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Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives
Open accessAbstract
Anethum graveolens is an aromatic plant traditionally used as an antispasmodic and carminative. The objective of this study is to analyze the chemical composition of the essential oils and extracts obtained from seeds gathered in Errachidia, southern Morocco. Additionally, the antioxidant and antimicrobial properties of these oils and extracts will be evaluated. GC-MS analysis of the EO isolated by hydrodistillation revealed that its main compounds were E-anethole (38.13%), estragole (29.32%), fenchone (17.21%), and α-pinene (7.37%). The phenolic components were extracted using the methods of decoction and Soxhlet. The assay of the phenolic compounds showed that A. graveolens seeds contained considerable amounts of polyphenols, flavonoids, and condensed tannins, with variable levels depending on the extract analyzed. HPLC/UV-ESI-MS analyses performed on the decoction revealed a structural diversity of the molecules present in this extract, the most important of which were umbelliferone (12.35%), 3-hydroxyflavone (11.23%), rosmanol (8.95%), biotin (8.36%), emmotin H (4.91%), and coumarin (4.21%). The antioxidant activity, as determined by three techniques (DPPH•, FRAP, and CAT), demonstrated that the essential oils (EOs) and extracts had a potent capacity to counteract detrimental free radicals, control the generation of reactive oxygen species, and mitigate oxidative damages. The antimicrobial activity of the Eos and extracts was carried out in a liquid medium against five strains (E. cloacae, K. pneumoniae, E. coli, S. aureus, and S. epidermidis) and four candidiasis (C. albicans, C. dubliniensis, C. tropicalis, and C. parapsilosis) and Aspergillus niger. The results showed the effectiveness of the EOs compared to the aqueous, ethanolic, and decoction extracts against most of the microorganisms tested. In addition, the ethanolic extract showed antifungal activity that was distinguished from that of the other extracts. The antimicrobial efficacy of the essential oils under study can primarily be attributed to the synergistic interactions among its three principal constituents (E-anethole, estragole, and fenchone). Furthermore, molecular docking and molecular dynamics simulation results reveal significant interactions and stability between the selected bioactive compounds and different target proteins involved in antimicrobial and antioxidant activities. Compounds like 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol exhibited better binding energies with the explored proteins, indicating their potential as antimicrobial and antioxidant agents. Finally, our findings emphasize the significance of A. graveolens seeds as a promising reservoir of advantageous health compounds that can serve as organic substitutes for the presently employed synthetic preservatives.
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TL;DR
This study characterizes *Anethum graveolens* seed essential oil and extracts from southern Morocco and evaluates their antioxidant and antimicrobial potential in vitro and in silico. It reports (E)-anethole-rich essential oil, phenolic-rich ethanolic extract, broad antimicrobial activity, and docking/MD evidence for selected compounds as possible natural preservative candidates.
Key findings
- GC-MS of the hydrodistilled seed essential oil identified (E)-anethole (38.13%), estragole (29.32%), fenchone (17.21%), and α-pinene (7.37%) as main compounds; oil yield was 2.73 ± 0.12% and density 0.9362 ± 0.0732 g/mL.
- HPLC/UV-ESI-MS of the decoction identified 38 compounds, including umbelliferone (12.35%), 3-hydroxyflavone (11.23%), rosmanol (8.95%), biotin (8.36%), emmotin H (4.91%), and coumarin (4.21%).
- Antioxidant activity was strongest in the ethanolic extract: DPPH IC50 = 46.90 ± 0.73 μg/mL, FRAP EC50 = 161.33 ± 6.18 μg/mL, and total antioxidant capacity = 72.97 ± 0.71 mg EAA/g E; the essential oil had a DPPH IC50 of 9.02 mg/mL.
- Antimicrobial testing showed essential oil MIC/MFC values of 3.125–6.25 μL/mL, with *A. niger* and *C. dubliniensis* most sensitive at 3.13 μL/mL; extracts had MIC/MFC values of 0.78–50 mg/mL, with *A. niger* most sensitive at 0.78 mg/mL. Docking highlighted 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol, with binding energies such as methyl rosmarinate–2CAG (−10.2 kcal/mol) and 1-caffeoyl-beta-D-glucose–3NRZ (−10 kcal/mol).
Methods
- Seeds of *A. graveolens* from Errachidia, southern Morocco, were used; essential oil was obtained by hydrodistillation, and phenolic extracts by decoction and Soxhlet extraction with water or ethanol/water.
- Chemical profiling used GC-MS for the essential oil and HPLC/UV-ESI-MS for the decoction; total phenolics, flavonoids, and condensed tannins were quantified spectrophotometrically.
- Antioxidant activity was assessed by DPPH•, FRAP, and total antioxidant capacity assays; antimicrobial activity was tested in liquid medium against five bacterial and five fungal strains, with MIC, MBC, and MFC determination. In silico work used PASS, ADMET/ProTox II, molecular docking with AutoDock Vina, and 100 ns GROMACS molecular dynamics simulations.
Limitations
- The paper states that further research, including rigorous clinical trials, is necessary to conclusively verify no long-term risks to consumers, and that the compounds still require FDA approval for medical use.
- The text makes evident that the biological findings are based on in vitro assays and in silico predictions, with no human, animal, or food-matrix preservation trials reported.
- The antimicrobial evaluation is limited to specific hospital-derived strains, and the paper repeatedly notes that essential oil yield and composition vary with origin, extraction method, and environmental factors, which limits direct generalizability.
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In the paper
“None of the chemical compounds of the studied essential oil act as inhibitors of P-gp I and P-gp II, and the main constituents of the essential oil are also not P-gp substrates.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.11. Prediction of PASS Activity, ADME, Toxicity (ProTox II), and Efficacy for Potentially Active Compounds Isolated from the Essential Oil and Aqueous Extract of A. graveolens Seeds
plain- Asserted: passes — The authors put it forward as true.
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In the paper
“The results of our study reveal that among the tested compounds, 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol presented the greatest binding energies with the exploratory proteins.”
- Also stated in: § 2.13. Molecular Dynamics Simulation · plain
“Among these compounds, 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol exhibited the highest binding energies with the explored proteins.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.12. Molecular Docking
plainstates an association- Asserted: passes — The authors put it forward as true.
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- Load-bearing: passes — The paper’s conclusions depend on it.
- Based: passes — The paper gives a reason why it holds.
- Also stated in: § 2.13. Molecular Dynamics Simulation · plain
A result the paper reports from its own data — it cites no other source for it, so there is none to check. The quote shows it is in the paper.
In the paper
“In contrast, for the studied compounds in the aqueous extract, we observed that compounds such as 3-hydroxyflavone, rosmanol, methyl rosmarinate, homovanillic acid, 1-caffeoyl-beta-D-glucose, and kaempferol can be P-gp substrates.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.11. Prediction of PASS Activity, ADME, Toxicity (ProTox II), and Efficacy for Potentially Active Compounds Isolated from the Essential Oil and Aqueous Extract of A. graveolens Seeds
plain- Asserted: passes — The authors put it forward as true.
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In the paper
“The majority of the isolated compounds studied, eight out of a total of sixteen, obtained an SNC score greater than -3.0, suggesting that they easily cross the blood-brain barrier (BBB).”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.11. Prediction of PASS Activity, ADME, Toxicity (ProTox II), and Efficacy for Potentially Active Compounds Isolated from the Essential Oil and Aqueous Extract of A. graveolens Seeds
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In the paper
“Upon examining the RMSD graph displayed in Figure 12, it can be observed that all the protein–ligand entities had a reduced variation in their spectrum. This indicates that there was a minimal disturbance in their conformational dynamics over the whole simulation.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.13. Molecular Dynamics Simulation
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In the citing paper
“A. graveolens has been reported in the literature to exhibit various biological activities, including antimicrobial, antifungal, antioxidant, insecticidal, antiinflammatory, antispasmodic, antidiabetic, anticancer and antihypercholesterolemic properties6,9.”
From Synergistic and antagonistic contributions of main components to the bioactivity profile of Anethum graveolens extract (2025) · cites this paper as [6]
In the citing paper
“The TPC values range between 169.4 ± 0.5 and 177.3 ± 0.5 mg GAE/g extract were higher than those previously reported for A. graveolens preparations, including values of 7.06–19.09 mg GAE/g dry extract [31] and 23.35–52.65 mg GAE/g extract [32].”
From Maceration, Soxhlet Extraction, and Steam Hydrodistillation of Anethum graveolens Seeds: Phytochemical Profiles and Cytotoxic Effects (2026) · cites this paper as [32]
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§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.1. Quality Control of Plant Material
“we utilized atomic absorption spectrophotometry to analyze the concentration of six specific heavy metals”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 3. Materials and Methods > 3.3. Quality Control of Plant Material
“The analysis of the heavy metals in A. graveolens seeds was conducted using the technique of Inductively Coupled Plasma Atomic Emission Spectrometry”
Rated major: it would touch a result — a value a result rests on, reported and recomputed p-values on opposite sides of the significance level, two passages that conflict with no sign which is right, or a cited work retracted before this paper was published.
In the paper
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.10. Antimicrobial Activity
“Regarding the essential oil, the MICs and MFCs ranged between 3.125 and 6.25 μL/mL.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.10. Antimicrobial Activity
“The highest MICs and MFCs of 50 μL/mL were observed in Candida tropicalis and Candida parapsilosis.”
Rated major: it would touch a result — a value a result rests on, reported and recomputed p-values on opposite sides of the significance level, two passages that conflict with no sign which is right, or a cited work retracted before this paper was published.
In the paper
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.10. Antimicrobial Activity
“the ethanolic extract exhibited a similar action on all the tested bacterial strains except for the Enterobacter cloacae strain, where it was inactive.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.10. Antimicrobial Activity
“Additionally, the three tested extracts did not exert any power on wild-type E. coli and S. epidermidis.”
Rated minor: it would not touch a result — a value no result rests on, a p-value that stays on the same side of the significance level, or a conflict that is clerical, resolved elsewhere in the paper, or outside its own findings.
In the paper
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.7. Chromatographic Analysis by HPLC/UV-ESI-MS of the Extracts
“biotin was detected by an [M+H]+ ion at m/z = 243”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.7. Chromatographic Analysis by HPLC/UV-ESI-MS of the Extracts
“The ion at m/z = 297 could result from the loss of a part of the biotin’s side structure”
Rated minor: it would not touch a result — a value no result rests on, a p-value that stays on the same side of the significance level, or a conflict that is clerical, resolved elsewhere in the paper, or outside its own findings.
In the paper
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.13. Molecular Dynamics Simulation
“The antifungal and antibacterial activities of the extracts and essential oils were observed to have minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) ranging from 0.78 to 50 mg/mL and 3.125 to 6.25 μL/mL, respectively.”
§ Phytochemical Analysis and Evaluation of Antioxidant and Antimicrobial Properties of Essential Oils and Seed Extracts of Anethum graveolens from Southern Morocco: In Vitro and In Silico Approach for a Natural Alternative to Synthetic Preservatives > 2. Results & Discussion > 2.10. Antimicrobial Activity
“the essential oil inhibited and destroyed the E. cloacae, K. pneumoniae, and wild-type E. coli strains at a concentration of 25 μL/mL. Meanwhile, S. aureus and S. epidermidis appeared to be less sensitive, with higher MBCs of 50 μL/mL.”
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In the paper
“Balahbib, 2023, Fenchone and Camphor: Main Natural Compounds from Lavandula stoechas, L., Expediting Multiple In Vitro Biological Activities, Heliyon, 9, e21222, 10.1016/j.heliyon.2023.e21222”
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Bamagous, G. A., Ibrahim, I. A. A., Alzahrani, A. R., Shahid, I., Shahzad, N., Falemban, A. H., Alanazi, I. M., Hussein‐Al‐Ali, S. H., Arulselvan, P., & Thangavelu, I. (2024) · Journal of Inorganic and Organometallic Polymers and Materials · doi:10.1007/s10904-024-03447-z · Cited by 42
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Metabolomic analysis of bioactive compounds in dill (Anethum graveolens L.) extracts
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Metadata
- Authors
- Hadi, N., Drioiche, A., Bouchra, E. M., Baammi, S., Abdelaziz Shahat, A., Tagnaout, I., Radi, M., Remok, F., Bouzoubaa, A., & Zair, T.
- Affiliations
- Université Moulay Ismail de Meknes (MA)
- Research Team of Chemistry of Bioactive Molecules and the Environment, Laboratory of Innovative Materials and Biotechnology of Natural Resources, Faculty of Sciences, Moulay Ismaïl University, B.P. 11201, Zitoune, Meknes 50070, Morocco
- Université Mohammed VI Polytechnique (MA)
- Pharmacognosy Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
- Corresponding author
- Drioiche, Aziz
- Zair, Touriya
- Venue
- Pharmaceuticals
- Publisher
- MDPI AG
- Published
- 2024-07-01
- Volume
- 17
- Issue
- 7
- Pages
- 862
- ISSN
- 1424-8247 (ISSN-L)
- PMC
- PMC11280095
- OpenAlex
- W4400292961
- Cited by
- 30
- References
- 78
- Citations by year
- 2026: 12 · 2025: 14 · 2024: 4
- FWCI
- 4.97
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Pharmaceuticals (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- King Saud University, Riyadh, Saudi Arabia (RSPD2024R1057)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant chemical constituents analysis
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Medicinal Plant Research
- Keywords
- dill, seed extract, phytochemical composition, antioxidant activity, antimicrobial activity, antifungal activity, antibacterial activity, (E)-anethole, estragole, fenchone, phenolic compounds, flavonoids, proanthocyanidins, coumarins, umbelliferone, natural preservatives, food preservatives
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