L- 精氨酸基姜黄素衍生物的合成及抑菌性评价

doi:10.3969/j.issn.1000-1565.2021.02.007

河北大学学报(自然科学版) ›› 2021, Vol. 41 ›› Issue (2): 155-160.DOI: 10.3969/j.issn.1000-1565.2021.02.007

L- 精氨酸基姜黄素衍生物的合成及抑菌性评价

李海鹰,邱明恒,陈健,王桂静,杨文智

收稿日期:2020-08-15 出版日期:2021-03-25 发布日期:2021-04-07
作者简介:李海鹰(1973—),女,内蒙古集宁人,河北大学副教授,从事药物制剂与质量控制方面研究.E-mail:lihylihy@163.com
基金资助:
河北省自然科学基金资助项目(H2018201045);河北省高等学校科学技术研究项目(ZD2018054)

Synthesis and antibacterial evaluation of L-arginine curcumin derivative

LI Haiying, QIU Mingheng, CHEN Jian, WANG Guijing, YANG Wenzhi

Institute of Life Science and Green Development, College of Pharmacy, Hebei University, Baoding 071002, China

Received:2020-08-15 Online:2021-03-25 Published:2021-04-07

摘要/Abstract

摘要： 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.

关键词: 姜黄素, L-精氨酸, 化学接枝, 溶解度, 体外抗菌

Abstract: 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.

Key words: curcumin, L-arginine, chemical grafting, solubility, antibacterial activity in vitro

中图分类号:

李海鹰,邱明恒,陈健,王桂静,杨文智. L- 精氨酸基姜黄素衍生物的合成及抑菌性评价[J]. 河北大学学报(自然科学版), 2021, 41(2): 155-160.

LI Haiying, QIU Mingheng, CHEN Jian, WANG Guijing, YANG Wenzhi. Synthesis and antibacterial evaluation of L-arginine curcumin derivative[J]. Journal of Hebei University(Natural Science Edition), 2021, 41(2): 155-160.

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L- 精氨酸基姜黄素衍生物的合成及抑菌性评价

Synthesis and antibacterial evaluation of L-arginine curcumin derivative

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