Skip to main content
Log in

Processing of Onion Skin Extracts with Quercetin-Molecularly Imprinted Adsorbents Working at a Wide Range of Water Content

  • Original
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

A simple adsorption process allowing a high retention of polyphenols contained in extracts of onion skin with ethanol/water volume ratio going up to 80/20 is described. We show that the straightforward processing of the extracts is possible, even at low water content, by using quercetin-molecularly imprinted (Q-MIP) adsorbents synthesized with 4-vinylpyridine (4VP) as the functional monomer. The favorable interactions between the pyridyl functional groups of 4VP and the polyphenols, as well as the improved binding site accessibility introduced by molecular imprinting, are at the source for the good performance observed with the Q-MIPs. The usefulness of the Q-MIPs in onion skin polyphenols purification, fractionation and concentration is demonstrated with few sorption/desorption steps and considering sonicated, Soxhlet and supercritical CO2 extracts. Polyphenol retention of c.a. 88% is possible with Q-MIPs (7% with non-tailored adsorbents) when directly processing ethanol/water 80/20 extracts. Protocatechuic acid and other very hydrophilic molecules (such as simple sugars) were readily removed from the extracts, leaving fractions containing mostly quercetin and quercetin derivatives. Polyphenol recovery higher than 90% (measured with quercetin) and concentration factors up to 34 times were observed with the Q-MIPs.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Demidcchik V (2015) Mechanisms of oxidative stress in plants: From classical chemistry to cell biology. Environ Exp Bot 109:212–228

    Article  Google Scholar 

  2. Teotia S, Singh D (2014) Oxidative Stress in Plants and Its Management. In: R.K. Gaur and P. Sharma (eds) Approaches to Plant Stress and their Management. Springer India. 10.1007/978-81-322-1620-9_13

  3. Séquin M (2017) The Chemistry of Plants and Insects - Plants, Bugs and Molecules, Royal Society of Chemistry, Croydon, United Kingdom (ISBN: 978-1-78262-448-6)

  4. Watson RR (ed) (2019) Polyphenols in plants: Isolation, Purification and Extract Preparation, 2nd edn. Academic Press, New York (ISBN: 9780128137680)

    Google Scholar 

  5. Polyphenols Market Size (2019) GRAND VIEW RESEARCH, https://www.grandviewresearch.com/press-release/global-polyphenols-market. Accessed 26 Aug 2019

  6. FAOSTAT. Data for Agricultural production (2017) https://www.fao.org/faostat/en/#data/QC. Electronic version acessed in October 2019

  7. Kühn S, Wollseifen HR, Galensa R, Schulze-Kaysers N, Kunz B (2014) Sorption of flavonols from onion (Allium cepa L.) processing residues on a macroporous acrylic resin. Food Res Int 65:103–108

    Article  Google Scholar 

  8. Kammerer DR, Kammerer J, Carle R (2019) Chapter 19—adsorption and ion exchange for the recovery and fractionation of polyphenols: principles and applications. In: Watson RR (ed) Polyphenols in plants, 2nd edn. Academic Press, New York, pp 327–339 (ISBN:9780128137680)

  9. Pérez-Larrán P, Días-Reinoso B, Moure A, Alonso JL, Domínguez H (2017) Adsorption technologies to recover and concentrate food polyphenols. Curr Opin Food Sci 17:165–172

    Google Scholar 

  10. Ye L, Mattiasson B (2015) Molecularly imprinted polymers in biotechnology. Springer, Berlin

    Google Scholar 

  11. Whitcombe MJ, Kirsch N, Nicholls IA (2014) Molecular imprinting science and technology: a survey of the literature for the years 2004–2011. J Mol Recognit 27:297–401

    Article  CAS  PubMed  Google Scholar 

  12. Gomes CP, Dias RCS, Costa MRPFN (2019) Preparation of molecularly imprinted adsorbents with improved retention capability of polyphenols and their application in continuous separation processes. Chromatographia 82:893–916

    Article  CAS  Google Scholar 

  13. Gomes CP, Sadoyan G, Dias RCS, Costa MRPFN (2017) Development of molecularly imprinted polymers to target polyphenols present in plant extracts. Processes 5(72):1–24

    Google Scholar 

  14. Gomes CP, Dias RCS, Costa MRPFN (2019) Polymer Reaction Engineering Tools to Tailor Smart and Superabsorbent Hydrogels. In: Mondal M. (eds) Cellulose-Based Superabsorbent Hydrogels. Polymers and Polymeric Composites: A Reference Series. Springer Nature, Switzerland AG, https://doi.org/10.1007/978-3-319-77830-3_19

  15. Oliveira D, Freitas A, Kadhirvel P, Dias RCS, Costa MRPFN (2016) Development of high performance and facile to pack molecularly imprinted particles for aqueous applications. Biochem Eng J 111:87–99

    Article  CAS  Google Scholar 

  16. Oliveira D, Gomes CP, Dias RCS, Costa MRPFN (2016) Molecular imprinting of 5-fluorouracil in particles with surface RAFT grafted functional brushes. React Funct Polym 107:35–45

    Article  CAS  Google Scholar 

  17. Kupai J, Razali M, Buyuktiryaki S, Kecili R, Szekely G (2017) Long-term stability and reusability of molecularly imprinted polymers. Polym Chem 8:666–673

    Article  CAS  PubMed  Google Scholar 

  18. Ly TN, Hazama C, Shimoyamada M, Ando A, Kato K, Yamauchi R (2005) Antioxidative compounds from the outer scales of onion. J Agric Food Chem 53:8183–8189

    Article  CAS  PubMed  Google Scholar 

  19. Campone L, Celano R, Piccinelli AL, Pagano I, Carabetta S, Di Sanzo R, Russo M, Ibañez E, Cifuentes A, Rastrelli L (2018) Response surface methodology to optimize supercritical carbon dioxide/cosolvent extraction of brown onion skin by-product as source of nutraceutical compounds. Food Chem 269:495–502

    Article  CAS  PubMed  Google Scholar 

  20. Khiari Z, Makris DP, Kefalas P (2009) An investigation on the recovery of antioxidant phenolics from onion solid wastes employing water/ethanol-based solvent systems. Food Bioprocess Technol 2:337–343

    Article  CAS  Google Scholar 

  21. Kiassos E, Mylonaki S, Makris DP, Kefalas P (2009) Implementation of response surface methodology to optimise extraction of onion (Allium cepa) solid waste phenolics. Innov Food Sci Emerg Technol 10:246–252

    Article  CAS  Google Scholar 

  22. Bello MO, Olabanji IO, Abdul-Hammed M, Okunade TD (2013) Characterization of domestic onion wastes and bulb (Allium cepa L.): fatty acids and metal contents. Int Food Res J 20:2153–2158

    Google Scholar 

  23. Kwak J-H, Seo JM, Kim N-H, Arasu MV, Kim S, Yoon MK, Kim S-J (2017) Variation of quercetin glycoside derivatives in three onion (Allium cepa L.) varieties. Saudi J Biol Sci 24:1387–1391

    Article  CAS  PubMed  Google Scholar 

  24. Ko EY, Nile SH, Sharma K, Li GH, Park SW (2015) Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.). Saudi J Biol Sci 22:398–403

    Article  CAS  PubMed  Google Scholar 

  25. Vazquez-Armenta FJ, Cruz-Valenzuela MR, Ayala-Zavala JF (2016) Onion (Allium cepa) essential oils. In: Preedy VR (ed) Essential oils in food preservation, Flavor and Safety. Academic Press, Cambridge, pp 617–623 (ISBN: 9780124166417)

    Chapter  Google Scholar 

  26. Bhagwat S, Haytowitz DB, Holden JM (2014) USDA database for the flavonoid content of selected foods. U.S. Department of Agriculture, Beltsville

    Google Scholar 

  27. Lachman J, Proněk D, Hejtmánková A, Dudjak J, Pivec V, Faitová K (2003) Total polyphenol and main flavonoid antioxidants in different onion (Allium cepa L.) varieties. Hort Sci (Prague) 30:142–147

    Article  Google Scholar 

  28. Nile A, Nile SH, Kim DH, Keum J, Pivec YS, Seok PG, Sharma K (2018) Valorization of onion solid waste and their flavonols for assessment of cytotoxicity, enzyme inhibitory and antioxidant activities. Food Chem Toxicol 119:281–289

    Article  CAS  PubMed  Google Scholar 

  29. Sharma K, Ko EY, Assefa AD, Ha S, Nile SH, Lee ET, Park SW (2015) Temperature-dependent studies on the total phenolics, flavonoids, antioxidant activities, and sugar content in six onion varieties. J Food Drug Anal 23:243–252

    Article  CAS  PubMed  Google Scholar 

  30. Lesjak M, Beara I, Simin N, Pintać D, Majkić T, Bekvalac K, Orčić D, Mimica-Dukić N (2018) Antioxidant and anti-inflammatory activities of quercetin and its derivatives. J Funct Foods 40:68–75

    Article  CAS  Google Scholar 

  31. Olayeriju OS, Olaleye MT, Crown OO, Komolafe K, Boligon AA, Athayde ML, Akindahunsi AA (2015) Ethylacetate extract of red onion (Allium cepa L.) tunic affects hemodynamic parameters in rats. Food Sci Hum Wellness 4:115–122

    Article  Google Scholar 

  32. Lee WS, Yi SM, Yun JW, Jung JH, Kim DH, Kim HJ, Chang S-H, Kim G, Ryu CH, Shin SC, Hong SC, Choi YH, Jung J-M (2014) Polyphenols Isolated from Allium cepa L. induces apoptosis by induction of p53 and suppression of Bcl-2 through inhibiting PI3K/Akt signaling pathway in AGS human cancer cells. J Cancer Prev 19:14–21

    Article  PubMed  PubMed Central  Google Scholar 

  33. Kawabata K, Mukai R, Ishisaka A (2015) Quercetin and related polyphenols: new insights and implications for their bioactivity and bioavailability. Food Funct 6:1399–1417

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work is a result of project “AIProcMat@N2020—Advanced Industrial Processes and Materials for a Sustainable Northern Region of Portugal 2020”, with the reference NORTE-01-0145-FEDER-000006, supported by Norte Portugal Regional Operational Programa (NORTE 2020), under the Portugal 2020 Partnership Agreement, through the European Regional Development Fund (ERDF) and of Project POCI-01-0145-FEDER-006984—Associate Laboratory LSRE-LCM funded by ERDF through COMPETE2020—Programa Operacional Competitividade e Internacionalização (POCI)—and by national funds through FCT—Fundação para a Ciência e a Tecnologia.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Rolando C. S. Dias.

Ethics declarations

Conflict of interest

The authors declare a total absence of conflicts of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 3101 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gomes, C.P., Franco, V., Dias, R.C.S. et al. Processing of Onion Skin Extracts with Quercetin-Molecularly Imprinted Adsorbents Working at a Wide Range of Water Content. Chromatographia 83, 1539–1551 (2020). https://doi.org/10.1007/s10337-020-03958-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-020-03958-0

Keywords

Navigation