Tundis R, Frattaruolo L, Carullo G, Armentano B, Badolato M, Loizzo M R, Aiello F, Cappello A R
a Department of Pharmacy, Health and Nutritional Sciences , University of Calabria , Rende , Italy.
Nat Prod Res. 2019 Jan;33(2):162-168. doi: 10.1080/14786419.2018.1440224. Epub 2018 Feb 20.
Five new pinocembrin derivatives (MC1-MC5) were synthesized by Steglich reaction, and investigated for their antimicrobial, antioxidant, and anti-inflammatory activity. MC2 (oleoyl derivative) and MC3 (linoleoyl derivative) have shown the highest inhibitory effects on bacterial proliferation, with MIC values of 32 μg/mL against Staphylococcus aureus. The docosahexaenoyl derivative MC5 displayed the highest anti-inflammatory activity, decreasing NO production in LPS-stimulated macrophages with an IC value of 15.51 μg/mL higher than the positive control diclofenac (IC of 39.71 μg/mL). All new synthesized compounds showed no anti-proliferative effects on RAW 264.7 cells. Results demonstrated as the introduction of fatty acid substituents improved the biological profile of pinocembrin. Moreover, the chemical nature of substituents significantly affects the bioactivity. These preliminary results outline the importance to investigate the synthesis of pinocembrin fatty acids derivatives as new and safe anti-microbial/anti-inflammatory agents.
通过施陶丁格反应合成了五种新的松属素衍生物（MC1-MC5），并对其抗菌、抗氧化和抗炎活性进行了研究。MC2（油酰基衍生物）和MC3（亚油酰基衍生物）对细菌增殖显示出最高的抑制作用，对金黄色葡萄球菌的最低抑菌浓度（MIC）值为32μg/mL。二十二碳六烯酰基衍生物MC5表现出最高的抗炎活性，在脂多糖刺激的巨噬细胞中降低一氧化氮（NO）生成，其半数抑制浓度（IC）值为15.51μg/mL，高于阳性对照双氯芬酸（IC为39.71μg/mL）。所有新合成的化合物对RAW 264.7细胞均无抗增殖作用。结果表明，脂肪酸取代基的引入改善了松属素的生物学特性。此外，取代基的化学性质显著影响生物活性。这些初步结果概述了研究松属素脂肪酸衍生物作为新型安全抗菌/抗炎药物合成的重要性。
