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Journal of Stress Physiology & Biochemistry, Vol. 20, No. 4, 2024, pp. 52-62 ISSN 1997-0838 Original Text Copyright © 2024 by Basel Saleh
ORIGINAL ARTICLE
open access
Phytochemical Analysis of Artemisia herba alba Asso
(Asteraceae) Species
Basel Saleh
1 Department of Molecular Biology and Biotechnology, Atomic Energy Commission of Syria, P.O. Box 6091, Damascus, Syria
*E-Mail: [email protected]
Received May 24, 2024
Phytochemical analysis of Artemisia herba-alba Asso (Asteraceae) species has been carried out using fourier-transform infrared spectroscopy (FT-IR) technique and gas chromatography-mass spectrometry (GC-MS) analyses. FT-IR spectra of the aerial parts (buds AB, leaves AL and flowers AF) of A. herba-alba powder revealed the presence of 12 peaks, of which 11 common peaks characteristics of the three A. herba-alba studied aerial parts. Whereas, the peak of 1632 cm-1 [(assigned to Alkenyl C=C stretch-Olefinic (alkene) group)] was observed in AB and AF aerial parts and not in AL. As for GC-MS analysis, data revealed 12 & 10 chemical compounds classes in A. herba-alba buds extracts of which, Bicyclic monoterpenoids (37.026 & 49.022%) was presented as a major compound in methanolic and ethanolic buds extracts, respectively. Whereas, 17 & 14 chemical compounds classes were detected in A. herba-alba leaves extracts, of which, Fatty acid amides (28.687 & 25.687%) was presented as a major compound in methanolic and ethanolic leaves extracts, respectively. While, 16 & 11 chemical compounds classes were detected in A. herba-alba flowers extracts, of which Fatty acid amides (25.623 & 23.295%) was presented as a major compound in methanolic and ethanolic flowers extracts, respectively. These bioactive materials make this species as a good candidates for different pharmaceutical and medicine academic researches and applications.
Key words: Artemisia herba-alba, FT-IR, GC-MS, Phytochemical analysis
Artemisia is a genus belongs to Asteraceae family, and includes approximately 300 species of small herbs and shrubs (Dob and Benabdelkader, 2006). In Syrian Flora, Artemisia genus is represented with about 5 species (Mouterde, 1983), of which Artemisia herba-alba species wild grown in Syria.
Artemisia herba-alba Asso, known as desert wormwood and as shTeh in Arabic. It is a perennial shrub grows commonly on the dry steppes of the Mediterranean regions in Northern Africa (Saharan Maghreb), Western Asia (Arabian Peninsula) and Southwestern Europe (USDA, 2010).
Abou EL-Hamd et al. (2010) reported that the sesquiterpene lactones, flavonoids, phenolic compounds & waxes and essential oils were isolated and identified as the main secondary metabolites from A. herba-alba and other Artemisia species.
It has been reported that the Artemisia genus has an important role in folk medicine by many cultures since ancient times (European medicine, North Africa and Arabic traditional medicine) (Moufid and Eddouks, 2012). Of which, A. herba-alba herb exhibited many medicinal properties e.g. as anti-diabetic, antimicrobial, antioxidant, antiradical, antispasmodic, antihypertensive, antimalarial, anthelmintic, antileishmanial, nematicidal, neurological pesticidal, allelopathic and cytoprotective activities (Abou EL-Hamd et al., 2010; Moufid and Eddouks, 2012; Janackovic et al., 2016; Younsi et al., 2016; Ouchelli et al., 2022; Kadri et al., 2022; Houti et al., 2023).
Moufid and Eddouks (2012) reported that A. herba alba biological activity could mainly related to its content of many bioactive compounds e.g. herbalbin, cis-chryanthenyl acetate, flavonoids (hispidulin and cirsilineol), monoterpenes and sesquiterpene.
Phytochemical screening of natural products presented in plants species is requested for any pharmaceutical and medicine researches and applications. In this regards, many different analytical methods have been employed to determine Artemisia phytochemical constituents; e.g. fourier-transform infrared spectroscopy (FT-IR) (Hameed et al., 2016) and
ultra-performance liquid chromatography (UPLC) coupled to photodiode array detection (PDA) and mass spectrometry (MS) (UPLC-PDA-MS) (Dane et al., 2015).
Gas chromatography-mass spectrometry (GC-MS) analysis has been extensively used for phytochemical screening of A. herba-alba species worldwide ((Bellili et al., 2016; Janackovic et al., 2016; Younsi et al., 2016; Amkiss et al., 2021; Ouguirti et al., 2021; Kadri et al., 2022; Ouchelli et al., 2022; Houti et al., 2023).
Little is known about phytochemical screening of A. herba-alba species in Syria. Thereby, the presented study focused on its phytochemical analysis during different growth stages using FT-IR and GC-MS analyses.
MATERIALS AND METHODS Plant materials and samples preparation
Artemisia herba-alba Asso aerial parts (10 plants/part) including buds (AB), leaves (AL) and flowers (AF) were collected separately from wild A. herba-alba species grown in their natural habitat from rural Damascus regions-Syria (altitude of 950 m and annual rainfall of 240 mm). Samples were shade dried for two weeks, and were milled to fine powder by special electric mill and stored separately in glass bowls until FT-IR and GC-MS analyses. FT-IR analysis
The fine powder was used as template for FT-IR analysis in the wavenumber range of 3500-500 cm-1. IR measurement has been performed using NXR FTIR (Thermo, USA) instrument for FT-IR analysis. Plants extracts preparation
The fine powder for each sample was extracted with methanol and ethanol solvents, separately as flowing: 1 g of fine powder was extracted with 10 mL solvent overnight, filtrated with filter papers (Whatman no.1). Then, all extracts were kept in tightly fitting stopper bottles and stored at 4 °C. The final obtained extracts were then analyzed using GC-MS analysis.
GC-MS analysis
GC Chromatec-Crystal 5000 system, supported with Chromatec Crystal Mass Spectrometry Detector (Chromatec, Russia) has been employed to investigate
phytochemical methanolic and ethanolic A. herba-alba aerial parts extracts analysis. GC-MS analysis has been performed according to the following conditions: The range scan was 42-850 MU, the column [(BP-5-MS (30 m x 0.25 mm x 0.25 |jm)], carrier gas (0.695 ml/min flow of Helium gas). Oven temperature was programmed initially at 35 °C for 1 min, then an increase by 10°C /1 min till 220 °C, then increase to 230 °C by 1°C /1 min followed by 10 °C /1 min increasing till 255 °C (hold for 5 min). Injector temperature was 275 °C and detector temperature was 280 °C and ionization energy was 70 ev.
RESULTS AND DISCUSSION
FT-IR spectra wavelength of the aerial parts (buds AB, leaves AL and flowers AF) of A. herba-alba powder was presented in Figure 1. FT-IR analysis revealed the presence of 12 peaks, of which 11 common peaks characteristics of the three A. herba-alba studied aerial parts (Table 1). These common peaks were: 876 cm-1 (assigned to =C-H oop bend-Aromatics group); 1055 cm-1 [(assigned to Methyne (CH-) Cyclohexane ring vibrations-Saturated aliphatic (alkane/alkyl) group)]; 1160, 1364 and 1733 cm-1 (assigned to C-O secondary alcohol stretch C-O stretch-Ethers group); 1265 cm-1 (assigned to C-O stretch-Carboxylic acid group); 1445 & 1515 cm-1 (assigned to C=C stretch aromatic-Aromatics group); 2850 and 2924 cm-1 (assigned to C-H stretch-Alkanes group) and 3425 cm-1 (assigned to Hydroxy group, H-bonded OH stretch-Alcohol and hydroxyl group). Whereas, the peak of 1632 cm-1 [(assigned to Alkenyl C=C stretch-Olefinic (alkene) group)] was observed in AB and AF aerial parts and not in AL.
Artemisia herba-alba aerial parts (buds AB, leaves AL and flowers AF) grown in rural Damascus regions, were phytochemically analyzed using FT-IR technique. Overall, FTIR spectra showed Aromatics (3 groups), Ethers (3 groups), Alkanes (2 groups), Saturated aliphatic (alkane/alkyl) (1 group), Carboxylic acids (1 group) and Alcohol & hydroxy (1 group) as common functional groups. Whereas, Olefinic (alkene) group was observed in AB and AF aerial parts and not in AL.
As for GC-MS analysis, chromatogram of the aerial parts of methanolic buds (A), ethanolic buds (B), methanolic leaves (C), ethanolic leaves (D), methanolic
flowers (E) and ethanolic flowers (F) A. herba-alba extracts using GC-MS analysis has been presented in Figure 2.
It worth noting that the chemical compounds classes presented in scare amounts (< 1%) did not recorded. GC-MS data revealed 12 & 10 chemical compounds classes in A. herba-alba buds extracts of which, Bicyclic monoterpenoids (37.026 & 49.022%) was presented as a major compound in methanolic and ethanolic buds extracts, respectively (Table 2). Otherwise, 7 common chemical compounds classes were detected in A. herba-alba buds extracts: Bicyclic monoterpenoids (37.026 & 49.022%), Bicyclic ether (10.057 & 10.083%), Monoterpenoids (1.876 & 2.708%), Long-chain fatty acids (1.255 & 2.061%), Fatty acid amides (15.471 & 11.283%), Carboximidic acids (11.851 & 5.929%) and Sesquiterpenoids (2.155 & 6.188%) in methanolic and ethanolic buds extracts, respectively (Table 2).
Whereas, 17 & 14 chemical compounds classes were detected in A. herba-alba leaves extracts, of which, Fatty acid amides (28.687 & 25.687%) was presented as a major compound in methanolic and ethanolic leaves extracts, respectively (Table 3). Otherwise, 5 common chemical compounds classes were detected in A. herba-alba leaves extracts: Fatty acid amides (28.687 & 25.687%), Bicyclic ether (5.392 & 8.789%), Bicyclic monoterpenoids (2.325 & 2.581%), Fatty amides (21.275 & 19.683%) and ClassyFire Class: Fatty acyls (4.659 & 7.920%) in methanolic and ethanolic leaves extracts, respectively (Table 3).
While, 16 & 11 chemical compounds classes were detected in A. herba-alba flowers extracts, of which Fatty acid amides (25.623 & 23.295%) was presented as a major compound in methanolic and ethanolic flowers extracts, respectively (Table 4). Otherwise, 9 common chemical compounds classes were detected in A. herba-alba flowers extracts: Fatty acid amides (25.623 & 23.295%), Bicyclic ether (11.879 & 9.408%), Bicyclic monoterpenoids (4.000 & 13.144%), Stereoisomers (3.139 & 9.479%), Monoterpene ketone (2.815 & 6.729%), Long-chain fatty acids (24.808 & 1.123%), Fatty amides (2.649 & 5.560%), Terpenoids (3.366 & 3.639%) and Eudesmane
sesquiterpenoid (7.145 & 6.462%) in methanolic and ethanolic flowers extracts, respectively (Table 4).
GC-MS analysis has been extensively employed for A. herba-alba essential oils (EOs) phytochemical analysis worldwide. In this regards, Abou El-Hamd et al. (2010) reported that 1,8-Cineole (50%), Thujone (27%), Terpinen-4-ol (3.3%), Borneol (3%) and Camphor (3%) were major compounds in EOs A. herba-alba from Egypt. Whereas, Tilaoui et al. (2015) reported the difference in phytochemicals presented in EOs A. herba-alba from Morocco, according to the plant parts used. In this respect, p-thujone was found to be 1.24, 7.00 and 6.14 % and Verbenol was found to be 2.16, 5.99 and 21.83% in leaves, capitulum and aerial parts, respectively. Whereas, Eucalyptol (1,8-Cineole) was found to be 20.37, 7.71, 1.49 and 2.27% in leaves, stems, capitulum and aerial parts, respectively. Moreover, Fekhar et al. (2017) reported that the major compounds recorded in Algerian A. herba-Alba EOs were Camphor (32.98%), a-Thujone (18.43%), p-Thujone (16.62%) and p-Cymene (13.19%). While, Mohammadhosseini (2017) reported that Camphor (0.240.3%), 1,8-Cineole (0.1-19.3%), p-Pinene (0.7-23.6%), Sabinene (0.2-18.6%), Camphene (0.2-24.2%) and a-Pinene (1.1-13.9%) were the major compounds
recorded in A. herba alba species according to the collection sites in Iran.
Other phytochemical researches have been carried out in other Artemisia species using different analytical methods. In this regards, Kumar and Kumud (2010) reported the occurrence of phytosterol, saponins, carbohydrate, tannin, flavonoids, phenolic compounds, amino acid and proteins in hexane and methanolic A. vulgaris aerial parts extracts. Whereas, Ruwali et al. (2015) reported the occurrence of reducing sugars, carbohydrates, tri-terpenoids, sterols, glycosides, phenolics and flavonoids in methanol, ethanol and hydro-methanol A. indica aerial parts extracts. Moreover, Dane et al. (2015) reported the occurrence of flavonoid glycosides, flavonoid aglycones and phenolic acids in methanolic A. absinthium extracts using UPLC-PDA-MS analysis. Indeed, Enas et al. (2015) reported the presence of flavonoids, tannins, saponin, alkaloids, phenols, steroids and glycosides in acetonic A. annua extracts. Whereas, Hameed et al. (2016) reported the occurrence of C-H Alkenes, C-F stretch Aliphatic fluoro compounds, C-O Alcohols, Ethers, Carboxlic acids, Esters and H-O H-bonded H-X group in methanolic A. annua extracts using FT-IR analysis.
Table 1: Observed functional groups in aerial parts of A. herba-alba using FT-IR analysis.
Peak N° IR frequency (cm-1) Observed IR (cm-1) Bond Functional groups
1 900-690 876 =C-H oop bend Aromatics
Methyne (CH-) Cyclohexane ring Saturated aliphatic
2 1055-1000 1055 vibrations (alkane/alkyl)
C-O secondary alcohol stretch C-O
3 2000-1000 1160 stretch Ethers
4 1300-1200 1265 C-O stretch Carboxylic acids
C-O secondary alcohol stretch C-O
5 2000-1000 1364 stretch Ethers
6 1600-1400 1445 C=C stretch aromatic Aromatics
7 1600-1400 1515 C=C stretch aromatic Aromatics
8 1680-1620 1632 Alkenyl C=C stretch Olefinic (alkene)
C-O secondary alcohol stretch C-O
9 2000-1000 1733 stretch Ethers
10 2970-2850 2850 C-H stretch Alkanes
11 2970-2850 2924 C-H stretch Alkanes
12 3570-3200 3425 Hydroxy group, H-bonded OH stretch Alcohol and hydroxy
S
'55 —
0} с
h-
LL
FT-IR shift (cm"1)
Figure 1. FT-IR spectra wavelength of the aerial parts (buds AB, leaves AL and flowers AF) of A. herba-alba.
Table 2: Chemical compounds class observed in methanolic and ethanolic A. herba-alba buds extracts using GC-MS analysis.
Methanolic buds extracts
Peak No RT (min) Compound class Peak area (%)
1 9.505 Bicyclic ether 10.057
2 10.695 Bicyclic monoterpenoids 37.026
3 10.865 Stereoisomers 4.631
4 11.344 Monoterpenoids 1.876
5 23.558 Long-chain fatty acids 1.255
6 24.252 Endogenous fatty acid amide 4.402
7 25.074 Carboximidic acids 8.527
8 26.776 Cannabinoids (CBs) ligands 1.868
9 29.513 Fatty acid amides 15.471
10 30.159 Carboximidic acids 3.324
11 30.446 Sesquiterpenoids 2.155
12 32.826 Eudesmane sesquiterpenoid 6.500
Ethanolic buds extracts
Peak No RT (min) Compound class Peak area (%)
1 9.501 Bicyclic ether 10.083
2 10.704 Bicyclic monoterpenoids 49.022
3 11.342 Monoterpenoids 2.708
4 25.047 Carboximidic acids 5.929
5 26.745 Furopyrans 1.431
6 29.480 Fatty acid amides 11.283
7 30.138 Long-chain fatty acids 2.061
8 30.404 Esquiterpene 1.837
9 31.956 ClassyFire Class: Fatty acyls 1.031
10 32.786 Sesquiterpenoid 6.188
Figure 2. Chromatogram of the aerial parts of methanolic buds (A), ethanolic buds (B), methanolic leaves (C), ethanolic leaves (D), methanolic flowers (E) and ethanolic flowers (f) A. herba-alba extracts using GC-MS analysis.
Table 3: Chemical compounds class observed in methanolic and ethanolic A. herba-alba leaves extracts using GC-MS
analysis.
Methanolic leaves extracts
Peak No RT (min) Compound class Peak area (%)
1 9.505 Bicyclic ether 5.392
2 10.854 Stereoisomers 1.417
3 11.356 Monoterpenoids 4.660
4 12.941 Bicyclic monoterpenoids 1.168
5 21.404 Carboxylic ester 1.905
6 24.269 Diterpenoid 12.611
7 25.063 Fatty amides 12.304
8 25.549 Fatty amides 1.274
9 26.799 Terpenoid 6.218
10 27.483 Bicyclic monoterpenoids 1.157
11 28.037 Fatty amides 2.137
12 29.530 Fatty acid amides 28.687
13 29.980 Terpenoids 1.181
14 30.163 Fatty amides 4.504
15 30.435 Sesquiterpenoids 4.462
16 32.756 ClassyFire Class: Fatty acyls 4.659
17 33.773 Fatty amides 1.356
Ethanolic leaves extracts
Peak No RT (min) Compound class Peak area (%)
1 8.159 Monoterpenes 1.028
2 9.493 Bicyclic ether 8.789
3 10.681 Bicyclic monoterpenoids 2.581
4 11.348 Monoterpene ketone 14.494
5 12.937 Menthane monoterpenoids 2.176
6 22.278 Fatty aldehydes 1.427
7 25.003 Fatty amides 16.142
8 26.713 ClassyFire Class: Fatty acyls 7.920
9 27.479 Eremophilane 1.428
10 29.434 Fatty acid amides 25.687
11 29.933 Triterpene 1.397
12 30.117 Fatty amides 3.541
13 30.368 Polysaccharide 5.325
14 32.687 Ester 3.651
Table 4: Chemical compounds class observed in methanolic and ethanolic A. herba-alba flowers extracts using GC-MS
analysis.
Methanolic flowers extracts
Peak No RT (min) Compound class Peak area (%)
1 9.506 Bicyclic ether 11.879
2 10.691 Bicyclic monoterpenoids 4.000
3 10.867 Stereoisomers 3.139
4 11.356 Monoterpene ketone 2.815
5 21.423 Long-chain fatty acids. 4.232
6 23.775 Fatty amides 1.366
7 24.281 Long-chain fatty acids 9.805
8 25.070 Long-chain fatty acids 10.771
9 26.791 Terpenoids 3.366
10 27.729 Fatty amides 2.649
11 29.538 Fatty acid amides 25.623
12 30.157 Carboximidic acids 3.661
13 30.429 Sesquiterpenoids 1.280
14 31.452 ClassyFire Class: Fatty acyls 1.196
15 32.784 Eudesmane sesquiterpenoid 7.145
16 33.766 Saturated long-chain fatty acid 1.456
Methanolic flowers extracts
Peak No RT (min) Compound class Peak area (%)
1 9.493 Bicyclic ether 9.408
2 10.687 Bicyclic monoterpenoids 13.144
3 10.861 Stereoisomers 9.479
4 11.358 Monoterpene ketone 6.729
5 24.998 Fatty amides 16.452
6 26.701 Terpenoids 3.639
7 29.419 Fatty acid amides 23.295
8 30.088 Fatty amides 5.560
9 31.916 Triterpenoids 1.730
10 32.234 Long-chain fatty acids 1.123
11 32.677 Eudesmane sesquiterpenoid 6.462
In other researches, different number of phytochemical compounds in essential oils (EOs) or/and extracts of A. herba-alba aerial parts using GC-MS analysis was detected; e.g. 152 chemical compounds were observed in Tunisian A. herba-alba EOs (Bellili et al., 2016); 75, 74 and 45 chemical compounds were observed in Libyan A. judaica L., A. herba alba Asso. and A. arborescens L. (cultivated) EOs, respectively
(Janackovic et al., 2016); 23 chemical compounds were observed in Tunisian A. herba-alba EOs (Younsi et al., 2016); 28 chemical compounds were observed in Algerian A. herba-alba EOs (Ouguirti et al., 2021); 21 chemical compounds were observed in Moroccan A. herba-alba ethanolic extract (Amkiss et al., 2021); 79 chemical compounds were observed in Algerian A. herba-alba EOs (Ouchelli et al., 2022); 39 chemical compounds were observed in Algerian A. herba-alba
EOs (Kadri et al., 2022) and 50 chemical compounds were observed in Moroccan A. herba-alba EOs (Houti et al., 2023).
In the current study, the observed functional groups in A. herba alba using FT-IR have been reported for their biological activity in different researches; e.g. carboxylic acid served as anti-inflammatory drugs (NSAIDs), antibiotics, anticoagulants, and cholesterol-lowering (Saleh, 2020) or as anticancer and antifertility (Hameed et al., 2016); Aromatic group as isonicotinamide, antimicrobial and anti-inflammatory agents (Saleh, 2020) and the Ether group as antifungal and antimicrobial agents (Hameed et al., 2016).
In conclusion, A. herba-alba aerial parts (buds AB, leaves AL and flowers AF) grown in rural Damascus regions, were phytochemically analyzed using FT-IR and GC-MS techniques. Overall, FT-IR spectra showed Aromatics (3 groups), Ethers (3 groups), Alkanes (2 groups), Saturated aliphatic (alkane/alkyl) (1 group), Carboxylic acids (1 group) and Alcohol & hydroxy (1 group) as common functional groups. Whereas, Olefinic (alkene) group was observed in AB and AF aerial parts and not in AL. As for GC-MS analysis, data revealed 12 & 10 chemical compounds classes in A. herba-alba buds extracts of which, Bicyclic monoterpenoids (37.026 & 49.022%) was presented as a major compound in methanolic and ethanolic buds extracts, respectively. Whereas, 17 & 14 chemical compounds classes were detected in A. herba-alba leaves extracts, of which, Fatty acid amides (28.687 & 25.687%) was presented as a major compound in methanolic and ethanolic leaves extracts, respectively. While, 16 & 11 chemical compounds classes were detected in A. herba-alba flowers extracts, of which Fatty acid amides (25.623 & 23.295%) was presented as a major compound in methanolic and ethanolic flowers extracts, respectively, some of these bioactive compounds worldwide exhibited a known potential biological role. However, for the other ones, more future performance experiments for determine their unknown potential activities are requested in pharmaceutical aspect.
ACKNOWLEDGEMENTS
I thank Dr. I. Othman (Director General of AECS) and Dr. A. Almariri (Head of Molecular Biology and Biotechnology Department in AECS) for their support, and also the Plant Biotechnology group for technical assistance.
CONFLICTS OF INTEREST
The authors declare that they have no potential conflicts of interest.
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