Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Yesol Baek, Seungmee Lee, Jemin Son, Taek Lee, Jong-Min Oh, Sang Hun Lee, Hyun Uk Kim, Sang Woo Seo, Si Jae Park, Hah Young Yoo and Chulhwan Park
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Yesol Baek: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea
Seungmee Lee: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea
Jemin Son: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea
Taek Lee: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea
Jong-Min Oh: Department of Electronic Materials Engineering, Kwangwoon University, Seoul 01897, Korea
Sang Hun Lee: Department of Chemical and Biological Engineering, Hanbat National University, Daejeon 34158, Korea
Hyun Uk Kim: Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea
Sang Woo Seo: School of Chemical and Biological Engineering, Institute of Chemical Process, Seoul National University, Seoul 08826, Korea
Si Jae Park: Division of Chemical Engineering and Materials Science, Ewha Womans University, Seoul 03760, Korea
Hah Young Yoo: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea
Chulhwan Park: Department of Chemical Engineering, Kwangwoon University, Seoul 01897, Korea

IJERPH, 2022, vol. 19, issue 5, 1-17

Abstract: Naringin, one of the citrus flavonoids and known as a natural antioxidant, has limited bioavailability owing to its low stability and solubility. However, naringin esters formed via acylation have recently been reported to possess improved physical and chemical properties. The development of these compounds has a great potential in the food, cosmetic and pharmaceutical industries, but low conversion and productivity are barriers to industrial applications. This study aimed to improve the conversion of naringin acetate, which is formed via the enzymatic reaction between naringin and an acyl donor. An optimal reaction condition was determined by evaluating the effect of various variables (enzyme type, enzyme concentration, acyl donor, molar ratio of reactants, reaction temperature, and solvent) on the synthesis of naringin acetate. The optimal condition was as follows: 3 g/L of Lipozyme TL IM, molar ratio of 1:5 (naringin:acyl donor), reaction temperature of 40 °C, and acetonitrile as the reaction solvent. Under this condition, the maximum conversion to naringin acetate from acetic anhydride and vinyl acetate was achieved at approximately 98.5% (8 h) and 97.5% (24 h), respectively. Compared to the previously reported values, a high conversion was achieved within a short time, confirming the commercial potential of the process.

Keywords: antioxidant; flavonoid; naringin; flavonoid ester; flavonoid acetate; acylation; lipase; transesterification; enzymatic synthesis (search for similar items in EconPapers)
JEL-codes: I I1 I3 Q Q5 (search for similar items in EconPapers)
Date: 2022
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