Abstract
BackgroundNaringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica. Analysis of the 1H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative.ResultsAfter allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments.ConclusionUsing immobilized lipase from C. antarctica, the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid.Graphical abstract
Highlights
Naringin is an important flavanone with several biological activities, including antioxidant action
The glycosylated flavonoids have rarely been used in these preparations due their low solubility in lipophilic preparations
The enzymatic immobilization has some disadvantages as changes in enzyme kinetic behavior, decrease their residual activity, and modify the three dimensional structure by restricting the enzyme because the randomness of the enzyme-substrate interactions. These drawbacks are being circumvented by modern technology and the immobilization process offers advantages that outweigh these drawbacks [12,14]. This is because the immobilized enzyme increases stability of enzymes, so they are more resistant to changes in pH and heat treatment facilitates the removal and recovery of the enzyme after the reaction, and may even improve their synthesis activity in a medium with an organic solvent [13]
Summary
After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6′′-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6′′-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments
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