Novel enzymatic synthesis of 3-Hydroxybutyryl Naringin and its molecular identification and bioactive characterization

被引:0
作者
Kim, Kyeonga [1 ]
Lee, Kang Hyun [2 ]
Yang, Eunjeong [1 ]
Lee, Giwon [1 ]
Lee, Taek [1 ]
Kim, Minji [3 ]
Jeon, Heung Bae [3 ]
Byun, Eui-Hong [4 ]
Han, Jeong Moo [5 ]
Yoo, Hah Young [6 ]
Park, Chulhwan [1 ]
机构
[1] Kwangwoon Univ, Dept Chem Engn, Seoul 01897, South Korea
[2] Dongyang Mirae Univ, Dept Bioconvergence Engn, Seoul 08221, South Korea
[3] Kwangwoon Univ, Dept Chem, Seoul 01897, South Korea
[4] Kongju Natl Univ, Dept Food Sci & Technol, Yesan 32439, South Korea
[5] Korea Atom Energy Res Inst, Adv Radiat Technol Inst, Jeongeup 56212, South Korea
[6] Sangmyung Univ, Dept Biotechnol, Seoul 03016, South Korea
基金
新加坡国家研究基金会;
关键词
Antioxidant; Naringin; 3-hydroxybutyric acid; Flavonoid ester; Lipase; LIPASE-CATALYZED ESTERIFICATION; BIOCATALYTIC PREPARATION; FLAVONOID ESTERS; BIODIESEL PRODUCTION; MEDIATED SYNTHESIS; IONIC LIQUIDS; BAMBOO LEAVES; ANTIOXIDANT; ACYLATION; ACID;
D O I
10.1016/j.foodchem.2025.143590
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this study, we synthesized 6 ''-O-((+/-)-3-hydroxybutyryl)naringin (3HBN) for the first time through enzymatic esterification of naringin with 3-hydroxybutyric acid (3HB), achieving a high conversion of 80.19 % under optimized conditions within 8 h. Structural analysis via FT-IR and 1H NMR confirmed esterification at the C-6 '' hydroxyl position on the glucose moiety of naringin. Although the antioxidant capacity of 3HBN was slightly reduced compared to naringin, its enhanced lipophilicity (log P = -0.05) indicates improved bioavailability and potential for cellular absorption. Bioactivity evaluations confirmed that 3HBN exhibited stronger antiinflammatory effects than naringin by reducing TNF-alpha and increasing IL-10 in LPS-stimulated immune cells. These findings suggest that 3HBN is a promising bioactive compound with potential applications across the food, cosmetic, and pharmaceutical industries, offering both enhanced stability and effective bioactivity for targeted health benefits.
引用
收藏
页数:13
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