Document Type : Original Article
Authors
Department of Pharmacognosy, College of Pharmacy, University of Ahl Al Bayt ,Kerbala, Iraq
Abstract
Phytochemicals are considered as one of the most important pharmaceutical compounds used in pharmacy at all, due to their high therapeutic efficacy and few side effects compared with chemically prepared drugs. On the other hand, the modern techniques of analysis such as GC-MS made it easier to know the chemicals that make up the materials to be studied. In our study, alcoholic extracts of (Punica granatum peel, Ziziphusspina-christi leaves, and Eucalyptus camaldulensis leaves) were prepared, in addition to prepare the mixtures of these extracts by mixing the equal proportions of two extracts only of three plant extracts each time. The result was 3 pure extracts and 3 mixture extracts. After that, these samples were analyzed with the GC-MS device, and the results of the analysis were compared with each other to find out the structural differences occurred after mixing. The results proved the presence of new chemical compounds in the mixture extracts completely different from the chemical compounds found in the pure compounds, whether in terms of chemical composition or biological activity.
Graphical Abstract
Keywords
- GC
- MS Alcoholic extracts Punica granatum Ziziphusspina
- christi Eucalyptus camaldolehsis Medicinal plants
Main Subjects
Introduction
Pure compounds from natural sources or pure plant extracts can be considered as sources for newer drugs [1]. World Health Organization (WHO) considered that about 80% of humans rely on folk medicine for their primary healthcare care. The use of medicines from herbal sources in Asia gives a long history of contact between human and the environment. In traditional medicine, there are phytochemicals used to treat chronic diseases and infections [2]. Because of the side effects and bacterial resistance in synthesized drugs, human turned to use botany. There are thousands of chemical compounds from plants sources that are safe and effective alternatives with fewer side effects [3].
Punica granatum; a granular apple [4]. Pomegranate from the family punicaceae are fruits to the Mediterranean region. The edible part of the fruit contains many phytochemicalsas saccharides, polyphenol, and some minerals. The major class of pomegranate chemicals is the polyphenols such as phenolic rings with many hydroxyl groups. Pomegranate polyphenols comprise flavonoids such as flavanols, flavonols and anthocyanins, also condensed tannins and hydrolysable tannins [5].
Eucalyptus camaldulensis is an important plant belonging to the family, Myrtaceae, is used as a medicine for treatment of sore throat and some other bacterial infection of the respiratory and urinary tracts. The essential oils in the leaves are used as an expectorant to treat lung disease [6]. The alcoholic extract and the aqueous extract of Eucalyptus camaldulensis were found to be effective in inhibiting different types of Gram-positive and Gram-negative bacteria [7].
Ziziphusspina-christi has important fruits that usually eaten freshly. The fruits can be applied on wounds and ulcers [8, 9]. Pneumonia, dysentery, scorpion bites, cough, constipation, intestinal worms, and fever are some of the uses of this plant [9, 10]. It has shown that extracts of leaves of this plant has anti-microbial, anti-nociceptive, and anti-diabetic effects [11]. The extract of Ziziphusspina-christi also contains beutic acid and ceanothic acid, cyclopeptides also contain saponin glycosides, protein, free sugar and mucilage that have the anti-bacterial activity [8 10].
Gas chromatography-mass spectrometry (GC-MS) is considered as a method that performed coupling between the features of gas-chromatography and mass spectrometry to identify different compounds in the sample. GC can separate essential and semi-essential compounds with a great resolution, but it cannot diagnose them. MS can give the whole structural information about most chemicals that can be precisely identified, but it cannot readily isolate them [12].
The study aims to identify the chemical compounds resulting from mixing the following plant extracts (Punica granatum peels and Ziziphusspina-christi), (Punica granatum peels and Eucalyptus camaldulensis leaves) and (Ziziphusspina-christi and Eucalyptus camaldulensis leaves) and compare them with the chemical compounds of these extracts, while they are in their pure state, by using the GC-MS technique, and studying the biological activity of these compounds in theory, to make room for many other studies carried out by mixing plant extracts, identifying the resulting compounds, and studying the chemical reactions that occur as a result of the mixing process that led to the production of contrasting compounds, and also an applied study of the effectiveness of these compounds.
Materials and Methods
Collection of the plant material
Punica granatum peel, Ziziphusspina-christi, and Eucalyptus camaldulensis leaves were collected fresh and free from any abnormal condition or disease. They were collected from local farms in the Holy Karbala/Iraq. The raw materials were washed well with tap water, and then with distilled water more than once. After that, they were dried in the open air for a period ranging between 8-10 days. Next, it is ground by using an electric grinder for a period ranging from 4-6 minutes, and then it was stored in closed bottles until use.
Preparation of alcoholic extracts
Eucalyptus camaldolehsis leaves and Ziziphusspina-christi leaves.
20 g of the sample were weighted and put in the Soxhlet with 400 mL ethanol (70% for Eucalyptus and 95% for Ziziphusspina-christi concentration) for one day [13] (Table 1).
Table 1: Chemical compounds in Ziziphusspina-christi leaves, Punica granatum peel, Eucalyptus camaldolehsis leaves
No. |
Ziziphusspina-christi leaves |
Punica granatum peel |
Eucalyptus camaldolehsis leaves |
1 |
1-Butanol , 3-methyl- , acetate |
1-Butanol , 3-methyl- , acetate |
1-Butanol , 3-methyl- , acetate |
2 |
1,3-Bis(hydroxymethyl)urea |
dl-Alanyl-dl-valine |
Acetic acid, [(aminocarbonyl)amino]oxo- |
3 |
Propane, 1-(1-methylethoxy)- |
Xanthine, 1,3-dipropyl-8-[(4-carboxymethoxy)phenyl]- |
Ethanamine, 2,2'-oxybis- |
4 |
Butane, 1,1-diethoxy-3-methyl- |
Acetonitrile,2-[(1-ethyl-1H-1,2,3,4-tetrazol-5-yl) thio]- |
Benzene, (2-methoxyethyl)- |
5 |
Ethane, 1,1,1-triethoxy- |
(3- Methyl-oxiran-2-yl)-methanol |
Propanedioic acid, dihydroxy- |
6 |
Acetic acid, [(benzoylamino)oxy]- |
2-Formylhistamine |
Propane, 1-(1-methylethoxy)- |
7 |
Hexanoicacid, ethyl ester |
3,3-Dimethyl-4-methylamino-butan-2-one |
Butane, 1,1-diethoxy-3-methyl |
8 |
1,7,7-Trimethyl-2-vinylbicyclo[2.2.1]hept-2-ene |
Dimethylamine |
Ethane, 1,1,1-triethoxy- |
9 |
Diethyl Phthalate |
Ethanol, 2-(vinyloxy)- |
Eucalyptol |
10 |
1-Butanol, 4-mercapto- |
2-(4,5-Dihydro- 3-methyl-5-oxo-1-phenyl-4-pyrazolyl)- 5-nitrobenzoic acid |
-)-Spathulenol) |
11 |
13-Octadecenal |
(S)-(+)-1-Cyclohexylethylamine |
Diethyl Phthalate |
12 |
N-[3-[N-Aziridyl]propyl]cyclohexylamine |
Formic acid, 1-methylpropyl ester |
1, 2, 4- Triazino[5,6-E] [1,2,4]-triazine-3,6 -dione,hexahydro- |
13 |
6-Hydroxy-9-oxa-bicyclo[3.3.1]nonan-3-one |
Butane, 1,1-diethoxy-3-methyl- |
Hydroxycyprazine |
14 |
1,2 -Benzenedicarboxylic acid, ditridecyl ester |
Acetic acid, [(aminocarbonyl)amino]oxo- |
Di(pent-4-enyl)amine |
15 |
2-Propyl-5-oxohexanoic acid |
Ethyl 2,2 -diethoxypropionate |
Fumaric acid, hexadecylpropargyl ester |
16 |
2- Bromopropionic acid, hexadecyl ester |
Hexanoicacid, ethyl ester |
n-Hexadecanoic acid |
17 |
cis-3 -Methyl- exo-tricyclo [5.2.1.0 (2.6)]decane |
1,7,7-Trimethyl -2-vinylbicyclo [2.2.1] hept-2 -ene |
Z-(13,14-Epoxy)tetradec-11-en-1-ol acetate |
18 |
Hexadecane, 1,1-bis(dodecyloxy)- |
Benzoic acid, 4-(1-azepinyl)azo-, ethyl ester |
Cyclopentane-trans-1,3-dicarboxamide |
19 |
9- Oxa- bicyclo[3.3.1] nonane -2,6-dione |
Phthalic acid, allyl ethyl ester |
Trieicosane, 1-bromo-11-docosenyliden- |
20 |
3- Methyl-2- (3-methylpentyl) -3-buten- 1-ol |
2,3-Dihydroindole-4-ol-2-one |
1,4-Naphthalenediol, decahydro-, (1.alpha.,4.alpha.,4a.alpha.,8a.alpha.)- |
21 |
1,5,9-Cyclododecanetriol |
Diethyl Phthalate |
Triallylphosphine $$ Phosphine, tri-2-propenyl- |
22 |
Cyclohexanone, 2-(1-hydroxyethyl)- |
1,3-Dioxolane, 2-phenyl-2-(phenylmethyl)- |
Chloroacetic acid, 2,2-dimethylpropyl ester |
23 |
Quinoline-5,8-dione-6-ol, 7-[[(4-cyclohexylbutyl)amino]methyl]- |
Phthalic acid, isoporpyl propyl ester |
3-Hexanol, 4,4-dimethyl- |
24 |
Tetracosane, 1-bromo- |
Benzofuran-2-one, 4-amino-2,3-dihydro- |
Cyclohexanol, 2,2,6,6-tetramethyl- |
25 |
Butanoic acid, 5-hexenyl ester |
Phthalic acid, 2-acethylphenyl ethyl ester |
Cyclododecanemethanol |
26 |
Tridecanal |
Ethyl tridecanoate |
Methanesulfonic acid, 2,7-dioxatricyclo [4.3.1.0 (3,8)] dec-5 -yl ester |
27 |
Z,Z -8,10 -Hexadecadien- 1-ol |
Tridecanoic acid |
Cyclohexane-1,3-dicarboxamide |
28 |
Toluene -4- sulfonic acid, 2,7-dioxatricyclo [4.3.1.0 (3,8)] dec-10-yl ester |
1,4-Butanediamine, N-(3-aminopropyl)- |
Propanal,3-hexylimino-2-nitro- |
29 |
Dispiro(2,4-dineopentyl-1,3-disilacyclobutan1,2';3,2''-bis[3-neopentyl-2-silatetracyclo[7.0.0 (1,5).0(4,8).0 (7,9)]nonan |
1,2 -Benzenedicarboxylic acid,bis(2-methylpropyl)ester |
2-Hydroxymethyl-2-methylcyclopentanol |
30 |
Cyclohexanol, 2-methylene-3-(1-methylethyl)-, cis- |
n-Hexadecanoic acid
|
2,2,4 -Trimethyl- 3 -(3,8,12,16-tetramethyl- heptadeca-3,7,11,15 -tetraenyl) cyclohexanol |
31 |
Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)- |
Ethyl tridecanoate |
2-Hydroxypentadecyl propanoate |
32 |
Cyclopropane,1-(1,2 -dimethylpropyl)-1-methyl-2-nonyl- |
7-Tetradecene |
2H -Azepin-2 -one, 5-(1,1-dimethylethyl) hexahydro- |
33 |
1-Pentatriacontanol |
2-Trifluoroacetoxydodecane |
Piperidine, 3,5-dimethyl- |
34 |
Trichloroacetic acid, undecyl ester |
3-Hexadecyne |
7-Tetradecenal, (Z)- |
35 |
Cyclohexane, (3,3-dimethylpentyl)- |
7-Tetradecenal, (Z)- |
Bicyclo[2.2.1]heptan-7-one-1-carboxylic acid, ethylene ketal-, t-butyl ester |
36 |
Octanoic acid, 2-butyl ester |
Acetic acid,1,3,7-trimethylocta- 2,6-dienyl ester |
Bicyclo[2.2.1]heptan-2-one, 5-hydroxy-4,7,7-trimethyl-, endo- |
37 |
1,3-Cyclohexanediol |
Exo- tricycle [6.2.1.0(2.7)] undecane |
Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)- |
38 |
beta.-D-Glucopyranoside, 4-nitrophenyl |
8,9,9,10,10,11 -Hexafluoro- 4,4-dimethyl -3,5-dioxatetracyclo [5.4.1.0(2,6).0(8,11)]dodecane |
2-Carboxymethyl-3-methyl-cyclopentanecarboxylic acid |
39 |
1,6-Cyclodecanediol |
Octadecanoic acid |
1-Heptadec-1-ynyl-cyclohexanol |
40 |
Propanal,3-hexylimino-2-nitro- |
Cyclohexanecarboxylic acid, 2-ethylcyclohexyl ester |
Octadecanoic acid |
*The cells marked with the same color indicate the common chemical compounds appeared in the pure extracts
Punica granatum Peel
20 g of sample with 400 mL of ethanol (70%) was mixed by magnetic stirrer for 2 hours, and then the sample was steeped for one day, filtered, and centrifuged (3000 C/min for 10 minutes) [14].
Preparation of mixture extracts
3 mixture extracts were prepared by mixing 30 mL of each extract of the pure extracts and mixing it with 30 mL of the other extract by means of a magnetic stirrer for 3 minutes after which the resulting mixture extracts were stored in refrigeration until use.
Analysis by using GC-MS technology
30 mL of each sample of the extracts (pure and mixed) were taken and sent well cooled to the GC MS lab in the Department of Food Sciences at the College of Agriculture/University of Basra/Iraq (Table 2).
Table 2: Analysis of GC-MS for mixtures alcoholic extracts
Peak |
GC-MS. For Mix. of Punica granatum peel & Ziziphusspina-christi leaves |
1 |
1-Butanol, 3-methyl-, acetate $$ Isoamylethanoate |
5 |
Propane, 1-(1 -methylethoxy)- $$ Ether,isopropyl propyl |
6 |
Ethanol, 2-(vinyloxy)- $$ Ethylene glycol monovinyl ether $$ Ethanol, 2-(ethenyloxy)- $$ Ethylene glycol vinyl ether $$ Ethyleneglycolmonovinyl ester $$ Vinyloxyethanol |
7 |
2-Isopropoxyethylamine $$ 2-Isopropoxyethanamine |
13 |
1,1-Diethoxy-3-methylbutane |
14 |
Ethyl 2,2-diethoxypropionate $$ Ethyl 2,2-diethoxypropanoate |
16 |
Benzene, 1,2,4 -trimethyl - $$ .psi.-Cumene |
17 |
Hexanoic acid , ethyl ester $$ Ethyl caproate |
19 |
Acetic acid, cyano- $$ Cyanoacetic acid $$ Malonicmononitrile $$ Monocyanoacetic acid $$ NCCH2COOH $$ 2-Cyanoacetic acid $$ Acidecyanacetique $$ USAF kf-17 |
21 |
3-Isothiazolecarboxamide, 4-amino- |
22 |
1-Adamantanemethylamine, .alpha.-methyl- $$ .alpha.-Methyladamantanemethylamine $$ .alpha.-Methyl-1-adamantanemethylamine $$ Rimantadine |
24 |
N-(4-[(4-Cyano-3,7-dimethylpyrido[1,2-a]benzimidazol-1-yl)amino]phenyl)acetamide |
27 |
Propanedioic acid, dihydroxy- $$ 2,2-Dihydroxymalonic acid |
28 |
Methoxyacetic acid, octyl ester $$ Octylmethoxyacetate |
30 |
Benzene, (1,1,2-trimethylpropyl)- $$ 2,3-Dimethyl-2-phenylbutane $$ (1,1,2-Trimethylpropyl)benzene |
32 |
Acetic acid, oxo - $$ Glyoxylic acid |
33 |
Benzene, m -diisopropyl |
35 |
Diethyl Phthalate |
36 |
2-Propyl-tetrahydropyran-3-ol |
37 |
n-Hexadecanoic acid |
38 |
4-Chloro-3-n-hexyltetrahydropyran $$ 4-Chloro-3-hexyltetrahydro-2H-pyran |
Peak |
GC-MS. for mix of Ziziphusspina-christi leaves and Eucalyptus camaldulensis leaves |
1 |
1-Butanol, 3-methyl-, acetate $$ Isoamylethanoate acetate |
3 |
Propanedioic acid, dihydroxy- $$ 2,2-Dihydroxymalonic acid |
7 |
Bicyclo [2.1.1 ]hex-2 -ene, 2-ethenyl- |
8 |
Propane, 1-(1-methylethoxy)- |
10 |
Butane, 1,1-diethoxy-3-methyl- |
11 |
Ethane, 1,1,1-triethoxy- $$ Orthoacetic acid, triethyl ester $$ Ethyl orthoacetate $$ Triethylorthoacetate $$ 1,1,1-Triethoxyethane |
12 |
Benzene, 1-ethyl-3-methyl- $$ Toluene, m-ethyl- |
13 |
Hexanoic acid,ethyl ester |
14 |
Eucalyptol $$ Cineole $$ 2-Oxabicyclo[2.2.2]octane, 1,3,3 -trimethyl |
15 |
Methoxyacetic acid, 2-pentyl ester |
16 |
4-Amino-2-oxy-furazan-3-carboxylic acid |
18 |
Acetic acid, ethoxyhydroxy-, ethyl ester $$ Ethyl ethoxy(hydroxy)acetate |
19 |
(3-Methyl-oxiran-2-yl)-methanol |
20 |
1,3-Cyclopentadiene, 1,2,3,4-tetramethyl-5-methylene- |
21 |
7,10-Epoxytricyclo[4.2.1.1(2,5)]decane, 1-trimethylsilyl- |
23 |
Benzene, 1,4-bis(1-methylethyl)- |
24 |
Acetic acid, oxo- $$ Glyoxylic acid |
25 |
2-(4,5-Dihydro-3 -methyl-5-oxo -1-phenyl-4-pyrazolyl)-5 -nitrobenzoic acid |
26 |
(-)-Spathulenol |
27 |
Diethyl Phthalate |
31 |
1,4 –Dioxaspiro [4.6] undec-8-ene, 7,10-methano- |
33 |
n-Hexadecanoic acid $$ Hexadecanoic acid |
38 |
Cyclopentanecarboxylic acid, |
Peak |
GC-MS for mix of Eucalyptus camaldulensis leaves and Pomegranate peels |
1 |
1-Butanol, 3-methyl-, acetate $$ Isoamylethanoate |
2 |
(S)-(+)-1-Cyclohexylethylamine $$ 1-Cyclohexylethanamine |
3 |
(S)-Isopropyl lactate $$ Propanoic acid, 2-hydroxy-, 1-methylethyl ester, (S)- $$ Isopropyl 2-hydroxypropanoate |
5 |
Propane, 1- (1-methylethoxy) - |
9 |
Butanoic acid, 3-hydroxy- $$ Butyric acid, 3-hydroxy- |
11 |
(2S,4S)-(+)-Pentanediol $$ 2,4-Pentanediol |
12 |
Propanedioic acid, dihydroxy- $$ 2,2-Dihydroxymalonic acid |
13 |
Butane, 1,1-diethoxy-3-methyl- |
14 |
Ethane, 1,1,1-triethoxy- $$ Orthoacetic acid, triethyl ester $$ Ethyl orthoacetate $$ Triethylorthoacetate $$ 1,1,1-Triethoxyethane |
16 |
Ketone, methyl 4-pyridyl, O-acetyloxime $$ (1E)-1-(4-Pyridinyl)ethanone o-acetyloxime |
17 |
Hexanoic acid, ethyl ester $$ Ethyl caproate |
18 |
Propanedioic acid, dihydroxy- $$ 2,2-Dihydroxymalonic acid |
21 |
Benzene, 1-methyl-4-(1-methylethyl)- $$ p-Cymene |
22 |
Eucalyptol |
23 |
Diglycerol $$ 1,2-Propanediol, 3,3'-oxybis- $$ .alpha.,.alpha.'-Diglycerol $$ Diglycerine |
24 |
1,3,5-Cycloheptatriene, 3,7,7-trimethyl- $$ 3,7,7-Trimethyl-1,3,5-cycloheptatriene |
25 |
2-(4,5-Dihydro-3 -methyl-5-oxo-1 -phenyl-4 -pyrazolyl)-5-nitrobenzoic |
28 |
1,7,7-Trimethyl-2-vinylbicyclo[2.2.1]hept-2-ene |
30 |
Cyclopentanemethanol, .alpha.-methyl- $$ 1-Cyclopentylethanol |
31 |
Cyclohexanepropanol, .alpha.-methyl- $$ 4-Cyclohexyl-2-butanol |
33 |
trans-Z-.alpha.-Bisabolene epoxide |
34 |
Diethyl Phthalate |
37 |
Clonitazene |
38 |
n -Hexadecanoic acid |
39 |
2,4-Decadien-1-ol $$ (2E,4E)-2,4-Decadien-1-ol |
40 |
Threitol,2-O -octyl- |
Results and Discussion
Alcoholic plant extracts and their mixtures
Figure 1 shows the types of plant alcoholic extracts of Ziziphus spina - christi leaves, Eucalyptus camaldolehsis leaves, and Punica granatum Peel.
Figure 2 displays the mixture alcoholic extracts of (Ziziphus spina - christi Eucalyptus camaldolehsis), (Ziziphus spina-Christi and Punica granatum), and (Eucalyptus camaldolehsis and Punica granatum).
Analysis of GC-MS for pure alcoholic plant extracts
Figure 3 depictes chromatogram of Eucalyptus camaldolehsis leaves extracts by using GC-MS technology.
Figure 1: Plants extracts
Figure 2: The mixture alcoholic extracts of Ziziphus spina - christi Eucalyptus camaldolehsis, Ziziphus spina – Christi and Punica granatum, and Eucalyptus camaldolehsis and Punica granatum
Figure 3: Chromatogram of Eucalyptus camaldolehsis leaves extracts by using GC-MS technology
Figures 4 displays chromatogram of Ziziphus spina-christi leaves extracts by using GC-MS technology.
Figures 5 illustrates chromatogram of Punica granatum peel extract by using GC-MS technology.
Analysis of GC-MS for mixture extracts
Figures 6 demonstrates chromatogram of mixture extracts (Ziziphus spina - christi leaves and Eucalyptus camaldolehsis leaves) by using GC-MS technology.
Figure 4: Chromatogram of Ziziphus spina - christi leaves extracts by using GC-MS technology
Figure 5: Chromatogram of Punica granatum peel extract by using GC-MS technology
Figure 6: Chromatogram of mixture extracts (Ziziphus spina - christi leaves and Eucalyptus camaldolehsis leaves) by using GC-MS technology
Figure 7: Chromatogram of mixture extracts (Eucalyptus camaldolehsis leaves and Punica granatum peel) by using GC-MS technology
Table 2: Analysis of GC-MS for mixtures alcoholic extracts
The study showed that the peaks demonstrated by the GC-MS analysis curves indicate the nature of the presented chemical compounds in the extracts, as this technique works to isolate the compounds at different times, and then diagnose them by determining their composition, molecular weight, and chemical formula, and they are diagnosed through the library data stored in the device.
The new chemical compounds were identified by using Gc-Ms technology for a mixture of Ziziphusspina-christi leaves extracts with Punica granatum peel. The chemical composition, molecular formula, and biological activity of the new compounds were indicated as in Table 3.
Table 3. Biological significance, chemical composition, and chemical formula of new compounds resulting from mixing Ziziphusspina-christi leaves extract with Punica granatum peel extract
No. |
Name of the Compound |
Biological activity |
1 |
Ethanol, 2-nitro- Or 2-nitroethanol |
Toxic effect as the vapor or mist of this compound irritates the eyes, upper respiratory tract, and mucous membranes [15]. |
2 |
2-isopropoxy ethyl amine Or 2-Aminoethyl Isopropyl Ether |
used to make medical narcotic and pesticide herbicide [16]. |
3 |
Methoxy acetic acid iso propyl ester or 1-methoxypropan-2-yl acetate |
Anti-cancer.Methoxyisopropyl acetate is used in surface coatings, and cleaners [17]. |
4 |
acetonitrite,bromo or 2-bromoacetonitrile |
Carcinogens [18] |
5 |
Benzene1,2,4-trimethyl |
It causes rapid breathing but has no effects on the central nervous system [19]. |
6 |
Acetic acid,cyano |
It is used as a chemical medium for malonic acid. Diethyl Malonate Pharmaceuticals. It is used to produce the fungicide cymoxanil and to treat dextromethorphan cough [20]. |
7 |
3-Isothiazolecarboxamide, 4-amino |
It is used as an antiviral drug. The isothiazole ring has also pharmacological activity. Likewise, the effect of structural modifications in the carboxylic group. Derivatives on their biological activity [22]. |
8 |
1-Adamantanemethylamine, .alpha.-methyl- |
Antiviral agents used in the prophylaxis or therapy of virus diseases. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; inhibiting viral protein synthesis. It is used as an anti-infection. It also works as antimicrobial agents and chemotherapy [22]. |
9 |
1-(4 -Acetamidoanilino)-3,7-dimethylbenzo [4,5] imidazo [1,2-a]pyridine-4 -carbonitrile |
Unknown activity |
10 |
Methoxyacetic acid, octyl ester |
Unknown activity |
11 |
Benzene, (1,1,2-trimethylpropyl |
Unknown activity |
12 |
Benzene, 1,3-bis(1-methylethyl |
It is used in various products and industries (e.g. in cosmetics, chemical manufacturing, production of metals, etc.).This compound is considered a risk, as continuous exposure to the vapors of this compound causes the early cancer cases and inhibits growth [23]. |
13 |
Hexanal |
Flavoring agents. Anti-fungal agents’ substances that eliminate fungi. Well used as insecticides designed to combat insects harmful to humans. Anti-microbial agents and anti-bacterial agente [24]. |
14 |
2-Propyl-tetrahydropyran-3-ol |
Anti-angiogenic effect [25] |
15 |
4-Chloro-3-n-hexyltetrahydropyran |
Unknown activity |
16 |
Cis -bicyclo[4.4.0] decan-1-ol-3-one |
Antibacterial activity of Eryngium maritimum L [26]. |
Likewise, the biological activity, chemical composition, and chemical formula of the new compounds listed in Table 4, which resulted from mixing Ziziphusspina-christi leaves extract with Eucalyptus camaldulensis leaves extract were studied. These new compounds were detected by using Gc-Ms technology.
The biological activity, chemical composition, and chemical formula listed in Table 5 were also studied for the new compounds resulting from mixing Eucalyptus camaldulensis extract with Punica granatum peels extract. These new compounds were detected by using the Gc-Ms.
Table 4: Biological significance, chemical composition, and chemical formula of new compounds resulting from mixing Ziziphusspina-christi leaves extract with Eucalyptus camaldulensis leaves extract
No. |
Name of the Compound |
Biological activity |
5 |
Bicyclo[ 2.1.1]hex-2-ene, 2 -ethenyl- |
Antifungal [27]. |
7 |
Benzene, 1-ethyl-3-methyl- |
Antimicrobial Activities, antioxidant, and antimicrobial agents [28]. |
8 |
Methoxyacetic acid, 2-pentyl ester |
Antimicrobial activity is reported [29]. |
9 |
4 -Amino-2-oxy -furazan-3 -carboxylic acid |
Unknown activity |
11 |
Acetic acid, ethoxyhydroxy-, ethyl ester |
Unknown activity |
12 |
(3-Methyl-oxiran-2-yl)-methanol |
Unknown activity |
13 |
1,3 -Cyclopentadiene,1,2,3,4-tetramethyl -5-methylene- |
Unknown activity |
14 |
7,10-Epoxytricyclo[4.2.1.1(2,5)]decane, 1-trimethylsilyl- |
Unknown activity |
15 |
Benzene, 1,4-bis(1-methylethyl) |
Antioxidant, Inhibitors of the interaction of thyroid hormone [30]. |
23 |
2-( 4,5-Dihydro-3-methyl -5-oxo-1-phenyl-4 -pyrazolyl)-5-nitrobenzoic acid |
It is used as pesticide, miticide, and weed killers, it also possess good antibacterial [31]. |
25 |
Acetic acid, cyano- |
It is used as a chemical medium for malonic acid. Diethyl Malonate Pharmaceuticals It is also used to produce the fungicide simoxanil and dextromethorphan cough treatment [32]. |
Table 5: Biological significance, chemical composition, and chemical formula of new compounds resulting from mixing Eucalyptus camaldulensis extract with Punica granatum peels extract
No. |
Name of the Compound |
Biological activity |
1 |
(S)-Isopropyl lactate |
It has a toxic effect that causes muscle weakness upon intramuscular injection [33]. |
2 |
1-Octanethiol |
Accelerators, activators, oxidation agents, reducing agents, etc. This compound have a toxic effect may be fatal if inhaled, ingested, or absorbed through skin [34]. |
3 |
Butanoic acid, 3-hydroxy |
It acts as an inhibitor of the hepatitis C virus (HCV). It is also used by the brain as a source of energy during fasting in humans or when blood glucose is low used in the synthesis of polyvinyl-co‐unsaturated acids resins, pharmaceutics [35]. |
4 |
2,4-Pentanediol |
Inhibitors of death of the malaria parasite plastid is also used to screen green cytotoxicity to monitor cytotoxicity in cells [36]. |
5 |
Ketone, methyl 4-pyridyl, O-acetyloxime |
Unknown activity |
6 |
Benzene, 1-methyl-4-(1-methylethyl) |
Used as flavoring agents, it also works to reduce acute lung injury caused by lipopolysaccharide (LPS) in vivo. Anatomic examination of lung tissue has shown that treatment with this compound reduces pneumonia and has a protective effect on the lung. Non-confidential commercial and consumer uses of p-cymene include polishes and sanitation goods, soaps, detergents, and other [37]. |
7 |
Diglycerol |
Has unique functions as a basic component of membranes, an intermediate in lipid metabolism [34]. |
8 |
1,3,5 -Cycloheptatriene, 3,7,7 -trimethyl |
It treats dementia and cognitive deficits in Parkinson's disease, and / or lack of learning, and memory in Parkinson'sdisease [38]. |
9 |
2-Thiazolidinethione |
It has various biological activities, such as bactericidal, pesticide, anti-convulsants, anti-tuberculosis, anti-flatulence, painkillers, anti-parasites, and herbicides, it also has the strong anti-HIV and anti-cancer [39]. |
10 |
Cyclopentanemethanol, .alpha.-methyl |
Anti-cancer Drug [34]. |
11 |
Cyclohexanepropanol, .alpha.-methyl |
Against several bacteria and fungi [30]. |
12 |
Trans -Z-.alpha.-Bisabolene epoxide |
Biological activity and anti-microbes [33]. |
13 |
Clonitazene |
Unknown activity |
14 |
2,4-Decadien-1-ol |
Identification of antagonists of small molecules of thyroid receptors, an assay of small molecule stimuli of vitamin D [39]. |
15 |
Threitol, 2-O-octyl- |
Unknown activity |
Conclusion
It can be mentioned that the preparation of three mixture extracts prepared by mixing (1:1) two of each of the pure extracts separately, demonstrated us new chemical compounds that differ from the chemical compounds appeared in the pure extracts, by conducting chemical analysis by using the GC-MS technique. These new chemical compounds were identified in each of the prepared extract blends and their benefits are theoretically studied. It should be noted that this these compounds are naturally present in other sources or may be chemically prepared in the laboratory, but they are not presented in the original extracts from which they were prepared, and therefore it is a simple and new way to mix pure extracts and prepare new chemical compounds with different biological activity.
Acknowledgments
Thanks and appreciation to the College of Agriculture, University of Basra, which facilitated the conduct of the GC-MS test in the GC-MS laboratory. Our thanks and appreciation to prof. Abduladheem Turki Jalil.
Funding
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
Authors' contributions
All authors contributed to data analysis, drafting, and revising of the paper and agreed to be responsible for all the aspects of this work.
Conflict of Interest
There are no conflicts of interest in this study.
ORCID
Maryam Mansoor Mathkoor
https://www.orcid.org/0000-0001-9397-3941
Noor Abd-Ulamer Oda
https://orcid.org/0000-0002-5430-6940
HOW TO CITE THIS ARTICLE
Maryam Mansoor Mathkoor, Eussur Noory Alkhfaji, Noor Abd- ulamer Oda. Using GC-MS technology to identify the compounds resulting from mixing of alcoholic extracts of some medicinal plants. J. Med. Chem. Sci., 2023, 6(3) 486-499