Phytochemical Compounds, Antioxidant Activity and HPLC Polyphenols Profiling of Echinops ritro L. ecotypes

Document Type : Research Paper

Authors

1 Department of Medicinal plant department, Shahid Bakeri Higher Education Center of Miandoab, Urmia University, Urmia, Iran

2 Department of Horticultural Sciences, Faculty of Agriculture, Urmia University, Urmia, Iran

Abstract

In this research, phytochemical compounds, antioxidant activity and polyphenolic compounds of 27 ecotypes of Echinops ritro were investigated. Total carotenoid and beta-carotene were evaluated as plant pigments. Total phenol, total flavonoid, antioxidant activity and total carbohydrate content were measured using Folin–Ciocalteu, aluminum chloride, anthrone and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) methods, respectively. Hierarchical cluster analysis (HCA) and Principal component analysis (PCA) were done among the traits using Minitab software. R software based on Pearson's method was used for correlation between data. The highest levels of total carotenoid content (16.17 μg/g FW) and beta-carotene (0.024 mg/g FW) were obtained in G19. The value of total phenol, total flavonoid, antioxidant activity and total carbohydrate content were ranged between 5.42-22.60 mg GAE/g FW, 1.56-4.21 mg QUE/g FW, 2.30-16.52 mg AA/g FW and 1.76-6.66 mg/g FW, respectively. p-coumaric acid (538.29 μg/g FW) were revealed as major phenolic compounds of Echinops ecotypes, being an order of magnitude higher than the others. Based on HCA and PCA, twenty-seven of Echinops ecotypes were divided into four main groups. Quantitative phenolic compounds were detected by high‐performance liquid chromatography. The findings showed that G19, G25, G12, G4, G15 and G4 of Echinops ecotypes can be considered as an excellent source of total carotenoid content and beta-carotene, total phenol content, total flavonoid content, antioxidant activity, total carbohydrate content and p-coumaric acid, respectively. Therefore, the information from this research can be useful for introducing valuable Echinops ecotypes for use in the food and pharmaceutical industries as well as breeding projects.

Keywords

Main Subjects


  1. Bouzabata A., Mahomoodally F., Tuberoso C. Ethnopharmacognosy of Echinops spinosus L. in North Africa: a mini review. Journal of Complementary and Alternative Medical Research. 2018; 8(1):40-52. https://doi.org/10.5455/jcmr.20180318051853.
  2. Sánchez-Jiménez I., Lazkov G.A., Hidalgo O., Garnatje T. Molecular systematics of Echinops L. (Asteraceae, Cynareae): A phylogeny based on ITS and trnL-trnF sequences with emphasis on sectional delimitation. Taxon. 2010; 59(3):698-708. https://doi.org/10.2307/25677662.
  3. Rechinger KH. Flora Iranica, Compositae III-Cynareae. Graz, Austria. 1979; 139:218-30.
  4. Montazerolghaem S., Rahiminejad M.R., Mozaffarian V., Susanna A. Taxonomic notes on the genus Echinops (Compositae, Cardueae–Echinopsinae) in Iran. Phytotaxa. 2016; 263(2):81. https://doi.org/10.11646/phytotaxa.263.2.1.
  5. Sharafzadeh S., Alizadeh O. Some medicinal plants cultivated in Iran. Journal of Applied Pharmaceutical Science. 2012; 30(Issue):134-7.
  6. Bitew H., Hymete A. The genus Echinops: Phytochemistry and biological activities: A review. Frontiers in Pharmacology. 2019; 10:1234. https://doi.org/10.3389/fphar.2019.01234.
  7. Asadi M., Hadinedoushan H., Mirghanizadeh S.A., Karimollah A., Dashti F., Malek-hosseini S. The effect of Echinops Lasiolepis extracts, native plant of Yazd province, on peripheral blood mononuclear cell proliferation and IFN-γ secretion. International Journal of Medical Laboratory. 2014; 1(1):7-14.
  8. Abdallah H.M., Ezzat S.M., El Dine R.S., Abdel-Sattar E., Abdel-Naim A.B. Protective effect of Echinops galalensis against CCl4-induced injury on the human hepatoma cell line (Huh7). Phytochemistry Letters. 2013; 6(1):73-8. https://doi.org/10.1016/j.phytol.2012.10.012.
  9. Kevin K., John K., Carolyn N., Derrick S., Lubega A. In vitro anti-tuberculosis activity of total crude extract of Echinops amplexicaulis against multi-drug resistant Mycobacterium tuberculosis. Journal of Health Sciences. 2018; 6:296-303. https://doi.org/10.17265/2328-7136/2018.04.008.
  10. Kiyekbayeva L., Mohamed N.M., Yerkebulan O., Mohamed E.I., Ubaidilla D., Nursulu A., Assem M., Srivedavyasasri R., Ross S.A. Phytochemical constituents and antioxidant activity of Echinops albicaulis. Natural Product Research. 2018; 32(10):1203-7. https://doi.org/10.1080/14786419.2017.1323213.
  11. Li L.B., Xiao G.D., Xiang W., Yang X., Cao K.X., Huang R.S. Novel substituted thiophenes and sulf-polyacetylene ester from Echinops ritro L. Molecules. 2019; 24(4):805. https://doi.org/10.3390/molecules24040805.
  12. Mohebat R., Bidoki M.Z. Comparative chemical analysis of volatile compounds of Echinops ilicifolius using hydrodistillation and headspace solid-phase microextraction and the antibacterial activities of its essential oil. Royal Society Open Science. 2018; 5(2):171424. https://doi.org/10.1098/rsos.171424.
  13. Karimov U.T., Aisa H.A. Phytochemical study of the plant Echinops integrifolius growing in the Altai (XUAR PRC). Chemistry of Natural Compounds. 2012; 48(5):903-5. https://doi.org/10.1007/s10600-012-0419-6.
  14. Mahmood A.A., Khadeem E.J. Phytochemical investigation of flavonoids glycoside in the Iraqi Echinops heterophyllus (Compositae). Pharmacie Globale. 2013; 4(9):1.
  15. Dong L.I., Ning L., Wan X.I., Peng Z.H., Zhong-jun M., Xian L. Chemical constituents of the root of echinops grijisii Hance. Shenyang Yao Ke Da Xue Xue Bao. 2008; 8(007).
  16. Lightenthaler H.K. Chlorophylls and carotenoids: pigments of photosynthetic biomembranes. Methods in Enzymology. 1987; 148:350-82. https://doi.org/10.1016/0076-6879(87)48036-1.
  17. Slinkard K., Singleton V.L. Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture. 1977; 28(1):49-55. https://doi.org/10.5344/ajev.1977.28.1.49.
  18. Silva M.C., Paiva S.R. Antioxidant activity and flavonoid content of Clusia fluminensis Planch. & Triana. Anais da Academia Brasileira de Ciências. 2012; 84:609-16. https://doi.org/10.1590/S0001-37652012000300004.
  19. Nakajima J.I., Tanaka I., Seo S., Yamazaki M., Saito K. LC/PDA/ESI‐MS profiling and radical scavenging activity of anthocyanins in various berries. Biomedicine Research International. 2004; 2004(5):241-7. https://doi.org/10.1155/S1110724304404045.
  20. Carroll N.V., Longley R.W., Roe J.H. The determination of glycogen in liver and muscle by use of anthrone reagent. Journal of Biological Chemistry. 1956; 220(2):583-93. https://doi.org/10.1016/S0021-9258(18)65284-6.
  21. Gholizadeh‐Moghadam N., Hosseini B., Alirezalu A. Classification of barberry genotypes by multivariate analysis of biochemical constituents and HPLC profiles. Phytochemical Analysis. 2019; 30(4):385-94. https://doi.org/10.1002/pca.2821.
  22. Bogacz-Radomska L., Harasym J. β-Carotene—properties and production methods. Food Quality and Safety. 2018; 2(2):69-74. https://doi.org/10.1093/fqsafe/fyy004.
  23. Bakan E., Akbulut Z.T., İnanç A.L. Carotenoids in foods and their effects on human health. Akademik Gıda. 2014; 12(2):61-8.
  24. Khoo H.E., Prasad K.N., Kong K.W., Jiang Y., Ismail A. Carotenoids and their isomers: color pigments in fruits and vegetables. Molecules. 2011; 16(2):1710-38. https://doi.org/10.3390/molecules16021710.
  25. González-Peña M.A., Ortega-Regules A.E., Anaya de Parrodi C., Lozada-Ramírez J.D. Chemistry, occurrence, properties, applications, and encapsulation of carotenoids—A review. Plants. 2023; 12(2):313. https://doi.org/10.3390/plants12020313.
  26. Fiedor J., Burda K. Potential role of carotenoids as antioxidants in human health and disease. Nutrients. 2014; 6(2):466-88. https://doi.org/10.3390/nu6020466.
  27. Al-Assaf I., Khazem M. Antioxidant Activity of Total phenols and Flavonoids extracted from Echinops polyceras roots grown in Syria. Iraqi Journal of Pharmaceutical Sciences. 2021; 30(2):261-8. https://doi.org/10.31351/vol30iss2pp261-268.
  28. Bhattacharya A., Sood P., Citovsky V. The roles of plant phenolics in defence and communication during Agrobacterium and Rhizobium infection. Molecular Plant Pathology. 2010; 11(5):705-19. https://doi.org/10.1111/j.1364-3703.2010.00625.x.
  29. Hassanpour S.H., Doroudi A. Review of the antioxidant potential of flavonoids as a subgroup of polyphenols and partial substitute for synthetic antioxidants. Avicenna Journal of Phytomedicine. 2023; 13(4):354. https://doi.org/10.22038/AJP.2023.21774.
  30. Şapcı H., Vural C., Özcan S. Antimicrobial and Antioxidant activity of Echinops emiliae (Asteraceae). International Journal of Secondary Metabolite. 2017; 4(3):400-5. https://doi.org/10.21448/ijsm.375102.
  31. Zitouni-Nourine S.H., Belyagoubi-Benhammou N., El-Houaria Zitouni-Haouar F., Douahi O., Chenafi F., Fetati H., Chabane Sari S., Benmahieddine A., Zaoui C., Mekaouche F.Z., Atik Bekkara F. Echinops spinosissimus turra root methanolic extract: Characterization of the bioactive components and relative wound healing, antimicrobial and antioxidant properties. Plants. 2022; 11(24):3440. https://doi.org/10.3390/plants11243440.
  32. Aydın Ç., Özcan G.T., Turan M., Mammadov R. Phenolic contents and antioxidant properties of Echinops ritro L. and E. tournefortii Jaup. Et. Spach extract. International Journal of Secondary Metabolite. 2016; 3(2):74-81. https://doi.org/10.21448/http-ijate-net-index-php-ijsm.243309.
  33. Shameh S., Alirezalu A., Hosseini B., Maleki R. Fruit phytochemical composition and color parameters of 21 accessions of five Rosa species grown in North West Iran. Journal of the Science of Food and Agriculture. 2019; 99(13):5740-51. https://doi.org/10.1002/jsfa.9842. Epub 2019 Jul 16.
  34. Kumar S., Pandey A.K. Chemistry and biological activities of flavonoids: an overview. The Scientific World Journal. 2013; 2013(1):162750. https://doi.org/10.1155/2013/162750.
  35. Heim K.E., Tagliaferro A.R., Bobilya D.J. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. The Journal of Nutritional Biochemistry. 2002; 13(10):572-84. https://doi.org/10.1016/s0955-2863(02)00208-5.
  36. Falcone Ferreyra M.L., Rius S.P., Casati P. Flavonoids: biosynthesis, biological functions, and biotechnological applications. Frontiers in Plant Science. 2012; 3:222. https://doi.org/10.3389/fpls.2012.00222/
  37. Sytar O., Hemmerich I., Zivcak M., Rauh C., Brestic M. Comparative analysis of bioactive phenolic compounds composition from 26 medicinal plants. Saudi Journal of Biological Sciences. 2018; 25(4):631-41. https://doi.org/10.1016/j.sjbs.2016.01.036.
  38. Al-Harbi K.B., El-Tigani-Asil E.A., Ahmed A.F, El-Ashmawy I.M., Al-Wabel N.A. Wound healing potential of methanolic extracts of some plants native to Al-Qassim Region, Saudi Arabia. Journal of Food, Agriculture and Environment. 2016; 14:3-4.
  39. Samir H., Abbas M.S., Soliman A.S., Lotfy R.A. Phytochemical screening, antioxidant and cytotoxic activities of some plants species derived from the northwestern coast of Egypt. Research Journal of Pharmaceutical, Biological and Chemical Sciences. 2018; 9(6):82-94.
  40. Sampaio B.L., Bara M.T., Ferri P.H., Santos S.D., Paula J.R. Influence of environmental factors on the concentration of phenolic compounds in leaves of Lafoensia pacari. Revista Brasileira de Farmacognosia. 2011; 21:1127-37. https://doi.org/10.1590/S0102-695X2011005000177.
  41. Salazar R., Pozos M.E., Cordero P., Perez J., Salinas M.C., Waksman N. Determination of the antioxidant activity of plants from Northeast Mexico. Pharmaceutical Biology. 2008; 46(3):166-70. https://doi.org/10.1080/13880200701498952.
  42. Kedare S.B., Singh R.P. Genesis and development of DPPH method of antioxidant assay. Journal of Food Science and Technology. 2011; 48(4):412-22. https://doi.org/10.1007/s13197-011-0251-1.
  43. Şapcı H., Vural C. Bioactivity researching on New Species of Echinops L. Asteraceae): Antimicrobial and Antioxidant Activity of Antalyensis. Anadolu University Journal of Science and Technology C-Life Sciences and Biotechnology. 2018; 7(1):68-73. https://doi.org/10.18036/aubtdc.333248.
  44. Al Masoudi L.M., Hashim A.M. Morphological Features and Biological Activity of Different Extracts of Echinops spinosissimus Grown in Saudi Arabia. Agronomy. 2023; 13(2):573. https://doi.org/10.3390/agronomy13020573.
  45. Mohseni S., Sani A.M., Tavakoli M., Raoufi AM. Effect of extraction conditions on antioxidant activities of Echinops persicus. Journal of Essential Oil Bearing Plants. 2017; 20(6):1633-44. https://doi.org/10.1080/0972060X.2017.1399088.
  46. Deore Sonali V., Kadam Vasant B. Estimation of total carbohydrates content in different parts of Trigonella foenum-graecum Linn. Natural Medicine. 2016; 4: 72-75.
  47. Tharanathan R.N., Muralikrishna G., Salimath P.V., Rao M.R. Plant carbohydrates—an overview. Proceedings of Indian Academy of Sciences. 1987; 97(2):81-155. New Delhi: Springer India. https://doi.org/10.1007/BF03053322.
  48. Trouvelot S., M.C., Héloir B., Poinssot A., Gauthier F., Paris, C., Guillier, M., Combier, L., Trdá X., Daire M., Adrian. Carbohydrates in plant immunity and plant protection: roles and potential application as foliar sprays. Frontiers in Plant Science. 4 (2014) 592. https://doi.org/10.3389/fpls.2014.00592.
  49. Ibrahim H., Moaty A. Chemical Constituents of Echinops Spinosissimus Turra, International Journal of Advanced Research. 2016; 4:1129-36. https://doi.org/10.21474/IJAR01/1178.
  50. Qaderi M.M., Martel A.B., Strugnell C.A. Environmental factors regulate plant secondary metabolites. Plants. 2023; 12(3):447. https://doi.org/10.3390/plants12030447.
  51. Li Y., Kong D, Fu Y., Sussman M.R., Wu H. The effect of developmental and environmental factors on secondary metabolites in medicinal plants. Plant Physiology and Biochemistry. 2020; 148:80-9. https://doi.org/10.1016/j.plaphy.2020.01.006.
  52. Zhang Y., Cai P., Cheng G., Zhang Y.A. brief review of phenolic compounds identified from plants: Their extraction, analysis, and biological activity. Natural Product Communications. 2022; 17(1):1934578X211069721.https://doi.org/10.1177/1934578X211069721.
  53. Kumar S., Abedin M.M., Singh A.K., Das S. Role of phenolic compounds in plant-defensive mechanisms. InPlant phenolics in sustainable agriculture. 1:517-532. Singapore: Springer Singapore. https://doi.org/10.1007/978-981-15-4890-1_22.
  54. Dessalegn E., Rupasinghe H.V. Quantification of phenolic compounds by HPLC-DAD and in vitro antioxidant activity of root extract of Echinops kebericho Mesfin (Asteraceae). Chemical and Process Engineering Research. 2020; 31(62):6-13. https://doi.org/10.7176/CPER/62-02.
  55. Khedher O., Rigane G., Riguene H., Ben Salem R., Moussaoui Y. Phenolic profile (HPLC-UV) analysis and biological activities of two organic extracts from Echinops spinosissimus Turra roots growing in Tunisia. Natural Product Research. 2021; 35(24):5786-93. https://doi.org/10.1080/14786419.2020.1837812.
  56. Pourhosseini S.H., Mirjalili M.H., Ghasemi M., Ahadi H., Esmaeili H., Ghorbanpour M. Diversity of phytochemical components and biological activities in Zataria multiflora Boiss. (Lamiaceae) populations. South African Journal of Botany. 2020; 135:148-57. https://doi.org/10.1016/j.sajb.2020.08.024.
  57. Ghorbani N., Chamani E., Shokoohian A.A., Ramezanpour S.S. Biochemical diversity of yellow flag (Iris pseudacorus L.) at various geographical locations. International Journal of Horticultural Science and Technology. 2023; 10(4):421-32. https://doi.org/10.22059/ijhst.2022.346841.580.
  58. Sfidari E., Kadkhodaie-Ilkhchi A., Najjari S. Comparison of intelligent and statistical clustering approaches to predicting total organic carbon using intelligent systems. Journal of Petroleum Science and Engineering. 2012; 86:190-205. https://doi.org/10.1016/j.petrol.2012.03.024.
  59. Huang J., Ding L., Tian W., Zhi H., Chen J., Wu L., Wang L., Xie J., Bai J., Fan H., Zhao S. Polyphaenolic profiling, antioxidant properties, and inhibition of α-glucosidase of Mesona chinensis benth from Southern China. Microchemical Journal. 2021; 168:106399. https://doi.org/10.1016/j.microc.2021.106399.
  60. Jolliffe I.T., Cadima J. Principal component analysis: a review and recent developments. Philosophical transactions of the royal society A: Mathematical, Physical and Engineering Sciences. 2016; 374(2065):20150202. https://doi.org/10.1098/rsta.2015.0202.
  61. Kumar S., Sandhir R., Ojha S. Evaluation of antioxidant activity and total phenol in different varieties of Lantana camara leaves. BMC Research Notes. 2014;7(1):560. https://doi.org/10.1186/1756-0500-7-560.
  62. Pandey B., Rajbhandari M. Estimation of total phenolic and flavonoid contents in some medicinal plants and their antioxidant activities. Nepal Journal of Science and Technology. 2014; 15(1):53-60.
  63. Mello L.D., Quadros GP. Correlation between antioxidant activity and total phenolic content with physicochemical parameters of blended extracts of Camellia sinensis. Acta Scientiarum. Health Sciences. 2014;36(1):97-103. https://doi.org/10.4025/actascihealthsci.v36i1.12615.
  64. Osman M.A., Mahmoud G.I., Shoman S.S. Correlation between total phenols content, antioxidant power and cytotoxicity. Biointerface Res. Appl. Chem. 2020; 11(3):10640-53. https://doi.org/10.33263/BRIAC113.1064010653.
  65. Modareskia M., Fattahi M., Mirjalili M.H. Thymol screening, phenolic contents, antioxidant and antibacterial activities of Iranian populations of Trachyspermum ammi (L.) Sprague (Apiaceae). Scientific Reports. 2022;12(1):15645. https://doi.org/10.1038/s41598-022-19594-7.
  66. Vafaeian A., Fathi S., Jaberian H., Nazarideljou M.J. Comparing the characteristics of lemongrass plant in different harvesting time under soil and soilless cultivation systems. Journal of Medicinal plants and By-products. 2025; 14(1):20-9. https://doi.org/10.22034/jmpb.2024.365417.1676.
  67. Kazeminia M., Mehrabi A., Mahmoudi R. Chemical composition, biological activities, and nutritional application of Asteraceae family herbs: A systematic review. Trends in Phytochemical Research. 2022;6(3): 187-213. https://doi.org/10.30495/tpr.2022.1954612.1248.