Carboxymethyl chitosan-quercetin conjugate: A sustainable one-step synthesis and use for food preservation

Aviad Sela; Noa Shkuri; Nimrod Tish; Yakov Vinokur; Victor Rodov; Elena Poverenov

doi:10.1016/j.carbpol.2023.121084

Carboxymethyl chitosan-quercetin conjugate: A sustainable one-step synthesis and use for food preservation

Carbohydr Polym. 2023 Sep 15:316:121084. doi: 10.1016/j.carbpol.2023.121084. Epub 2023 Jun 1.

Authors

Aviad Sela¹, Noa Shkuri², Nimrod Tish³, Yakov Vinokur⁴, Victor Rodov⁵, Elena Poverenov⁶

Affiliations

¹ Agro-Nanotechnology and Advanced Materials Center, Department of Food Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel; Institute of Biochemistry, Food Science and Nutrition, The Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, Rehovot 7610001, Israel. Electronic address: avisela2005@gmail.com.
² Agro-Nanotechnology and Advanced Materials Center, Department of Food Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel; Institute of Biochemistry, Food Science and Nutrition, The Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, Rehovot 7610001, Israel. Electronic address: noa.shkuri@mail.huji.ac.il.
³ Department of Postharvest Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel; The Goodman Faculty of Life Sciences, Bar-Ilan University, Ramat Gan 5290002, Israel. Electronic address: nimrod.tish@mail.huji.ac.il.
⁴ Department of Postharvest Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel. Electronic address: yvinokur@volcani.agri.gov.il.
⁵ Department of Postharvest Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel. Electronic address: vrodov@volcani.agri.gov.il.
⁶ Agro-Nanotechnology and Advanced Materials Center, Department of Food Science, Agricultural Research Organization, The Volcani Institute, Rishon LeZion 7505101, Israel. Electronic address: elenap@volcani.agri.gov.il.

PMID: 37321704
DOI: 10.1016/j.carbpol.2023.121084

Abstract

Bioactive polysaccharide, carboxymethyl chitosan-quercetin (CMCS-q) was prepared by a one-step reaction utilizing Schiff base chemistry. Notably, the presented conjugation method involves neither radical reactions nor auxiliary coupling agents. Physicochemical properties and bioactivity of the modified polymer were studied and compared to those of the pristine carboxymethyl chitosan, CMCS. The modified CMCS-q demonstrated antioxidant activity by TEAC assay and antifungal activity by inhibiting spore germination of plant pathogen Botrytis cynerea. Then, CMCS-q was applied as an active coating on fresh-cut apples. The treatment resulted in enhanced firmness, inhibited browning and improved microbiological quality of the food product. The presented conjugation method allows retaining antimicrobial and antioxidant activity of quercetin moiety in the modified biopolymer. This method can be further used as a platform for binding ketone/aldehyde-containing polyphenols and other natural compounds to form various bioactive polymers.

Keywords: Bioactive polysaccharides; Carboxymethyl chitosan; Fresh-cut apples; Quercetin; Schiff base.

MeSH terms

Anti-Infective Agents* / pharmacology
Antioxidants / chemistry
Antioxidants / pharmacology
Chitosan* / chemistry
Chitosan* / pharmacology
Food Preservation
Quercetin / chemistry
Quercetin / pharmacology

Substances

Quercetin
Antioxidants
Chitosan
Anti-Infective Agents