Molecularly imprinted polymer combined with multiple-component covalent organic frameworks for extraction of naringenin enantiomers

Naringenin is a plant flavonoid found in citrus fruits and is known for its anti-inflammatory and antioxidant activities. However, extracting high-purity naringenin from citrus fruits and separating its enantiomers remains challenging. This study synthesized a molecularly imprinted multiple-component covalent organic framework (MI COF) with abundant imprinted recognition sites for the first time. This MI COF combines the advantages of molecular imprinting and covalent organic frameworks into an innovative adsorbent capable of specifically recognizing and efficiently adsorbing naringenin. MI COF exhibited an excellent adsorption capacity of 121 mg/g and a superior selectivity with an imprinting factor of 2.8 for naringenin. As a result, remarkably selective extraction of naringenin from citrus fruit extracts was achieved, with recoveries and purities of 85.7 % and 87.5 %, respectively. In addition, the vitro immunological and anticancer activities of naringenin enantiomers from citrus fruit was preliminarily investigated. These findings demonstrate that MI COF is an effective sorbent for the selective adsorption and separation of naringenin and its enantiomers from plants and fruits, holding significant potential for practical applications in food and clinical fields.