INTRODUCTION:

All over the world for millennia, medicinal plants and their extracts have been used in the prevention and treatment of almost all kinds of ailments¹. History revealed the importance of mother nature as it is considered to be an important source for most of the drugs in current use². Across the world, the use of herbal medicine and phytonutrients continues to increase as men resorting to herbal products for their treatment and other health challenges³. Therefore, the plant with unknown pharmacological activity has been investigated extensively as it is a source of new drug candidates, identification of chemical constituents presents in the investigational plant which is biologically active is also an essential part of the analysis as it leads to further pharmacological studies in different targets^4,5,6.

The primary aim of the metabolomics analysis of plants is to detect all metabolites in a plant sample simultaneously. But there is no single analytical technique to cover the broad metabolites available. While GC-MS is mainly focused on primary metabolites like fatty acids, organic acids, amino acids, and carbohydrates^{7,8,9,10,11,12}. LC-MS covers the overall richness of plant secondary metabolites which are semi-polar and polar such as saponins, alkaloids, flavonoids, phenolic acids, polyamines, glucosinolates, and its derivatives^13,14.

H. senjiana belongs to the Annonaceae family is an endemic tree to Gingee Hills, Tamil Nadu, India found in the forest fringes at 300m altitude^15,16,17. There is no scientific literature available for biological activity and ethnomedical uses of this plant. The phytoconstituents present in the other phylogenetically related species exhibited a remarkable biological activity. Consequently, there might be a correlation between chemical and biological activity with the closely related species¹⁸. Polyalthia longifolia which is phylogenetically related to H. senjiana is used conventionally for the treatment of fever and possesses antibacterial, antiulcer, anti-microbial, and hepatoprotective activities^{19,20,21,22,23}. The plant under the same family and genus exhibit the same biological activity due to the presence of similar phytoconstituents present in the species that are proved in the prior studies. In the current study preliminary analysis to identify the volatile components using GC-MS was carried out in different crude extract of H. senjiana leaves as this technique has been used widely for the analysis of non-polar and other volatile compounds present and which will serve as a reference for future studies of biological activities.

MATERIAL AND METHODS:

Solvents and reagents:

For the extraction, analytical grade solvents such as n-hexane 99 % chloroform 99 percent, ethyl acetate 99.9 percent, isopropyl alcohol 99 percent, and methanol 99.9 percent (Merck Specialties Pvt. Ltd., Mumbai, India) were utilized.

Apparatus used:

Rotary evaporator (Buchi Labor Technik, Switzerland), GCMS-QP2010 PLUS-Shimadzu Corporation Japan) was used for the study.

Collection and identification of plant material:

The matured leaves of the H. senjiana tree endemic to Gingee hills, Tamil Nadu, India was collected in September 2019. “The specimen was identified by Dr. C. Murugan, Scientist ‘E’, Head of Office, Botanical Survey of India Southern Regional Centre, T. N. A. U. Campus, Lawley Road, Coimbatore-641 003 (Reg. No. of the certificate: BSI/SRC/5/23/2019/Tech/3313), and the specimen was assigned voucher no SK1677 and was deposited for future reference in the Herbarium, IIISM, SRM IST, Tamil Nadu, India”.

Preparation of plant material:

The collected leaves were dried in darkness at room temperature for one week and size reduced in the suitable electric mill of particle size of 0.4 mm and was stocked in the airtight bottle to safeguard from moisture and light until the analysis was carried out.

Preparation of plant extracts:

The dried and coarsely powdered leaves were subjected to successive extraction by cold maceration with the solvent of increasing polarity such as hexane followed by chloroform, ethyl acetate, isopropyl alcohol, and methanol. The plant material was taken in a flat bottom bell jar and solvents were added successively and sealed with its contents. The extraction was carried out for 7 days with occasional handshaking and stirring. The homogenate obtained was filtered with a piece of white cloth and then filtered with Whatman filter paper and the filtrate was reduced to get a crude extract under decreased pressure using Rota evaporator, and stockpiled in a fridge at 4°C for future use.

The GC-MS analysis:

Using a GCMS-QP2010 PLUS-Shimadzu corporation Japan) equipped with an HP-5 MS column (30m in length, 250mm in diameter, and 0.25mm in thickness), the bioactive chemicals from the various extracts of H. senjiana leaves were analyzed using GC-MS. The injection temperature was kept at 280°C while the column oven temperature was kept at 50°C. A high energy electron ionization system was used in the GC-spectroscopic MS's analysis (70 eV). Helium (99.99 percent) was employed as the carrier gas, flowing at a rate of 0.95ml/min. With a rise rate of 3°C/min and a hold on time of roughly 10 minutes, the oven temperature programme was set to 50-300°C. At last, the temperature was raised to 300°C at a rate of 10°C per minute. Injecting 1 L of 1 percent extracts diluted with mobile phase at a split ratio of 5.0 and a solvent cut time of 3.00 minutes into the injector in split mode. The overall run duration was 39 minutes, and 3 scans of the mass value in the range of 50 to 1000m/z were performed. Based on the peak area created in the chromatogram, the relative quantity of the chemical components present in each of the H. senjiana extracts was expressed as a percentage.

Identification of chemical constituents:

Bioactive compounds present in different extracts of the leaves of H. senjiana were recognized based on the retention time of different compounds on the column and the mass spectra of different extracts were compared with the known spectra which are stored in the database of NIST 8 (National Institute of Standards and Technology) and WILEY 9 with more than 62000 data of standards of GC-MS systems.

RESULTS:

Bioactive compounds:

The bioactive compounds present in n-hexane, chloroform, ethyl acetate, isopropyl alcohol, and methanol extracts obtained from the leaves of H. senjiana were identified and the number of compounds present with their name, corresponding retention time, and % area was given in Table 1-5. The bioactive compounds separated based on their retention and elution order in the column were identified and characterized with the help of a mass spectrometer by comparing the mass spectra obtained with the standard mass spectra stored in the inbuilt database of the NIST 8 library to identify the compound present.

Hexane extract:

Based on the % area, the top three major compounds present in the n-hexane were identified as Delta -Tocotrienol (19.17%), Squalene (7.46%) and Geranyl acetate (5.81%) and the other compounds present were given in Table 1.

Table 1: GC-MS spectral analysis of hexane extract of H. senjiana

Name of the compounds	Retention time (min)	Area	Area%
Cyclohexene, 1-Methyl-4-(1-Methyl)	8.253	16686221	4.06
1-Benzofuran-2(3h)-One	12.735	4731359	1.15
Caryophyllene Oxide	19.166	7676974	1.87
Neophytadiene	22.826	7574890	1.84
2-Pentadecanone, 6,10,14-trimethyl-	22.934	5755670	1.40
Farnesyl Acetone C	23.980	11563524	2.81
Pentadecanoic Acid, 14-Methyl-, M	24.111	17809625	4.33
9,12-Octadecadienoic Acid, Methyl	26.406	14317752	3.48
9-Octadecenoic Acid (Z)-, Methyl E	26.487	23239118	5.65
2-Hexadecen-1-Ol, 3,7,11,15-Tetrame	26.649	23772946	5.78
Hexadeca-2,6,10,14-tetraen-1-ol, 3,7,11,16-tet	29.867	5034211	1.22
trans-Geranylgeraniol	34.437	6269570	1.52
14-Beta-H-pregnane	34.884	7111704	1.73
Delta-Tocotrienol	37.633	78889948	19.17
3,5-Dimethyl Cyclopentenone	37.769	4444730	1.08
Squalene	38.108	30687120	7.46
Vitamin E	38.522	6473923	1.57
Geranylgeranyl acetate	38.698	23909122	5.81

Chloroform extract:

The chloroform crude extract was found to contain Delta-Tocotrienol (18.98%) followed by 5,8,11-Eicosatrienoic acid methyl ester (8.83%) and Neophytadiene (4.58%) as the major compounds present as presented in Table 2.

Table 2: GC-MS spectral analysis of chloroform extract of H. senjiana

Name of the compounds	Retention time (min)	Area	Area%
Cyclohexene, 1-Methyl-4-(1-Methy	8.262	18152440	4.45
Caryophyllene oxide	19.177	6444411	1.58
Dodecyl acrylate	20.672	5104652	1.25
Aspidospermidine-3-Carboxylic Acid	22.429	5356390	1.31
Neophytadiene	22.843	18678557	4.58
6-Octen-1-Ol, 3,7-Dimethyl-, Acetate	23.187	5834037	1.43
3,7,11,15-Tetramethyl-2-hexadecen-1-ol	23.473	6886284	1.69
Squalene	24.004	10601229	2.60
Pentadecanoic acid, 14-methyl-, methyl ester	24.122	10022342	2.46
1,4-Dimethyladamantane	24.661	9088485	2.23
Hexadecenoic Acid, Ethyl Ester	25.051	7148332	1.75
9,12-Octadecadienoic Acid, Methyl	26.416	5273428	1.29
9-Octadecenoic Acid (Z)-, Methyl Ester	26.496	9442177	2.32
2-Hexadecen-1-Ol, 3,7,11,15-Tetramet	26.660	12376259	3.04
7-Tetradecenal, (Z)-	27.338	5170880	1.27
5,8,11-Eicosatriynoic acid, methyl ester	30.859	35990570	8.83
Delta-Tocotrienol	37.648	77390086	18.98
trans-Geranylgeraniol	38.712	15032473	3.69

Ethyl acetate extract

The ethyl acetate crude extract possesses Delta-Tocotrienol (12.50%), 5,8,11-Eicosatrienoic acid methyl ester (9.61%), and Neophytadiene (7.68%) as the major compounds with other compounds given in Table 3.

Table 3: GC-MS spectral analysis of ethyl acetate extract of H. senjiana

Name of the compounds	Retention time (min)	Area	Area%
2,4-Ditert-Butylphenol	17.798	2435806	1.12
Caryophyllene oxide	19.167	2831144	1.31
2,3-dihydroxycyclohexanone	20.472	4143049	1.91
Aspidospermidin-17-Ol, 1-Acetyl-16-	22.413	2683308	1.24
Neophytadiene	22.834	16635992	7.68
2-Pentadecanone, 6,10,14-trimethyl-	22.937	2221707	1.03
3,7,11,15-Tetramethyl-2-hexadecen-1-ol	23.184	4091955	1.89
Pentadecanoic acid, 14-methyl-, methyl ester	24.113	6282905	2.90
Dibutyl phthalate	24.648	3703855	1.71
9,12-Octadecadienoic acid, methyl ester, (E, E)-	26.406	4216084	1.95
9-Octadecenoic Acid (Z)-, Methyl Ester	26.486	6844817	3.16
2-Hexadecen-1-Ol, 3,7,11,15-Tetramethyl	26.646	8803170	4.06
7-Tetradecenal, (Z)-	27.329	4181016	1.93
Octadecanoic Acid, Ethyl Ester	27.641	2300231	1.06
5,8,11-Eicosatriynoic acid, methyl ester	30.835	20820320	9.61
Delta-Tocotrienol	37.591	27065531	12.50
6,10-Dodecadien-1-yn-3-ol, 3,7,11-trimethyl-	38.103	3910802	1.81
trans-Geranylgeraniol	38.183	2228176	1.03
Vitamin E	38.514	4312727	1.99
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2	38.683	9883319	4.56

Isopropyl alcohol extract:

The isopropyl alcohol crude extract contains 6,10,14-Trimethyl-2-pentadecanone (19.44%), 4,8,12,16-Tetramethylheptadecan-4-olide (5.98%), Hexadecenoic acid methyl ester (5.52%) the extract with other compounds presents with different ratio presented in Table 4.

Table 4: GC-MS spectral analysis of IPA extract of H. senjiana

Name of the compounds	Retention time (min)	Area	Area%
1,3-Dioxan-5-ol	3.965	3401599	2.91
Benzenesulfonic Acid, 4-Hydroxy-	7.770	4603070	3.94
N-Methyl adrenaline, 3TMS derivative	9.447	2071177	1.77
Nonanal	9.808	2930479	2.51
1H-Pyrrole-2,5-dione, 3-ethyl-4-methyl-	12.769	3707378	3.17
4-Cyclopentene-2,2-D2-1,3-Diol,	13.104	2829224	2.42
Terebic acid	18.420	5748204	4.91
2-Pentadecanone, 6,10,14-Trimethy	22.941	22744622	19.44
2-Pentadecanone, 6,10,14-trimethyl-	23.964	1391582	1.19
Hexadecenoic Acid, Methyl Ester	24.107	6454045	5.52
1,2-Benzenedicarboxylic Acid,	24.645	1866740	1.60
Ethyl Nona decanoate	25.035	1259726	1.08
2,6-Dimethyloctan-2-Ol	25.666	2760917	2.36
9,12-Octadecadienoic Acid, Methyl E	26.401	3063258	2.62
9-Octadecenoic Acid (Z)-, Methyl Es	26.481	4809794	4.11
Methacrylic acid, heptadecylic ester	26.872	2285723	1.95
2-Methyltetracosane	27.296	1332270	1.14
2-Tetradecyloxirane	27.842	1203897	1.03
2-Dodecanol, 2-methyl-	28.236	2598201	2.22
4,8,12,16-Tetramethylheptadecan-4-olide	29.637	6993944	5.98
Cyclopentane, (4-Octyldodecyl)-	30.253	2492112	2.13
2-Dodecanol, 2-methyl-	30.599	2085161	1.78
5,8,11-Eicosatriynoic acid, methyl ester	30.822	1824980	1.56
14-Beta-H-Pregna	35.109	1329163	1.14

Methanol extract:

Methanol crude extract had benzenesulfonic acid, 4-hydroxy (20.49%), 2,3-dihydroxycyclohexanone (13.00%), 9-Octadecenoic acid (Z)- methyl ester (8.78%) as the uppermost three main compounds presents along with other compounds present in different ratio as depicted in Table 5.

Table 5: GC-MS spectral analysis of methanol extract of H. senjiana

Name of the compounds	Retention time (min)	Area	Area%
Benzenesulfonic Acid, 4-Hydroxy	7.725	15089797	20.49
Phenol, 2,6-Dimethoxy-	14.951	2203785	2.99
D-Allose	16.001	1112463	1.51
Pentane dioic acid, 2-methyl-, dimethyl ester	18.420	1513390	2.05
2h-Pyran-2-On, 5,6-Dihydro-4-(2,3-Dimethyl)	18.771	2865539	3.89
Methyl 5,7-hexadecadiynoate	20.312	2307046	3.13
2,3-dihydroxycyclohexanone	20.501	9577246	13.00
Aspidospermidin-17-Ol, 1-Acetyl-16	22.412	1789142	2.43
E-2-Tetradecen-1-ol	22.821	6037046	8.20
Pentadecanoic acid, 14-methyl-, methyl ester	24.108	5237398	7.11
Dibutyl phthalate	24.641	2696260	3.66
1-Octadecanethiol	25.036	899957	1.22
9,12-Octadecadienoic acid, methyl ester, (E, E)-	26.401	3665570	4.98
9-Octadecenoic acid (Z)-, methyl ester	26.481	6465410	8.78
2-Hexadecen-1-Ol, 3,7,11,15-Tetramethyl	26.639	2009808	2.73
Octadecanoic Acid, Methyl Ester	26.803	1169490	1.59
Hexadecenoic acid, 2-hydroxy-1- (hydroxymethyl	31.505	1399647	1.90
Carbonic acid, Eicosyl prop-1-en-2-yl ester	34.288	893701	1.21

The GC chromatogram of the five extracts were presented in Figures 1-5 shows the total number of compounds present and their retention time and elution order in the column.

Fig. 1: GC chromatogram of H. senjiana hexane extract

Fig. 2: GC chromatogram of H. senjiana chloroform extract

Fig. 3: GC chromatogram of H. senjiana ethyl acetate extract

Fig. 4: GC chromatogram of H. senjiana IPA extract

Fig. 5: GC chromatogram of H. senjiana methanol extract

DISCUSSION:

The leaves of H. senjiana were extracted repeatedly using solvents with increasing polarity, such as n-hexane, chloroform, ethyl acetate, isopropyl alcohol, and methanol, to obtain the crude extracts. Delta-tocotrienol was found to have a protective effect against oxidative destruction in MC3T3-E1 cells and the effect is due to a decrease in intercellular reactive oxygen species (ROS). The various extracts thus acquired were subjected to GC-MS study, and the analysis revealed the existence of numerous phytoconstituents. Based on that, some of the compounds are found to have proven biological activity^24,25. Aside from that, cyclohexene, 1-methyl-4-(1-methyl) and squalene show up in extracts of hexane and chloroform^26,27 where squalene is discovered to have antioxidant and anti-cancer properties in addition to chemo-preventive activity against colon carcinogenesis²⁸. Neophytadiene, which has anti-inflammatory, antioxidant, and cardioprotective characteristics, and caryophyllene oxide, which has antifungal action. Additionally, trans-geranyl geraniol, which has been shown to have antinociceptive activity²⁹ by reducing the toxicities of the statin drug class without reducing the effectiveness of these drugs in lowering cholesterol, also has antiplatelet activity³⁰ and is present in varying concentrations in crude extracts of hexane, chloroform, and ethyl acetate.

Vitamin E has been shown to be effective in treating conditions like atopic dermatitis, psoriasis, skin cancer, and wound healing. Hexane and ethyl acetate extracts were discovered to contain various amounts of ^31,32 the presence of 2-pentadecanone, 6,10,14-trimethyl in hexane and ethyl acetate extracts as well as geranyl acetate in both of those extracts was reported to have antimycobacterial activity³³. Pentadecanoic acid, 14-methyl-methyl ester, and phytol were found to have antioxidant and antinociceptive effects³⁴and were also found to be cytotoxic against breast cancer cell lines. Phytol is the precursor for the synthesis of Vitamin E and Vitamin K. These compounds were present in hexane, chloroform, ethyl acetate and methanol extracts in different percentage concentrations³⁵. All five extracts include varying amounts of 9,12-octadecadienoic acid, methyl ester (E, E), and 9-octadecenoic acid, methyl ester (Z). Different ratios of 5,8,11-eicosatrienoic acid, methyl ester was found in extracts of chloroform, ethyl acetate, and isopropyl alcohol. Various amounts of 2,3-dihydroxycyclohexanone, dibutyl phthalate, and aspidospermidin-17-ol, 1-acetyl-16 were found in the ethyl acetate and methanol extracts. 7-Tetradecenal, (Z)- Found in extracts of chloroform and ethyl acetate. 4-hydroxybenzenesulfonic acid, which can be found in extracts of isopropyl alcohol and methanol. Both n-hexane and ethyl acetate extracts include 9,12,15-octadecatrienoic acid, methyl ester (ZZZ). However, no consistent group of significant components was revealed in the crude extracts. According to the investigations, the majority of the constituents identified by GC-MS analysis are molecules with biological activity. Major bioactive components found in all of the examined extracts were revealed by the investigation. They were known to have pharmacological properties that might affect the plant's potential for therapeutic use. The therapeutic use of the plant is supported by the chemicals in H. senjiana leaf extract that have been shown to have these biological actions. The discovery of these substances in the plant serves as a starting point for further biological and pharmacological research by providing evidence of the plant's potential health benefits.

CONCLUSION:

The GC-MS analysis helps to identify the source of many chemical constituents from the peak pattern of chromatograms. The fingerprint technique can identify adulterations and other false herbal products thus the technique helps evaluate the quality of the herbal products. Therefore, GC-MS analysis is a direct and fast analytical method for the identification of steroids and other volatile compounds. The importance of the study is due to the biological activity of some of these compounds present that might support the pharmacological activity of the plants. The present study is considered to be the preliminary study that reveals the presence of volatile components in H. senjiana. Further studies on the biological activity of each fraction and isolated compounds need to be carried out.

ACKNOWLEDGEMENT:

The authors are grateful to the Management, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur for providing facilities to carry out this work.

CONFLICT OF INTEREST:

The authors declare no conflict of interest.

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Received on 15.07.2020 Modified on 29.12.2021

Research J. Pharm. and Tech 2023; 16(4):1581-1586.

DOI: 10.52711/0974-360X.2023.00258