Highly efficient and selective extraction of minor bioactive natural products using pure ionic liquids: Application to prenylated flavonoids in licorice

Shuai Ji; Yujie Wang; Shikai Gao; Xian Shao; Wei Cui; Yan Du; Mengzhe Guo; Daoquan Tang

Journal of Industrial and Engineering Chemistry, Vol.80, 352-360, December, 2019

DOI10.1016/j.jiec.2019.08.014 Export Citation

Highly efficient and selective extraction of minor bioactive natural products using pure ionic liquids: Application to prenylated flavonoids in licorice

Shuai Ji, Yujie Wang, Shikai Gao, Xian Shao, Wei Cui¹, Yan Du, Mengzhe Guo, and Daoquan Tang^†

Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, 209 Tongshan Road, Xuzhou 221004, China
¹School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, 19A Yuquan Road, Beijing 100049, China

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Lots of minor constituents in herbal medicines have shown great potential to devolve into lead compounds, and their extraction is attracting more and more attention in pharmaceutical industry. This study provided an example that showed efficient and selective extraction of minor bioactive natural products (prenylated flavonoids with anti-cancer activities) from an herbal medicine (licorice) using pure ionic liquids as green solvents. After investigation of a variety of hydrophobic ionic liquids with ultrasonic-assisted extraction, we found that [C8MIM]BF4 (1-octyl-3-methylimidazolium tetrafluoroborate) was the most effective one for extraction of five representative compounds (isoangustone A, glycycoumarin, licoisoflavanone, licoricidin and glabridin), and solvent to solid ratio, extraction time, extraction temperature and soaking time were then optimized through single-factor experiments and response surface methodology. As a result, the established method had significantly higher extraction selectivity than conventional organic solvents, which could be attributed to significant physical change of licorice microstructures after extraction, as well as strong interactions (especially hydrogen bond interactions) between [C8MIM]BF4 and prenylated flavonoids by mechanism study. In addition, 78.92% of the extracted prenylated flavonoids could be readily recovered from [C8MIM]BF4 by using reversed-phase solid phase extraction, and the recyclability of [C8MIM]BF4 was also confirmed.

Keywords:Ionic liquid;Prenylatedflavonoid;Selective extraction;Minor constituent;Licorice

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[2] Hu YL, Hu K, Kong LM, Xia F, Yang XW, Xu G, Org. Lett., 21, 1007 (2019)

[3] Wang S, Jiao J, Wang X, Ga Q, Kou P, Xu W, Luo M, Zhao C, Fu YJ, J. Ind. Eng. Chem., 70, 402 (2019)

[4] Li A, Xuan H, Sun A, Liu R, Cui J, J. Chromatogr. B, 1012, 42 (2016)

[5] Kim BK, Lee EJ, Kang YJ, Lee JJ, J. Ind. Eng. Chem., 61, 388 (2018)

[6] Passos H, Freire MG, Coutinho JAP, Green Chem., 16, 4786 (2014)

[7] Wang W, Li Q, Liu Y, Chen B, Ultrason. Sonochem., 24, 13 (2015)

[8] Usuki T, Yasuda N, Yoshizawa-Fujita M, Rikukawa M, Chem. Commun., 47, 10560 (2011)

[9] Jiao J, Gai QY, Fu YJ, Zu YG, Luo M, Zhao CJ, Li CY, Sep. Purif. Technol., 107, 228 (2013)

[10] Chowdhury SA, Vijayaraghavan R, MacFarlane DR, Green Chem., 12, 1023 (2010)

[11] Barron D, Ibrahim RK, Phytochemistry, 43, 921 (1996)

[12] Boozari M, Soltani S, Iranshahi M, Phytother. Res., 33, 546 (2019)

[13] Ji S, Qiao X, Li ZW, Wang YR, Yu SW, Liang WF, Lin XH, Ye M, RSC Adv., 5, 45258 (2015)

[14] Ji S, Li ZW, Song W, Wang YR, Liang WF, Li K, Tang SN, Wang Q, Qiao X, Zhou DM, Yu SW, Ye M, J. Nat. Prod., 79, 281 (2016)

[15] Huang W, Tang S, Qiao X, Ma W, Ji S, Wang K, Ye M, Yu S, Fitoterapia, 94, 36 (2012)

[16] Ji S, Tang S, Li K, Li Z, Liang W, Qiao X, Wang Q, Yu S, Ye M, Toxicol. Appl. Pharmacol., 326, 25 (2017)

[17] Song W, Qiao X, Chen K, Wang Y, Ji S, Feng J, Li K, Lin Y, Ye M, Anal. Chem., 89, 3146 (2017)

[18] Qiao X, Liu CF, Ji S, Lin XH, Guo DA, Ye M, Planta Med., 80, 237 (2014)

[19] Frisch E, Frisch M, Trucks GW, Gaussian 03, Gaussian (2003).

[20] Bayly CI, Cieplak P, Cornell WD, Kollman PA, J. Phys. Chem., 97, 10269 (1993)

[21] Liu ZP, Huang SP, Wang WC, J. Phys. Chem. B, 108(34), 12978 (2004)

[22] Wu X, Liu Z, Huang S, Wang W, Phys. Chem. Chem. Phys., 7, 2771 (2005)

[23] Case DA, Cheatham TE, Darden T, Gohlke H, Luo R, Merz KM, Onufriev A, Simmerling C, Wang B, Woods RJ, J. Comput. Chem., 26, 1668 (2005)

[24] Harvey SC, Tan RKZ, Cheatham TE, J. Comput. Chem., 19, 726 (1998)

[25] Ryckaert JP, Ciccotti G, Berendsen HJC, J. Comput. Phys., 23, 327 (1977)

[26] Hou T, Wang J, Li Y, Wang W, J. Chem. Inf. Model., 51, 69 (2011)

[27] Ressmann AK, Gaertner P, Bica K, Green Chem., 13, 1442 (2011)

[28] Zhang Y, Xu A, Lu B, Li Z, Wang J, Carbohydr. Polym., 117, 666 (2015)

[29] Pang Y, Li X, Zhou M, Li Y, Gao W, Qiu X, Holzforschung, 70, 653 (2016)

[30] Guo Z, Lue BM, Thomasen K, Meyer AS, Xu XB, Green Chem., 9, 1362 (2007)

[31] Anderson JL, Ding J, Welton T, Armstrong DW, J. Am. Chem. Soc., 124(47), 14247 (2002)

[32] Du FY, Xiao XH, Luo XJ, Li GK, Talanta, 78, 1177 (2009)

[33] Gu H, Chen F, Zhang Q, Zang J, J. Chromatogr. B, 1014, 45 (2016)

[34] Zhou Y, Wu D, Cai P, Cheng G, Huang C, Pan Y, Molecules, 20, 7683 (2015)

[35] Vongsangnak W, Gua J, Chauvatcharin S, Zhong JJ, Biochem. Eng. J., 18, 115 (2004)

[36] Chen J, Fang Q, Liu S, Yang G, Gao Y, J. Photochem. Photobiol. A-Chem., 339, 12 (2017)

[37] Yan H, Guo XL, Yuan SL, Liu CB, Langmuir, 27(10), 5762 (2011)

[38] Gao S, Kang Z, Yuan R, Liu N, Zhu P, Wang B, J. Mol. Struct., 1192, 35 (2019)

[39] Dai Y, Witkamp GJ, Verpoorte GJ, Choi YH, Anal. Chem., 85, 6272 (2013)

[40] Zhang Q, De Oliveira Vigier K, Royer S, Jerome F, Chem. Soc. Rev., 41, 7108 (2012)

[41] Egorova KS, Ananikov VP, ChemSusChem, 7, 336 (2014)

[42] Fukumoto K, Yoshizawa M, Ohno H, J. Am. Chem. Soc., 127(8), 2398 (2005)