The Extraction of Antioxidant Compounds from Coriandrum sativum Seeds by Using Green Solvents
Year 2024,
, 1329 - 1338, 30.08.2024
Özge Demir
,
Aslı Gök
,
Şahismail Kırbaşlar
Abstract
In this study, bioactive compounds from Coriandrum sativum seeds were extracted by microwave assisted extraction (MAE) using natural deep eutectic solvents (NADESs). The total antioxidant capacity (TAC) of extracts was determined by using cupric reducing antioxidant capacity (CUPRAC) method. 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) analyses have been employed to measure the free radical scavenging ability of the sample extracts. Five different deep eutectic solvents, using choline chloride in combination with hydrogen bond donors (three polyalcohols and two organic acids) were firstly scanned. Choline chloride and 1,4-butanediol at the molar ratio of 1:4 was the best solvent of choice to extract natural antioxidants to achieve the best level of TAC. The response surface methodology (RSM) was applied to achieve the most advantageous conditions. The optimal process conditions for the maximum TAC value were as follows: 326 watt microwave power, 88 second extraction time, and 10 liquid/solid (L/S) ratio. In this study, we report an efficient, rapid, and green method to extract natural antioxidants from Turkish Coriandrum sativum seeds.
References
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- 25. Lalikoglu M, Aşçı YS, Sırma Tarım B, Yıldız M, Arat R. Hydrophobic deep eutectic solvent effect on acrylic acid separation from aqueous media by using reactive extraction and modeling with response surface methodology. Sep Sci Technol [Internet]. 2022 Jul 3;57(10):1563–74. Available from: <URL>.
- 26. Lalikoglu M. Separation of butyric acid from aqueous media using menthol-based hydrophobic deep eutectic solvent and modeling by response surface methodology. Biomass Convers Biorefinery [Internet]. 2022 Apr 14;12(4):1331–41. Available from: <URL>.
- 27. Doldolova K, Bener M, Lalikoğlu M, Aşçı YS, Arat R, Apak R. Optimization and modeling of microwave-assisted extraction of curcumin and antioxidant compounds from turmeric by using natural deep eutectic solvents. Food Chem [Internet]. 2021 Aug 15;353:129337. Available from: <URL>.
- 28. Esin Çelik S, Özyürek M, Güçlü K, Çapanoğlu E, Apak R. Identification and anti‐oxidant capacity determination of phenolics and their glycosides in elderflower by On‐line HPLC–CUPRAC Method. Phytochem Anal [Internet]. 2014 Mar 10;25(2):147–54. Available from: <URL>.
- 29. Bener M, Şen FB, Önem AN, Bekdeşer B, Çelik SE, Lalikoglu M, et al. Microwave-assisted extraction of antioxidant compounds from by-products of Turkish hazelnut (Corylus avellana L.) using natural deep eutectic solvents: Modeling, optimization and phenolic characterization. Food Chem [Internet]. 2022 Aug 15;385:132633. Available from: <URL>.
- 30. Altun M, Çelik SE, Güçlü K, Özyürek M, Erçağ E, Apak R. Total antioxidant capacity and phenolic contents of Turkish hazelnut (Corylus Avellana L.) kernels and oils. J Food Biochem [Internet]. 2013 Feb 1;37(1):53–61. Available from: <URL>.
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- 35. Wan Mahmood WMA, Lorwirachsutee A, Theodoropoulos C, Gonzalez-Miquel M. Polyol-based deep eutectic solvents for extraction of natural polyphenolic antioxidants from Chlorella vulgaris. ACS Sustain Chem Eng [Internet]. 2019 Mar 4;7(5):5018–26. Available from: <URL>.
- 36. Zheng B, Yuan Y, Xiang J, Jin W, Johnson JB, Li Z, et al. Green extraction of phenolic compounds from foxtail millet bran by ultrasonic-assisted deep eutectic solvent extraction: Optimization, comparison and bioactivities. LWT [Internet]. 2022 Jan 15;154:112740. Available from: <URL>.
- 37. Wang M, Wang J, Zhang Y, Xia Q, Bi W, Yang X, et al. Fast environment-friendly ball mill-assisted deep eutectic solvent-based extraction of natural products. J Chromatogr A [Internet]. 2016 Apr 22;1443:262–6. Available from: <URL>.
- 38. Duan L, Dou LL, Guo L, Li P, Liu EH. Comprehensive evaluation of deep eutectic solvents in extraction of bioactive natural products. ACS Sustain Chem Eng [Internet]. 2016 Apr 4;4(4):2405–11. Available from: <URL>.
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- 40. Cui Q, Peng X, Yao XH, Wei ZF, Luo M, Wang W, et al. Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots. Sep Purif Technol [Internet]. 2015 Aug 17;150:63–72. Available from: <URL>.
- 41. Loarce L, Oliver-Simancas R, Marchante L, Díaz-Maroto MC, Alañón ME. Implementation of subcritical water extraction with natural deep eutectic solvents for sustainable extraction of phenolic compounds from winemaking by-products. Food Res Int [Internet]. 2020 Nov 1;137:109728. Available from: <URL>.
- 42. Zannou O, Koca I. Greener extraction of anthocyanins and antioxidant activity from blackberry (Rubus spp) using natural deep eutectic solvents. LWT [Internet]. 2022 Mar 15;158:113184. Available from: <URL>.
- 43. Alsaud N, Shahbaz K, Farid M. Application of deep eutectic solvents in the extraction of polyphenolic antioxidants from New Zealand Manuka leaves (Leptospermum Scoparium): Optimization and antioxidant activity. J Mol Liq [Internet]. 2021 Sep 1;337:116385. Available from: <URL>.
- 44. Wang G, Cui Q, Yin LJ, Zheng X, Gao MZ, Meng Y, et al. Efficient extraction of flavonoids from Flos Sophorae Immaturus by tailored and sustainable deep eutectic solvent as green extraction media. J Pharm Biomed Anal [Internet]. 2019 Jun 5;170:285–94. Available from: <URL>.
- 45. Cao J, Chen L, Li M, Cao F, Zhao L, Su E. Efficient extraction of proanthocyanidin from Ginkgo biloba leaves employing rationally designed deep eutectic solvent-water mixture and evaluation of the antioxidant activity. J Pharm Biomed Anal [Internet]. 2018 Sep 5;158:317–26. Available from: <URL>.
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Year 2024,
, 1329 - 1338, 30.08.2024
Özge Demir
,
Aslı Gök
,
Şahismail Kırbaşlar
References
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- 2. Zeković Z, Vidović S, Vladić J, Radosavljević R, Cvejin A, Elgndi MA, et al. Optimization of subcritical water extraction of antioxidants from Coriandrum sativum seeds by response surface methodology. J Supercrit Fluids [Internet]. 2014 Nov 1;95:560–6. Available from: <URL>.
- 3. Bhat S, Kaushal P, Kaur M, Sharma HK. Coriander (Coriandrum sativum L.): Processing, nutritional and functional aspects. African J Plant Sci [Internet]. 2014 Jan 31;8(1):25–33. Available from: <URL>.
- 4. Senrayan J, Venkatachalam S. Optimization of ultrasound-assisted solvent extraction (UASE) based on oil yield, antioxidant activity and evaluation of fatty acid composition and thermal stability of Coriandrum sativum L. seed oil. Food Sci Biotechnol [Internet]. 2019 Apr 17;28(2):377–86. Available from: <URL>.
- 5. Laribi B, Kouki K, M’Hamdi M, Bettaieb T. Coriander (Coriandrum sativum L.) and its bioactive constituents. Fitoterapia [Internet]. 2015 Jun 1;103:9–26. Available from: <URL>.
- 6. Asgarpanah J, Kazemivash N. Phytochemistry, pharmacology and medicinal properties of Coriandrum sativum L. African J Pharm Pharmacol [Internet]. 2012 Aug 22;6(31):2340–5. Available from: <URL>.
- 7. Deepa B, Anuradha C V. Antioxidant potential of Coriandrum sativum L. seed extract. Indian J Exp Biol 2011 [Internet]. 2011;49:30–8. Available from: <URL>.
- 8. Zeković Z, Kaplan M, Pavlić B, Olgun EO, Vladić J, Canlı O, et al. Chemical characterization of polyphenols and volatile fraction of coriander (Coriandrum sativum L.) extracts obtained by subcritical water extraction. Ind Crops Prod [Internet]. 2016 Sep 1;87:54–63. Available from: <URL>.
- 9. Soto-Vaca A, Gutierrez A, Losso JN, Xu Z, Finley JW. Evolution of phenolic compounds from color and flavor problems to health benefits. J Agric Food Chem [Internet]. 2012 Jul 11;60(27):6658–77. Available from: <URL>.
- 10. Dziki D, Różyło R, Gawlik-Dziki U, Świeca M. Current trends in the enhancement of antioxidant activity of wheat bread by the addition of plant materials rich in phenolic compounds. Trends Food Sci Technol [Internet]. 2014 Nov 1;40(1):48–61. Available from: <URL>.
- 11. Azmir J, Zaidul ISM, Rahman MM, Sharif KM, Mohamed A, Sahena F, et al. Techniques for extraction of bioactive compounds from plant materials: A review. J Food Eng [Internet]. 2013 Aug 1;117(4):426–36. Available from: <URL>.
- 12. Zainal-Abidin MH, Hayyan M, Hayyan A, Jayakumar NS. New horizons in the extraction of bioactive compounds using deep eutectic solvents: A review. Anal Chim Acta [Internet]. 2017 Aug 1;979:1–23. Available from: <URL>.
- 13. Skarpalezos D, Detsi A. Deep eutectic solvents as extraction media for valuable flavonoids from natural sources. Appl Sci [Internet]. 2019 Oct 4;9(19):4169. Available from: <URL>.
- 14. Jurić T, Mićić N, Potkonjak A, Milanov D, Dodić J, Trivunović Z, et al. The evaluation of phenolic content, in vitro antioxidant and antibacterial activity of Mentha piperita extracts obtained by natural deep eutectic solvents. Food Chem [Internet]. 2021 Nov 15;362:130226. Available from: <URL>.
- 15. García A, Rodríguez-Juan E, Rodríguez-Gutiérrez G, Rios JJ, Fernández-Bolaños J. Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). Food Chem [Internet]. 2016 Apr 15;197:554–61. Available from: <URL>.
- 16. Altunay N, Elik A, Gürkan R. Preparation and application of alcohol based deep eutectic solvents for extraction of curcumin in food samples prior to its spectrophotometric determination. Food Chem [Internet]. 2020 Apr 25;310:125933. Available from: <URL>.
- 17. Xu H, Peng J, Kong Y, Liu Y, Su Z, Li B, et al. Key process parameters for deep eutectic solvents pretreatment of lignocellulosic biomass materials: A review. Bioresour Technol [Internet]. 2020 Aug 1;310:123416. Available from: <URL>.
- 18. Tang B, Bi W, Zhang H, Row KH. Deep Eutectic Solvent-Based HS-SME Coupled with GC for the analysis of bioactive terpenoids in Chamaecyparis obtusa leaves. Chromatographia [Internet]. 2014 Feb 28;77(3–4):373–7. Available from: <URL>.
- 19. Dhanani T, Singh R, Shah S, Kumari P, Kumar S. Comparison of green extraction methods with conventional extraction method for extract yield, L-DOPA concentration and antioxidant activity of Mucuna pruriens seed. Green Chem Lett Rev [Internet]. 2015 Apr 3;8(2):43–8. Available from: <URL>.
- 20. Bimakr M, Rahman RA, Taip FS, Ganjloo A, Salleh LM, Selamat J, et al. Comparison of different extraction methods for the extraction of major bioactive flavonoid compounds from spearmint (Mentha spicata L.) leaves. Food Bioprod Process [Internet]. 2011 Jan 1;89(1):67–72. Available from: <URL>.
- 21. Liu JZ, Lyu HC, Fu YJ, Jiang JC, Cui Q. Simultaneous extraction of natural organic acid and flavonoid antioxidants from Hibiscus manihot L. flower by tailor-made deep eutectic solvent. LWT [Internet]. 2022 Jun 15;163:113533. Available from: <URL>.
- 22. Chanioti S, Tzia C. Extraction of phenolic compounds from olive pomace by using natural deep eutectic solvents and innovative extraction techniques. Innov Food Sci Emerg Technol [Internet]. 2018 Aug 1;48:228–39. Available from: <URL>.
- 23. Meng Z, Zhao J, Duan H, Guan Y, Zhao L. Green and efficient extraction of four bioactive flavonoids from Pollen Typhae by ultrasound-assisted deep eutectic solvents extraction. J Pharm Biomed Anal [Internet]. 2018 Nov 30;161:246–53. Available from: <URL>.
- 24. Yalçın Ö, Baylan N, Çehreli S. Adsorption of levodopa onto Amberlite resins: equilibrium studies and D-optimal modeling based on response surface methodology. Biomass Convers Biorefinery [Internet]. 2022 Apr 9;12(4):1281–94. Available from: <URL>.
- 25. Lalikoglu M, Aşçı YS, Sırma Tarım B, Yıldız M, Arat R. Hydrophobic deep eutectic solvent effect on acrylic acid separation from aqueous media by using reactive extraction and modeling with response surface methodology. Sep Sci Technol [Internet]. 2022 Jul 3;57(10):1563–74. Available from: <URL>.
- 26. Lalikoglu M. Separation of butyric acid from aqueous media using menthol-based hydrophobic deep eutectic solvent and modeling by response surface methodology. Biomass Convers Biorefinery [Internet]. 2022 Apr 14;12(4):1331–41. Available from: <URL>.
- 27. Doldolova K, Bener M, Lalikoğlu M, Aşçı YS, Arat R, Apak R. Optimization and modeling of microwave-assisted extraction of curcumin and antioxidant compounds from turmeric by using natural deep eutectic solvents. Food Chem [Internet]. 2021 Aug 15;353:129337. Available from: <URL>.
- 28. Esin Çelik S, Özyürek M, Güçlü K, Çapanoğlu E, Apak R. Identification and anti‐oxidant capacity determination of phenolics and their glycosides in elderflower by On‐line HPLC–CUPRAC Method. Phytochem Anal [Internet]. 2014 Mar 10;25(2):147–54. Available from: <URL>.
- 29. Bener M, Şen FB, Önem AN, Bekdeşer B, Çelik SE, Lalikoglu M, et al. Microwave-assisted extraction of antioxidant compounds from by-products of Turkish hazelnut (Corylus avellana L.) using natural deep eutectic solvents: Modeling, optimization and phenolic characterization. Food Chem [Internet]. 2022 Aug 15;385:132633. Available from: <URL>.
- 30. Altun M, Çelik SE, Güçlü K, Özyürek M, Erçağ E, Apak R. Total antioxidant capacity and phenolic contents of Turkish hazelnut (Corylus Avellana L.) kernels and oils. J Food Biochem [Internet]. 2013 Feb 1;37(1):53–61. Available from: <URL>.
- 31. Bener M. Modeling and optimizing microwave-assisted extraction of antioxidants from Thymbra Spicata L. and characterization of their phenolic constituents. Food Sci Biotechnol [Internet]. 2019 Dec 11;28(6):1733–45. Available from: <URL>.
- 32. Sanchez-Moreno C, Larrauri JA, Saura-Calixto F. A procedure to measure the antiradical efficiency of polyphenols. J Sci Food Agric [Internet]. 1998;76:270–6. Available from: <URL>.
- 33. Ozturk B, Parkinson C, Gonzalez-Miquel M. Extraction of polyphenolic antioxidants from orange peel waste using deep eutectic solvents. Sep Purif Technol [Internet]. 2018 Nov 29;206:1–13. Available from: <URL>.
- 34. Barbieri JB, Goltz C, Batistão Cavalheiro F, Theodoro Toci A, Igarashi-Mafra L, Mafra MR. Deep eutectic solvents applied in the extraction and stabilization of rosemary (Rosmarinus officinalis L.) phenolic compounds. Ind Crops Prod [Internet]. 2020 Feb 1;144:112049. Available from: <URL>.
- 35. Wan Mahmood WMA, Lorwirachsutee A, Theodoropoulos C, Gonzalez-Miquel M. Polyol-based deep eutectic solvents for extraction of natural polyphenolic antioxidants from Chlorella vulgaris. ACS Sustain Chem Eng [Internet]. 2019 Mar 4;7(5):5018–26. Available from: <URL>.
- 36. Zheng B, Yuan Y, Xiang J, Jin W, Johnson JB, Li Z, et al. Green extraction of phenolic compounds from foxtail millet bran by ultrasonic-assisted deep eutectic solvent extraction: Optimization, comparison and bioactivities. LWT [Internet]. 2022 Jan 15;154:112740. Available from: <URL>.
- 37. Wang M, Wang J, Zhang Y, Xia Q, Bi W, Yang X, et al. Fast environment-friendly ball mill-assisted deep eutectic solvent-based extraction of natural products. J Chromatogr A [Internet]. 2016 Apr 22;1443:262–6. Available from: <URL>.
- 38. Duan L, Dou LL, Guo L, Li P, Liu EH. Comprehensive evaluation of deep eutectic solvents in extraction of bioactive natural products. ACS Sustain Chem Eng [Internet]. 2016 Apr 4;4(4):2405–11. Available from: <URL>.
- 39. Cui Q, Liu JZ, Wang LT, Kang YF, Meng Y, Jiao J, et al. Sustainable deep eutectic solvents preparation and their efficiency in extraction and enrichment of main bioactive flavonoids from sea buckthorn leaves. J Clean Prod [Internet]. 2018 May 20;184:826–35. Available from: <URL>.
- 40. Cui Q, Peng X, Yao XH, Wei ZF, Luo M, Wang W, et al. Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots. Sep Purif Technol [Internet]. 2015 Aug 17;150:63–72. Available from: <URL>.
- 41. Loarce L, Oliver-Simancas R, Marchante L, Díaz-Maroto MC, Alañón ME. Implementation of subcritical water extraction with natural deep eutectic solvents for sustainable extraction of phenolic compounds from winemaking by-products. Food Res Int [Internet]. 2020 Nov 1;137:109728. Available from: <URL>.
- 42. Zannou O, Koca I. Greener extraction of anthocyanins and antioxidant activity from blackberry (Rubus spp) using natural deep eutectic solvents. LWT [Internet]. 2022 Mar 15;158:113184. Available from: <URL>.
- 43. Alsaud N, Shahbaz K, Farid M. Application of deep eutectic solvents in the extraction of polyphenolic antioxidants from New Zealand Manuka leaves (Leptospermum Scoparium): Optimization and antioxidant activity. J Mol Liq [Internet]. 2021 Sep 1;337:116385. Available from: <URL>.
- 44. Wang G, Cui Q, Yin LJ, Zheng X, Gao MZ, Meng Y, et al. Efficient extraction of flavonoids from Flos Sophorae Immaturus by tailored and sustainable deep eutectic solvent as green extraction media. J Pharm Biomed Anal [Internet]. 2019 Jun 5;170:285–94. Available from: <URL>.
- 45. Cao J, Chen L, Li M, Cao F, Zhao L, Su E. Efficient extraction of proanthocyanidin from Ginkgo biloba leaves employing rationally designed deep eutectic solvent-water mixture and evaluation of the antioxidant activity. J Pharm Biomed Anal [Internet]. 2018 Sep 5;158:317–26. Available from: <URL>.
- 46. Xu M, Ran L, Chen N, Fan X, Ren D, Yi L. Polarity-dependent extraction of flavonoids from citrus peel waste using a tailor-made deep eutectic solvent. Food Chem [Internet]. 2019 Nov 1;297:124970. Available from: <URL>.
- 47. Evlik T, Aşçı YS, Baylan N, Gamsızkan H, Çehreli S. Reactive separation of malic acid from aqueous solutions and modeling by artificial neural network (ANN) and response surface methodology (RSM). J Dispers Sci Technol [Internet]. 2022;43(2):221–30. Available from: <URL>.
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