Synthesis of molecularly imprinted polymers from AnAc for the separation of γ-oryzanol

Amaraporn Kaewchada; Chunyawat Borvornpongsakul; Attasak Jaree

Korean Journal of Chemical Engineering, Vol.29, No.9, 1279-1284, September, 2012

DOI10.1007/s11814-012-0021-4 Export Citation

Synthesis of molecularly imprinted polymers from AnAc for the separation of γ-oryzanol

Amaraporn Kaewchada, Chunyawat Borvornpongsakul¹, and Attasak Jaree^{1, †}

*Department of Agro-Industrial Technology, Faculty of Applied Science, King Mongkut’s University of Technology North Bangkok, 1518, Piboonsongkram Road, Bangsue, Bangkok 10800, Thailand
¹Department of Chemical Engineering, Faculty of Engineering, Kasetsart University, Chatuchak, Bangkok 10900, Thailand

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The selectivity of gamma-oryzanol (γ-oryzanol) was recognized by molecularly imprinted polymer (MIP). Polymeric materials were successfully synthesized via thermal polymerization method using γ-oryzanol as template, anacardic acid (AnAc) as functional monomer, toluene as porogen, benzoyl peroxide (BPO) as initiator and divinylbenzene as crosslinker. Binding performance of MIPs was evaluated by MINITAP 14 for variance of analysis, linear regression analysis and adequating model through full factorial experimental technique in terms of adsorption capacity. Analysis of variance with 95% confidence level suggested significant interaction effect (amounts of template, porogen, crosslinker) on adsorption capacity of MIPs. The strongest interaction is between the amount of porogen and the amount of crosslinker. It was also found that a linear regression model for adsorption capacity represents the experimental data with the correlation coefficients (R2) greater than 0.9. The MIP synthesis with 0.8 mmol of template, 6 ml of porogen and 10 ml of crosslinker provided the highest adsorption capacity of MIP (1.14 mg/g-adsorbent). The proposed method is relatively rapid and easy to perform for the separation of γ-oryzanol in non-aqueous systems.

Keywords:Analysis of Variance;Molecularly Imprinted Polymer;Molecular Recognition;Gamma-oryzanol;Anacardic Acid

[References]

Cicero AF, Gaddi A, Phytother. Res., 15, 277 (2001)
Lilitchan S, Tangprawat C, Aryusuk K, Krisnangkura S, Chokmoh S, Krisnangkura K, Food Chem., 106, 752 (2008)
Tanaka T, Kojima T, Kawamori T, Wang A, Suzui M, Okamoto K, Mori H, Carcinogenesis., 14, 1321 (1993)
Asanoma M, Takahashi K, Miyabi M, Yamamoto K, Yoshimi N, Mori H, Kawazoe Y, Carcinogenesis., 15, 2069 (1994)
Xu Z, Godber JS, J. Am. Oil Chem. Soc., 78, 645 (2001)
Nystrom L, Makinen M, Lampi AM, Piironen V, J. Agric.Food Chem., 53, 2503 (2005)
Bucci R, Magri AD, Magri AL, Marini F, Anal. Bioanal.Chem., 375, 1254 (2003)
Patel M, Naik SN, J. Sci. Ind. Res., 63, 569 (2004)
Chen MH, Bergman CK, J. Food Compos. Anal., 18, 319 (2005)
Hu W, Wells JH, Shin TS, Godbe JS, J. Am. Oil Chem. Soc., 73, 1653 (1996)
Jesus SP, Grimaldi R, Hense H, J. Supercrit. Fluids, 55(1), 149 (2010)
Xu Z, Godber JS, J. Am. Oil Chem. Soc., 77, 547 (2000)
Celiz MD, Diana SA, Colon LA, Microchem. J., 92, 174 (2009)
Quaglia M, Lorenzi ED, Sulitzky C, Massolini G, Sellergren B, Analyst., 126, 1495 (2001)
Ebarvia BS, Binag CA, Sevilla F, Anal. Bioanal. Chem., 378, 1331 (2004)
Zhang M, Xie J, Zhao Q, Zhao Q, Chen G, Liu Z, J. Chromatogr. A., 984, 173 (2003)
Wu AH, Syu MJ, Biosen. Bioelec., 21, 2345 (2006)
Caro E, Masque N, Marce RM, Borrull F, Cormack PAG, Sherrington DC, J. Chromatogr. A., 963, 169 (2002)
Nagabhushana KS, Shobhaand SV, Ravindranath B, J. Nat.Prod., 58, 807 (1995)
Suresh SK, John THP, Aziz D, Johnson JAR, LIPIDS., 21, 241 (1986)
Menon ARR, Pillai CKS, Sudha JD, Mathew AG, J.Sci. Ind. Res., 44, 324 (1985)
Tyman JHP, Chem. Soc. Rev., 4, 499 (1979)
Paramashivappa R, Kumar PP, Vithayathil PJ, Srinivasa RA, J. Agric. Food. Chem., 49, 2548 (2001)
Nagabhushana KS, Ravindranath B, J. Agric. Food Chem., 43, 2381 (1995)
Tsunetaro K, Mitsuo K, Separation and purification of anacardic acids using anion-exchange resin, Japanese Patent JP1995000062290 (1995)
Bhunia HP, Nando GB, Chaki TK, Basak A, Lenka S, Nayak PL, Eur. Polym. J., 35, 1381 (1999)
Philip JYN, Joseph B, Lupituko LM, Ye L, Food Chem., 55, 8870 (2007)
Liu Y, Hoshina K, Haginaka J, Talanta., 1713 (2010)
Zullaikah S, Melwita E, Ju YH, Bioresour. Technol., 100(1), 299 (2009)
Montgomery DC, Design and analysis of experiments, 7th Ed., John Wiley & Sons, Inc. (2009)
Pereira SMC, Leslie G, Aust. Crit. Care., 22, 187 (2009)
Kempe H, Kempe M, Anal. Chem., 78, 3659 (2006)
Wang J, Guo R, Jiping C, Zhang Q, Liang X, Anal. Chim.Acta., 540, 307 (2005)
Song X, Wang J, Zhu J, Mater. Res., 12, 299 (2009)
Hsu ST, Chen LC, Lee CC, Pan TC, You BX, Yan QF, J. Hazard. Mater., 171(1-3), 465 (2009)

[Referenced By]

[1] Cicero AF, Gaddi A, Phytother. Res., 15, 277 (2001)

[2] Lilitchan S, Tangprawat C, Aryusuk K, Krisnangkura S, Chokmoh S, Krisnangkura K, Food Chem., 106, 752 (2008)

[3] Tanaka T, Kojima T, Kawamori T, Wang A, Suzui M, Okamoto K, Mori H, Carcinogenesis., 14, 1321 (1993)

[4] Asanoma M, Takahashi K, Miyabi M, Yamamoto K, Yoshimi N, Mori H, Kawazoe Y, Carcinogenesis., 15, 2069 (1994)

[5] Xu Z, Godber JS, J. Am. Oil Chem. Soc., 78, 645 (2001)

[6] Nystrom L, Makinen M, Lampi AM, Piironen V, J. Agric.Food Chem., 53, 2503 (2005)

[7] Bucci R, Magri AD, Magri AL, Marini F, Anal. Bioanal.Chem., 375, 1254 (2003)

[8] Patel M, Naik SN, J. Sci. Ind. Res., 63, 569 (2004)

[9] Chen MH, Bergman CK, J. Food Compos. Anal., 18, 319 (2005)

[10] Hu W, Wells JH, Shin TS, Godbe JS, J. Am. Oil Chem. Soc., 73, 1653 (1996)

[11] Jesus SP, Grimaldi R, Hense H, J. Supercrit. Fluids, 55(1), 149 (2010)

[12] Xu Z, Godber JS, J. Am. Oil Chem. Soc., 77, 547 (2000)

[13] Celiz MD, Diana SA, Colon LA, Microchem. J., 92, 174 (2009)

[14] Quaglia M, Lorenzi ED, Sulitzky C, Massolini G, Sellergren B, Analyst., 126, 1495 (2001)

[15] Ebarvia BS, Binag CA, Sevilla F, Anal. Bioanal. Chem., 378, 1331 (2004)

[16] Zhang M, Xie J, Zhao Q, Zhao Q, Chen G, Liu Z, J. Chromatogr. A., 984, 173 (2003)

[17] Wu AH, Syu MJ, Biosen. Bioelec., 21, 2345 (2006)

[18] Caro E, Masque N, Marce RM, Borrull F, Cormack PAG, Sherrington DC, J. Chromatogr. A., 963, 169 (2002)

[19] Nagabhushana KS, Shobhaand SV, Ravindranath B, J. Nat.Prod., 58, 807 (1995)

[20] Suresh SK, John THP, Aziz D, Johnson JAR, LIPIDS., 21, 241 (1986)

[21] Menon ARR, Pillai CKS, Sudha JD, Mathew AG, J.Sci. Ind. Res., 44, 324 (1985)

[22] Tyman JHP, Chem. Soc. Rev., 4, 499 (1979)

[23] Paramashivappa R, Kumar PP, Vithayathil PJ, Srinivasa RA, J. Agric. Food. Chem., 49, 2548 (2001)

[24] Nagabhushana KS, Ravindranath B, J. Agric. Food Chem., 43, 2381 (1995)

[25] Tsunetaro K, Mitsuo K, Separation and purification of anacardic acids using anion-exchange resin, Japanese Patent JP1995000062290 (1995)

[26] Bhunia HP, Nando GB, Chaki TK, Basak A, Lenka S, Nayak PL, Eur. Polym. J., 35, 1381 (1999)

[27] Philip JYN, Joseph B, Lupituko LM, Ye L, Food Chem., 55, 8870 (2007)

[28] Liu Y, Hoshina K, Haginaka J, Talanta., 1713 (2010)

[29] Zullaikah S, Melwita E, Ju YH, Bioresour. Technol., 100(1), 299 (2009)

[30] Montgomery DC, Design and analysis of experiments, 7th Ed., John Wiley & Sons, Inc. (2009)

[31] Pereira SMC, Leslie G, Aust. Crit. Care., 22, 187 (2009)

[32] Kempe H, Kempe M, Anal. Chem., 78, 3659 (2006)

[33] Wang J, Guo R, Jiping C, Zhang Q, Liang X, Anal. Chim.Acta., 540, 307 (2005)

[34] Song X, Wang J, Zhu J, Mater. Res., 12, 299 (2009)

[35] Hsu ST, Chen LC, Lee CC, Pan TC, You BX, Yan QF, J. Hazard. Mater., 171(1-3), 465 (2009)