Well-Designed Hydrophobic Deep Eutectic Solvents As Green and Efficient Media for the Extraction of Artemisinin from Artemisia annua Leaves

ACS Sustainable Chemistry and Engineering

Volumn 5, Issue 4, 2017, Pages 3270-3278

  Cao, Jun ^a   Yang, Meng ^a   Cao, Fuliang ^a   Wang, Jiahong ^a   Su, Erzheng ^a,b  

^a NANJING FORESTRY UNIVERSITY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Artemisia annua leaves; Artemisinin; Designer solvent; Extraction; Hydrophobic deep eutectic solvents

Indexed keywords

BIOMASS; EUTECTICS; HYDROPHILICITY; HYDROPHOBICITY; PARTICLE SIZE; PLANTS (BOTANY); SOLVENT EXTRACTION; SOLVENTS;

AB-8 MACROPOROUS RESINS; ARTEMISIA ANNUA; ARTEMISININ; CENTRAL COMPOSITE DESIGNS; DEEP EUTECTIC SOLVENTS; PHARMACEUTICAL APPLICATIONS; RESPONSE SURFACE METHODOLOGY; ULTRASOUND-ASSISTED EXTRACTION;

EXTRACTION;

EUTECTICS; EXTRACTION; LEAVES; SOLVENTS;

EID: 85016986641     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b03092     Document Type: Article

References (34)

1. Stringham, R. W.; Pennell, M.; Cabri, W.; Carzana, G.; Giorgi, F.; Lalli, S.; Marazzi, G.; Torri, M. Identification of impurities in artemisinin, their behavior in high performance liquid chromatography and implications for the quality of derived anti-malarial drugs J. Chromatogr. A 2011, 1218, 6838-6842 10.1016/j.chroma.2011.07.069
2. Briars, R.; Paniwnyk, L. Effect of ultrasound on the extraction of artemisinin from Artemisia annua Ind. Crops Prod. 2013, 42, 595-600 10.1016/j.indcrop.2012.06.043
3. Lapkin, A. A.; Plucinski, P. K.; Cutler, M. Comparative assessment of technologies for extraction of artemisinin J. Nat. Prod. 2006, 69, 1653-1664 10.1021/np060375j
4. Wang, X.; Zhao, X.; Yang, B.; Dong, H.; Liu, D.; Huang, L. A combination of ultrasonic-assisted extraction with RRLC-QQQ method for the determination of artemisinin in the Chinese herb Artemisia annua L Phytochem. Anal. 2011, 22, 280-284 10.1002/pca.1277
5. Soktoeva, T. E.; Ryzhova, G. L.; Dychko, K. A.; Khasanov, V. V.; Zhigzhitzhapova, S. V.; Radnaeva, L. D. Artemisinin content in Artemisia annua L. extracts obtained by different methods Russ. J. Bioorg. Chem. 2013, 39, 761-764 10.1134/S1068162012070199
6. Briars, R.; Paniwnyk, L. Effect of ultrasound on the extraction of artemisinin from Artemisia annua Ind. Crops Prod. 2013, 42, 595-600 10.1016/j.indcrop.2012.06.043
7. Zhang, H.; Zhang, L.; Hu, X.; Zhou, Y.; Ding, C.; Yang, R.; Wang, X.; Li, D. Optimization of ultrasound-assisted extraction of artemisinin from Artemisia annua L. by response surface methodology Sep. Sci. Technol. 2014, 49, 673-681 10.1080/01496395.2013.862545
8. Lapkin, A. A.; Walker, A.; Sullivan, N.; Khambay, B.; Mlambo, B.; Chemat, S. Development of HPLC analytical protocols for quantification of artemisinin in biomass and extracts J. Pharm. Biomed. Anal. 2009, 49, 908-915 10.1016/j.jpba.2009.01.025
9. Abou-Shehada, S.; Clark, J. H.; Paggiola, G.; Sherwood, J. Tunable solvents: shades of green Chem. Eng. Process. 2016, 99, 88-96 10.1016/j.cep.2015.07.005
10. Francisco, M.; van den Bruinhorst, A.; Kroon, M. C. Low-transition-temperature mixtures (LTTMs): a new generation of designer solvents Angew. Chem., Int. Ed. 2013, 52, 3074-3085 10.1002/anie.201207548
11. Durand, E.; Lecomte, J.; Villeneuve, P. From green chemistry to nature: the versatile role of low transition temperature mixtures Biochimie 2016, 120, 119-123 10.1016/j.biochi.2015.09.019
12. Paiva, A.; Craveiro, R.; Aroso, I.; Martins, M.; Reis, R. L.; Duarte, A. R. C. Natural deep eutectic solvents - solvents for the 21st century ACS Sustainable Chem. Eng. 2014, 2, 1063-1071 10.1021/sc500096j
13. Nam, M. W.; Zhao, J.; Lee, M. S.; Jeong, J. H.; Lee, J. Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae Green Chem. 2015, 17, 1718-1727 10.1039/C4GC01556H
14. Qi, X.; Peng, X.; Huang, Y.; Li, L.; Wei, Z.; Zu, Y.; Fu, Y. Green and efficient extraction of bioactive flavonoids from Equisetum palustre L. by deep eutectic solvents-based negative pressure cavitation method combined with macroporous resin enrichment Ind. Crops Prod. 2015, 70, 142-148 10.1016/j.indcrop.2015.03.026
15. Jeong, K. M.; Lee, M. S.; Nam, M. W.; Zhao, J.; Jin, Y.; Lee, D.; Kwon, S. W.; Jeong, J. H.; Lee, J. Tailoring and recycling of deep eutectic solvents as sustainable and efficient extraction media J. Chromatogr. A 2015, 1424, 10-17 10.1016/j.chroma.2015.10.083
16. Mouratoglou, E.; Malliou, V.; Makris, D. P. Novel glycerol-based natural eutectic mixtures and their efficiency in the ultrasound-assisted extraction of antioxidant polyphenols from agri-food waste biomass Waste Biomass Valorization 2016, 7, 1377 10.1007/s12649-016-9539-8
17. van Osch, D. J. G. P.; Zubeir, L. F.; van den Bruinhorst, A.; Rocha, M. A. A.; Kroon, M. C. Hydrophobic deep eutectic solvents as water-immiscible extractants Green Chem. 2015, 17, 4518-4521 10.1039/C5GC01451D
18. Xia, Y.; Zeng, J.; Zhao, B.; Wang, Y. Analysis of artemisinin in 1-ethyl-3-methylimidazolium bromide-water system by reversed phase high performance liquid chromatography Chin. J. Anal. Chem. 2009, 37, 573-576
19. Ponnusamy, C.; Krishnaswami, V.; Sugumaran, A.; Natesan, S. Simultaneous estimation of artemisinin and dexamethasone in nanodispersions and assessment of ex-vivo corneal transport study by RP-HPLC Curr. Pharm. Anal. 2014, 10, 44-50 10.2174/157341291001140102111031
20. Zhang, R. S.; Wang, Y.; Zhao, M. Analysis of artemisinin from Artemisia annua L. by HPLC-UV using pre-column derivatization Chem. Ind. Forest Prod. 2009, 29, 115-119
21. Stringham, R. W.; Lynam, K. G.; Mrozinski, P.; Kilby, G.; Pelczer, I.; Kraml, C. High performance liquid chromatographic evaluation of artemisinin, raw material in the synthesis of artesunate and artemether J. Chromatogr. A 2009, 1216, 8918-8925 10.1016/j.chroma.2009.10.056
22. Naser, J.; Mjalli, F.; Jibril, B.; Al-Hatmi, S.; Gano, Z. Potassium carbonate as a salt for deep eutectic solvents Int. J. Chem. Eng. Appl. 2013, 114-118 10.7763/IJCEA.2013.V4.275
23. Yusof, R.; Abdulmalek, E.; Sirat, K.; Rahman, M. Tetrabutylammonium bromide (TBABr)-based deep eutectic solvents (DESs) and their physical properties Molecules 2014, 19, 8011-8026 10.3390/molecules19068011
24. Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K.; Tambyrajah, V. Novel solvent properties of choline chloride/urea mixtures Chem. Commun. 2003, 1, 70-71 10.1039/b210714g
25. Fischer, V.; Kunz, W. Properties of sugar-based low-melting mixtures Mol. Phys. 2014, 112, 1241-1245 10.1080/00268976.2014.884249
26. Peng, X.; Duan, M.; Yao, X.; Zhang, Y.; Zhao, C.; Zu, Y.; Fu, Y. Green extraction of five target phenolic acids from Lonicerae japonicae Flos with deep eutectic solvent Sep. Purif. Technol. 2016, 157, 249-257 10.1016/j.seppur.2015.10.065
27. Bezerra, M. A.; Santelli, R. E.; Oliveira, E. P.; Villar, L. S.; Escaleira, L. A. Response surface methodology (RSM) as a tool for optimization in analytical chemistry Talanta 2008, 76, 965-977 10.1016/j.talanta.2008.05.019
28. Khalil, M.; Darusman, L. K.; Syafitri, U. D. Application of fractional factorial design to optimize extraction method of artemisinin from Artemisia annua L ScienceAsia 2011, 37, 219-224 10.2306/scienceasia1513-1874.2011.37.219
29. Lapkin, A. A.; Peters, M.; Greiner, L.; Chemat, S.; Leonhard, K.; Liauw, M. A.; Leitner, W. Screening of new solvents for artemisinin extraction process using ab initio methodology Green Chem. 2010, 12, 241-251 10.1039/B922001A
30. Hao, J. Y.; Han, W.; Huang, S. D.; Xue, B. Y.; Deng, X. Microwave-assisted extraction of artemisinin from Artemisia annua L Sep. Purif. Technol. 2002, 28, 191-196 10.1016/S1383-5866(02)00043-6
31. Dai, Y.; Witkamp, G.; Verpoorte, R.; Choi, Y. H. Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L Anal. Chem. 2013, 85, 6272-6278 10.1021/ac400432p
32. Li, J.; Han, Z.; Zou, Y.; Yu, B. Efficient extraction of major catechins in Camellia sinensis leaves using green choline chloride-based deep eutectic solvents RSC Adv. 2015, 5, 93937-93944 10.1039/C5RA15830C
33. Phadtare, S. B.; Shankarling, G. S. Halogenation reactions in biodegradable solvent: efficient bromination of substituted 1-aminoanthra-9,10-quinone in deep eutectic solvent (choline chloride: urea) Green Chem. 2010, 12, 458-462 10.1039/b923589b
34. Li, C.; Li, D.; Zou, S.; Li, Z.; Yin, J.; Wang, A.; Cui, Y.; Yao, Z.; Zhao, Q. Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents Green Chem. 2013, 15, 2793-2799 10.1039/c3gc41067f