Structure modification of luteolin and the influence of its derivatives on biological activities

作者：Lingyang Kong, Wei‐Min Wu, Chenliang Li, Lengleng Ma, Junbai Ma, Meitong Pan, Shan Jiang, Weili Liu, Jianghan Xu, Wei Ma · 发表于：Frontiers in Nutrition · 年份：2025 · DOI：10.3389/fnut.2025.1546932 · 被引用次数：6 · 研究领域：Phytochemicals and Antioxidant Activities、Antioxidant Activity and Oxidative Stress、Natural product bioactivities and synthesis

Introduction: This research aims to synthesize luteolin derivatives from hemp seeds by means of chemical synthesis, improve the synthesis process, simplify the procedure, and increase the yield to obtain new luteolin derivatives. Additionally, anti-inflammatory and antioxidant activities of hemp seed extracts and newly synthesized substances are tested to screen out substances with high anti-inflammatory and antioxidant activities. Methods: Using luteolin as the raw material, acetyl, propionyl, and butyryl groups are introduced into the molecular structure of luteolin. A one-pot synthesis method is employed to modify the hydroxyl groups at positions 5, 7, 3', and 4' to obtain six new luteolin acyl derivatives. The molar ratio of reaction conditions is 1:4. Pyridine (20 mL) is used as the solvent, and the reaction is carried out at 25°C and 110°C. Exploring the anti-inflammatory and antioxidant activities of luteolin and its derivatives by establishing a psoriasis model. Results: The products are separated and purified by column chromatography and recrystallization, and six new luteolin acyl derivatives were synthesized: namely, 7,3',4'-tri-O-acetylated luteolin (A), 7,3',4'-tri-O-propionylated luteolin (B), 7,3',4'-tri-O-butyrylated luteolin (C), 5,7,3',4'-tetra-O-acetylated luteolin (D), 5,7,3',4'-tetra-O-propionylated luteolin (E), and 5,7,3',4'-tetra-O-butyrylated luteolin (F). By establishing a psoriasis like mouse model, the results showed that luteolin and its derivativ...