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

来源：

FOOD CHEMISTRY | 2025年 / 477卷

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

页数：13

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