野梧桐种子化学成分及其抗糖尿病活性研究  

Chemical constituents from Mallotus japonicus seeds and their antidiabetic activity

作　　者：顾雯艳 陈佳[1] 唐依媛 周洪娟 邵建华[1] 赵春超[1] GU Wenyan;CHEN Jia;TANG Yiyuan;ZHOU Hongjuan;SHAO Jianhua;ZHAO Chunchao(College of Biological Science and Technology,Yangzhou University,Yangzhou 225009,China)

机构地区：[1]扬州大学生物科学与技术学院,江苏扬州225009

出　　处：《扬州大学学报(农业与生命科学版)》2024年第6期81-89,共9页Journal of Yangzhou University:Agricultural and Life Science Edition

基　　金：国家自然科学基金资助项目(31201563);广西省部共建药用资源化学与药物分子工程国家重点实验室开放课题(CMEMR 2023-B06)。

摘　　要：为研究野梧桐种子乙酸乙酯萃取物的抗糖尿病活性成分,综合运用柱色谱、制备型高效液相色谱法对其进行系统的植化分离,并通过核磁共振(NMR)等谱学技术及对比文献报道进行结构鉴定。对分离得到的化合物进行体外α-葡萄糖苷酶抑制活性及抗氧化活性[DPPH、ABTS自由基清除和铁离子还原抗氧化能力(FRAP)]测试,利用分子对接技术对活性化合物的抑酶作用机制进行初步研究。结果表明:从乙酸乙酯萃取层中分离到20个化合物,分别鉴定为芹菜素(1)、山柰酚(2)、槲皮素(3)、山柰酚3-O-α-l-吡喃鼠李糖苷(4)、异鼠李素-3-O-β-d-吡喃葡萄糖-7-O-α-l-吡喃鼠李糖苷(5)、短叶苏木酚(6)、1,2-二(4-羟基-3-甲氧基苯基)-1,3-丙二醇(7)、香草酸(8)、水杨酸(9)、4-丙酮基-3,5-二甲氧基-1,4-对醌醇(10)、熊果苷(11)、它乔糖苷(12)、红景天苷(13)、水杨苷(14)、(-)-(7S,8R)-3-甲氧基-4-羟基苯基丙三醇-9-O-β-d-吡喃葡萄糖苷(15)、(-)-(7R,8R)-3,5-二甲氧基-4-羟基苯基丙三醇-9-O-β-d-吡喃葡萄糖苷(16)、(6R,9S)-9-hydroxymegastigma-4,7-dien-3-one-9-O-β-d-glucopyranoside(17)、(6S,9S)-长寿花糖苷(18)、淫羊藿次苷B1(19)和腺苷(20)。其中化合物57、920为首次从野桐属植物中分离得到。化合物13、6、7、15、16有较强的α-葡萄糖苷酶抑制活性,明显强于阳性对照阿卡波糖;化合物3和6有较好的抗氧化活性,优于阳性对照水溶性维生素E。分子对接结果显示化合物3、7均能作用于α-葡萄糖苷酶的活性中心,并与关键氨基酸残基发生相互作用,从而阻止碳水化合物进入酶活性口袋,减缓葡萄糖的生成。综上,这一该研究阐明了野梧桐种子防治糖尿病的药效物质基础,可为其开发利用提供科学依据。To study the antidiabetic constituents of Malltus japonicus seeds,a systematic phytochemical investigation was carried out by means of extensive column chromatography and preparative HPLC,and the chemical structures were determined by NMR spectroscopic analyses and comparisons with literature data.The isolated compounds were evaluated for their in vitroα-glucosidase inhibitory activity and antioxidant capacity[DPPH,ABTS radical scavenging and ferric reducing ability of plasma(FRAP)],and molecular docking was also performed.Twenty compounds were isolated from the EtOAc extract of M.japonicus seeds and identified as:apigenin(1),kaempferol(2),quercetin(3),kaempferol 3-O-α-1-rhamnopyranoside(4),isorhamnetin 3-O-β-d-glucopyranosy-7-O-α-l-rhamnopyranoside(5),brevifolin(6),1,2-bis(4-hydroxy-3-methoxyphenyl)propane-1,3-diol(7),vanillic acid(8),salicylic acid(9),4-acetonyl-3,5-dimethoxy-p-quinol(10),arbutin(11),tachioside(12),salidroside(13),salicin(14),(—)-(7S,8R)-guaiacylglycerol 9-O-β-d-glucopyranoside(15),(—)-(7R,8R)-syringylglycerol 9-Oβ-d-glucopyranoside(16),(6R,9S)-9-hydroxymegastigma-4,7-dien-3-one-9-O-β-d-glucopyranoside(17),(6 S,9S)-roseoside(18),icariside B_1(19),adenosine(20).Among them,compounds 5—7 and 9—20 were isolated from this genus for the first time.Compounds 1—3,6,7,15,and 16 exhibited significantα-glucosidase inhibitory activities in comparison to the positive control acarbose.Compounds 3 and 6 showed stronger antioxidant activities than the positive control trolox.In addition,the molecular docking results indicated that compounds3 and 7 could both extend into the active site ofα-glucosidase and interact with its key amino acid residues to prevent carbohydrates from entering the active pocket and slow down glucose production.These findings illustrated the antidiabetic material basis of M.japonicus seeds and provided a scientific foundation for its further utilization.

关 键 词：野梧桐 化学成分 Α-葡萄糖苷酶 抗氧化 分子对接 

分 类 号：S792.37[农业科学—林木遗传育种] Q949.753.5[农业科学—林学]