Quantitative analysis of phenolics in Trifolium pratense L. flowers and evaluation of antioxidant activity by sensory

Year 2024, , 165 - 174, 31.08.2024

Ramazan Erenler , İbrahim Hosaflıoğlu , İlyas Yıldız , Mehmet Nuri Atalar , Süleyman Muhammed Çelik , Mehmet Hakkı Alma

https://doi.org/10.54187/jnrs.1529229

Abstract

Trifolium pratense L. flowers (TPF) were collected and dried in shade in this study. After extraction in methanol, a diluted solution was applied to the liquid chromatography electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) device to determine the bioactive compounds quantitatively. Isoquercitrin (38.64 mg/g extract), coumarin (13.66 mg/g extract), and catechin (12.52 mg/g extract) were verified as major products. Antioxidant activity of TPF was performed using a potentiometric PVC membrane sensor to evaluate 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and total phenolic content of TPF. TPF inhibited the DPPH radical as 31.4 ± 0.02% at the 500-ppm concentration. However, the DPPH activity of gallic acid was determined as 81.43 ± 0.07% and 92.44 ± 0.1% at the TPF concentrations of 12.5 ppm and 25 ppm, respectively. In addition, the total phenolic content was calculated to be 82.4 ± 0.15 mg gallic acid eq/g extract. It was observed that TPF has the potential to be an antioxidant and a valuable source of isoquercitrin, coumarin, and catechin.

Keywords

Trifolium pratense, Natural compounds, Quantification, Sensory, Antioxidant activity

Ethical Statement

No approval from the Board of Ethics is required.

References

• G. Topçu, R. Erenler, O. Çakmak, C. B. Johansson, C. Çelik, H.-B. Chai, J. M. Pezzuto, Diterpenes from the berries of Juniperus excelsa, Phytochemistry 50 (7) (1999) 1195-1199.
• M. Elmastas, L. Ozturk, I. Gokce, R. Erenler, H. Y. Aboul‐Enein, Determination of antioxidant activity of marshmallow flower (Althaea officinalis L.), Analytical Letters 37 (9) (2004) 1859-1869.
• A. Sahin Yaglioglu, B. Akdulum, R. Erenler, I. Demirtas, I. Telci, S. Tekin, Antiproliferative activity of pentadeca-(8E, 13Z) dien-11-yn-2-one and (E)-1,8-pentadecadiene from Echinacea pallida (Nutt.) Nutt. roots, Medicinal Chemistry Research 22 (6) (2013) 2946-2953.
• R. Erenler, I. Telci, M. Ulutas, I. Demirtas, F. Gul, M. Elmastas, O. Kayir, Chemical constituents, quantitative analysis and antioxidant activities of Echinacea purpurea (L.) Moench and Echinacea pallida (Nutt.) Nutt, Journal of Food Biochemistry 39 (5) (2015) 622-630.
• R. Erenler, I. Demirtas, T. Karan, F. Gul, O. Kayir, O. C. Karakoc, Chemical constituents, quantitative analysis and insecticidal activities of plant extract and essential oil from Origanum onites L, Trends in Phytochemical Research 2 (2) (2018) 91-96.
• R. Erenler, İ. Telci, M. Elmastaş, H. Akşit, F. Gül, A. R. Tüfekçi, İ. Demirtaş, Ö. Kayir, Quantification of flavonoids isolated from Mentha spicata in selected clones of Turkish mint landraces, Turkish Journal of Chemistry 42 (6) (2018) 1695-1705.
• N. Genç, M. Elmastaş, İ. Telci, R. Erenler, Quantitative analysis of phenolic compounds of commercial basil cultivars (Ocimum basilicum L.) by LC-TOF-MS and their antioxidant effects, International Journal of Chemistry and Technology 4 (2) (2020) 179-184.
• R. Erenler, E. N. Geçer, M. H. Alma, İ. Demirtas, Quantitative analysis of bioactive compounds by high‑performance liquid chromatography in origanum bilgeri, Journal of Integrative and Anatolian Medicine 4 (1) (2022) 15-20.
• C. Yaman, Ş. Önlü, H. Ahmed, R. Erenler, Comparison of phytochemicals and antioxidant capacity of Hypericum perforatum; wild plant parts and in vitro samples, Journal of Animal & Plant Sciences 32 (2) (2022) 596-603.
• M. N. Atalar, R. Erenler, F. Turkan, M. H. Alma, I. Demirtas, A. Baran, S. I. Kandemir, A. I. Kekec, F. Z. Saltan, Phytochemical analysis and biological activity of Corchorus olitorius L.: Quantitative analysis of bioactive compounds by LC–MS/MS, antibacterial, enzyme inhibition, and cytotoxic activities, European Journal of Integrative Medicine 62 (2023) Article ID 102290 7 pages.
• R. Erenler, M. N. Atalar, İ. Yıldız, E. N. Geçer, A. Yıldırım, İ. Demirtas, M. H. Alma, Quantitative analysis of bioactive compounds by LC-MS/MS from Inula graveolens, Journal of Integrative and Anatolian Medicine 4 (3) (2023) 3-10.
• A. Saidi, L. Hambaba, B. Kucuk, E. Cacan, R. Erenler, Phenolic profile, acute toxicity, and hepatoprotective and antiproliferative activities of algerian ruta tuberculata forssk, Current Bioactive Compounds 18 (3) (2022) 72-83.
• Z. Heyem, B. Nassima, M. Ahmed, R. Erenler, Z. Lahcene, B. Fadila, S. Ameddah, Phytochemical profile, anti-lipid peroxidation and anti-diabetic activities of Thymus algeriensis Boiss. & Reut, Egyptian Journal of Chemistry 65 (12) (2022) 695-705.
• F. Z. Houari, R. Erenler, A. Hariri, Biological activities and chemical composition of Rubia tinctorum (L.) root and aerial part extracts thereof, Acta Biológica Colombiana 27 (3) (2022) 403-414.
• R. Erenler, T. Karan, İ. Hosaflioglu, Phytochemical analysis of Syringa vulgaris: Quantitative analysis of natural compounds by LC-ESI-MS/MS, Turkish Journal of Biodiversity 6 (2) (2023) 75-78.
• R. Erenler, C. Yaman, I. Demirtas, M. H. Alma, Phytochemical Investigation of Hypericum heterophyllum Flowers: LC-ESI-MS/MS analysis, total phenolic and flavonoid contents, antioxidant activity, The Natural Products Journal 13 (7) (2023) Article ID 120123212672 8 pages.
• Y. Başar, R. Erenler, Phytochemical analysis of Silybum marianum flowers: Quantitative analysis of natural compounds and molecular docking application, Turkish Journal of Biodiversity 7 (1) (2024) 20-31.
• R. Erenler, O. Cakmak, Synthesis of hexabromo, hydroxy, epoxy, methoxy and nitroxy derivatives of tetralins and naphthalenes, Journal of Chemical Research (8) (2004) 566-569.
• R. Erenler, J. F. Biellmann, Facile conversion of pyridine propargylic alcohols to enones: Stereochemistry of protonation of allenol, Tetrahedron Letters 46 (34) (2005) 5683-5685.
• O. Cakmak, R. Erenler, A. Tutar, N. Celik, Synthesis of new anthracene derivatives, Journal of Organic Chemistry 71 (5) (2006) 1795-1801.
• R. Erenler, J. F. Biellmann, Synthesis of pentafluorophenyl- and pyridinyl-3 allenes, Journal of the Chinese Chemical Society 54 (1) (2007) 103-108.
• R. Erenler, M. Uno, T. V. Goud, J. F. Biellmanna, Preparation of some heterocyclic enones and ynones by isomerisation of the propargylic alcohols, Journal of Chemical Research 2009 (7) (2009) 459-464.
• J. Lu, I. Maezawa, S. Weerasekara, R. Erenler, T. D. T. Nguyen, J. Nguyen, L. Z. Swisher, J. Li, L.W. Jin, A. Ranjan, S. K. Srivastava, D. H. Hua, Syntheses, neural protective activities, and inhibition of glycogen synthase kinase-3β of substituted quinolines, Bioorganic and Medicinal Chemistry Letters 24 (15) (2014) 3392-3397.
• R. Erenler, S. Yilmaz, H. Aksit, O. Sen, N. Genc, M. Elmastas, I. Demirtas, Antioxidant activities of chemical constituents isolated from Echinops orientalis Trauv, Records of Natural Products 8 (1) (2014) 32-36.
• E. A. T. Khodja, R. A. Abd El Hamid Khabtane, D. Benouchenne, M. S. Bensaad, C. Bensouici, R. Erenler, In vitro assessment of antioxidant, neuroprotective, anti-urease and anti-tyrosinase capacities of Tamarix africana leaves extracts, Journal of Traditional Chinese Medicine 43 (2) (2023) 252.
• M. Elmastaş, İ. Telci, H. Akşit, R. Erenler, Comparison of total phenolic contents and antioxidant capacities in mint genotypes used as spices, Turkish Journal of Biochemistry 40 (6) (2015) 456-462.
• R. Erenler, O. Sen, H. Aksit, I. Demirtas, A. S. Yaglioglu, M. Elmastas, İ. Telci, Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities, Journal of the Science of Food and Agriculture 96 (3) (2016) 822-836.
• R. Erenler, T. Adak, T. Karan, M. Elmastas, I. Yildiz, H. Aksit, G. Topcu, M. A. Sanda, Chemical Constituents isolated from Origanum solymicum with Antioxidant activities, The Eurasia Proceedings of Science, Technology, Engineering & Mathematics 1 (2017) 139-145.
• R. Erenler, B. Meral, O. Sen, M. Elmastas, A. Aydin, O. Eminagaoglu, G. Topcu, Bioassay-guided isolation, identification of compounds from Origanum rotundifolium and investigation of their antiproliferative and antioxidant activities, Pharmaceutical Biology 55 (1) (2017) 1646-1653.
• A. Guzel, H. Aksit, M. Elmastas, R. Erenler, Bioassay-guided isolation and identification of antioxidant flavonoids from Cyclotrichium origanifolium (Labill.) Manden. and Scheng., Pharmacognosy Magazine 13 (50) (2017) 316-320.
• R. Erenler, E. N. Gecer, N. Genc, D. Yanar, Antioxidant activity of silver nanoparticles synthesized from Tagetes erecta L. leaves, International Journal of Chemistry and Technology 5 (2) (2021) 141-146.
• E.N. Gecer, Green synthesis of silver nanoparticles from Salvia aethiopis L. and their antioxidant activity, Journal of Inorganic and Organometallic Polymers and Materials 31 (11) (2021) 4402-4409.
• N. Genc, Biosynthesis of silver nanoparticles using Origanum onites extract and investigation of their antioxidant activity, Particulate Science and Technology 39 (5) (2021) 562-568.
• N. Genc, I. Yildiz, R. Chaoui, R. Erenler, C. Temiz, M. Elmastas, Biosynthesis, characterization and antioxidant activity of oleuropein-mediated silver nanoparticles, Inorganic and Nano-Metal Chemistry 51 (3) (2021) 411-419.
• B. Dag, Green synthesis, characterization, and antioxidant activity of silver nanoparticles using Stachys annua L. subsp. annua var. annua, Particulate Science and Technology 40 (4) (2022) 512-520.
• R. Erenler, B. Dag, Biosynthesis of silver nanoparticles using Origanum majorana L. and evaluation of their antioxidant activity, Inorganic and Nano-Metal Chemistry 52 (4) (2022) 485-492.
• R. Erenler, E. N. Gecer, Green synthesis of silver nanoparticles from Astragalus logopodioides L. leaves, Turkish Journal of Agriculture-Food Science and Technology 10 (6) (2022) 1112-1115.
• R. Erenler, E. N. Gecer, Synthesis of Silver Nanoparticles Using Sideritis montana L. Leaf Extract: Characterization, catalytic degradation of methylene blue and antioxidant activity, Journal of Nano Research 75 (2022) 17-28.
• E. N. Gecer, R. Erenler, Biosynthesis of silver nanoparticles using Dittrichia graveolens (Asteraceae) leaves extract: Characterisation and assessment of their antioxidant activity, Turkish Journal of Biodiversity 5 (1) (2022) 50-56.
• E. N. Gecer, R. Erenler, Biosynthesis of silver nanoparticles using Echinacea pallida (Nutt.) Nutt. and antioxidant activity thereof, Journal of the Chemical Society of Pakistan 44 (6) (2022) 610-617.
• E. N. Gecer, R. Erenler, C. Temiz, N. Genc, I. Yildiz, Green synthesis of silver nanoparticles from Echinacea purpurea (L.) Moench with antioxidant profile, Particulate Science and Technology 40 (1) (2022) 50-57.
• T. Karan, R. Erenler, B. Bozer Moran, Synthesis and characterization of silver nanoparticles using curcumin: Cytotoxic, apoptotic, and necrotic effects on various cell lines, Zeitschrift für Naturforschung C 77 (7-8) (2022) 343-350.
• A. Sahin Yaglioglu, R. Erenler, E. N. Gecer, N. Genc, Biosynthesis of silver nanoparticles using astragalus flavesces leaf: Identification, antioxidant activity, and catalytic degradation of methylene blue, Journal of Inorganic and Organometallic Polymers and Materials 32 (2022) 3700-3707.
• R. Erenler, R. Chaoui, I. Yildiz, N. Genc, E. N. Gecer, C. Temiz, S. Akkal, Biosynthesis, characterisation, and antioxidant activity of silver nanoparticles using Schinus molle L, Trends in Sciences 20 (10) (2023) 6105-6105.
• R. Erenler, E. N. Gecer, I. Hosaflioglu, L. Behcet, Green synthesis of silver nanoparticles using Stachys spectabilis: Identification, catalytic degradation, and antioxidant activity, Biochemical and Biophysical Research Communications 659 (2023) 91-95.
• R. Erenler, I. Hosaflioglu, Green synthesis of silver nanoparticles using Onobrychis sativa L.: Characterization, catalytic degradation of methylene blue, antioxidant activity, and quantitative analysis of bioactive compounds, Materials Today Communications 35 (2023) 105863.
• R. Erenler, R. A. Ojelade, T. Karan, E. N. Gecer, N. Genc, C. Yaman, Facile, efficient synthesis of silver nanoparticles using Salvia absconditiflora: Assessment of their antioxidant capacity and catalytic activity, Inorganic Chemistry Communications 158 (2023) 111623.
• E. N. Gecer, Synthesis and characterization of silver nanoparticles using Origanum onites leaves: Cytotoxic, apoptotic, and necrotic effects on Capan-1, L929, and Caco-2 cell lines, Green Processing and Synthesis 12 (1) (2023) Article ID 20228126 8 pages.
• E. N. Gecer, R. Erenler, Biogenic synthesis of silver nanoparticles using Echium vulgare: Characterisation, quantitative analysis of bioactive compounds, antioxidant activity and catalytic degradation, Journal of the Indian Chemical Society 100 (5) (2023) Article ID 101003 8 pages.
• T. Karan, R. Erenler, Z. Gonulalan, U. Kolemen, Biogenic synthesis of silver nanoparticles using Sambucus nigra leaves: elucidation, antimicrobial, antioxidant activities and quantification of phenolics, Chemical Papers 78 (1) (2024) 473-481.
• T. Karan, Z. Gonulalan, R. Erenler, U. Kolemen, O. Eminagaoglu, Green synthesis of silver nanoparticles using Sambucus ebulus leaves extract: Characterization, quantitative analysis of bioactive molecules, antioxidant and antibacterial activities, Journal of Molecular Structure 1296 (2024) Article ID 136836 8 pages.
• Y. B. Karan, R. Erenler, Synthesis of silver nanoparticles using potato cultivars with their antioxidant activity, Communications in Soil Science and Plant Analysis 55 (9) (2024) 1249-1257.
• N. Nayel, S. Marah, T. Ozen, I. Yıldız, R. Erenler, L. Behcet, Characterization and comparative investigation of in vitro bioactivities for Lactuca Anatolica root aqueous extract and their green-chemical synthesized nanoparticles; Molecular Docking Studies, BioNanoScience (2024) https://doi.org/10.1007/s12668-024-01353-9
• A. Seçme, B. M. Bozer, A. Y. Kocaman, R. Erenler, M. H. Calimli, Synthesis, characterization, and anticancer properties of Ag nanoparticles derived from walnut leaves tested on cells of L929, MCF-7 and H1299, Journal of Drug Delivery Science and Technology 94 (2024) Article ID 105478 9 pages.
• C. Yaman, R. Erenler, M. N. Atalar, Ş. Adem, U. K. Çalişkan, Phytochemical properties, antioxidant and in vitro/in silico anti-acetylcholinesterase activities of hypericum heterophyllum leaf from Türkiye, Brazilian Archives of Biology and Technology 67 (2024) Article ID 24230043 14 pages.
• F. Z. Houari, M. Brahmi, R. Erenler, A. Hariri, Chemical profile, antibacterial and antioxidant properties of Rubia tinctorum L. essential oils, Natural Product Research (2024) 1-10.
• B. Bakchiche, G. Hadjira, R. Erenler, İ. Yildiz, A. S. Mohamed, M. A.m. El-shazly, Mineral contents, antioxidant and antimicrobial activities of algerian terfezia claveryi extracts, Fabad Journal of Pharmaceutical Sciences 49 (1) (2024) 19-36.
• M. Elmastas, S. M. Celik, N. Genc, H. Aksit, R. Erenler, İ. Gulcin, Antioxidant activity of an Anatolian herbal tea—Origanum minutiflorum: Isolation and characterization of its secondary metabolites, International Journal of Food Properties 21 (1) (2018) 374-384.
• Ö. Isildak, I. Yildiz, N. Genc, A new potentiometric PVC membrane sensor for the determination of DPPH radical scavenging activity of plant extracts, Food Chemistry 373 (2022) Article ID 131420 6 pages.
• Ö. Işıldak, İ. Yıldız, New potentiometric sensor for total phenolic assay of plant extracts, Bulletin of the Chemical Society of Japan 97 (5) (2024) Article ID uoae043 8 pages.
• Y. Başar, İ. Hosaflıoğlu, R. Erenler, Phytochemical analysis of Robinia pseudoacacia flowers and leaf: quantitative analysis of natural compounds and molecular docking application, Turkish Journal of Biodiversity 7 (1) (2024) 1-10.
• I. Demirtas, R. Erenler, M. Elmastas, A. Goktasoglu, Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction, Food Chemistry 136 (1) (2013) 34-40.
• W. Hassan, G. Rongyin, A. Daoud, L. Ding, L. Wang, J. Liu, J. Shang, Reduced oxidative stress contributes to the lipid-lowering effects of isoquercitrin in free fatty acids induced hepatocytes, Oxidative Medicine and Cellular Longevity 2014 (1) (2014) Article ID 313602 18 pages.
• X.-M. Peng, G. L. V. Damu, H. Zhou, Current developments of coumarin compounds in medicinal chemistry, Current Pharmaceutical Design 19 (21) (2013) 3884-3930.
• A. Ganeshpurkar, A. Saluja, The pharmacological potential of catechin, Indian Journal of Biochemistry and Biophysics (IJBB) 57 (5) (2020) 505-511.
• J. L. Boatwright, K. Pajerowska‐Mukhtar, Salicylic acid: An old hormone up to new tricks, Molecular Plant Pathology 14 (6) (2013) 623-634.