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Phytochemical profile of Agrimonia eupatoria L. from Bulgaria and effects of its extracts on Galleria mellonella (L.) (lepidoptera: pyralidae) larvae
Corresponding Author(s) : Hafize Fidan
Carpathian Journal of Food Science and Technology,
Vol. 15 No. 3 (2023): Carpathian Journal of Food Science and Technology
Abstract
Plants contain polyphenolic compounds such as phenolic acids, flavonoids, stilbenes, lignans, essential oils, etc., which are endowed with antioxidant properties. This study aimed to correlate the total phenolic compound and flavonoid content of Agrimonia eupatoria L. with its antioxidant properties and to determine some mineral elements (Na, K, Ca, Mg, P). The antioxidant capacity of the extract was tested by three methods (DPPH, FRAP, and TEAC). According to the results, the antioxidant content of A. eupatoria was found to be high (IC50=38.03±0.01μg/mL). Total phenolic and flavonoid contents were found as 13.66±0.38 mg GAE/g and 4.65±0.01mg QE/g, respectively. Besides, the major components found in A. eupatoria were α-pinene (62.72%), n-hexadecanoic acid (11.41%), (5E,9E)-farnesyl acetone (6.64%), and (5E,9Z)-farnesyl acetone (3.65%). Heavy metal content in A. eupatoria was found within WHO limits. It was also investigated whether A. eupatoria has toxic effects. Because a medicinal plant is not supposed to harm metabolism, for this investigation, larvae stage of Galleria mellonella had selected as a test organism. In order to investigate the toxic effects, oxidative stress parameters (SOD, CAT, GST, GPx, MDA) and AChE activity were measured. And no harmful effects were observed at the doses administered at 24, 48, and 72 h.
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- Adams, R.P. (2007). Identification of essential oil components by gas chromatography/mass spectrometry. Vol. 456. Carol Stream: Allured publishing corporation.
- Aebi, H. (1984). Catalase in vitro. Methods in Enzymology, 105, 121-126.
- AOAC. Method 930.05. Ash of plants. Official Methods of Analysis (Horwitz, W. & Latimer Jr., G.W., Eds.). Gaithersburg, MD, USA: AOAC International. 2005.
- AOAC. Method 976.06. Protein (crude) in animal feed and pet food. Official Methods of Analysis (Latimer Jr., G.W., Ed.). Geithersburg, MD, USA: AOAC International. 2016.
- Apaydin, F.G., Kalender, S., Bas, H., Demir, F., Kalender, Y. (2014). Lead nitrate induced testicular toxicity in diabetic and nondiabetic rats: protective role of sodium selenite. Brazilian Archives of Biology and Technology, 58, 68-74.
- Arsene, M.M.J., Viktorovna, P.I., Davares, A.K.L. (2021). Galleria mellonella (greater wax moth) as an eco-friendly in vivo approach for the assessment of the acute toxicity of medicinal plants: Application to some plants from Cameroon. Open Veterinary Journal. 11(4), 651.
- Balinova, A., Diakov, G. (1974). On improved apparatus for microdistillation of rose flowers. Plant Science. 11, 77-85.
- Bas, H., Kalender, S., Pandir, D. (2014). In vitro effects of quercetin on oxidative stress mediated in human erythrocytes by benzoic acid and citric acid. Folia Biologica (Kraków), 62(1), 57-64.
- Bas, H., Pandır, D. (2016). Protective effects of lycopene on furan-treated diabetic and nondiabetic rat lung. Biomedical and Environmental Sciences, 29(2), 143-147.
- Benzie, F.F., Strain, J.J. (1999). Ferric Reducing/ Antioxidant Power Assay: Direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods in Enzymology, 299, 15-23.
- Brendel, O., Iannetta, P. P. M., Stewart, D. (2000). A rapid and simple method to isolate pure α-cellulose. Phytochemical Analysis. 11(1), 7-10.
- Ciobanu, N., Cojocaru-Toma, M., Ciobanu, C., Benea, A. (2018). Evaluation of polyphenolic profile and antioxidant activity of some species cultivated in the Republic of Moldova. Eurasian Journal of Analytical Chemistry, 13(3), 441-447.
- Ciobanu, N., Cojocaru-Toma, M., Ciobanu, C., Benea, A. (2018). Evaluation of polyphenolic profile and antioxidant activity of some species cultivated in the Republic of Moldova. Eurasian Journal of Analytical Chemistry, 13(3), 441-447.
- Côrte-Real, N., Oliveira, T., Ruivo, P. (2017). Assessing business value of big data analytics in European firms. Journal of Business Research. 70, 379-390.
- Doğan, H. (2020). Minerals and bioactive content of some Salvia species in cultivated condition. Comptes Rendus de L Academie Bulgare des Sciences, 73(10).
- Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M. (1961). A New and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88-95.
- Feng, X., He, Y., Liang, Y., Wang, Y., Huang, L., Xie, J. (2013). Comparative analysis of the volatile components of Agrimonia eupatoria from leaves and roots by Gas Chromatography-Mass Spectrometry and Multivariate Curve Resolution. Journal of Analytical Methods in Chemistry. Article ID 246986.
- Gezer, K., Duru, M.E., Kıvrak, I., Türkoğlu, A., Mercan, N., Türkoğlu, H., Gülcan, S. (2006). Free-radical Scavenging capacity and antimicrobial activity of wild edible mushroom of Turkey, African Journal of Biyotechnology, 5 (20):1924-1928.
- Gutteridge, J.M., Halliwell, B. (2010). Antioxidants: molecules, medicines, and myths. Biochemical and Biophysical Research Communications, 393(4), 561-564.
- Habig, W.H., Pabst, M.J., Jakoby, W.B. (1974). Glutathione-S-Transferases: The First enzymatic step in mercapturic acid formation, The Journal of Biological Chemistry, 249, 7130-7139.
- Hazarika, A., Sarkar, S.N., Kataria, M., Malik, J.K. (2003). Influence of malathion pretreatment on the toxicity of anilofos in male rats: A Biochemical Interaction Study. Toxicology, 185, 1-8.
- Jin, Z.X., Wang, B.Q., Chen, Z.J. (2010). Microwave-assisted extraction of tannins from Chinese herb Agrimonia pilosa Ledeb. Journal of Medicinal Plants Research, 4(21), 2229-2234.
- Kaçar, B., İnal, A. (2010). Plant Analysis. Ankara, Turkey: Nobel Yayıncılık.
- Kara, Ö., Baş, H., Pandır, D. (2016). Furan toxicity on testes and protective role of lycopene in diabetic rats. Journal of the Turkish German Gynecological Association, 17(4), 191.
- Kozykeyeva, R.A., Datkhayev, U.M., Srivedavyasasri, R., Ajayi, T. O., Patsayev, A. K., Kozykeyeva, R. A., Ross, S. A. (2020). Isolation of chemical compounds and essential oil from Agrimonia asiatica Juz. and their antimicrobial and antiplasmodial activities. The Scientific World Journal. Article ID 7821310.
- Kozykeyeva, R.A., Datkhayev, U.M., Srivedavyasasri, R., Ajayi, T. O., Patsayev, A. K., Kozykeyeva, R.A., Ross, S.A. (2020). Isolation of chemical compounds and essential oil from Agrimonia asiatica Juz. and their antimicrobial and antiplasmodial activities. The Scientific World Journal. Article ID 7821310,
- Lee, K.Y., Hwang, L., Jeong, E. J., Kim, S.H., Kim, Y.C., Sung, S.H. (2010). Effect of neuroprotective flavonoids of Agrimonia eupatoriaon glutamate-induced oxidative injury to HT22 hippocampal cells. Bioscience, Biotechnology, and Biochemistry, 74 (8), 1704-1706.
- Marklund, S., Marklund, G. (1974). Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. European Journal of Biochemistry, 47, 469-474.
- McCord, J.M., Fridovich, I. (1999). Superoxide dismutase: an enzymic function for erythrocuprein (hemocuprein), Journal of Biological Chemistry, 244, 6049-6055.
- Melkani, A.B., Negi, A., Javed, M.S., Beauchamp, P.S., Dev,V. (2007). Agrimonia aitchisoni Schonbeck Temesy (Rosaceae): A new source of methyl myrtenate. Journal of Essential Oil Research, 19(3), 273-275.
- Muruzović, M. Ž., Mladenović, K. G., Stefanović, O. D., Vasić, S. M., Čomić, L. R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis, 24(3), 539-547.
- Muruzović, M.Ž., Mladenović, K.G., Stefanović, O.D., Vasić, S. M., Čomić, L.R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis, 24(3), 539-547.
- Muruzovic, M.Z., Mladenovic, K.G., Stefanovic, O.D., Vasic, S.M., Comic L.R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis. 24, 539-547.
- Navaei, M., Mirza, M. (2009). A comparative study of the essential oils of Agrimonia eupatoria Both cultivated and wild growing conditions in Iran. Journal of Essential OilBearing Plants. 12(3), 369-373.
- Norhasidah, S., Engku Hanisah, E. U., Farahniza, Z., Maaruf, A. G., Abdul Salam, B. (2014). Antioxidative properties of edible bird’s nest mincroparticulates incorporated into red dates drink. In Edible Bird Nest Industry Conference, Putrajaya, Malaysia.
- Ohkawa, H., Ohishi, N., Yagi, K. (1979). Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction, Analytical Biochemistry, 95, 351-358.
- Paglia, D.E., Valentine, W.N. (1987). Studies on The quantative and qualitative characterization of glutathione peroxidase. Journal of Laboratory Medicine, 70, 158-165.
- Pamukov, A. (1989). Prirodna apteka, Zemizdat. Sofia.
- Petrova, A., Ancheva, M., Palamarev E. (1999). How to recognize plants in our nature, excursion guide, Prosveta (in Bulgarian).
- Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237.
- Sekretar, S., Schmidt, S., Vajdak, M., Zahradnikova, L., Annus, J. (2004). Antioxidative and antimicrobial effects of some natural extracts in lard. Czech Journal of Food Sciences, 22(I), 215.
- Şenkal, B.C., Uskutoğlu, T., Cesur, C., Özavci, V., Doğan, H. (2019). Determination of essential oil components, mineral matter, and heavy metal content of Salvia virgata Jacq. grown in culture conditions. Turkish Journal of Agriculture and Forestry, 43(4), 395-404.
- Singleton, V.L., Orthofer, R., LamuelaRaventos, R.M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods in Enzymology. 299, 152-178.
- Tomlinson, C. T., Nahar, L., Copland, A., Kumarasamy, Y., Mir-Babayev, N. F., Middleton, M., Raid, G.R., Sarker, S. D. (2003). Flavonol glycosides from the seeds of Agrimonia eupatoria (Rosaceae). Biochemical Systematics and Ecology, 31(4), 439-441.
- Venskutonis, P.R., Skemaite, M., Ragazinskiene, O. (2007). Radical scavenging capacity of Agrimonia eupatoria and Agrimonia procera. Fitoterapia, 78(2), 166-168.
- Wang, H., Liu Y.Q., Wei, S.L., Yan, Z.J., Jin, X. (2012). Comparative chemical composition of the essential oils obtained by microwave assisted hydrodistillation and hydrodistillation from Agrimonia pilosa Ledeb. collected in three different regions of China. Chemistry and Biodiversity, 9(3),662-668.
References
Adams, R.P. (2007). Identification of essential oil components by gas chromatography/mass spectrometry. Vol. 456. Carol Stream: Allured publishing corporation.
Aebi, H. (1984). Catalase in vitro. Methods in Enzymology, 105, 121-126.
AOAC. Method 930.05. Ash of plants. Official Methods of Analysis (Horwitz, W. & Latimer Jr., G.W., Eds.). Gaithersburg, MD, USA: AOAC International. 2005.
AOAC. Method 976.06. Protein (crude) in animal feed and pet food. Official Methods of Analysis (Latimer Jr., G.W., Ed.). Geithersburg, MD, USA: AOAC International. 2016.
Apaydin, F.G., Kalender, S., Bas, H., Demir, F., Kalender, Y. (2014). Lead nitrate induced testicular toxicity in diabetic and nondiabetic rats: protective role of sodium selenite. Brazilian Archives of Biology and Technology, 58, 68-74.
Arsene, M.M.J., Viktorovna, P.I., Davares, A.K.L. (2021). Galleria mellonella (greater wax moth) as an eco-friendly in vivo approach for the assessment of the acute toxicity of medicinal plants: Application to some plants from Cameroon. Open Veterinary Journal. 11(4), 651.
Balinova, A., Diakov, G. (1974). On improved apparatus for microdistillation of rose flowers. Plant Science. 11, 77-85.
Bas, H., Kalender, S., Pandir, D. (2014). In vitro effects of quercetin on oxidative stress mediated in human erythrocytes by benzoic acid and citric acid. Folia Biologica (Kraków), 62(1), 57-64.
Bas, H., Pandır, D. (2016). Protective effects of lycopene on furan-treated diabetic and nondiabetic rat lung. Biomedical and Environmental Sciences, 29(2), 143-147.
Benzie, F.F., Strain, J.J. (1999). Ferric Reducing/ Antioxidant Power Assay: Direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods in Enzymology, 299, 15-23.
Brendel, O., Iannetta, P. P. M., Stewart, D. (2000). A rapid and simple method to isolate pure α-cellulose. Phytochemical Analysis. 11(1), 7-10.
Ciobanu, N., Cojocaru-Toma, M., Ciobanu, C., Benea, A. (2018). Evaluation of polyphenolic profile and antioxidant activity of some species cultivated in the Republic of Moldova. Eurasian Journal of Analytical Chemistry, 13(3), 441-447.
Ciobanu, N., Cojocaru-Toma, M., Ciobanu, C., Benea, A. (2018). Evaluation of polyphenolic profile and antioxidant activity of some species cultivated in the Republic of Moldova. Eurasian Journal of Analytical Chemistry, 13(3), 441-447.
Côrte-Real, N., Oliveira, T., Ruivo, P. (2017). Assessing business value of big data analytics in European firms. Journal of Business Research. 70, 379-390.
Doğan, H. (2020). Minerals and bioactive content of some Salvia species in cultivated condition. Comptes Rendus de L Academie Bulgare des Sciences, 73(10).
Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M. (1961). A New and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88-95.
Feng, X., He, Y., Liang, Y., Wang, Y., Huang, L., Xie, J. (2013). Comparative analysis of the volatile components of Agrimonia eupatoria from leaves and roots by Gas Chromatography-Mass Spectrometry and Multivariate Curve Resolution. Journal of Analytical Methods in Chemistry. Article ID 246986.
Gezer, K., Duru, M.E., Kıvrak, I., Türkoğlu, A., Mercan, N., Türkoğlu, H., Gülcan, S. (2006). Free-radical Scavenging capacity and antimicrobial activity of wild edible mushroom of Turkey, African Journal of Biyotechnology, 5 (20):1924-1928.
Gutteridge, J.M., Halliwell, B. (2010). Antioxidants: molecules, medicines, and myths. Biochemical and Biophysical Research Communications, 393(4), 561-564.
Habig, W.H., Pabst, M.J., Jakoby, W.B. (1974). Glutathione-S-Transferases: The First enzymatic step in mercapturic acid formation, The Journal of Biological Chemistry, 249, 7130-7139.
Hazarika, A., Sarkar, S.N., Kataria, M., Malik, J.K. (2003). Influence of malathion pretreatment on the toxicity of anilofos in male rats: A Biochemical Interaction Study. Toxicology, 185, 1-8.
Jin, Z.X., Wang, B.Q., Chen, Z.J. (2010). Microwave-assisted extraction of tannins from Chinese herb Agrimonia pilosa Ledeb. Journal of Medicinal Plants Research, 4(21), 2229-2234.
Kaçar, B., İnal, A. (2010). Plant Analysis. Ankara, Turkey: Nobel Yayıncılık.
Kara, Ö., Baş, H., Pandır, D. (2016). Furan toxicity on testes and protective role of lycopene in diabetic rats. Journal of the Turkish German Gynecological Association, 17(4), 191.
Kozykeyeva, R.A., Datkhayev, U.M., Srivedavyasasri, R., Ajayi, T. O., Patsayev, A. K., Kozykeyeva, R. A., Ross, S. A. (2020). Isolation of chemical compounds and essential oil from Agrimonia asiatica Juz. and their antimicrobial and antiplasmodial activities. The Scientific World Journal. Article ID 7821310.
Kozykeyeva, R.A., Datkhayev, U.M., Srivedavyasasri, R., Ajayi, T. O., Patsayev, A. K., Kozykeyeva, R.A., Ross, S.A. (2020). Isolation of chemical compounds and essential oil from Agrimonia asiatica Juz. and their antimicrobial and antiplasmodial activities. The Scientific World Journal. Article ID 7821310,
Lee, K.Y., Hwang, L., Jeong, E. J., Kim, S.H., Kim, Y.C., Sung, S.H. (2010). Effect of neuroprotective flavonoids of Agrimonia eupatoriaon glutamate-induced oxidative injury to HT22 hippocampal cells. Bioscience, Biotechnology, and Biochemistry, 74 (8), 1704-1706.
Marklund, S., Marklund, G. (1974). Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. European Journal of Biochemistry, 47, 469-474.
McCord, J.M., Fridovich, I. (1999). Superoxide dismutase: an enzymic function for erythrocuprein (hemocuprein), Journal of Biological Chemistry, 244, 6049-6055.
Melkani, A.B., Negi, A., Javed, M.S., Beauchamp, P.S., Dev,V. (2007). Agrimonia aitchisoni Schonbeck Temesy (Rosaceae): A new source of methyl myrtenate. Journal of Essential Oil Research, 19(3), 273-275.
Muruzović, M. Ž., Mladenović, K. G., Stefanović, O. D., Vasić, S. M., Čomić, L. R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis, 24(3), 539-547.
Muruzović, M.Ž., Mladenović, K.G., Stefanović, O.D., Vasić, S. M., Čomić, L.R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis, 24(3), 539-547.
Muruzovic, M.Z., Mladenovic, K.G., Stefanovic, O.D., Vasic, S.M., Comic L.R. (2016). Extracts of Agrimonia eupatoria L. as sources of biologically active compounds and evaluation of their antioxidant, antimicrobial, and antibiofilm activities. Journal of Food and Drug Analysis. 24, 539-547.
Navaei, M., Mirza, M. (2009). A comparative study of the essential oils of Agrimonia eupatoria Both cultivated and wild growing conditions in Iran. Journal of Essential OilBearing Plants. 12(3), 369-373.
Norhasidah, S., Engku Hanisah, E. U., Farahniza, Z., Maaruf, A. G., Abdul Salam, B. (2014). Antioxidative properties of edible bird’s nest mincroparticulates incorporated into red dates drink. In Edible Bird Nest Industry Conference, Putrajaya, Malaysia.
Ohkawa, H., Ohishi, N., Yagi, K. (1979). Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction, Analytical Biochemistry, 95, 351-358.
Paglia, D.E., Valentine, W.N. (1987). Studies on The quantative and qualitative characterization of glutathione peroxidase. Journal of Laboratory Medicine, 70, 158-165.
Pamukov, A. (1989). Prirodna apteka, Zemizdat. Sofia.
Petrova, A., Ancheva, M., Palamarev E. (1999). How to recognize plants in our nature, excursion guide, Prosveta (in Bulgarian).
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237.
Sekretar, S., Schmidt, S., Vajdak, M., Zahradnikova, L., Annus, J. (2004). Antioxidative and antimicrobial effects of some natural extracts in lard. Czech Journal of Food Sciences, 22(I), 215.
Şenkal, B.C., Uskutoğlu, T., Cesur, C., Özavci, V., Doğan, H. (2019). Determination of essential oil components, mineral matter, and heavy metal content of Salvia virgata Jacq. grown in culture conditions. Turkish Journal of Agriculture and Forestry, 43(4), 395-404.
Singleton, V.L., Orthofer, R., LamuelaRaventos, R.M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods in Enzymology. 299, 152-178.
Tomlinson, C. T., Nahar, L., Copland, A., Kumarasamy, Y., Mir-Babayev, N. F., Middleton, M., Raid, G.R., Sarker, S. D. (2003). Flavonol glycosides from the seeds of Agrimonia eupatoria (Rosaceae). Biochemical Systematics and Ecology, 31(4), 439-441.
Venskutonis, P.R., Skemaite, M., Ragazinskiene, O. (2007). Radical scavenging capacity of Agrimonia eupatoria and Agrimonia procera. Fitoterapia, 78(2), 166-168.
Wang, H., Liu Y.Q., Wei, S.L., Yan, Z.J., Jin, X. (2012). Comparative chemical composition of the essential oils obtained by microwave assisted hydrodistillation and hydrodistillation from Agrimonia pilosa Ledeb. collected in three different regions of China. Chemistry and Biodiversity, 9(3),662-668.