Naringin is one of the main flavonoids in citrus fruits and byproducts. This flavanone has been shown to be a good antioxidant nutraceutical component, and it also has potential as a gut microbiome modulator, although its applications in final formulations represent a challenge due to its low solubility, both in water and in organic solvents. This work addresses this problem by functionalizing naringin through enzymatic acylation.

The enzymatic acylation catalyzed by the lipase Novozym® 435 and using acyl donors of different chain lengths, acetate (C2), propionate (C3), and laurate (C12), yielded in conversions of 95% at 24 h and 100% at 48 h, generating a monoacylated product. Both the aqueous and solvent solubility of acylated naringin products was improved while maintaining or even increasing their antioxidant activity.

This acylation process significantly enhanced both the water and solvent solubility of the acylated naringin products while preserving or even enhancing their antioxidant activity. In addition to the gut-modulating properties of flavonoids, acylating them with short- and medium-chain fatty acids could enhance their potential applications in the emerging field of research dedicated to understanding and modulating gut health.