LAPSE:2023.2040
Published Article
LAPSE:2023.2040
Highly Efficient Regioselective Acylation of Dihydromyricetin Catalyzed by Lipase in Nonaqueous Solvents
February 21, 2023
Abstract
This study aimed to explore the enzymatic acylation of dihydromyricetin (DHM) to synthesized DHM derivatives with a different substituted carbon chain to improve its liposolubility. In the presence of Lipozyme TL IM, DHM was butyrylated in a 96.28% conversion in methyl tert-butyl ether under the optimized conditions (molar ratio of DHM to vinyl butyrate, 1:20; lipase dosage, 0.4 U/mg DHM; temperature, 50 °C; stirrer speed, 200 rpm; reaction time, 72 h). Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy revealed that two acylation products were formed; these were 7-O-acyl-DHM and 3-O-acyl-DHM. In addition, the liposolubility of the DHM derivatives increased with the increase in the substituted carbon chain length; their antioxidant activities were higher than that of DHM in the lecithin peroxidation system, and C8-DHM had a better effect. Therefore, enzymatic acylation broadens the application of DHM in a lipid system in the food field.
This study aimed to explore the enzymatic acylation of dihydromyricetin (DHM) to synthesized DHM derivatives with a different substituted carbon chain to improve its liposolubility. In the presence of Lipozyme TL IM, DHM was butyrylated in a 96.28% conversion in methyl tert-butyl ether under the optimized conditions (molar ratio of DHM to vinyl butyrate, 1:20; lipase dosage, 0.4 U/mg DHM; temperature, 50 °C; stirrer speed, 200 rpm; reaction time, 72 h). Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy revealed that two acylation products were formed; these were 7-O-acyl-DHM and 3-O-acyl-DHM. In addition, the liposolubility of the DHM derivatives increased with the increase in the substituted carbon chain length; their antioxidant activities were higher than that of DHM in the lecithin peroxidation system, and C8-DHM had a better effect. Therefore, enzymatic acylation broadens the application of DHM in a lipid system in the food field.
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Keywords
acylation, conversion, dihydromyricetin, lecithin peroxidation, Lipozyme TL IM
Subject
Suggested Citation
Zhu S, Du B, Huang D, Xia Y, Chen S, Li Y. Highly Efficient Regioselective Acylation of Dihydromyricetin Catalyzed by Lipase in Nonaqueous Solvents. (2023). LAPSE:2023.2040
Author Affiliations
Zhu S: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China; International Joint Laboratory on Food Safety, Jiangnan University, Wuxi 214122, China
Du B: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China; International Joint Laboratory on Food Safety, Jiangnan University, Wuxi 214122, China
Huang D: Department of Food Science and Technology, National University of Singapore, Singapore 117543, Singapore
Xia Y: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
Chen S: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
Li Y: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China; School of Food Science and Technology, Jiangnan University, Wuxi 214122, China [ORCID]
Du B: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China; International Joint Laboratory on Food Safety, Jiangnan University, Wuxi 214122, China
Huang D: Department of Food Science and Technology, National University of Singapore, Singapore 117543, Singapore
Xia Y: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
Chen S: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
Li Y: State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China; School of Food Science and Technology, Jiangnan University, Wuxi 214122, China [ORCID]
Journal Name
Processes
Volume
10
Issue
7
First Page
1368
Year
2022
Publication Date
2022-07-13
ISSN
2227-9717
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PII: pr10071368, Publication Type: Journal Article
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LAPSE:2023.2040
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https://doi.org/10.3390/pr10071368
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Feb 21, 2023
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