CaLB; bifunctional prodrugs; biobased polyols; ferulic acid; green enzymatic synthesis; xylitol; Biotechnology; Bioengineering; Biochemistry; Biomedical Engineering; Applied Microbiology and Biotechnology
Abstract :
[en] Natural compounds with significant bioactive properties can be found in abundance within biomasses. Especially prominent for their anti-inflammatory, neuroprotective, antibacterial, and antioxidant activities are cinnamic acid derivatives (CAs). Ferulic acid (FA), a widely studied phenylpropanoid, exhibits a broad range of therapeutic and nutraceutical applications, demonstrating antidiabetic, anticancer, antimicrobial, and hepato- and neuroprotective activities. This research investigates the green enzymatic synthesis of innovative and potentially bifunctional prodrug derivatives of FA, designed to enhance solubility and stability profiles. Selective esterification was employed to conjugate FA with xylitol, a biobased polyol recognized for its bioactive antioxidant properties and safety profile. Furthermore, by exploiting t-amyl alcohol as a green solvent, the enzymatic synthesis of the derivative was optimized for reaction parameters including temperature, reaction time, enzyme concentration, and molar ratio. The synthesized derivative, xylitol monoferulate (XMF), represents a novel contribution to the literature. The comprehensive characterization of this compound was achieved using advanced spectroscopic methods, including 1H-NMR, 13C-NMR, COSY, HSQC, and HMBC. This study represents a significant advancement in the enzymatic synthesis of high-value biobased derivatives, demonstrating increased biological activities and setting the stage for future applications in green chemistry and the sustainable production of bioactive compounds.
Disciplines :
Chemistry
Author, co-author :
Zappaterra, Federico ; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Presini, Francesco ; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Meola, Domenico ; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Chaibi, Chaimae ; Université de Liège - ULiège > TERRA Research Centre > Chemistry for Sustainable Food and Environmental Systems (CSFES) ; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Aprile, Simona; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Lerin, Lindomar Alberto ; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Giovannini, Pier Paolo; Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via Luigi Borsari, 46, 44121 Ferrara, Italy
Language :
English
Title :
Green Biocatalysis of Xylitol Monoferulate: Candida antarctica Lipase B-Mediated Synthesis and Characterization of Novel Bifunctional Prodrug.
Publication date :
02 April 2025
Journal title :
BioTech
eISSN :
2673-6284
Publisher :
Multidisciplinary Digital Publishing Institute (MDPI), Switzerland
This research was funded by the National Recovery and Resilience Plan (NRRP), Mission 04 Component 2 Investment 1.5\u2014NextGenerationEU, Call for tender n. 3277 dated 30 December 2021. Award Number: 0001052 dated 23 June 2022.
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