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GC-MS ANALYSIS OF BIOACTIVE COMPOUNDS FROM ETHANOLIC LEAF EXTRACT OF WALTHERIA INDICA LINN. AND THEIR PHARMACOLOGICAL ACTIVITIES

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GC-MS ANALYSIS OF BIOACTIVE COMPOUNDS FROM ETHANOLIC LEAF EXTRACT OF WALTHERIA INDICA LINN. AND THEIR PHARMACOLOGICAL ACTIVITIES

Prabhanna Banakar * and M. Jayaraj

P. G. Department of Botany, Karnatak University, Dharwad - 580003, Karnataka, India.

ABSTRACT: Bioactive compounds are the frontline potent agents in both nutraceutical and pharmaceutical industries. Recently, the bioactive compounds are gaining much importance for their ability in enhancing resistance to various diseases and to improve the health of people both by traditional and modern ways of administrations. Therefore, in the present investigation was undertaken to identify the compounds present in the leaf of Waltheria indica Linn. by Gas Chromatography-Mass Spectrometry (GC-MS) analysis by ethanol extract. The GC-MS analysis showed 27 bioactive compounds. The major compounds identified are 2,3-Dihydro-3,5-Dihydroxy-6-methyl-4h-pyran-4-one, tetradecane, nonadecane, tetracosane, phytol and squalene. In a mass spectrum, each compounds were identified based on their retention time and peak area. Pharmacological activities of these compounds indicated that the compounds present in the leaf of said plant can be used as a crude drug and can also be used to develop a novel drug.

Keywords:

Bioactive compounds, Ethanolic leaf extract, GC-MS, Pharmacological activity, Sterculiaceae, Waltheria indica L.

INTRODUCTION: The pharmaceutical industries are using bioactive compounds as potent agents in treatment of many diseases. In the recent days bioactive compounds are gaining importance for their ability to cure many diseases. India has a rich heritage of medicinal plants 1. Plants have the capacity of synthesizing the organic compounds and are called as secondary metabolites, they have unique and complex structures. The secondary metabolites are used in the treating of chronic as well as infectious diseases 2. Waltheria indica L. is a highly valued medicinal plant used to treat the cancer 3, 4, malaria 5 and viral 6 diseases. It also possesses the antimicrobial 7, antioxidant 8, anti-inflammatory 8 and analgesic 8 actions.

Traditionally it is also used to treat wound healing9, sleeping sickness 10 and cough 9. Overall the plant is considered as febrifugal, purgative and emollient 9.  In the last few years, the GC-MS has become the key tool for secondary metabolite profiling in plants. However, there are few reports are available on the pharmacological properties of the plant. Keeping this in view, the present study is undertaken to establish the GC-MS profile of ethanolic leaf extract of Waltheria indica Linn. and their pharmacological activities.

MATERIALS AND METHODS:

Material: Waltheria indica Linn. belongs to the family Sterculiaceae11. It is an under shrub growing in sub tropical and tropical regions including in India. It is commonly known as velvet leaf, marsh mallow and monkey bush 12. The Waltheria indica Linn. (Voucher specimen no: PB/MJ/01) leaves were collected from the plants grown in Karnatak University Campus, Dharwad, Karnataka. The leaves were washed with running tap water and later dried at room temperature.

The dried leaves were powdered using an electric blender. The powder obtained was sieved and stored in an air tight container at room temperature till further analysis 13.

Leaf Extract: About 10gms of dried and coarsely powdered leaves were subjected to extraction with ethanol (250 ml) using Soxhlet apparatus. The extract was subjected to GC-MS analysis 13.

GC - MS Analysis: The analysis was performed using a GC-MS (Shimadzu, Kyoto): QP2010S fitted with a 1.4 μm column Rxi-5silMS 30 meter length, 0.25 mm inner diameter and 0.25 μm film thickness. Carrier gas helium with a flow rate of 0.98 ml/min; column temperature 80 °C; initial temperature 70 °C, injector temperature 260 °C and detector temperature 300 °C, followed by a linear programmed temperature from 70 - 280 °C at a rate of 10 °C/min, operating in electron impact mode.

The samples were injected in splitless mode. Interface temperature was kept at 280 ºC. Oven temperature programming was done from 80 °C - 260 ºC at 10 ºC /min. The pressure of the carrier gas was kept at 63.6 kPa. The constituents were identified based on the RT values using the NIST 11 and WILEY 8 library 14.

Identification of Components: Bioactive com-pounds are identified based on interpretation on mass spectrum of GC - MS using the database of National Institute Standard and Technology (NIST11) and WILEY 8. The mass spectrum of the unknown component was compared with the spectrum of the known components stored in the NIST 11 and WILEY 8 library 15. The name, molecular weight and molecular formula of the components of the test materials were tabulated.

RESULTS: The GC - MS chromatogram of the ethanolic leaf extract of Waltheria indica Linn. showed 27 peaks indicating the presence of twenty seven compounds (Fig. 1).

The active principles with their peak, retention time (RT), area (%), height (%), molecular formula and molecular weight are presented in the Table 1.

The tetradecane, hexadecane, squalene, 2,3-Dihydro-3,5-Dihydroxy-6-methyl-4H-pyran-4-one showed maximum per-centage. The 2-propenoic acid, 10- Heneicosene (c.t), Nonadecane, 3-Eicosene, (E)-, 1,1 Bicyclo propyl-2-octanoic acid, megasti-gmatrinone-4 showed a moderate percentage. The minimum percentage compounds are 1-docosanol, 3',5'-Di-methoxyacetophenone, 2-Hexadecen-1-Ol, 3,7,11, 15-Tetramethyl-, [R-[R*,R*-(E)]]-, Z,Z-8,10-Hexa-decadien-1-ol, phytol, tetracosane, 2- bromodecane, 5,5, Diethyl hepta-decane.

The GC - MS identified compounds shows various pharmacological activities and are ascertained as in the Table 2.

FIG. 1: CHROMATOGRAM OF GC - MS ETHANOLIC LEAF EXTRACT

TABLE 1: GC-MS ANALYSIS OF BIOACTIVE COMPOUNDS IN ETHANOL LEAF EXTRACT OF WALTHERIA INDICA LINN.

Peak R.

Time

 Area

%

 Height

%

 Molecular formula Molecular weight

(g/mol)

 Name of the

 compound
1 4.609 5.65 2.89 C3H6N6 126.2 1,3,5-Triazine-2,4,6-Triamine
2 5.464 7.67 3.21 C6H8O4 144.12 2,3-Dihydro-3,5-Dihydroxy-6-methyl-4H-pyran-4-one
3 8.698 18.21 11.55 C14H30 198.39 Tetradecane
4 9.632 2.58 2.77 C17H36O 256.46 1-Hexadecanol, 2-Methyl-
5 10.734 1.67 2.05 C10H12O3 180.20 3',5'-Dimethoxyacetophenone
6 11.158 11.91 17.28 C16H34 226.44 Hexadecane
7 11.563 2.23 2.10 C13H18O 190.28 Megastigmatrienone 4
8 11.852 2.79 2.16 C21H38O2 322.53 [1,1'-Bicyclopropyl]-2-octanoic acid, 2'-hexyl-, methyl ester
9 12.208 3.79 5.09 C16H30O2 254.41 2-Propenoic acid, tridecyl ester
10 13.324 2.92 2.89 C20H40 280.54 3-Eicosene, (E)-
11 13.398 7.53 10.75 C18H38 254.50 OCTADECANE
12 13.788 1.39 2.11 C20H40O 296.53 2-Hexadecen-1-ol, 3,7,11,15-Tetramethyl-, [R-[R*,R*-(E)]]-
13 14.373 0.79 1.29 C19H38 266.51 1-Nonadecane
14 15.158 0.60 0.70 C12H25Br 249.23 2-Bromo dodecane
15 15.375 3.11 2.53 C21H42 294.55 10-Heneicosene (c,t)
16 15.435 3.10 4.77 C19H40 268.52 Nonadecane
17 15.475 0.34 0.63 C21H44 296.57 5,5-Diethylheptadecane
18 16.329 0.84 1.29 C36H75O3P 586.95 Phosphonic acid, Dioctadecyl ester
19 16.489 1.02 1.37 C20H40O 296.53 Phytol
20 16.942 1.06 1.46 C14H23F3O2 280.32 trans-2-Dodecen-1-ol, trifluoroacetate
21 16.994 1.18 1.76 C16H30O 238.41 Z,Z-8,10-Hexadecadien-1-ol
22 17.243 1.69 1.20 C22H46O 326.60 1-Docosanol
23 17.296 1.01 1.72 C24H50 338.66 Tetracosane
24 18.002 0.83 1.22 C26H52 364.70 Cyclopentane, Heneicosyl-
25 18.125 1.08 1.22 C21H35F7O2 452.49 Heptadecyl heptafluorobutyrate
26 18.961 0.84 1.42 C26H52 364.69 Cyclohexane, Eicosyl-
27 22.796 8.48 8.30 C30H50 410.71 Squalene

TABLE 2: PHARMACOLOGICAL ACTIVITY OF PHYTOCOMPONENTS IN THE ETHANOLIC EXTRACT OF WALTHERIA INDICA LINN. LEAF

Name of the compound Pharmacological activity
1,3,5-Triazine-2,4,6-Triamine Antagonists 16, Cytotoxicity against leukemia and adenocarcinoma 17 Inhibites glucocerobrosidese 18, Antileismenial activity 19, Anti-HIV 20, Antimalarial 21 Antioxidant, Cancer preventive 21 Antimicrobial 22
2,3-Dihydro-3,5-Dihydroxy-6-Methyl-4H-Pyran-4-One Antioxidant 1, Antimicrobial 1, Automatic nerve activity, Anti-inflammatory 23, Antiproliferative 24, 25, Anti-arthritic 26, Anticancer, Antidiabetic 1, Pro-apoptic effects 24
Tetradecane Antimicrobial 27, Cytotoxicity 28, Antipyretic, Anthelmentic, Tumour, Bronchitis, Asthma, Tuberculosis, Dyspepsia, Constipation, Anemia, Throat diseases, Elephantiasis, Antidiabatic, Anti-inflammatory, Antidiarrhoeal 29
1-Hexadecanol, 2-Methyl- Antimicrobial 30
3',5'-Dimethoxyacetophenone No activity reported
Hexadecane Cytotoxicity 28, Antimicrobial, Antioxidant 31, Antipyretic, Anthelmentic, Tumour, Bronchitis, Asthma, Tuberculosis, Dyspepsia, Constipation, Anemia, Throat diseases, Elephantiasis, Antidiabetic, Anti-inflammatory, Antidiarrhoeal 32
Megastigmatrienone - 4 Aroma Nature 33, Cytotoxic Activity 34
[1,1'-Bicyclopropyl]-2-octanoic acid, 2'-hexyl-, methyl ester Antidiabatic, Anticancer 35, Haemolytic, Pesticide, Skin irritant, Hypocholesterolemic 32
2-Propenoic acid, tridecyl ester No activity reported
3-Eicosene, (E)- Antimicrobial, Antihyperglycemic 36, Cytotoxic Activity 36, 28, Antioxidant,

Insecticidal activity 37
Octadecane Antioxidant, Anti-inflammatory 38 Cough, lung diseases, Cold and fever detoxification 39, Anticorrosion agent 23, Antisepsis 40
2-Hexadecen-1-ol, 3,7,11,15-Tetramethyl-, [R-[R*,R*-(E)]]- Anti-inflammatory, Antimicrobial, Cancer-preventive 41 Antitumor, Analgesic, Antibacterial, Anti-inflammatory, Fungicide 42
1-Nonadecane Antimicrobial, Antioxidant, Anticancer 43
2-Bromo dodecane Antibacterial activity 44
10-Heneicosene (c,t) No activity reported
Nonadecane Anti HIV, Antioxidant, Antibacterial 45, Antimicrobial 27,

Cytotoxic effect, Antimicrobial 46, 27 Antimalarial 47, Unini uses like

weakness of the principal organs like heart, Brain, liver, General weakness,

Haemoptysis, Palpitation, Conjunctivitis, Earache, Stomatitis 48
5,5-Diethylheptadecane No activity reported
Phosphonic acid, Dioctadecyl ester No activity reported
Phytol Antimicrobial 32, Anti inflammatory 32, Anticancer 32, Diuretic,

Antifungal against S. typhi, Resistant gonorrhea, Joint

dislocation, Headache, Hernia, Stimulant and antimalarial 49
trans-2-Dodecen-1-ol, trifluoroacetate No activity reported
Z,Z-8,10-Hexadecadien-1-ol No activity reported
1-Docosanol Antimicrobial 50, Emollient, Emulsifier, Thickener in Cosmetics 51

Antiviral 52, Antitumor activity 53
Tetracosane Cytotoxicity against cancerous cells 54, Antidiarrheal 55, Antibacterial 35, Cardiotonic, laxative, Anthelemntic and removes fatigue, Anti-inflammatory, used in peptic ulcer treatment 56 Anticorrosive, Antioxidant 49, Antitrichomonas 57
Cyclopentane, Heneicosyl- No activity reported
Heptadecyl heptafluorobutyrate No activity reported
Cyclohexane, Eicosyl- No activity reported
Squalene (Antibacterial, Antioxidant, Antitumor, Cancer preventive, Immunostimulant,

Chemo preventive, Lipoxygenase-inhibitor, Pesticide) 58, 41

DISCUSSION: The GC-MS analysis revealed the 27 chemical compounds. The tetradecane (18.21%) is the highest chemical compound and 5,5 Di-ethylheptadecane (0.34%) as the lowest chemical compound. The compound 2,3-Dihydro-3,5-Di-hydroxy-6-methyl-4H-pyron-4-one, tetradecane, Hexadecane, 2-Hexadecen-1-ol, 3,7,11,15-Tetra-methyl-, [R-[R*,R*-(E)]]-, showed pharmacological activity as reported in the plants of Hibiscus tiliaceus Linn.1, Marsilea quadrifolia Linn.25 and Gymnema sylvestre (Retz) Schult 35. Similarly, phytol and squalene also showed the various biological activities as reported for Coldenia procumbens Linn.2 However, isolation and charac-terization of individual phytochemical constituents may proceed to discover the novel drugs and their pharmacological activities.

CONCLUSION: The ethanolic leaf extract of Waltheria indica Linn. has 27 different chemical compounds and they have different pharma-cological activities. Each chemical compound can be extracted individually and can be used in clinical trials to check efficacy, and to develop a novel drug from a crude drug. The GC-MS analysis of leaf extract will also be a part of database of bioactive products of natural drugs.

ACKNOWLEDGEMENT: Authors acknowledge the Chairman, P. G. Department of Botany Karnatak University, Dharwad, USIC Karnatak University, Dharwad for facilities and financial assistance to one of the authors in the form of UGC-URS fellowship. KFRI Trissur, Kerala for GC-MS analysis.

CONFLICT OF INTEREST: We have no conflict of interest.

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    How to cite this article:

    Banakar P and Jayaraj M: GC-MS analysis of bioactive compounds from ethanolic leaf extract of Waltheria indica Linn. and their pharmacological activities. Int J Pharm Sci Res 2018; 9(5): 2005-10.doi: 10.13040/IJPSR.0975-8232.9(5).2005-10.

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Article Information

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2005-2010

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IJPSR

P. Banakar* and M. Jayaraj

P. G. Department of Botany, Karnatak University, Dharwad, Karnataka, India.

prabhu999.banakar@gmail.com

10 August, 2017

17 October, 2017

20 October, 2017

10.13040/IJPSR.0975-8232.9(5).2005-10

01 May, 2018

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