Substituent effects of phenylboronic acid-functionalized resins in pH-controlled separation of catecholic flavonoids

Sang Min Lee; Jinhyo Chung; Mi Sic Gong; Bong-Hyun Jun; Dae-Hyuk Kweon; Woo-Jae Chung

Journal of Industrial and Engineering Chemistry, Vol.77, 164-170, September, 2019

DOI10.1016/j.jiec.2019.04.031 Export Citation

Substituent effects of phenylboronic acid-functionalized resins in pH-controlled separation of catecholic flavonoids

Sang Min Lee, Jinhyo Chung, Mi Sic Gong, Bong-Hyun Jun¹, Dae-Hyuk Kweon, and Woo-Jae Chung^†

Department of Integrative Biotechnology, Sungkyunkwan University Suwon, Gyeonggi-do, 16419, Republic of Korea
¹Department of Bioscience and Biotechnology, Konkuk University, Seoul, 143-701, Republic of Korea

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Gel resins modified with different phenylboronic acid derivatives were prepared for selective separation of catechol-containing flavonoids. The phenylboronic acid gel (PBA-gel) resins showed pH-dependent adsorption and release of catechol-containing flavonoid quercetin. Under optimal pH control, the PBA-gel resins exhibited high quercetin binding capacity of up to 120 mg/g of resin and demonstrate quantitative release of the specifically bound quercetin. In addition, the recyclability of PBA-gel resin was confirmed by repeated binding and hydrolysis of quercetin with no significant loss of capacity during at least five cycles, showing great potential of PBA-gels as practical tools for selective separation of catechol- containing flavonoids.

Keywords:Phenylboronic acid;Flavonoid;Quercetin;Solid-supported reagent;pH-controlled separation

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[2] Havsteen BH, Pharmacol. Ther., 96, 67 (2002)

[3] Kumar S, Pandey AK, Sci. World J., 2013, 16 (2013)

[4] Massi A, Bortolini O, Ragno D, Bernardi T, Sacchetti G, Tacchini M, De Risi C, Molecules, 22, 1270 (2017)

[5] Srivastava S, Somasagara RR, Hegde M, Nishana M, Tadi SK, Srivastava M, Choudhary B, Raghavan SC, Sci. Rep., 6, 24049 (2016)

[6] Zhang J, Zhou XH, Wang D, Sang LY, Peng YH, Tan SY, Li Q, Sep. Sci. Technol., 48(18), 2825 (2013)

[7] Pi G, Ren P, Yu J, Shi R, Yuan Z, Wang C, J. Chromatogr. A, 1192, 17 (2008)

[8] Liu Y, Bai Q, Lou S, Di D, Li J, Guo M, J. Agric. Food Chem., 80, 1555 (2012)

[9] Sandhu AK, Gu L, J. Agric. Food Chem., 61, 1441 (2013)

[10] Wang P, Geng X, Pi G, Shi R, Yuan Z, Wang C, J. Chromatogr. B, 878, 3375 (2010)

[11] Cetinkaya O, Duru ME, Cicek H, J. Chromatogr. B, 909, 51 (2012)

[12] Brooks WLA, Sumerlin BS, Chem. Rev., 116(3), 1375 (2016)

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[14] Scordino M, Di Mauro A, Passerini A, Maccarone E, J. Agric. Food Chem., 52, 1965 (2004)

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[19] Wang Q, Bao Y, Ahire J, Chao Y, Adv. Healthc. Mater., 2, 459 (2013)

[20] Narkar AR, Barker B, Clisch M, Jiang J, Lee BP, Chem. Mater., 28, 5432 (2016)

[21] Pizer R, Tihal C, Inorg. Chem., 31, 3243 (1992)

[22] Razali M, Kim JF, Attfield M, Budd PM, Drioli E, Lee YM, Szekely G, Green Chem., 17, 5196 (2015)