Research Article
Ranunculus arvensis L. Çı̇çek Polenlerı̇nı̇n Fenolı̇k Bı̇leşı̇mı̇ ve Antı̇oksı̇dan Özellı̇klerı̇: in Vı̇tro ve Siliko Görüşler
Abstract
Ranunculus arvensis L., zehirli bir bitki olarak sınıflandırılmasına rağmen, tıp, gıda ve arıcılıkta önemli bir değere sahiptir. Poleni, bal arıları da dahil olmak üzere çeşitli arı türleri tarafından aktif olarak toplanır ve larvaları için hayati bir besin rezervi olarak depolanır. Bu çalışma, R. arvensis çiçek poleninin polifenol ve flavonoid içeriğinin yanı sıra antioksidan özelliklerini araştırmaktadır. Nahçıvan Özerk Cumhuriyeti'nden elde edilen polenin antioksidan aktivitesi FRAP yöntemi kullanılarak 179,102 ± 1,5919 μmol FeSO₄-7H₂O/g dw ve DPPH yöntemi kullanılarak 0,137 ± 0,015 mg/mL olarak ölçülmüştür. Metanolik ekstraktın fenolik içeriği 17.952 ± 0.160 mg/g, flavonoid içeriği ise 5.660 ± 0.055 mg/g olarak belirlenmiştir. HPLC yoluyla yapılan fenolik profilleme altı temel bileşiği tanımlamıştır: ferulik asit (521.163 µg/g), kafeik asit (170.119 µg/g), p-hidroksibenzoik asit (46.529 µg/g), protokateşuik asit (22.377 µg/g), krisin (11.353 µg/g) ve pinokembrin (10.953 µg/g). Kuantum kimyası hesaplamaları, en bol bulunan fenolik bileşikler olan ferulik asit ve kafeik asidin antioksidan aktivite için en uygun profilleri sergilediğini ortaya koymuştur. Bu bulgular, bu iki bileşiğin polen ekstraktının antioksidan potansiyeline birincil katkıda bulunan bileşikler olduğunu göstermektedir. Arı ürünlerinin besinsel ve farmakolojik önemi göz önüne alındığında, çiçek poleninin fitokimyasal bileşiminin sürekli araştırılması, fonksiyonel özelliklerinin daha iyi anlaşılması için gereklidir.
References
- Abd El-Wahab, T.E., Ghania, A.M.M. and Zidan, E.W. Assessment a new pollen supplement diet for honey bee colonies and their effects on some biological activities./ Journal of Agricultural Technology, 2016; Vol. 12(1):55-62
- Albaba, İ. A List of Important Honeybee Nectariferous and Polleniferous Plant Species in the West Bank Governorates, Palestine / Journal of Agricultural Science and Technology A. 2015; 5(2), 114-121 doi: 10.17265/2161-6256/2015.02.005
- Al-Snafi, A. E. Pharmacological and toxicological effects of the Ranunculus species (Ranunculus arvensis and Ranunculus sceleratus) grown in Iraq. Int. J. Biol. Pharm. Sci. Arch, 2022; 3, 64-72. Article DOI: https://doi.org/10.53771/ijbpsa.2022.3.1.0032
- An, İ., Ucmak, D., Esen, M., & Gevher, O. D. Phytocontact dermatitis due to Ranunculus arvensis: Report of three cases. North. Clin. Istanb, 2019, 6(1), 81-84. doi: 10.14744/nci.2018.93695
- Benzie, I. F., & Strain, J. J. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical biochemistry, 1996, 239(1), 70-76. https://doi.org/10.1006/abio.1996.0292
- Boroomand, N., Sadat-Hosseini, M., Moghbeli, M., & Farajpour, M. Phytochemical components, total phenol and mineral contents and antioxidant activity of six major medicinal plants from Rayen, Iran. Natural product research, 2018, 32(5), 564-567. http://dx.doi.org/10.1080/14786419.2017.1315579
- Boulebd, H. Insights on the antiradical capacity and mechanism of phytocannabinoids: H-abstraction and electron transfer processes in physiological media and the influence of the acid-base equilibrium. Phytochemistry, 2023; 208, 113608. https://doi.org/10.1016/j.phytochem.2023.113608
- Boulebd, H. Is cannabidiolic acid an overlooked natural antioxidant? Insights from quantum chemistry calculations. New Journal of Chemistry, 2022; 46 (1), 162-168. DOI: 10.1039/D1NJ04771J.
- Boulebd, H. Mechanistic Insights into the Antioxidant and Pro-oxidant Activities of Bromophenols from Marine Algae: A DFT Investigation. The Journal of Organic Chemistry, 2024; 89 (11), 8168-8177. https://doi.org/10.1021/acs.joc.4c00851.
- Boulebd, H.; Pereira, D. M.; Amine Khodja, I.; Hoa, N. T.; Mechler, A.; Vo, Q. V. Assessment of the free radical scavenging potential of cannabidiol under physiological conditions: Theoretical and experimental investigations. Journal of Molecular Liquids, 2022; 346, 118277. DOI: 10.1016/j.molliq.2021.118277.
- De-Melo AAM., Estevinho LM., Moreira MM., Delerue-Matos C., Freitas AS., Barth OM., Almeida-Muradian LB. Phenolic profile by HPLC-MS, biological potential, and nutritional value of a promising food: Monofloral bee pollen/ J Food Biochem.; 2018; 1-21 https://doi.org/10.1111/jfbc.12536
- Erdogan, T. F., Kivcak, B., Onur, M. A., & Braca, A. Chemical constituents and cytotoxic activity of Ranunculus pedatus subsp. pedatus. Chemistry of Natural Compounds, 2012; 48, 486-488. DOI: 10.1007/s10600-012-0284-3.
- Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.; M. A. Robb; J. R. Cheeseman; G. Scalmani et al. Gaussian 09, Gaussian, Inc., Wallingford CT, 2009.
- Fukumoto, L. R., & Mazza, G. Assessing antioxidant and prooxidant activities of phenolic compounds. Journal of agricultural and food chemistry, 2000; 48(8), 3597-3604. https://doi.org/10.1021/jf000220w.
- Galano, A.; Alvarez-Idaboy, J. R. Kinetics of radical-molecule reactions in aqueous solution: A benchmark study of the performance of density functional methods. Journal of Computational Chemistry, 2014; 35 (28), 2019-2026. DOI: 10.1002/jcc.23715.
- Hachelaf, A., Touil, A., Zellagui, A., & Rhouati, S. Antioxidant and antibacterial activities of essential oil extracted from Ranunculus arvensis L. Der Pharma Chem, 2015, 7(9):170-173.
- Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual molecular dynamics. Journal of Molecular Graphics, 1996; 14 (1), 33-38. https://doi.org/10.1016/0263-7855(96)00018-5.
- Jürgens, A., & Dötterl, S. Chemical composition of anther volatiles in Ranunculaceae: genera‐specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species. American Journal of Botany, 2004; 91(12), 1969-1980. DOI: 10.3732/ajb.91.12.1969.
- Kolaylı, S., Asadov, E., Huseynova, A., Rahimova, S., & Kara, Y. Phenolic composition and antioxidant properties of black mulberry (Morus nigra l.) fruits and leaves. Journal of Wildlife and Biodiversity, 2024; 8(2), 355-364. DOI: https://doi.org/10.5281/zenodo.11078022.
- Kostic, A., Milincic, D.D., Nedic, N., Gašic, U.M., Trifunovic, B., Vojt, D. et al. Phytochemical Profile and Antioxidant Properties of Bee-Collected Artichoke (Cynara scolymus) Pollen. Antioxidants- 2021; 10(7), 1091. https://doi.org/10.3390/antiox10071091.
- Kurkin, V. Pharmacognosy. Textbook for students of pharmaceutical universities (faculties). Samara: OFORT LLC, State Educational Institution of Higher Professional Education "Sam GMU", 2004; 1180 p.
- Lu, T.; Chen, F. Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 2012; 33 (5), 580-592. DOI: 10.1002/jcc.22885.
- Lü, J.-M.; Lin, P. H.; Yao, Q.; Chen, C. Chemical and molecular mechanisms of antioxidants: experimental approaches and model systems. Journal of Cellular and Molecular Medicine, 2010; 14 (4), 840-860. DOI: 10.1111/j.1582-4934.2009.00897.x
- Molyneux, P. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. sci. technol, 2004; 26(2), 211-219.
- Pulido, R., Bravo, L., & Saura-Calixto, F. Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay. Journal of agricultural and food chemistry, 2000; 48(8), 3396-3402. DOI: 10.1021/jf9913458.
- Sadeq, O.; Mechchate, H.; Es-safi, I.; Bouhrim, M.; Jawhari, F.z.; Ouassou, H.; Kharchoufa, L. et al. Phytochemical Screening, Antioxidant and Antibacterial Activities of Pollen Extracts from Micromeria fruticosa, Achillea fragrantissima, and Phoenix dactylifera. Plants, 2021; 10, 676. https://doi.org/ 10.3390/plants10040676.
- Sedivy, C., Piskorski, R., Müller, A., & Dorn, S. Too low to kill: concentration of the secondary metabolite ranunculin in buttercup pollen does not affect bee larval survival. Journal of chemical ecology, 2012. 38, 996-1002. DOI 10.1007/s10886-012-0153-3
- Slinkard, K., & Singleton, V. L. Total phenol analysis: automation and comparison with manual methods. American journal of enology and viticulture, 1997; 28(1), 49-55. DOI:10.5344/ajev.1977.28.1.49.
- Spiegel, M. Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity. Journal of Chemical Information and Modeling, 2022; 62 (11), 2639-2658. https://doi.org/10.1021/acs.jcim.2c00104.
- Talibov, T. H., & Ibrahimov, A. S. Taxonomic spectre of the flora of Nakhchivan Autonomous Republic. Nakhchivan: Ajamy, 2008, 364.
- Zehra, C., Yildiz, O., Şahin, H., Asadov, A., & Kolayli, S. Phenolic profile and antioxidant potential of propolis from Azerbaijan. Mellifera, 2015, 15(1), 16-28.
PHENOLIC COMPOSITION AND ANTIOXIDANT PROPERTIES OF RANUNCULUS ARVENSIS L. FLOWER POLLEN: IN VITRO AND SILICO INSIGHTS
Abstract
Ranunculus arvensis L., although classified as a poisonous plant, holds significant value in medicine, food, and apiculture. Its pollen is actively collected by various bee species, including honeybees, and stored as a vital nutritional reserve for their larvae. This study investigates the polyphenol and flavonoid content, as well as the antioxidant properties, of R. arvensis flower pollen. The antioxidant activity of the pollen, sourced from the Nakhchivan Autonomous Republic, was measured as 179.102 ± 1.5919 μmol FeSO₄·7H₂O/g dw using the FRAP method and 0.137 ± 0.015 mg/mL using the DPPH method. The phenolic content of the methanolic extract was determined to be 17.952 ± 0.160 mg/g, while the flavonoid content was 5.660 ± 0.055 mg/g. Phenolic profiling via HPLC identified six key compounds: ferulic acid (521.163 µg/g), caffeic acid (170.119 µg/g), p-hydroxybenzoic acid (46.529 µg/g), protocatechuic acid (22.377 µg/g), chrysin (11.353 µg/g), and pinocembrin (10.953 µg/g). Quantum chemistry calculations revealed that ferulic acid and caffeic acid, the most abundant phenolic compounds, exhibited the most favorable profiles for antioxidant activity. These findings suggest that these two compounds are the primary contributors to the antioxidant potential of the pollen extract. Given the nutritional and pharmacological significance of bee products, continued investigation into the phytochemical composition of flower pollen is essential to better understand its functional properties and applications.
References
- Abd El-Wahab, T.E., Ghania, A.M.M. and Zidan, E.W. Assessment a new pollen supplement diet for honey bee colonies and their effects on some biological activities./ Journal of Agricultural Technology, 2016; Vol. 12(1):55-62
- Albaba, İ. A List of Important Honeybee Nectariferous and Polleniferous Plant Species in the West Bank Governorates, Palestine / Journal of Agricultural Science and Technology A. 2015; 5(2), 114-121 doi: 10.17265/2161-6256/2015.02.005
- Al-Snafi, A. E. Pharmacological and toxicological effects of the Ranunculus species (Ranunculus arvensis and Ranunculus sceleratus) grown in Iraq. Int. J. Biol. Pharm. Sci. Arch, 2022; 3, 64-72. Article DOI: https://doi.org/10.53771/ijbpsa.2022.3.1.0032
- An, İ., Ucmak, D., Esen, M., & Gevher, O. D. Phytocontact dermatitis due to Ranunculus arvensis: Report of three cases. North. Clin. Istanb, 2019, 6(1), 81-84. doi: 10.14744/nci.2018.93695
- Benzie, I. F., & Strain, J. J. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical biochemistry, 1996, 239(1), 70-76. https://doi.org/10.1006/abio.1996.0292
- Boroomand, N., Sadat-Hosseini, M., Moghbeli, M., & Farajpour, M. Phytochemical components, total phenol and mineral contents and antioxidant activity of six major medicinal plants from Rayen, Iran. Natural product research, 2018, 32(5), 564-567. http://dx.doi.org/10.1080/14786419.2017.1315579
- Boulebd, H. Insights on the antiradical capacity and mechanism of phytocannabinoids: H-abstraction and electron transfer processes in physiological media and the influence of the acid-base equilibrium. Phytochemistry, 2023; 208, 113608. https://doi.org/10.1016/j.phytochem.2023.113608
- Boulebd, H. Is cannabidiolic acid an overlooked natural antioxidant? Insights from quantum chemistry calculations. New Journal of Chemistry, 2022; 46 (1), 162-168. DOI: 10.1039/D1NJ04771J.
- Boulebd, H. Mechanistic Insights into the Antioxidant and Pro-oxidant Activities of Bromophenols from Marine Algae: A DFT Investigation. The Journal of Organic Chemistry, 2024; 89 (11), 8168-8177. https://doi.org/10.1021/acs.joc.4c00851.
- Boulebd, H.; Pereira, D. M.; Amine Khodja, I.; Hoa, N. T.; Mechler, A.; Vo, Q. V. Assessment of the free radical scavenging potential of cannabidiol under physiological conditions: Theoretical and experimental investigations. Journal of Molecular Liquids, 2022; 346, 118277. DOI: 10.1016/j.molliq.2021.118277.
- De-Melo AAM., Estevinho LM., Moreira MM., Delerue-Matos C., Freitas AS., Barth OM., Almeida-Muradian LB. Phenolic profile by HPLC-MS, biological potential, and nutritional value of a promising food: Monofloral bee pollen/ J Food Biochem.; 2018; 1-21 https://doi.org/10.1111/jfbc.12536
- Erdogan, T. F., Kivcak, B., Onur, M. A., & Braca, A. Chemical constituents and cytotoxic activity of Ranunculus pedatus subsp. pedatus. Chemistry of Natural Compounds, 2012; 48, 486-488. DOI: 10.1007/s10600-012-0284-3.
- Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.; M. A. Robb; J. R. Cheeseman; G. Scalmani et al. Gaussian 09, Gaussian, Inc., Wallingford CT, 2009.
- Fukumoto, L. R., & Mazza, G. Assessing antioxidant and prooxidant activities of phenolic compounds. Journal of agricultural and food chemistry, 2000; 48(8), 3597-3604. https://doi.org/10.1021/jf000220w.
- Galano, A.; Alvarez-Idaboy, J. R. Kinetics of radical-molecule reactions in aqueous solution: A benchmark study of the performance of density functional methods. Journal of Computational Chemistry, 2014; 35 (28), 2019-2026. DOI: 10.1002/jcc.23715.
- Hachelaf, A., Touil, A., Zellagui, A., & Rhouati, S. Antioxidant and antibacterial activities of essential oil extracted from Ranunculus arvensis L. Der Pharma Chem, 2015, 7(9):170-173.
- Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual molecular dynamics. Journal of Molecular Graphics, 1996; 14 (1), 33-38. https://doi.org/10.1016/0263-7855(96)00018-5.
- Jürgens, A., & Dötterl, S. Chemical composition of anther volatiles in Ranunculaceae: genera‐specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species. American Journal of Botany, 2004; 91(12), 1969-1980. DOI: 10.3732/ajb.91.12.1969.
- Kolaylı, S., Asadov, E., Huseynova, A., Rahimova, S., & Kara, Y. Phenolic composition and antioxidant properties of black mulberry (Morus nigra l.) fruits and leaves. Journal of Wildlife and Biodiversity, 2024; 8(2), 355-364. DOI: https://doi.org/10.5281/zenodo.11078022.
- Kostic, A., Milincic, D.D., Nedic, N., Gašic, U.M., Trifunovic, B., Vojt, D. et al. Phytochemical Profile and Antioxidant Properties of Bee-Collected Artichoke (Cynara scolymus) Pollen. Antioxidants- 2021; 10(7), 1091. https://doi.org/10.3390/antiox10071091.
- Kurkin, V. Pharmacognosy. Textbook for students of pharmaceutical universities (faculties). Samara: OFORT LLC, State Educational Institution of Higher Professional Education "Sam GMU", 2004; 1180 p.
- Lu, T.; Chen, F. Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 2012; 33 (5), 580-592. DOI: 10.1002/jcc.22885.
- Lü, J.-M.; Lin, P. H.; Yao, Q.; Chen, C. Chemical and molecular mechanisms of antioxidants: experimental approaches and model systems. Journal of Cellular and Molecular Medicine, 2010; 14 (4), 840-860. DOI: 10.1111/j.1582-4934.2009.00897.x
- Molyneux, P. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. sci. technol, 2004; 26(2), 211-219.
- Pulido, R., Bravo, L., & Saura-Calixto, F. Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay. Journal of agricultural and food chemistry, 2000; 48(8), 3396-3402. DOI: 10.1021/jf9913458.
- Sadeq, O.; Mechchate, H.; Es-safi, I.; Bouhrim, M.; Jawhari, F.z.; Ouassou, H.; Kharchoufa, L. et al. Phytochemical Screening, Antioxidant and Antibacterial Activities of Pollen Extracts from Micromeria fruticosa, Achillea fragrantissima, and Phoenix dactylifera. Plants, 2021; 10, 676. https://doi.org/ 10.3390/plants10040676.
- Sedivy, C., Piskorski, R., Müller, A., & Dorn, S. Too low to kill: concentration of the secondary metabolite ranunculin in buttercup pollen does not affect bee larval survival. Journal of chemical ecology, 2012. 38, 996-1002. DOI 10.1007/s10886-012-0153-3
- Slinkard, K., & Singleton, V. L. Total phenol analysis: automation and comparison with manual methods. American journal of enology and viticulture, 1997; 28(1), 49-55. DOI:10.5344/ajev.1977.28.1.49.
- Spiegel, M. Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity. Journal of Chemical Information and Modeling, 2022; 62 (11), 2639-2658. https://doi.org/10.1021/acs.jcim.2c00104.
- Talibov, T. H., & Ibrahimov, A. S. Taxonomic spectre of the flora of Nakhchivan Autonomous Republic. Nakhchivan: Ajamy, 2008, 364.
- Zehra, C., Yildiz, O., Şahin, H., Asadov, A., & Kolayli, S. Phenolic profile and antioxidant potential of propolis from Azerbaijan. Mellifera, 2015, 15(1), 16-28.
There are 31 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Entomology |
| Journal Section | Research Articles |
| Authors | |
| Early Pub Date | May 26, 2025 |
| Publication Date | May 30, 2025 |
| Submission Date | February 2, 2025 |
| Acceptance Date | April 15, 2025 |
| Published in Issue | Year 2025 Volume: 25 Issue: 1 |
Important Note: Since the author-referee information is kept confidential on both sides in our journal, both the author and the referees must upload the document to the system after removing their personal information in the review document section.
Note: Authors can also use homepage of our Journal.
https://creativecommons.org/licenses/by-nc-nd/4.0/
This work is licensed under Attribution-NonCommercial-NoDerivatives 4.0 International.