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.
Key words
Urticaceae
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Urtica cannabina L.
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type 2 diabetes mellitus
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hypoglycemic activity in vitro
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dimethyl glansreginate
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4-O-feruloylquinic methyl ester
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fraxidin
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phaseic acid
XU Mingting, JIA Wenjing, LIU Liying, WANG Luya, YUE Min, LUO Huiqin, YUE Huilan, ZHAO Xiaohui.
Chemical constituents and in vitro hypoglycemic activity of Urtica cannabina[J].
Chinese Traditional and Herbal Drugs,
2026
, 57
(5)
: 1610
-1621
.
DOI: 10.7501/j.issn.0253-2670.2026.05.003
基金
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青海省中央引导地方科技发展资金 (2025ZY008)
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Anwar S, Khan S, Almatroudi A, et al. A review on mechanism of inhibition of advanced glycation end products formation by plant derived polyphenolic compounds[J]. Mol Biol Rep, 2021, 48(1): 787-805. Alam S, Hasan M K, Neaz S, et al. Diabetes mellitus: Insights from epidemiology, biochemistry, risk factors, diagnosis, complications and comprehensive management[J]. Diabetology, 2021, 2(2): 36-50. Dilworth L, Facey A, Omoruyi F. Diabetes mellitus and its metabolic complications: The role of adipose tissues[J]. Int J Mol Sci, 2021, 22(14): 7644. Chen S D, Lin B, Gu J Y, et al. Binding interaction of betulinic acid to α-glucosidase and its alleviation on postprandial hyperglycemia[J]. Molecules, 2022, 27(8): 2517. 向明丽, 曾亚玲, 姚佳倩, 等. 肉桂酸衍生物的合成及其抑制α-葡萄糖苷酶活性研究[J]. 化学试剂, 2025, 47(9): 108-113. 杨丽珍, 邹波, 徐玉娟, 等. 荔枝壳多酚对α-葡萄糖苷酶的抑制作用[J]. 食品科技, 2017, 42(5): 174-179. 廉武星, 林毓清. α-葡萄糖苷酶抑制剂及其临床应用研究进展[J]. 实用医药杂志, 2014, 31(6): 556-559. 柴轶涛, 胡情, 柳冬梅, 等. 源于中药的α-葡萄糖苷酶抑制剂研究进展[J]. 中国现代应用药学, 2025, 42(11): 1967-1984. Concepción Zavaleta M J, Gonzáles Yovera J G, Moreno Marreros D M, et al. Diabetic gastroenteropathy: An underdiagnosed complication[J]. World J Diabetes, 2021, 12(6): 794-809. Flatt A J, Peleckis A J, Dalton-Bakes C, et al. Automated insulin delivery for hypoglycemia avoidance and glucose counterregulation in long-standing type 1 diabetes with hypoglycemia unawareness[J]. Diabetes Technol Ther, 2023, 25(5): 302-314. 敖特根白音, 李运起, 韩艳华, 等. 国内外麻叶荨麻的研究进展[J]. 中国野生植物资源, 2015, 34(1): 32-36. 张嫚丽. 麻叶荨麻化学成分及抗炎药理活性初步研究[D]. 石家庄: 河北医科大学, 2004. 苏日娜, 罗维早, 朱继孝, 等. 荨麻属药用植物研究进展[J]. 中草药, 2018, 49(11): 2722-2728. 贾舒安, 张凡凡, 柴雨昕, 等. 荨麻属植物及其在畜禽生产中的应用研究进展[J]. 黑龙江畜牧兽医, 2024(6): 20-26. Aishan H, Baba M, Iwasaki N, et al. The constituents of Urtica cannabina used in Uighur medicine[J]. Pharm Biol, 2010, 48(5): 577-583. Wang M Y, Yang Y, Zhou X Y, et al. The chemical constituents from Urtica fissa leaves[J]. J Asian Nat Prod Res, 2018, 20(8): 709-718. 李宁, 张庆林. 荨麻属植物的化学成分和药理作用研究进展[J]. 中国新药杂志, 2007, 16(21): 1746-1750. 李晓红, 李兵兰, 赵永娜, 等. 荨麻属植物的化学成分及药理作用研究进展[J]. 中国民族民间医药杂志, 2007, 16(4): 190-193. 赵齐, 卢轩, 冯宝民. 荨麻属植物化学成分和药理活性研究进展[J]. 沈阳药科大学学报, 2013, 30(2): 160-164. 张嫚丽, 李作平. 荨麻属植物化学成分与药理活性[J]. 国外医药: 植物药分册, 2004, 19(1): 12-15. 胡媛. 裂叶荨麻降糖活性部位及化学成分研究[D]. 西安: 陕西科技大学, 2020. 何亚娟. 裂叶荨麻提取物对2型糖尿病小鼠的保护作用及机制研究[D]. 西安: 陕西科技大学, 2020. 杨文娟, 胡媛, 毛跟年, 等. 裂叶荨麻体外降糖活性化学成分[J]. 食品工业科技, 2020, 41(8): 32-36. 李亚楠, 马哈亚·艾斯江, 瞿菁晨, 等. 麻叶荨麻化学成分、药理作用及应用研究进展[J]. 中国野生植物资源, 2022, 41(10): 54-59. 陈铭扬, 马巧莹, 马佳媛, 等. 宁夏野生荨麻水提取物对糖尿病大鼠血糖血脂的调节作用[J]. 现代农业科技, 2016(1): 289-290. Long W Y, Tang H C, Zhong X, et al. Hypoglycemic and lipid-lowering effects of extracted from the aerial part of Urtica cannabina L. on alloxan-induced hypergl-ycemic mice[J]. IOP Conf Ser Earth Environ Sci, 2020, 512(1): 012097. 邢植, 刘思齐, 徐凯琳, 等. 施底肥对越冬后麻叶荨麻形态特征及产量的影响[J]. 中国草地学报, 2025, 47(9): 144-150. 许照绮, 李肖, 陈永成, 等. 干旱对麻叶荨麻生理与光合特性的影响[J]. 草地学报, 2025, 33(10): 3237-3244. 刘思齐. 施肥对麻叶荨麻抗寒性和生产性能的影响[D]. 北京: 中国农业科学院, 2024. 王慧敏, 邱晓, 谢宇, 等. 麻叶荨麻高效栽培技术[J]. 耕作与栽培, 2023, 43(6): 124-125. 韩润宝, 刘改枝, 张宇, 等. 阴山北麓麻叶荨麻栽培技术及其在畜禽生产中的应用[J]. 当代畜禽养殖业, 2024, 44(2): 33-35. 邱玮, 李国婧, 徐志伟, 等. 呼和浩特地区农牧交错带野生麻叶荨麻叶片蛋白质组成及其功能特性研究[J]. 中国饲料, 2025(5): 155-160. 闫民杰, 李钢铁, 商宇, 等. 麻叶荨麻的营养价值及其在动物生产中的应用[J]. 饲料研究, 2023, 46(17): 173-176. 张晓庆, 李维红, 金艳梅, 等. 麻叶荨麻的养分积累及饲用品质评价[J]. 中国草地学报, 2010, 32(1): 116-120. 刘乌云, 萨如拉, 齐澈力木格, 等. 麻叶荨麻与尖头叶藜混合干草替代天然牧草干草对蒙古公牛生长性能、体尺指标和养分表观消化率的影响[J]. 动物营养学报, 2022, 34(5): 3023-3031. 张晓庆, 姜超, 渠晖, 等. 麻叶荨麻全混合颗粒饲料对生长育肥羊生产性能与肉品质的影响[J]. 中国草地学报, 2020, 42(6): 101-107. Deng C X, Zhang N, Lin H L, et al. Recent progress on natural α-glucosidase inhibitors derived from the plants and microorganisms[J]. Curr Med Chem, 2025, 32(11): 2115-2141. Pan G J, Lu Y T, Wei Z Y, et al. A review on the in vitro and in vivo screening of α-glucosidase inhibitors[J]. Heliyon, 2024, 10(18): e37467. 范莉, 王业玲, 唐丽. 天然来源α-葡萄糖苷酶抑制剂筛选方法的研究进展[J]. 天然产物研究与开发, 2016, 28(2): 313-321. Zhao X H, Tao J H, Zhang T, et al. Resveratroloside alleviates postprandial hyperglycemia in diabetic mice by competitively inhibiting α-glucosidase[J]. J Agric Food Chem, 2019, 67(10): 2886-2893. Jiang S R, Zhao X H, Liu C, et al. Identification of phenolic compounds in fruits of Ribes stenocarpum Maxim. by UHPLC-QTOF/MS and their hypoglycemic effects in vitro and in vivo[J]. Food Chem, 2021, 344: 128568. Zhang B W, Li X, Sun W L, et al. Dietary flavonoids and acarbose synergistically inhibit α-glucosidase and lower postprandial blood glucose[J]. J Agric Food Chem, 2017, 65(38): 8319-8330. Liu L Y, Jia W J, Jiang S R, et al. Inhibitory activities and rules of plant gallotannins with different numbers of galloyl moieties on sucrase, maltase and α-amylase in vitro and in vivo[J]. Phytomedicine, 2023, 120: 155063. 冯美玲, 王书芳, 张兴贤. 枸杞子的化学成分研究[J]. 中草药, 2013, 44(3): 265-268. 李孟, 张志广, 王梦梦, 等. 光皮木瓜化学成分研究及其神经保护活性[J]. 中成药, 2020, 42(10): 2635-2639. 吕芳, 徐筱杰. 粗糙黄堇化学成分的研究[J]. 中草药, 2007, 38(7): 990-991. Kim H J, Shin K J, Htwe K M, et al. A new vomifoliol derivative and flavonoids from the aerial parts of Orthosiphon aristatus[J]. Nps, 2024, 30(2): 72-79. 钱文琪, 吴炜琳, 张勋豪, 等. 满江红全草化学成分研究[J]. 中草药, 2020, 51(17): 4397-4404. 李海波, 石丹枫, 刘苓娴, 等. 青蒿中咖啡酰奎宁酸类成分研究[J]. 中草药, 2024, 55(16): 5386-5397. 左月明, 徐元利, 张忠立, 等. 栀子苯丙素类化学成分研究[J]. 中药材, 2015, 38(11): 2311-2313. Suzuki R, Kan S, Sugita Y, et al. P-coumaroyl malate derivatives of the Pandanus amaryllifolius leaf and their isomerization[J]. Chem Pharm Bull, 2017, 65(12): 1191-1194. 朱成光, 张卫青, 张丽萍, 等. 多穗金粟兰的化学成分及其抗肿瘤活性[J]. 天然产物研究与开发, 2023, 35(2): 242-249. Lu C L, Zhu W, Wang D M, et al. Inhibitory effects of chemical compounds isolated from the rhizome of Smilax glabra on nitric oxide and tumor necrosis factor- α production in lipopolysaccharide-induced RAW264.7 cell[J]. Evid Based Complement Alternat Med, 2015, 2015: 602425. 刘淑娴, 宋玉洁, 王伟伟, 等. 龙葵酚类成分的研究[J]. 中成药, 2019, 41(4): 828-831. 杨梦, 郝志友, 王小兰, 等. 山茱萸中的一个新联苯类木脂素[J]. 药学学报, 2024, 59(6): 1751-1756. Janda B, Stochmal A, Montoro P, et al. Phenolics in aerial parts of Persian clover Trifolium resupinatum[J]. Nat Prod Commun, 2009, 4(12): 1661-1664. Sadhu S K, Okuyama E, Fujimoto H, et al. Prostaglandin inhibitory and antioxidant components of Cistus laurifolius, a Turkish medicinal plant[J]. J Ethnopharmacol, 2006, 108(3): 371-378. 王春辉, 魏攀蕾, 严诗楷, 等. 滇南羊耳菊乙酸乙酯部位化学成分研究(英文)[J]. 天然产物研究与开发, 2014, 26(1): 33-37. 耿剑亮, 王振中, 王秋红, 等. 红花八角茎叶的化学成分研究[J]. 中草药, 2021, 52(24): 7407-7412. 范雨欣, 徐瑞雯, 张晓祎, 等. 中华枸杞中1个新的香豆素葡萄糖苷[J]. 中草药, 2024, 55(1): 23-29. Proença C, Freitas M, Ribeiro D, et al. α-Glucosidase inhibition by flavonoids: An in vitro and in silico structure–activity relationship study[J]. J Enzyme Inhib Med Chem, 2017, 32(1): 1216-1228. Li Y Q, Zhou F C, Gao F, et al. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase[J]. J Agric Food Chem, 2009, 57(24): 11463-11468. Kato M, Ochiai R, Kozuma K, et al. Effect of chlorogenic acid intake on cognitive function in the elderly: A pilot study[J]. Evid Based Complement Alternat Med, 2018, 2018: 8608497. Oboh G, Agunloye O M, Adefegha S A, et al. Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): A comparative study[J]. J Basic Clin Physiol Pharmacol, 2015, 26(2): 165-170.