L- 精氨酸基姜黄素衍生物的合成及抑菌性评价

以4-二甲氨基吡啶(DMAP)为催化剂,1-(3-二甲氨基丙基)-3-乙基碳二亚胺(EDC)为脱水剂,琥珀酸(Sa)为连接臂,通过酯化和酰胺化反应将姜黄素接枝到L-精氨酸分子上,获得新型L-精氨酸基姜黄素(Cur-Sa-Arg)衍生物,产物经UV-Vis、FT-IR、¹H NMR和DSC表征,证明已成功合成.与姜黄素相比,Cur-Sa-Arg在水中的溶解度增大约3 000倍,达到30.1 μg/mL;对铜绿假单胞菌(Pseudomonas aeruginosa)、大肠杆菌(Escherichia coli)和鼠沙门氏菌(Salmonella ratus)等革兰氏阴性菌的抑菌IC₅₀降低3~6倍,对革兰氏阳性菌中的金黄色葡萄球菌(Staphylococcus aureus)抑菌IC₅₀降低2倍.结果表明,Cur-Sa-Arg可极大改善姜黄素水中溶解度,并且具有更优的抗菌性.

Synthesis and antibacterial evaluation of L-arginine curcumin derivative

L-arginine based curcumin derivative with a succinic acid linker(Cur-Sa-Arg)was synthesized via esterification and amidation reaction using 4-dimethylaminopyridine(DMAP)and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide(EDC)as catalyzer. The product was characterized by UV-Vis, FT-IR, ¹H NMR and DSC, and the results indicated that Cur-Sa-Arg was successfully synthesized. The curcumin solubility in Cur-Sa-Arg was more than about 3 000 times higher than curcumin and reached up to 30.1 μg/mL. Moreover, the result of bacteriostatic experiment showed that the IC₅₀ values against Gram-negative bacteria including Pseudomonas aeruginosa, Escherichia coli and Salmonella ratus decreased by 3—6 times, and the IC₅₀ value against Gram-positive bacteria of Staphylococcus aureus dropped by 2 times. Compared with pure curcumin, Cur-Sa-Arg has a higher solubility and better antibacterial properties.