Advertisement

Analytical and Bioanalytical Chemistry

, Volume 402, Issue 3, pp 1337–1346 | Cite as

Molecularly imprinted polymers for selective extraction of synephrine from Aurantii Fructus Immaturus

  • Jie-Ping FanEmail author
  • Lu Zhang
  • Xue-Hong Zhang
  • Jun-zhong Huang
  • Sheng Tong
  • Tao Kong
  • Zhe-You Tian
  • Jian-Hang Zhu
Original Paper

Abstract

In this work, molecularly imprinted solid-phase extraction (MISPE) has been used to selectively enrich, purify, or remove synephrine from Aurantii Fructus Immaturus. To this end, a molecularly imprinted polymer (MIP) was prepared by self-assembly from the template synephrine, the functional monomer methacrylic acid, and the crosslinker ethylene glycol dimethacrylate in 1:4:20 molar ratio. Subsequent molecular interrogation of the MIP binding sites revealed preferential structural selectivity for synephrine relative to other structurally related naturally occurring compounds (i.e. octopamine and tyramine ). This selectivity was subsequently exploited to achieve substantial sample clean-up of extracts of crude Aurantii Fructus Immaturus and Aurantii Fructus Immaturus stir-baked with bran. The purity of synephrine in the extracts after MISPE represented approximately 24.21-fold enrichment of the synephrine in the untreated extracts of Aurantii Fructus Immaturus stir-baked with bran. High recoveries (85–90%) from the samples proved that the method was valid for selective enrichment, purification, or removal of synephrine from Aurantii Fructus Immaturus.

Figure

The Molecularly imprinted polymers for the selective extraction of synephrine

Keywords

Molecularly imprinted polymers Solid-phase extraction Synephrine Aurantii Fructus Immaturus 

Notes

Acknowledgment

Financial support from the National Natural Science Foundation of China (nos 20806037 and 20876131), the Natural Science Foundation of Jiangxi, China (no. 2007GQH1752), the Natural Science Foundation of Jiangxi Province Department of Education (no. GJJ09420), the Open Foundation of Key Laboratory of Poyang Lake Ecology and Bio-Resource Utilization of Ministry of Education (no. Z04998), and Special Funds for Graduate Student Innovation in Jiangxi Province (no. YC09B012) are gratefully acknowledged. Chang-Xu Lin is thanked for operation of the SEM.

References

  1. 1.
    Arbo MD, Schmitt GC, Limberger MF, Charão MF, Moro ÂM, Ribeiro GL, Dallegrave E, Garcia SC, Leal MB, Limberger RP (2009) Regul Toxicol Pharmacol 54:114–117CrossRefGoogle Scholar
  2. 2.
    Tang W, Eisenbrand G (1992) Chinese Drugs of Plant Origin. Springer, BerlinCrossRefGoogle Scholar
  3. 3.
    Tang F, Tao L, Luo X, Ding L, Guo M, Nie L, Yao S (2006) J Chromatogr A 1125:182–188CrossRefGoogle Scholar
  4. 4.
    Pellati F, Benvenuti S, Melegari M, Firenzuoli F (2002) J Pharm Biomed Anal 29:1113–1119CrossRefGoogle Scholar
  5. 5.
    Pellati F, Benvenuti S, Melegari M (2004) Phytochem Anal 15:220–225CrossRefGoogle Scholar
  6. 6.
    Pellati F, Benvenuti S, Melegari M (2005) J Pharm Biomed Anal 37:839–849CrossRefGoogle Scholar
  7. 7.
    Rossato LG, Costa VM, Limberger RP, de Lourdes Bastos M, Remião F (2011) Food Chem Toxicol 49:8–16CrossRefGoogle Scholar
  8. 8.
    Stohs SJ, Preuss HG, Shara M (2011) Phytother Res. doi: 10.1002/ptr.3490
  9. 9.
    Putzbach K, Rimmer CA, Sharpless KE, Wise SA, Sander LC (2007) Anal Bioanal Chem 389:197–205CrossRefGoogle Scholar
  10. 10.
    Mattoli L, Cangi F, Maidecchi A, Ghiara C, Tubaro M, Traldi P (2005) J Agric Food Chem 53:9860–9866CrossRefGoogle Scholar
  11. 11.
    Slezak T, Francis PS, Anastos N, Barnett NW (2007) Anal Chim Acta 593:98–102CrossRefGoogle Scholar
  12. 12.
    Nelson BC, Putzbach K, Sharpless KE, Sander LC (2007) J Agric Food Chem 55:9769–9775CrossRefGoogle Scholar
  13. 13.
    Pellati F, Cannazza G, Benvenuti S (2010) J Chromatogr A 1217:3503–3510CrossRefGoogle Scholar
  14. 14.
    Arbo MD, Larentis ER, Linck VM, Aboy AL, Pimentel AL, Henriques AT, Dallegrave E, Garcia SC, Leal MB, Limberger RP (2008) Food Chem Toxicol 46:2770–2775CrossRefGoogle Scholar
  15. 15.
    Pellati F, Benvenuti S (2007) J Chromatogr A 1165:58–66CrossRefGoogle Scholar
  16. 16.
    Pellati F, Benvenuti S (2007) J Chromatogr A 1161:71–88CrossRefGoogle Scholar
  17. 17.
    Rossato LG, de Pinho PG, Silva R, Carmo H, Carvalho F, Bastos ML, Costa VM, Remiáo F (2010) J Pharm Biomed Anal 52:721–726CrossRefGoogle Scholar
  18. 18.
    Andrade AS, Schmitt GC, Rossato LG, Russowsky D, Limberger RP (2009) Chromatographia S69:S225–S229CrossRefGoogle Scholar
  19. 19.
    Li Q, Huang C, Huang Y (2006) Luminescence 21:43–48CrossRefGoogle Scholar
  20. 20.
    Stewart I, Newhall W, Edwards GJ (1964) J Biol 239:930–932Google Scholar
  21. 21.
    Vitor RV, Martins MCG, Figueiredo EC, Martins I (2011) Anal Bioanal Chem 400:2109–2117CrossRefGoogle Scholar
  22. 22.
    Schwarz LJ, Danylec B, Yang Y, Harris SJ, Boysen RI, Hearn MTW (2011) J Agric Food Chem 59:3539–3543CrossRefGoogle Scholar
  23. 23.
    Chen L, Xua S, Li J (2011) Chem Soc Rev 40:2922–2942CrossRefGoogle Scholar
  24. 24.
    Cirillo G, Curcio M, Parisi OI, Iemma FPF, Spizzirri UG, Restuccia D, Picci N (2011) Food Chem 125:1058–1063CrossRefGoogle Scholar
  25. 25.
    Chen C-Y, Wang C-H, Chen A-H (2011) Talanta 84:1038–1046CrossRefGoogle Scholar
  26. 26.
    Tian M, Bi W, Row KH (2011) Anal Bioanal Chem 399:2495–2502CrossRefGoogle Scholar
  27. 27.
    Tian M, Row KH (2011) Chromatographia 73:25–31CrossRefGoogle Scholar
  28. 28.
    Zhu H, Wang Y, Yuan Y, Zeng H (2011) Anal Methods 3:348–355CrossRefGoogle Scholar
  29. 29.
    Peng L, Wang Y, Zeng H, Yuan Y (2011) Analyst 136:756–763CrossRefGoogle Scholar
  30. 30.
    Gu X, Xu R, Yuan G, Lu H, Gu B, Xie H (2010) Anal Chim Acta 675:64–70CrossRefGoogle Scholar
  31. 31.
    Lopez C, Claude B, Morin P, Max J-P, Pena R, Ribet J-P (2011) Anal Chim Acta 683:198–205CrossRefGoogle Scholar
  32. 32.
    Bui BTS, Haupt K (2010) Anal Bioanal Chem 398:2481–2492CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Jie-Ping Fan
    • 1
    • 2
    Email author
  • Lu Zhang
    • 2
  • Xue-Hong Zhang
    • 3
  • Jun-zhong Huang
    • 4
  • Sheng Tong
    • 2
  • Tao Kong
    • 2
  • Zhe-You Tian
    • 2
  • Jian-Hang Zhu
    • 1
    • 2
  1. 1.Key Laboratory of Poyang Lake Ecology and Bio-Resource Utilization of Ministry of EducationNanchang UniversityNanchangChina
  2. 2.School of Environmental and Chemical EngineeringNanchang UniversityNanchangChina
  3. 3.School of Foreign LanguageNanchang UniversityNanchangChina
  4. 4.Guang Dong Institute For Drug ControlGuangzhouChina

Personalised recommendations