THE RELATIONSHIP BETWEEN MAIN POLYPHENOL COMPONENTS AND FREE RADICAL SCAVENGING ACTIVITY OF SELECTED MEDICINAL PLANTS
Abstract
This study investigates the relationships between the main polyphenols and DPPH radical scavenging activity (RSA) in extracts from some of the most common wild and cultivated species from the Achillea millefolium group, Mentha, Chenopodium botrys, Clinopodium vulgare and Artemisia vulgaris. Another aspect of the study is the effects of choosing an extraction solvent, highlighting the importance of selecting an appropriate one for obtaining extracts with maximum manifested bioactivity. Chemical characterization of compounds is performed. It is based on HPLC-PDA fingerprint profiles, obtained from 70% aqueous methanol extracts. Hydroxycinnamic acids, glycosides of luteolin (LG), apigenin (AG), their aglycones and methoxyflavones are found to be the most abundant components, which have the highest impact on radical scavenging activity (RSA) of the extracts. The data allow supposing high correlation relationships between caffeoylquinic acids and RSA of extracts from four A. millefolium group species and cv. Proa. Cl. vulgare methanol extract, rich in rosmarinic acid, LG and AG, showed the highest RSA with IC50 10.37μg.mL-1. In contrast, extracts of Ch. botrys which lack phenolic acids, contain low amount of glycosides and are rich in methoxyflavone aglycones, possess very weak RSA. For multicomponent analysis, our data suggest 70% methanol as the most appropriate solvent for extraction of compounds belonging to the polyphenol complex. Based on the high quantities of rosmarinic acid, luteolin and apigenin glycosides, 66% ethanol solvent is found to be the best choice for medicinal consumption extracts.
Keywords:
Polyphenols, HPLC-PDA, extraction, radical scavenging activityDOI
https://doi.org/10.25004/IJPSDR.2018.100305References
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31. Piluzza G, Bullitta S. Correlations between phenolic content and antioxidant properties in twenty-four plant species of traditional ethnoveterinary use in the Mediterranean area. Pharmaceutical Biology, 2011; 49: 240–247.
32. Fidrianny I, Ayu D, Hartati R. Antioxidant capacities, phenolic, flavonoid and carotenoid content of various polarities extracts from three organs of Sechium edule ( Jacq.) Swartz. Journal of Chemical and Pharmaceutical Research, 2015; 7: 914–920.
33. Bardarov K, Todorova T, Miteva D, Bardarov, V.; Atanassov, A.; Chankova, S. Preliminary screening for study of the chemical composition of Clinopodium vulgare L. water extract. Comptes rendus de l'Académie bulgare des Sciences, 2016; 69: 717-724.
34. Hong S, Joo T, Jhoo Jin-Woo. Antioxidant and anti-inflammatory activities of 3,5-dicaffeoylquinic acid isolated from Ligularia fischeri leaves. Food Sci. Biotechnol, 2015; 24: 257–263.
35. Cho JY, Kim JY, Lee YG, Lee HJ, Shim HJ, Lee JH, Kim SJ, Ham KS, Moon JH. Four new dicaffeoylquinic acid derivatives from Glasswort (Salicornia herbacea L .) and their antioxidant activity. Molecules, 2016; 21: 1097.
36. Kim HJ, Lee YS. Identification of new dicaffeoylquinic acids from Chrysanthemum morifolium and their antioxidant activities. Planta Medica, 2005; 71: 871–876.
2. Pereira DM, Valentão P, Pereira JA, Andrade PB. Phenolics: From Chemistry to Biology. Molecules, 2009; 14: 2202-2211.
3. Seyoum A, Asres K, El-Fiky FK. Structure–radical scavenging activity relationships of flavonoids. Phytochemistry, 2006; 67: 2058–2070.
4. Heleno S, Martins A, Queiroz M, Ferreira I. Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chemistry, 2015; 173: 501–513.
5. Ali SI, Gopalakrishnan B, Venkatesalu V. Pharmacognosy, phytochemistry and pharmacological properties of Achillea millefolium L.: A Review. Phytotherapy Research, 2017; 31: 1140–1161.
6. Fraisse D, Felgines C, Texier O, Lamaison Jean-Louis. Caffeoyl derivatives: major antioxidant compounds of some wild herbs of the Asteraceae family. Food and Nutrition Sciences, 2011; 2: 181–192.
7. Gil M, Wianowska D. Chlorogenic acids – their properties, occurrence and analysis. Annales Universitatis Marie Curie-Sklodowska Lublin-Polonica, 2017; LXXII:61–104.
8. Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine, 1996; 20: 933–956.
9. Rice-Evans CA, Miller NJ, Paganga G. Antioxidant properties of phenolic compounds. Trends in Plant Science, 1997; 2: 152–159.
10. Clarke G, Ting KN, Wiart C, Fry J. High Correlation of 2,2-diphenyl-1-picrylhydrazyl (DPPH) Radical scavenging, ferric reducing activity potential and total phenolics content indicates redundancy in use of all three assays to screen for antioxidant activity of extracts of plants from the Malaysian rainforest. Antioxidants, 2013; 2: 1–10.
11. Li X, Wu X, Huang L. Correlation between antioxidant activities and phenolic contents of Radix Angelicae Sinensis (Danggui). Molecules, 2009; 14: 5349–5361.
12. Kasangana PB, Haddad PS, Stevanovic T. Study of polyphenol content and antioxidant capacity of Myrianthus arboreus (Cecropiaceae) root bark extracts. Antioxidants, 2015; 4: 410–426.
13. Dias MI, Barros L, Dueñas M, Pereira E, Carvalho AM, Alves RC, Oliveira MB, Santos-Buelga C, Ferreira ICFR. Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction. Food Chemistry, 2013; 141: 4152–4160.
14. Bourgou S, Bettaieb RI, Mkadmini K, Isoda H, Ksouri R, Ksouri WM. LC-ESI-TOF-MS and GC-MS profiling of Artemisia herba-alba and evaluation of its bioactive properties. Food Research International, 2017; 99: 702–712.
15. Alaerts G, Pieters S, Logie H, Erps J, Merino-Arévalo M, Dejaegher B, Smeyers-Verbeke J, Heyden YV. Exploration and classification of chromatographic fingerprints as additional tool for identification and quality control of several Artemisia species. Journal of Pharmaceutical and Biomedical Analysis, 2014; 95: 34–46.
16. Tistaert C, Dejaegher B, Heyden YV. Chromatographic separation techniques and data handling methods for herbal fingerprints: A review. Analytica Chimica Acta, 2011; 690: 148–161.
17. Bojilov D, Dagnon S, Ivanov I. New insight into the flavonoid composition of Chenopodium botrys. Phytochemistry Letters, 2017; 20: 316-321.
18. Edreva A, Vitkova A, Dagnon S, Konakchiev A, Gesheva E, Bojilov D. Field-cultivated medicinal plants of Achillea millefolium group: a source of bioactive compounds. Genetics and Plant Physiology, 2017; 7: 22–33.
19. Docheva M, Dagnon S, Statkova-Abeghe S. Flavonoid content and radical scavenging potential of extracts prepared from tobacco cultivars and waste. Natural Product Research, 2014; 28: 1328-1334.
20. Christapher PV, Parasuraman S, Raj PV, Saghir SAM, Asmawi MZ, Vikneswaran M. Influence of extracting solvent on pharmacological activity and cytotoxicity of Polygonum minus, a commonly consumed herb in Southeast Asia. Pharmacogn Magazine, 2016; 12: 424–430.
21. Dai J. Mumper R. Plant Phenolics: Extraction, analysis and their antioxidant and anticancer properties. Molecules, 2010; 15: 7313-7352.
22. Khoddami A, Wilkes M, Roberts T. Techniques for analysis of plant phenolic compounds. Molecules, 2013; 18: 2328-2375.
23. Chen Y. Extraction and HPLC characterization of chlorogenic acid from tobacco residuals. Separation Science and Technology, 2007; 42: 3481-3492.
24. Biesaga M. Influence of extraction methods on stability of flavonoids. Journal of Chromatography A, 2011; 1218: 2505-2512.
25. Yang J, Ou XQ, Zhang X, Zhou ZY, Ma LY. Effect of different solvents on the measurement of phenolics and the antioxidant activity of Mulberry (Morus atropurpurea Roxb.) with accelerated solvent extraction. Journal of Food Science, 2017; 82: 605–612.
26. Zhang Y, Zhang X, Ma Y, Wang J, Yongxiang K, Wang D. Correlation analysis between the high-performance liquid chromatography (HPLC) fingerprint of antioxidants and flavonoids of Polygonatum odorantum. Journal of Medicinal Plants Research, 2013; 7: 1114–1120.
27. Yordi EG, Pérez EM, Matos MJ, Villares EU. Antioxidant and pro-oxidant effects of polyphenolic compounds and structure-activity relationship. Chapter 2, Nutrition, Well-Being and Health, 2012, pp. 24-48.
28. Amić D, Davidovic-Amić D, Bešlo D, Trinajstić N. Structure-radical scavenging activity relationships of flavonoids. Croatica Chemica Acta, 2003; 76: 55–61.
29. Velkov ZA, Kolev MK, Tadjer AV. Modeling and statistical analysis of DPPH scavenging activity of phenolics. Collection of Czechoslovak Chemical Communications, 2007; 72: 1461–1471.
30. Cai YZ, Mei SJX, Luo Q, Corke H. Structure–radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sciences, 2006; 78: 2872–2888.
31. Piluzza G, Bullitta S. Correlations between phenolic content and antioxidant properties in twenty-four plant species of traditional ethnoveterinary use in the Mediterranean area. Pharmaceutical Biology, 2011; 49: 240–247.
32. Fidrianny I, Ayu D, Hartati R. Antioxidant capacities, phenolic, flavonoid and carotenoid content of various polarities extracts from three organs of Sechium edule ( Jacq.) Swartz. Journal of Chemical and Pharmaceutical Research, 2015; 7: 914–920.
33. Bardarov K, Todorova T, Miteva D, Bardarov, V.; Atanassov, A.; Chankova, S. Preliminary screening for study of the chemical composition of Clinopodium vulgare L. water extract. Comptes rendus de l'Académie bulgare des Sciences, 2016; 69: 717-724.
34. Hong S, Joo T, Jhoo Jin-Woo. Antioxidant and anti-inflammatory activities of 3,5-dicaffeoylquinic acid isolated from Ligularia fischeri leaves. Food Sci. Biotechnol, 2015; 24: 257–263.
35. Cho JY, Kim JY, Lee YG, Lee HJ, Shim HJ, Lee JH, Kim SJ, Ham KS, Moon JH. Four new dicaffeoylquinic acid derivatives from Glasswort (Salicornia herbacea L .) and their antioxidant activity. Molecules, 2016; 21: 1097.
36. Kim HJ, Lee YS. Identification of new dicaffeoylquinic acids from Chrysanthemum morifolium and their antioxidant activities. Planta Medica, 2005; 71: 871–876.
Published
01-05-2018
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“THE RELATIONSHIP BETWEEN MAIN POLYPHENOL COMPONENTS AND FREE RADICAL SCAVENGING ACTIVITY OF SELECTED MEDICINAL PLANTS”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 3, May 2018, pp. 131-8, https://doi.org/10.25004/IJPSDR.2018.100305.
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How to Cite
“THE RELATIONSHIP BETWEEN MAIN POLYPHENOL COMPONENTS AND FREE RADICAL SCAVENGING ACTIVITY OF SELECTED MEDICINAL PLANTS”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 3, May 2018, pp. 131-8, https://doi.org/10.25004/IJPSDR.2018.100305.
