Seungmee Lee,Hyeonmi Shin,Jihyun Bae,Taek Lee,Minji Kim,Heung Bae Jeon,Kang Hyun Lee,Hah Young Yoo,Chulhwan Park
Puerarin is a flavonoid known as a natural antioxidant found in the root ofPueraria robata. Its antioxidant, anticancer, and anti-inflammatory effects have attracted attention as a potential functional ingredient in various bioindustries. However, puerarin has limited bioavailability owing to its low lipid solubility and stability. Acylation is proposed as a synthesis method to overcome this limitation. In this study, lipase-catalyzed acylation of puerarin and various acyl donors was performed, and the enzymatic synthetic condition was optimized. Under the condition (20 g/L of Novozym 435, palmitic anhydride, 1:15, 40 °C, tetrahydrofuran (THF)), the synthesis of puerarin ester achieved a significantly high conversion (98.97%) within a short time (3 h). The molecule of the synthesized puerarin palmitate was identified by various analyses such as liquid chromatography–mass spectrometry (LC–MS), Fourier-transform infrared spectroscopy (FT-IR), and carbon-13 nuclear magnetic resonance (13C NMR). The lipid solubility and the radical scavenging activity were also evaluated. Puerarin palmitate showed a slight decrease in antioxidant activity, but lipid solubility was significantly improved, improving bioavailability. The high conversion achieved for puerarin esters in this study will provide the foundation for industrial applications.Keywords:antioxidant;flavonoid;puerarin;flavonoid ester;lipase;lipid solubility
Ming-Ming Zheng,Lian Wang,Feng-Hong Huang,Ping-Mei Guo,Fang Wei,Qian-Chun Deng,Chang Zheng,Chu-Yun Wan
This study was focused on the enzymatic esterification of rutin and naringin with different free unsaturated fatty acids to produce the corresponding flavonoid esters catalyzed by Novozym 435 under ultrasound pretreatment. An ultrasonic frequency of 25 kHz, power of 200 W for rutin and 150 W for naringin and time of 1 h was determined to guarantee satisfactory degree of esterification and lipase activity. The influence of substrates concentration and molar ratio was investigated subsequently. The optimum production was achieved in component solvent of acetone and 2-methyl-2-butanol for rutin and pure 2-methyl-2-butanol for naringin at 50 °C with flavonoid concentration of 40 mM and flavonoid to fatty acid molar ratio of 1:4, resulting in a flavonoid esters conversion of above 83.2% in relative short reaction time (48–72 h). In optimum conditions, the overall esterification reaction time using the ultrasonic pretreatment process was 24 h shorter than that of mechanical stirring process without damaging the lipase activity.
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