SPECTRAL ANALYSIS OF PETROLEUM ETHER AERIAL PART EXTRACT OF GRANGEA MADERASPATANA USING GAS CHROMATOGRAPHY-MASS SPECTROMETRY

SPECTRAL ANALYSIS OF PETROLEUM ETHER AERIAL PART EXTRACT OF GRANGEA MADERASPATANA USING GAS CHROMATOGRAPHY-MASS SPECTROMETRY

Jyoti Pathak *, Pratap Singh Shekhawat, Harsha Rishi and Sangeeta Bhargava

Government College, Kotputli, Rajasthan, India.

ABSTRACT: Grangea maderaspatana, commonly known as Madras carpet / Indian chickweed and belonging to the Asteraceae family. This plant is widely distributed throughout the tropical and subtropical regions of Asia and Africa and traditionally employed in the management of respiratory, gastrointestinal and dermatological disorders. Grangea maderaspatana plant has also demonstrated potential anti-inflammatory, analgesic and antimicrobial activities. This study investigates the chemical composition of the petroleum ether extract of aerial part of Grangea maderaspatana using Gas Chromatography-Mass Spectrometry (GC-MS). The plant, known for its traditional medicinal uses, was subjected to Soxhlet extraction and the extract was analyzed to identify its phytochemical components. The analysis revealed a complex mixture of hydrocarbons, fatty acids, terpenes and other organic compounds with tetracontane (45.20% area at different retention time), n-hexadecanoic acid (7.05%area), (S,Z)-heptadeca-1,9-dien-4,6-diyn-3-ol (6.18% area at different R. Time) and neophytadiene (5.08%area) being the major components. The presence of these compounds suggests potential applications in pharmaceuticals, cosmetics and other industries due to their bioactive properties.

Keywords: Grangea maderaspatana, Phytochemicals, GC-MS, Soxhlet extraction, Methanol extract

INTRODUCTION: Grangea maderaspatana, commonly known as Madras carpet or Indian chickweed, is a prostrate annual herb belonging to the Asteraceae family. This plant is widely distributed across tropical and subtropical regions of Asia and Africa, particularly in India, Sri Lanka, and parts of Southeast Asia. G. maderaspatana has garnered significant scientific interest due to its traditional medicinal uses and potential pharmacological properties. Morphologically, G. maderaspatana is characterized by its spreading habit, with stems reaching up to 30-45 cm in length. The leaves are simple, alternate, and deeply lobed, giving the plant a distinctive appearance.

The inflorescence consists of small, yellow flower heads that are solitary or clustered at the ends of branches ¹. Ethnopharmacological studies have reported various traditional uses of G. maderaspatana in folk medicine. It has been employed in the treatment of various ailments, including respiratory disorders, gastrointestinal issues, and skin diseases. The plant is also known for its potential anti-inflammatory, analgesic, and antimicrobial properties ².

Phytochemical investigations have revealed the presence of diverse bioactive compounds in G. maderaspatana, including flavonoids, terpenoids, and phenolic compounds. These secondary metabolites are believed to be responsible for the plant's medicinal properties and have been the subject of numerous scientific studies aiming to elucidate their structures and biological activities ³. Recent pharmacological studies have focused on evaluating the therapeutic potential of G. maderaspatana extracts and isolated compounds. Research has shown promising results in areas such as hepatoprotection, antioxidant activity, and anti-diabetic effects, suggesting that this plant may have significant potential in modern medicine and drug discovery ⁴.

MATERIALS AND METHODS:

Plant Material: The air-dried aerial parts 1.5 kg, purchased from local vendor of Jaipur Rajasthan India.

Extraction: Using a grinder, the air-dried plant material was first reduced to a fine powder. Then, 300 ml of petroleum ether solvent were used to perform a Soxhlet extraction technique on 100 gm of the powdered material for 12 hours X 3 days. A rotary vacuum evaporator (make: N.N. Series from Eyela, Tokyo, Japan) was used to remove extra solvent along with a digital water bath SB-651. The extract was treated with sodium sulphate to remove any moisture that might have remained. A concentrated sample of the extract was obtained after it was filtered to remove any grainy material using Whatman No. 1 filter paper.

The final extract was kept in an airtight container at low temperature.

GC-MS Analysis: Gas Chromatography combined with Mass Spectrometry is a preferred methodology for routine analysis of compounds. The GC-MS analysis of the above-mentioned extracts was performed with a Gas Chromatography unit Shimadzu GCMS-QP2010 Plus comprising AOC-20i+s auto sampler at Manipal University Jaipur Rajasthan India. Various components were identified by different retention times, which were detected by a mass spectrophotometer. The chromatogram plot of intensity against retention time was recorded by the software attached to it. From the graph, the compounds are identified, comparing the data with the existing software libraries like WILEY8.lib, NIST11.lib, NIST11s.lib, FFNSC2.lib and mass spectra of standard. The name, molecular weight, and structure of the components of the test materials were ascertained.

FIG. 1: GC-MS SPECTRUM OF PETROLEUM ETHER AERIAL PART EXTRACT OF G. MADERASPATANA

RESULTS AND DISCUSSION: The most abundant compound detected in the extract of G. maderaspatana is tetracontane with 45.20% area at different retention time. It is a long-chain alkane having 40 carbon atoms in the chemical structure. Similarly n-hexadecanoic acid (palmitic acid) with 7.05% area also found in the extract which is a common saturated fatty acid found in plants and animals. Other significant components include (S,Z)-heptadeca-1,9-dien-4,6-diyn-3-ol (6.18% area at different R. Time), an unusual unsaturated alcohol and neophytadiene (5.08% area), a diterpene found in the petroleum ether aerial part extract of G. maderaspatana. Generally, neophytadiene found in tobacco plants. In this extract, phytol (2.66%), various fatty acids such as 9, 12, 15-octadecatrienoic acid (3.84%), and squalene (2.43%) sterols like chondrillasterol (1.87%) and alpha-amyrin (0.86%) are also detected. The mixture contains a range of hydrocarbons, fatty acids, terpenes and other organic compounds, indicating a complex natural product.

Tetracontane has found diverse applications across different industries due to its inimitable properties. In the field of materials science, tetracontane has been investigated as a phase change material for thermal energy storage applications. It’s high latent heat of fusion and suitable melting temperature range, make it a potential molecule for use in building materials to improve energy efficiency ⁵. In the pharmaceutical industry, tetracontane has been studied as a potential excipient in drug formulations, particularly for controlled release applications. It’s hydrophobic nature can be utilized to modulate drug release profiles in certain dosage forms ⁶. In the cosmetics industry, tetracontane is used in formulations for their emollient properties and ability to form protective barriers on the skin ⁷.

Additionally, tetracontane used as a reference compound in gas chromatography to calibrate retention times and identify unknown compounds in complex mixtures ⁸. It’s presence in natural waxes also makes it relevant in the study of plant physiology and ecology, particularly in understanding plant adaptations to water stress and environmental conditions ⁹. n-Hexadecanoic acid, also known as palmitic acid, is a saturated fatty acid with diverse applications across multiple industries. In the pharmaceutical sector, it serves as an excipient in drug formulations, enhancing drug solubility and absorption ¹⁰. The cosmetics industry widely uses n-hexadecanoic acid in skincare products for its emollient properties and ability to form a protective barrier on the skin ¹¹. In food science, it is a common ingredient in food additives and used as a flavoring agent ¹². n-Hexadecanoic acid is utilized in the production of soaps, lubricants and plasticizers ¹³ and it plays a important role in cellular metabolism and serves as a precursor for longer fatty acids ¹⁴. Recent research has also explored it’s therapeutic potential as an antimicrobial and anti-inflammatory agent ¹⁵.

(S,Z)-Heptadeca-1, 9-dien-4, 6-diyn-3-ol is a unsaturated alcohol belongs to the class of polyacetylenic compounds, which is often found in plants of the Asteraceae family and have attracted interest due to their potential biological activities. Studies on related polyacetylenic alcohols compounds have demonstrated anti-inflammatory, antimicrobial and cytotoxic activities, suggesting potential applications in drug discovery and development ¹⁶. In natural product chemistry, the presence of such compounds can serve as chemotaxonomic markers, aiding in the classification and identification of plant species ^{17, 18}. Neophytadiene is a diterpene hydrocarbon, often used as a biomarker for certain plant species, particularly in tobacco and some marine algae ¹⁹. Studies have shown that neophytadiene exhibits antimicrobial properties, demonstrating effectiveness against certain bacterial and fungal strains ²⁰. Neophytadiene investigated for its potential anti-inflammatory and analgesic effects suggesting possible applications in pain relief management and inflammatory conditions ²¹.

It’s antioxidant properties, indicating potential use in preventing oxidative stress-related diseases ²². In the fragrance industry, neophytadiene has been taken into consideration for perfumery applications and adds to the aroma profile of certain essential oils ²³.

TABLE 1: PHYTOCHEMICALS IDENTIFIED IN THE PETROLEUM ETHER EXTRACT OF THE AERIAL PART OF GRANGEA MADERASPATANA BY GC-MS

TABLE 2: MAJOR PHYTOCHEMICALS IDENTIFIED IN PETROLEUM-ETHER EXTRACT OF GRANGEA MADERASPATANA AERIAL PART

Characterization Data: Compound I as Tetracontane: Colorless amorphous powder, ¹H NMR (δppm, CDCl₃, 300 MHz) δ: 2.26 (2H, m, CH₂), 2.04 (2H, m, CH₂), 1.54 (4H, m, 2 X CH₂), 1.25 (68H, brs, 34 X CH₂), 0.87 (3H, t, J = 6.8 Hz, CH₃), 0.84 (3H, t, J = 6.3 Hz, CH₃). ¹³C NMR (δppm, CDCl₃, 75 MHz) δ: 31.90 (CH₂), 29.67 (31 X CH₂), 29.63 (CH₂), 28.59 (CH₂), 27.36 (CH₂), 26.15 (CH₂), 25.89 (CH₂), 22.67 (CH₂), 14.09 (-CH₃).

Compound II as n-Hexadecanoicacid: Obtained white waxy compound. ¹H NMR (δppm, CDCl₃, 300 MHz) δ: 0.854 (3H, t, -CH₃), 1.260 (24H, m, 12 X –CH₂), 1.571 (2H, m, -CH₂-CH₂-COOH), 2.169 (2H, t, -CH₂-CH₂-COOH), 5.363 (1H, s, -CH₂-CH₂-COOH). ¹³C NMR (δppm, CDCl₃, 75 MHz) δ: 177.13 (-COOH), 14.02 (-CH₃), 22.94 (CH₃-CH₂-), 34.35 (-CH₂-CH₂-COOH), 24.81 (-CH₂-CH₂-COOH), 28.96 (remaining –CH₂).

Compound III as (S,Z)-Heptadeca-1,9-dien-4,6-diyn-3-ol: Light brown powder,¹H NMR (δppm, CDCl₃, 300 MHz): δ 0.96 (3H, t, -CH₃), 1.33 (2H, m, -CH₂-CH₃), 5.48 (2H, m, -CH=CH-), 2.70 (2H, d, -CH₂), 5.89 (1H, t, CH₂-CH-), 5.23 (2H, d, CH₂-CH-), 1.29 (6H, m, -CH₂-), 1.42 (2H, m, -CH₂-), 2.01 (2H, m, -CH₂-). ¹³C NMR (δppm, CDCl₃, 75 MHz): δ 115.10 (C-1), 65.15 (C-2), 75.80 (C-3), 70.65 (C-4), 64.40 (C-5), 73.25 (C-6), 19.60 (C-7), 123.80 (C-8), 133.10 (C-9), 32.47 (C-10), 30.76 (C-11), 30.98(C-12), 30.13 (C-13), 32.54 (C-14), 23.54 (C-15), 14.90 (C-16).

Compound IV as Neophytadiene: Grayish white oil, ¹H NMR (δppm, CDCl₃, 300 MHz): δ 1.01 (6H, d, 2 X -CH3), 1.06 (6H, d, 2 X -CH3), 1.83 (1H, m, -CH-), 1.65 (2H, m, -CH-), 1.25-1.29 (16H, m, -CH2-), 5.16 (2H, d, CH2-CH-), 6.25 (1H, t, CH2-CH-), 4.80 (1H, s, -CH_a-). 4.80 (1H, s, -CH_b-). ¹³C NMR (δppm, CDCl₃, 75 MHz): δ 116.3 (C-1), 136.9 (C-2), 154.2 (C-3), 38.2 (C-4), 25.4 (C-5), 37.7 (C-6), 32.1 (C-7), 37.2 (C-8), 25.3 (C-9), 37.9 (C-10), 32.0 (C-11), 25.0 (C-12), 39.7 (C-13), 28.5 (C-14), 22.3 (-CH₃).

CONCLUSION: Phytochemical analysis of Grangea maderaspatana has identified various bioactive compounds, including fatty acids, terpenes, phytols and other organic compounds, which contribute to its medicinal potential. In the petroleum ether extract of aerial part of the plant found tetracontane (45.20% area at different retention time), n-hexadecanoic acid (7.05%area), (S,Z)-heptadeca-1,9-dien-4,6-diyn-3-ol (6.18% area at different R. Time) and neophytadiene (5.08% area) as major compounds on GC-MS analysis. The presence of these compounds suggests potential applications in pharmaceuticals, cosmetics and other industries due to their bioactive properties.

ACKNOWLEDGEMENT: Authors wish to thanks Head, Department of Chemistry University of Rajasthan Jaipur Rajasthan India for providing Laboratory facilities.

CONFLICT OF INTREST: Authors declare no conflict of interest.

REFERENCES:

1. Shrivastava DK and Chandra TP: Phytochemical analysis and Evaluation of antimicrobial efficacy of different solvent fractions of Grangea maderaspatana (L.) Poir and Solanum virginianum Cuestiones de Fisioterapia 2025; 54(2): 3320-3329.
2. Kumar VS, Ahmed N, Alphonso JK, Chandrasekar S and Boopathy U: A review on pharmacological activities of Mukia maderaspatana. International Journal of Health Sciences (III) 2022; 4449-4459.
3. Danhabal SP, H Roger, NC, Eloi P, Adama H, K Remy B, Constantin MD and Abdoulaye Y: Phytochemical screening, total phenolics content and antioxydants potential of different parts of Grangea maderaspatana from Burkina Faso. International Research Journal of Pure and Applied Chemistry 2021; 22(10): 36-44.
4. Yougoubo A, Dabire MC, Bationo KR, Ganame A, Noba A, Koala M and Nacro M: Antioxidants activities, HPTLC and HPLC/MS characterization of some phenolic acids of Grangea maderaspatana roots extracts from Burkina Faso. International Journal of Biological and Chemical Sciences 2024; 18(3): 1152-1165.
5. Sharma A, Tyagi VV, Chen CR and Buddhi D: Review on thermal energy storage with phase change materials and applications. Renewable and Sustainable Energy Reviews 2009; 13(2): 318-345.
6. Goyanes A, Wang J, Buanz A, Martínez-Pacheco R, Telford R, Gaisford S and Basit AW: 3D printing of medicines: Engineering novel oral devices with unique design and drug release characteristics. Molecular Pharmaceutics 2015; 12(11): 4077-4084.
7. Petry T, Bury D, Fautz R, Hauser M, Huber B, Markowetz A, Mishra A, Rettinger K, Schuh W and Teichert T: Review of data on the dermal penetration of mineral oils and waxes used in cosmetic applications. Toxicology Letters 2017; 280: 70-78.
8. Tissot E, Rochat S, Debonneville C and Chaintreau A: Rapid GC-FID quantification technique without authentic samples using predicted response factors. Flavour and Fragrance Journal 2012; 27(4): 290-296.
9. Jetter R and Riederer M: Localization of the transpiration barrier in the epi-and intracuticular waxes of eight plant species: water transport resistances are associated with fatty acyl rather than alicyclic components. Plant Physiology 2016; 170(2): 921-934.
10. Krishnaveni K, Murugan M, Kalaimathi RV, Basha AN, Pallan GA, Kandeepan C and Dhakar RC: ADMET informatics of Plant Derived n-Hexadecanoic Acid (Palmitic Acid) from ethyl acetate fraction of Moringa oleifera leaf extract. Journal of Drug Delivery and Therapeutics 2022; 12(5): 132-45.
11. Kalasariya HS, Patel NB, Yadav A, Perveen K, Yadav VK, Munshi FM and Jeon BH: Characterization of fatty acids, polysaccharides, amino acids, and minerals in marine Macroalga chaetomorpha crassa and evaluation of their potentials in skin cosmetics. Molecules 2021; 26(24): 7515.
12. Mortensen A, Aguilar F, Crebelli R, Di Domenico A, Dusemund B, Jose FM, Galtier P, Gott D, Gundert-Remy U, Leblanc JC, Lindtner O, Moldeus P, Mosesso P, Parent-Massin D, Oskarsson A, Stankovic I, Waalkens-Berendsen I, Woutersen RA, Wright M, Younes M, Boon P, Chrysafidis D, Gurtler R, Tobback P, Gergelova P, Rincon AM and Lambre C: EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS), Re‐evaluation of fatty acids (E 570) as a food additive. EFSA Journal 2017; 15(5): 04785.
13. Zhu XN, Nie CC, Zhang H, Lyu XJ, Qiu J and Li L: Recovery of metals in waste printed circuit boards by flotation technology with soap collector prepared by waste oil through saponification. Waste Management 2019; 89: 21-26.
14. Carta G, Murru E, Banni S and Manca C: Palmitic acid: Physiological role, metabolism and nutritional implications. Frontiers in Physiology 2017; 8: 902.
15. Aparna V, Dileep KV, Mandal PK, Karthe P, Sadasivan C and Haridas M: Anti-inflammatory property of n-hexadecanoic acid: structural evidence and kinetic assessment. Chemical Biology & Drug Design 2012; 80(3): 434-439.
16. Xie Q and Wang C: Polyacetylenes in herbal medicine: A comprehensive review of its occurrence, pharmacology, toxicology, and pharmacokinetics (2014–2021). Phytochemistry 2022; 201: 113288.
17. Cerda-Pena C and Contreras S: Characterization and chemo-taxonomic evaluation of plant leaf waxes (long chain n-alkanoic acids, n-alkanes and n-alkanols) as a vegetation biomarker from species of the South American temperate forest (STF). Ecological Indicators 2022; 136: 108675.
18. Joao GM, Nunes J, Rodrigues M and Ferreira L: Chemotaxonomic differentiation of pinus species based on n‐alkane and long‐chain alcohol profiles of needle cuticular waxes. Chemistry & Biodiversity 2023; 20(5): 202300043.
19. Selmy AH, Hegazy MM, El-Hela AA, Saleh AM and El-Hamouly MM: In-vitro and in-silico studies of neophytadiene; a diterpene isolated from aeschynomene elaphroxylon (guill. & perr.) taub. as apoptotic inducer. Egyptian Journal of Chemistry 2023; 66(10): 149-161.
20. Susanti Y and Ayun AQ: Phytochemical, antioxidant, and antibacterial activity of essential oil Hyptis capitata using solvent-free microwave extraction. Journal of Applied Agricultural Science and Technology 2024; 8(4): 450-460.
21. Mamgain A, Kenwat R and Paliwal R: Phytochemical profiling and molecular investigation of Moringa oleifera leaves for anti-arthritic potential: assessment and identification of phytopharmaceuticals through GC-MS analysis, in-silico study, admet analysis, and in-vitro evaluation. Current Biotechnology 2024; 13(3): 140-158.
22. Gonzalez-Rivera ML, Barragan-Galvez JC, Gasca-Martinez D, Hidalgo-Figueroa S, Isiordia-Espinoza M and Alonso-Castro AJ: In-vivo neuropharmacological effects of neophytadiene. Molecules, 2023; 28(8): 3457.
23. Kliszcz A, Danel A, Pula J, Barabasz-Krasny B and Mozdzen K: Fleeting beauty-The world of plant fragrances and their application. Molecules 2021; 26(9): 2473.
    

    ---

    How to cite this article:

    Pathak J, Shekhawat PS, Rishi H and Bhargava S: Spectral analysis of petroleum ether aerial part extract of Grangea maderaspatana using gas chromatography-mass spectrometry. Int J Pharm Sci & Res 2025; 16(10): 2855-60. doi: 10.13040/IJPSR.0975-8232.16(10).2855-60.

    ---

    All © 2025 are reserved by International Journal of Pharmaceutical Sciences and Research. This Journal licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported License.