Journal
ANTIOXIDANTS
Volume 11, Issue 2, Pages -Publisher
MDPI
DOI: 10.3390/antiox11020242
Keywords
antioxidant; flavonoid; naringin; flavonoid ester; flavonoid oleate; lipase; esterification; enzymatic synthesis; optimization
Funding
- Mid-Career Researcher Program of National Research Foundation of Korea (NRF)
- Ministry of Science and ICT (MSIT) [NRF-2020R1A2C1007493, NRF-2018M3A9H3020459]
- Bio & Medical Technology Development Program of NRF
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In this study, naringin oleate was synthesized through enzymatic esterification with optimized reaction conditions, resulting in a high conversion rate. This study presents an efficient method for synthesis that ensures high conversion within a shorter reaction time compared to previous methods.
Naringin is a flavonoid found in citrus fruits. It exhibits biological activities, such as anticancer and antioxidant effects, but it suffers from low solubility and low stability in lipophilic systems. These drawbacks lead to difficulties in the commercial application of naringin, but they can be overcome through esterification. In this study, naringin oleate was synthesized by enzymatic esterification and optimal conditions for the reaction were investigated. Experiments were conducted focusing on the following parameters: enzyme type, enzyme concentration, molar ratio of naringin to oleic acid, reaction temperature, and reaction solvent. We further confirmed the degree of esterification based on the difference in the initial and the final naringin concentrations. A conversion of 93.10% was obtained under optimized conditions (Lipozyme TL IM 10 g/L, molar ratio 1:20, reaction temperature 40 degrees C, acetonitrile as solvent, and 48 h reaction time). Thus, naringin oleate, a high value-added material that overcomes the low hydrophobicity of naringin and enhances its performance, was obtained through esterification of naringin using oleic acid. This study presented a method for the efficient enzymatic synthesis that could ensure high conversion within a shorter reaction time compared with that required in previously reported methods.
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