[关键词]
[摘要]
目的 研究麻叶荨麻Urtica cannabina的化学成分及其体外降糖活性。方法 综合运用HPD-600大孔吸附树脂柱色谱、硅胶柱色谱、制备薄层色谱及半制备高效液相色谱进行分离纯化,根据化合物的理化性质和核磁共振波谱数据进行结构鉴定;并运用体外α-葡萄糖苷酶、蔗糖酶及麦芽糖酶抑制实验评价化合物的降糖活性。结果 从麻叶荨麻70%乙醇提取物中分离得到20个化合物,分别鉴定为顺式对羟基肉桂酸(1)、反式对羟基肉桂酸(2)、二甲基葵酸酯(3)、山柰酚-3-O-β-D-吡喃葡萄糖苷(4)、咖啡酸(5)、绿原酸甲酯(6)、4-O-阿魏酰奎宁酸甲酯(7)、4-羟基肉桂酸甲酯(8)、(E)-对香豆酰二甲基苹果酸酯(9)、秦皮素啶(10)、反式咖啡酸甲酯(11)、反式咖啡酸乙酯(12)、3,4-二羟基苯乙酮(13)、4-咖啡酰奎宁酸(14)、3-O-对香豆酰奎宁酸甲酯(15)、3-O-阿魏酰奎宁酸甲酯(16)、水杨酸(17)、菜豆酸(18)、5-O-对香豆酰奎宁酸甲酯(19)、5-O-阿魏酰奎宁酸甲酯(20)。体外活性筛选显示,化合物5、7对α-葡萄糖苷酶具有较好的抑制活性;化合物5、6、11、12和14对蔗糖酶和麦芽糖酶均表现出较强抑制作用。结论 化合物1、2和5~12、14~20均为酚酸类,4为黄酮类,13为酮酚类化合物。其中,化合物3、7、9、10、13、15、16、18~20均为首次从麻叶荨麻中分离得到。化合物5对3种酶均呈现显著抑制,可能为麻叶荨麻中发挥降糖作用的核心药效团结构。构效分析揭示,邻苯二酚结构和咖啡酸酯化结构共同构成了酚酸类成分抑制糖苷酶活性的关键结构基础。
[Key word]
[Abstract]
Objective To investigate the chemical constituents of Urtica cannabina and their hypoglycemic activity in vitro. Methods The compounds were isolated and purified by column chromatography of HPD-600 macroporous resin, silica gel, preparative TLC, and semi-preparative HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. The hypoglycemic activity was evaluated in vitro through their inhibitory effects on α-glucosidase, sucrase, and maltase. Results Twenty compounds were isolated and identified from the 70% ethanol extract of U. cannabina, including cis-p-hydroxycinnamic acid (1), trans-p-hydroxycinnamic acid (2), dimethyl glansreginate (3), kaempferol 3-O-β-D-glucopyranoside (4), caffeic acid (5), chlorogenic acid methyl ester (6), 4-O-feruloylquinic methyl ester (7), hydroxycinnamic acid methyl ester (8), (E)-p-coumaroyl dimethyl malate (9), fraxidin (10), trans-caffeic acid methyl ester (11), trans-caffeic acid ethyl ester (12), 3,4-dihydroxy-acetophenone (13), 4-caffeoylquinic acid (14), 3-O-p-coumaroyl quinic acid methyl ester (15), 3-O-feruloylquinic methyl ester (16), hydroxybenzoic acid (17), phaseic acid (18), 5-O-p-coumaroylquinic methyl ester (19), 5-O-feruloylquinic methyl ester (20). The in vitro activity screening revealed that compounds 5 and 7 exhibited significant inhibitory activity against α-glucosidase, while compounds 5, 6, 11, 12 and 14 displayed considerable inhibitory effects on both sucrase and maltase. Conclusion Compounds 1, 2, 5—12, and 14—20 are phenolic acids, compound 4 is a flavonoid, and compound 13 is a ketophenol. Among these, compounds 3, 7, 9, 10, 13, 15, 16, and 18—20 were isolated from U. cannabina for the first time. Compound 5 demonstrated notable inhibitory activity against all three enzymes, suggesting that it may serve as the core pharmacophoric structure for the hypoglycemic effect. Structure-activity relationship analysis indicated that the catechol structure and the caffeic acid esterification motif collectively constitute the key structural basis for the glycosidase inhibitory activity of these phenolic acids.
[中图分类号]
R284.1
[基金项目]
青海省中央引导地方科技发展资金(2025ZY008)