions absorb light when infrared light passes through a sample. However, some frequencies are transferred through the sample without any absorption occurring. Infrared absorption is related to the vibrational changes that occur inside a molecule when it is exposed to IR. Infrared spectroscopy is a vibrational spectroscopy that can detect the variations in the vibrations in the range. Different bonds (C–C, C=C, C≡C, C–O, C=O, O–H, N–H) have altered vibrational frequencies. If these chemical bonds are present in an organic molecule, they can be identified by characteristic frequency absorption band in IR spectrum. Fourier Transform Infrared Spectroscopy is a high resolution analytical tool to identify the chemical bonds in a compound. FTIR offers a rapid and non-destructive investigation to fingerprint herbal extracts. FTIR were studied using Shimadzu spectrometer (Shimadzu, Japan). For this, 3.0 mg of sample was dispersed in 300 mg of spectroscopic grade KBr and subsequently pressed into disk at 10 MPa for 3 min. The spectra obtained were recorded with an average of 25 scans and a resolution of 4 cm^-1 in the range of 4000–400 cm^-1.

RESULTS AND DISCUSSION

                  Tomato, a widely consumed staple vegetable crop, offers a real potential to combat human nutritional deficiencies. Tomatoes are rich in micronutrients and other bioactive compounds (including vitamins, carotenoids, and minerals) known to be essential or beneficial for human health⁴¹. Preliminary phytochemical screening of SL wild fruit extracts revealed the presence of alkaloids phenols, flavonoids, tannins, steroids, and resins, in Petroleum Ether Extract (SLFPEE) Chloroform Extract (SLFCE) Methanol Extract (SLFME) (Table 1) which could be responsible for wide range of biological properties. GCMS analysis of the wild fruit juice of Solanum lycopersicum revealed the presence of following compounds (CID number – Molecular Formula given in parenthesis) 3-methylheptane (11519 - C₈H₁₈); Ethylcyclohexane (1550 - C₈H₁₆); 2-Methyl-4,6-octadiyn-3-one (562128 - C₉H₁₀O); 5,6-Dimethylundecane (519454 - C₁₃H₂₈); (3E)3-Hexen-2-one (5367744 - C₆H₁₀O); 2,2-Dimethylbutane (6403 - C₆H₁₄); 1,2-Diphenyl-1-butanone (297636 - C₁₆H₁₆O); Isopropylbenzene (2-phenylpropane) (7406 - C₉H₁₂); 3,5-Dimethyloctane (139989 - C₁₀H₂₂); 2-Phenyl-3-buten-1-ol (250465 - C₁₀H₁₂O); 2,4,4-Trimethylhexane (28024 - C₉H₂₀); Benzoylcarboxaldehyde (Phenylglyoxal) (14090 - C₈H₆O₂); Cis-3-Methyl-Endo-Tricyclo[5.2.1.0(2.6)]Decane (557024 - C₁₁H₁₈); 2,4-Dimethylhexan-3-One (85770 - C₈H₁₆O); Benzene acetic acid,2-phenylethyl ester (7601 - C₁₆H₁₆O₂); Cyclo-pentacycloheptene (9231 - C₁₀H₈); 2,3-Heptanedione (60983 - C₇H₁₂O₂); 1,6-Methano[10] annulene (139979 - C₁₁H₈Br₂); 1-Naphthaleneacetic acid, methyl ester (17891 - C₁₃H₁₂O₂); N,N-Dimethylmethanesulfonamide (70191 - C₃H₉NO₂S); Methyl tridecanoate (15608 - C₁₄H₂₈O₂); Cis 9-Octadecanoic acid (445639 - C₁₈H₃₄O₂); Methyl 15-methylheptadecanoate (554152 - C₁₉H₃₈O₂); 9-Octadecenoic acid (637517 - C₁₈H₃₄O₂); Methyl (Z)-octadec-9-enoate (5364509 - C₁₉H₃₆O₂); (Z)-octadec-9-enamide (5283387 - C₁₈H₃₅NO); Methyl 2-ethyl-2-methylicosanoate (575666 - C₂₄H₄₈O₂); 1,2,3,4,4a,5,6,7,8,9,10,11,12,12a-tetradecahydrobenzo[10]annulene (565944 - C₁₄H₂₆) (Table 2). 

Fruit juice of Solanum lycopersicum showed FTIR peaks at 2991.05, 2921.63, (N-H stretching) 2873.42, 2856.06, (CH3, CH2 & CH 2 or 3 bands) between the reference ranges 2850-3000 and 2695-2830 indicated the presence of alkanes. The peaks at 2770.24 (2695-2830), 2141.56 (2140-2175), 1716.34 (1706-1720), 1646.91, 1665.45 ((1640-1690), 1530.24, 1505.17 (1500-1550), 1454.06 (1400-1500), 1436.71 (1395-1440), 1408.75 (1380-1410), 1322.93 (1210-1390), 1246.75, 1194.69 ((1020-1250), 1070.3,1042.34 (1030-1070), 939.163, 921.807 (910-959 ) and 897.701 (675-900) specifies the presence of aldehydes & ketones, thiocyanate, carboxylic acid, imine/oxime, nitro compound, aromatic, carboxylic acid, sulfonyl chloride, phenol, alkyl aryl ether, sulfoxide, carboxylic acids and aromatics respectively. The peaks at 828.882, 821.527 (550-850), 700.998 (610-700) and 590.111 (515-690) represents the existence of alkyl halides and alkynes (Table 3; Fig. 1). Presence of these functional groups in the sample analysed signifies the presence of phytocompounds and nutrients such as potassium, folic acids, neoxanthin, lutein, α-cryptoxanthin, α-carotene, β-carotene, cyclolycopene, and β-carotene 5, 6-epoxide as indicated by 42.           Faria-Silva et al.⁴², flavonoids, vitamin C, hydroxycinnamic acid derivatives and anti-oxidative and anti-cancer phyto compound lycopene’s⁴³. ADMET prospecting these bioactive molecules in SL could pave way for the successful exploitation of the PBNPs in the days to come^44-49.

CONCLUSION 

Tomato has high global demand and hence widely cultivated fruit world-over. It has a unique savoury flavour, rich nutrient content and health-promoting properties. Tomato fruit juice is a rich source of natural products with bioactives which are ultimately responsible for health promoting activities. In vitro and in vivo studies with animal models along with human cell lines have demonstrate that tomato fruit has compounds with antiplatelet, antioxidant, anticancer, antimutagenic, antimicrobial, and neuroprotective activities. However, further research is warranted to unravel in-depth molecular mechanism underlying with bioactivities of PBNPs in tomato. Furthermore, information on bioavailability and bioaccessibility of compounds from tomato in human body is far lacking. Therefore, ADMET evaluation with regard to the safety and efficacy of bioactive compounds is expected expand the capabilities of PBNPs in tomato for its utilization in the functional food, cosmeceutical and health-care (pharmaceutical) industries.

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46. Loganathan T, Barathinivas A, Soorya C, Balamurugan S, Nagajothi TG, Ramya S, Jayakumararaj R. Physicochemical, Druggable, ADMET Pharmacoinformatics and Therapeutic Potentials of Azadirachtin-a Prenol Lipid (Triterpenoid) from Seed Oil Extracts of Azadirachta indica A. Juss. Journal of Drug Delivery and Therapeutics. 2021 Sep 15; 11(5):33-46. https://doi.org/10.22270/jddt.v11i5.4981

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Table 1: Qualitative Phytochemical Examination with solvent plant extracts

Note: + indicates positive result; - indicates negative result

Table 2: GCMS profile of Solanum lycopersicum Fruit Methanol Extract

Table 3: FTIR spectra of functional groups in SLFME sample 

Figure 1: FTIR spectra of functional groups in SLFME sample