PHYTOCHEMICAL CHARACTERIZATION OF COLD MACERATED METHANOLIC LEAF EXTRACT OF CADABA INDICA LAM. USING GC-MSHTML Full Text
PHYTOCHEMICAL CHARACTERIZATION OF COLD MACERATED METHANOLIC LEAF EXTRACT OF CADABA INDICA LAM. USING GC-MS
V. Thirumalai 1, P. Nirmala * 1 and R. Venkatanarayanan 2
Department of Pharmacology 1, Rajah Muthiah Medical College, Annamalai University, Chidambaram - 608002, Tamil Nadu, India.
Department of Pharmacognosy 2, R. V. S. College of Pharmaceutical Sciences, Sulur, Coimbatore - 641402, Tamil Nadu, India.
ABSTRACT: Cadaba indica Lam (Indian Cadaba), an Indian traditional medicinal plant has been used for various diseases. The cold macerated methanolic leaf extract of Cadaba indica was assessed using Agilent GC 7890A gas chromatography connected with an MS- 5975C mass spectrometer and the mass spectra were matched with NIST 14.0 – data library. Several chemical constituents were identified within 28 min of the entire GC-MS analysis. The GC chromatogram shows that presence of most abundant linolenic acids and its esters such as Hexa-decanoic acid, methyl ester, n-hexadecanoic acid, 10,13-octadecadienoic acid, methyl ester, 9, 12, 15-Octadecatrienoic acid, (Z, Z)-methyl ester, Octadecanoic acid, methyl ester, 9, 12-Octadecadienoic acid, (Z, Z)-, 9, 12, 15-Octadectatrionic acid, (Z, Z, Z)-,Octadecanoic acid, Hexadecanoic acid, 2,3-dihydroxy propyl ester and 9- Octadecanoic acid, (Z) – methyl ester. In contrast, compounds with diterpenes, phthalic esters, pyrrolidine, phenol, ketones, and myristic acid derivatives were also detected with average peak area percentage. The nature and chemical background of the detected phytochemical constituents may be responsible for the pharmacological effects of Cadaba indica Lam. in various diseases.
Cadaba indica Lam, Cold maceration, Gas chromatography, Linolenic acid, Phytochemical constituents, GC-MS analysis
INTRODUCTION: Phytotherapy, a branch of medicine, deals with the application of plants and their products in the prevention and treatment of several diseases. Since the ancient days, several medicinal systems such as Ayurveda, Siddha, Chinese traditional medicine, Unani, naturopathy, anthroposophic medicine, and homeopathy are practicing phytomedicine to treat the various conditions 1. Besides, as per the World Health Organization (WHO), about 2500 plants are being used for the treatment of various diseases 2.
Traditional medicinal plants are mainly preferred due to their safety, accessibility, affordability, and faith. In this instance, validation and standardization of their pharmacological effects are essential to ensure the safety and efficacy of herbal medicines. Plants are naturally containing several phytochemical constituents which are responsible for their medicinal properties 3-6.
Hence, the phytochemical profiling of secondary metabolites is primarily required to assess their pharmacological actions 5, 6. Gas chromatography-mass spectrometry is one of the advanced techniques to determine the volatile phytochemical compounds of the herbal plant samples 7. Cadaba indica Lam. is a tropical and subtropical region plant that belongs to the family Capparidaceae (Capparaceae). Cadaba indica, also known as Veezhi or vizhuthi in Tamil which was first described by Pulipani siddhar in his book “Jala thirattu”. The Ayurvedic and Siddha medicine system prescribed this leaf juice for the treatment of dysentery, fever, swelling, cough, lung problem and worm infestation. Also, this plant was known to medicine for treating menstrual irregularities, ovarian cysts, and other female infertility problems 8-11. Cadaba indica Lam. methanolic leaf extract contains phenol, flavonoid, saponin, steroid, protein, and carbohydrate 12. At the same time, the aerial parts have already been reported with a sensible amount of total phenol and flavonoids 13. The antioxidant 13, anti-inflammatory 12, 14, analgesic 14, anti-microbial 15, and antipyretic 16 activities also established with various solvent extracts of Cadaba indica Lam. This present study aimed to detect and characterize the phytochemical constituents in cold macerated methanolic leaf extract of Cadaba indica Lam by gas chromate-graphy-mass spectrometry method.
MATERIALS AND METHODS:
Collection of Plant Material: The plant Cadaba indica was collected during the flowering season in February 2017 from, Melur, Madurai district, Tamil Nadu, India. The proposed plant was authenticated by Dr.V.Chelladurai, Formerly Research Officer of Botany, Central Council for Ayurveda and Siddha, Government of India. A voucher specimen (Dated 20/03/2017) was preserved in the laboratory for future reference.
Preparation of Plant Leaf Extract: In a cold maceration method, 100 g of Cadaba indica leaf powder was soaked in petroleum ether in a closed glass jar for 72 h. Such defatted material was subjected to methanol extraction. The extracted plant material was then filtered and dried under reduced pressure in Eyele Rotary evaporator (Japan) at room temperature to a viscous mass, weighed, and stored at 4 ºC for further analysis.
Procedure: The chemical constituents of cold macerated methanolic leaf extract of Cadaba indica analyzed using Agilent GC 7890A gas chromate-graphy connected with an MS- 5975C mass spectrometer instrument detector. Autosampler system-7693 (ALS 7693) was used in the sample injection process. Helium, a carrier gas used at 1ml/minute constant flow rate, and the splitless flow rate was 1 ml/min.
The capillary column used in this experiment was a DB-5MS non-polar capillary column (5% diphenyl, 95% dimethyl polysiloxane) with dimensions of 30 m length, 0.25 mm inner diameter, and 0.25 µm of film thickness. The initial oven temperature was kept as 50 ºC for 1 min and programmed to reach 300 ºC held for 2 min. The total run time of 28 min was programmed for the analysis, and the injection volume was 1 µl.
The detector operated in 50-550 mass range with 0.5s scan interval. The obtained chromatogram of plant extract was analyzed in mass spectrometry to identify the mass of detected fractions. Eluted chemical constituents were further identified based on the retention time and mass spectra. The comparison of eluted compounds made with standard mass spectra data library- National Institue of Science and Technology (NIST)-14.0 versions to determine the name, molecular weight, and structure of the eluted chemical constituents.
RESULTS: The cold macerated methanolic leaf extract of Cadaba indica (CICME) was analyzed in gas chromatography-mass spectrometry (GC-MS) to identify the bioactive compounds that responsible for its pharmacological actions. After 28 min of a complete run, 40 peaks were obtained, as shown in the chromatogram Fig. 1. The eluted bio-active compounds were characterized by retention time (RT), peak area, and peak area percentage (%). However, the mass spectrum was used to identify the structure of eluted chemical constituents by its database NIST-14.0 library.
Among the several chemical constituents, sixteen peaks with moderate to higher concentrations were selected for the data analysis. The first compound obtained was 2-pentene, 3-methyl-, (E)- at 6.523 min of retention time.
Consecutively, 1,Methyl-pyrrolidine-2-carbo-xylic acid (5.10%), 2-Methoxy-4-vinyl phenol (0.72%), Tetradecanoic acid (1.06%), 2 – penta - de-canone,6,10,14- trimethyl- (0.92%), Hexa-decanoic acid methyl ester (3.56%), n-Hexadecanoic acid (27.56%), 10,13-octa-decadienoic acid methyl ester (1.28%), 9,12,15-Octadecatrienoic acid, (Z, Z)-methyl ester (4.71%), Phytol (3.36%), Octadecanoic acid, methyl ester (0.88%), 9,12-Octadecadienoic acid, (Z, Z)-(5.34%), 9,12,15-Octadectatrionic acid, (Z,Z,Z)- (19.75%), Octa-decanoic acid(4.77%), Hexa-decanoic acid, 2,3-dihydroxy propyl ester (1.94%), 1,2 Benzene dicarboxylic acid, mono (2-ethylhexyl) ester (1.35%), 9- Octadecanoic acid, (Z) – methyl ester (1.05%) were identified and the molecular formula, molecular weight and nature of the compound were also tabulated in Table 1 and 2. The pharma-cological activities of the identified compounds were tabulated in Table 2 as per previously published phytochemical and ethnopharma-cological studies.
TABLE 1: PHYTOCHEMICAL CONSTITUENTS OF COLD MACERATED METHANOLIC LEAF EXTRACT OF CADABA INDICA LAM.BY GC-MS SPECTRA
FIG. 1: GC-MS CHROMATOGRAM OF COLD MACERATED METHANOLIC LEAF EXTRACT OF CADABA INDICA LAM
TABLE 2: PHARMACOLOGICAL ACTIVITY AND NATURE OF IDENTIFIED PHYTOCHEMICAL CON-STITUENTS IN COLD MACERATED METHANOLIC LEAF EXTRACT OF CADABA INDICA LAM
|S. no.||Compound Name||Nature of the Compound||Pharmacological Activity|
|1||1,Methyl-pyrrolidine-2-carboxylic acid||pyrrolidine||Antifungal and anti-bacterial 17|
|2||2-Methoxy-4-vinyl phenol||Phenolic compound||Anti-inflammatory 18 and anti-cancer 19|
|3||Tetradecanoic acid||Myristic acid||Antioxidant, anti-cancer, hypocholesterolemic, nematicide 20|
|4||2-pentadecanone,6,10,14- trimethyl-||Ketone||Anti-inflammatory, wound healing, and anti-bacterial 21|
|5||Hexadecanoic acid, methyl ester||Linolenic acid ester||Anti-inflammatory, anti-cancer, hepatoprotective, anti-arthritic, anti-androgenic and anti coronary activity 20|
|6||n-Hexadecanoic acid||Linolenic acid||Anti-inflammatory, antioxidant, hypocholesterolemic and anti-androgenic 20,22,23|
|7||10,13-octadecadienoic acid,methyl ester||Linolenic ester||Anti-inflammatory, anti-arthritic, hypocholesterolemic, hepatoprotective, antihistamine activity 20|
|8||9,12,15-Octadecatrienoic acid, (Z, Z)-methyl ester||Linolenic acid ester||Anti-inflammatory, hypocholesterolemic, hepatoprotective, and anti-cancer 24|
|9||Phytol||Diterpene||Anti-inflammatory, anti-cancer, antioxidant, diuretic, and anti-microbial 25-28|
|10||Octadecanoic acid, methyl ester||Linolenic acid ester||Anti-tumor, cytotoxic and anti-microbial 29,30|
|11||9,12-Octadecadienoic acid, (Z, Z)-||Linolenic acid||Anti-inflammatory, anti-cancer, anti-arthritic, antihistaminic, and hypocholesterolemic 20,24|
|12||9,12,15-Octadecatrionic acid,(Z,Z,Z)-||Linolenic acid||Anti-arthritic, anti-inflammatory, anti-acne, hepatoprotective, hypocholesterolemic 24,31|
|13||Octadecanoic acid||Linolenic acid||Antifungal, antibacterial and anti-tumor 32|
|14||Hexadecanoic acid, 2,3-dihydroxy propyl ester||Linolenic acid ester||Anti-inflammatory and NF-κB inhibitory action 33|
|15||1,2 Benzene dicarboxylic acid, mono (2-ethylhexyl) ester||Phthalic ester||Anti-cancer and
cytotoxic activity 34
|16||9- Octadecanoic acid, (Z) – methyl ester||Linolenic acid ester||Anti-inflammatory, antiandrogenic, anti-cancer, antioxidant and anti-fungal 20,35|
DISCUSSION: Cadaba indica Lam. methanolic leaf extract was prepared by cold maceration method in this study. Cold maceration is a simple method to extract any raw materials without loss of thermolabile bioactive compounds due to low temperature 36. Ramakrishnan et al. reported that the availability of phytochemicals was higher in soxhlet methanolic extract of Cadaba indica leaves than other solvent extracts 12. Mohan VR et al. reported the level of total phenol and flavonoid content in aerial parts of Cadaba indica. They found out that the level of phenol and flavonoids were relatively higher in methanolic extract than other aromatic solvents 13. Thirumalai et al. quantified the amount of rutin, gallic acid, and quercetin in various types of extracts of Cadaba indica leaf, and reported that quercetin, gallic acid, and rutin were found to be in higher quantities in cold macerated methanolic leaf extract than in hot percolation method 37.
In this present study, the cold macerated methanolic extract was subjected to the Gas chromate-graphy-Mass spectrometry (GC-MS) analysis to identify the secondary metabolites. The gas chromatogram exhibits the concentration of eluted compounds as a function of retention time (RT). The chromatogram peaks show the detected chemical constituents. The height of the peaks represented the concentrations of eluted chemical constituents. Mass spectrum of a compound is a graphical representation of ion distribution by their mass and charge ratio (m/z) which is essential in the identification of chemical structure and its characters as well.
Among the several chemical constituents identified, n-hexadecanoic acid has the highest peak area (concentration) of 27.65%. This compound is linolenic acid in nature and also called palmitic acid. However, it occurs in most natural sources and is responsible for their medicinal uses. Earlier studies reported that n-hexadecanoic acid has anti-inflammatory, antioxidant, anti-androgenic, and hypocholesterolemic activities 20. n-hexadecanoic acid suppresses the inflammatory process by its inhibitory action of phospholipase A2 enzyme 23. Palmitic acid inhibits the invasion of macrophages; hence this may reduce the accumulation of macrophages in the synovial fluid of the arthritic joint 38.
Besides, in-silico cytotoxicity studies suggested that n-hexadecanoic acid interacts with DNA topoisomerase-1 enzyme and produces cytotoxic effects which are responsible for its anti-cancer activity 22. 9, 12, 15- Octadectatrionic acid (Z, Z, Z)- is an alpha-linolenic acid compound with 19.75% peak area, which is the second major chemical constituent of Cadaba indica methanolic leaf extract. It has anti-inflammatory, antioxidant, anti-cancer, hepatoprotective, hypocholesterolemic, and anti-acne activities 31. 9, 12, 15- Octa-dectatrionic acid (Z, Z, Z)- also inhibits the synthesis of prostaglandin and leukotrienes from an arachidonic acid pathway, which plays an essential role in inflammation 24. Phytol is a diterpenoid, a notable bioactive compound in medicinal plants. Previous reports suggested that phytol has anti-inflammatory, antioxidant, anti-arthritic, anti-cancer, diuretic, and antimicrobial activities 26, 27.
Phytol interacts with the nuclear factor kappa –B (NF-κB) signaling pathway and migration of neutrophils into inflammation sites that further causes the inhibition of pro-inflammatory cytokines such as TNF-α and interleukin -6, hence can regulate the inflammatory process of arthritis 25, 28. 2-methoxy-4-vinyl phenol a phenolic compound that has anti-inflammatory and anti-cancer activity. The anti-inflammatory activity may be due to the suppression of NF-κB and mitogen-activated protein kinase (MAPK) signaling pathway. However, this effect results in the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) enzymes 18.
Tetradecanoic acid, a saturated fatty acid (myristic acid) that was identified in the extract, has antioxidant, anti-cancer activity, and hypochole-sterolemic activities 20. Whereas a ketone compound, 2-pentadecanone 6, 10, 14- trimethyl- with anti-inflammatory, wound healing, and antibacterial activity 21 was also identified with 0.92% peak area in this extract (CICME). A phthalic ester compound, 1, 2-benzene dicarboxylic acid, mono (2-ethylhexyl) ester has previously been reported with anti-cancer and cytotoxic activities 34. Some of the compounds identified in the extract such as 1-methyl-pyrrolidine-2-carboxylic acid 17, Octadecanoic acid 32, 9- Octadecanoic acid, (Z) – methyl ester, have been reported to have antifungal and antibacterial activities 20, 35.
Linolenic acid and its esters are the most common chemical constituents detected in the methanolic leaf extract of Cadaba indica (CICME). Earlier reports revealed that these compounds have potent anti-inflammatory, anti-cancer, and antioxidant activity 24. Linolenic compounds such as n-hexa-decanoic acid (27.65%), 9, 12-Octa-decadienoic acid, (Z, Z) - (5.34%), 9, 12, 15-Octadecatrieonic acid,(Z, Z, Z)-( 19.75%) and Octadecanoic acid (4.77%) are more common in several medicinal plants. However, these secondary metabolites are responsible for their pharmacological actions such as anti-inflammatory, antioxidant, and anti-cancer activities 20, 22, 38. Additionally, octadecanoic acid has antibacterial and antifungal activities 32. Whereas 9, 12-Octadecadienoic acid, (Z, Z) - possess anti-histaminic activity 20 and the compound, 9,12,15-Octadecatrionic acid,(Z, Z, Z)- has hepato-protective activity 31.
Hexadecanoic acid, methyl ester (3.56%), 10,13-octadecadienoic acid, methyl ester (1.28%), 9,12,15-Octadecatrienoic acid, (Z, Z)-methyl ester (4.71%), Octadecanoic acid, methyl ester (0.88%), Hexadecanoic acid, 2,3-dihydroxy propyl ester (1.94%),9- Octadecanoic acid, (Z) – methyl ester (1.05%) are the linolenic acid esters identified in this extract (CICME). Esters of linolenic acid also have anti-inflammatory, anti-cancer, and hypo-cholesterolemic activities with additional hepato-protective and anti-androgenic effects 24, 35. Among these ester compounds, octadecanoic acid, methyl ester has a cytotoxic activity as reported by the previous studies 30. Whereas hexadecanoic acid, 2, 3-dihydroxy propyl ester interacts with NF-κB signaling pathway and inhibits the production of pro-inflammatory mediators 33.
9, 12, 15-Octadecatrienoic acid, (Z, Z, Z); n-hexadecanoic acid; phytol; 1, methyl pyrrolidine-2-carboxylic acid and 1, 2-benzene dicarboxylic acid – mono (2- Ethylhexyl) ester are such bioactive compounds which were identified in this methanolic leaf extract of Cadaba indica and are also found in the various plants of Capparidacea family such as Cadaba trifoliate 39, 40, Cadaba fruticosa 27 and Capparis spinosa 41.
The gas chromatogram of the methanolic leaf extract of the proposed plant revealed that more than ten bioactive compounds are having anti-inflammatory, anti-arthritic and antioxidant activities. These compounds are present in higher concentrations (peak area percentage) and may contribute to the anti-inflammatory and anti-arthritic activity of Cadaba indica.
CONCLUSION: Gas chromatography-Mass spectrometry is one of the standard analytical techniques to characterize the phytoconstituents present in herbal plants. In this present study, the results reveal that the detected active compounds in cold macerated methanolic leaf extract of Cadaba indica Lam. are responsible for its pharmacological effects. Notably, detected compounds with anti-inflammatory, anti-arthritic, and antioxidant activities might be responsible for their folklore medicinal uses in chronic inflammatory conditions. Further investigations are required to assess the safety and efficacy of this traditional herbal plant in various disorders.
ACKNOWLEDGEMENT: We acknowledge our sincere thanks to Dr. R. Arivukarasu, M. Pharm. Ph.D., Department of Pharmacognosy, KMCH College of Pharmacy, Coimbatore-641048 for his timely help in this research work.
CONFLICTS OF INTEREST: The authors declare that they have no conflicts of interest.
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How to cite this article:
Thirumalai V, Nirmala P and Venkatanarayanan R: Phytochemical characterization of cold macerated methanolic leaf extract of Cadaba indica Lam. using GC-MS. Int J Pharm Sci & Res 2021; 12(6): 3185-92. doi: 10.13040/IJPSR.0975-8232.12(6).3185-92.
All © 2013 are reserved by the International Journal of Pharmaceutical Sciences and Research. This Journal licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported License.
V. Thirumalai, P. Nirmala * and R. Venkatanarayanan
Department of Pharmacology, Rajah Muthiah Medical College, Annamalai University, Chidambaram, Tamil Nadu, India.
28 May 2020
12 October 2020
02 May 2021
01 June 2021